CN113013366B - Organic electric field light-emitting components, display devices, lighting devices and anthracene compounds - Google Patents

Abstract

Translated fromChinese

本发明涉及一种具有发光层且能量效率得到改善的有机电场发光元件、显示装置、照明装置及蒽化合物，所述发光层包含式(H)所表示的蒽系化合物与作为式(D)所表示的单量体或具有多个式(D)所表示的部分结构的多聚体的多环芳香族化合物。

The present invention relates to an organic electric field light-emitting element, a display device, a lighting device and an anthracene compound having a light-emitting layer containing an anthracene compound represented by the formula (H) and an anthracene compound represented by the formula (D) with improved energy efficiency. A polycyclic aromatic compound that represents a monomer or a polymer having multiple partial structures represented by formula (D).

Description

Translated fromChinese

有机电场发光元件、显示装置、照明装置及蒽化合物Organic electroluminescent element, display device, lighting device and anthracene compound

技术领域Technical Field

本发明涉及一种有机电场发光元件以及使用其的显示装置及照明装置。另外，本发明涉及一种能够用于制造所述有机电场发光元件的蒽化合物。The present invention relates to an organic electroluminescent element and a display device and a lighting device using the same. In addition, the present invention relates to an anthracene compound that can be used to manufacture the organic electroluminescent element.

背景技术Background Art

从前，使用进行电场发光的发光元件的显示装置因可实现省电力化或薄型化而得到各种研究，进而，包含有机材料的有机电场发光元件(以下有时称为有机EL(Electroluminescence)元件)因容易轻量化或大型化而得到积极研究。特别是，关于具有作为光的三原色之一的蓝色等的发光特性的有机材料的开发及成为最优选的发光特性的多种材料的组合，迄今为止，不论高分子化合物、低分子化合物均得到积极研究。In the past, display devices using light-emitting elements that perform electroluminescence have been studied in various ways because they can achieve power saving or thinning. In addition, organic electroluminescent elements (hereinafter sometimes referred to as organic EL (Electroluminescence) elements) containing organic materials have been actively studied because they can be easily lightweight or large-scaled. In particular, the development of organic materials having light-emitting properties such as blue, which is one of the three primary colors of light, and the combination of multiple materials that have the most preferred light-emitting properties have been actively studied to date, regardless of whether they are polymer compounds or low molecular weight compounds.

有机EL元件具有如下的结构，所述结构包括：包含阳极及阴极的一对电极，以及配置于所述一对电极间、且包含有机化合物的一层或多层。在包含有机化合物的层中，有发光层，或者传输或注入空穴、电子等的电荷的电荷传输/注入层等，且已开发有适合于这些层的各种有机材料。An organic EL element has a structure including a pair of electrodes including an anode and a cathode, and one or more layers disposed between the pair of electrodes and including an organic compound. The layers including the organic compound include a light-emitting layer, a charge transport/injection layer for transporting or injecting charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

近年来，报告有以硼等为中心原子而将多个芳香族环缩合而成的多环芳香族化合物作为发光层用材料(专利文献1)。进而，在专利文献2中报告有：通过将发光层配置于一对电极间来构成有机EL元件而获得优异的有机EL元件，所述发光层含有所述多环芳香族化合物作为掺杂剂材料，进而含有特定蒽系化合物作为主体材料。In recent years, polycyclic aromatic compounds formed by condensing multiple aromatic rings with boron or the like as central atoms have been reported as materials for light-emitting layers (Patent Document 1). Furthermore, Patent Document 2 reports that an excellent organic EL element is obtained by configuring an organic EL element between a pair of electrodes, wherein the light-emitting layer contains the polycyclic aromatic compound as a dopant material and further contains a specific anthracene compound as a host material.

在专利文献3中记载有将具有蒽骨架与苯并呫吨骨架的结构的化合物用于有机EL元件的发光层或电子传输层中。Patent Document 3 describes that a compound having an anthracene skeleton and a benzoxanthene skeleton is used in a light-emitting layer or an electron-transporting layer of an organic EL device.

[现有技术文献][Prior art literature]

[专利文献][Patent Document]

[专利文献1]国际公开第2015/102118号[Patent Document 1] International Publication No. 2015/102118

[专利文献2]国际公开第2016/152544号[Patent Document 2] International Publication No. 2016/152544

[专利文献3]美国专利公开第2015-001479号说明书[Patent Document 3] U.S. Patent Publication No. 2015-001479

发明内容Summary of the invention

[发明所要解决的问题][Problems to be solved by the invention]

如所述专利文献所公开那样，作为有机EL元件中所使用的材料，已开发有各种材料或组合。进而，通过对具体的组合或添加材料进行研究，可期待提供一种不仅具有所期望的发光特性，还具有更实用且优选的特性的有机EL元件。本发明的问题在于提供一种能量效率得到改善的有机EL元件。As disclosed in the patent document, various materials or combinations have been developed as materials used in organic EL elements. Furthermore, by studying specific combinations or additive materials, it is expected to provide an organic EL element that not only has the desired luminous properties but also has more practical and preferred properties. The problem of the present invention is to provide an organic EL element with improved energy efficiency.

[解决问题的技术手段][Technical means to solve the problem]

本发明者们为了解决所述问题而进行了努力研究，结果发现通过使用包含具有蒽骨架与苯并呫吨骨架等的结构的化合物及以硼为中心原子而将多个芳香族环缩合而成的多环芳香族化合物的发光层，能量效率提高，基于所述见解而完成了本发明。The present inventors have conducted intensive studies to solve the above-mentioned problems and have found that energy efficiency is improved by using a light-emitting layer comprising a compound having a structure such as an anthracene skeleton and a benzoxanthene skeleton and a polycyclic aromatic compound in which a plurality of aromatic rings are condensed with boron as a central atom. The present invention has been completed based on the above-mentioned findings.

具体而言，本发明具有以下结构。Specifically, the present invention has the following structure.

[1]一种有机电场发光元件，包括：一对电极，包含阳极及阴极；以及发光层，配置于所述一对电极间，且所述有机电场发光元件中，[1] An organic electroluminescent device comprising: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, wherein:

所述发光层包含下述式(H)所表示的蒽系化合物与作为下述式(D)所表示的单量体或具有多个下述式(D)所表示的部分结构的多聚体的多环芳香族化合物。The light-emitting layer includes an anthracene compound represented by the following formula (H) and a polycyclic aromatic compound which is a monomer represented by the following formula (D) or a polymer having a plurality of partial structures represented by the following formula (D).

(式(H)中，(In formula (H),

R¹～R¹⁰分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，R¹ to R¹⁰ are each independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl,

其中，R¹～R¹⁰的任意n个构成L，Among them, any n of R¹ to R¹⁰ constitute L,

R²¹～R³⁰分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，R²¹ to R³⁰ are each independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl,

R²¹～R³⁰中的邻接的基彼此可键结而形成芳基环或杂芳基环，所形成的环中的至少一个氢能由可经烷基或环烷基取代的芳基、可经烷基或环烷基取代的杂芳基、烷基或环烷基取代，Adjacent groups in R²¹ to R³⁰ may be bonded to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring may be substituted by an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group,

其中，R²¹～R³⁰的任意一个构成L，Among them, any one of R²¹ to R³⁰ constitutes L,

X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂、＞Si(-R)₂或＞Se，所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，X is independently >O, >S, >NR, >C(-R)₂ , >Si(-R)₂ or >Se, and R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl,

作为X的所述＞C(-R)₂或＞Si(-R)₂中的两个R可相互键结而形成环，The two Rs in the >C(-R)₂ or >Si(-R)₂ as X may be bonded to each other to form a ring,

作为X的所述＞N-R的R可通过连结基或单键而与R²¹或R³⁰键结，The R of the >NR as X may be bonded to R²¹ or R³⁰ via a linking group or a single bond,

L与R¹～R¹⁰的任一个所键结的碳原子及R²¹～R³⁰的任一个所键结的碳原子键结，L is bonded to the carbon atom to which any one of R¹ to R¹⁰ is bonded and to the carbon atom to which any one of R²¹ to R³⁰ is bonded,

L为单键、亚烷基、可由烷基或环烷基取代的亚芳基、或者可由烷基或环烷基取代的亚杂芳基，L is a single bond, an alkylene group, an arylene group which may be substituted by an alkyl group or a cycloalkyl group, or a heteroarylene group which may be substituted by an alkyl group or a cycloalkyl group,

n为1～3的整数，n is an integer from 1 to 3,

当n为2或3时，多个L、多个X、多个R²¹、多个R²²、多个R²³、多个R²⁴、多个R²⁵、多个R²⁶、多个R²⁷、多个R²⁸、多个R²⁹、多个R³⁰分别可相互相同也可不同，When n is 2 or 3, multiple L, multiple X, multiple R²¹ , multiple R²² , multiple R²³ , multiple R²⁴ , multiple R²⁵ , multiple R²⁶ , multiple R²⁷ , multiple R²⁸ , multiple R²⁹ , and multiple R³⁰ may be the same as or different from each other.

式(H)所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代)At least one hydrogen in the compound represented by formula (H) may be substituted by a substituted silyl group, a cyano group, a halogen group or a deuterium group)

(式(D)中，(In formula (D),

A环、B环及C环分别独立地为芳基环或杂芳基环，这些环中的至少一个氢可经取代，Ring A, Ring B and Ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted.

X¹及X²分别独立地为＞O、＞C(-R)₂或＞N-R，所述＞N-R的R为可经取代的芳基、可经取代的杂芳基、可经取代的烷基或可经取代的环烷基，另外，所述＞N-R的R可通过连结基或单键而与所述A环、B环及C环中的至少一个环键结，所述＞C(-R)₂的R分别独立地为可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，所述＞C(-R)₂中的两个R可相互键结而形成环，^X1 and^X2 are independently >O, >C(-R)₂ or >NR, wherein R of the >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted or a cycloalkyl group which may be substituted. In addition, R of the >NR may be bonded to at least one of the A ring, the B ring and the C ring via a linking group or a single bond, R of the >C(-R)₂ is independently an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, and two R of the >C(-R)₂ may be bonded to each other to form a ring,

选自由所述单量体或所述多聚体中的芳基环及杂芳基环所组成的群组中的至少一者可由至少一个环烷烃缩合，所述环烷烃中的至少一个氢可经取代，所述环烷烃中的至少一个-CH₂-可由-O-取代，At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the monomer or the multimer may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one -CH₂ - in the cycloalkane may be substituted with -O-,

所述单量体或所述多聚体中的B环与C环可经由单键或-O-、-S-、-C(-R)₂-而键结，所述-C(-R)₂-的R为氢、烷基或环烷基，两个R可相互键结而形成环，The B ring and the C ring in the monomer or the polymer may be bonded via a single bond or -O-, -S-, or -C(-R)₂ -, wherein R of -C(-R)₂ - is hydrogen, alkyl, or cycloalkyl, and two Rs may bond to each other to form a ring.

所述单量体或所述多聚体中的至少一个氢可由氰基、卤素或氘取代)At least one hydrogen in the monomer or the polymer may be substituted by cyano, halogen or deuterium)

[2]根据[1]所述的有机电场发光元件，其中，所述蒽系化合物由下述式(HA)、下述式(HB)、下述式(HC)、下述式(HD)或下述式(HE)表示。[2] The organic electroluminescent element according to [1], wherein the anthracene compound is represented by the following formula (HA), the following formula (HB), the following formula (HC), the following formula (HD) or the following formula (HE).

式(HA)、式(HB)、式(HC)、式(HD)及式(HE)中，In formula (HA), formula (HB), formula (HC), formula (HD) and formula (HE),

R¹、R²、R³、R⁶、R⁷、R⁸、R⁹及R¹⁰分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除下述式(BO)所表示的化合物的任一氢而获得的一价基，R¹ , R² , R³ , R⁶ , R⁷ , R⁸ , R⁹ and R¹⁰ are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of a compound represented by the following formula (BO),

R²¹～R³⁰分别独立地为氢、碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R²¹～R³⁰中的邻接的基彼此可键结而形成碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢可由碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基取代，R²¹ to R³⁰ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms; adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

其中，R²¹～R³⁰的任意一个构成L，Among them, any one of R²¹ to R³⁰ constitutes L,

X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂，所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，X is independently >O, >S, >NR, >C(-R)₂ or >Si(-R)₂ , and R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms,

作为X的所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结，所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基，R of the >NR as X may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond, wherein R of -C(-R)₂ - is an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,

L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基，L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

式(HA)、式(HB)、式(HC)、式(HD)及式(HE)所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in each of the compounds represented by Formula (HA), Formula (HB), Formula (HC), Formula (HD) and Formula (HE) may be substituted with a substituted silyl group, a cyano group, a halogen or a deuterium.

[3]根据[2]所述的有机电场发光元件，其中，所述蒽系化合物由式(HA)或式(HB)表示。[3] The organic electroluminescent device according to [2], wherein the anthracene compound is represented by formula (HA) or formula (HB).

[4]根据[3]所述的有机电场发光元件，其中，[4] The organic electroluminescent element according to [3], wherein

R²、R³、R⁶及R⁷均为氢，R² , R³ , R⁶ and R⁷ are all hydrogen,

R⁹为碳数6～18的芳基或去除式(BO)所表示的化合物的任一氢而获得的一价基，^R9 is an aryl group having 6 to 18 carbon atoms or a monovalent group obtained by removing any hydrogen atom of the compound represented by the formula (BO),

R²¹～R³⁰中，构成L的一个以外的均为氢，Among R²¹ to R³⁰ , all except one constituting L are hydrogen atoms,

X分别独立地为＞O、＞S、＞N-R或＞C(-R)₂，所述＞N-R的R为碳数6～16的芳基，所述＞C(-R)₂的R均为甲基，X is independently >O, >S, >NR or >C(-R)₂ , R of the >NR is an aryl group having 6 to 16 carbon atoms, and R of the >C(-R)₂ is a methyl group,

L为单键或碳数6～10的亚芳基，L is a single bond or an arylene group having 6 to 10 carbon atoms,

式(HA)及式(HB)各自所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in the compound represented by each of Formula (HA) and Formula (HB) may be substituted by a substituted silyl group, a cyano group, a halogen, or a deuterium.

[5]根据[4]所述的有机电场发光元件，其中，所述蒽系化合物由下述结构式的任一者表示。[5] The organic electroluminescent device according to [4], wherein the anthracene compound is represented by any one of the following structural formulas.

(式中，D表示氘，Me表示甲基)(wherein D represents deuterium and Me represents methyl)

[6]根据[2]所述的有机电场发光元件，其中，所述蒽系化合物由式(HC)、式(HD)或式(HE)表示。[6] The organic electroluminescent element according to [2], wherein the anthracene compound is represented by formula (HC), formula (HD) or formula (HE).

[7]根据[6]所述的有机电场发光元件，其中，[7] The organic electroluminescent element according to [6], wherein

R¹、R⁸及R¹⁰均为碳数6～18的芳基，R¹ , R⁸ and R¹⁰ are all aryl groups having 6 to 18 carbon atoms,

R²¹～R³⁰中，构成L的一个以外的均为氢，Among R²¹ to R³⁰ , all except one constituting L are hydrogen atoms,

X分别独立地为＞O、＞S、＞N-R或＞C(-R)₂，所述＞N-R的R为碳数6～16的芳基，所述＞C(-R)₂的R均为甲基，X is independently >O, >S, >NR or >C(-R)₂ , R of the >NR is an aryl group having 6 to 16 carbon atoms, and R of the >C(-R)₂ is a methyl group,

L为单键或碳数6～10的亚芳基，L is a single bond or an arylene group having 6 to 10 carbon atoms,

式(HC)、式(HD)及式(HE)各自所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in the compound represented by each of Formula (HC), Formula (HD) and Formula (HE) may be substituted by a substituted silyl group, a cyano group, a halogen or a deuterium.

[8]根据[7]所述的有机电场发光元件，其中，所述蒽系化合物由下述结构式的任一者表示。[8] The organic electroluminescent device according to [7], wherein the anthracene compound is represented by any one of the following structural formulas.

(式中，D表示氘)(Wherein, D represents deuterium)

[9]根据[2]所述的有机电场发光元件，其中，式(HA)、式(HB)、式(HC)、式(HD)或式(HE)所表示的化合物中的全部的氢由氘取代。[9] The organic electroluminescent element according to [2], wherein all hydrogen atoms in the compound represented by formula (HA), formula (HB), formula (HC), formula (HD) or formula (HE) are substituted with deuterium.

[10]根据[1]至[9]中任一项所述的有机电场发光元件，其中，所述多环芳香族化合物为作为下述式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的单量体或具有多个式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的部分结构的多聚体的多环芳香族化合物。[10] An organic electroluminescent element according to any one of [1] to [9], wherein the polycyclic aromatic compound is a monomer represented by the following formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f), or a polymer having a plurality of partial structures represented by formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f).

(式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中，(In formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) and formula (D-f),

R¹～R¹¹分别独立地为氢、芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、二芳基硼基(两个芳基可经由单键或连结基键结)、烷基、环烷基、烷氧基、芳氧基或取代硅烷基，它们中的至少一个氢可由芳基、杂芳基、烷基、环烷基或取代硅烷基取代，另外，R¹～R¹¹中的邻接的基彼此可键结并与a环、b环或c环一起形成芳基环或杂芳基环，所形成的环中的至少一个氢可由芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、二芳基硼基(两个芳基可经由单键或连结基键结)、烷基、环烷基、烷氧基、芳氧基或取代硅烷基取代，它们中的至少一个氢可由芳基、杂芳基、烷基、环烷基或取代硅烷基取代，R¹ to R¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, at least one hydrogen in them may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl group, and adjacent groups in R¹ to R¹¹ may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, at least one hydrogen in them may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl group,

X_X分别独立地为＞O、＞S、＞N-R或＞C(-R)₂，所述＞N-R的R为可经取代的芳基、可经取代的杂芳基、可经取代的烷基或可经取代的环烷基，另外，所述＞C(-R)₂的R分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，_XX is independently >O, >S, >NR or >C(-R)₂ , R of >NR is aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, and R of >C(-R)₂ is independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl,

X¹及X²分别独立地为＞O、＞C(-R)₂或＞N-R，所述＞N-R的R为碳数6～12的芳基、碳数2～15的杂芳基、碳数1～6的烷基或碳数3～14的环烷基，所述＞N-R的R中的碳数6～12的芳基及碳数2～15的杂芳基均可由碳数1～6的烷基或碳数3～14的环烷基、或者取代硅烷基取代，所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与a环、b环及c环的至少一个键结，^X1 and^X2 are independently >O, >C(-R)₂ or >NR, wherein R of the >NR is an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, wherein the aryl group having 6 to 12 carbon atoms and the heteroaryl group having 2 to 15 carbon atoms in R of the >NR may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, or a substituted silyl group, and the R of the >NR may be bonded to at least one of the a ring, the b ring and the c ring via -O-, -S-, -C(-R)_2- or a single bond,

所述＞C(-R)₂的R分别独立地为碳数6～12的芳基、碳数2～15的杂芳基、碳数1～6的烷基或碳数3～14的环烷基，所述＞C(-R)₂的R中的碳数6～12的芳基及碳数2～15的杂芳基均可由碳数1～6的烷基或碳数3～14的环烷基、或者取代硅烷基取代，所述＞C(-R)₂中的两个R可相互键结而形成环，The R of the >C(-R)₂ is independently an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. The aryl group having 6 to 12 carbon atoms and the heteroaryl group having 2 to 15 carbon atoms in the R of the >C(-R)₂ may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, or a substituted silyl group. The two R of the >C(-R)₂ may be bonded to each other to form a ring.

所述单量体或所述多聚体中的a环、b环、c环、所述所形成的环、所述芳基及所述杂芳基的至少一者可由碳数3～24的至少一个环烷烃缩合，所述环烷烃中的至少一个氢可由碳数6～30的芳基、碳数2～30的杂芳基、碳数1～24的烷基或碳数3～24的环烷基取代，所述环烷烃中的至少一个-CH₂-可由-O-取代，At least one of the a ring, b ring, c ring, the formed ring, the aryl group and the heteroaryl group in the monomer or the multimer may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, at least one -CH₂ - in the cycloalkane may be substituted with -O-,

所述单量体或所述多聚体中的至少一个氢可由氰基、卤素或氘取代，At least one hydrogen in the monomer or the polymer may be substituted by cyano, halogen or deuterium,

在多聚体的情况下，为具有2个或3个式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的部分结构的二聚体或三聚体)In the case of a multimer, it is a dimer or trimer having two or three partial structures represented by formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f)

[11]根据[10]所述的有机电场发光元件，其中，所述多环芳香族化合物为作为式(D-a)所表示的单量体或具有多个式(D-a)所表示的部分结构的多聚体的多环芳香族化合物。[11] The organic electroluminescent element according to [10], wherein the polycyclic aromatic compound is a monomer represented by formula (D-a) or a polymer having a plurality of partial structures represented by formula (D-a).

[12]根据[11]所述的有机电场发光元件，其中，所述多环芳香族化合物由下述结构式的任一者表示。[12] The organic electroluminescent device according to [11], wherein the polycyclic aromatic compound is represented by any one of the following structural formulas.

(式中，D表示氘，Me表示甲基，tBu表示叔丁基)(wherein D represents deuterium, Me represents methyl, and tBu represents tert-butyl)

[13]根据[10]所述的有机电场发光元件，其中，所述多环芳香族化合物为作为式(D-b)所表示的单量体或具有多个式(D-b)所表示的部分结构的多聚体的多环芳香族化合物。[13] The organic electroluminescent element according to [10], wherein the polycyclic aromatic compound is a monomer represented by formula (D-b) or a polymer having a plurality of partial structures represented by formula (D-b).

[14]根据[13]所述的有机电场发光元件，其中，所述多环芳香族化合物由下述结构式的任一者表示。[14] The organic electroluminescent device according to [13], wherein the polycyclic aromatic compound is represented by any one of the following structural formulas.

(式中，Me表示甲基，tBu表示叔丁基)(wherein Me represents a methyl group and tBu represents a tert-butyl group)

[15]根据[1]至[14]中任一项所述的有机电场发光元件，其具有配置于所述阴极与所述发光层之间的电子传输层及电子注入层的至少一层，所述电子传输层及电子注入层的至少一层含有选自由硼烷衍生物、吡啶衍生物、荧蒽衍生物、BO系衍生物、蒽衍生物、苯并芴衍生物、氧化膦衍生物、嘧啶衍生物、芳基腈衍生物、三嗪衍生物、苯并咪唑衍生物、菲咯啉衍生物、羟基喹啉系金属络合物、噻唑衍生物、苯并噻唑衍生物、噻咯衍生物及唑啉衍生物所组成的群组中的至少一种。[15] An organic electroluminescent element according to any one of [1] to [14], comprising at least one of an electron transport layer and an electron injection layer arranged between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aromatic nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and oxazoline derivatives.

[16]根据[15]所述的有机电场发光元件，其中，所述电子传输层及电子注入层的至少一层还含有选自由碱金属、碱土金属、稀土金属、碱金属的氧化物、碱金属的卤化物、碱土金属的氧化物、碱土金属的卤化物、稀土金属的氧化物、稀土金属的卤化物、碱金属的有机络合物、碱土金属的有机络合物及稀土金属的有机络合物所组成的群组中的至少一种。[16] The organic electroluminescent element according to [15], wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes.

[17]一种显示装置，包括根据[1]至[16]中任一项所述的有机电场发光元件。[17] A display device comprising the organic electroluminescent element according to any one of [1] to [16].

[18]一种照明装置，包括根据[1]至[16]中任一项所述的有机电场发光元件。[18] A lighting device comprising the organic electroluminescent element according to any one of [1] to [16].

[19]一种化合物，其由下述式(HA')或下述式(HB')表示。[19] A compound represented by the following formula (HA') or the following formula (HB').

式(HA')及式(HB')中，In formula (HA') and formula (HB'),

R²、R³、R⁶、R⁷及R⁹分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除下述式(BO)所表示的化合物的任一氢而获得的一价基，R² , R³ , R⁶ , R⁷ and R⁹ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of a compound represented by the following formula (BO),

R²¹～R³⁰分别独立地为氢、碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R²¹～R³⁰中的邻接的基彼此可键结而形成碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢可由碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基取代，R²¹ to R³⁰ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms; adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

其中，R²¹～R³⁰的任意一个构成L，Among them, any one of R²¹ to R³⁰ constitutes L,

R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R is each independently an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结，所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基，R may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond, wherein R of -C(-R)₂ - is an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,

L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基，L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

式(HA')及式(HB')所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in each of the compounds represented by Formula (HA') and Formula (HB') may be substituted with a substituted silyl group, a cyano group, a halogen, or a deuterium.

[20]根据[19]所述的化合物，其中，R²、R³、R⁶、R⁷均为氢，R⁹为未经取代的碳数6～30的芳基或去除式(BO)所表示的化合物的任一氢而获得的一价基，且为未经取代的碳数6～12的芳基或去除式(BO)所表示的化合物的任一氢而获得的一价基，R为未经取代的碳数6～16的芳基，L均为单键。[20] The compound according to [19], wherein R² , R³ , R⁶ , and R⁷ are all hydrogen, R⁹ is an unsubstituted aryl group having 6 to 30 carbon atoms or a monovalent group obtained by removing any hydrogen atom of the compound represented by formula (BO), and is an unsubstituted aryl group having 6 to 12 carbon atoms or a monovalent group obtained by removing any hydrogen atom of the compound represented by formula (BO), R is an unsubstituted aryl group having 6 to 16 carbon atoms, and L is a single bond.

[21]一种化合物，其由下述式(HC')或下述式(HE')表示。[21] A compound represented by the following formula (HC') or the following formula (HE').

式(HC')及式(HE')中，In formula (HC') and formula (HE'),

R¹、R²、R³、R⁶、R⁷及R⁸分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除下述式(BO)所表示的化合物的任一氢而获得的一价基，R¹ , R² , R³ , R⁶ , R⁷ and R⁸ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of a compound represented by the following formula (BO),

R²¹～R³⁰分别独立地为氢、碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R²¹～R³⁰中的邻接的基彼此可键结而形成碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢可由碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基取代，R²¹ to R³⁰ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms; adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

其中，R²¹～R³⁰的任意一个构成L，Among them, any one of R²¹ to R³⁰ constitutes L,

X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂，所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，X is independently >O, >S, >NR, >C(-R)₂ or >Si(-R)₂ , and R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms,

作为X的所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结，所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基，R of the >NR as X may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond, wherein R of -C(-R)₂ - is an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,

L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基，L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

式(HC')及式(HE')所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in each of the compounds represented by Formula (HC') and Formula (HE') may be substituted with a substituted silyl group, a cyano group, a halogen, or a deuterium.

[22]根据[21]所述的化合物，其中，R²、R³、R⁶、R⁷均为氢，R¹及R⁸分别独立地为未经取代的碳数6～30的芳基，L均为单键。[22] The compound according to [21], wherein R² , R³ , R⁶ , and R⁷ are all hydrogen, R¹ and R⁸ are each independently an unsubstituted aryl group having 6 to 30 carbon atoms, and L is a single bond.

[23]一种化合物，其由下述式(HD')表示。[23] A compound represented by the following formula (HD').

式(HD')中，In the formula (HD'),

R²、R³、R⁶、R⁷及R¹⁰分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除下述式(BO)所表示的化合物的任一氢而获得的一价基，R² , R³ , R⁶ , R⁷ and R¹⁰ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of a compound represented by the following formula (BO),

R²¹～R³⁰中，任意一个为未经取代的碳数6～16的芳基，R²¹～R³⁰的任意一个构成L，R²¹～R³⁰的其他的任意一个为未经取代的碳数6～16的芳基，其他为氢，Any one of R²¹ to R³⁰ is an unsubstituted aryl group having 6 to 16 carbon atoms, any one of R²¹ to R³⁰ constitutes L, any other one of R²¹ to R³⁰ is an unsubstituted aryl group having 6 to 16 carbon atoms, and the others are hydrogen atoms,

X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂，所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，X is independently >O, >S, >NR, >C(-R)₂ or >Si(-R)₂ , and R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms,

作为X的所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结，所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基，R of the >NR as X may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond, wherein R of -C(-R)₂ - is an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,

L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基，L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

式(HD')所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in the compound represented by the formula (HD') may be substituted by a substituted silyl group, a cyano group, a halogen or a deuterium.

[24]根据[23]所述的化合物，其中，R²、R³、R⁶、R⁷均为氢，R¹⁰为未经取代的碳数6～30的芳基。[24] The compound according to [23], wherein R² , R³ , R⁶ , and R⁷ are all hydrogen, and R¹⁰ is an unsubstituted aryl group having 6 to 30 carbon atoms.

[发明的效果][Effects of the Invention]

通过本发明，可提供一种高效率、长寿命的有机EL元件。在本发明的优选形态中，进而可提供一种发光光谱的半值宽度更窄且色纯度得到改善的有机EL元件。According to the present invention, a high-efficiency, long-life organic EL element can be provided. In a preferred embodiment of the present invention, an organic EL element having a narrower half-value width of the emission spectrum and improved color purity can be provided.

附图说明BRIEF DESCRIPTION OF THE DRAWINGS

图1是表示有机EL元件的例子的概略剖面图。FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element.

符号的说明Explanation of symbols

100：有机电场发光元件100: Organic electroluminescent element

101：基板101: Substrate

102：阳极102: Anode

103：空穴注入层103: Hole injection layer

104：空穴传输层104: Hole transport layer

105：发光层105: Luminous layer

106：电子传输层106: Electron transport layer

107：电子注入层107: Electron injection layer

108：阴极108: Cathode

具体实施方式DETAILED DESCRIPTION

以下，对本发明进行详细说明。以下所记载的构成要件的说明有时基于具有代表性的实施方式或具体例而成，但本发明并不限定于此种实施方式。此外，在本说明书中，使用“～”所表示的数值范围是指包含“～”前后所记载的数值作为下限值及上限值的范围。另外，在本说明书中，结构式的说明中的“氢”是指“氢原子(H)”。Hereinafter, the present invention will be described in detail. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In addition, in this specification, the numerical range represented by "to" refers to a range including the numerical values described before and after "to" as the lower limit and the upper limit. In addition, in this specification, "hydrogen" in the description of the structural formula refers to "hydrogen atom (H)".

在本说明书中，有时以碳数来表示化学结构或取代基，但在化学结构上取代有取代基时、或者在取代基上进而取代有取代基时等的碳数是指化学结构或取代基各自的碳数，并非指化学结构与取代基的合计碳数、或取代基与取代基的合计碳数。例如，所谓“由碳数X的取代基A取代的碳数Y的取代基B”，是指“碳数X的取代基A”在“碳数Y的取代基B”上进行取代，碳数Y并非取代基A及取代基B的合计碳数。另外，例如所谓“由取代基A取代的碳数Y的取代基B”，是指“(不限定碳数的)取代基A”在“碳数Y的取代基B”上进行取代，碳数Y并非取代基A及取代基B的合计碳数。In this specification, the chemical structure or substituent is sometimes represented by the carbon number, but when the chemical structure is substituted with a substituent, or when the substituent is further substituted with a substituent, etc., the carbon number refers to the carbon number of the chemical structure or the substituent, and does not refer to the total carbon number of the chemical structure and the substituent, or the total carbon number of the substituent and the substituent. For example, the so-called "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted on "substituent B with carbon number Y", and the carbon number Y is not the total carbon number of substituent A and substituent B. In addition, for example, the so-called "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without limiting the carbon number)" is substituted on "substituent B with carbon number Y", and the carbon number Y is not the total carbon number of substituent A and substituent B.

＜＜有机电场发光元件＞＞＜＜Organic electroluminescent device＞＞

本发明的有机电场发光元件包括：一对电极，包含阳极及阴极；以及发光层，配置于所述一对电极间。所述发光层包含式(H)所表示的蒽系化合物、与式(D)所表示的多环芳香族化合物及具有多个式(D)所表示的部分结构的多环芳香族化合物的多聚体的至少一种。The organic electroluminescent element of the present invention comprises: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes. The light-emitting layer comprises at least one of an anthracene compound represented by formula (H), a polycyclic aromatic compound represented by formula (D), and a polymer of a polycyclic aromatic compound having a plurality of partial structures represented by formula (D).

1.式(H)所表示的蒽系化合物1. Anthracene compounds represented by formula (H)

本发明的有机EL元件在发光层中包含下述式(H)所表示的蒽系化合物。下述式(H)所表示的蒽系化合物优选为作为主体材料而包含于发光层中。The organic EL device of the present invention contains an anthracene compound represented by the following formula (H) in the light-emitting layer. The anthracene compound represented by the following formula (H) is preferably contained in the light-emitting layer as a host material.

式(H)中，R¹～R¹⁰分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，其中，R¹～R¹⁰的任意n个构成L。In formula (H), R¹ to R¹⁰ are each independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl, wherein any n of R¹ to R¹⁰ constitute L.

式(H)所表示的蒽系化合物具有在蒽骨架上键结有n个以下式(H-sub)所表示的基的结构。即，式(H)中的n个式(H-sub)所表示的基以外的R¹～R¹⁰均不会为式(H-sub)所表示的基。所述情况在后述的式(HA)、式(HB)、式(HC)、式(D)及下述式(HE)中也相同。The anthracene compound represented by formula (H) has a structure in which n groups represented by the following formula (H-sub) are bonded to an anthracene skeleton. That is, R¹ to R¹⁰ other than the n groups represented by formula (H-sub) in formula (H) are not groups represented by formula (H-sub). This also applies to formula (HA), formula (HB), formula (HC), formula (D) and the following formula (HE) described later.

式(H-sub)中，L、X、R²¹～R³⁰的含义与式(H)中的L、X、R²¹～R³⁰相同，*表示键结位置。In the formula (H-sub), L, X, and R²¹ to R³⁰ have the same meanings as L, X, and R²¹ to R³⁰ in the formula (H), and * indicates a bonding position.

在式(H-sub)所表示的基中，R²¹～R³⁰的任一个可构成L，优选为R²¹、R²²、R²³、R²⁴、R²⁵、R²⁸或R²⁹，更优选为R²³、R²⁸或R²⁹。在式(H)所表示的蒽系化合物中，当有2个或3个式(H-sub)所表示的基时，L所键结的环构成原子的位置(R²¹～R³⁰中的任一个)可相互相同也可不同，优选为相同。In the group represented by formula (H-sub), any one of R²¹ to R³⁰ may constitute L, preferably R²¹ , R²² , R²³ , R²⁴ , R²⁵ , R²⁸ or R²⁹ , and more preferably R²³ , R²⁸ or R²⁹ . In the anthracene compound represented by formula (H), when there are 2 or 3 groups represented by formula (H-sub), the positions of the ring-constituting atoms to which L is bonded (any one of R²¹ to R³⁰ ) may be the same or different, and are preferably the same.

式(H)中，构成L的n个以外的R¹～R¹⁰分别独立地优选为氢、可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数6～30的芳基、可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数2～30的杂芳基、碳数1～24的烷基或碳数3～24的环烷基，分别独立地更优选为氢、未经取代的碳数6～30的芳基或未经取代的碳数2～30的杂芳基，分别独立地进而优选为氢、未经取代的碳数6～12的芳基、碳数2～12的杂芳基或去除下述式(BO)所表示的化合物的任一氢而获得的一价基。In the formula (H), R¹ to R¹⁰ other than the n groups constituting L are each independently preferably hydrogen, an aryl group having 6 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, or an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, and are each independently more preferably hydrogen, an unsubstituted aryl group having 6 to 30 carbon atoms or an unsubstituted heteroaryl group having 2 to 30 carbon atoms, and are each independently further preferably hydrogen, an unsubstituted aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 12 carbon atoms, or a monovalent group obtained by removing any hydrogen of the compound represented by the following formula (BO).

式(H)中，构成L的n个以外的R¹～R¹⁰优选为全部为氢，或者一个或两个为氢以外的基，其他为氢。In the formula (H), it is preferred that all R¹ to R¹⁰ other than the n groups constituting L are hydrogen, or one or two of them are groups other than hydrogen and the others are hydrogen.

式(H)中，R²¹～R³⁰分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基。另外，R²¹～R³⁰中的邻接的基彼此可键结而形成芳基环或杂芳基环，所形成的环中的至少一个氢能由可经烷基或环烷基取代的芳基、可经烷基或环烷基取代的杂芳基、烷基或环烷基取代。其中，R²¹～R³⁰的任意一个构成L。In formula (H), R²¹ to R³⁰ are independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl. In addition, adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring may be substituted by aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl. Any one of R²¹ to R³⁰ constitutes L.

作为R²¹～R³⁰中的邻接的基彼此键结而形成芳基环或杂芳基环时的芳基环或杂芳基环，优选为碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢能由可经碳数1～24的烷基或碳数3～24的环烷基取代的碳数6～30的芳基、可经碳数1～24的烷基或碳数3～24的环烷基取代的碳数2～30的杂芳基、碳数1～24的烷基或碳数3～24的环烷基取代。When adjacent groups among R²¹ to R³⁰ are bonded to each other to form an aryl ring or a heteroaryl ring, the aryl ring or the heteroaryl ring is preferably an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms.

作为R²¹～R³⁰中的邻接的基彼此键结而形成芳基环时的“芳基环”，具体而言，可列举：作为单环系的苯环，作为二环系的联苯环，作为缩合二环系的萘环、茚环，作为三环系的三联苯环(间三联苯基、邻三联苯基、对三联苯基)，作为缩合三环系的苊环、芴环、非那烯环、菲环，作为缩合四环系的三亚苯环、芘环、并四苯环，作为缩合五环系的苝环、并五苯环等。Specific examples of the “aryl ring” when adjacent groups in R²¹ to R³⁰ are bonded to each other to form an aryl ring include a benzene ring as a monocyclic system, a biphenyl ring as a bicyclic system, a naphthalene ring and an indene ring as a condensed bicyclic system, a terphenyl ring (meta-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic system, an acenaphthene ring, fluorene ring, phenalene ring, and phenanthrene ring as a condensed tricyclic system, a triphenylene ring, a pyrene ring, and a tetracene ring as a condensed tetracyclic system, and a perylene ring and a pentacene ring as a condensed pentacyclic system.

作为R²¹～R³⁰中的邻接的基彼此键结而形成杂芳基环时的“杂芳基环”，例如可列举：吡咯环、噁唑环、异噁唑环、噻唑环、异噻唑环、咪唑环、噁二唑环、噻二唑环、三唑环、四唑环、吡唑环、吡啶环、嘧啶环、哒嗪环、吡嗪环、三嗪环、吲哚环、异吲哚环、1H-吲唑环、苯并咪唑环、苯并噁唑环、苯并噻唑环、1H-苯并三唑环、喹啉环、异喹啉环、噌啉环、喹唑啉环、喹噁啉环、酞嗪环、萘啶环、嘌呤环、蝶啶环、咔唑环、吖啶环、吩噁噻环、吩噁嗪环、吩噻嗪环、吩嗪环、吩吖硅(phenazasiline)环、吲嗪环、呋喃环、苯并呋喃环、异苯并呋喃环、二苯并呋喃环、噻吩环、苯并噻吩环、二苯并噻吩环、呋咱环、噻蒽环、吲哚并咔唑环、苯并吲哚并咔唑环、苯并苯并吲哚并咔唑环、萘并苯并呋喃环等。Examples of the “heteroaryl ring” when adjacent groups in R²¹ to R³⁰ are bonded to each other to form a heteroaryl ring include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazole ring, a In some embodiments, the present invention includes but is not limited to a quinoline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiol ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthracene ring, an indolecarbazole ring, a benzindolecarbazole ring, a benzobenzindolecarbazole ring, a naphthobenzofuran ring, and the like.

式(H)中，构成L的一个以外的R²¹～R³⁰分别独立地优选为氢、可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数6～30的芳基、可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数2～30的杂芳基、碳数1～24的烷基或碳数3～24的环烷基，更优选为均为氢。In formula (H), R²¹ to R³⁰ other than the one constituting L are each independently preferably hydrogen, an aryl group having 6 to 30 carbon atoms which may be substituted with an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms which may be substituted with an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, and more preferably all of them are hydrogen.

式(H)中，X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂、＞Si(-R)₂或＞Se，优选为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂，更优选为＞O、＞S、＞N-R或＞C(-R)₂，进而优选为＞O或＞N-R。In formula (H), X is independently >O, >S, >NR, >C(-R)₂ , >Si(-R)₂ or >Se, preferably >O, >S, >NR, >C(-R)₂ or >Si(-R)₂ , more preferably >O, >S, >NR or >C(-R)₂ , further preferably >O or >NR.

作为式(H)中的X的＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，优选为可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数6～30的芳基、可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数2～30的杂芳基、碳数1～24的烷基或碳数3～24的环烷基。R of >NR, >C(-R)₂ and >Si(-R)₂ as X in formula (H) is independently an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, preferably an aryl group having 6 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms.

作为式(H)中的X的＞C(-R)₂或＞Si(-R)₂的两个R可相互键结而形成环。所形成的环优选为碳数3～12的环烷烃环。另外，作为式(H)中的X的所述＞N-R的R可通过连结基或单键而与R²¹或R³⁰键结。例如，作为氢的R²¹或R³⁰可以与所述氢进行取代的方式键结于R(R在式(H)中与位于R²¹所键结的位置的碳原子或位于R³⁰所键结的位置的碳原子键结)。作为此时的连结基，可列举-O-、-S-或-C(-R)₂-，所述-C(-R)₂-的R为碳数1～24的烷基或碳数3～24的环烷基。Two R's of >C(-R)₂ or >Si(-R)₂ as X in formula (H) may be bonded to each other to form a ring. The formed ring is preferably a cycloalkane ring having 3 to 12 carbon atoms. In addition, R's of >NR as X in formula (H) may be bonded to^R21 or^R30 via a linking group or a single bond. For example,^R21 or^R30 as hydrogen may be bonded to R in a manner of substitution with the hydrogen (R is bonded to a carbon atom at a position to which^R21 is bonded or a carbon atom at a position to which^R30 is bonded in formula (H)). Examples of the linking group in this case include -O-, -S- or -C(-R)_2- , wherein R of -C(-R)_2- is an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms.

作为式(H)中的X的＞N-R的R优选为可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数6～30的芳基、可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数2～30的杂芳基、碳数1～24的烷基或碳数3～24的环烷基，更优选为可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数6～30的芳基，进而优选为未经取代的碳数6～10的芳基，特别优选为未经取代的苯基。R as the >N-R of X in the formula (H) is preferably an aryl group having 6 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, or an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, more preferably an aryl group having 6 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, further preferably an unsubstituted aryl group having 6 to 10 carbon atoms, and particularly preferably an unsubstituted phenyl group.

作为式(H)中的X的＞C(-R)₂及＞Si(-R)₂的R分别独立地优选为可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数6～30的芳基、可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数2～30的杂芳基、碳数1～24的烷基或碳数3～24的环烷基，更优选为碳数1～24的烷基，进而优选为碳数1～6的烷基。R of >C(-R)₂ and >Si(-R)₂ as X in formula (H) is each independently preferably an aryl group having 6 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, more preferably an alkyl group having 1 to 24 carbon atoms, and still more preferably an alkyl group having 1 to 6 carbon atoms.

作为式(H)中的X的＞C(-R)₂的R特别优选为均为甲基。It is particularly preferred that all Rs in >C(-R)₂ as X in formula (H) are methyl groups.

L为使R¹～R¹⁰的任一个所键结的碳原子与R²¹～R³⁰的任一个所键结的碳原子键结的单键或二价连结基。L为单键、亚烷基、可由烷基或环烷基取代的亚芳基、或者可由烷基或环烷基取代的亚杂芳基，优选为单键、碳数1～6的亚烷基、可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数6～30的亚芳基、或者可由碳数1～24的烷基或碳数3～24的环烷基取代的碳数2～30的亚杂芳基，更优选为碳数6～30的亚芳基或碳数2～30的亚杂芳基，进而优选为单键或碳数6～30的亚芳基。作为L，具体而言，可列举单键、1,4-亚苯基、1,3-亚苯基、1,2-亚苯基、2,7-亚萘基、2,6-亚萘基、1,4-亚萘基、2,8-二苯并亚呋喃基、2,8-二苯并亚噻吩基、4,6-二苯并亚呋喃基、4,6-二苯并亚噻吩基、2,7-N-苯基亚咔唑基、3,6-N-苯基亚咔唑基、1,8-N-苯基亚咔唑基等，优选为单键、1,4-亚苯基、1,3-亚苯基、1,2-亚苯基、2,7-亚萘基、2,6-亚萘基或1,4-亚萘基，更优选为单键。L is a single bond or a divalent linking group that bonds the carbon atom to which any one of R¹ to R¹⁰ is bonded to the carbon atom to which any one of R²¹ to R³⁰ is bonded. L is a single bond, an alkylene group, an arylene group which may be substituted by an alkyl group or a cycloalkyl group, or a heteroarylene group which may be substituted by an alkyl group or a cycloalkyl group, preferably a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, more preferably an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 2 to 30 carbon atoms, and further preferably a single bond or an arylene group having 6 to 30 carbon atoms. Specific examples of L include a single bond, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,7-naphthylene, 2,6-naphthylene, 1,4-naphthylene, 2,8-dibenzofuranylene, 2,8-dibenzothiophenylene, 4,6-dibenzofuranylene, 4,6-dibenzothiophenylene, 2,7-N-phenylcarbazolylene, 3,6-N-phenylcarbazolylene, and 1,8-N-phenylcarbazolylene. A single bond, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,7-naphthylene, 2,6-naphthylene, or 1,4-naphthylene is preferred, and a single bond is more preferred.

n为1～3的整数。n is an integer of 1 to 3.

n为2时的两个L、两个X、两个R²¹、两个R²²、两个R²³、两个R²⁴、两个R²⁵、两个R²⁶、两个R²⁷、两个R²⁸、两个R²⁹、两个R³⁰分别可相互相同也可不同，优选为均相同。n为3时的三个L、三个X、三个R²¹、三个R²²、三个R²³、三个R²⁴、三个R²⁵、三个R²⁶、三个R²⁷、三个R²⁸、三个R²⁹、三个R³⁰分别可均相同，也可为任意两个相同，还可为三个均相互不同，优选为均相同。When n is 2, two L, two X, two R²¹ , two R²² , two R²³ , two R²⁴ , two R²⁵ , two R²⁶ , two R²⁷ , two R²⁸ , two R²⁹ , and two R³⁰ may be the same or different from each other, and are preferably the same. When n is 3, three L, three X, three R²¹ , three R²² , three R²³ , three R²⁴ , three R²⁵ , three R 26, three R²⁷ , three R²⁸ , three R²⁹ , and three R³⁰ may be the same, any two^of them may be the same, or all three may be different from each other, and are preferably the same.

式(H)中的R¹～R¹⁰中，构成L的n个位置优选为相互不邻接，具体而言，优选为后述的式(HA)、式(HB)、式(HC)、式(HD)或式(HE)中所示的位置。Among R¹ to R¹⁰ in formula (H), the n positions constituting L are preferably not adjacent to each other, and specifically, are preferably the positions shown in formula (HA), formula (HB), formula (HC), formula (HD) or formula (HE) described later.

式(H)所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。例如，作为优选例，可列举式(H)中的至少一个式(H-sub)所表示的基或作为R¹～R¹⁰的芳基或杂芳基中的任意一个以上的氢由取代硅烷基、氰基或卤素取代的化合物；特别是式(H-sub)所表示的基中的任意一个氢由三甲基硅烷基或氰基取代的化合物。另外，就化合物的耐久性的观点而言，优选为式(H)所表示的化合物中的至少一个氢被取代为氘的化合物，更优选为蒽环的氢(键结于蒽环的氢及键结于蒽环的取代基中的氢)全部由氘取代或全部的氢由氘取代，更优选为全部的氢由氘取代。At least one hydrogen in the compound represented by formula (H) may be substituted by a substituted silyl group, a cyano group, a halogen or a deuterium group. For example, as a preferred example, there can be cited compounds in which at least one hydrogen in the group represented by formula (H-sub) or any one or more hydrogens in the aryl or heteroaryl groups as R¹ to R¹⁰ in formula (H) is substituted by a substituted silyl group, a cyano group or a halogen group; in particular, there can be cited compounds in which any one hydrogen in the group represented by formula (H-sub) is substituted by a trimethylsilyl group or a cyano group. In addition, from the viewpoint of the durability of the compound, it is preferred that at least one hydrogen in the compound represented by formula (H) is substituted by a deuterium group, and it is more preferred that all hydrogens in the anthracene ring (hydrogens bonded to the anthracene ring and hydrogens in the substituents bonded to the anthracene ring) are substituted by deuterium or all hydrogens are substituted by deuterium, and it is more preferred that all hydrogens are substituted by deuterium.

式(H)所表示的化合物的说明中的“芳基”为由芳基环形成的一价基。作为“芳基环”，可列举作为R²¹～R³⁰中的邻接的基彼此键结而形成芳基环时的“芳基环”而叙述的芳基环。作为式(H)所表示的化合物中的芳基，具体而言，可列举：苯基、1-萘基、2-萘基、2-联苯基、3-联苯基、4-联苯基、5'-间三联苯基等。The "aryl group" in the description of the compound represented by formula (H) is a monovalent group formed by an aryl ring. Examples of the "aryl ring" include aryl rings described as "aryl rings" when adjacent groups in R²¹ to R³⁰ are bonded to each other to form an aryl ring. Specific examples of the aryl group in the compound represented by formula (H) include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 5'-terphenylyl, and the like.

式(H)所表示的化合物的说明中的“杂芳基”为由杂芳基环形成的一价基。作为“杂芳基环”，可列举作为R²¹～R³⁰中的邻接的基彼此键结而形成杂芳基环时的“杂芳基环”而叙述的杂芳基环。The "heteroaryl group" in the description of the compound represented by formula (H) is a monovalent group formed of a heteroaryl ring. Examples of the "heteroaryl ring" include those described as "heteroaryl rings" when adjacent groups among R²¹ to R³⁰ are bonded to form a heteroaryl ring.

另外，作为“杂芳基”，可列举去除下述式(BO)所表示的化合物的任一氢而获得的一价基作为优选例。Moreover, as a "heteroaryl group", a monovalent group obtained by removing any hydrogen of a compound represented by the following formula (BO) can be mentioned as a preferred example.

作为去除式(BO)所表示的化合物的任一氢而获得的一价基，例如可列举以下基。式中*表示键结位置。Examples of the monovalent group obtained by removing any hydrogen from the compound represented by the formula (BO) include the following groups: In the formula, * represents a bonding position.

在式(H)所表示的化合物的说明中称为“烷基”时的“烷基”可为直链及支链的任一种。When an "alkyl group" is referred to in the description of the compound represented by the formula (H), the "alkyl group" may be a linear chain or a branched chain.

作为具体的烷基，可列举：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基(t-pentyl)(t-amyl)、正己基、1-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、正庚基、1-甲基己基、正辛基、叔辛基(1,1,3,3-四甲基丁基)、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、2,6-二甲基-4-庚基、3,5,5-三甲基己基、正癸基、正十一基、1-甲基癸基、正十二基、正十三基、1-己基庚基、正十四基、正十五基、正十六基、正十七基、正十八基、正二十基等。Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-icosyl.

另外，例如还可列举：1-乙基-1-甲基丙基、1,1-二乙基丙基、1,1-二甲基丁基、1-乙基-1-甲基丁基、1,1,4-三甲基戊基、1,1,2-三甲基丙基、1,1-二甲基辛基、1,1-二甲基戊基、1,1-二甲基庚基、1,1,5-三甲基己基、1-乙基-1-甲基己基、1-乙基-1,3-二甲基丁基、1,1,2,2-四甲基丙基、1-丁基-1-甲基戊基、1,1-二乙基丁基、1-乙基-1-甲基戊基、1,1,3-三甲基丁基、1-丙基-1-甲基戊基、1,1,2-三甲基丙基、1-乙基-1,2,2-三甲基丙基、1-丙基-1-甲基丁基、1,1-二甲基己基等。Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like can be mentioned.

作为在式(H)所表示的化合物的说明中称为“环烷基”时的具体的“环烷基”，可列举：环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、降冰片烯基、双环[1.0.1]丁基、双环[1.1.1]戊基、双环[2.0.1]戊基、双环[1.2.1]己基、双环[3.0.1]己基、双环[2.1.2]庚基、双环[2.2.2]辛基、金刚烷基、二金刚烷基、十氢萘基、十氢薁基及它们的碳数1～5的烷基(特别是甲基)取代物等。此外，在本说明书中，“环烷基”不仅包含环己基之类的单环式的环烷基，还包含金刚烷基之类的多环式的环烷基。Specific examples of the "cycloalkyl" referred to as "cycloalkyl" in the description of the compound represented by formula (H) include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydroazulyl, and C1-5 alkyl (particularly methyl)-substituted products thereof. In the present specification, "cycloalkyl" includes not only monocyclic cycloalkyls such as cyclohexyl but also polycyclic cycloalkyls such as adamantyl.

作为式(H)所表示的化合物中的“取代硅烷基”，例如可列举由选自由烷基、环烷基及芳基所组成的群组中的三个取代基取代的硅烷基。例如可列举：三烷基硅烷基、三环烷基硅烷基、二烷基环烷基硅烷基、烷基二环烷基硅烷基、三芳基硅烷基、二烷基芳基硅烷基及烷基二芳基硅烷基。作为式(H)所表示的化合物中的“取代硅烷基”的优选例，可列举三甲基硅烷基及三苯基硅烷基。Examples of the "substituted silyl group" in the compound represented by formula (H) include silyl groups substituted with three substituents selected from the group consisting of alkyl groups, cycloalkyl groups, and aryl groups. Examples include trialkylsilyl groups, tricycloalkylsilyl groups, dialkylcycloalkylsilyl groups, alkyldicycloalkylsilyl groups, triarylsilyl groups, dialkylarylsilyl groups, and alkyldiarylsilyl groups. Preferred examples of the "substituted silyl group" in the compound represented by formula (H) include trimethylsilyl groups and triphenylsilyl groups.

式(H)所表示的蒽系化合物优选为式(HA)、式(HB)、式(HC)、式(HD)或式(HE)所表示的蒽系化合物。The anthracene compound represented by formula (H) is preferably an anthracene compound represented by formula (HA), formula (HB), formula (HC), formula (HD) or formula (HE).

式(HA)、式(HB)、式(HC)、式(HD)及式(HE)中，R¹、R²、R³、R⁶、R⁷、R⁸、R⁹及R¹⁰分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除式(BO)所表示的化合物的任一氢而获得的一价基，R²¹～R³⁰分别独立地为氢、碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基。R²¹～R³⁰中的邻接的基彼此可键结而形成碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢可由碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基取代，其中，R²¹～R³⁰的任意一个构成L。In formula (HA), formula (HB), formula (HC), formula (HD) and formula (HE), R¹ , R² , R³ , R⁶ , R⁷ , R⁸ , R⁹ and R¹⁰ are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of the compound represented by formula (BO), and R²¹ to R³⁰ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. Adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein any one of R²¹ to R³⁰ constitutes L.

式(HA)、式(HB)、式(HC)、式(HD)及式(HE)中，X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂。所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基。作为X的所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结。所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基。X分别独立地优选为＞O、＞S、＞N-R或＞C(-R)₂，更优选为＞O或＞N-R。In formula (HA), formula (HB), formula (HC), formula (HD) and formula (HE), X is independently >O, >S, >NR, >C(-R)₂ or >Si(-R)_2. R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms. R of >NR as X may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond. R of -C(-R)₂ - is alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms. X is independently preferably >O, >S, >NR or >C(-R)₂ , and more preferably >O or >NR.

式(HA)、式(HB)、式(HC)、式(HD)及式(HE)中，L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基。L优选为单键。In formula (HA), formula (HB), formula (HC), formula (HD) and formula (HE), L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. L is preferably a single bond.

在式(HA)中，R²、R³、R⁶、R⁷分别独立地优选为氢或未经取代的碳数6～30的芳基，更优选为氢。R⁹优选为未经取代的碳数6～30的芳基或去除式(BO)所表示的化合物的任一氢而获得的一价基，更优选为未经取代的碳数6～12的芳基或去除式(BO)所表示的化合物的任一氢而获得的一价基。在后述的式(HA')中也相同。In formula (HA), R² , R³ , R⁶ , and R⁷ are each independently preferably hydrogen or an unsubstituted aryl group having 6 to 30 carbon atoms, and more preferably hydrogen.^{R 9} is preferably an unsubstituted aryl group having 6 to 30 carbon atoms, or a monovalent group obtained by removing any hydrogen atoms of the compound represented by formula (BO), and more preferably an unsubstituted aryl group having 6 to 12 carbon atoms, or a monovalent group obtained by removing any hydrogen atoms of the compound represented by formula (BO). The same applies to formula (HA') described below.

在式(HB)中，R²、R³、R⁶、R⁷分别独立地优选为氢或未经取代的碳数6～30的芳基，更优选为氢。在后述的式(HB')中也相同。In formula (HB), R² , R³ , R⁶ and R⁷ are each independently preferably hydrogen or an unsubstituted aryl group having 6 to 30 carbon atoms, more preferably hydrogen. The same applies to formula (HB') described below.

在式(HC)中，R²、R³、R⁶、R⁷分别独立地优选为氢或未经取代的碳数6～30的芳基，更优选为氢。R¹及R⁸分别独立地优选为未经取代的碳数6～30的芳基，更优选为未经取代的碳数6～12的芳基。在后述的式(HC')中也相同。In formula (HC), R² , R³ , R⁶ and R⁷ are each independently preferably hydrogen or an unsubstituted aryl group having 6 to 30 carbon atoms, more preferably hydrogen.^{R 1} and R⁸ are each independently preferably an unsubstituted aryl group having 6 to 30 carbon atoms, more preferably an unsubstituted aryl group having 6 to 12 carbon atoms. The same applies to formula (HC') described below.

在式(HD)中，R²、R³、R⁶、R⁷分别独立地优选为氢或未经取代的碳数6～30的芳基，更优选为氢。R¹⁰优选为未经取代的碳数6～30的芳基，更优选为未经取代的碳数6～12的芳基。在后述的式(HD')中也相同。In formula (HD), R² , R³ , R⁶ and R⁷ are each independently preferably hydrogen or an unsubstituted aryl group having 6 to 30 carbon atoms, more preferably hydrogen.^{R 10} is preferably an unsubstituted aryl group having 6 to 30 carbon atoms, more preferably an unsubstituted aryl group having 6 to 12 carbon atoms. The same applies to formula (HD') described below.

在式(HE)中，R²、R³、R⁶、R⁷分别独立地优选为氢或未经取代的碳数6～30的芳基，更优选为氢。在后述的式(HE')中也相同。In formula (HE), R² , R³ , R⁶ and R⁷ are each independently preferably hydrogen or an unsubstituted aryl group having 6 to 30 carbon atoms, more preferably hydrogen. The same applies to formula (HE') described below.

在式(HA)、式(HB)、式(HC)、式(HD)及式(HE)中，构成L的一个以外的R²¹～R³⁰更优选为均为氢。In formula (HA), formula (HB), formula (HC), formula (HD) and formula (HE), it is more preferred that all of R²¹ to R³⁰ other than the one constituting L are hydrogen.

式(HA)、式(HB)、式(HC)、式(HD)及式(HE)所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。就化合物的耐久性的观点而言，优选为至少一个氢被取代为氘的化合物，更优选为蒽环的氢全部由氘取代或全部的氢由氘取代，更优选为全部的氢由氘取代。At least one hydrogen in each of the compounds represented by Formula (HA), Formula (HB), Formula (HC), Formula (HD) and Formula (HE) may be substituted by a substituted silyl group, a cyano group, a halogen or a deuterium. From the viewpoint of the durability of the compound, it is preferably a compound in which at least one hydrogen is substituted by a deuterium, more preferably a compound in which all hydrogens of the anthracene ring are substituted by a deuterium or all hydrogens are substituted by a deuterium, and more preferably all hydrogens are substituted by a deuterium.

关于式(HA)、式(HB)、式(HC)、式(HD)及式(HE)中的各取代基等的优选范围，并无特别记载，针对所述情况，可参照式(H)中的相对应的取代基等的优选范围的记载。There is no particular description of the preferred range of each substituent in Formula (HA), Formula (HB), Formula (HC), Formula (HD) and Formula (HE). In such cases, reference may be made to the description of the preferred range of the corresponding substituent in Formula (H).

作为特别优选的式(H)所表示的蒽系化合物，可列举式(HA')、式(HB')、式(HC')、式(HD')或式(HE')所表示的蒽系化合物。Particularly preferred anthracene compounds represented by formula (H) include anthracene compounds represented by formula (HA′), formula (HB′), formula (HC′), formula (HD′), or formula (HE′).

在式(HA')、式(HB')、式(HC')、式(HD')及式(HE')中，R¹、R²、R³、R⁶、R⁷、R⁸、R⁹及R¹⁰分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除式(BO)所表示的化合物的任一氢而获得的一价基。In formula (HA'), formula (HB'), formula (HC'), formula (HD') and formula (HE'), R¹ , R² , R³ , R⁶ , R⁷ , R⁸ , R⁹ and R¹⁰ are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of the compound represented by formula (BO).

在式(HA')、式(HB')、式(HC')、式(HD')及式(HE')中，R²¹～R³⁰分别独立地为氢、碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R²¹～R³⁰中的邻接的基彼此可键结而形成碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢可由碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基取代。In formula (HA'), formula (HB'), formula (HC'), formula (HD') and formula (HE'), R²¹ to R³⁰ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

其中，R²¹～R³⁰的任意一个构成L。However, any one of R²¹ to R³⁰ constitutes L.

在式(HB')、式(HC')、式(HD')及式(HE')中，X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂，＞N-R、＞C(-R)₂及＞Si(-R)₂的R及式(HA')的R'分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，式(HA')的R'及作为X的＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结。所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基。In formula (HB'), formula (HC'), formula (HD') and formula (HE'), X is independently >O, >S, >NR, >C(-R)₂ or >Si(-R)₂ , R of >NR, >C(-R)₂ and >Si(-R)₂ and R' of formula (HA') are independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms, and R' of formula (HA') and R of >NR as X may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond. R of -C(-R)₂ - is alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms.

在式(HA')、式(HB')、式(HC')、式(HD')及式(HE')中，L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基。In formula (HA'), formula (HB'), formula (HC'), formula (HD') and formula (HE'), L is independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

式(HA')、式(HB')、式(HC')、式(HD')及式(HE')所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in each of the compounds represented by Formula (HA'), Formula (HB'), Formula (HC'), Formula (HD') and Formula (HE') may be substituted with a substituted silyl group, a cyano group, a halogen or a deuterium.

关于式(HA')、式(HB')、式(HC')、式(HD')及式(HE')中的各取代基等的优选范围，分别可参照式(HA)、式(HB)、式(HC)、式(HD)、式(HE)中的相对应的取代基等的优选范围的记载。特别是，在式(HA')、式(HB')、式(HC')及式(HE')中，R²¹～R³⁰优选为：构成L的一个以外的均为氢。其中，在式(HD')中，R²¹～R³⁰优选为：构成L的一个以外的任意一个为未经取代的碳数6～16的芳基，其他为氢。For the preferred ranges of the substituents in Formula (HA'), Formula (HB'), Formula (HC'), Formula (HD'), and Formula (HE'), reference can be made to the description of the preferred ranges of the corresponding substituents in Formula (HA'), Formula (HB'), Formula (HC'), Formula (HD'), and Formula (HE'). In particular, in Formula (HA'), Formula (HB'), Formula (HC'), and Formula (HE'), it is preferred that all of R²¹ to R³⁰ except one constituting L are hydrogen. In Formula (HD'), it is preferred that any one of R²¹ to R³⁰ except one constituting L is an unsubstituted aryl group having 6 to 16 carbon atoms, and the others are hydrogen.

另外，在式(HB')、式(HC')、式(HD')及式(HE')中，X分别独立地优选为＞O、＞N-R或＞C(-R)₂，所述＞N-R的R优选为碳数6～16的芳基，＞C(-R)₂的R优选为均为甲基，在式(HA')中，R'优选为碳数6～16的芳基，更优选为苯基。进而，在式(HA')、式(HB')、式(HC')、式(HD')及式(HE')中，L优选为单键或碳数6～10的亚芳基，更优选为单键。In formula (HB'), formula (HC'), formula (HD') and formula (HE'), X is each independently preferably >O, >NR or >C(-R)₂ , R of >NR is preferably an aryl group having 6 to 16 carbon atoms, and R of >C(-R)₂ is preferably a methyl group. In formula (HA'), R' is preferably an aryl group having 6 to 16 carbon atoms, and more preferably a phenyl group. Furthermore, in formula (HA'), formula (HB'), formula (HC'), formula (HD') and formula (HE'), L is preferably a single bond or an arylene group having 6 to 10 carbon atoms, and more preferably a single bond.

式(HA')、式(HB')、式(HC')、式(HD')及式(HE')所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。在式(HA')、式(HB')、式(HC')、式(HD')及式(HE')所表示的化合物各个中，就化合物的耐久性的观点而言，优选为至少一个氢被取代为氘的化合物，更优选为蒽环的氢全部由氘取代或全部的氢由氘取代，更优选为全部的氢由氘取代。At least one hydrogen in each of the compounds represented by Formula (HA'), Formula (HB'), Formula (HC'), Formula (HD') and Formula (HE') may be substituted with a substituted silyl group, a cyano group, a halogen or a deuterium. In each of the compounds represented by Formula (HA'), Formula (HB'), Formula (HC'), Formula (HD') and Formula (HE'), from the viewpoint of the durability of the compound, a compound in which at least one hydrogen is substituted with a deuterium is preferred, and a compound in which all hydrogens of the anthracene ring are substituted with a deuterium or all hydrogens are substituted with a deuterium is more preferred, and a compound in which all hydrogens are substituted with a deuterium is more preferred.

此外，在式(H)(优选为式(HA)、式(HB)、式(HC)、式(HD)或式(HE)，更优选为式(HA')、式(HB')、式(HC')、式(HD')或式(HE'))所表示的蒽系化合物中有时存在阿托异构体等，但作为式(H)所表示的蒽系化合物，可为能存在的任一异构体，另外，也可为这些异构体的任意混合比的混合物。In addition, in the anthracene compound represented by formula (H) (preferably formula (HA), formula (HB), formula (HC), formula (HD) or formula (HE), more preferably formula (HA'), formula (HB'), formula (HC'), formula (HD') or formula (HE')), atropisomers and the like sometimes exist, but the anthracene compound represented by formula (H) may be any isomer that can exist, and may also be a mixture of these isomers in any mixing ratio.

作为式(H)所表示的蒽系化合物的更具体的例子，可列举以下结构式所表示的化合物。As more specific examples of the anthracene-based compound represented by the formula (H), compounds represented by the following structural formulas can be mentioned.

此外，下述结构式中的“D”表示氘，“Me”表示甲基。In addition, "D" in the following structural formula represents deuterium, and "Me" represents a methyl group.

式(H)所表示的蒽系化合物可将在蒽部位的所期望的位置具有反应性基的化合物、与在包含X的多环结构部位具有反应性基的化合物作为起始原料，并应用铃木偶合、根岸偶合、其他现有的偶合反应来制造。作为这些反应性化合物的反应性基，可列举卤素或硼酸等。作为具体的制造方法，例如可参考国际公开第2014/141725号的段落[0089]～段落[0175]中的合成方法。另外，可参照美国专利公开第2015-001479号说明书中记载的方法来制造。The anthracene compound represented by formula (H) can use a compound having a reactive group at the desired position of the anthracene part and a compound having a reactive group at the polycyclic structure part containing X as starting materials, and apply Suzuki coupling, Negishi coupling, and other existing coupling reactions to manufacture. As the reactive groups of these reactive compounds, halogen or boric acid can be cited. As a specific manufacturing method, for example, the synthesis method in paragraphs [0089] to [0175] of International Publication No. 2014/141725 can be referred to. In addition, the method described in the specification of U.S. Patent Publication No. 2015-001479 can be referred to for manufacture.

2.作为式(D)所表示的单量体或具有多个式(D)所表示的部分结构的多聚体的多环芳香族化合物2. A polycyclic aromatic compound which is a monomer represented by formula (D) or a polymer having a plurality of partial structures represented by formula (D)

本发明的有机EL元件在发光层中包含作为下述式(D)所表示的单量体或具有多个下述式(D)所表示的部分结构的多聚体的多环芳香族化合物。所述多环芳香族化合物优选为作为掺杂剂材料而包含于发光层中。多环芳香族化合物优选为作为式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的单量体或具有多个式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的部分结构的多聚体的多环芳香族化合物。The organic EL element of the present invention contains a polycyclic aromatic compound in the light-emitting layer as a monomer represented by the following formula (D) or a polymer having a plurality of partial structures represented by the following formula (D). The polycyclic aromatic compound is preferably contained in the light-emitting layer as a dopant material. The polycyclic aromatic compound is preferably a polycyclic aromatic compound that is a monomer represented by formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f) or a polymer having a plurality of partial structures represented by formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f).

此外，在各结构式中，“A”～“C”及“a”～“c”分别为表示环、苯环或5元环所表示的环结构的符号，其他符号的定义与所述相同。In each structural formula, "A" to "C" and "a" to "c" are symbols representing a ring structure represented by a ring, a benzene ring or a 5-membered ring, respectively, and the definitions of other symbols are the same as described above.

式(D)中的A环、B环及C环分别独立地为芳基环或杂芳基环。这些环中的至少一个氢可由取代基取代。In formula (D), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted by a substituent.

优选为A环、B环及C环的至少任一个为具有至少一个取代基的芳基环或具有至少一个取代基的杂芳基环，更优选为A环、B环及C环均为具有至少一个取代基的芳基环或具有至少一个取代基的杂芳基环，进而优选为A环、B环及C环分别为具有一个取代基的芳基环或具有一个取代基的杂芳基环。It is preferred that at least any one of the A ring, the B ring and the C ring is an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, and it is more preferred that the A ring, the B ring and the C ring are all aryl rings having at least one substituent or heteroaryl rings having at least one substituent, and it is further preferred that the A ring, the B ring and the C ring are each an aryl ring having one substituent or a heteroaryl ring having one substituent.

作为此时的取代基，优选为经取代或未经取代的芳基、经取代或未经取代的杂芳基、经取代或未经取代的二芳基氨基、经取代或未经取代的二杂芳基氨基、经取代或未经取代的芳基杂芳基氨基(具有芳基与杂芳基的氨基)、经取代或未经取代的二芳基硼基(两个芳基可经由单键或连结基键结)、经取代或未经取代的烷基、经取代或未经取代的环烷基、经取代或未经取代的烷氧基、经取代或未经取代的芳氧基、或者取代硅烷基。作为这些基具有取代基时的取代基，可列举：芳基、杂芳基、烷基、环烷基、二芳基氨基、取代硅烷基。The substituent in this case is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having an aryl group and a heteroaryl group), a substituted or unsubstituted diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silyl group. When these groups have a substituent, the substituent includes an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a diarylamino group, and a substituted silyl group.

作为取代基，特别优选为经取代或未经取代的烷基(特别是新戊基)、金刚烷基之类的环烷基。另外，优选为叔烷基(tR)。原因在于：通过此种大体积的取代基而分子间距离增加，因此发光量子产率(photoluminescence quantum yield，PLQY)提高。另外，作为取代基，也优选为经取代或未经取代的二芳基氨基。As a substituent, a substituted or unsubstituted alkyl group (especially a neopentyl group) or a cycloalkyl group such as an adamantyl group is particularly preferred. In addition, a tertiary alkyl group (tR) is preferred. The reason is that the intermolecular distance increases due to such a bulky substituent, thereby improving the photoluminescence quantum yield (PLQY). In addition, as a substituent, a substituted or unsubstituted diarylamino group is also preferred.

所述叔烷基由下述式(tR)表示。The tertiary alkyl group is represented by the following formula (tR).

式(tR)中，R^a、R^b及R^c分别独立地为碳数1～24的烷基，所述烷基中的任意的-CH₂-可由-O-取代，式(tR)所表示的基在*处与式(D)所表示的化合物或结构中的至少一个氢进行取代。In formula (tR),^Ra ,^Rb and^Rc are independently alkyl groups having 1 to 24 carbon atoms, any_-CH2- in the alkyl group may be substituted by -O-, and the group represented by formula (tR) replaces at least one hydrogen atom in the compound or structure represented by formula (D) at position *.

R^a、R^b及R^c的“碳数1～24的烷基”可为直链及支链的任一种，例如可列举：碳数1～24的直链烷基或碳数3～24的支链烷基、碳数1～18的烷基(碳数3～18的支链烷基)、碳数1～12的烷基(碳数3～12的支链烷基)、碳数1～6的烷基(碳数3～6的支链烷基)、碳数1～4的烷基(碳数3～4的支链烷基)。The "alkyl group having 1 to 24 carbon atoms" for^Ra ,^Rb and^Rc may be any of a linear group and a branched group, and examples thereof include a linear group having 1 to 24 carbon atoms or a branched group having 3 to 24 carbon atoms, an alkyl group having 1 to 18 carbon atoms (a branched group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (a branched group having 3 to 4 carbon atoms).

式(D)的式(tR)中的R^a、R^b及R^c的碳数的合计优选为碳数3～20，特别优选为碳数3～10。The total number of carbon atoms of^Ra ,^Rb and^Rc in the formula (tR) of the formula (D) is preferably 3 to 20, and particularly preferably 3 to 10.

作为R^a、R^b及R^c的具体的烷基，可列举：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、正己基、1-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、正庚基、1-甲基己基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、2,6-二甲基-4-庚基、3,5,5-三甲基己基、正癸基、正十一基、1-甲基癸基、正十二基、正十三基、1-己基庚基、正十四基、正十五基、正十六基、正十七基、正十八基、正二十基等。Specific examples of the alkyl group for^Ra ,^Rb and^Rc include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an n-hexyl group, a 1-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, an n-heptyl group, a 1-methylhexyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, an n-nonyl group, a 2,2-dimethylheptyl group, a 2,6-dimethyl-4-heptyl group, a 3,5,5-trimethylhexyl group, an n-decyl group, an n-undecyl group, a 1-methyldecyl group, an n-dodecyl group, an n-tridecyl group, a 1-hexylheptyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group and an n-icosyl group.

作为式(tR)所表示的基，例如可列举：叔丁基、叔戊基、1-乙基-1-甲基丙基、1,1-二乙基丙基、1,1-二甲基丁基、1-乙基-1-甲基丁基、1,1,3,3-四甲基丁基、1,1,4-三甲基戊基、1,1,2-三甲基丙基、1,1-二甲基辛基、1,1-二甲基戊基、1,1-二甲基庚基、1,1,5-三甲基己基、1-乙基-1-甲基己基、1-乙基-1,3-二甲基丁基、1,1,2,2-四甲基丙基、1-丁基-1-甲基戊基、1,1-二乙基丁基、1-乙基-1-甲基戊基、1,1,3-三甲基丁基、1-丙基-1-甲基戊基、1,1,2-三甲基丙基、1-乙基-1,2,2-三甲基丙基、1-丙基-1-甲基丁基、1,1-二甲基己基等。这些中，优选为叔丁基及叔戊基。Examples of the group represented by the formula (tR) include a tert-butyl group, a tert-amyl group, a 1-ethyl-1-methylpropyl group, a 1,1-diethylpropyl group, a 1,1-dimethylbutyl group, a 1-ethyl-1-methylbutyl group, a 1,1,3,3-tetramethylbutyl group, a 1,1,4-trimethylpentyl group, a 1,1,2-trimethylpropyl group, a 1,1-dimethyloctyl group, a 1,1-dimethylpentyl group, a 1,1-dimethylheptyl group, a 1,1,5-trimethylhexyl group, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, tert-butyl and tert-pentyl are preferred.

作为A环、B环及C环中的取代基的其他的优选例，例如可列举由式(tR)的基取代的二芳基氨基、由式(tR)的基取代的咔唑基或由式(tR)的基取代的苯并咔唑基。关于“二芳基氨基”，可列举作为下述“第一取代基”而说明的基。作为针对二芳基氨基、咔唑基及苯并咔唑基的式(tR)的基的取代形态，可列举这些基中的芳基环或苯环的一部分或全部的氢由式(tR)的基取代的例子。As other preferred examples of substituents in the A ring, the B ring and the C ring, for example, a diarylamino group substituted by a group of formula (tR), a carbazolyl group substituted by a group of formula (tR) or a benzocarbazolyl group substituted by a group of formula (tR) can be cited. Regarding the "diarylamino group", the groups described as the "first substituent" below can be cited. As substitution forms of the groups of formula (tR) for the diarylamino group, the carbazolyl group and the benzocarbazolyl group, examples can be cited in which a part or all of the hydrogen of the aryl ring or the benzene ring in these groups is replaced by a group of formula (tR).

A环、B环及C环中的芳基环或杂芳基环优选为具有与包含B(硼)、X¹及X²的式(D)中央的缩合二环结构共有键结的5元环或6元环。The aryl ring or heteroaryl ring in the A ring, the B ring and the C ring preferably has a 5-membered ring or a 6-membered ring which shares a bond with the central condensed bicyclic structure of the formula (D) containing B (boron),^X1 and^X2 .

此处，所谓“缩合二环结构”，是指式(D)的中央所示的包含B(硼)、X¹及X²而构成的两个饱和烃环缩合而成的结构。另外，所谓“与缩合二环结构共有键结的6元环”，是指在所述缩合二环结构中缩合的6元环(例如苯环)。另外，所谓“(作为A环的)芳基环或杂芳基环具有所述6元环”，是指仅由所述6元环形成A环、或以包含所述6元环的方式在所述6元环中进而缩合其他环等来形成A环。换句话说，所谓此处所述的“具有6元环的(作为A环的)芳基环或杂芳基环”，是指构成A环的全部或一部分的6元环在所述缩合二环结构中缩合。关于“B环”、“C环”及“5元环”，相同的说明也适用。Here, the so-called "condensed bicyclic structure" refers to a structure formed by condensation of two saturated hydrocarbon rings composed of B (boron),^X1 and^X2 shown in the center of formula (D). In addition, the so-called "6-membered ring shared with the condensed bicyclic structure" refers to the 6-membered ring (such as a benzene ring) condensed in the condensed bicyclic structure. In addition, the so-called "aryl ring or heteroaryl ring (as A ring) has the 6-membered ring" means that the A ring is formed only by the 6-membered ring, or other rings are further condensed in the 6-membered ring in a manner including the 6-membered ring to form the A ring. In other words, the so-called "aryl ring or heteroaryl ring (as A ring) having a 6-membered ring" mentioned here means that all or part of the 6-membered rings constituting the A ring are condensed in the condensed bicyclic structure. The same description also applies to "B ring", "C ring" and "5-membered ring".

式(D)中的A环对应于式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中的a环与其取代基R¹～取代基R³。式(D)中的B环对应于式(D-a)、式(D-b)及式(D-c)中的b环与其取代基R⁸～取代基R¹¹、式(D-d)中的b环与其取代基R¹⁰及取代基R¹¹、以及式(D-e)及式(D-f)中的b环与其取代基R⁸及取代基R⁹。式(D)中的C环对应于式(D-a)中的c环与其取代基R⁴～取代基R⁷、式(D-b)、式(D-d)及式(D-f)中的c环与其取代基R⁴及取代基R⁵、以及式(D-c)及式(D-e)中的c环与其取代基R⁶及取代基R⁷。即，式(D-a)对应于选择至少具有6元环结构的环作为式(D)的A环～C环的结构，式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)分别对应于选择至少具有6元环结构的环及至少具有5元环结构的环作为式(D)的A环～C环的结构。以所述含义，由小写字母a～c来表示式(D-a)的各环。The A ring in the formula (D) corresponds to the a ring and its substituents R¹ to R 3 in the formula (Da), the formula (Db), the formula (Dc), the formula (Dd), the formula (De), and the formula (Df). The B ring in the formula (^D ) corresponds to the b ring and its substituents R⁸ to R¹¹ in the formula (Da), the b ring and its substituents R¹⁰ and R¹¹ in the formula (Dd), and the b ring and its substituents R⁸ and R⁹ in the formula (De) and the formula (Df). The C ring in the formula (D) corresponds to the c ring and its substituents R⁴ to R⁷ in the formula (Da), the c ring and its substituents R⁴ and R⁵ in the formula (Db), the formula (Dd), and the formula (Df), and the c ring and its substituents R⁶ and R⁷ in the formula (Dc) and the formula (De). That is, formula (Da) corresponds to a structure in which a ring having at least a 6-membered ring structure is selected as ring A to ring C of formula (D), and formulas (Db), (Dc), (Dd), (De), and (Df) correspond to structures in which a ring having at least a 6-membered ring structure and a ring having at least a 5-membered ring structure are selected as ring A to ring C of formula (D), respectively. In the above meaning, each ring of formula (Da) is represented by lowercase letters a to c.

式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中的X_X分别独立地为＞O、＞S、＞N-R或＞C(-R)₂。此处，所述＞N-R的R为可经取代的芳基、可经取代的杂芳基、可经取代的烷基或可经取代的环烷基，优选为可经取代的芳基，更优选为未经取代的芳基。另外，所述＞C(-R)₂的R分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，优选为烷基，更优选为甲基。＞C(-R)₂中的两个R优选为相同。另外，＞C(-R)₂中的两个R也优选为相互键结而形成环。_XX in formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df) are each independently >O, >S, >NR or >C(-R)_2. Here, R of the >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted or a cycloalkyl group which may be substituted, preferably an aryl group which may be substituted, and more preferably an unsubstituted aryl group. In addition, R of the >C(-R)₂ are each independently hydrogen, an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, preferably an alkyl group, and more preferably a methyl group. The two R in >C(-R)₂ are preferably the same. In addition, the two R in >C(-R)₂ are also preferably bonded to each other to form a ring.

X_X分别独立地优选为＞O、＞S或＞N-R，更优选为＞O或＞S，进而优选为＞S。_XX each independently represents preferably >O, >S or >NR, more preferably >O or >S, and still more preferably >S.

在式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中，R¹～R¹¹分别独立地为氢、芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、二芳基硼基(两个芳基可经由单键或连结基键结)、烷基、环烷基、烷氧基、芳氧基或取代硅烷基，它们中的至少一个氢可由芳基、杂芳基、烷基、环烷基或取代硅烷基取代。In formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df), R¹ to R¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, and at least one hydrogen among them may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl.

R¹～R¹¹分别独立地优选为氢、烷基(特别是所述叔烷基(tR)、新戊基等)、环烷基(例如金刚烷基等)、经取代或未经取代的二芳基氨基、或者取代硅烷基(三苯基硅烷基、三甲基硅烷基等)。R¹ to R¹¹ are each independently preferably hydrogen, alkyl (particularly the tertiary alkyl (tR) and neopentyl), cycloalkyl (for example, adamantyl), substituted or unsubstituted diarylamino, or substituted silyl (triphenylsilyl, trimethylsilyl).

优选为：式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中的R¹～R³中，0个～1个为氢以外的基(特别是所述优选的取代基)且其他为氢，R⁴～R⁷中，0个～1个为氢以外的基(特别是所述优选的取代基)且其他为氢，R⁸～R¹¹中，0个～1个为氢以外的基(特别是所述优选的取代基)且其他为氢，Preferably, among R¹ to R³ in formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df), 0 to 1 of them are groups other than hydrogen (especially the preferred substituents described above) and the others are hydrogen, among R⁴ to R⁷ , 0 to 1 of them are groups other than hydrogen (especially the preferred substituents described above) and the others are hydrogen, and among R⁸ to R¹¹ , 0 to 1 of them are groups other than hydrogen (especially the preferred substituents described above) and the others are hydrogen,

更优选为：R¹～R³中，1个为氢以外的基(特别是所述优选的取代基)且其他为氢，R⁴～R⁷中，1个为氢以外的基(特别是所述优选的取代基)且其他为氢，R⁸～R¹¹中，1个为氢以外的基(特别是所述优选的取代基)且其他为氢。More preferably, among R¹ to R³ , one is a group other than hydrogen (especially the preferred substituent described above) and the others are hydrogen, among R⁴ to R⁷ , one is a group other than hydrogen (especially the preferred substituent described above) and the others are hydrogen, and among R⁸ to R¹¹ , one is a group other than hydrogen (especially the preferred substituent described above) and the others are hydrogen.

在式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中，a环、b环及c环的取代基R¹～取代基R¹¹中的邻接的基彼此可键结并与a环、b环或c环一起形成芳基环或杂芳基环，所形成的环中的至少一个氢可由芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、二芳基硼基(两个芳基可经由单键或连结基键结)、烷基、环烷基、烷氧基、芳氧基、三烷基硅烷基、三环烷基硅烷基、二烷基环烷基硅烷基或烷基二环烷基硅烷基取代，它们中的至少一个氢可由芳基、杂芳基、烷基或环烷基取代。因此，关于式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)所表示的多环芳香族化合物，根据a环、b环及c环中的取代基的相互的键结形态，构成化合物的环结构发生变化。例如，关于式(D-a)所表示的多环芳香族化合物，例如如下述式(D-a-1)及式(D-a-2)所示，构成化合物的环结构发生变化。各式中的A'环、B'环及C'环分别对应于式(D)中的A环、B环及C环。In formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df), adjacent groups among substituents R¹ to R¹¹ of ring a, ring b and ring c may be bonded to each other and form an aryl ring or a heteroaryl ring together with ring a, ring b or ring c, and at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group or an alkyldicycloalkylsilyl group, and at least one hydrogen in these groups may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group. Therefore, regarding the polycyclic aromatic compounds represented by formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df), the ring structure constituting the compound changes according to the mutual bonding form of the substituents in the a ring, b ring and c ring. For example, regarding the polycyclic aromatic compound represented by formula (Da), the ring structure constituting the compound changes as shown in the following formulas (Da-1) and (Da-2). The A' ring, B' ring and C' ring in each formula correspond to the A ring, B ring and C ring in formula (D), respectively.

若以式(D-a)进行说明，则所述式(D-a-1)及式(D-a-2)中的A'环、B'环及C'环表示取代基R¹～取代基R¹¹中的邻接的基彼此键结并分别与a环、b环及c环一起形成的芳基环或杂芳基环(也可称为其他环结构在a环、b环或c环中缩合而成的稠环)。此外，虽然式中未示出，但也存在a环、b环及c环全部变化成A'环、B'环及C'环的化合物。另外，如根据所述式(D-a-1)及式(D-a-2)而可知，例如式(D-a)中的b环的R⁸与c环的R⁷、b环的R¹¹与a环的R¹、c环的R⁴与a环的R³等并不符合“邻接的基彼此”，只要无特别说明，则它们不会进行键结。即，所谓“邻接的基”，是指在同一环上邻接的基。If the formula (Da) is used for explanation, the A' ring, B' ring and C' ring in the formula (Da-1) and the formula (Da-2) represent the aryl ring or heteroaryl ring formed by the adjacent groups in the substituents R¹ to R¹¹ bonded to each other and respectively formed with the a ring, the b ring and the c ring (it can also be called a condensed ring formed by condensation of other ring structures in the a ring, the b ring or the c ring). In addition, although not shown in the formula, there are compounds in which the a ring, the b ring and the c ring are all changed to the A' ring, the B' ring and the C' ring. In addition, as can be seen from the formula (Da-1) and the formula (Da-2), for example, R⁸ of the b ring and R⁷ of the c ring, R¹¹ of the b ring and R¹ of the a ring, R⁴ of the c ring and R³ of the a ring in the formula (Da) do not meet the "adjacent groups to each other", and unless otherwise specified, they will not be bonded. That is, the "adjacent groups" refer to groups that are adjacent to each other on the same ring.

所述式(D-a-1)或式(D-a-2)所表示的化合物例如为具有苯环、吲哚环、吡咯环、呋喃环、噻吩环、苯并呋喃环、苯并噻吩环、环戊二烯环或茚环对于作为a环(或b环或c环)的苯环进行缩合而形成的A'环(或B'环或C'环)的化合物，所形成的稠环A'(或稠环B'或稠环C')分别为萘环、咔唑环、吲哚环、苯并呋喃环、苯并噻吩环、二苯并呋喃环、二苯并噻吩环、茚环或芴环。The compound represented by the formula (D-a-1) or (D-a-2) is, for example, a compound having a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclopentadiene ring or an indene ring, and the benzene ring as the a ring (or the b ring or the c ring) is condensed to form an A' ring (or a B' ring or a C' ring), and the formed condensed ring A' (or a condensed ring B' or a condensed ring C') is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring or a fluorene ring, respectively.

另外，在式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中，也可分别同样地形成其他环结构在a环、b环或c环中进行缩合而成的稠环。例如，作为a环或b环的苯环可与所述式(D-a)中的苯环同样地与其他环结构进行缩合而形成稠环。In addition, in formula (D-b), formula (D-c), formula (D-d), formula (D-e) and formula (D-f), other ring structures may be condensed in ring a, ring b or ring c to form a condensed ring. For example, the benzene ring as ring a or ring b may be condensed with other ring structures to form a condensed ring in the same manner as the benzene ring in formula (D-a).

在式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中，特别优选为在作为b环或c环的5元环中，R⁴～R¹¹中的邻接的基彼此键结而形成环从而形成稠环。例如，在式(D-b)及式(D-c)的c环以及式(D-d)、式(D-e)及式(D-f)的b环及c环中，R³～R¹¹中的邻接的基彼此键结而形成环，由此可形成作为稠环的B'环或C'环。作为所形成的环为苯环时的稠环的例子，可列举：吲哚环、苯并呋喃环、苯并噻吩环。In Formula (Db), Formula (Dc), Formula (Dd), Formula (De) and Formula (Df), it is particularly preferred that in the 5-membered ring as the b-ring or the c-ring, the adjacent groups among R⁴ to R¹¹ are bonded to each other to form a ring to form a condensed ring. For example, in the c-ring of Formula (Db) and Formula (Dc) and the b-ring and c-ring of Formula (Dd), Formula (De) and Formula (Df), the adjacent groups among R³ to R¹¹ are bonded to each other to form a ring, thereby forming a B' ring or C' ring as a condensed ring. Examples of condensed rings when the formed ring is a benzene ring include an indole ring, a benzofuran ring, and a benzothiophene ring.

作为一例，以下示出在作为式(D-b)的c环的5元环中，R⁴及R⁵彼此键结而形成苯环从而形成稠环的例子。As an example, the following shows an example in which^R4 and^R5 are bonded to each other to form a benzene ring in the 5-membered ring as the c ring of formula (Db) to form a condensed ring.

式(D-b-1)中，R¹、R²、R³、R⁸、R⁹、R¹⁰、R¹¹、X_X、X¹及X²的含义与式(D-b)中的各个相同，优选范围也相同。R^4b、R^5b、R^6b、R^7b为氢或选自由芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、二芳基硼基(两个芳基可经由单键或连结基键结)、烷基、环烷基、烷氧基、芳氧基及取代硅烷基所组成的群组中的取代基，这些取代基中的至少一个氢可由芳基、杂芳基、烷基、环烷基或取代硅烷基取代。R^4b、R^5b、R^6b、R^7b中，优选为0个～2个为氢以外的取代基且其他为氢，更优选为1个为氢以外的取代基且其他为氢。关于氢以外的取代基，优选范围可参照作为第一取代基(可具有第二取代基)而后述的取代基的记载。作为氢以外的取代基，特别优选为烷基(特别是所述叔烷基(tR)、新戊基等)、环烷基(例如金刚烷基等)、或者经取代或未经取代的二芳基氨基。In formula (Db-1), R¹ , R² , R³ , R⁸ , R⁹ , R¹⁰ , R¹¹ ,_XX , X¹ and X² have the same meanings as those in formula (Db), and the preferred ranges are also the same. R^4b , R^5b , R^6b , and R^7b are hydrogen or a substituent selected from the group consisting of an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, and a substituted silyl group, and at least one hydrogen in these substituents may be substituted by an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, or a substituted silyl group. Among R^4b , R^5b , R^6b , and R^7b , preferably 0 to 2 are substituents other than hydrogen and the others are hydrogen, and more preferably 1 is a substituent other than hydrogen and the others are hydrogen. Regarding the substituents other than hydrogen, the preferred range can refer to the description of the substituents described later as the first substituent (which may have a second substituent). As the substituents other than hydrogen, alkyl groups (especially the tertiary alkyl group (tR), neopentyl group, etc.), cycloalkyl groups (such as adamantyl group, etc.), or substituted or unsubstituted diarylamino groups are particularly preferred.

例如，在式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中，例如，当X_X为＞O时，b环或c环成为呋喃环，但与苯环对于所述呋喃环进行缩合而形成的式(D-a-1)的B'环或C'环相对应的环为苯并呋喃环。For example, in formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df), when_XX is >0, the b ring or c ring becomes a furan ring, but the ring corresponding to the B' ring or C' ring of formula (Da-1) formed by condensing the benzene ring with the furan ring is a benzofuran ring.

另外，例如，在式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中，例如，当X_X为＞S时，b环或c环成为噻吩环，但与苯环对于所述噻吩环进行缩合而形成的式(D-a-1)的B'环或C'环相对应的环为苯并噻吩环。In addition, for example, in formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df), when_XX is >S, the b ring or c ring becomes a thiophene ring, but the ring corresponding to the B' ring or C' ring of formula (Da-1) formed by condensing the benzene ring with the thiophene ring is a benzothiophene ring.

式(D)中的X¹及X²分别独立地为＞O、＞C(-R)₂或＞N-R。式(D)中的X¹及X²优选为至少任一个为＞N-R，更优选为均为＞N-R或X¹及X²的任意其中一个为＞N-R且另一个为＞C(-R)₂，最优选为均为＞N-R。^X1 and^X2 in formula (D) are each independently >O, >C(-R)₂ or >NR. It is preferred that at least one of^X1 and^X2 in formula (D) is >NR, more preferably both are >NR, or either one of^X1 and^X2 is >NR and the other is >C(-R)₂ , and most preferably both are >NR.

X¹及X²中的＞C(-R)₂的R分别独立地为可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基。＞C(-R)₂中的两个R优选为相同，而且，两个R可键结而形成环。作为此种化合物，可列举下述化合物(D-303)之类的化合物。R in >C(-R)₂ in^X1 and^X2 is independently an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group. The two R in >C(-R)₂ are preferably the same, and the two R may be bonded to form a ring. Examples of such compounds include the following compound (D-303).

X¹及X²中的＞N-R的R为可经取代的芳基(其中，作为取代基，优选为氨基除外)、可经取代的杂芳基、可经取代的烷基或可经取代的环烷基。R of >NR in^X1 and^X2 is an optionally substituted aryl group (preferably excluding an amino group as a substituent), an optionally substituted heteroaryl group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group.

X¹及X²中的＞N-R的R优选为可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～12的芳基或者碳数1～6的烷基，优选为可由碳数1～5的烷基取代的碳数6～12的芳基，进而优选为可经取代的苯基，进而优选为可经取代的邻联苯基(相对于N在邻位具有苯基的苯基)。特别优选为X¹及X²中的＞N-R仅任意一个为邻联苯基。作为此种化合物，可列举下述的化合物(D-202)之类的化合物。R of >NR in^X1 and^X2 is preferably an aryl group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or an alkyl group having 1 to 6 carbon atoms, preferably an aryl group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms, more preferably an optionally substituted phenyl group, and more preferably an optionally substituted ortho-biphenyl group (a phenyl group having a phenyl group at an ortho position relative to N). It is particularly preferred that only one of >NR in^X1 and^X2 is an ortho-biphenyl group. Examples of such compounds include the following compound (D-202).

X¹及X²中的＞N-R中的R可通过连结基或单键而与所述A环、B环及C环的至少一个环键结。作为连结基，优选为-O-、-S-或-C(-R)₂-。此外，所述“-C(-R)₂-”的R为氢、烷基或环烷基。所述规定例如可由如下的化合物来表现，所述化合物由下述式(D-a-3-1)表示、且具有X¹或X²被导入至稠环B'及稠环C'中的环结构。即，例如为具有其他环以导入X¹(或X²)的方式对于作为式(D-a)中的b环(或c环)的苯环进行缩合而形成的B'环(或C'环)的化合物。所形成的稠环B'(或稠环C')例如为咔唑环、吩噁嗪环、吩噻嗪环或吖啶环。R in the "＞NR" in^X1 and^X2 may be bonded to at least one of the A ring, B ring and C ring via a linking group or a single bond. As the linking group, -O-, -S- or -C(-R)_2- is preferred. In addition, R in "-C(-R)_2- " is hydrogen, alkyl or cycloalkyl. The above provisions may be represented, for example, by a compound represented by the following formula (Da-3-1) and having a ring structure in which^X1 or^X2 is introduced into the condensed ring B' and the condensed ring C'. That is, for example, a compound having a B' ring (or C' ring) formed by condensing the benzene ring as the b ring (or c ring) in the formula (Da) with another ring in a manner of introducing^X1 (or^X2 ). The formed condensed ring B' (or condensed ring C') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring or an acridine ring.

另外，所述规定也可由如下的化合物来表现，所述化合物由下述式(D-a-3-2)或式(D-a-3-3)表示、且具有X¹和/或X²被导入至稠环A'中的环结构。即，例如为具有其他环以导入X¹(和/或X²)的方式对于作为式(D-a)中的a环的苯环进行缩合而形成的A'环的化合物。所形成的稠环A'例如为咔唑环、吩噁嗪环、吩噻嗪环或吖啶环。In addition, the above-mentioned provisions can also be expressed by a compound represented by the following formula (Da-3-2) or formula (Da-3-3) and having a ring structure in which^X1 and/or^X2 are introduced into a condensed ring A'. That is, for example, a compound having an A' ring formed by condensing the benzene ring as the a ring in formula (Da) with another ring in such a manner as to introduce^X1 (and/or^X2 ). The formed condensed ring A' is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring or an acridine ring.

式(D)的B环与C环或者式(D-a)的b环与c环可通过表示为Xz的连结基或单键而键结。作为此种形态，可列举式(D-a-7-1)或式(D-a-7-2)的形态。作为连结基，优选为-O-、-S-或-C(-R)₂-。此外，所述“-C(-R)₂-”的R为氢、烷基或环烷基，两个R可形成环。The B ring and the C ring of formula (D) or the b ring and the c ring of formula (Da) may be bonded via a linking group represented by Xz or a single bond. Such a form may include the form of formula (Da-7-1) or formula (Da-7-2). As the linking group, -O-, -S- or -C(-R)₂ - is preferred. In addition, R of "-C(-R)₂ -" is hydrogen, alkyl or cycloalkyl, and two Rs may form a ring.

作为式(D)的A环、B环及C环的“芳基环”例如可列举碳数6～30的芳基环，优选为碳数6～16的芳基环，更优选为碳数6～12的芳基环，特别优选为碳数6～10的芳基环。Examples of the "aryl ring" of Ring A, Ring B and Ring C in Formula (D) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms.

作为具体的“芳基环”，可列举：作为单环系的苯环，作为二环系的联苯环，作为缩合二环系的萘环、茚环，作为三环系的三联苯环(间三联苯基、邻三联苯基、对三联苯基)，作为缩合三环系的苊环、芴环、非那烯环、菲环，作为缩合四环系的三亚苯环、芘环、并四苯环，作为缩合五环系的苝环、并五苯环等。Specific examples of the "aryl ring" include: a benzene ring as a monocyclic ring system, a biphenyl ring as a bicyclic ring system, a naphthalene ring and an indene ring as a condensed bicyclic ring system, a terphenyl ring (meta-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic ring system, an acenaphthene ring, a fluorene ring, a phenanthren ring and a phenanthrene ring as a condensed tricyclic ring system, a triphenylene ring, a pyrene ring and a tetracene ring as a condensed tetracyclic ring system, a perylene ring and a pentacene ring as a condensed pentacyclic ring system, and the like.

作为式(D)的A环、B环及C环的“杂芳基环”例如可列举碳数2～30的杂芳基环，优选为碳数2～25的杂芳基环，更优选为碳数2～20的杂芳基环，进而优选为碳数2～15的杂芳基环，特别优选为碳数2～10的杂芳基环。另外，作为“杂芳基环”，例如可列举除碳以外含有1个至5个选自氧、硫及氮中的杂原子作为环构成原子的杂环等。此外，所述“杂芳基环”对应于式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中的包含X_X的5元环或者式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中所规定的“R¹～R¹¹中的邻接的基彼此键结并与a环、b环或c环一起形成的杂芳基环”。Examples of the "heteroaryl ring" of the A ring, B ring and C ring of formula (D) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. In addition, examples of the "heteroaryl ring" include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms other than carbon. In addition, the "heteroaryl ring" corresponds to a 5-membered ring containing_XX in formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df) or "a heteroaryl ring formed by adjacent groups in R¹ to R¹¹ bonding to each other and together with ring a, ring b or ring c" as specified in formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De) and formula (Df).

作为具体的“杂芳基环”，例如可列举：吡咯环、噁唑环、异噁唑环、噻唑环、异噻唑环、咪唑环、噁二唑环、噻二唑环、三唑环、四唑环、吡唑环、吡啶环、嘧啶环、哒嗪环、吡嗪环、三嗪环、吲哚环、异吲哚环、1H-吲唑环、苯并咪唑环、苯并噁唑环、苯并噻唑环、1H-苯并三唑环、喹啉环、异喹啉环、噌啉环、喹唑啉环、喹噁啉环、酞嗪环、萘啶环、嘌呤环、蝶啶环、咔唑环、吖啶环、吩噁噻环、吩噁嗪环、吩噻嗪环、吩嗪环、吩吖硅(phenazasiline)环、吲嗪环、呋喃环、苯并呋喃环、异苯并呋喃环、二苯并呋喃环、噻吩环、苯并噻吩环、二苯并噻吩环、呋咱环、噻蒽环、吲哚并咔唑环、苯并吲哚并咔唑环、苯并苯并吲哚并咔唑环、萘并苯并呋喃环等。Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, Phthaliazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiol ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazasiline ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, thianthracene ring, indolecarbazole ring, benzindolecarbazole ring, benzobenzoindolecarbazole ring, naphthobenzofuran ring, etc.

所述“芳基环”或“杂芳基环”中的至少一个氢可由作为第一取代基的、经取代或未经取代的“芳基”、经取代或未经取代的“杂芳基”、经取代或未经取代的“二芳基氨基”、经取代或未经取代的“二杂芳基氨基”、经取代或未经取代的“芳基杂芳基氨基”、经取代或未经取代的“二芳基硼基(两个芳基可经由单键或连结基键结)”、经取代或未经取代的“烷基”、经取代或未经取代的“环烷基”、经取代或未经取代的“烷氧基”、经取代或未经取代的“芳氧基”、或者经取代的“硅烷基”取代，但作为所述第一取代基的“芳基”或“杂芳基”、“二芳基氨基”的芳基、“二杂芳基氨基”的杂芳基、“芳基杂芳基氨基”的芳基与杂芳基、“二芳基硼基”的芳基以及“芳氧基”的芳基可列举所述“芳基环”或“杂芳基环”的一价基。At least one hydrogen in the “aryl ring” or “heteroaryl ring” may be replaced by a substituted or unsubstituted “aryl”, a substituted or unsubstituted “heteroaryl”, a substituted or unsubstituted “diarylamino”, a substituted or unsubstituted “diheteroarylamino”, a substituted or unsubstituted “arylheteroarylamino”, a substituted or unsubstituted “diarylboryl (two aryl groups may be bonded via a single bond or a linking group)”, a substituted or unsubstituted “alkyl”, The first substituent may be a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silyl group, but the aryl group or heteroaryl group as the first substituent group may include a monovalent group of the aforementioned “aryl ring” or “heteroaryl ring”, an aryl group of a “diarylamino group”, a heteroaryl group of a “diheteroarylamino group”, an aryl group and a heteroaryl group of an “arylheteroarylamino group”, an aryl group of a “diarylboryl group”, and an aryl group of an “aryloxy group”.

另外，作为第一取代基的“烷基”可为直链及支链的任一种，例如可列举碳数1～24的直链烷基或碳数3～24的支链烷基。优选为碳数1～18的烷基(碳数3～18的支链烷基)，更优选为碳数1～12的烷基(碳数3～12的支链烷基)，进而优选为碳数1～8的烷基(碳数3～8的支链烷基)，特别优选为碳数1～6的烷基(碳数3～6的支链烷基)，最优选为碳数1～5的烷基(碳数3～5的支链烷基)。In addition, the "alkyl" as the first substituent may be any of a linear chain and a branched chain, and examples thereof include a linear chain alkyl group having 1 to 24 carbon atoms and a branched chain alkyl group having 3 to 24 carbon atoms. Preferably, it is an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms), more preferably, it is an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), further preferably, it is an alkyl group having 1 to 8 carbon atoms (a branched chain alkyl group having 3 to 8 carbon atoms), particularly preferably, it is an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), and most preferably, it is an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms).

作为具体的烷基，可列举：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基(t-pentyl)(t-amyl)、正己基、1-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、正庚基、1-甲基己基、正辛基、叔辛基(1,1,3,3-四甲基丁基)、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、2,6-二甲基-4-庚基、3,5,5-三甲基己基、正癸基、正十一基、1-甲基癸基、正十二基、正十三基、1-己基庚基、正十四基、正十五基、正十六基、正十七基、正十八基、正二十基等。Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-icosyl.

另外，例如还可列举：1-乙基-1-甲基丙基、1,1-二乙基丙基、1,1-二甲基丁基、1-乙基-1-甲基丁基、1,1,4-三甲基戊基、1,1,2-三甲基丙基、1,1-二甲基辛基、1,1-二甲基戊基、1,1-二甲基庚基、1,1,5-三甲基己基、1-乙基-1-甲基己基、1-乙基-1,3-二甲基丁基、1,1,2,2-四甲基丙基、1-丁基-1-甲基戊基、1,1-二乙基丁基、1-乙基-1-甲基戊基、1,1,3-三甲基丁基、1-丙基-1-甲基戊基、1,1,2-三甲基丙基、1-乙基-1,2,2-三甲基丙基、1-丙基-1-甲基丁基、1,1-二甲基己基等。Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like can be mentioned.

另外，作为第一取代基的“环烷基”可列举碳数3～24的环烷基、碳数3～20的环烷基、碳数3～16的环烷基、碳数3～14的环烷基、碳数5～10的环烷基、碳数5～8的环烷基、碳数5～6的环烷基、碳数5的环烷基等。In addition, examples of the "cycloalkyl" as the first substituent include cycloalkyl groups having 3 to 24 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 16 carbon atoms, cycloalkyl groups having 3 to 14 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, cycloalkyl groups having 5 to 8 carbon atoms, cycloalkyl groups having 5 to 6 carbon atoms, and cycloalkyl groups having 5 carbon atoms.

作为具体的环烷基，可列举：环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基及它们的碳数1～5的烷基(特别是甲基)取代物、或者降冰片烯基、双环[1.0.1]丁基、双环[1.1.1]戊基、双环[2.0.1]戊基、双环[1.2.1]己基、双环[3.0.1]己基、双环[2.1.2]庚基、双环[2.2.2]辛基、金刚烷基、二金刚烷基、十氢萘基、十氢薁基等。Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl and C1-5 alkyl (particularly methyl)-substituted groups thereof, norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl and decahydroazulyl.

另外，作为第一取代基的“烷氧基”例如可列举碳数1～24的直链的烷氧基或碳数3～24的支链的烷氧基。优选为碳数1～18的烷氧基(碳数3～18的支链的烷氧基)，更优选为碳数1～12的烷氧基(碳数3～12的支链的烷氧基)，进而优选为碳数1～6的烷氧基(碳数3～6的支链的烷氧基)，特别优选为碳数1～5的烷氧基(碳数3～5的支链的烷氧基)。In addition, examples of the "alkoxy group" as the first substituent include a linear alkoxy group having 1 to 24 carbon atoms or a branched alkoxy group having 3 to 24 carbon atoms. An alkoxy group having 1 to 18 carbon atoms (a branched alkoxy group having 3 to 18 carbon atoms) is preferred, an alkoxy group having 1 to 12 carbon atoms (a branched alkoxy group having 3 to 12 carbon atoms) is more preferred, an alkoxy group having 1 to 6 carbon atoms (a branched alkoxy group having 3 to 6 carbon atoms) is further preferred, and an alkoxy group having 1 to 5 carbon atoms (a branched alkoxy group having 3 to 5 carbon atoms) is particularly preferred.

作为具体的烷氧基，可列举：甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、叔戊氧基、戊氧基、己氧基、庚氧基、辛氧基等。Specific examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a tert-pentyloxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, and an octyloxy group.

另外，作为第一取代基的“取代硅烷基”例如可列举由选自由烷基、环烷基及芳基所组成的群组中的三个取代基取代的硅烷基。例如可列举：三烷基硅烷基、三环烷基硅烷基、二烷基环烷基硅烷基、烷基二环烷基硅烷基、三芳基硅烷基、二烷基芳基硅烷基及烷基二芳基硅烷基。In addition, the "substituted silyl group" as the first substituent group may be, for example, a silyl group substituted with three substituents selected from the group consisting of an alkyl group, a cycloalkyl group, and an aryl group. Examples thereof include a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a triarylsilyl group, a dialkylarylsilyl group, and an alkyldiarylsilyl group.

作为“三烷基硅烷基”，可列举硅烷基中的三个氢分别独立地由烷基取代的基，所述烷基可引用所述作为第一取代基中的“烷基”而说明的基。对于取代而言优选的烷基为碳数1～5的烷基，具体而言，可列举：甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、叔戊基等。As the "trialkylsilyl group", there can be mentioned a group in which three hydrogen atoms in the silyl group are independently replaced by an alkyl group, and the alkyl group can be the group described as the "alkyl group" in the first substituent. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specifically, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, tert-amyl, etc. can be mentioned.

作为具体的三烷基硅烷基，可列举：三甲基硅烷基、三乙基硅烷基、三丙基硅烷基、三异丙基硅烷基、三丁基硅烷基、三仲丁基硅烷基、三叔丁基硅烷基、三叔戊基硅烷基、乙基二甲基硅烷基、丙基二甲基硅烷基、异丙基二甲基硅烷基、丁基二甲基硅烷基、仲丁基二甲基硅烷基、叔丁基二甲基硅烷基、叔戊基二甲基硅烷基、甲基二乙基硅烷基、丙基二乙基硅烷基、异丙基二乙基硅烷基、丁基二乙基硅烷基、仲丁基二乙基硅烷基、叔丁基二乙基硅烷基、叔戊基二乙基硅烷基、甲基二丙基硅烷基、乙基二丙基硅烷基、丁基二丙基硅烷基、仲丁基二丙基硅烷基、叔丁基二丙基硅烷基、叔戊基二丙基硅烷基、甲基二异丙基硅烷基、乙基二异丙基硅烷基、丁基二异丙基硅烷基、仲丁基二异丙基硅烷基、叔丁基二异丙基硅烷基、叔戊基二异丙基硅烷基等。Specific examples of the trialkylsilyl group include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-tert-butylsilyl, tri-tert-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, tert-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldimethylsilyl, Ethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, tert-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, tert-amyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, tert-butyldiisopropylsilyl, tert-amyldiisopropylsilyl and the like.

作为“三环烷基硅烷基”，可列举硅烷基中的三个氢分别独立地由环烷基取代的基，所述环烷基可引用所述作为第一取代基中的“环烷基”而说明的基。对于取代而言优选的环烷基为碳数5～10的环烷基，具体而言，可列举：环戊基、环己基、环庚基、环辛基、环壬基、环癸基、双环[1.1.1]戊基、双环[2.0.1]戊基、双环[1.2.1]己基、双环[3.0.1]己基、双环[2.1.2]庚基、双环[2.2.2]辛基、金刚烷基、十氢萘基、十氢薁基等。Examples of the "tricycloalkylsilyl group" include groups in which three hydrogen atoms in the silyl group are independently replaced by cycloalkyl groups, and the cycloalkyl group may be the group described as the "cycloalkyl group" in the first substituent group. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, decahydroazulyl, and the like.

作为具体的三环烷基硅烷基，可列举三环戊基硅烷基、三环己基硅烷基等。Specific examples of the tricycloalkylsilyl group include a tricyclopentylsilyl group and a tricyclohexylsilyl group.

作为取代有两个烷基与一个环烷基的二烷基环烷基硅烷基、及取代有一个烷基与两个环烷基的烷基二环烷基硅烷基的具体例，可列举取代有选自所述具体的烷基及环烷基中的基的硅烷基。Specific examples of the dialkylcycloalkylsilyl group substituted with two alkyl groups and one cycloalkyl group and the alkyldicycloalkylsilyl group substituted with one alkyl group and two cycloalkyl groups include silyl groups substituted with a group selected from the above-mentioned specific alkyl groups and cycloalkyl groups.

作为取代有两个烷基与一个芳基的二烷基芳基硅烷基、取代有一个烷基与两个芳基的烷基二芳基硅烷基、以及取代有三个芳基的三芳基硅烷基的具体例，可列举取代有选自所述具体的烷基及芳基中的基的硅烷基。作为三芳基硅烷基的具体例，可特别列举三苯基硅烷基。Specific examples of dialkylarylsilyl groups substituted with two alkyl groups and one aryl group, alkyldiarylsilyl groups substituted with one alkyl group and two aryl groups, and triarylsilyl groups substituted with three aryl groups include silyl groups substituted with groups selected from the above-mentioned specific alkyl groups and aryl groups. Specific examples of triarylsilyl groups include triphenylsilyl groups.

另外，第一取代基的“二芳基硼基”的“芳基”可引用所述芳基的说明。另外，所述两个芳基可经由单键或连结基(例如＞C(-R)₂、＞O、＞S或＞N-R)键结。此处，＞C(-R)₂及＞N-R的R为芳基、杂芳基、二芳基氨基、烷基、环烷基、烷氧基或芳氧基(以上为第一取代基)，在所述第一取代基中可进一步取代有芳基、杂芳基、烷基或环烷基(以上为第二取代基)，作为这些基的具体例，可引用所述作为第一取代基的芳基、杂芳基、二芳基氨基、烷基、环烷基、烷氧基或芳氧基的说明。In addition, the "aryl" of the "diarylboryl" as the first substituent can refer to the description of the aryl group. In addition, the two aryl groups can be bonded via a single bond or a linking group (for example, >C(-R)₂ , >O, >S or >NR). Here, R of >C(-R)₂ and >NR is an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, a cycloalkyl group, an alkoxy group or an aryloxy group (the above are the first substituents), and the first substituent can be further substituted with an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group (the above are the second substituents). As specific examples of these groups, the description of the aryl group, heteroaryl group, diarylamino group, alkyl group, cycloalkyl group, alkoxy group or aryloxy group as the first substituent can be cited.

作为第一取代基的、经取代或未经取代的“芳基”、经取代或未经取代的“杂芳基”、经取代或未经取代的“二芳基氨基”、经取代或未经取代的“二杂芳基氨基”、经取代或未经取代的“芳基杂芳基氨基”、经取代或未经取代的“二芳基硼基(两个芳基可经由单键或连结基键结)”、经取代或未经取代的“烷基”、经取代或未经取代的“环烷基”、经取代或未经取代的“烷氧基”、经取代或未经取代的“芳氧基”、或者经取代的“硅烷基”如说明为经取代或未经取代那样，它们中的至少一个氢可由第二取代基取代。作为所述第二取代基，例如可列举芳基、杂芳基、烷基、环烷基或取代硅烷基，它们的具体例可参照所述“芳基环”或“杂芳基环”的一价基、及作为第一取代基的“烷基”或“环烷基”的说明。另外，在作为第二取代基的芳基或杂芳基中，它们中的至少一个氢由苯基等芳基(具体例为以上所述的基)、甲基、叔丁基等烷基(具体例为以上所述的基)或环己基等环烷基(具体例为以上所述的基)取代的结构也包含于作为第二取代基的芳基或杂芳基中。作为其一例，当第二取代基为咔唑基时，9位上的至少一个氢由苯基等芳基、甲基等烷基或环己基等环烷基取代的咔唑基也包含于作为第二取代基的杂芳基中。As the first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryl groups may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted "silyl" may have at least one hydrogen atom substituted by a second substituent as described as substituted or unsubstituted. Examples of the second substituent include aryl, heteroaryl, alkyl, cycloalkyl, and substituted silyl. Specific examples thereof may refer to the monovalent group of the "aryl ring" or "heteroaryl ring" and the description of the "alkyl" or "cycloalkyl" as the first substituent. In addition, in the aryl or heteroaryl group as the second substituent, a structure in which at least one hydrogen is replaced by an aryl group such as phenyl (specific examples are the groups described above), an alkyl group such as methyl or tert-butyl (specific examples are the groups described above), or a cycloalkyl group such as cyclohexyl (specific examples are the groups described above) is also included in the aryl or heteroaryl group as the second substituent. As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen at the 9-position is replaced by an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl is also included in the heteroaryl group as the second substituent.

可通过第一取代基的结构的位阻性、供电子性及吸电子性来调整发光波长。优选为以下结构式所表示的基，更优选为甲基、叔丁基、叔戊基、叔辛基、新戊基、环己基、金刚烷基、苯基、邻甲苯基、对甲苯基、2,4-二甲苯基、2,5-二甲苯基、2,6-二甲苯基、2,4,6-均三甲苯基、二苯基氨基、二-对甲苯基氨基、双(对(叔丁基)苯基)氨基、咔唑基、3,6-二甲基咔唑基、3,6-二-叔丁基咔唑基及苯氧基，进而优选为甲基、叔丁基、叔戊基、叔辛基、新戊基、金刚烷基、苯基、邻甲苯基、2,6-二甲苯基、2,4,6-均三甲苯基、二苯基氨基、二-对甲苯基氨基、双(对(叔丁基)苯基)氨基、咔唑基、3,6-二甲基咔唑基及3,6-二-叔丁基咔唑基。就合成容易性的观点而言，位阻大的基由于进行选择性合成而优选，具体而言，优选为叔丁基、叔戊基、叔辛基、金刚烷基、邻甲苯基、对甲苯基、2,4-二甲苯基、2,5-二甲苯基、2,6-二甲苯基、2,4,6-均三甲苯基、二-对甲苯基氨基、双(对(叔丁基)苯基)氨基、3,6-二甲基咔唑基及3,6-二-叔丁基咔唑基。The emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent. The group represented by the following structural formula is preferred, and a methyl group, a tert-butyl group, a tert-amyl group, a tert-octyl group, a neopentyl group, a cyclohexyl group, an adamantyl group, a phenyl group, an o-tolyl group, a p-tolyl group, a 2,4-xylyl group, a 2,5-xylyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl group, a 3,6-dimethylcarbazolyl group, a 3,6-di-tert-butylcarbazolyl group, and a phenoxy group are more preferred. A methyl group, a tert-butyl group, a tert-amyl group, a tert-octyl group, a neopentyl group, an adamantyl group, a phenyl group, an o-tolyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl group, a 3,6-dimethylcarbazolyl group, and a 3,6-di-tert-butylcarbazolyl group are further preferred. From the viewpoint of ease of synthesis, a group with large steric hindrance is preferred because selective synthesis can be performed. Specifically, a tert-butyl group, a tert-amyl group, a tert-octyl group, an adamantyl group, an o-tolyl group, a p-tolyl group, a 2,4-xylyl group, a 2,5-xylyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a 3,6-dimethylcarbazolyl group, and a 3,6-di-tert-butylcarbazolyl group are preferred.

在下述结构式中，“Me”表示甲基，“tBu”表示叔丁基，“tAm”表示叔戊基，“tOct”表示叔辛基，*表示键结位置。In the following structural formulas, "Me" represents a methyl group, "tBu" represents a tert-butyl group, "tAm" represents a tert-amyl group, "tOct" represents a tert-octyl group, and * represents a bonding position.

式(D)的X¹及X²中的＞N-R的R为可由所述第二取代基取代的芳基、杂芳基、烷基或环烷基(其中，在作为X¹及X²中的＞N-R的R的芳基中，优选为氨基不进行取代)。作为所述芳基、杂芳基、烷基或环烷基，可列举以上所述的基。另外，作为此时的第二取代基，例如优选为甲基、叔丁基及戊基等烷基、对叔丁基苯基、三甲基硅烷基等取代硅烷基等。烷基的取代位置优选为相对于所述N的取代位置而为对位。作为X¹及X²中的＞N-R的R，特别优选为可由第二取代基取代的碳数6～10的芳基(例如苯基、萘基等)、碳数2～15的杂芳基(例如咔唑基等)、碳数1～5的烷基(例如甲基、乙基等)或碳数5～10的环烷基(优选为环己基或金刚烷基)。R of >NR in^X1 and^X2 in formula (D) is an aryl group, heteroaryl group, alkyl group or cycloalkyl group which may be substituted by the second substituent (wherein, in the aryl group as R of >NR in^X1 and^X2 , it is preferred that the amino group is not substituted). Examples of the aryl group, heteroaryl group, alkyl group or cycloalkyl group include the groups described above. In addition, as the second substituent in this case, for example, alkyl groups such as methyl, tert-butyl and pentyl, substituted silyl groups such as p-tert-butylphenyl and trimethylsilyl are preferred. The substitution position of the alkyl group is preferably para relative to the substitution position of the N. As R of >NR in^X1 and^X2 , an aryl group having 6 to 10 carbon atoms (such as phenyl, naphthyl, etc.), a heteroaryl group having 2 to 15 carbon atoms (such as carbazolyl, etc.), an alkyl group having 1 to 5 carbon atoms (such as methyl, ethyl, etc.), or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) which may be substituted by the second substituent is particularly preferred.

所述说明也同样适用于式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中的X¹及X²。The above description also applies to^X1 and^X2 in Formula (Da), Formula (Db), Formula (Dc), Formula (Dd), Formula (De) and Formula (Df).

式(D)的X¹及X²中的＞C(-R)₂的R分别独立地为氢、可由所述第二取代基取代的芳基、杂芳基、烷基或环烷基。作为所述芳基、杂芳基、烷基或环烷基，可列举以上所述的基。特别优选为碳数6～10的芳基(例如苯基、萘基等)、碳数2～15的杂芳基(例如咔唑基等)、碳数1～5的烷基(例如甲基、乙基等)或碳数5～10的环烷基(优选为环己基或金刚烷基)。＞C(-R)₂的两个R优选为相同，另外，两个R可键结而形成环。＞C(-R)₂的两个R特别优选为均为甲基。In^X1 and^X2 of formula (D), R of >C(-R)₂ is independently hydrogen, an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group which may be substituted by the second substituent. Examples of the aryl group, heteroaryl group, alkyl group or cycloalkyl group include the groups described above. Particularly preferred are aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl groups having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl groups having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). The two R of >C(-R)₂ are preferably the same, and the two R may be bonded to form a ring. The two R of >C(-R)₂ are particularly preferably both methyl groups.

所述说明也同样适用于式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中的X¹及X²。The above description also applies to^X1 and^X2 in Formula (Da), Formula (Db), Formula (Dc), Formula (Dd), Formula (De) and Formula (Df).

作为式(D)中的X¹及X²中的＞N-R的R与A环、B环及C环的至少一个环键结时的连结基，例如可列举-O-、-S-、-C(-R)₂-或单键等，它们中的“-C(-R)₂-”的R为氢、烷基或环烷基，作为所述烷基或环烷基，可列举以上所述的基。特别优选为碳数1～5的烷基(例如甲基、乙基等)或碳数5～10的环烷基(优选为环己基或金刚烷基)。Examples of the linking group when R of >NR in^X1 and^X2 in formula (D) is bonded to at least one of the A ring, B ring and C ring include -O-, -S-, -C(-R)_2- or a single bond, wherein R of "-C(-R)_2- " is hydrogen, an alkyl group or a cycloalkyl group, and examples of the alkyl group or cycloalkyl group include the above-mentioned groups. Particularly preferred are alkyl groups having 1 to 5 carbon atoms (e.g., methyl group, ethyl group, etc.) or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl group or adamantyl group).

所述说明也同样适用于式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中的X¹及X²。The above description also applies to^X1 and^X2 in Formula (Da), Formula (Db), Formula (Dc), Formula (Dd), Formula (De) and Formula (Df).

本发明中，发光层中所含的多环芳香族化合物为式(D)所表示的单量体或为具有多个式(D)所表示的部分结构的多聚体。即，式(D)所表示的单量体为式(D)所表示的化合物。多聚体优选为二聚体～六聚体，更优选为二聚体～三聚体，特别优选为二聚体。多聚体只要是在一个化合物中具有多个式(D)所表示的部分结构的形态即可，例如除多个所述部分结构利用单键、碳数1～3的亚烷基、亚苯基、亚萘基等连结基进行键结的形态(连结型多聚体)，也可为以在多个部分结构中共有所述部分结构中所含的任意环(A环、B环或C环或者a环、b环或c环等)的方式进行键结的形态(环共有型多聚体)，另外，还可为以所述部分结构中所含的任意环(A环、B环或C环或者a环、b环或c环)彼此缩合的方式进行键结的形态(环缩合型多聚体)，优选为环共有型多聚体及环缩合型多聚体，更优选为环共有型多聚体。In the present invention, the polycyclic aromatic compound contained in the light-emitting layer is a monomer represented by formula (D) or a polymer having a plurality of partial structures represented by formula (D). That is, the monomer represented by formula (D) is a compound represented by formula (D). The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer may be in a form in which a plurality of partial structures represented by formula (D) are present in one compound. For example, in addition to a form in which a plurality of the partial structures are bonded by a single bond, a linking group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthyl group, etc. (a bonded type polymer), it may also be a form in which the plurality of partial structures share any ring (A ring, B ring or C ring or a ring, b ring or c ring, etc.) contained in the partial structure (a ring-sharing type polymer). In addition, it may also be a form in which any ring (A ring, B ring or C ring or a ring, b ring or c ring) contained in the partial structure are condensed with each other (a ring-condensed type polymer). Preferably, it is a ring-sharing type polymer and a ring-condensed type polymer, and more preferably, it is a ring-sharing type polymer.

关于此种多聚体，例如作为具有多个式(D-a)所表示的部分结构的多聚体，可列举下述式(D-a-4)、式(D-a-4-1)、式(D-a-4-2)、式(D-a-5-1)～式(D-a-5-4)或式(D-a-6)所表示的多环芳香族化合物。下述式(D-a-4)所表示的多环芳香族化合物为以共有作为式(D-a)中的a环的苯环的方式在一个化合物中具有多个式(D-a)所表示的部分结构的多环芳香族化合物。另外，下述式(D-a-4-1)所表示的多环芳香族化合物为以共有作为式(D-a)中的a环的苯环的方式在一个化合物中具有两个式(D-a)所表示的部分结构的多环芳香族化合物。另外，下述式(D-a-4-2)所表示的多环芳香族化合物为以共有作为式(D-a)中的a环的苯环的方式在一个化合物中具有三个式(D-a)所表示的部分结构的多环芳香族化合物。另外，下述式(D-a-5-1)～式(D-a-5-4)所表示的多环芳香族化合物为以共有作为式(D-a)中的b环(或c环)的苯环的方式在一个化合物中具有多个式(D-a)所表示的部分结构的多环芳香族化合物。另外，若以式(D-a)进行说明，则下述式(D-a-6)所表示的多环芳香族化合物为以例如作为某一部分结构的b环(或a环、c环)的苯环与作为某一部分结构的b环(或a环、c环)的苯环进行缩合的方式在一个化合物中具有多个式(D-a)所表示的部分结构的多环芳香族化合物。Regarding such a multimer, for example, as a multimer having a plurality of partial structures represented by the formula (D-a), there can be listed polycyclic aromatic compounds represented by the following formula (D-a-4), formula (D-a-4-1), formula (D-a-4-2), formula (D-a-5-1) to formula (D-a-5-4) or formula (D-a-6). The polycyclic aromatic compound represented by the following formula (D-a-4) is a polycyclic aromatic compound having a plurality of partial structures represented by the formula (D-a) in one compound in a manner that the benzene ring serving as the a ring in the formula (D-a) is shared. In addition, the polycyclic aromatic compound represented by the following formula (D-a-4-1) is a polycyclic aromatic compound having two partial structures represented by the formula (D-a) in one compound in a manner that the benzene ring serving as the a ring in the formula (D-a) is shared. In addition, the polycyclic aromatic compound represented by the following formula (D-a-4-2) is a polycyclic aromatic compound having three partial structures represented by the formula (D-a) in one compound in a manner that the benzene ring as the a ring in the formula (D-a) is shared. In addition, the polycyclic aromatic compounds represented by the following formulas (D-a-5-1) to (D-a-5-4) are polycyclic aromatic compounds having multiple partial structures represented by the formula (D-a) in one compound in a manner that the benzene ring as the b ring (or c ring) in the formula (D-a) is shared. In addition, if the formula (D-a) is used for explanation, the polycyclic aromatic compound represented by the following formula (D-a-6) is a polycyclic aromatic compound having multiple partial structures represented by the formula (D-a) in one compound in a manner that, for example, a benzene ring as the b ring (or a ring, c ring) of a certain partial structure is condensed with a benzene ring as the b ring (or a ring, c ring) of a certain partial structure.

多环芳香族化合物可为将式(D-a-4)、式(D-a-4-1)或式(D-a-4-2)所表现的多聚化形态与式(D-a-5-1)～式(D-a-5-4)的任一者或式(D-a-6)所表现的多聚化形态组合而成的多聚体，也可为将式(D-a-5-1)～式(D-a-5-4)的任一者所表现的多聚化形态与式(D-a-6)所表现的多聚化形态组合而成的多聚体，也可为将式(D-a-4)、式(D-a-4-1)或式(D-a-4-2)所表现的多聚化形态与式(D-a-5-1)～式(D-a-5-4)的任一者所表现的多聚化形态及式(D-a-6)所表现的多聚化形态组合而成的多聚体。The polycyclic aromatic compound may be a polymer formed by combining a polymerized form represented by formula (D-a-4), formula (D-a-4-1) or formula (D-a-4-2) with any one of formulas (D-a-5-1) to (D-a-5-4) or a polymerized form represented by formula (D-a-6); it may be a polymer formed by combining a polymerized form represented by any one of formulas (D-a-5-1) to (D-a-5-4) with a polymerized form represented by formula (D-a-6); it may be a polymer formed by combining a polymerized form represented by formula (D-a-4), formula (D-a-4-1) or formula (D-a-4-2) with a polymerized form represented by any one of formulas (D-a-5-1) to (D-a-5-4) and a polymerized form represented by formula (D-a-6).

另外，作为式(D)所表示的单量体或具有多个式(D)所表示的部分结构的多聚体的多环芳香族化合物的化学结构中的氢的全部或一部分也可为氘、氰基或卤素。例如，在式(D)中，A环、B环、C环(A环～C环为芳基环或杂芳基环)、针对A环～C环的取代基、以及X¹及X²为＞N-R或＞C(-R)₂时的R(＝烷基、环烷基、芳基)中的氢可由氘、氰基或卤素取代，这些中，可列举芳基或杂芳基中的全部或一部分氢由氘、氰基或卤素取代的形态。卤素为氟、氯、溴或碘，优选为氟、氯或溴，更优选为氟或氯。In addition, all or part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound which is a monomer represented by formula (D) or a polymer having a plurality of partial structures represented by formula (D) may be deuterium, cyano or halogen. For example, in formula (D), hydrogen atoms in ring A, ring B, ring C (ring A to ring C are aryl rings or heteroaryl rings), substituents for ring A to ring C, and R (=alkyl, cycloalkyl, aryl) when^X1 and^X2 are >NR or >C(-R)₂ may be substituted by deuterium, cyano or halogen, and among these, the form in which all or part of the hydrogen atoms in the aryl or heteroaryl group are substituted by deuterium, cyano or halogen can be cited. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

另外，选自由作为式(D)所表示的单量体或具有多个式(D)所表示的部分结构的多聚体的多环芳香族化合物的化学结构中的芳基环及杂芳基环所组成的群组中的至少一者可由至少一个环烷烃缩合。关于作为式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的单量体或具有多个式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的部分结构的多聚体的多环芳香族化合物，也相同。In addition, at least one of the aryl rings and heteroaryl rings in the chemical structure of the polycyclic aromatic compound which is a monomer represented by formula (D) or a polymer having a plurality of partial structures represented by formula (D) may be condensed with at least one cycloalkane. The same applies to the polycyclic aromatic compound which is a monomer represented by formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f) or a polymer having a plurality of partial structures represented by formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f).

例如，作为A环、B环、C环、a环、b环、c环的芳基环及杂芳基环中的芳基环及杂芳基环；作为A环～C环中的第一取代基及第二取代基的芳基(芳基、二芳基氨基、芳基杂芳基氨基、二芳基硼基或芳氧基中的芳基部分)及杂芳基(杂芳基、二杂芳基氨基或芳基杂芳基氨基中的杂芳基部分)；作为针对a环、b环、c环的第一取代基及第二取代基的芳基(与上述相同)及杂芳基(与上述相同)；以及作为(作为X¹、X²的)＞N-R及＞C(-R)₂的R的芳基(与上述相同)及杂芳基(与上述相同)中的至少一者可由至少一个环烷烃缩合。For example, the aryl ring and heteroaryl ring in the aryl ring and heteroaryl ring of the A ring, the B ring, the C ring, the a ring, the b ring, and the c ring; the aryl group (aryl, diarylamino, arylheteroarylamino, diarylboryl or aryloxy) and heteroaryl group (heteroaryl, diheteroarylamino or arylheteroarylamino) as the first and second substituents in the A ring to the C ring; the aryl group (the same as above) and heteroaryl group (the same as above) as the first and second substituents for the a ring, the b ring, and the c ring; and at least one of the aryl group (the same as above) and heteroaryl group (the same as above) as R (as X¹ and X² )>NR and>C(-R)₂ may be condensed with at least one cycloalkane.

优选为：作为A环、B环、C环、a环、b环、c环的芳基环及杂芳基环；作为A环～C环中的第一取代基的芳基(芳基、二芳基氨基、二芳基硼基或芳氧基中的芳基部分)及杂芳基(杂芳基或二杂芳基氨基中的杂芳基部分)；作为针对a环～c环的第一取代基的芳基(与上述相同)及杂芳基(与上述相同)；以及作为(作为X¹、X²的)＞N-R及＞C(-R)₂的R的芳基(与上述相同)及杂芳基(与上述相同)中的至少一者可由至少一个环烷烃缩合。Preferred are: aryl rings and heteroaryl rings as ring A, ring B, ring C, ring a, ring b, and ring c; aryl groups (aryl groups, diarylamino groups, diarylboryl groups, or aryloxy groups) and heteroaryl groups (heteroaryl groups or heteroaryl groups in diheteroarylamino groups) as first substituents in rings A to C; aryl groups (the same as above) and heteroaryl groups (the same as above) as first substituents for rings a to c; and at least one of aryl groups (the same as above) and heteroaryl groups (the same as above) as R (as^X1 ,^X2 )>NR and>C(-R)₂ may be condensed with at least one cycloalkane.

更优选为：作为A环、B环、C环、a环、b环、c环的芳基环；作为A环～C环中的第一取代基的芳基(芳基或二芳基氨基中的芳基部分)及杂芳基(杂芳基中的杂芳基部分)；作为针对a环、b环、c环的第一取代基的芳基(与上述相同)及杂芳基(与上述相同)；以及作为(作为X¹、X²的)＞N-R及＞C(-R)₂的R的芳基(与上述相同)中的至少一者可由至少一个环烷烃缩合。More preferably, the aryl rings as the A ring, the B ring, the C ring, the a ring, the b ring, and the c ring; the aryl group (the aryl part of the aryl or diarylamino group) and the heteroaryl group (the heteroaryl part of the heteroaryl group) as the first substituent in the A ring to the C ring; the aryl group (the same as above) and the heteroaryl group (the same as above) as the first substituent for the a ring, the b ring, and the c ring; and at least one of the aryl group (the same as above) as R (as^X1 ,^X2 )>NR and>C(-R)₂ can be condensed with at least one cycloalkane.

进而优选为：作为A环、B环、C环、a环、b环、c环的芳基环；作为A环～C环中的第一取代基的芳基(芳基或二芳基氨基中的芳基部分)；作为针对a环、b环、c环的第一取代基的芳基(与上述相同)；以及作为(作为X¹、X²的)＞N-R及＞C(-R)₂的R的芳基(与上述相同)中的至少一者可由至少一个环烷烃缩合。Further preferably, at least one of the aryl rings as the A ring, the B ring, the C ring, the a ring, the b ring, and the c ring; the aryl group as the first substituent in the A ring to the C ring (the aryl group or the aryl moiety in the diarylamino group); the aryl group as the first substituent for the a ring, the b ring, and the c ring (the same as above); and the aryl group as R (as X¹ or X² ) >NR and >C(-R)₂ (the same as above) can be condensed with at least one cycloalkane.

作为“环烷烃”，可列举：碳数3～24的环烷烃、碳数3～20的环烷烃、碳数3～16的环烷烃、碳数3～14的环烷烃、碳数5～10的环烷烃、碳数5～8的环烷烃、碳数5～6的环烷烃、碳数5的环烷烃等。Examples of the “cycloalkane” include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

作为具体的环烷烃，可列举：环丙烷、环丁烷、环戊烷、环己烷、环庚烷、环辛烷、环壬烷、环癸烷、降冰片烯、双环[1.0.1]丁烷、双环[1.1.1]戊烷、双环[2.0.1]戊烷、双环[1.2.1]己烷、双环[3.0.1]己烷、双环[2.1.2]庚烷、双环[2.2.2]辛烷、金刚烷、二金刚烷、十氢萘及十氢薁以及它们的碳数1～5的烷基(特别是甲基)取代物、卤素(特别是氟)取代物及氘取代物等。Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diadamantane, decahydronaphthalene and decahydroazulene, and alkyl (especially methyl)-substituted, halogen (especially fluorine)-substituted and deuterium-substituted products thereof having 1 to 5 carbon atoms.

这些中，优选为环烷烃的α位的碳(在缩合于芳香族环或杂芳香族环中的环烷基中，与缩合部位的碳邻接的位置的碳)上的至少一个氢经取代的结构，更优选为α位的碳上的两个氢经取代的结构，进而优选为两个α位的碳上的合计四个氢经取代的结构。作为所述取代基，可列举碳数1～5的烷基(特别是甲基)取代物、卤素(特别是氟)取代物及氘取代物等。Among these, a structure in which at least one hydrogen on the carbon at the α position of the cycloalkane (a carbon adjacent to the carbon at the condensation site in the cycloalkyl group condensed to the aromatic ring or heteroaromatic ring) is substituted is preferred, a structure in which two hydrogens on the carbon at the α position are substituted is more preferred, and a structure in which a total of four hydrogens on the two carbons at the α position are substituted is further preferred. Examples of the substituent include alkyl (particularly methyl) substitutions having 1 to 5 carbon atoms, halogen (particularly fluorine) substitutions, and deuterium substitutions.

特别优选为在芳基环或杂芳基环中邻接的碳原子上键结有下述式(B10)或式(B11)所表示的部分结构的结构。Particularly preferred is a structure in which a partial structure represented by the following formula (B10) or formula (B11) is bonded to adjacent carbon atoms in an aryl ring or a heteroaryl ring.

式中，Me表示甲基，*表示键结位置。In the formula, Me represents a methyl group, and * represents a bonding position.

式(B10)及式(B11)中，Me表示甲基。*表示键结位置，式(B10)或式(B11)所表示的基在所键结的芳基环或杂芳基环的环上分别与邻接的两个元素键结。In formula (B10) and formula (B11), Me represents a methyl group. * represents a bonding position, and the group represented by formula (B10) or formula (B11) is bonded to two adjacent elements on the aryl ring or heteroaryl ring to which it is bonded.

作为具有此种结构的化合物的例子，可列举以下化合物。Examples of compounds having such a structure include the following compounds.

缩合于一个芳基环或杂芳基环中的环烷烃的数量优选为1个～3个，更优选为1个或2个，进而优选为1个。例如，以下示出在一个苯环(苯基)中缩合有一个或多个环烷烃的例子。如式(Cy-1-4)及式(Cy-2-4)那样进行缩合的环烷烃彼此也可进行缩合。不论是所缩合的环(基)为苯环(苯基)以外的其他芳香族环或杂芳香族环的情况，还是进行缩合的环烷烃为环戊烷或环己烷以外的其他环烷烃的情况，均相同。The number of cycloalkanes condensed in one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and further preferably 1. For example, an example in which one or more cycloalkanes are condensed in one benzene ring (phenyl) is shown below. Cycloalkanes condensed as in formula (Cy-1-4) and formula (Cy-2-4) may also be condensed with each other. This is the same whether the ring (base) to be condensed is an aromatic ring or heteroaromatic ring other than the benzene ring (phenyl), or whether the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

环烷烃中的至少一个-CH₂-可由-O-取代。例如，以下示出缩合于一个苯环(苯基)的环烷烃中的一个或多个-CH₂-由-O-取代的例子。不论是所缩合的环(基)为苯环(苯基)以外的其他芳香族环或杂芳香族环的情况，还是进行缩合的环烷烃为环戊烷或环己烷以外的其他环烷烃的情况，均相同。At least one -CH₂ - in a cycloalkane may be substituted with -O-. For example, the following shows an example in which one or more -CH₂ - in a cycloalkane condensed with a benzene ring (phenyl) is substituted with -O-. This is the same regardless of whether the condensed ring (group) is an aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl) or whether the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

环烷烃中的至少一个氢可经取代，作为所述取代基，例如可列举芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、二芳基硼基(两个芳基可经由单键或连结基键结)、烷基、环烷基、烷氧基、芳氧基、取代硅烷基、氘、氰基或卤素，它们的详细情况可引用所述第一取代基的说明。这些取代基中，优选为烷基(例如碳数1～6的烷基)、环烷基(例如碳数3～14的环烷基)、卤素(例如氟)及氘等。另外，在环烷基进行取代时，可为形成螺环结构的取代形态。以下示出所述例。At least one hydrogen in the cycloalkane may be substituted, and examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano or halogen, and their details may refer to the description of the first substituent. Among these substituents, alkyl (e.g., alkyl with 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl with 3 to 14 carbon atoms), halogen (e.g., fluorine) and deuterium are preferred. In addition, when the cycloalkyl is substituted, it may be a substitution form that forms a spiro ring structure. The examples are shown below.

作为环烷烃缩合的其他形态，可列举：多环芳香族化合物具有例如R为由环烷烃缩合的芳基的＞N-R、由环烷烃缩合的二芳基氨基(缩合至其芳基部分)、由环烷烃缩合的咔唑基(缩合至其苯环部分)或由环烷烃缩合的苯并咔唑基(缩合至其苯环部分)的例子。关于“二芳基氨基”，可列举作为所述“第一取代基”而说明的基。As other forms of cycloalkane condensation, examples include polycyclic aromatic compounds having, for example, >N-R, where R is an aryl group condensed from cycloalkane, diarylamino groups condensed from cycloalkane (condensed to the aryl part thereof), carbazolyl groups condensed from cycloalkane (condensed to the benzene ring part thereof), or benzocarbazolyl groups condensed from cycloalkane (condensed to the benzene ring part thereof). As for the "diarylamino group", the groups described as the "first substituent" can be mentioned.

另外，作为更具体的例子，可列举：式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)中的R²为由环烷烃缩合的二芳基氨基(缩合至其芳基部分)或由环烷烃缩合的咔唑基(缩合至其苯环部分)的例子。In addition, as more specific examples, there are examples in which^R2 in formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De) or formula (Df) is a diarylamino group condensed by a cycloalkane (condensed to its aromatic portion) or a carbazolyl group condensed by a cycloalkane (condensed to its benzene ring portion).

作为本发明的多环芳香族化合物的更具体的例子，可列举以下结构式所表示的化合物。此外，下述结构式中的“D”表示氘，“Me”表示甲基，“Et”表示乙基，“tBu”表示叔丁基，“tAm”表示叔戊基，“TMS”表示三甲基硅烷基。As more specific examples of the polycyclic aromatic compound of the present invention, compounds represented by the following structural formulas can be cited. In addition, in the following structural formula, "D" represents deuterium, "Me" represents methyl, "Et" represents ethyl, "tBu" represents tert-butyl, "tAm" represents tert-amyl, and "TMS" represents trimethylsilyl.

作为式(D)所表示的单量体或具有多个式(D)所表示的部分结构的多聚体的多环芳香族化合物可参照日本专利特开2018-043984号公报中记载的方法来制造。The polycyclic aromatic compound which is a monomer represented by formula (D) or a polymer having a plurality of partial structures represented by formula (D) can be produced by referring to the method described in Japanese Patent Application Laid-Open No. 2018-043984.

3.有机电场发光元件的制造3. Manufacturing of organic electroluminescent elements

图1表示有机电场发光元件的一例的概略剖面图。图1所示的有机EL元件100包括：基板101、设置于基板101上的阳极102、设置于阳极102上的空穴注入层103、设置于空穴注入层103上的空穴传输层104、设置于空穴传输层104上的发光层105、设置于发光层105上的电子传输层106、设置于电子传输层106上的电子注入层107、以及设置于电子注入层107上的阴极108。FIG1 is a schematic cross-sectional view of an example of an organic electroluminescent element. The organic EL element 100 shown in FIG1 includes a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

此外，有机EL元件100也可使制作顺序相反而形成例如以下的结构，所述结构包括：基板101、设置于基板101上的阴极108、设置于阴极108上的电子注入层107、设置于电子注入层107上的电子传输层106、设置于电子传输层106上的发光层105、设置于发光层105上的空穴传输层104、设置于空穴传输层104上的空穴注入层103、以及设置于空穴注入层103上的阳极102。In addition, the organic EL element 100 can also reverse the production order to form a structure such as the following, which includes: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, a light-emitting layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the light-emitting layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

所述各层并非全部是不可或缺的层，将最小结构单元设为包含阳极102、发光层105及阴极108的结构，空穴注入层103、空穴传输层104、电子传输层106、电子注入层107是可任意设置的层。另外，所述各层可分别包含单一层，也可包含多层。The above-mentioned layers are not all indispensable layers, and the minimum structural unit is set to a structure including an anode 102, a light-emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that can be set arbitrarily. In addition, the above-mentioned layers can each include a single layer or a plurality of layers.

作为构成有机EL元件的层的形态，除所述“基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/阴极”的结构形态以外，也可为“基板/阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极”、“基板/阳极/空穴注入层/发光层/电子传输层/电子注入层/阴极”、“基板/阳极/空穴注入层/空穴传输层/发光层/电子注入层/阴极”、“基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/阴极”、“基板/阳极/发光层/电子传输层/电子注入层/阴极”、“基板/阳极/空穴传输层/发光层/电子注入层/阴极”、“基板/阳极/空穴传输层/发光层/电子传输层/阴极”、“基板/阳极/空穴注入层/发光层/电子注入层/阴极”、“基板/阳极/空穴注入层/发光层/电子传输层/阴极”、“基板/阳极/发光层/电子传输层/阴极”、“基板/阳极/发光层/电子注入层/阴极”的结构形态。The morphology of the layers constituting the organic EL element may be, in addition to the structural morphology of “substrate/anode/hole injection layer/hole transport layer/luminescent layer/electron transport layer/electron injection layer/cathode”, “substrate/anode/hole injection layer/luminescent layer/electron transport layer/electron injection layer/cathode”, “substrate/anode/hole injection layer/luminescent layer/electron transport layer/electron injection layer/cathode”, “substrate/anode/hole injection layer/hole transport layer/luminescent layer/electron injection layer/cathode”, “substrate/anode/hole injection layer/hole transport layer/luminescent layer/electron injection layer/cathode”, “substrate/anode/hole injection layer/hole transport layer/luminescent layer/electron injection layer/cathode”, The structural morphology of the substrate is as follows: substrate/anode/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/light-emitting layer/electron transport layer/cathode", and "substrate/anode/light-emitting layer/electron injection layer/cathode".

4.有机电场发光元件中的基板4. Substrate in organic electroluminescent elements

基板101是有机EL元件100的支撑体，通常可使用石英、玻璃、金属、塑料等。基板101根据目的而形成为板状、膜状或片状，例如可使用玻璃板、金属板、金属箔、塑料膜、塑料片等。其中，优选为玻璃板及聚酯、聚甲基丙烯酸酯、聚碳酸酯、聚砜等透明的合成树脂制的板。若为玻璃基板，则可使用钠钙玻璃或无碱玻璃等，另外，厚度也只要是足以保持机械强度的厚度即可，因此例如只要有0.2mm以上即可。厚度的上限值例如为2mm以下，优选为1mm以下。关于玻璃的材质，由于来自玻璃的溶出离子以少为宜，因此优选为无碱玻璃，由于施加了SiO₂等的隔离涂层(barrier coat)的钠钙玻璃也有市售，因此可使用所述钠钙玻璃。另外，为了提高阻气性，也可在基板101的至少一面上设置细密的氧化硅膜等阻气膜，在将阻气性低的合成树脂制的板、膜或片用作基板101的情况下，特别优选为设置阻气膜。The substrate 101 is a support of the organic EL element 100, and quartz, glass, metal, plastic, etc. can be generally used. The substrate 101 is formed into a plate, film or sheet according to the purpose, for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. can be used. Among them, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, polysulfone, etc. are preferably used. If it is a glass substrate, soda-lime glass or alkali-free glass can be used, and the thickness can be sufficient to maintain the mechanical strength, so for example, it can be more than 0.2 mm. The upper limit of the thickness is, for example, less than 2 mm, preferably less than 1 mm. Regarding the material of the glass, since the dissolved ions from the glass are preferably less, alkali-free glass is preferably used, and since soda-lime glass with a barrier coat (barrier coat) of_SiO2 or the like is also commercially available, the soda-lime glass can be used. In addition, in order to improve the gas barrier properties, a gas barrier film such as a fine silicon oxide film may be provided on at least one side of the substrate 101. When a plate, film or sheet made of a synthetic resin with low gas barrier properties is used as the substrate 101, it is particularly preferred to provide a gas barrier film.

5.有机电场发光元件中的阳极5. Anode in organic electroluminescent element

阳极102发挥向发光层105中注入空穴的作用。此外，当在阳极102与发光层105之间设置有空穴注入层103和/或空穴传输层104时，经由这些层向发光层105中注入空穴。The anode 102 plays a role of injecting holes into the light-emitting layer 105. When the hole injection layer 103 and/or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

作为形成阳极102的材料，可列举无机化合物及有机化合物。作为无机化合物，例如可列举：金属(铝、金、银、镍、钯、铬等)、金属氧化物(铟的氧化物、锡的氧化物、铟-锡氧化物(Indium Tin Oxide，ITO)、铟-锌氧化物(Indium Zinc Oxide，IZO)等)、卤化金属(碘化铜等)、硫化铜、碳黑、ITO玻璃或奈塞(NESA)玻璃等。作为有机化合物，例如可列举：聚(3-甲基噻吩)等聚噻吩、聚吡咯、聚苯胺等导电性聚合物等。此外，可自用作有机EL元件的阳极的物质中适宜选择来使用。As materials for forming the anode 102, inorganic compounds and organic compounds can be cited. As inorganic compounds, for example, metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (Indium Tin Oxide, ITO), indium-zinc oxide (Indium Zinc Oxide, IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass or Nesser (NESA) glass, etc. As organic compounds, for example, polythiophenes such as poly (3-methylthiophene), polypyrrole, conductive polymers such as polyaniline, etc. can be cited. In addition, it can be appropriately selected from the substances used as the anode of the organic EL element for use.

透明电极的电阻只要可供给对于发光元件的发光而言充分的电流即可，因此并无限定，但就发光元件的消耗电力的观点而言，理想的是低电阻。例如，若为300Ω/Υ以下的ITO基板，则作为元件电极而发挥功能，但现在也可供给10Ω/Υ左右的基板，因此特别理想的是使用例如100Ω/Υ～5Ω/Υ、优选为50Ω/Υ～5Ω/Υ的低电阻品。ITO的厚度可配合电阻值而任意地选择，但通常多在50nm～300nm之间使用。The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light emission of the light emitting element, but from the perspective of the power consumption of the light emitting element, a low resistance is ideal. For example, if it is an ITO substrate of less than 300Ω/Y, it functions as an element electrode, but a substrate of about 10Ω/Y can also be supplied now, so it is particularly ideal to use a low resistance product of, for example, 100Ω/Y to 5Ω/Y, preferably 50Ω/Y to 5Ω/Y. The thickness of ITO can be arbitrarily selected in accordance with the resistance value, but is usually used between 50nm and 300nm.

6.有机电场发光元件中的空穴注入层、空穴传输层6. Hole injection layer and hole transport layer in organic electroluminescent elements

空穴注入层103发挥将自阳极102迁移而来的空穴高效地注入发光层105内或空穴传输层104内的作用。空穴传输层104发挥将自阳极102所注入的空穴、或自阳极102经由空穴注入层103所注入的空穴高效地传输至发光层105的作用。空穴注入层103及空穴传输层104分别将空穴注入/传输材料的一种或两种以上加以层叠、混合而形成，或者由空穴注入/传输材料与高分子粘结剂的混合物形成。另外，也可向空穴注入/传输材料中添加氯化铁(III)之类的无机盐来形成层。The hole injection layer 103 plays a role in efficiently injecting holes migrated from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role in efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are formed by stacking or mixing one or more hole injection/transport materials, or by a mixture of a hole injection/transport material and a polymer binder. In addition, inorganic salts such as iron (III) chloride can also be added to the hole injection/transport material to form a layer.

作为空穴注入/传输材料，需要在施加有电场的电极间高效地注入/传输来自正极的空穴，理想的是空穴注入效率高、且高效地传输所注入的空穴。因此，优选为电离电位小、且空穴迁移率大、进而稳定性优异、在制造时及使用时不易产生成为陷阱的杂质的物质。As a hole injection/transport material, it is necessary to efficiently inject/transmit holes from the positive electrode between electrodes to which an electric field is applied, and it is ideal that the hole injection efficiency is high and the injected holes are efficiently transported. Therefore, it is preferred that the material has a small ionization potential, a large hole mobility, and excellent stability, and is not prone to produce impurities that become traps during manufacture and use.

作为形成空穴注入层103及空穴传输层104的材料，可自从前以来在光导电材料中作为空穴的电荷传输材料所惯用的化合物、p型半导体、有机EL元件的空穴注入层及空穴传输层中所使用的现有的化合物中选择使用任意的化合物。这些化合物的具体例为咔唑衍生物(N-苯基咔唑、聚乙烯咔唑等)、双(N-芳基咔唑)或双(N-烷基咔唑)等双咔唑衍生物、三芳基胺衍生物(在主链或侧链上具有芳香族三级氨基的聚合物、1,1-双(4-二-对甲苯基氨基苯基)环己烷、N,N'-二苯基-N,N'-二(3-甲基苯基)-4,4'-二氨基联苯、N,N'-二苯基-N,N'-二萘基-4,4'-二氨基联苯、N,N'-二苯基-N,N'-二(3-甲基苯基)-4,4'-二苯基-1,1'-二胺、N,N'-二萘基-N,N'-二苯基-4,4'-二苯基-1,1'-二胺、N⁴,N⁴'-二苯基-N⁴,N⁴'-双(9-苯基-9H-咔唑-3-基)-[1,1'-联苯]-4,4'-二胺、N⁴,N⁴,N⁴',N⁴'-四[1,1'-联苯]-4-基-[1,1'-联苯]-4,4'-二胺、4,4',4”-三(3-甲基苯基(苯基)氨基)三苯基胺、N-([1,1'-联苯]-4-基)-9,9-二甲基-N-(4-(9-苯基-9H-咔唑-3-基)苯基)-9H-芴-2-胺、N,N-双(4-(二苯并[b,d]呋喃-4-基)苯基)-[1,1'：4',1”-三联苯]-4-胺等三苯基胺衍生物、星爆状胺衍生物等)、二苯乙烯衍生物、酞菁衍生物(无金属、铜酞菁等)、吡唑啉衍生物、腙系化合物、苯并呋喃衍生物或噻吩衍生物、噁二唑衍生物、喹噁啉衍生物(例如1,4,5,8,9,12-六氮杂三亚苯-2,3,6,7,10,11-六碳腈等)、卟啉衍生物等杂环化合物、聚硅烷等。在聚合物系中，优选为在侧链上具有所述单量体的聚碳酸酯或苯乙烯衍生物、聚乙烯咔唑及聚硅烷等，但只要是形成发光元件的制作所需的薄膜且可自阳极注入空穴、进而可传输空穴的化合物，则并无特别限定。As materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, and existing compounds used in hole injection layers and hole transport layers of p-type semiconductors and organic EL elements. Specific examples of these compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having aromatic tertiary amino groups in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4 '-diphenyl-N 4 ,N 4 '-diphenyl-N 4 ,N 4 '-diphenyl-N 4 ,N 4 '-diphenyl-N 4 ,N 4 '-diphenyl-N 4 ,N 4 '-diphenyl-N 4 ,N 4 '-diphenyl-N⁴ ,N⁴ '-diphenyl-N⁴ ,N^{4 '} -diphenyl '-Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N⁴ ,N⁴ ,N⁴ ',N⁴ '-tetrakis[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1': 4',1"-terphenyl]-4-amine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonate or styrene derivatives, polyvinylcarbazole and polysilane having the above-mentioned monomers on the side chain are preferred, but there is no particular limitation as long as it is a compound that forms a thin film required for the preparation of a light-emitting element and can inject holes from the anode and then transport holes.

另外，有机半导体的导电性因其掺杂而受到强烈影响这一点也为人所知。此种有机半导体基质物质包含供电子性良好的化合物或电子接受性良好的化合物。为了掺杂供电子物质，已知有四氰基醌二甲烷(Tetracyanoquinodimethane，TCNQ)或2,3,5,6-四氟四氰基-1,4-苯醌二甲烷(2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane，F4TCNQ)等强电子接受体(例如参照文献“M.法伊弗、A.拜尔、T.弗里茨、K.利奥(M.Pfeiffer,A.Beyer,T.Fritz,K.Leo),《应用物理学快报(Appl.Phys.Lett.)》,73(22),3202-3204(1998)”及文献“J.布洛赫维茨、M.法伊弗、T.弗里茨、K.利奥(J.Blochwitz,M.Pfeiffer,T.Fritz,K.Leo),《应用物理学快报(Appl.Phys.Lett.)》,73(6),729-731(1998)”)。它们通过供电子型基础物质(空穴传输物质)中的电子迁移过程而生成所谓的空穴。基础物质的传导性根据空穴的数量及迁移率而发生相当大的变化。作为具有空穴传输特性的基质物质，已知有例如联苯胺衍生物(N,N'-双(3-甲基苯基)-N,N'-双(苯基)联苯胺(N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine，TPD)等)或星爆状胺衍生物(4,4',4”-三(N,N-二苯基氨基)三苯胺(4,4',4”-Tris(N,N-diphenylamino)triphenylamine，TDATA)等)、或者特定金属酞菁(特别是锌酞菁(ZnPc)等)(日本专利特开2005-167175号公报)。It is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials contain compounds with good electron donating properties or compounds with good electron accepting properties. For doping electron donating materials, strong electron acceptors such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane (F4TCNQ) are known (for example, see the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo ( ... Beyer, T. Fritz, K. Leo), "Appl. Phys. Lett.", 73(22), 3202-3204 (1998)" and the reference "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo), "Appl. Phys. Lett.", 73(6), 729-731 (1998)"). They generate so-called holes through the electron migration process in the electron-donating base material (hole transport material). The conductivity of the base material varies significantly depending on the number and mobility of the holes. As a host material having hole transport properties, for example, benzidine derivatives (N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine (N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine, TPD), starburst amine derivatives (4,4',4"-tris(N,N-diphenylamino)triphenylamine (4,4',4"-Tris(N,N-diphenylamino)triphenylamine, TDATA), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Gazette No. 2005-167175).

7.有机电场发光元件中的发光层7. Light-emitting layer in organic electroluminescent elements

发光层105是通过在施加有电场的电极间，使自阳极102所注入的空穴与自阴极108所注入的电子再结合而发光的层。作为形成发光层105的材料，只要是由空穴与电子的再结合而得到激发来发光的化合物(发光性化合物)即可，优选为可形成稳定的薄膜形状、且在固体状态下显示出强的发光(荧光)效率的化合物。在本发明中，作为发光层用的材料，使用式(H)所表示的蒽系化合物、与作为式(D)所表示的单量体或具有多个式(D)所表示的部分结构的多聚体的多环芳香族化合物的至少一种。式(H)所表示的蒽系化合物只要用作主体材料即可，作为式(D)所表示的单量体或具有多个式(D)所表示的部分结构的多聚体的多环芳香族化合物只要用作掺杂剂材料即可。The light-emitting layer 105 is a layer that emits light by allowing holes injected from the anode 102 to recombine with electrons injected from the cathode 108 between electrodes to which an electric field is applied. As a material for forming the light-emitting layer 105, any compound (luminescent compound) that is excited to emit light by the recombination of holes and electrons can be used, and preferably a compound that can form a stable thin film shape and shows strong luminescence (fluorescence) efficiency in a solid state. In the present invention, as a material for the light-emitting layer, at least one of an anthracene compound represented by formula (H) and a polycyclic aromatic compound that is a monomer represented by formula (D) or a polymer having a plurality of partial structures represented by formula (D) is used. The anthracene compound represented by formula (H) can be used as a host material, and the polycyclic aromatic compound that is a monomer represented by formula (D) or a polymer having a plurality of partial structures represented by formula (D) can be used as a dopant material.

发光层可为单一层，也可包含多层，任一者均可，且分别由发光层用材料(主体材料、掺杂剂材料)形成。主体材料与掺杂剂材料分别可为一种，也可为多种的组合，任一者均可。掺杂剂材料可包含于主体材料整体内，也可包含于部分主体材料内，任一者均可。作为掺杂方法，可通过与主体材料的共蒸镀法来形成，也可事先与主体材料混合后同时蒸镀。The light-emitting layer may be a single layer or may include multiple layers, either of which is acceptable, and is formed of materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may be one type or a combination of multiple types, either of which is acceptable. The dopant material may be contained in the entire host material or in part of the host material, either of which is acceptable. As a doping method, it can be formed by co-evaporation with the host material, or it can be mixed with the host material in advance and then evaporated simultaneously.

主体材料的使用量根据主体材料的种类而不同，只要配合所述主体材料的特性来决定即可。主体材料的使用量的基准优选为发光层用材料整体的50质量％～99.999质量％，更优选为80质量％～99.95质量％，进而优选为90质量％～99.9质量％。The amount of the host material used varies depending on the type of the host material and can be determined based on the characteristics of the host material. The base amount of the host material used is preferably 50% to 99.999% by mass of the total material for the light-emitting layer, more preferably 80% to 99.95% by mass, and even more preferably 90% to 99.9% by mass.

掺杂剂材料的使用量根据掺杂剂材料的种类而不同，只要配合所述掺杂剂材料的特性来决定即可。掺杂剂的使用量的基准优选为发光层用材料整体的0.001质量％～50质量％，更优选为0.05质量％～20质量％，进而优选为0.1质量％～10质量％。若为所述范围，则例如就可防止浓度淬灭现象的方面而言优选。The amount of the dopant material used varies depending on the type of the dopant material and can be determined by matching the characteristics of the dopant material. The base amount of the dopant used is preferably 0.001% to 50% by mass of the total material for the light-emitting layer, more preferably 0.05% to 20% by mass, and further preferably 0.1% to 10% by mass. If it is within the above range, it is preferred, for example, in terms of preventing concentration quenching.

作为主体材料，只要使用式(H)所表示的蒽系化合物即可。此外，也可并用自从前作为发光体而已知的其他的蒽、芘、二苯并或芴等的稠环衍生物、双苯乙烯基蒽衍生物或二苯乙烯基苯衍生物等双苯乙烯基衍生物、四苯基丁二烯衍生物、环戊二烯衍生物、咔唑衍生物。As the host material, an anthracene compound represented by formula (H) may be used. In addition, other anthracene, pyrene, dibenzo[pi]ne, and pyrene compounds known as luminescent materials may also be used in combination. or fused ring derivatives such as fluorene, bistyryl derivatives such as bistyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, and carbazole derivatives.

8.有机电场发光元件中的电子注入层、电子传输层8. Electron injection layer and electron transport layer in organic electroluminescent elements

电子注入层107发挥将自阴极108迁移而来的电子高效地注入发光层105内或电子传输层106内的作用。电子传输层106发挥将自阴极108所注入的电子、或自阴极108经由电子注入层107所注入的电子高效地传输至发光层105的作用。电子传输层106及电子注入层107分别将电子传输/注入材料的一种或两种以上加以层叠、混合而形成，或者由电子传输/注入材料与高分子粘结剂的混合物形成。The electron injection layer 107 plays a role in efficiently injecting electrons migrated from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role in efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are respectively formed by stacking or mixing one or more electron transport/injection materials, or are formed by a mixture of an electron transport/injection material and a polymer binder.

所谓电子注入/传输层是担负自阴极注入电子、进而传输电子的层，理想的是电子注入效率高、且高效地传输所注入的电子。因此，优选为电子亲和力大、且电子迁移率大、进而稳定性优异、在制造时及使用时不易产生成为陷阱的杂质的物质。然而，在考虑了空穴与电子的传输平衡的情况下，当主要发挥可高效地阻止来自阳极的空穴未再结合而流向阴极侧的作用时，即便电子传输能力并不那么高，也与电子传输能力高的材料同等地具有提高发光效率的效果。因此，本实施方式中的电子注入/传输层也可包含能够高效地阻止空穴迁移的层的功能。The so-called electron injection/transport layer is a layer responsible for injecting electrons from the cathode and then transmitting electrons, and it is desirable that the electron injection efficiency is high and the injected electrons are efficiently transmitted. Therefore, it is preferably a material with large electron affinity, large electron mobility, excellent stability, and impurities that are not easy to produce when manufacturing and using it. However, considering the transmission balance of holes and electrons, when the main effect of efficiently preventing the holes from the anode from being recombined and flowing to the cathode side is played, even if the electron transmission ability is not so high, it is equally with the material with high electron transmission ability. There is the effect of improving luminous efficiency. Therefore, the electron injection/transport layer in the present embodiment may also include the function of the layer that can efficiently prevent the migration of holes.

作为形成电子传输层106或电子注入层107的材料(电子传输材料)，可自从前以来在光导电材料中作为电子传递化合物所惯用的化合物、有机EL元件的电子注入层及电子传输层中所使用的现有的化合物中任意地选择来使用。The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transfer compounds in photoconductive materials and existing compounds used in electron injection layers and electron transport layers of organic EL elements.

作为电子传输层或电子注入层中所使用的材料，优选为含有选自如下化合物中的至少一种：含有包含选自碳、氢、氧、硫、硅及磷中的一种以上的原子的芳香族环或杂芳香族环的化合物；吡咯衍生物及其稠环衍生物；以及具有电子接受性氮的金属络合物。具体而言，可列举：萘、蒽等稠环系芳香族环衍生物，以4,4'-双(二苯基乙烯基)联苯为代表的苯乙烯基系芳香族环衍生物，紫环酮衍生物，香豆素衍生物，萘二甲酰亚胺衍生物，蒽醌或联苯醌等醌衍生物，氧化磷衍生物，芳基腈衍生物及吲哚衍生物等。作为具有电子接受性氮的金属络合物，例如可列举：羟基苯基噁唑络合物等羟基唑络合物、甲亚胺络合物、环庚三烯酚酮金属络合物、黄酮醇金属络合物及苯并喹啉金属络合物等。这些材料可单独使用，也可与不同的材料混合使用。As the material used in the electron transport layer or the electron injection layer, it is preferably containing at least one selected from the following compounds: a compound containing an aromatic ring or heteroaromatic ring containing one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus; a pyrrole derivative and its fused ring derivative; and a metal complex with electron-accepting nitrogen. Specifically, it can be listed: fused ring aromatic ring derivatives such as naphthalene and anthracene, styrene aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl, purple ring ketone derivatives, coumarin derivatives, naphthalene dicarboximide derivatives, quinone derivatives such as anthraquinone or diphenoquinone, phosphorus oxide derivatives, aryl nitrile derivatives and indole derivatives. As a metal complex with electron-accepting nitrogen, for example, hydroxyl oxazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes can be listed. These materials can be used alone or mixed with different materials.

另外，作为其他电子传递化合物的具体例，可列举：吡啶衍生物、萘衍生物、蒽衍生物、苯并芴衍生物、菲咯啉衍生物、紫环酮衍生物、香豆素衍生物、萘二甲酰亚胺衍生物、蒽醌衍生物、联苯醌衍生物、二苯基醌衍生物、苝衍生物、噁二唑衍生物(1,3-双[(4-叔丁基苯基)1,3,4-噁二唑基]亚苯等)、噻吩衍生物、三唑衍生物(N-萘基-2,5-二苯基-1,3,4-三唑等)、噻二唑衍生物、8-羟基喹啉(oxine)衍生物的金属络合物、羟基喹啉系金属络合物、喹噁啉衍生物、喹噁啉衍生物的聚合物、苯并唑(benzazole)类化合物、镓络合物、吡唑衍生物、全氟化亚苯基衍生物、三嗪衍生物、吡嗪衍生物、苯并喹啉衍生物(2,2'-双(苯并[h]喹啉-2-基)-9,9'-螺二芴等)、咪唑并吡啶衍生物、硼烷衍生物、苯并咪唑衍生物(三(N-苯基苯并咪唑-2-基)苯等)、苯并噁唑衍生物、苯并噻唑衍生物、喹啉衍生物、三联吡啶等寡聚吡啶衍生物、联吡啶衍生物、三联吡啶衍生物(1,3-双(4'-(2,2'：6',2”-三联吡啶基))苯等)、萘啶衍生物(双(1-萘基)-4-(1,8-萘啶-2-基)苯基氧化膦等)、醛连氮衍生物、芳基腈衍生物、吲哚衍生物、氧化膦衍生物、双苯乙烯基衍生物等。In addition, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline (oxine) derivatives, hydroxyquinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazoles derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6',2"-terpyridyl))benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, aryl nitrile derivatives, indole derivatives, phosphine oxide derivatives, bisphenylvinyl derivatives, etc.

另外，也可使用具有电子接受性氮的金属络合物，例如可列举：羟基喹啉系金属络合物或羟基苯基噁唑络合物等羟基唑络合物、甲亚胺络合物、环庚三烯酚酮金属络合物、黄酮醇金属络合物及苯并喹啉金属络合物等。In addition, metal complexes having electron-accepting nitrogen can also be used, examples of which include hydroxyquinoline metal complexes, hydroxyoxazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

所述材料可单独使用，也可与不同的材料混合使用。The materials can be used alone or in combination with different materials.

所述材料中，优选为硼烷衍生物、吡啶衍生物、荧蒽衍生物、BO系衍生物、蒽衍生物、苯并芴衍生物、氧化膦衍生物、嘧啶衍生物、芳基腈衍生物、三嗪衍生物、苯并咪唑衍生物、菲咯啉衍生物及羟基喹啉系金属络合物。Among the above materials, preferred are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aromatic nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives and hydroxyquinoline metal complexes.

＜硼烷衍生物＞＜Borane derivatives＞

硼烷衍生物例如为下述式(ETM-1)所表示的化合物，详细而言在日本专利特开2007-27587号公报中进行了公开。The borane derivative is, for example, a compound represented by the following formula (ETM-1), and its details are disclosed in Japanese Patent Application Laid-Open No. 2007-27587.

式(ETM-1)中，R¹¹及R¹²分别独立地为氢、烷基、环烷基、可经取代的芳基、经取代的硅烷基、可经取代的含氮杂环或氰基的至少一者，R¹³～R¹⁶分别独立地为可经取代的烷基、可经取代的环烷基或可经取代的芳基，X为可经取代的亚芳基，Y为可经取代的碳数16以下的芳基、经取代的硼基或可经取代的咔唑基，而且，n分别独立地为0～3的整数。另外，作为“可经取代”或“经取代”时的取代基，可列举：芳基、杂芳基、烷基或环烷基等。In formula (ETM-1), R¹¹ and R¹² are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group which may be substituted, a silyl group which may be substituted, a nitrogen-containing heterocyclic ring which may be substituted, or a cyano group, R¹³ to R¹⁶ are each independently a alkyl group which may be substituted, a cycloalkyl group which may be substituted, or an aryl group which may be substituted, X is a arylene group which may be substituted, Y is an aryl group having 16 or less carbon atoms which may be substituted, a boryl group which may be substituted, or a carbazolyl group which may be substituted, and n is each independently an integer of 0 to 3. In addition, examples of the substituent in the case of "which may be substituted" or "substituted" include an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group.

式(ETM-1)所表示的化合物中，优选为下述式(ETM-1-1)所表示的化合物或下述式(ETM-1-2)所表示的化合物。Among the compounds represented by the formula (ETM-1), the compounds represented by the following formula (ETM-1-1) or the compounds represented by the following formula (ETM-1-2) are preferred.

式(ETM-1-1)中，R¹¹及R¹²分别独立地为氢、烷基、环烷基、可经取代的芳基、经取代的硅烷基、可经取代的含氮杂环或氰基的至少一者，R¹³～R¹⁶分别独立地为可经取代的烷基、可经取代的环烷基或可经取代的芳基，R²¹及R²²分别独立地为氢、烷基、环烷基、可经取代的芳基、经取代的硅烷基、可经取代的含氮杂环或氰基的至少一者，X¹为可经取代的碳数20以下的亚芳基，n分别独立地为0～3的整数，而且，m分别独立地为0～4的整数。另外，作为“可经取代”或“经取代”时的取代基，可列举：芳基、杂芳基、烷基或环烷基等。In formula (ETM-1-1), R¹¹ and R¹² are each independently hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocyclic ring or cyano, R¹³ to R¹⁶ are each independently substituted alkyl, substituted cycloalkyl or substituted aryl, R²¹ and R²² are each independently hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocyclic ring or cyano, X¹ is a substitutable arylene group having 20 or less carbon atoms, n is each independently an integer of 0 to 3, and m is each independently an integer of 0 to 4. In addition, examples of the substituent in the case of "substitutable" or "substituted" include aryl, heteroaryl, alkyl or cycloalkyl.

式(ETM-1-2)中，R¹¹及R¹²分别独立地为氢、烷基、环烷基、可经取代的芳基、经取代的硅烷基、可经取代的含氮杂环或氰基的至少一者，R¹³～R¹⁶分别独立地为可经取代的烷基、可经取代的环烷基或可经取代的芳基，X¹为可经取代的碳数20以下的亚芳基，而且，n分别独立地为0～3的整数。另外，作为“可经取代”或“经取代”时的取代基，可列举：芳基、杂芳基、烷基或环烷基等。In formula (ETM-1-2), R¹¹ and R¹² are each independently hydrogen, alkyl, cycloalkyl, aryl, substituted silyl, substituted nitrogen-containing heterocyclic ring or cyano, R¹³ to R¹⁶ are each independently substituted alkyl, cycloalkyl or aryl, X¹ is an arylene group having 20 or less carbon atoms which may be substituted, and n is each independently an integer of 0 to 3. In addition, examples of the substituents in the case of "substitutable" or "substituted" include aryl, heteroaryl, alkyl or cycloalkyl.

作为X¹的具体例，可列举下述式(X-1)～式(X-9)的任一者所表示的二价基。Specific examples of^X1 include divalent groups represented by any one of the following formulae (X-1) to (X-9).

(各式中，R^a分别独立地为烷基、环烷基或可经取代的苯基，*表示键结位置)(In each formula,^Ra is independently an alkyl group, a cycloalkyl group or a phenyl group which may be substituted, and * indicates a bonding position)

作为所述硼烷衍生物的具体例，例如可列举以下的化合物。Specific examples of the borane derivatives include the following compounds.

所述硼烷衍生物可使用现有的原料与现有的合成方法来制造。The borane derivatives can be prepared using existing raw materials and existing synthesis methods.

＜吡啶衍生物＞＜Pyridine derivatives＞

吡啶衍生物例如为下述式(ETM-2)所表示的化合物，优选为式(ETM-2-1)或式(ETM-2-2)所表示的化合物。The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2).

φ—(吡啶系取代基)n (ETM-2)φ—(pyridine substituent)n (ETM-2)

φ为n价的芳基环(优选为n价的苯环、萘环、蒽环、芴环、苯并芴环、非那烯环、菲环或三亚苯环)，n为1～4的整数。φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1-4.

在式(ETM-2-1)中，R¹¹～R¹⁸分别独立地为氢、烷基(优选为碳数1～24的烷基)、环烷基(优选为碳数3～12的环烷基)或芳基(优选为碳数6～30的芳基)。In formula (ETM-2-1), R¹¹ to R¹⁸ are each independently hydrogen, alkyl (preferably an alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably a cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably an aryl having 6 to 30 carbon atoms).

在式(ETM-2-2)中，R¹¹及R¹²分别独立地为氢、烷基(优选为碳数1～24的烷基)、环烷基(优选为碳数3～12的环烷基)或芳基(优选为碳数6～30的芳基)，R¹¹及R¹²可键结而形成环。In formula (ETM-2-2), R¹¹ and R¹² are each independently hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group (preferably an aryl group having 6 to 30 carbon atoms), and R¹¹ and R¹² may be bonded to form a ring.

在各式中，“吡啶系取代基”为下述式(Py-1)～式(Py-15)的任一者(式中的*表示键结位置)，吡啶系取代基可分别独立地由碳数1～4的烷基或碳数5～10的环烷基取代。作为具体例，可列举甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基等，优选为甲基。另外，吡啶系取代基可经由亚苯基或亚萘基而与各式中的φ、蒽环或芴环键结。In each formula, the "pyridine substituent" is any one of the following formulas (Py-1) to (Py-15) (where * represents the bonding position), and the pyridine substituent may be independently substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, preferably methyl. In addition, the pyridine substituent may be bonded to the φ, anthracene ring or fluorene ring in each formula via a phenylene group or a naphthylene group.

吡啶系取代基为式(Py-1)～式(Py-15)的任一者(式中的*表示键结位置)，这些中，优选为下述式(Py-21)～式(Py-44)的任一者。The pyridine-based substituent is any one of formula (Py-1) to formula (Py-15) (wherein * represents a bonding position), and among these, any one of the following formulas (Py-21) to (Py-44) is preferred.

各吡啶衍生物中的至少一个氢可由氘取代，另外，式(ETM-2-1)及式(ETM-2-2)中的两个“吡啶系取代基”中的其中一者可由芳基取代。At least one hydrogen in each pyridine derivative may be substituted by deuterium, and one of the two "pyridine substituents" in Formula (ETM-2-1) and Formula (ETM-2-2) may be substituted by an aryl group.

R¹¹～R¹⁸中的“烷基”可为直链及支链的任一种，例如可列举碳数1～24的直链烷基或碳数3～24的支链烷基。优选的“烷基”为碳数1～18的烷基(碳数3～18的支链烷基)。更优选的“烷基”为碳数1～12的烷基(碳数3～12的支链烷基)。进而优选的“烷基”为碳数1～6的烷基(碳数3～6的支链烷基)。特别优选的“烷基”为碳数1～4的烷基(碳数3～4的支链烷基)。The "alkyl" in R¹¹ to R¹⁸ may be any of a linear chain and a branched chain, and examples thereof include a linear chain alkyl group having 1 to 24 carbon atoms and a branched chain alkyl group having 3 to 24 carbon atoms. A preferred "alkyl group" is an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms). A more preferred "alkyl group" is an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms). A further preferred "alkyl group" is an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms).

作为具体的“烷基”，可列举：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、正己基、1-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、正庚基、1-甲基己基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、2,6-二甲基-4-庚基、3,5,5-三甲基己基、正癸基、正十一基、1-甲基癸基、正十二基、正十三基、1-己基庚基、正十四基、正十五基、正十六基、正十七基、正十八基、正二十基等。Specific examples of the “alkyl group” include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-icosyl.

作为在吡啶系取代基中进行取代的碳数1～4的烷基，可引用所述烷基的说明。As the alkyl group having 1 to 4 carbon atoms substituting in the pyridine-based substituent, the description of the alkyl group mentioned above can be cited.

作为R¹¹～R¹⁸中的“环烷基”，例如可列举碳数3～12的环烷基。优选的“环烷基”为碳数3～10的环烷基。更优选的“环烷基”为碳数3～8的环烷基。进而优选的“环烷基”为碳数3～6的环烷基。Examples of the "cycloalkyl" in R¹¹ to R¹⁸ include cycloalkyl groups having 3 to 12 carbon atoms. Preferred "cycloalkyl" groups are cycloalkyl groups having 3 to 10 carbon atoms. More preferred "cycloalkyl" groups are cycloalkyl groups having 3 to 8 carbon atoms. Further preferred "cycloalkyl" groups are cycloalkyl groups having 3 to 6 carbon atoms.

作为具体的“环烷基”，可列举：环丙基、环丁基、环戊基、环己基、甲基环戊基、环庚基、甲基环己基、环辛基或二甲基环己基等。Specific examples of the "cycloalkyl group" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl and dimethylcyclohexyl.

作为R¹¹～R¹⁸中的“芳基”，优选的芳基为碳数6～30的芳基，更优选的芳基为碳数6～18的芳基，进而优选为碳数6～14的芳基，特别优选为碳数6～12的芳基。As the "aryl group" in R¹¹ to R¹⁸ , a preferred aryl group is an aryl group having 6 to 30 carbon atoms, a more preferred aryl group is an aryl group having 6 to 18 carbon atoms, a further preferred aryl group is an aryl group having 6 to 14 carbon atoms, and a particularly preferred aryl group is an aryl group having 6 to 12 carbon atoms.

作为具体的“碳数6～30的芳基”，可列举：作为单环系芳基的苯基，作为缩合二环系芳基的(1-、2-)萘基，作为缩合三环系芳基的苊-(1-、3-、4-、5-)基、芴-(1-、2-、3-、4-、9-)基、非那烯-(1-、2-)基、(1-、2-、3-、4-、9-)菲基，作为缩合四环系芳基的三亚苯-(1-、2-)基、芘-(1-、2-、4-)基、并四苯-(1-、2-、5-)基，作为缩合五环系芳基的苝-(1-、2-、3-)基、并五苯-(1-、2-、5-、6-)基等。Specific examples of the “aryl group having 6 to 30 carbon atoms” include: phenyl as a monocyclic aromatic group, (1-, 2-)naphthyl as a condensed bicyclic aromatic group, acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthren-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl as a condensed tricyclic aromatic group, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetracene-(1-, 2-, 5-)yl as a condensed tetracyclic aromatic group, and perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl as a condensed pentacyclic aromatic group.

优选的“碳数6～30的芳基”可列举苯基、萘基、菲基、基或三亚苯基等，进而优选为可列举苯基、1-萘基、2-萘基或菲基，特别优选为可列举苯基、1-萘基或2-萘基。Preferred "aryl group having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthrenyl, Preferably, there are phenyl, 1-naphthyl, 2-naphthyl and phenanthryl, and particularly preferably, there are phenyl, 1-naphthyl and 2-naphthyl.

式(ETM-2-2)中的R¹¹及R¹²可键结而形成环，其结果，可在芴骨架的5元环上螺键结环丁烷、环戊烷、环戊烯、环戊二烯、环己烷、芴或茚等。R¹¹ and R¹² in formula (ETM-2-2) may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene or the like may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

作为所述吡啶衍生物的具体例，例如可列举以下的化合物。Specific examples of the pyridine derivatives include the following compounds.

所述吡啶衍生物可使用现有的原料与现有的合成方法来制造。The pyridine derivatives can be produced using existing raw materials and existing synthesis methods.

＜荧蒽衍生物＞＜Fluoranthene derivatives＞

荧蒽衍生物例如为下述式(ETM-3)所表示的化合物，详细而言在国际公开第2010/134352号中进行了公开。The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and its details are disclosed in International Publication No. 2010/134352.

式(ETM-3)中，X¹²～X²¹表示氢、卤素、直链、支链或环状的烷基、直链、支链或环状的烷氧基、经取代或未经取代的芳基、或者经取代或未经取代的杂芳基。此处，作为经取代时的取代基，可列举：芳基、杂芳基、烷基或环烷基等。In formula (ETM-3),^X12 to^X21 represent hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituents include aryl, heteroaryl, alkyl or cycloalkyl.

作为所述荧蒽衍生物的具体例，例如可列举以下的化合物。Specific examples of the fluoranthene derivatives include the following compounds.

＜BO系衍生物＞＜BO derivatives＞

BO系衍生物例如为下述式(ETM-4)所表示的多环芳香族化合物、或具有多个下述式(ETM-4)所表示的结构的多环芳香族化合物的多聚体。The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4) or a multimer of polycyclic aromatic compounds having a plurality of structures represented by the following formula (ETM-4).

R¹～R¹¹分别独立地为氢、芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、烷基、环烷基、烷氧基或芳氧基，它们中的至少一个氢可由芳基、杂芳基、烷基或环烷基取代。R¹ to R¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in them may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group.

另外，R¹～R¹¹中的邻接的基彼此可键结并与a环、b环或c环一起形成芳基环或杂芳基环，所形成的环中的至少一个氢可由芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、烷基、环烷基、烷氧基或芳氧基取代，它们中的至少一个氢可由芳基、杂芳基、烷基或环烷基取代。In addition, adjacent groups in R¹ to R¹¹ may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring may be substituted by an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkoxy group or an aryloxy group, and at least one hydrogen in them may be substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group.

另外，式(ETM-4)所表示的化合物或结构中的至少一个氢可由卤素或氘取代。In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted by halogen or deuterium.

关于式(ETM-4)中的取代基或环形成的形态的说明，可引用式(D)或式(D-a)等所表示的多环芳香族化合物的说明。Regarding the description of the substituents or the ring formation form in the formula (ETM-4), the description of the polycyclic aromatic compounds represented by the formula (D) or the formula (D-a) can be cited.

作为所述BO系衍生物的具体例，例如可列举以下的化合物。Specific examples of the BO derivatives include the following compounds.

所述BO系衍生物可使用现有的原料与现有的合成方法来制造。The BO derivatives can be produced using existing raw materials and existing synthesis methods.

＜蒽衍生物＞＜Anthracene derivatives＞

蒽衍生物例如为下述式(ETM-5)所表示的化合物。The anthracene derivative is, for example, a compound represented by the following formula (ETM-5).

Ar¹分别独立地为单键、二价的苯、萘、蒽、芴或非那烯。Ar^1's are each independently a single bond, a divalent benzene, naphthalene, anthracene, fluorene or phenalene.

Ar²分别独立地为碳数6～20的芳基，优选为碳数6～16的芳基，更优选为碳数6～12的芳基，特别优选为碳数6～10的芳基。作为“碳数6～20的芳基”的具体例，可列举：作为单环系芳基的苯基、(邻、间、对)甲苯基、(2,3-、2,4-、2,5-、2,6-、3,4-、3,5-)二甲苯基、均三甲苯基(2,4,6-三甲基苯基)、(邻、间、对)枯烯基，作为二环系芳基的(2-、3-、4-)联苯基，作为缩合二环系芳基的(1-、2-)萘基，作为三环系芳基的三联苯基(间三联苯-2'-基、间三联苯-4'-基、间三联苯-5'-基、邻三联苯-3'-基、邻三联苯-4'-基、对三联苯-2'-基、间三联苯-2-基、间三联苯-3-基、间三联苯-4-基、邻三联苯-2-基、邻三联苯-3-基、邻三联苯-4-基、对三联苯-2-基、对三联苯-3-基、对三联苯-4-基)，作为缩合三环系芳基的蒽-(1-、2-、9-)基、苊-(1-、3-、4-、5-)基、芴-(1-、2-、3-、4-、9-)基、非那烯-(1-、2-)基、(1-、2-、3-、4-、9-)菲基，作为缩合四环系芳基的三亚苯-(1-、2-)基、芘-(1-、2-、4-)基、并四苯-(1-、2-、5-)基，作为缩合五环系芳基的苝-(1-、2-、3-)基等。作为“碳数6～10的芳基”的具体例，可列举：苯基、联苯基、萘基、三联苯基、蒽基、苊基、芴基、非那烯基、菲基、三亚苯基、芘基、并四苯基、苝基等。Ar² is each independently an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples of the "aryl group having 6 to 20 carbon atoms" include: phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-)cumenyl as monocyclic aromatic groups; (2-, 3-, 4-)biphenyl as bicyclic aromatic groups; (1-, 2-)naphthyl as condensed bicyclic aromatic groups; terphenyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2'-yl, m-terphenyl-3'-yl, m-terphenyl-4'-yl) as tricyclic aromatic groups. as condensed tricyclic aromatic groups, such as anthracene-(1-, 2-, 9-)yl, acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl; as condensed tetracyclic aromatic groups, such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl; as condensed pentacyclic aromatic groups, such as perylene-(1-, 2-, 3-)yl. Specific examples of the "aryl group having 6 to 10 carbon atoms" include phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenaltenyl, phenanthrenyl, triphenylene, pyrenyl, naphthacene, and perylenyl.

R¹～R⁴分别独立地为氢、碳数1～6的烷基、碳数3至6的环烷基或碳数6～20的芳基。R¹ to R⁴ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

R¹～R⁴中的碳数1～6的烷基可为直链及支链的任一种。即，为碳数1～6的直链烷基或碳数3～6的支链烷基。更优选为碳数1～4的烷基(碳数3～4的支链烷基)。作为具体例，可列举甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、正己基、1-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基或2-乙基丁基等，优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基，更优选为甲基、乙基或叔丁基。The alkyl group having 1 to 6 carbon atoms in R¹ to R⁴ may be any of a straight chain and a branched chain. That is, it is a straight chain alkyl group having 1 to 6 carbon atoms or a branched chain alkyl group having 3 to 6 carbon atoms. More preferably, it is an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms). Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an n-hexyl group, a 1-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, or a 2-ethylbutyl group. Preferably, it is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group. More preferably, it is a methyl group, an ethyl group, or a tert-butyl group.

作为R¹～R⁴中的碳数3～6的环烷基的具体例，可列举：环丙基、环丁基、环戊基、环己基、甲基环戊基、环庚基、甲基环己基、环辛基或二甲基环己基等。Specific examples of the cycloalkyl group having 3 to 6 carbon atoms in R¹ to R⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl and dimethylcyclohexyl.

关于R¹～R⁴中的碳数6～20的芳基，优选为碳数6～16的芳基，更优选为碳数6～12的芳基，特别优选为碳数6～10的芳基。作为“碳数6～20的芳基”的具体例，可引用Ar²中的“碳数6～20的芳基”的具体例。优选的“碳数6～20的芳基”为苯基、联苯基、三联苯基或萘基，更优选为苯基、联苯基、1-萘基、2-萘基或间三联苯-5'-基，进而优选为苯基、联苯基、1-萘基或2-萘基，最优选为苯基。The aryl group having 6 to 20 carbon atoms in R¹ to R⁴ is preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples of the "aryl group having 6 to 20 carbon atoms" include the specific examples of the "aryl group having 6 to 20 carbon atoms" in Ar^2. Preferred "aryl group having 6 to 20 carbon atoms" is phenyl, biphenyl, terphenyl or naphthyl, more preferably phenyl, biphenyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl, further preferably phenyl, biphenyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

作为这些蒽衍生物的具体例，例如可列举以下的化合物。Specific examples of these anthracene derivatives include the following compounds.

这些蒽衍生物可使用现有的原料与现有的合成方法来制造。These anthracene derivatives can be produced using existing raw materials and existing synthesis methods.

＜苯并芴衍生物＞＜Benzofluorene derivatives＞

苯并芴衍生物例如为下述式(ETM-6)所表示的化合物。The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Ar¹分别独立地为碳数6～20的芳基，可引用与式(ETM-5)的Ar²中的“碳数6～20的芳基”相同的说明。优选为碳数6～16的芳基，更优选为碳数6～12的芳基，特别优选为碳数6～10的芳基。作为具体例，可列举：苯基、联苯基、萘基、三联苯基、蒽基、苊基、芴基、非那烯基、菲基、三亚苯基、芘基、并四苯基、苝基等。Ar¹ is independently an aryl group having 6 to 20 carbon atoms, and the same description as for the "aryl group having 6 to 20 carbon atoms" in Ar² of formula (ETM-5) can be cited. Preferably, it is an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples thereof include phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenanthrenyl, phenanthrenyl, triphenylene, pyrenyl, naphthphenylene, perylene, and the like.

Ar²分别独立地为氢、烷基(优选为碳数1～24的烷基)、环烷基(优选为碳数3～12的环烷基)或芳基(优选为碳数6～30的芳基)，两个Ar²可键结而形成环。Ar^2's are each independently hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group (preferably an aryl group having 6 to 30 carbon atoms), and two Ar^2's may be bonded to form a ring.

Ar²中的“烷基”可为直链及支链的任一种，例如可列举碳数1～24的直链烷基或碳数3～24的支链烷基。优选的“烷基”为碳数1～18的烷基(碳数3～18的支链烷基)。更优选的“烷基”为碳数1～12的烷基(碳数3～12的支链烷基)。进而优选的“烷基”为碳数1～6的烷基(碳数3～6的支链烷基)。特别优选的“烷基”为碳数1～4的烷基(碳数3～4的支链烷基)。作为具体的“烷基”，可列举：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、正己基、1-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、正庚基、1-甲基己基等。The "alkyl" in Ar² may be any of a straight chain and a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. A preferred "alkyl group" is an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms). A more preferred "alkyl group" is an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms). A further preferred "alkyl group" is an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms). Specific examples of "alkyl groups" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

作为Ar²中的“环烷基”，例如可列举碳数3～12的环烷基。优选的“环烷基”为碳数3～10的环烷基。更优选的“环烷基”为碳数3～8的环烷基。进而优选的“环烷基”为碳数3～6的环烷基。作为具体的“环烷基”，可列举：环丙基、环丁基、环戊基、环己基、甲基环戊基、环庚基、甲基环己基、环辛基或二甲基环己基等。Examples of the "cycloalkyl" in^Ar2 include cycloalkyl groups having 3 to 12 carbon atoms. Preferred "cycloalkyl" groups are cycloalkyl groups having 3 to 10 carbon atoms. More preferred "cycloalkyl" groups are cycloalkyl groups having 3 to 8 carbon atoms. Further preferred "cycloalkyl" groups are cycloalkyl groups having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

作为Ar²中的“芳基”，优选的芳基为碳数6～30的芳基，更优选的芳基为碳数6～18的芳基，进而优选为碳数6～14的芳基，特别优选为碳数6～12的芳基。As the "aryl group" in^Ar2 , a preferred aryl group is an aryl group having 6 to 30 carbon atoms, a more preferred aryl group is an aryl group having 6 to 18 carbon atoms, a further preferred aryl group is an aryl group having 6 to 14 carbon atoms, and a particularly preferred aryl group is an aryl group having 6 to 12 carbon atoms.

作为具体的“碳数6～30的芳基”，可列举：苯基、萘基、苊基、芴基、非那烯基、菲基、三亚苯基、芘基、并四苯基、苝基、并五苯基等。Specific examples of the "aryl group having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthenyl, fluorenyl, phenaltenyl, phenanthrenyl, triphenylene, pyrenyl, naphthacene, perylenyl, and pentacene.

两个Ar²可键结而形成环，其结果，可在芴骨架的5元环上螺键结环丁烷、环戊烷、环戊烯、环戊二烯、环己烷、芴或茚等。Two Ar^2's may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene or the like may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

作为所述苯并芴衍生物的具体例，例如可列举以下的化合物。Specific examples of the benzofluorene derivatives include the following compounds.

所述苯并芴衍生物可使用现有的原料与现有的合成方法来制造。The benzofluorene derivatives can be produced using existing raw materials and existing synthesis methods.

＜氧化膦衍生物＞＜Phosphine oxide derivatives＞

氧化膦衍生物例如为下述式(ETM-7-1)所表示的化合物。详细情况也在国际公开第2013/079217号及国际公开第2013/079678号中进行了记载。The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). The details are also described in International Publication Nos. 2013/079217 and 2013/079678.

R⁵为经取代或未经取代的碳数1～20的烷基、碳数3～16的环烷基、碳数6～20的芳基或碳数5～20的杂芳基，^R5 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 carbon atoms,

R⁶为CN、经取代或未经取代的碳数1～20的烷基、碳数3～16的环烷基、碳数1～20的杂烷基、碳数6～20的芳基、碳数5～20的杂芳基、碳数1～20的烷氧基或碳数6～20的芳氧基，^R6 is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, or aryloxy having 6 to 20 carbon atoms,

R⁷及R⁸分别独立地为经取代或未经取代的碳数6～20的芳基或碳数5～20的杂芳基，^R7 and^R8 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms,

R⁹为氧或硫，R⁹ is oxygen or sulfur,

j为0或1，k为0或1，r为0～4的整数，q为1～3的整数。j is 0 or 1, k is 0 or 1, r is an integer of 0-4, and q is an integer of 1-3.

此处，作为经取代时的取代基，可列举：芳基、杂芳基、烷基或环烷基等。Here, examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

氧化膦衍生物例如可为下述式(ETM-7-2)所表示的化合物。The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).

R¹～R³可相同也可不同，选自氢、烷基、环烷基、芳烷基、烯基、环烯基、炔基、烷氧基、烷硫基、环烷硫基、芳基醚(芳基醚基)、芳硫基醚(芳硫基醚基)、芳基、杂环基、卤素、氰基、甲酰基、羰基、羧基、氨基、硝基、硅烷基及在与邻接取代基之间所形成的稠环中。^R1 to^R3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), arylthio ether (arylthio ether group), aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silane and a condensed ring formed with an adjacent substituent.

Ar¹可相同也可不同，且为亚芳基或亚杂芳基。Ar²可相同也可不同，且为芳基或杂芳基。其中，Ar¹及Ar²中的至少一者具有取代基，或在与邻接取代基之间形成稠环。n为0～3的整数，当n为0时，并不存在不饱和结构部分，当n为3时，并不存在R¹。Ar¹ may be the same or different and is an arylene group or a heteroarylene group. Ar² may be the same or different and is an aryl group or a heteroaryl group. At least one of Ar¹ and Ar² has a substituent or forms a condensed ring with an adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structure part. When n is 3, there is no R¹ .

这些取代基内，所谓烷基，例如表示甲基、乙基、丙基、丁基等饱和脂肪族烃基，所述烷基可未经取代也可经取代。经取代时的取代基并无特别限制，例如可列举烷基、芳基、杂环基等，此方面在以下的记载中也共通。另外，烷基的碳数并无特别限定，就获取的容易性或成本的方面而言，通常为1～20的范围。Among these substituents, the so-called alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, a butyl group, etc., and the alkyl group may be unsubstituted or substituted. The substituent group when substituted is not particularly limited, and examples thereof include an alkyl group, an aryl group, a heterocyclic group, etc., which are also common in the following descriptions. In addition, the number of carbon atoms in the alkyl group is not particularly limited, and is generally in the range of 1 to 20 in terms of ease of acquisition or cost.

另外，所谓环烷基，例如表示环丙基、环己基、降冰片基、金刚烷基等饱和脂环式烃基，所述环烷基可未经取代也可经取代。烷基部分的碳数并无特别限定，通常为3～20的范围。The cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, and the cycloalkyl group may be unsubstituted or substituted. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20.

另外，所谓芳烷基，例如表示苄基、苯基乙基等经由脂肪族烃的芳香族烃基，脂肪族烃与芳香族烃均可未经取代也可经取代。脂肪族部分的碳数并无特别限定，通常为1～20的范围。The term "aralkyl" refers to an aromatic hydrocarbon group such as benzyl or phenylethyl, which is substituted by an aliphatic hydrocarbon. The aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, but is usually in the range of 1 to 20.

另外，所谓烯基，例如表示乙烯基、烯丙基、丁二烯基等包含双键的不饱和脂肪族烃基，所述烯基可未经取代也可经取代。烯基的碳数并无特别限定，通常为2～20的范围。In addition, the alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, and a butadienyl group, and the alkenyl group may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

另外，所谓环烯基，例如表示环戊烯基、环戊二烯基、环己烯基等包含双键的不饱和脂环式烃基，所述环烯基可未经取代也可经取代。The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, and a cyclohexenyl group, and the cycloalkenyl group may be unsubstituted or substituted.

另外，所谓炔基，例如表示乙炔基等包含三键的不饱和脂肪族烃基，所述炔基可未经取代也可经取代。炔基的碳数并无特别限定，通常为2～20的范围。The term "alkynyl group" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group, and the alkynyl group may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is generally in the range of 2 to 20.

另外，所谓烷氧基，例如表示甲氧基等经由醚键的脂肪族烃基，脂肪族烃基可未经取代也可经取代。烷氧基的碳数并无特别限定，通常为1～20的范围。The term "alkoxy group" refers to an aliphatic hydrocarbon group such as a methoxy group through an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

另外，所谓烷硫基为烷氧基的醚键的氧原子被取代为硫原子的基。The alkylthio group is a group in which the oxygen atom in the ether bond of an alkoxy group is substituted with a sulfur atom.

另外，所谓环烷硫基为环烷氧基的醚键的氧原子被取代为硫原子的基。The cycloalkylthio group is a group in which the oxygen atom in the ether bond of a cycloalkyloxy group is substituted with a sulfur atom.

另外，所谓芳基醚，例如表示苯氧基等经由醚键的芳香族烃基，芳香族烃基可未经取代也可经取代。芳基醚的碳数并无特别限定，通常为6～40的范围。The term "aryl ether" refers to an aromatic hydrocarbon group such as a phenoxy group through an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether is not particularly limited, but is generally in the range of 6 to 40.

另外，所谓芳硫基醚为芳基醚的醚键的氧原子被取代为硫原子的基。The arylthio ether is a group in which the oxygen atom in the ether bond of the aryl ether is substituted with a sulfur atom.

另外，所谓芳基，例如表示苯基、萘基、联苯基、菲基、三联苯基、芘基等芳香族烃基。芳基可未经取代也可经取代。芳基的碳数并无特别限定，通常为6～40的范围。In addition, the so-called aryl group refers to aromatic hydrocarbon groups such as phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, and pyrenyl. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

另外，所谓杂环基，例如表示呋喃基、噻吩基、噁唑基、吡啶基、喹啉基、咔唑基等具有碳以外的原子的环状结构基，所述杂环基可未经取代也可经取代。杂环基的碳数并无特别限定，通常为2～30的范围。In addition, the heterocyclic group refers to a cyclic structural group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolyl, carbazolyl, etc., and the heterocyclic group may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

所谓卤素，表示氟、氯、溴、碘。The halogen refers to fluorine, chlorine, bromine and iodine.

在甲酰基、羰基、氨基中也可包含由脂肪族烃、脂环式烃、芳香族烃、杂环等取代的基。The formyl group, carbonyl group, and amino group may include a group substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocycle, or the like.

另外，脂肪族烃、脂环式烃、芳香族烃、杂环可未经取代也可经取代。In addition, the aliphatic hydrocarbon, the alicyclic hydrocarbon, the aromatic hydrocarbon, and the heterocycle may be unsubstituted or substituted.

所谓硅烷基，例如表示三甲基硅烷基等硅化合物基，所述硅烷基可未经取代也可经取代。硅烷基的碳数并无特别限定，通常为3～20的范围。另外，硅数通常为1～6。The silyl group refers to a silicon compound group such as a trimethylsilyl group, and the silyl group may be unsubstituted or substituted. The carbon number of the silyl group is not particularly limited, but is usually in the range of 3 to 20. The silicon number is usually 1 to 6.

所谓在与邻接取代基之间所形成的稠环例如为在Ar¹与R²、Ar¹与R³、Ar²与R²、Ar²与R³、R²与R³、Ar¹与Ar²等之间所形成的共轭或非共轭的稠环。此处，当n为1时，两个R¹彼此可形成共轭或非共轭的稠环。这些稠环可在环内结构中包含氮原子、氧原子、硫原子，也可进一步与其他环缩合。The so-called condensed ring formed between adjacent substituents is, for example, a conjugated or non-conjugated condensed ring formed between^Ar1 and^R2 ,^Ar1 and^R3 ,^Ar2 and^R2 ,^Ar2 and^R3 ,^R2 and^R3 ,^Ar1 and^Ar2, etc. Here, when n is 1, two^R1s may form a conjugated or non-conjugated condensed ring. These condensed rings may contain nitrogen atoms, oxygen atoms, sulfur atoms in the ring structure, and may be further condensed with other rings.

作为所述氧化膦衍生物的具体例，例如可列举以下的化合物。Specific examples of the phosphine oxide derivatives include the following compounds.

所述氧化膦衍生物可使用现有的原料与现有的合成方法来制造。The phosphine oxide derivatives can be produced using existing raw materials and existing synthesis methods.

＜嘧啶衍生物＞＜Pyrimidine derivatives＞

嘧啶衍生物例如为下述式(ETM-8)所表示的化合物，优选为下述式(ETM-8-1)所表示的化合物。详细情况也在国际公开第2011/021689号中进行了记载。The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). The details are also described in International Publication No. 2011/021689.

Ar分别独立地为可经取代的芳基或可经取代的杂芳基。n为1～4的整数，优选为1～3的整数，更优选为2或3。Ar is independently an aryl group which may be substituted or a heteroaryl group which may be substituted. n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

作为“可经取代的芳基”的“芳基”，例如可列举碳数6～30的芳基，优选为碳数6～24的芳基，更优选为碳数6～20的芳基，进而优选为碳数6～12的芳基。Examples of the "aryl group" of the "aryl group which may be substituted" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and still more preferably an aryl group having 6 to 12 carbon atoms.

作为具体的“芳基”，可列举：作为单环系芳基的苯基，作为二环系芳基的(2-、3-、4-)联苯基，作为缩合二环系芳基的(1-、2-)萘基，作为三环系芳基的三联苯基(间三联苯-2'-基、间三联苯-4'-基、间三联苯-5'-基、邻三联苯-3'-基、邻三联苯-4'-基、对三联苯-2'-基、间三联苯-2-基、间三联苯-3-基、间三联苯-4-基、邻三联苯-2-基、邻三联苯-3-基、邻三联苯-4-基、对三联苯-2-基、对三联苯-3-基、对三联苯-4-基)，作为缩合三环系芳基的苊-(1-、3-、4-、5-)基、芴-(1-、2-、3-、4-、9-)基、非那烯-(1-、2-)基、(1-、2-、3-、4-、9-)菲基，作为四环系芳基的四联苯基(5'-苯基-间三联苯-2-基、5'-苯基-间三联苯-3-基、5'-苯基-间三联苯-4-基、间四联苯基)，作为缩合四环系芳基的三亚苯-(1-、2-)基、芘-(1-、2-、4-)基、并四苯-(1-、2-、5-)基，作为缩合五环系芳基的苝-(1-、2-、3-)基、并五苯-(1-、2-、5-、6-)基等。Specific examples of the "aryl group" include: phenyl as a monocyclic aromatic group, (2-, 3-, 4-)biphenyl as a bicyclic aromatic group, (1-, 2-)naphthyl as a condensed bicyclic aromatic group, terphenyl groups (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aromatic groups. as a tetracyclic aromatic group such as acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthren-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl; as a tetracyclic aromatic group such as quaternaryl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaternaryl); as a condensed tetracyclic aromatic group such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetracene-(1-, 2-, 5-)yl; as a condensed pentacyclic aromatic group such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl;

作为“可经取代的杂芳基”的“杂芳基”，例如可列举碳数2～30的杂芳基，优选为碳数2～25的杂芳基，更优选为碳数2～20的杂芳基，进而优选为碳数2～15的杂芳基，特别优选为碳数2～10的杂芳基。另外，作为杂芳基，例如可列举除碳以外含有1个至5个选自氧、硫及氮中的杂原子作为环构成原子的杂环等。Examples of the “heteroaryl group” of the “heteroaryl group which may be substituted” include heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, further preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms other than carbon.

作为具体的杂芳基，例如可列举：呋喃基、噻吩基、吡咯基、噁唑基、异噁唑基、噻唑基、异噻唑基、咪唑基、吡唑基、噁二唑基、呋咱基、噻二唑基、三唑基、四唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、苯并呋喃基、异苯并呋喃基、苯并[b]噻吩基、吲哚基、异吲哚基、1H-吲唑基、苯并咪唑基、苯并噁唑基、苯并噻唑基、1H-苯并三唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹噁啉基、酞嗪基、萘啶基、嘌呤基、蝶啶基、咔唑基、吖啶基、吩噁嗪基、吩噻嗪基、吩嗪基、吩噁噻基、噻蒽基、吲嗪基等。Specific examples of the heteroaryl group include furanyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiyl, thianthrenyl, and indolizinyl.

另外，所述芳基及杂芳基可经取代，可分别例如由所述芳基或杂芳基取代。In addition, the aryl group and the heteroaryl group may be substituted, for example, by the aryl group or the heteroaryl group, respectively.

作为所述嘧啶衍生物的具体例，例如可列举以下的化合物。Specific examples of the pyrimidine derivatives include the following compounds.

所述嘧啶衍生物可使用现有的原料与现有的合成方法来制造。The pyrimidine derivatives can be produced using existing raw materials and existing synthesis methods.

＜芳基腈衍生物＞＜Aryl nitrile derivatives＞

芳基腈衍生物例如为下述式(ETM-9)所表示的化合物、或多个其通过单键等而键结所得的多聚体。详情情况在美国申请公开第2014/0197386号说明书中进行了记载。The aryl nitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of the compounds are bonded via a single bond, etc. The details are described in the specification of US Application Publication No. 2014/0197386.

就快速的电子传输性的观点而言，Ar_ni优选为碳数多，就高T1的观点而言，Ar_ni优选为碳数少。具体而言，在用于与发光层邻接的层时，优选为T1高，从而Ar_ni为碳数6～20的芳基，优选为碳数6～14的芳基，更优选为碳数6～10的芳基。另外，关于腈基的取代个数n，就高T1的观点而言，以多为宜，就高S1的观点而言，以少为宜。具体而言，腈基的取代个数n为1～4的整数，优选为1～3的整数，更优选为1～2的整数，进而优选为1。From the perspective of rapid electron transport, Ar_ni is preferably a carbon number with a large number, and from the perspective of high T1, Ar_ni is preferably a carbon number with a small number. Specifically, when used in a layer adjacent to a light-emitting layer, it is preferably a high T1, so that Ar_ni is an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 14 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. In addition, regarding the number of substitutions n of the nitrile group, from the perspective of high T1, it is preferably more, and from the perspective of high S1, it is preferably less. Specifically, the number of substitutions n of the nitrile group is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and further preferably 1.

Ar分别独立地为可经取代的芳基或可经取代的杂芳基。就高S1及高T1的观点而言，优选为施体性的杂芳基，由于用作电子传输层，因此施体性的杂芳基以少为宜。就电荷传输性的观点而言，优选为碳数多的芳基或杂芳基，优选为具有大量取代基。具体而言，Ar的取代个数m为1～4的整数，优选为1～3的整数，更优选为1～2。Ar is independently a substituted aryl group or a substituted heteroaryl group. From the viewpoint of high S1 and high T1, a donor heteroaryl group is preferred. Since it is used as an electron transport layer, the donor heteroaryl group is preferably less. From the viewpoint of charge transport, an aryl or heteroaryl group with a large number of carbon atoms is preferred, preferably with a large number of substituents. Specifically, the number of substitutions m of Ar is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

作为“可经取代的芳基”的“芳基”，例如可列举碳数6～30的芳基，优选为碳数6～24的芳基，更优选为碳数6～20的芳基，进而优选为碳数6～12的芳基。Examples of the "aryl group" of the "aryl group which may be substituted" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and still more preferably an aryl group having 6 to 12 carbon atoms.

作为具体的“芳基”，可列举：作为单环系芳基的苯基，作为二环系芳基的(2-、3-、4-)联苯基，作为缩合二环系芳基的(1-、2-)萘基，作为三环系芳基的三联苯基(间三联苯-2'-基、间三联苯-4'-基、间三联苯-5'-基、邻三联苯-3'-基、邻三联苯-4'-基、对三联苯-2'-基、间三联苯-2-基、间三联苯-3-基、间三联苯-4-基、邻三联苯-2-基、邻三联苯-3-基、邻三联苯-4-基、对三联苯-2-基、对三联苯-3-基、对三联苯-4-基)，作为缩合三环系芳基的苊-(1-、3-、4-、5-)基、芴-(1-、2-、3-、4-、9-)基、非那烯-(1-、2-)基、(1-、2-、3-、4-、9-)菲基，作为四环系芳基的四联苯基(5'-苯基-间三联苯-2-基、5'-苯基-间三联苯-3-基、5'-苯基-间三联苯-4-基、间四联苯基)，作为缩合四环系芳基的三亚苯-(1-、2-)基、芘-(1-、2-、4-)基、并四苯-(1-、2-、5-)基，作为缩合五环系芳基的苝-(1-、2-、3-)基、并五苯-(1-、2-、5-、6-)基等。Specific examples of the "aryl group" include: phenyl as a monocyclic aromatic group, (2-, 3-, 4-)biphenyl as a bicyclic aromatic group, (1-, 2-)naphthyl as a condensed bicyclic aromatic group, terphenyl groups (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aromatic groups. as a tetracyclic aromatic group such as acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthren-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl; as a tetracyclic aromatic group such as quaternaryl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaternaryl); as a condensed tetracyclic aromatic group such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetracene-(1-, 2-, 5-)yl; as a condensed pentacyclic aromatic group such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl;

作为“可经取代的杂芳基”的“杂芳基”，例如可列举碳数2～30的杂芳基，优选为碳数2～25的杂芳基，更优选为碳数2～20的杂芳基，进而优选为碳数2～15的杂芳基，特别优选为碳数2～10的杂芳基。另外，作为杂芳基，例如可列举除碳以外含有1个至5个选自氧、硫及氮中的杂原子作为环构成原子的杂环等。Examples of the “heteroaryl group” of the “heteroaryl group which may be substituted” include heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, further preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms other than carbon.

作为具体的杂芳基，例如可列举：呋喃基、噻吩基、吡咯基、噁唑基、异噁唑基、噻唑基、异噻唑基、咪唑基、吡唑基、噁二唑基、呋咱基、噻二唑基、三唑基、四唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、苯并呋喃基、异苯并呋喃基、苯并[b]噻吩基、吲哚基、异吲哚基、1H-吲唑基、苯并咪唑基、苯并噁唑基、苯并噻唑基、1H-苯并三唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹噁啉基、酞嗪基、萘啶基、嘌呤基、蝶啶基、咔唑基、吖啶基、吩噁嗪基、吩噻嗪基、吩嗪基、吩噁噻基、噻蒽基、吲嗪基等。Specific examples of the heteroaryl group include furanyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiyl, thianthrenyl, and indolizinyl.

另外，所述芳基及杂芳基可经取代，可分别例如由所述芳基或杂芳基取代。In addition, the aryl group and the heteroaryl group may be substituted, for example, by the aryl group or the heteroaryl group, respectively.

芳基腈衍生物可为多个式(ETM-9)所表示的化合物通过单键等而键结所得的多聚体。在所述情况下，除单键以外，也可利用芳基环(优选为多价的苯环、萘环、蒽环、芴环、苯并芴环、非那烯环、菲环或三亚苯环)进行键结。The aryl nitrile derivative may be a polymer obtained by bonding multiple compounds represented by formula (ETM-9) through single bonds, etc. In the case, in addition to single bonds, an aryl ring (preferably a multivalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenanthren ring, phenanthrene ring or triphenylene ring) may be used for bonding.

作为所述芳基腈衍生物的具体例，例如可列举以下的化合物。Specific examples of the aryl nitrile derivatives include the following compounds.

所述芳基腈衍生物可使用现有的原料与现有的合成方法来制造。The aryl nitrile derivatives can be prepared using existing raw materials and existing synthesis methods.

＜三嗪衍生物＞＜Triazine derivatives＞

三嗪衍生物例如为下述式(ETM-10)所表示的化合物，优选为下述式(ETM-10-1)所表示的化合物。详细情况在美国专利申请公开第2011/0156013号说明书中进行了记载。The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). The details are described in the specification of US Patent Application Publication No. 2011/0156013.

Ar分别独立地为可经取代的芳基或可经取代的杂芳基。n为1～3的整数，优选为2或3。Ar is independently an aryl group which may be substituted or a heteroaryl group which may be substituted. n is an integer of 1 to 3, and is preferably 2 or 3.

作为“可经取代的芳基”的“芳基”，例如可列举碳数6～30的芳基，优选为碳数6～24的芳基，更优选为碳数6～20的芳基，进而优选为碳数6～12的芳基。Examples of the "aryl group" of the "aryl group which may be substituted" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and still more preferably an aryl group having 6 to 12 carbon atoms.

作为具体的“芳基”，可列举：作为单环系芳基的苯基，作为二环系芳基的(2-、3-、4-)联苯基，作为缩合二环系芳基的(1-、2-)萘基，作为三环系芳基的三联苯基(间三联苯-2'-基、间三联苯-4'-基、间三联苯-5'-基、邻三联苯-3'-基、邻三联苯-4'-基、对三联苯-2'-基、间三联苯-2-基、间三联苯-3-基、间三联苯-4-基、邻三联苯-2-基、邻三联苯-3-基、邻三联苯-4-基、对三联苯-2-基、对三联苯-3-基、对三联苯-4-基)，作为缩合三环系芳基的苊-(1-、3-、4-、5-)基、芴-(1-、2-、3-、4-、9-)基、非那烯-(1-、2-)基、(1-、2-、3-、4-、9-)菲基，作为四环系芳基的四联苯基(5'-苯基-间三联苯-2-基、5'-苯基-间三联苯-3-基、5'-苯基-间三联苯-4-基、间四联苯基)，作为缩合四环系芳基的三亚苯-(1-、2-)基、芘-(1-、2-、4-)基、并四苯-(1-、2-、5-)基，作为缩合五环系芳基的苝-(1-、2-、3-)基、并五苯-(1-、2-、5-、6-)基等。Specific examples of the "aryl group" include: phenyl as a monocyclic aromatic group, (2-, 3-, 4-)biphenyl as a bicyclic aromatic group, (1-, 2-)naphthyl as a condensed bicyclic aromatic group, terphenyl groups (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aromatic groups. as a tetracyclic aromatic group such as acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenanthren-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrenyl; as a tetracyclic aromatic group such as quaternaryl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaternaryl); as a condensed tetracyclic aromatic group such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and tetracene-(1-, 2-, 5-)yl; as a condensed pentacyclic aromatic group such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl;

作为“可经取代的杂芳基”的“杂芳基”，例如可列举碳数2～30的杂芳基，优选为碳数2～25的杂芳基，更优选为碳数2～20的杂芳基，进而优选为碳数2～15的杂芳基，特别优选为碳数2～10的杂芳基。另外，作为杂芳基，例如可列举除碳以外含有1个至5个选自氧、硫及氮中的杂原子作为环构成原子的杂环等。Examples of the “heteroaryl group” of the “heteroaryl group which may be substituted” include heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, further preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms other than carbon.

作为具体的杂芳基，例如可列举：呋喃基、噻吩基、吡咯基、噁唑基、异噁唑基、噻唑基、异噻唑基、咪唑基、吡唑基、噁二唑基、呋咱基、噻二唑基、三唑基、四唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、苯并呋喃基、异苯并呋喃基、苯并[b]噻吩基、吲哚基、异吲哚基、1H-吲唑基、苯并咪唑基、苯并噁唑基、苯并噻唑基、1H-苯并三唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹噁啉基、酞嗪基、萘啶基、嘌呤基、蝶啶基、咔唑基、吖啶基、吩噁嗪基、吩噻嗪基、吩嗪基、吩噁噻基、噻蒽基、吲嗪基等。Specific examples of the heteroaryl group include furanyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiyl, thianthrenyl, and indolizinyl.

另外，所述芳基及杂芳基可经取代，可分别例如由所述芳基或杂芳基取代。In addition, the aryl group and the heteroaryl group may be substituted, for example, by the aryl group or the heteroaryl group, respectively.

作为所述三嗪衍生物的具体例，例如可列举以下的化合物。Specific examples of the triazine derivatives include the following compounds.

所述三嗪衍生物可使用现有的原料与现有的合成方法来制造。The triazine derivatives can be produced using existing raw materials and existing synthesis methods.

＜苯并咪唑衍生物＞＜Benzimidazole derivatives＞

苯并咪唑衍生物例如为下述式(ETM-11)所表示的化合物。The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

φ—(苯并咪唑系取代基)n (ETM-11)φ—(Benzimidazole-based substituent)n (ETM-11)

φ为n价的芳基环(优选为n价的苯环、萘环、蒽环、芴环、苯并芴环、非那烯环、菲环或三亚苯环)，n为1～4的整数，“苯并咪唑系取代基”是式(ETM-2)、式(ETM-2-1)及式(ETM-2-2)的“吡啶系取代基”中的吡啶基被取代为苯并咪唑基的取代基，苯并咪唑衍生物中的至少一个氢可由氘取代。φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenanthren ring, phenanthrene ring or triphenylene ring), n is an integer from 1 to 4, and the "benzimidazole-based substituent" is a substituent in which the pyridine group in the "pyridine-based substituent" of formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is substituted by a benzimidazole group, and at least one hydrogen in the benzimidazole derivative can be replaced by deuterium.

*表示键结位置。 *Indicates the bonding position.

所述苯并咪唑基中的R¹¹为氢、碳数1～24的烷基、碳数3～12的环烷基或碳数6～30的芳基，可引用式(ETM-2-1)及式(ETM-2-2)中的R¹¹的说明。R¹¹ in the benzimidazole group is hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and the description of R¹¹ in formula (ETM-2-1) and formula (ETM-2-2) can be cited.

φ进而优选为蒽环或芴环，所述情况下的结构可引用式(ETM-2-1)或式(ETM-2-2)中的说明，各式中的R¹¹～R¹⁸可引用式(ETM-2-1)或式(ETM-2-2)中的说明。另外，在式(ETM-2-1)或式(ETM-2-2)中以键结有两个吡啶系取代基的形态进行了说明，但在将它们取代为苯并咪唑系取代基时，可由苯并咪唑系取代基取代两个吡啶系取代基(即n＝2)，也可由苯并咪唑系取代基取代任意一个吡啶系取代基并由R¹¹～R¹⁸取代另一个吡啶系取代基(即n＝1)。进而，例如可由苯并咪唑系取代基取代式(ETM-2-1)中的R¹¹～R¹⁸的至少一个并由R¹¹～R¹⁸取代“吡啶系取代基”。φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be cited as described in Formula (ETM-2-1) or Formula (ETM-2-2), and R¹¹ to R¹⁸ in each formula can be cited as described in Formula (ETM-2-1) or Formula (ETM-2-2). In addition, Formula (ETM-2-1) or Formula (ETM-2-2) describes the form in which two pyridine substituents are bonded, but when they are substituted with benzimidazole substituents, the two pyridine substituents can be substituted with benzimidazole substituents (i.e., n=2), or any one of the pyridine substituents can be substituted with a benzimidazole substituent and the other pyridine substituent can be substituted with R¹¹ to R¹⁸ (i.e., n=1). Furthermore, for example, at least one of R¹¹ to R¹⁸ in the formula (ETM-2-1) may be substituted with a benzimidazole-based substituent and the "pyridine-based substituent" may be substituted with R¹¹ to R¹⁸ .

作为所述苯并咪唑衍生物的具体例，例如可列举：1-苯基-2-(4-(10-苯基蒽-9-基)苯基)-1H-苯并[d]咪唑、2-(4-(10-(萘-2-基)蒽-9-基)苯基)-1-苯基-1H-苯并[d]咪唑、2-(3-(10-(萘-2-基)蒽-9-基)苯基)-1-苯基-1H-苯并[d]咪唑、5-(10-(萘-2-基)蒽-9-基)-1,2-二苯基-1H-苯并[d]咪唑、1-(4-(10-(萘-2-基)蒽-9-基)苯基)-2-苯基-1H-苯并[d]咪唑、2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑、1-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-2-苯基-1H-苯并[d]咪唑、5-(9,10-二(萘-2-基)蒽-2-基)-1,2-二苯基-1H-苯并[d]咪唑等。Specific examples of the benzimidazole derivatives include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalene-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole, ]imidazole, 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

所述苯并咪唑衍生物可使用现有的原料与现有的合成方法来制造。The benzimidazole derivatives can be prepared using existing raw materials and existing synthesis methods.

＜菲咯啉衍生物＞＜Phenanthroline derivatives＞

菲咯啉衍生物例如为下述式(ETM-12)或式(ETM-12-1)所表示的化合物。详细情况在国际公开第2006/021982号中进行了记载。The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). The details are described in International Publication No. 2006/021982.

φ为n价的芳基环(优选为n价的苯环、萘环、蒽环、芴环、苯并芴环、非那烯环、菲环或三亚苯环)，n为1～4的整数。φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1-4.

各式的R¹¹～R¹⁸分别独立地为氢、烷基(优选为碳数1～24的烷基)、环烷基(优选为碳素3～12的环烷基)或芳基(优选为碳数6～30的芳基)。另外，在式(ETM-12-1)中，R¹¹～R¹⁸的任一者成为与作为芳基环的φ的键结键。R¹¹ to R¹⁸ in each formula are independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). In formula (ETM-12-1), any one of R¹¹ to R¹⁸ is bonded to φ which is an aryl ring.

各菲咯啉衍生物中的至少一个氢可由氘取代。At least one hydrogen in each phenanthroline derivative may be substituted with deuterium.

作为R¹¹～R¹⁸中的烷基、环烷基及芳基，可引用式(ETM-2)中的R¹¹～R¹⁸的说明。另外，关于φ，除所述例子以外，例如也可列举以下结构式。此外，下述结构式中的R分别独立地为氢、甲基、乙基、异丙基、环己基、苯基、1-萘基、2-萘基、联苯基或三联苯基，*表示键结位置。As the alkyl group, cycloalkyl group and aryl group in R¹¹ to R¹⁸ , the description of R¹¹ to R¹⁸ in formula (ETM-2) can be cited. In addition, regarding φ, in addition to the above examples, for example, the following structural formula can also be cited. In addition, R in the following structural formula is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl or terphenyl, and * indicates a bonding position.

作为所述菲咯啉衍生物的具体例，例如可列举：4,7-二苯基-1,10-菲咯啉、2,9-二甲基-4,7-二苯基-1,10-菲咯啉、9,10-二(1,10-菲咯啉-2-基)蒽、2,6-二(1,10-菲咯啉-5-基)吡啶、1,3,5-三(1,10-菲咯啉-5-基)苯、9,9'-二氟-双(1,10-菲咯啉-5-基)、2,9-二甲基-4,7-联苯-1,10-菲咯啉(bathocuproine)、1,3-双(2-苯基-1,10-菲咯啉-9-基)苯或下述结构式所表示的化合物等。Specific examples of the phenanthroline derivatives include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthroline-5-yl), 2,9-dimethyl-4,7-biphenyl-1,10-phenanthroline (bathocuproine), 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, or compounds represented by the following structural formulas.

所述菲咯啉衍生物可使用现有的原料与现有的合成方法来制造。The phenanthroline derivatives can be prepared using existing raw materials and existing synthesis methods.

＜羟基喹啉系金属络合物＞＜Hydroxyquinoline metal complex＞

羟基喹啉系金属络合物例如为下述式(ETM-13)所表示的化合物。The hydroxyquinoline metal complex is, for example, a compound represented by the following formula (ETM-13).

式中，R¹～R⁶分别独立地为氢、氟、烷基、环烷基、芳烷基、烯基、氰基、烷氧基或芳基，M为Li、Al、Ga、Be或Zn，n为1～3的整数。In the formula, R¹ to R⁶ are independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; and n is an integer of 1 to 3.

作为羟基喹啉系金属络合物的具体例，可列举：8-羟基喹啉锂、三(8-羟基喹啉)铝、三(4-甲基-8-羟基喹啉)铝、三(5-甲基-8-羟基喹啉)铝、三(3,4-二甲基-8-羟基喹啉)铝、三(4,5-二甲基-8-羟基喹啉)铝、三(4,6-二甲基-8-羟基喹啉)铝、双(2-甲基-8-羟基喹啉)(苯酚)铝、双(2-甲基-8-羟基喹啉)(2-甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(3-甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(4-甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(2-苯基苯酚)铝、双(2-甲基-8-羟基喹啉)(3-苯基苯酚)铝、双(2-甲基-8-羟基喹啉)(4-苯基苯酚)铝、双(2-甲基-8-羟基喹啉)(2,3-二甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(2,6-二甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(3,4-二甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(3,5-二甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(3,5-二-叔丁基苯酚)铝、双(2-甲基-8-羟基喹啉)(2,6-二苯基苯酚)铝、双(2-甲基-8-羟基喹啉)(2,4,6-三苯基苯酚)铝、双(2-甲基-8-羟基喹啉)(2,4,6-三甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(2,4,5,6-四甲基苯酚)铝、双(2-甲基-8-羟基喹啉)(1-萘酚)铝、双(2-甲基-8-羟基喹啉)(2-萘酚)铝、双(2,4-二甲基-8-羟基喹啉)(2-苯基苯酚)铝、双(2,4-二甲基-8-羟基喹啉)(3-苯基苯酚)铝、双(2,4-二甲基-8-羟基喹啉)(4-苯基苯酚)铝、双(2,4-二甲基-8-羟基喹啉)(3,5-二甲基苯酚)铝、双(2,4-二甲基-8-羟基喹啉)(3,5-二-叔丁基苯酚)铝、双(2-甲基-8-羟基喹啉)铝-μ-氧代-双(2-甲基-8-羟基喹啉)铝、双(2,4-二甲基-8-羟基喹啉)铝-μ-氧代-双(2,4-二甲基-8-羟基喹啉)铝、双(2-甲基-4-乙基-8-羟基喹啉)铝-μ-氧代-双(2-甲基-4-乙基-8-羟基喹啉)铝、双(2-甲基-4-甲氧基-8-羟基喹啉)铝-μ-氧代-双(2-甲基-4-甲氧基-8-羟基喹啉)铝、双(2-甲基-5-氰基-8-羟基喹啉)铝-μ-氧代-双(2-甲基-5-氰基-8-羟基喹啉)铝、双(2-甲基-5-三氟甲基-8-羟基喹啉)铝-μ-氧代-双(2-甲基-5-三氟甲基-8-羟基喹啉)铝、双(10-羟基苯并[h]喹啉)铍等。Specific examples of the hydroxyquinoline metal complex include 8-hydroxyquinoline lithium, tris(8-hydroxyquinoline)aluminum, tris(4-methyl-8-hydroxyquinoline)aluminum, tris(5-methyl-8-hydroxyquinoline)aluminum, tris(3,4-dimethyl-8-hydroxyquinoline)aluminum, tris(4,5-dimethyl-8-hydroxyquinoline)aluminum, tris(4,6-dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-8-hydroxyquinoline)(phenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(4-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(phenylphenol)aluminum, quinoline)(3-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,3-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,4-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-di-tert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-diphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-triphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-trimethylphenol ) aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,5,6-tetramethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(1-naphthol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-naphthol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-dimethylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-di-tert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-8-hydroxyquinoline) Aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2,4-dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-4-ethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-4-methoxy-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-hydroxyquinoline)aluminum, bis(2-methyl-5-cyano-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-hydroxyquinoline)aluminum, bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

所述羟基喹啉系金属络合物可使用现有的原料与现有的合成方法来制造。The hydroxyquinoline metal complex can be produced using existing raw materials and existing synthesis methods.

＜噻唑衍生物及苯并噻唑衍生物＞＜Thiazole derivatives and benzothiazole derivatives＞

噻唑衍生物例如为下述式(ETM-14-1)所表示的化合物。The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

φ—(噻唑系取代基)n (ETM-14-1)φ—(thiazole substituent)n (ETM-14-1)

苯并噻唑衍生物例如为下述式(ETM-14-2)所表示的化合物。The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).

φ-(苯并噻唑系取代基)n (ETM-14-2)φ-(Benzothiazole-based substituent)n (ETM-14-2)

各式的φ为n价的芳基环(优选为n价的苯环、萘环、蒽环、芴环、苯并芴环、非那烯环、菲环或三亚苯环)，n为1～4的整数，“噻唑系取代基”或“苯并噻唑系取代基”是式(ETM-2)、式(ETM-2-1)及式(ETM-2-2)的“吡啶系取代基”中的吡啶基被取代为下述的噻唑基或苯并噻唑基的取代基，噻唑衍生物及苯并噻唑衍生物中的至少一个氢可由氘取代。In each formula, φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenanthren ring, phenanthrene ring or triphenylene ring), n is an integer from 1 to 4, and the "thiazole substituent" or "benzothiazole substituent" is a "pyridine substituent" in formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) wherein the pyridine group is substituted with the following thiazole or benzothiazole substituent, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted by deuterium.

*表示键结位置。 *Indicates the bonding position.

φ进而优选为蒽环或芴环，所述情况下的结构可引用式(ETM-2-1)或式(ETM-2-2)中的说明，各式中的R¹¹～R¹⁸可引用式(ETM-2-1)或式(ETM-2-2)中的说明。另外，在式(ETM-2-1)或式(ETM-2-2)中以键结有两个吡啶系取代基的形态进行了说明，但在将它们取代为噻唑系取代基(或苯并噻唑系取代基)时，可由噻唑系取代基(或苯并噻唑系取代基)取代两个吡啶系取代基(即n＝2)，也可由噻唑系取代基(或苯并噻唑系取代基)取代任意一个吡啶系取代基并由R¹¹～R¹⁸取代另一个吡啶系取代基(即n＝1)。进而，例如可由噻唑系取代基(或苯并噻唑系取代基)取代式(ETM-2-1)中的R¹¹～R¹⁸的至少一个并由R¹¹～R¹⁸取代“吡啶系取代基”。φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be referred to the description in formula (ETM-2-1) or formula (ETM-2-2), and R¹¹ to R¹⁸ in each formula can be referred to the description in formula (ETM-2-1) or formula (ETM-2-2). In addition, in formula (ETM-2-1) or formula (ETM-2-2), it is described in the form of two pyridine substituents bonded, but when these are substituted with thiazole substituents (or benzothiazole substituents), the two pyridine substituents can be substituted with thiazole substituents (or benzothiazole substituents) (i.e., n=2), or any one of the pyridine substituents can be substituted with a thiazole substituent (or benzothiazole substituent) and the other pyridine substituent can be substituted with R¹¹ to R¹⁸ (i.e., n=1). Furthermore, for example, at least one of R¹¹ to R¹⁸ in the formula (ETM-2-1) may be substituted with a thiazole substituent (or a benzothiazole substituent), and the "pyridine substituent" may be substituted with R¹¹ to R¹⁸ .

这些噻唑衍生物或苯并噻唑衍生物可使用现有的原料与现有的合成方法来制造。These thiazole derivatives or benzothiazole derivatives can be produced using existing raw materials and existing synthesis methods.

＜噻咯衍生物＞＜Silole derivatives＞

噻咯衍生物例如为下述式(ETM-15)所表示的化合物。详细情况在日本专利特开平9-194487号公报中进行了记载。The silole derivative is, for example, a compound represented by the following formula (ETM-15). The details are described in Japanese Patent Application Laid-Open No. 9-194487.

X及Y分别独立地为烷基、环烷基、烯基、炔基、烷氧基、烯氧基、炔氧基、芳基、杂芳基，它们可经取代。关于这些基的详细情况，可引用式(D)及式(D-a)等中的说明以及式(ETM-7-2)中的说明。另外，烯氧基及炔氧基分别为烷氧基中的烷基部分被取代为烯基或炔基的基，关于这些烯基及炔基的详细情况，可引用式(ETM-7-2)中的说明。X and Y are independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, and they may be substituted. For the details of these groups, the descriptions in formula (D) and formula (D-a) and the descriptions in formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl part in the alkoxy group is substituted with alkenyl or alkynyl, and for the details of these alkenyl and alkynyl groups, the descriptions in formula (ETM-7-2) can be cited.

另外，X与Y可键结而形成环烷基环(及其一部分变得不饱和的环)，所述环烷基环的详细情况可参照式(D)及式(D-a)等中的环烷基的说明。In addition, X and Y may be bonded to form a cycloalkyl ring (or a partially unsaturated ring thereof), and details of the cycloalkyl ring can be found in the description of the cycloalkyl group in formula (D) and formula (D-a) and the like.

R¹～R⁴分别独立地为氢、卤素、烷基、环烷基、烷氧基、芳氧基、氨基、烷基羰基、芳基羰基、烷氧基羰基、芳氧基羰基、偶氮基、烷基羰氧基、芳基羰氧基、烷氧基羰氧基、芳氧基羰氧基、亚磺酰基(sulfinyl)、磺酰基(sulfonyl)、巯基(sulfanyl)、硅烷基、氨甲酰基、芳基、杂芳基、烯基、炔基、硝基、甲酰基、亚硝基、甲酰氧基、异氰基、氰酸酯基、异氰酸酯基、硫代氰酸酯基、异硫代氰酸酯基或氰基，它们可由烷基、环烷基、芳基或卤素取代，也可在与邻接取代基之间形成稠环。R¹ to R⁴ are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyanate, cyanate, isocyanate, thiocyanate, isothiocyanate or cyano. They may be substituted by alkyl, cycloalkyl, aryl or halogen, and may form a condensed ring with adjacent substituents.

关于R¹～R⁴中的卤素、烷基、环烷基、烷氧基、芳氧基、氨基、芳基、杂芳基、烯基及炔基的详细情况，可引用式(D)及式(D-a)等中的说明。Regarding the details of the halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl groups in R¹ to R⁴ , the descriptions in formula (D) and formula (Da) etc. can be cited.

关于R¹～R⁴中的烷基羰基、芳基羰基、烷氧基羰基、芳氧基羰基、烷基羰氧基、芳基羰氧基、烷氧基羰氧基及芳氧基羰氧基中的烷基、芳基及烷氧基的详细情况，也可引用式(D)及式(D-a)等中的说明。The description of formula (D) and formula (Da) etc. can also be used for details of the alkyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group and aryloxycarbonyloxy group in R¹ to R⁴ .

作为硅烷基，可列举硅烷基、以及硅烷基的三个氢中的至少一个分别独立地由芳基、烷基或环烷基取代的基，优选为三元取代硅烷基，可列举：三芳基硅烷基、三烷基硅烷基、三环烷基硅烷基、二烷基环烷基硅烷基及烷基二环烷基硅烷基等。关于它们中的芳基、烷基及环烷基的详细情况，可引用式(D)及式(D-a)等中的说明。As the silyl group, there can be mentioned a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted by an aryl group, an alkyl group or a cycloalkyl group. Preferably, the silyl group is a triaryl substituted silyl group, and there can be mentioned a triaryl silyl group, a trialkyl silyl group, a tricycloalkyl silyl group, a dialkyl cycloalkyl silyl group and an alkyl dicycloalkyl silyl group. For details of the aryl group, the alkyl group and the cycloalkyl group, the description in formula (D) and formula (D-a) etc. can be cited.

所谓在与邻接取代基之间所形成的稠环，例如为在R¹与R²、R²与R³、R³与R⁴等之间所形成的共轭或非共轭的稠环。这些稠环可在环内结构中包含氮原子、氧原子、硫原子，也可进一步与其他环缩合。The condensed ring formed between adjacent substituents includes, for example, conjugated or non-conjugated condensed rings formed between^R1 and^R2 ,^R2 and^R3 ,^R3 and^R4 , etc. These condensed rings may contain nitrogen atoms, oxygen atoms, sulfur atoms in the endocyclic structure, and may be further condensed with other rings.

其中，优选为当R¹及R⁴为苯基时，X及Y不为烷基或苯基。另外，优选为不同时满足当R¹及R⁴为噻吩基时，X及Y为烷基且R²及R³为烷基、芳基、烯基或R²与R³键结而形成环的环烷基的结构。另外，优选为当R¹及R⁴为硅烷基时，R²、R³、X及Y分别独立地不为氢或碳数1至6的烷基。另外，优选为当为在R¹及R²中缩合有苯环的结构时，X及Y不为烷基及苯基。Among them, it is preferred that when^R1 and^R4 are phenyl groups, X and Y are not alkyl groups or phenyl groups. In addition, it is preferred that the structure that does not simultaneously satisfy the following conditions: when^R1 and^R4 are thienyl groups, X and Y are alkyl groups and^R2 and^R3 are alkyl groups, aryl groups, alkenyl groups, or cycloalkyl groups in which^R2 and^R3 are bonded to form a ring. In addition, it is preferred that when^R1 and^R4 are silyl groups,^R2 ,^R3 , X and Y are not independently hydrogen or an alkyl group having 1 to 6 carbon atoms. In addition, it is preferred that when a benzene ring is condensed in^R1 and^R2 , X and Y are not alkyl groups or phenyl groups.

这些噻咯衍生物可使用现有的原料与现有的合成方法来制造。These silole derivatives can be prepared using existing raw materials and existing synthesis methods.

＜唑啉衍生物＞＜Azoline derivatives＞

唑啉衍生物例如为下述式(ETM-16)所表示的化合物。详细情况在国际公开第2017/014226号中进行了记载。The oxazoline derivative is, for example, a compound represented by the following formula (ETM-16). The details are described in International Publication No. 2017/014226.

式(ETM-16)中，In formula (ETM-16),

φ为源自碳数6～40的芳香族烃的m价基或源自碳数2～40的芳香族杂环的m价基，φ的至少一个氢可由碳数1～6的烷基、碳数3～14的环烷基、碳数6～18的芳基或碳数2～18的杂芳基取代，φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms,

Y分别独立地为-O-、-S-或＞N-Ar，Ar为碳数6～12的芳基或碳数2～12的杂芳基，Ar的至少一个氢可由碳数1～4的烷基、碳数5～10的环烷基、碳数6～12的芳基或碳数2～12的杂芳基取代，R¹～R⁵分别独立地为氢、碳数1～4的烷基或碳数5～10的环烷基，其中，所述＞N-Ar中的Ar及所述R¹～R⁵中的任意一个为与L键结的部位，Y is independently -O-, -S- or >N-Ar, Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, at least one hydrogen atom of Ar may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, R¹ to R⁵ are independently hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein any one of Ar and R¹ to R⁵ in >N-Ar is a site bonded to L,

L分别独立地选自由下述式(L-1)所表示的二价基及下述式(L-2)所表示的二价基所组成的群组中，L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2),

式(L-1)中，X¹～X⁶分别独立地为＝CR⁶-或＝N-，X¹～X⁶中的至少两个为＝CR⁶-，X¹～X⁶中的两个＝CR⁶-中的R⁶为与φ或唑啉环键结的部位，其以外的＝CR⁶-中的R⁶为氢，In formula (L-1), X¹ to X⁶ are each independently ═CR⁶ - or ═N-, at least two of X¹ to X⁶ are ═CR⁶ -, R⁶ in two of X¹ to X⁶ =CR⁶ - is a site bonded to the φ or oxazoline ring, and R⁶ in other =CR⁶ - is hydrogen,

式(L-2)中，X⁷～X¹⁴分别独立地为＝CR⁶-或＝N-，X⁷～X¹⁴中的至少两个为＝CR⁶-，X⁷～X¹⁴中的两个＝CR⁶-中的R⁶为与φ或唑啉环键结的部位，其以外的＝CR⁶-中的R⁶为氢，In formula (L-2),^X7 to^X14 are each independently =^CR6- or =N-, at least two of^X7 to^X14 are =^CR6- ,^R6 in two =^CR6- of^X7 to^X14 are sites bonded to φ or the oxazoline ring, and^R6 in other =^CR6- is hydrogen,

L的至少一个氢可由碳数1～4的烷基、碳数5～10的环烷基、碳数6～10的芳基或碳数2～10的杂芳基取代，At least one hydrogen of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

m为1～4的整数，当m为2～4时，由唑啉环与L形成的基可相同也可不同，而且，m is an integer of 1 to 4. When m is 2 to 4, the groups formed by the oxazoline ring and L may be the same or different, and,

式(ETM-16)所表示的化合物中的至少一个氢可由氘取代。At least one hydrogen in the compound represented by Formula (ETM-16) may be substituted by deuterium.

具体的唑啉衍生物为下述式(ETM-16-1)或式(ETM-16-2)所表示的化合物。A specific oxazoline derivative is a compound represented by the following formula (ETM-16-1) or formula (ETM-16-2).

式(ETM-16-1)及式(ETM-16-2)中，In formula (ETM-16-1) and formula (ETM-16-2),

φ为源自碳数6～40的芳香族烃的m价基或源自碳数2～40的芳香族杂环的m价基，φ的至少一个氢可由碳数1～6的烷基、碳数3～14的环烷基、碳数6～18的芳基或碳数2～18的杂芳基取代，φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms,

式(ETM-16-1)中，Y分别独立地为-O-、-S-或＞N-Ar，Ar为碳数6～12的芳基或碳数2～12的杂芳基，Ar的至少一个氢可由碳数1～4的烷基、碳数5～10的环烷基、碳数6～12的芳基或碳数2～12的杂芳基取代，In formula (ETM-16-1), Y is independently -O-, -S- or >N-Ar, Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, and at least one hydrogen atom of Ar may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 2 to 12 carbon atoms,

式(ETM-16-1)中，R¹～R⁴分别独立地为氢、碳数1～4的烷基或碳数5～10的环烷基，其中，R¹与R²相同，且R³与R⁴相同，In formula (ETM-16-1), R¹ to R⁴ are independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R¹ and R² are the same, and R³ and R⁴ are the same,

式(ETM-16-2)中，R¹～R⁵分别独立地为氢、碳数1～4的烷基或碳数5～10的环烷基，其中，R¹与R²相同，且R³与R⁴相同，In formula (ETM-16-2), R¹ to R⁵ are independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein R¹ and R² are the same, and R³ and R⁴ are the same,

式(ETM-16-1)及式(ETM-16-2)中，In formula (ETM-16-1) and formula (ETM-16-2),

L分别独立地选自由下述式(L-1)所表示的二价基及下述式(L-2)所表示的二价基所组成的群组中，L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2),

式(L-1)中，X¹～X⁶分别独立地为＝CR⁶-或＝N-，X¹～X⁶中的至少两个为＝CR⁶-，X¹～X⁶中的两个＝CR⁶-中的R⁶为与φ或唑啉环键结的部位，其以外的＝CR⁶-中的R⁶为氢，In formula (L-1), X¹ to X⁶ are each independently ═CR⁶ - or ═N-, at least two of X¹ to X⁶ are ═CR⁶ -, R⁶ in two of X¹ to X⁶ =CR⁶ - is a site bonded to the φ or oxazoline ring, and R⁶ in other =CR⁶ - is hydrogen,

式(L-2)中，X⁷～X¹⁴分别独立地为＝CR⁶-或＝N-，X⁷～X¹⁴中的至少两个为＝CR⁶-，X⁷～X¹⁴中的两个＝CR⁶-中的R⁶为与φ或唑啉环键结的部位，其以外的＝CR⁶-中的R⁶为氢，In formula (L-2),^X7 to^X14 are each independently =^CR6- or =N-, at least two of^X7 to^X14 are =^CR6- ,^R6 in two =^CR6- of^X7 to^X14 are sites bonded to φ or the oxazoline ring, and^R6 in other =^CR6- is hydrogen,

L的至少一个氢可由碳数1～4的烷基、碳数5～10的环烷基、碳数6～10的芳基或碳数2～10的杂芳基取代，At least one hydrogen of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

m为1～4的整数，当m为2～4时，由唑啉环与L形成的基可相同也可不同，而且，m is an integer of 1 to 4. When m is 2 to 4, the groups formed by the oxazoline ring and L may be the same or different, and,

式(ETM-16-1)或式(ETM-16-2)所表示的化合物中的至少一个氢可由氘取代。At least one hydrogen in the compound represented by Formula (ETM-16-1) or Formula (ETM-16-2) may be substituted with deuterium.

优选为：φ选自由下述式(φ1-1)～式(φ1-18)所表示的一价基、下述式(φ2-1)～式(φ2-34)所表示的二价基、下述式(φ3-1)～式(φ3-3)所表示的三价基及下述式(φ4-1)～式(φ4-2)所表示的四价基所组成的群组中，φ的至少一个氢可由碳数1～6的烷基、碳数3～14的环烷基、碳数6～18的芳基或碳数2～18的杂芳基取代。Preferably, φ is selected from the group consisting of a monovalent group represented by the following formula (φ1-1) to (φ1-18), a divalent group represented by the following formula (φ2-1) to (φ2-34), a trivalent group represented by the following formula (φ3-1) to (φ3-3) and a tetravalent group represented by the following formula (φ4-1) to (φ4-2), and at least one hydrogen of φ can be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms or a heteroaryl group having 2 to 18 carbon atoms.

式中的Z为＞CR₂、＞N-Ar、＞N-L、-O-或-S-，＞CR₂中的R分别独立地为碳数1～4的烷基、碳数5～10的环烷基、碳数6～12的芳基或碳数2～12的杂芳基，R可相互键结而形成环，＞N-Ar中的Ar为碳数6～12的芳基或碳数2～12的杂芳基，＞N-L中的L为式(ETM-16)、式(ETM-16-1)或式(ETM-16-2)中的L。式中的*表示键结位置。In the formula, Z is >CR₂ , >N-Ar, >NL, -O- or -S-, R in >CR₂ is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, and R may be bonded to each other to form a ring, Ar in >N-Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, and L in >NL is L in formula (ETM-16), formula (ETM-16-1) or formula (ETM-16-2). In the formula, * indicates a bonding position.

优选为：L为选自由苯、萘、吡啶、吡嗪、嘧啶、哒嗪、三嗪、喹啉、异喹啉、萘啶、酞嗪、喹噁啉、喹唑啉、噌啉及喋啶所组成的群组中的环的二价基，L的至少一个氢可由碳数1～4的烷基、碳数5～10的环烷基、碳数6～10的芳基或碳数2～10的杂芳基取代。Preferably, L is a divalent ring radical selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline and pteridine, and at least one hydrogen of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 2 to 10 carbon atoms.

优选为：作为Y或Z的＞N-Ar中的Ar选自由苯基、萘基、吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基、喹啉基、异喹啉基、萘啶基、酞嗪基、喹噁啉基、喹唑啉基、噌啉基及喋啶基所组成的群组中，作为Y的＞N-Ar中的Ar的至少一个氢可由碳数1～4的烷基、碳数5～10的环烷基或碳数6～10的芳基取代。Preferably, Ar in the >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and pteridinyl, and at least one hydrogen of Ar in the >N-Ar as Y may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.

优选为：R¹～R⁴分别独立地为氢、碳数1～4的烷基或碳数5～10的环烷基，其中，R¹与R²相同，R³与R⁴相同，且R¹～R⁴的全部不会同时为氢，而且，m为1或2，当m为2时，由唑啉环与L形成的基相同。Preferably, R¹ to R⁴ are independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, wherein R¹ and R² are the same, R³ and R⁴ are the same, and all of R¹ to R⁴ are not hydrogen atoms at the same time, and m is 1 or 2. When m is 2, the group formed by the oxazoline ring and L is the same.

作为唑啉衍生物的具体例，例如可列举以下的化合物。此外，结构式中的“Me”表示甲基。Specific examples of the oxazoline derivatives include the following compounds: In addition, "Me" in the structural formula represents a methyl group.

更优选为：φ选自由下述式(φ2-1)、式(φ2-31)、式(φ2-32)、式(φ2-33)及式(φ2-34)所表示的二价基所组成的群组中，φ的至少一个氢可由碳数6～18的芳基取代，More preferably, φ is selected from the group consisting of divalent groups represented by the following formula (φ2-1), formula (φ2-31), formula (φ2-32), formula (φ2-33) and formula (φ2-34), at least one hydrogen of φ may be substituted by an aromatic group having 6 to 18 carbon atoms,

(*表示键结位置)(* indicates the bond position)

L为选自由苯、吡啶、吡嗪、嘧啶、哒嗪及三嗪所组成的群组中的环的二价基，L的至少一个氢可由碳数1～4的烷基、碳数5～10的环烷基、碳数6～10的芳基或碳数2～14的杂芳基取代，L is a divalent cyclic radical selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine and triazine, at least one hydrogen of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 2 to 14 carbon atoms,

作为Y的＞N-Ar中的Ar选自由苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基及三嗪基所组成的群组中，所述Ar的至少一个氢可由碳数1～4的烷基、碳数5～10的环烷基或碳数6～10的芳基取代，Ar in the >N-Ar as Y is selected from the group consisting of phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl, and at least one hydrogen of Ar may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms,

R¹～R⁴分别独立地为氢、碳数1～4的烷基或碳数5～10的环烷基，其中，R¹与R²相同，R³与R⁴相同，且R¹～R⁴的全部不会同时为氢，而且，R¹ to R⁴ are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, wherein R¹ and R² are the same, R³ and R⁴ are the same, and all of R¹ to R⁴ are not hydrogen atoms at the same time, and,

m为2，由唑啉环与L形成的基相同。m is 2, and the group formed by the oxazoline ring and L is the same.

作为唑啉衍生物的其他具体例，例如可列举以下的化合物。此外，结构式中的“Me”表示甲基。Other specific examples of oxazoline derivatives include the following compounds: In addition, "Me" in the structural formula represents a methyl group.

关于规定所述唑啉衍生物的所述各式中的烷基、环烷基、芳基或杂芳基的详细情况，可引用式(D)及式(D-a)等中的说明。Regarding the details of the alkyl group, cycloalkyl group, aryl group or heteroaryl group in each of the above formulae defining the above oxazoline derivatives, the descriptions in formula (D) and formula (D-a) and the like can be cited.

所述唑啉衍生物可使用现有的原料与现有的合成方法来制造。The oxazoline derivatives can be prepared using existing raw materials and existing synthesis methods.

＜还原性物质＞＜Reducing substances＞

也可在电子传输层或电子注入层中还包含能够将形成电子传输层或电子注入层的材料还原的物质。所述还原性物质只要是具有一定的还原性的物质，则可使用各种物质，例如可优选地使用选自由碱金属、碱土金属、稀土金属、碱金属的氧化物、碱金属的卤化物、碱土金属的氧化物、碱土金属的卤化物、稀土金属的氧化物、稀土金属的卤化物、碱金属的有机络合物、碱土金属的有机络合物及稀土金属的有机络合物所组成的群组中的至少一种。The electron transport layer or the electron injection layer may also contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. The reducing substance may be a variety of substances as long as it has a certain reducing property, for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be preferably used.

作为优选的还原性物质，可列举Na(功函数2.36eV)、K(功函数2.28eV)、Rb(功函数2.16eV)或Cs(功函数1.95eV)等碱金属，或者Ca(功函数2.9eV)、Sr(功函数2.0eV～2.5eV)或Ba(功函数2.52eV)等碱土金属，特别优选为功函数为2.9eV以下的物质。这些中，更优选的还原性物质为K、Rb或Cs的碱金属，进而优选为Rb或Cs，最优选为Cs。这些碱金属的还原能力特别高，通过向形成电子传输层或电子注入层的材料中添加比较少量的所述碱金属，可实现有机EL元件中的发光亮度的提高或长寿命化。另外，作为功函数为2.9eV以下的还原性物质，两种以上的这些碱金属的组合也优选，特别优选为包含Cs的组合，例如Cs与Na、Cs与K、Cs与Rb或Cs与Na及K的组合。通过包含Cs，可有效率地发挥还原能力，通过添加至形成电子传输层或电子注入层的材料中，可实现有机EL元件中的发光亮度的提高或长寿命化。As preferred reducing substances, alkali metals such as Na (work function 2.36eV), K (work function 2.28eV), Rb (work function 2.16eV) or Cs (work function 1.95eV) or alkaline earth metals such as Ca (work function 2.9eV), Sr (work function 2.0eV~2.5eV) or Ba (work function 2.52eV) can be listed, and substances with a work function of 2.9eV or less are particularly preferred. Among these, the more preferred reducing substances are alkali metals of K, Rb or Cs, and more preferably Rb or Cs, and most preferably Cs. The reducing ability of these alkali metals is particularly high. By adding a relatively small amount of the alkali metal to the material forming the electron transport layer or the electron injection layer, the luminous brightness in the organic EL element can be improved or the life can be prolonged. In addition, as the reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and a combination containing Cs is particularly preferred, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or the electron injection layer, the luminance of the light emission in the organic EL element can be improved or the life can be prolonged.

9.有机电场发光元件中的阴极9. Cathode in organic electroluminescent element

阴极108发挥经由电子注入层107及电子传输层106而将电子注入发光层105的作用。The cathode 108 plays a role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

作为形成阴极108的材料，若为可将电子高效地注入有机层的物质，则并无特别限定，可使用与形成阳极102的材料相同的材料。其中，优选为锡、铟、钙、铝、银、铜、镍、铬、金、铂、铁、锌、锂、钠、钾、铯及镁等金属或它们的合金(镁-银合金、镁-铟合金、氟化锂/铝等铝-锂合金等)等。为了提高电子注入效率来提高元件特性，有效的是锂、钠、钾、铯、钙、镁或包含这些低功函数金属的合金。然而，通常而言，这些低功函数金属多数情况下在大气中不稳定。为了改善所述方面，已知有例如向有机层中掺杂微量的锂、铯或镁，并使用稳定性高的电极的方法。作为其他掺杂剂，也可使用氟化锂、氟化铯、氧化锂及氧化铯之类的无机盐。但是，并不限定于这些。As the material forming the cathode 108, if it is a substance that can efficiently inject electrons into the organic layer, it is not particularly limited, and the same material as the material forming the anode 102 can be used. Among them, preferably metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride/aluminum, etc.) and the like. In order to improve the efficiency of electron injection to improve the characteristics of the element, lithium, sodium, potassium, cesium, calcium, magnesium or alloys containing these low work function metals are effective. However, generally speaking, these low work function metals are unstable in the atmosphere in most cases. In order to improve the above aspects, it is known that there is a method of doping a trace amount of lithium, cesium or magnesium into the organic layer and using an electrode with high stability. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

进而，可列举如下作为优选例：为了保护电极而将铂、金、银、铜、铁、锡、铝及铟等金属或使用这些金属的合金，及二氧化硅、二氧化钛及氮化硅等无机物，聚乙烯醇，氯乙烯，烃系高分子化合物等进行层叠。这些电极的制作方法只要为电阻加热、电子束蒸镀、溅镀、离子镀及涂布等可取得导通的方法，则也无特别限制。Furthermore, the following are preferred examples: for protecting the electrodes, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium or alloys thereof, inorganic substances such as silicon dioxide, titanium dioxide and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. are laminated. The method for producing these electrodes is not particularly limited as long as it is a method that can achieve conduction such as resistance heating, electron beam evaporation, sputtering, ion plating and coating.

10.各层中可使用的粘结剂10. Adhesives that can be used in each layer

以上的空穴注入层、空穴传输层、发光层、电子传输层及电子注入层中所使用的材料可单独地形成各层，也可分散于作为高分子粘结剂的聚氯乙烯、聚碳酸酯、聚苯乙烯、聚(N-乙烯咔唑)、聚甲基丙烯酸甲酯、聚甲基丙烯酸丁酯、聚酯、聚砜、聚苯醚、聚丁二烯、烃树脂、酮树脂、苯氧基树脂、聚酰胺、乙基纤维素、乙酸乙烯酯树脂、丙烯腈-丁二烯-苯乙烯(Acrylonitrile Butadiene Styrene，ABS)树脂、聚氨基甲酸酯树脂等溶剂可溶性树脂，或者酚树脂、二甲苯树脂、石油树脂、脲树脂、三聚氰胺树脂、不饱和聚酯树脂、醇酸树脂、环氧树脂、硅酮树脂等硬化性树脂等中来使用。The materials used in the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer and electron injection layer can form each layer separately, or can be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene ether, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, acrylonitrile-butadiene-styrene (ABS) resin, polyurethane resin, etc., or in hardening resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. as a polymer binder.

＜＜有机电场发光元件的制作方法＞＞＜＜Method for producing organic electroluminescent element＞＞

构成有机EL元件的各层可通过利用蒸镀法、电阻加热蒸镀、电子束蒸镀、溅镀、分子层叠法、印刷法、喷墨法、旋涂法或浇铸法、涂布法等方法将应构成各层的材料制成薄膜来形成。以所述方式形成的各层的膜厚并无特别限定，可根据材料的性质来适宜设定，但通常为2nm～5000nm的范围。膜厚通常可利用石英振荡式膜厚测定装置等来测定。在使用蒸镀法进行薄膜化的情况下，其蒸镀条件根据材料的种类、膜的目标结晶结构及缔合结构等而不同。蒸镀条件通常优选为在舟皿加热温度+50℃～+400℃、真空度10^-6Pa～10^-3Pa、蒸镀速度0.01nm/sec～50nm/sec、基板温度-150℃～+300℃、膜厚2nm～5μm的范围内适宜设定。Each layer constituting the organic EL element can be formed by making the material constituting each layer into a thin film by using a vapor deposition method, a resistance heating vapor deposition method, an electron beam vapor deposition method, a sputtering method, a molecular stacking method, a printing method, an inkjet method, a spin coating method, a casting method, a coating method, etc. The film thickness of each layer formed in the above manner is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2nm to 5000nm. The film thickness can usually be measured using a quartz oscillation film thickness measuring device, etc. When the vapor deposition method is used for thin film formation, the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, etc. The vapor deposition conditions are usually preferably appropriately set within the range of a boat heating temperature of +50°C to +400°C, a vacuum degree of 10^-6 Pa to 10^-3 Pa, a vapor deposition rate of 0.01nm/sec to 50nm/sec, a substrate temperature of -150°C to +300°C, and a film thickness of 2nm to 5μm.

接着，作为制作有机EL元件的方法的一例，对包括阳极/空穴注入层/空穴传输层/包含主体材料与掺杂剂材料的发光层/电子传输层/电子注入层/阴极的有机EL元件的制作方法进行说明。在适当的基板上，利用蒸镀法等形成阳极材料的薄膜来制作阳极，然后在所述阳极上形成空穴注入层及空穴传输层的薄膜。在所述薄膜上对主体材料与掺杂剂材料进行共蒸镀而形成薄膜来作为发光层，在所述发光层上形成电子传输层、电子注入层，进而利用蒸镀法等形成包含阴极用物质的薄膜来作为阴极，由此获得目标有机EL元件。此外，在所述有机EL元件的制作中，也可使制作顺序相反，而以阴极、电子注入层、电子传输层、发光层、空穴传输层、空穴注入层、阳极的顺序制作。Next, as an example of a method for making an organic EL element, a method for making an organic EL element including an anode/hole injection layer/hole transport layer/light-emitting layer containing a main material and a dopant material/electron transport layer/electron injection layer/cathode is described. On an appropriate substrate, a thin film of an anode material is formed by a vapor deposition method, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. The main material and the dopant material are co-evaporated on the thin film to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and then a thin film containing a cathode material is formed by a vapor deposition method as a cathode, thereby obtaining a target organic EL element. In addition, in the production of the organic EL element, the production order can also be reversed, and the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, anode are produced in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, anode.

在对以所述方式获得的有机EL元件施加直流电压的情况下，只要将阳极作为+的极性，将阴极作为-的极性来施加即可，若施加2V～40V左右的电压，则可自透明或半透明的电极侧(阳极或阴极、及两者)观测到发光。另外，所述有机EL元件在施加有脉冲电流或交流电流的情况下也发光。此外，所施加的交流的波形可为任意。When a direct current voltage is applied to the organic EL element obtained in the above manner, it can be applied with the anode as + polarity and the cathode as - polarity. If a voltage of about 2V to 40V is applied, light emission can be observed from the transparent or translucent electrode side (anode or cathode, or both). In addition, the organic EL element also emits light when a pulse current or an alternating current is applied. In addition, the waveform of the applied alternating current can be arbitrary.

＜＜有机电场发光元件的应用例＞＞＜＜Application examples of organic electroluminescent elements＞＞

另外，本发明也可应用于包括有机EL元件的显示装置或包括有机EL元件的照明装置等。Furthermore, the present invention can also be applied to a display device including an organic EL element, a lighting device including an organic EL element, or the like.

包括有机EL元件的显示装置或照明装置可通过将本实施方式的有机EL元件与现有的驱动装置加以连接等现有的方法来制造，且可适宜使用直流驱动、脉冲驱动、交流驱动等现有的驱动方法来进行驱动。A display device or lighting device including an organic EL element can be manufactured by an existing method such as connecting the organic EL element of this embodiment to an existing driving device, and can be appropriately driven using an existing driving method such as DC driving, pulse driving, and AC driving.

作为显示装置，例如可列举：彩色平板显示器等面板显示器、挠性彩色有机电场发光(EL)显示器等挠性显示器等(例如参照日本专利特开平10-335066号公报、日本专利特开2003-321546号公报、日本专利特开2004-281086号公报等)。另外，作为显示器的显示方式，例如可列举矩阵和/或分段方式等。此外，矩阵显示与分段显示可在同一面板(panel)中共存。As display devices, for example, panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays, etc. (for example, refer to Japanese Patent Laid-Open No. 10-335066, Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Laid-Open No. 2004-281086, etc.). In addition, as display modes of displays, for example, matrix and/or segment modes can be listed. In addition, matrix display and segment display can coexist in the same panel.

在矩阵中，将用于显示的像素二维地配置成格子状或马赛克状等，从而由像素的集合来显示文字或图像。像素的形状或尺寸是根据用途来决定。例如在个人计算机、监视器、电视机的图像及文字显示中，通常使用一边为300μm以下的四边形的像素，另外，在显示面板之类的大型显示器的情况下，使用一边为mm级的像素。在单色显示的情况下，只要排列相同颜色的像素即可，在彩色显示的情况下，使红、绿、蓝的像素并列来进行显示。在所述情况下，典型的有三角型与条纹型。而且，作为所述矩阵的驱动方法，可为线序(line-sequential)驱动方法或有源矩阵的任一者。线序驱动有结构简单这一优点，但在考虑了运行特性的情况下，有时有源矩阵更优异，因此驱动方法也需要根据用途而区分使用。In a matrix, pixels for display are arranged two-dimensionally in a grid or mosaic shape, etc., so that text or images are displayed by a collection of pixels. The shape or size of a pixel is determined according to the purpose. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with a side of less than 300μm are usually used. In addition, in the case of large displays such as display panels, pixels with a side of mm are used. In the case of monochrome display, it is sufficient to arrange pixels of the same color. In the case of color display, red, green, and blue pixels are displayed in parallel. In the case, typical ones are triangular and stripe types. Moreover, as a driving method of the matrix, it can be either a line-sequential driving method or an active matrix. Line-sequential driving has the advantage of a simple structure, but in the case of considering the operating characteristics, an active matrix is sometimes more excellent, so the driving method also needs to be used according to the purpose.

在分段方式(类型)中，以显示事先所决定的信息的方式形成图案，并使所决定的区域发光。例如可列举：数字时钟或温度计中的时刻或温度显示、声频设备或电磁炉等的运行状态显示及汽车的面板显示等。In the segmented method (type), a pattern is formed in a manner to display predetermined information, and the determined area is illuminated. Examples include: time or temperature display in a digital clock or thermometer, operating status display of audio equipment or induction cookers, and panel display of a car.

作为照明装置，例如可列举室内照明等照明装置、液晶显示装置的背光源等(例如参照日本专利特开2003-257621号公报、日本专利特开2003-277741号公报、日本专利特开2004-119211号公报等)。背光源主要为了提高不进行自发光的显示装置的视认性而使用，其用于液晶显示装置、时钟、声频装置、汽车面板、显示板及标识等。特别是，作为液晶显示装置中的薄型化正成为问题的个人计算机用途的背光源，当考虑到现有方式因包含荧光灯或导光板而难以薄型化时，使用了本实施方式的发光元件的背光源具有薄型、轻量的特征。As lighting devices, for example, lighting devices such as indoor lighting, backlight sources of liquid crystal display devices, etc. can be listed (for example, refer to Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, Japanese Patent Publication No. 2004-119211, etc.). Backlight sources are mainly used to improve the visibility of display devices that do not emit light by themselves, and are used for liquid crystal display devices, clocks, audio devices, automobile panels, display boards, and logos. In particular, as a backlight source for personal computers where thinning of liquid crystal display devices is becoming a problem, when considering that the existing methods are difficult to be thinned due to the inclusion of fluorescent lamps or light guide plates, the backlight source using the light-emitting element of this embodiment has the characteristics of being thin and lightweight.

[实施例][Example]

以下，通过实施例来更具体地说明本发明，但本发明并不限定于这些。首先，以下对多环芳香族化合物的合成例进行说明。The present invention will be described in more detail below by way of examples, but the present invention is not limited thereto. First, a synthesis example of a polycyclic aromatic compound will be described below.

合成例(AO)：中间物(I-C)的合成Synthesis Example (AO): Synthesis of Intermediate (I-C)

在氮气环境下，将1,2-二溴苯(10.0g)及4-甲氧基-1-萘酚(6.2g)溶解于二甲基甲酰胺(200ml)中，向所得物中加入碳酸铯(46.3g)、四(三苯基膦)钯(0)(2.3g)，在150℃下进行15小时搅拌。在反应后，向反应溶液中加入水与乙酸乙酯，将有机层分离并加以水洗。然后，将有机层浓缩而获得粗产物。利用硅胶管柱(洗脱液：甲苯)对粗产物进行纯化，由此获得中间物(I-A)(2.9g)。Under nitrogen atmosphere, 1,2-dibromobenzene (10.0 g) and 4-methoxy-1-naphthol (6.2 g) were dissolved in dimethylformamide (200 ml), cesium carbonate (46.3 g) and tetrakis(triphenylphosphine)palladium(0) (2.3 g) were added to the resultant, and the mixture was stirred at 150° C. for 15 hours. After the reaction, water and ethyl acetate were added to the reaction solution, and the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate (I-A) (2.9 g).

在氮气环境下，将中间物(I-A)(2.9g)溶解于二氯甲烷(100ml)中，冷却至-70℃。向所得物中滴加三溴化硼的二氯甲烷溶液(1M、15.6ml)。升温至室温，搅拌2小时，然后对反应溶液进行冰浴冷却并滴加水(80ml)。利用二氯甲烷对水层进行提取，将有机层合并加以浓缩而获得粗产物。利用二氯甲烷对所获得的粗产物进行清洗，由此获得中间物(I-B)(2.3g)。Under nitrogen atmosphere, the intermediate (I-A) (2.9 g) was dissolved in dichloromethane (100 ml) and cooled to -70°C. A dichloromethane solution of boron tribromide (1 M, 15.6 ml) was added dropwise to the obtained product. The mixture was heated to room temperature and stirred for 2 hours, then the reaction solution was cooled in an ice bath and water (80 ml) was added dropwise. The aqueous layer was extracted with dichloromethane, and the organic layers were combined and concentrated to obtain a crude product. The obtained crude product was washed with dichloromethane to obtain an intermediate (I-B) (2.3 g).

在氮气环境下，向中间物(I-B)(2.3g)中加入吡啶(60ml)，冷却至0℃并滴加三氟甲磺酸酐(Tf₂O、3.6g)。升温至室温，搅拌2小时，然后向反应溶液中加入索米克斯(Solmix)而获得结晶。利用索米克斯(Solmix)对所获得的结晶进行清洗，由此获得中间物(I-C)(1.8g)。Under nitrogen atmosphere, pyridine (60 ml) was added to the intermediate (IB) (2.3 g), cooled to 0°C, and trifluoromethanesulfonic anhydride (Tf₂ O, 3.6 g) was added dropwise. The temperature was raised to room temperature and stirred for 2 hours, and then Solmix was added to the reaction solution to obtain crystals. The obtained crystals were washed with Solmix to obtain the intermediate (IC) (1.8 g).

合成例(A1)：化合物(H-1)的合成Synthesis Example (A1): Synthesis of Compound (H-1)

在氮气环境下，将中间物(I-C)(1.8g)溶解于甲苯(100ml)中，加入4,4,5,5-四甲基-2-(10-苯基蒽-9-基)-1,3,2-二氧杂硼烷(2.2g)、碳酸钾(1.4g)、四丁基溴化铵(TBAB(Tetrabutylammonium bromide)、0.4g)及双(二叔丁基(4-二甲基氨基苯基)膦)二氯钯(Pd-132、0.35g)，在加热回流下搅拌5小时。在反应后，向反应液中加入水与乙酸乙酯而获得粗产物。利用硅胶短管柱(洗脱液：氯苯)对所获得的粗产物进行纯化，由此获得化合物(H-1)(0.5g)。Under nitrogen atmosphere, the intermediate (I-C) (1.8 g) was dissolved in toluene (100 ml), and 4,4,5,5-tetramethyl-2-(10-phenylanthracen-9-yl)-1,3,2-dioxaborolane (2.2 g), potassium carbonate (1.4 g), tetrabutylammonium bromide (TBAB (Tetrabutylammonium bromide), 0.4 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (Pd-132, 0.35 g) were added, and the mixture was stirred under heating reflux for 5 hours. After the reaction, water and ethyl acetate were added to the reaction solution to obtain a crude product. The obtained crude product was purified using a silica gel short column (eluent: chlorobenzene) to obtain compound (H-1) (0.5 g).

电子电离质谱(Electron Ionization Mass Spectrometry，EI-MS)：m/z＝470.Electron Ionization Mass Spectrometry (EI-MS): m/z = 470.

¹H-核磁共振(Nuclear Magnetic Resonance，NMR)(CDCl₃)：δ＝7.89(d,2H),7.73(d,2H),7.63(m,3H),7.57(m,3H),7.51(m,1H),7.45(d,1H),7.33(m,3H),7.25(m,2H),7.18(m,4H),6.85(d,1H).¹ H-Nuclear Magnetic Resonance (NMR) (CDCl₃ ): δ=7.89(d,2H),7.73(d,2H),7.63(m,3H),7.57(m,3H),7.51(m ,1H),7.45(d,1H),7.33(m,3H),7.25(m,2H),7.18(m,4H),6.85(d,1H).

合成例(A2)：化合物(H-3)的合成Synthesis Example (A2): Synthesis of Compound (H-3)

使用与合成例(A1)相同的方法来合成化合物(H-3)。EI-MS：m/z＝520.Compound (H-3) was synthesized using the same method as in Synthesis Example (A1). EI-MS: m/z = 520.

合成例(A3)：化合物(H-6)的合成Synthesis Example (A3): Synthesis of Compound (H-6)

使用与合成例(A1)相同的方法来合成化合物(H-6)。EI-MS：m/z＝546.Compound (H-6) was synthesized using the same method as in Synthesis Example (A1). EI-MS: m/z = 546.

合成例(A4)：化合物(H-26)的合成Synthesis Example (A4): Synthesis of Compound (H-26)

使用与合成例(A1)相同的方法来合成化合物(H-26)。Compound (H-26) was synthesized by the same method as in Synthesis Example (A1).

EI-MS：m/z＝596.EI-MS: m/z = 596.

¹H-NMR(CDCl₃)：δ＝8.53(d,1H),8.12(d,1H),8.02(d,1H),7.95(m,2H),7.75(m,6H),7.60(m,5H),7.52(m,2H),7.33(m,4H).¹ H-NMR (CDCl₃ ): δ = 8.53 (d, 1H), 8.12 (d, 1H), 8.02 (d, 1H), 7.95 (m, 2H), 7.75 (m, 6H), 7.60 (m, 5H),7.52(m,2H),7.33(m,4H).

合成例(A5)：化合物(H-35)的合成Synthesis Example (A5): Synthesis of Compound (H-35)

使用与合成例(A1)相同的方法来合成化合物(H-35)。Compound (H-35) was synthesized by the same method as in Synthesis Example (A1).

EI-MS：m/z＝470.EI-MS: m/z = 470.

合成例(A6)：化合物(H-280)的合成Synthesis Example (A6): Synthesis of Compound (H-280)

使用与合成例(A1)相同的方法来合成化合物(H-280)。EI-MS：m/z＝545.Compound (H-280) was synthesized using the same method as in Synthesis Example (A1). EI-MS: m/z = 545.

合成例(A7)：化合物(H-420)的合成Synthesis Example (A7): Synthesis of Compound (H-420)

使用与合成例(A1)相同的方法来合成化合物(H-420)。EI-MS：m/z＝496.Compound (H-420) was synthesized using the same method as in Synthesis Example (A1). EI-MS: m/z = 496.

合成例(A8)：化合物(H-565)的合成Synthesis Example (A8): Synthesis of Compound (H-565)

使用与合成例(A1)相同的方法来合成化合物(H-565)。EI-MS：m/z＝662.Compound (H-565) was synthesized using the same method as in Synthesis Example (A1). EI-MS: m/z = 662.

合成例(A9)：化合物(H-640)的合成Synthesis Example (A9): Synthesis of Compound (H-640)

使用与合成例(A1)相同的方法来合成化合物(H-640)。EI-MS：m/z＝737.Compound (H-640) was synthesized using the same method as in Synthesis Example (A1). EI-MS: m/z = 737.

合成例(A10)：化合物(H-655)的合成Synthesis Example (A10): Synthesis of Compound (H-655)

使用与合成例(A1)相同的方法来合成化合物(H-655)。Compound (H-655) was synthesized by the same method as in Synthesis Example (A1).

EI-MS：m/z＝610.EI-MS: m/z = 610.

合成例(A11)：化合物(H-688)的合成Synthesis Example (A11): Synthesis of Compound (H-688)

使用与合成例(A1)相同的方法来合成化合物(H-688)。Compound (H-688) was synthesized by the same method as in Synthesis Example (A1).

EI-MS：m/z＝760.EI-MS: m/z = 760.

合成例(A12)：化合物(H-725)的合成Synthesis Example (A12): Synthesis of Compound (H-725)

在氩气环境下，将化合物(H-1)(1g)、5％铂-碳(5％Pt/C、300mg)、重水(D₂O、40ml)、环己烷(cHex、20ml)及异丙醇(IPA(Isopropyl alcohol)、5ml)放入烧瓶中，在100℃下进行加热。在反应后，加入水与氯仿而进行分液提取，利用硫酸镁对有机层进行干燥并加以过滤，然后将有机层浓缩，对所获得的粗体进行再结晶，由此获得化合物(H-725)。Under an argon atmosphere, compound (H-1) (1 g), 5% platinum-carbon (5% Pt/C, 300 mg), heavy water (D₂ O, 40 ml), cyclohexane (cHex, 20 ml) and isopropyl alcohol (IPA (Isopropyl alcohol), 5 ml) were placed in a flask and heated at 100° C. After the reaction, water and chloroform were added to perform liquid separation and extraction, the organic layer was dried over magnesium sulfate and filtered, and then the organic layer was concentrated and the obtained crude product was recrystallized to obtain compound (H-725).

EI-MS：m/z＝492.EI-MS: m/z = 492.

合成例(A13)：化合物(H-771)的合成Synthesis Example (A13): Synthesis of Compound (H-771)

使用与合成例(A1)相同的方法来合成化合物(H-771)。Compound (H-771) was synthesized by the same method as in Synthesis Example (A1).

EI-MS：m/z＝546.EI-MS: m/z = 546.

合成例(A14)：化合物(H-780)的合成Synthesis Example (A14): Synthesis of Compound (H-780)

使用与合成例(A12)相同的方法来合成化合物(H-780)。Compound (H-780) was synthesized by the same method as in Synthesis Example (A12).

EI-MS：m/z＝572.EI-MS: m/z = 572.

合成例(A15)：化合物(H-785)的合成Synthesis Example (A15): Synthesis of Compound (H-785)

使用与合成例(A1)相同的方法来合成化合物(H-785)。EI-MS：m/z＝838.Compound (H-785) was synthesized using the same method as in Synthesis Example (A1). EI-MS: m/z = 838.

合成例(A16)：化合物(H-798)的合成Synthesis Example (A16): Synthesis of Compound (H-798)

使用与合成例(A1)相同的方法来合成化合物(H-798)。EI-MS：m/z＝826.Compound (H-798) was synthesized using the same method as in Synthesis Example (A1). EI-MS: m/z = 826.

合成例(A17)：化合物(H-70)的合成Synthesis Example (A17): Synthesis of Compound (H-70)

使用与合成例(A1)相同的方法来合成化合物(H-70)。Compound (H-70) was synthesized by the same method as in Synthesis Example (A1).

¹H-NMR(CDCl₃)：δ＝8.49(d,1H),8.23(d,1H),8.13(d,1H),8.05(d,1H),7.87(d,2H),7.75(m,4H),7.62(m,4H),7.52(m,4H),7.33(m,4H).¹ H-NMR (CDCl₃ ): δ = 8.49 (d, 1H), 8.23 (d, 1H), 8.13 (d, 1H), 8.05 (d, 1H), 7.87 (d, 2H), 7.75 (m, 4H),7.62(m,4H),7.52(m,4H),7.33(m,4H).

可通过适宜变更原料的化合物，并利用依据所述合成例的方法来合成本发明的其他蒽系化合物。Other anthracene compounds of the present invention can be synthesized by appropriately changing the compounds of the starting materials and using the method according to the above-described synthesis examples.

合成例(B1)：化合物(D-114)的合成Synthesis Example (B1): Synthesis of Compound (D-114)

在氮气环境下，利用冰浴对放入有4-甲氧基水杨酸甲酯(50.0g)、吡啶(脱水、350ml)的烧瓶进行冷却。继而，向所述溶液中滴加三氟甲磺酸酐(154.9g)。在滴加结束后，移去冰浴，并在室温下搅拌2小时，加入水来停止反应。加入甲苯来进行分液，然后利用硅胶短程管柱(洗脱液：甲苯)进行纯化，由此获得4-甲氧基-2-(((三氟甲基)磺酰基)氧基)苯甲酸甲酯(86.0g)。Under nitrogen atmosphere, a flask containing methyl 4-methoxysalicylate (50.0 g) and pyridine (dehydrated, 350 ml) was cooled using an ice bath. Then, trifluoromethanesulfonic anhydride (154.9 g) was added dropwise to the solution. After the addition was completed, the ice bath was removed, and the mixture was stirred at room temperature for 2 hours, and water was added to stop the reaction. Toluene was added for liquid separation, and then the mixture was purified using a silica gel short-path column (eluent: toluene) to obtain methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoate (86.0 g).

在氮气环境下，向4-甲氧基-2-(((三氟甲基)磺酰基)氧基)苯甲酸甲酯(23.0g)、(4-(二苯基氨基)苯基)硼酸(25.4g)、磷酸三钾(31.1g)、甲苯(184ml)、乙醇(27.6ml)及水(27.6ml)的悬浮溶液中加入四(三苯基膦)钯(0)(Pd(PPh₃)₄、2.5g)，并在回流温度下搅拌3小时。将反应液冷却至室温，加入水及甲苯来进行分液，并将有机层的溶媒减压馏去。利用硅胶管柱(洗脱液：庚烷/甲苯混合溶媒)对所获得的固体进行纯化，从而获得4'-(二苯基氨基)-5-甲氧基-[1,1'-联苯]-2-羧酸甲酯(29.7g)。此时，参考《有机化学实验入门(1)-物质处理法与分离纯化法-》化学同人股份有限公司出版、第94页中记载的方法，缓缓地增加洗脱液中的甲苯的比率来使目标物溶出。Under nitrogen atmosphere, tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 , 2.5 g) was added to a suspension of methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoate (23.0 g), (4-(_{diphenylamino} )phenyl)boric acid (25.4 g), tripotassium phosphate (31.1 g), toluene (184 ml), ethanol (27.6 ml) and water (27.6 ml), and stirred at reflux temperature for₃ hours. The reaction solution was cooled to room temperature, water and toluene were added for separation, and the solvent of the organic layer was distilled off under reduced pressure. The obtained solid was purified using a silica gel column (eluent: heptane/toluene mixed solvent) to obtain methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate (29.7 g). At this time, refer to the method described in "Introduction to Organic Chemistry Experiments (1) - Substance Treatment and Separation and Purification Methods -" published by Chemical Co., Ltd., page 94, and gradually increase the ratio of toluene in the eluent to elute the target substance.

在氮气环境下，利用水浴对溶解有4'-(二苯基氨基)-5-甲氧基-[1,1'-联苯]-2-羧酸甲酯(11.4g)的四氢呋喃(THF(Tetrahydrofuran)、111.4ml)溶液进行冷却，并向所述溶液中滴加甲基溴化镁的THF溶液(1.0M、295ml)。在滴加结束后，移去水浴而升温至回流温度，并搅拌4小时。然后，利用冰浴进行冷却，加入氯化铵水溶液来停止反应，并加入乙酸乙酯来进行分液，然后将溶媒减压馏去。利用硅胶管柱(洗脱液：甲苯)对所获得的固体进行纯化，从而获得2-(5'-(二苯基氨基)-5-甲氧基-[1,1'-联苯]-2-基)丙烷-2-醇(8.3g)。Under nitrogen atmosphere, a tetrahydrofuran (THF (Tetrahydrofuran), 111.4 ml) solution in which methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate (11.4 g) was dissolved was cooled in a water bath, and a THF solution of methyl magnesium bromide (1.0 M, 295 ml) was added dropwise to the solution. After the addition was completed, the water bath was removed and the temperature was raised to reflux temperature, and stirred for 4 hours. Then, the mixture was cooled in an ice bath, an aqueous ammonium chloride solution was added to stop the reaction, ethyl acetate was added for liquid separation, and the solvent was then distilled off under reduced pressure. The obtained solid was purified using a silica gel column (eluent: toluene) to obtain 2-(5'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-yl)propan-2-ol (8.3 g).

在氮气环境下且在回流温度下，将放入有2-(5'-(二苯基氨基)-5-甲氧基-[1,1'-联苯]-2-基)丙烷-2-醇(27.0g)、作为催化剂的帝化屈尔(TAYCACURE)-15(帝化股份有限公司、13.5g)及甲苯(162ml)的烧瓶搅拌2小时。将反应液冷却至室温，并使其在硅胶短程管柱(洗脱液：甲苯)中通过而去除帝化屈尔(TAYCACURE)-15，然后将溶媒减压馏去，由此获得6-甲氧基-9,9'-二甲基-N,N-二苯基-9H-芴-2-胺(25.8g)。Under nitrogen atmosphere and at reflux temperature, a flask containing 2-(5'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-yl)propan-2-ol (27.0 g), TAYCACURE-15 (Teika Co., Ltd., 13.5 g) as a catalyst, and toluene (162 ml) was stirred for 2 hours. The reaction solution was cooled to room temperature and passed through a silica gel short-path column (eluent: toluene) to remove TAYCACURE-15, and then the solvent was distilled off under reduced pressure to obtain 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (25.8 g).

在氮气环境下且在回流温度下，将放入有6-甲氧基-9,9'-二甲基-N,N-二苯基-9H-芴-2-胺(25.0g)、吡啶盐酸盐(36.9g)及N-甲基-2-吡咯烷酮(NMP(N-Methyl-2-Pyrrolidone)、22.5ml)的烧瓶搅拌6小时。将反应液冷却至室温，加入水及乙酸乙酯来进行分液。将溶媒减压馏去，然后利用硅胶管柱(洗脱液：甲苯)进行纯化，由此获得7-(二苯基氨基)-9,9'-二甲基-9H-芴-3-醇(22.0g)。Under nitrogen atmosphere and at reflux temperature, a flask containing 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (25.0 g), pyridine hydrochloride (36.9 g) and N-methyl-2-pyrrolidone (NMP (N-Methyl-2-Pyrrolidone), 22.5 ml) was stirred for 6 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added for liquid separation. The solvent was distilled off under reduced pressure, and then purified using a silica gel column (eluent: toluene) to obtain 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (22.0 g).

在氮气环境下且在回流温度下，将放入有7-(二苯基氨基)-9,9'-二甲基-9H-芴-3-醇(14.1g)、2-溴-1,3-二氟苯(3.6g)、碳酸钾(12.9g)及NMP(30ml)的烧瓶加热搅拌5小时。在反应停止后，将反应液冷却至室温，加入水，通过抽吸过滤来采取所析出的沉淀物。依次利用水、甲醇对所获得的沉淀物进行清洗，然后利用硅胶管柱(洗脱液：庚烷/甲苯混合溶媒)进行纯化，从而获得6,6'-((2-溴-1,3-亚苯基)双(氧基))双(9,9-二甲基-N,N-二苯基-9H-芴-2-胺)(12.6g)。Under nitrogen atmosphere and at reflux temperature, a flask containing 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (14.1 g), 2-bromo-1,3-difluorobenzene (3.6 g), potassium carbonate (12.9 g) and NMP (30 ml) was heated and stirred for 5 hours. After the reaction was stopped, the reaction solution was cooled to room temperature, water was added, and the precipitate was collected by suction filtration. The obtained precipitate was washed with water and methanol in sequence, and then purified with a silica gel column (eluent: heptane/toluene mixed solvent) to obtain 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine) (12.6 g).

此时，缓缓地增加洗脱液中的甲苯的比率来使目标物溶出。At this time, the ratio of toluene in the eluent is gradually increased to elute the target substance.

在氮气环境下，将放入有6,6'-((2-溴-1,3-亚苯基)双(氧基))双(9,9-二甲基-N,N-二苯基-9H-芴-2-胺)(11.0g)及二甲苯(60.5ml)的烧瓶冷却至-40℃，并滴加2.6M的正丁基锂的己烷溶液(5.1ml)。在滴加结束后，在-40℃下搅拌0.5小时，然后升温至60℃并搅拌3小时。然后，将反应液减压而将低沸点的成分馏去，然后冷却至-40℃并加入三溴化硼(4.3g)。升温至室温并搅拌0.5小时，然后冷却至0℃并添加N-乙基-N-异丙基丙烷-2-胺(3.8g)，在125℃下加热搅拌8小时。将反应液冷却至室温，加入乙酸钠水溶液来停止反应，然后加入甲苯来进行分液。依次利用硅胶短程管柱、硅胶管柱(洗脱液：庚烷/甲苯＝4/1(体积比)的混合溶液)、活性碳管柱(洗脱液：甲苯)对有机层进行纯化，由此获得化合物(D-114)(1.2g)。Under nitrogen atmosphere, a flask containing 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine) (11.0 g) and xylene (60.5 ml) was cooled to -40°C, and a 2.6M hexane solution of n-butyl lithium (5.1 ml) was added dropwise. After the addition was completed, the mixture was stirred at -40°C for 0.5 hours, and then the temperature was raised to 60°C and stirred for 3 hours. Then, the reaction solution was decompressed to distill off low-boiling components, and then the mixture was cooled to -40°C and boron tribromide (4.3 g) was added. The mixture was heated to room temperature and stirred for 0.5 hours, and then N-ethyl-N-isopropylpropane-2-amine (3.8 g) was added to the mixture and heated and stirred at 125°C for 8 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution was added to stop the reaction, and then toluene was added to separate the liquids. The organic layer was purified using a silica gel short path column, a silica gel column (eluent: a mixed solution of heptane/toluene = 4/1 (volume ratio)), and an activated carbon column (eluent: toluene) in this order to obtain compound (D-114) (1.2 g).

通过NMR测定来确认所获得的化合物(D-114)的结构。The structure of the obtained compound (D-114) was confirmed by NMR measurement.

¹H-NMR(400MHz,CDCl₃)：δ＝8.64(s,2H),7.75(m,3H),7.69(d,2H),7.30(t,8H),7.25(s,2H),7.20(m,10H),7.08(m,6H),1.58(s,12H).¹ H-NMR (400MHz, CDCl₃ ): δ = 8.64 (s, 2H), 7.75 (m, 3H), 7.69 (d, 2H), 7.30 (t, 8H), 7.25 (s, 2H), 7.20 ( m,10H),7.08(m,6H),1.58(s,12H).

合成例(B2)：化合物(D-52)的合成Synthesis Example (B2): Synthesis of Compound (D-52)

在氮气环境下，将3-溴-N,N-二苯基苯胺(35g)、4-叔丁基苯胺(19.3g)、作为钯催化剂的二氯双(二-叔丁基(4-二甲基氨基苯基)膦基)]钯(Pd-132、76mg)、叔丁醇钠(NaOtBu、15.6g)及二甲苯(200ml)放入烧瓶中，在120℃下加热2小时。在反应结束后，向反应液中加入水与乙酸乙酯并加以搅拌，然后将有机层分离并加以水洗。然后，将有机层浓缩，利用硅胶短管柱(洗脱液：甲苯/庚烷＝1/1(体积比))对所获得的粗产物进行纯化，由此获得中间物(I-1)(40g)。Under nitrogen atmosphere, 3-bromo-N,N-diphenylaniline (35 g), 4-tert-butylaniline (19.3 g), dichlorobis(di-tert-butyl(4-dimethylaminophenyl)phosphino)]palladium (Pd-132, 76 mg) as a palladium catalyst, sodium tert-butoxide (NaOtBu, 15.6 g) and xylene (200 ml) were placed in a flask and heated at 120° C. for 2 hours. After the reaction was completed, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated, and the obtained crude product was purified using a silica gel short column (eluent: toluene/heptane = 1/1 (volume ratio)) to obtain intermediate (I-1) (40 g).

在氮气环境下，将中间物(I-1)(10.0g)、中间物(I-2)(12.3g)、作为钯催化剂的Pd-132(0.2g)、NaOtBu(3.7g)及二甲苯(60ml)放入烧瓶中，在120℃下加热1小时。在反应结束后，向反应液中加入水与乙酸乙酯并加以搅拌，然后将有机层分离并加以水洗。然后，将有机层浓缩，利用硅胶短管柱(洗脱液：甲苯/庚烷＝1/4(体积比))对所获得的粗产物进行纯化，由此获得中间物(I-3)(18.5g)。Under nitrogen atmosphere, intermediate (I-1) (10.0 g), intermediate (I-2) (12.3 g), Pd-132 (0.2 g) as a palladium catalyst, NaOtBu (3.7 g) and xylene (60 ml) were placed in a flask and heated at 120° C. for 1 hour. After the reaction was completed, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated, and the obtained crude product was purified using a silica gel short column (eluent: toluene/heptane = 1/4 (volume ratio)), thereby obtaining intermediate (I-3) (18.5 g).

在氮气环境下且在0℃下，向放入有中间物(I-3)(15.0g)及叔丁基苯(100ml)的烧瓶中加入1.56M的叔丁基锂戊烷溶液(50.1ml)。在滴加结束后，升温至70℃并搅拌0.5小时，然后将沸点低于叔丁基苯的成分减压馏去。冷却至-50℃并加入三溴化硼(19.1g)，升温至室温并搅拌0.5小时。然后，再次冷却至0℃并加入N,N-二异丙基乙胺(9.9g)，在室温下搅拌至发热结束，然后升温至100℃并加热搅拌1小时。将反应液冷却至室温，依次加入利用冰浴进行了冷却的乙酸钠水溶液、乙酸乙酯来进行分液。在将有机层浓缩后，利用硅胶短管柱(洗脱液：氯苯)进行纯化。利用甲苯使所获得的粗产物再结晶，由此获得化合物(D-52)(9.6g)。Under nitrogen atmosphere and at 0°C, a 1.56M tert-butyllithium pentane solution (50.1ml) was added to a flask containing intermediate (I-3) (15.0g) and tert-butylbenzene (100ml). After the addition was completed, the temperature was raised to 70°C and stirred for 0.5 hours, and then the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (19.1g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then, the mixture was cooled to 0°C again and N,N-diisopropylethylamine (9.9g) was added, and the mixture was stirred at room temperature until the heat generation was stopped, and then the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution and ethyl acetate cooled by ice bath were added in sequence for separation. After the organic layer was concentrated, it was purified by a short silica gel column (eluent: chlorobenzene). The obtained crude product was recrystallized by toluene, thereby obtaining compound (D-52) (9.6g).

EI-MS：m/z＝812.EI-MS: m/z = 812.

合成例(B3)：化合物(D-7)的合成Synthesis Example (B3): Synthesis of Compound (D-7)

使用与合成例(B2)相同的方法来合成化合物(D-7)。Compound (D-7) was synthesized by the same method as in Synthesis Example (B2).

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(500MHz,CDCl₃)：δ＝1.47(s,36H),2.17(s,3H),5.97(s,2H),6.68(d,2H),7.28(d,4H),7.49(dd,2H),7.67(d,4H),8.97(d,2H).¹ H-NMR (500MHz, CDCl₃ ): δ = 1.47 (s, 36H), 2.17 (s, 3H), 5.97 (s, 2H), 6.68 (d, 2H), 7.28 (d, 4H), 7.49 ( dd,2H),7.67(d,4H),8.97(d,2H).

合成例(B4)：化合物(D-69)的合成Synthesis Example (B4): Synthesis of Compound (D-69)

使用与合成例(B2)相同的方法来合成化合物(D-69)。Compound (D-69) was synthesized by the same method as in Synthesis Example (B2).

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.20(s,9H),1.37(s,18H),1.46(s,9H),1.47(s,9H),2.18(s,3H),5.97(s,1H),6.08(d,1H),6.63(d,1H),6.66(d,1H),7.20(d,2H),7.27(d,2H),7.32(dd,1H),7.48(dd,1H),7.61(t,1H),7.67(d,2H),8.84(d,1H),8.94(d,1H).¹ H-NMR (CDCl₃ ): δ = 1.20 (s, 9H), 1.37 (s, 18H), 1.46 (s, 9H), 1.47 (s, 9H), 2.18 (s, 3H), 5.97 (s, 1H),6.08(d,1H),6.63(d,1H),6.66(d,1H),7.20(d,2H),7.27(d,2H),7.32(dd,1H),7.48(dd,1H ),7.61(t,1H),7.67(d,2H),8.84(d,1H),8.94(d,1H).

合成例(B5)：化合物(D-202)的合成Synthesis Example (B5): Synthesis of Compound (D-202)

使用与合成例(B2)相同的方法来合成化合物(D-202)。Compound (D-202) was synthesized by the same method as in Synthesis Example (B2).

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR：δ＝1.1(s,9H),1.4(s,9H),1.5(s,9H),1.5(s,9H),1.5(s,9H),2.2(s,3H),5.9(s,1H),6.1(s,1H),6.7(m,2H),7.0(d,2H),7.1(d,2H),7.2(d,1H),7.3(m,2H),7.4(m,1H),7.5(m,1H),7.6(dd,1H),7.7(m,3H),8.9(d,1H),8.9(d,1H).¹ H-NMR: δ=1.1(s,9H),1.4(s,9H),1.5(s,9H),1.5(s,9H),1.5(s,9H),2.2(s,3H),5.9 (s,1H),6.1(s,1H),6.7(m,2H),7.0(d,2H),7.1(d,2H),7.2(d,1H),7.3(m,2H),7.4( m,1H),7.5(m,1H),7.6(dd,1H),7.7(m,3H),8.9(d,1H),8.9(d,1H).

合成例(B6)：化合物(D-215)的合成Synthesis Example (B6): Synthesis of Compound (D-215)

使用与合成例(B2)相同的方法来合成化合物(D-215)。Compound (D-215) was synthesized by the same method as in Synthesis Example (B2).

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.21(s,18H),1.36(s,36H),1.48-1.66(m,12H),1.89(s,3H),6.18(s,2H),6.78(s,2H),7.22(d,4H),7.25-7.28(m,2H),7.59(t,2H),8.86(d,2H).¹ H-NMR (CDCl₃ ): δ = 1.21 (s, 18H), 1.36 (s, 36H), 1.48-1.66 (m, 12H), 1.89 (s, 3H), 6.18 (s, 2H), 6.78 ( s,2H),7.22(d,4H),7.25-7.28(m,2H),7.59(t,2H),8.86(d,2H).

合成例(B7)：化合物(D-201)的合成Synthesis Example (B7): Synthesis of Compound (D-201)

使用与合成例(B2)相同的方法来合成化合物(D-201)。Compound (D-201) was synthesized by the same method as in Synthesis Example (B2).

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝0.62(t,6H),0.75(t,6H),1.29(s,12H),1.43(s,12H),1.62(q,4H),1.75(q,4H),5.63(s,2H),6.70(d,2H),6.86(m,2H),6.92(d,4H),7.05(m,4H),7.14(d,4H),7.38(m,6H),8.85(d,2H).¹ H-NMR (CDCl₃ ): δ = 0.62 (t, 6H), 0.75 (t, 6H), 1.29 (s, 12H), 1.43 (s, 12H), 1.62 (q, 4H), 1.75 (q, 4H),5.63(s,2H),6.70(d,2H),6.86(m,2H),6.92(d,4H),7.05(m,4H),7.14(d,4H),7.38(m,6H ),8.85(d,2H).

合成例(B8)：化合物(D-270)的合成Synthesis Example (B8): Synthesis of Compound (D-270)

使用与合成例(B2)相同的方法来合成化合物(D-270)。Compound (D-270) was synthesized by the same method as in Synthesis Example (B2).

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.32(s,18H),1.46(s,18H),5.55(s,2H).¹ H-NMR (CDCl₃ ): δ = 1.32 (s, 18H), 1.46 (s, 18H), 5.55 (s, 2H).

合成例(B9)：化合物(D-206)的合成Synthesis Example (B9): Synthesis of Compound (D-206)

使用与合成例(B2)相同的方法来合成化合物(D-206)。Compound (D-206) was synthesized by the same method as in Synthesis Example (B2).

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.08(s,6H),1.27(s,6H),1.42(s,6H),1.46(s,9H),1.47(s,9H),1.48(s,6H),1.69-1.81(m,8H),2.18(s,3H),5.97(s,1H),6.06(s,1H),6.52(s,1H),6.67(d,1H),7.08(dd,1H),7.25-7.29(m,3H),7.48(dd,1H),7.59(d,1H),7.67(d,2H),8.89(s,1H),8.97(d,1H).¹ H-NMR (CDCl₃ ): δ=1.08(s,6H),1.27(s,6H),1.42(s,6H),1.46(s,9H),1.47(s,9H),1.48(s, 6H),1.69-1.81(m,8H),2.18(s,3H),5.97(s,1H),6.06(s,1H),6.52(s,1H),6.67(d,1H),7.08(dd ,1H),7.25-7.29(m,3H),7.48(dd,1H),7.59(d,1H),7.67(d,2H),8.89(s,1H),8.97(d,1H).

合成例(B10)：化合物(D-18)的合成Synthesis Example (B10): Synthesis of Compound (D-18)

在氮气环境下，将放入有中间物(I-4)(15g)及甲苯(300ml)的烧瓶升温至70℃，使中间物(I-4)完全溶解。将烧瓶冷却至-20℃，然后加入四甲基乙二胺(TMEDA(Tetramethylethylenediamine)、20.8g)、1.00M的仲丁基锂的环己烷及正己烷混合溶液(89ml)。升温至0℃并搅拌3小时，然后加入2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼烷(33.3g)，并回流1小时。加入水及甲苯来进行分液，将有机层的溶媒减压馏去。使用索米克斯(Solmix)A-11(商品名：日本醇销售股份有限公司)对所获得的固体进行清洗，然后溶解于甲苯中，在0℃下放置1小时。将所析出的沉淀过滤分离，使滤液在硅胶管柱(洗脱液：甲苯/庚烷＝1/5混合溶媒(体积比))中通过。在将溶媒馏去后，利用乙酸乙酯及索米克斯(Solmix)A-11的混合溶媒进行再沉淀，由此以白色固体的形式获得中间物(I-5)(9.5g)。Under nitrogen atmosphere, heat the flask containing intermediate (I-4) (15 g) and toluene (300 ml) to 70°C to completely dissolve the intermediate (I-4). Cool the flask to -20°C, then add tetramethylethylenediamine (TMEDA (Tetramethylethylenediamine), 20.8 g), 1.00 M sec-butyllithium in cyclohexane and n-hexane mixed solution (89 ml). Heat to 0°C and stir for 3 hours, then add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (33.3 g), and reflux for 1 hour. Add water and toluene to separate the liquids, and distill the solvent of the organic layer under reduced pressure. Use Solmix A-11 (trade name: Japan Alcohol Sales Co., Ltd.) to wash the obtained solid, then dissolve it in toluene and leave it at 0°C for 1 hour. The precipitate was separated by filtration, and the filtrate was passed through a silica gel column (eluent: toluene/heptane = 1/5 mixed solvent (volume ratio)). After the solvent was distilled off, reprecipitation was performed using a mixed solvent of ethyl acetate and Solmix A-11 to obtain intermediate (I-5) (9.5 g) as a white solid.

在氮气环境下且在120℃下，将放入有中间物(I-5)(8.7g)、氯化铝(12.5g)、N,N-二异丙基乙胺(DIPEA(N,N-Diisopropyl ethyl amine)、6.0g)及氯苯(44ml)的烧瓶搅拌1小时。将冷却至室温的反应混合液注入冰水(200ml)中，加入甲苯来提取有机层。将有机层的溶媒减压馏去，使所获得的固体溶解于氯仿中，并使其在硅胶短程管柱(洗脱液：甲苯)中通过。将溶媒减压馏去，使用环戊基甲基醚及索米克斯(Solmix)A-11使所获得的粗产物再沉淀，由此以黄色固体的形式获得化合物(D-18)(6.2g、产率70％)。Under nitrogen atmosphere and at 120°C, a flask containing intermediate (I-5) (8.7 g), aluminum chloride (12.5 g), DIPEA (N,N-Diisopropyl ethyl amine), 6.0 g, and chlorobenzene (44 ml) was stirred for 1 hour. The reaction mixture cooled to room temperature was poured into ice water (200 ml), and toluene was added to extract the organic layer. The solvent of the organic layer was distilled off under reduced pressure, and the obtained solid was dissolved in chloroform and passed through a silica gel short-path column (eluent: toluene). The solvent was distilled off under reduced pressure, and the obtained crude product was reprecipitated using cyclopentyl methyl ether and Solmix A-11, thereby obtaining compound (D-18) (6.2 g, yield 70%) as a yellow solid.

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(400MHz,CDCl₃)：δ＝8.95(d,2H),7.45(dd,6H),7.13(d,4H),7.08-7.04(m,4H),6.95-6.88(m,6H),6.75(d,2H),5.56(s,2H),1.46(s,18H),1.33(s,18H).¹ H-NMR (400MHz, CDCl₃ ): δ = 8.95 (d, 2H), 7.45 (dd, 6H), 7.13 (d, 4H), 7.08-7.04 (m, 4H), 6.95-6.88 (m, 6H) ),6.75(d,2H),5.56(s,2H),1.46(s,18H),1.33(s,18H).

合成例(B11)：化合物(D-155)的合成Synthesis Example (B11): Synthesis of Compound (D-155)

在氮气环境下且在回流温度下，将放入有7-(二苯基氨基)-9,9'-二甲基-9H-芴-3-醇(9.0g)、1,2-二溴-3-氟苯(7.9g)、碳酸钾(8.2g)及NMP(45ml)的烧瓶加热搅拌2小时。在反应停止后，将反应液冷却至室温，加入水，通过抽吸过滤来采取所析出的沉淀物。依次利用水、索米克斯(Solmix)对所获得的沉淀物进行清洗，然后利用硅胶管柱(洗脱液：庚烷/甲苯＝3/1(体积比))进行纯化，由此获得6-(2,3-二溴苯氧基)-9,9-二甲基-N,N-二苯基-9H-芴-2-胺(12.4g、产率：84.8％)。Under nitrogen atmosphere and at reflux temperature, a flask containing 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (9.0 g), 1,2-dibromo-3-fluorobenzene (7.9 g), potassium carbonate (8.2 g) and NMP (45 ml) was heated and stirred for 2 hours. After the reaction was stopped, the reaction solution was cooled to room temperature, water was added, and the precipitate was collected by suction filtration. The obtained precipitate was washed with water and Solmix in sequence, and then purified with a silica gel column (eluent: heptane/toluene = 3/1 (volume ratio)) to obtain 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (12.4 g, yield: 84.8%).

在氮气环境下且在80℃下，将放入有6-(2,3-二溴苯氧基)-9,9-二甲基-N,N-二苯基-9H-芴-2-胺(10.0g)、二([1,1'-联苯]-4-基)胺(5.3g)、乙酸钯(0.15g)、二环己基(2',6'-二异丙氧基-[1，1'-联苯]-2-基)膦(0.61g)、NaOtBu(2.4g)及甲苯(35ml)的烧瓶加热6小时。在将反应液冷却至室温后，加入水及甲苯来进行分液。进而，利用硅胶管柱(洗脱液：庚烷/甲苯＝2/1(体积比))进行纯化，由此获得6-(2-溴-3-(二([1,1'-联苯]-4-基)氨基)苯氧基)-9,9-二甲基-N,N-二苯基-9H-芴-2-胺(7.4g、产率：53.1％)。Under nitrogen atmosphere, a flask containing 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (10.0 g), di([1,1'-biphenyl]-4-yl)amine (5.3 g), palladium acetate (0.15 g), dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (0.61 g), NaOtBu (2.4 g) and toluene (35 ml) was heated at 80° C. for 6 hours. After the reaction solution was cooled to room temperature, water and toluene were added for liquid separation. Furthermore, the product was purified using a silica gel column (eluent: heptane/toluene = 2/1 (volume ratio)) to obtain 6-(2-bromo-3-(di([1,1'-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (7.4 g, yield: 53.1%).

在氮气环境下，将6-(2-溴-3-(二([1,1'-联苯]-4-基)氨基)苯氧基)-9,9-二甲基-N,N-二苯基-9H-芴-2-胺(7.9g)及THF(42ml)放入烧瓶中，冷却至-40℃，并滴加1.6M的正丁基锂己烷溶液(6ml)。在滴加结束后，在所述温度下搅拌1小时，然后加入三甲基硼酸酯(1.7g)。升温至室温并搅拌2小时。然后，缓缓地滴加水(100ml)。接着，利用乙酸乙酯对反应混合液进行提取，利用无水硫酸钠进行干燥，然后去除干燥剂，由此获得二甲基(2-(二([1,1'-联苯]-4-基)氨基)-6-((7-(二苯基氨基)-9,9-二甲基-9H-芴-3-基)氧基)苯基)硼酸酯(7.0g、产率：100％)。Under nitrogen atmosphere, 6-(2-bromo-3-(di([1,1'-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (7.9 g) and THF (42 ml) were placed in a flask, cooled to -40°C, and 1.6 M n-butyl lithium hexane solution (6 ml) was added dropwise. After the addition was completed, the mixture was stirred at the temperature for 1 hour, and then trimethylborate (1.7 g) was added. The mixture was heated to room temperature and stirred for 2 hours. Then, water (100 ml) was slowly added dropwise. Next, the reaction mixture was extracted with ethyl acetate, dried with anhydrous sodium sulfate, and then the desiccant was removed to obtain dimethyl (2-(di([1,1'-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluoren-3-yl)oxy)phenyl)borate (7.0 g, yield: 100%).

在氮气环境下，将二甲基(2-(二([1,1'-联苯]-4-基)氨基)-6-((7-(二苯基氨基)-9,9-二甲基-9H-芴-3-基)氧基)苯基)硼酸酯(6.5g)、氯化铝(10.3g)及甲苯(39ml)放入烧瓶中，并搅拌3分钟。然后，加入N-乙基-N-异丙基丙烷-2-胺(2.5g)，在105℃下加热搅拌1小时。在加热结束后，将反应液冷却并添加冰水(20ml)。然后，利用甲苯对反应混合液进行提取，依次利用硅胶短程管柱(洗脱液：甲苯)、硅胶管柱(洗脱液：庚烷/甲苯＝3/1(体积比))对有机层进行纯化，然后利用庚烷进行再沉淀，进而，利用NH2硅胶管柱(洗脱液：庚烷/甲苯＝1/1(体积比))进行纯化。最后进行升华纯化，由此获得化合物(D-155)(0.74g、产率：12.3％)。Under nitrogen atmosphere, dimethyl (2-(di([1,1'-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluoren-3-yl)oxy)phenyl)borate (6.5 g), aluminum chloride (10.3 g) and toluene (39 ml) were placed in a flask and stirred for 3 minutes. Then, N-ethyl-N-isopropylpropane-2-amine (2.5 g) was added, and the mixture was heated and stirred at 105° C. for 1 hour. After the heating was completed, the reaction solution was cooled and ice water (20 ml) was added. Then, the reaction mixture was extracted with toluene, and the organic layer was purified using a silica gel short-path column (eluent: toluene) and a silica gel column (eluent: heptane/toluene = 3/1 (volume ratio)) in sequence, and then reprecipitated with heptane, and further purified with an NH2 silica gel column (eluent: heptane/toluene = 1/1 (volume ratio)). Finally, sublimation purification was performed to obtain Compound (D-155) (0.74 g, yield: 12.3%).

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝9.22(s,1H),8.78(s,1H),7.96(d,2H),7.80～7.77(m,6H),7.71(d,1H),7.59～7.44(m,8H),7.39(t,1H),7.32～7.29(m,4H),7.71(d,1H),7.19(dd,4H),7.12～7.06(m,4H),7.00(d,1H),6.45(d,1H),1.57(s,6H).¹ H-NMR (CDCl₃ ): δ = 9.22 (s, 1H), 8.78 (s, 1H), 7.96 (d, 2H), 7.80～7.77 (m, 6H), 7.71 (d, 1H), 7.59～ 7.44(m,8H),7.39(t,1H),7.32～7.29(m,4H),7.71(d,1H),7.19(dd,4H),7.12～7.06(m,4H),7.00(d, 1H),6.45(d,1H),1.57(s,6H).

合成例(B12)：化合物(D-249)的合成Synthesis Example (B12): Synthesis of Compound (D-249)

使用与合成例(B2)相同的方法来合成化合物(D-249)。Compound (D-249) was synthesized by the same method as in Synthesis Example (B2).

EI-MS：m/z＝756.EI-MS: m/z = 756.

合成例(B13)：化合物(D-255)的合成Synthesis Example (B13): Synthesis of Compound (D-255)

使用与合成例(B2)相同的方法来合成化合物(D-255)。EI-MS：m/z＝811.Compound (D-255) was synthesized using the same method as in Synthesis Example (B2). EI-MS: m/z = 811.

合成例(B14)：化合物(D-253)的合成Synthesis Example (B14): Synthesis of Compound (D-253)

使用与合成例(B2)相同的方法来合成化合物(D-253)。EI-MS：m/z＝889.Compound (D-253) was synthesized using the same method as in Synthesis Example (B2). EI-MS: m/z = 889.

合成例(B15)：化合物(D-254)的合成Synthesis Example (B15): Synthesis of Compound (D-254)

使用与合成例(B2)相同的方法来合成化合物(D-254)。EI-MS：m/z＝867.Compound (D-254) was synthesized using the same method as in Synthesis Example (B2). EI-MS: m/z = 867.

合成例(B16)：化合物(D-264)的合成Synthesis Example (B16): Synthesis of Compound (D-264)

使用与合成例(B2)相同的方法来合成化合物(D-264)。Compound (D-264) was synthesized by the same method as in Synthesis Example (B2).

EI-MS：m/z＝944.EI-MS: m/z = 944.

合成例(B17)：化合物(D-293)的合成Synthesis Example (B17): Synthesis of Compound (D-293)

在氮气环境下且在150℃下，将三对甲苯基胺(0.287g、1.00mmol)、三碘化硼(0.783g、2.00mmol)及邻二氯苯(10.0mL)加热搅拌2小时。将反应液冷却至室温，加入2-异丙烯基苯基溴化镁(5.25mL、1.2M、6.30mmol)。然后，使用硅酸镁短程管柱(洗脱液：甲苯)进行过滤，将溶媒减压馏去。利用己烷对所获得的粗产物进行清洗，由此进行分离纯化，从而以产率75％获得0.309g的2,8-二甲基-10-(2-(丙-1-烯-2-基)苯基)-5-(对甲苯基)-5,10-二氢二苯并[b,e][1,4]氮杂硼烷。Under nitrogen atmosphere and at 150°C, tri-p-tolylamine (0.287 g, 1.00 mmol), boron triiodide (0.783 g, 2.00 mmol) and o-dichlorobenzene (10.0 mL) were heated and stirred for 2 hours. The reaction solution was cooled to room temperature, and 2-isopropenylphenylmagnesium bromide (5.25 mL, 1.2 M, 6.30 mmol) was added. Then, the mixture was filtered using a magnesium silicate short-path column (eluent: toluene), and the solvent was distilled off under reduced pressure. The obtained crude product was washed with hexane, and then separated and purified to obtain 0.309 g of 2,8-dimethyl-10-(2-(prop-1-en-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azaborane with a yield of 75%.

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝2.05(s,3H),2.31(s,6H),2.54(s,3H),4.78(s,2H),6.74(d,2H),7.20-7.28(m,4H),7.37-7.48(m,5H),7.56(d,1H),7.68(s,2H).¹ H-NMR (CDCl₃ ): δ=2.05(s,3H),2.31(s,6H),2.54(s,3H),4.78(s,2H),6.74(d,2H),7.20-7.28( m,4H),7.37-7.48(m,5H),7.56(d,1H),7.68(s,2H).

¹³C-NMR(CDCl₃)：δ＝20.6(s,2C),21.3(s,1C),23.8(s,1C),116.7(s,2C),116.9(s,1C),126.0(d,2C),126.8(s,1C),128.2(s,2C),130.0(d,4C),131.4(d,4C),133.0(s,1C),133.7(s,2C),136.4(s,2C),138.6(s,1C),139.3(s,1C),145.1(s,1C),147.0(d,2C).¹³ C-NMR (CDCl₃ ): δ = 20.6 (s, 2C), 21.3 (s, 1C), 23.8 (s, 1C), 116.7 (s, 2C), 116.9 (s, 1C), 126.0 (d, 2C),126.8(s,1C),128.2(s,2C),130.0(d,4C),131.4(d,4C),133.0(s,1C),133.7(s,2C),136.4(s,2C) ),138.6(s,1C),139.3(s,1C),145.1(s,1C),147.0(d,2C).

在氮气环境下且在95℃下，将2,8-二甲基-10-(2-(丙-1-烯-2-基)苯基)-5-(对甲苯基)-5,10-二氢二苯并[b,e][1,4]氮杂硼烷(82.2mg、0.20mmol)、三氟甲磺酸钪(0.100g、0.20mmol)及1,2-二氯乙烷(55.0mL)加热搅拌24小时。将反应液冷却至室温，然后使用硅酸镁短程管柱(洗脱液：甲苯)进行过滤，将溶媒减压馏去。利用硅胶管柱(洗脱液：己烷/甲苯＝6/1(体积比))对所获得的粗产物进行分离纯化，以产率39％获得32.0mg的化合物(D-293)。2,8-dimethyl-10-(2-(prop-1-en-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azaborane (82.2 mg, 0.20 mmol), scandium trifluoromethanesulfonate (0.100 g, 0.20 mmol) and 1,2-dichloroethane (55.0 mL) were heated and stirred for 24 hours under a nitrogen environment at 95°C. The reaction solution was cooled to room temperature, filtered using a magnesium silicate short-path column (eluent: toluene), and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified using a silica gel column (eluent: hexane/toluene = 6/1 (volume ratio)), and 32.0 mg of compound (D-293) was obtained with a yield of 39%.

通过NMR测定来确认所获得的化合物的结构。The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.98(s,6H),2.48(s,3H),2.53(s,3H),2.76(s,3H),6.61(d,1H),6.75(d,1H),7.14-7.31(m,4H),7.40-7.47(m,3H),7.57(dt,1H),7.81(d,1H),8.44(d,1H),8.50(s,1H).¹ H-NMR (CDCl₃ ): δ = 1.98 (s, 6H), 2.48 (s, 3H), 2.53 (s, 3H), 2.76 (s, 3H), 6.61 (d, 1H), 6.75 (d, 1H),7.14-7.31(m,4H),7.40-7.47(m,3H),7.57(dt,1H),7.81(d,1H),8.44(d,1H),8.50(s,1H).

¹³C-NMR(CDCl₃)：δ＝20.9(s,1C),21.4(s,1C),24.3(s,1C),32.6(s,2C),43.5(s,1C),114.0(s,1C),116.6(s,1C),124.7(s,1C),125.8(s,1C),127.0(s,1C),128.4(s,2C),130.1(s,2C),130.5(s,1C),131.4(s,2C),133.0(s,1C),135.2(s,1C),135.5(s,1C),137.7(s,1C),138.4(s,1C),139.5(s,1C),144.3(s,1C),145.4(s,1C),151.4(s,1C),159.5(s,1C).¹³ C-NMR (CDCl₃ ): δ = 20.9 (s, 1C), 21.4 (s, 1C), 24.3 (s, 1C), 32.6 (s, 2C), 43.5 (s, 1C), 114.0 (s, 1C),116.6(s,1C),124.7(s,1C),125.8(s,1C),127.0(s,1C),128.4(s,2C),130.1(s,2C), 130.5(s,1C),131.4(s,2C),133.0(s,1C),135.2(s,1C),135.5(s,1C),137.7(s,1C),138.4(s,1C),139.5 (s,1C),144.3(s,1C),145.4(s,1C),151.4(s,1C),159.5(s,1C).

可通过适宜变更原料的化合物，并利用依据所述合成例的方法来合成本发明的其他多环芳香族化合物。Other polycyclic aromatic compounds of the present invention can be synthesized by appropriately changing the raw material compounds and using the method according to the above-described synthesis examples.

接着，为了更详细地说明本发明而示出使用了本发明的化合物的有机EL元件的实施例，但本发明并不限定于这些。Next, examples of organic EL devices using the compounds of the present invention are shown in order to explain the present invention in more detail, but the present invention is not limited to these.

＜蒸镀型有机EL元件的评价＞＜Evaluation of vapor deposition type organic EL elements＞

制作实施例1～实施例42及比较例1～比较例4的有机EL元件，分别测定1000cd/m²发光时的特性即驱动电压(V)、外部量子效率(％)及保持初始亮度的90％以上的亮度的时间(元件寿命)。Organic EL elements of Examples 1 to 42 and Comparative Examples 1 to 4 were prepared, and their characteristics when emitting light at 1000 cd/^m2 , namely, driving voltage (V), external quantum efficiency (%), and time for maintaining brightness above 90% of the initial brightness (element life) were measured.

发光元件的量子效率有内部量子效率与外部量子效率，内部量子效率表示作为电子(或空穴)而注入至发光元件的发光层的外部能量纯粹地转换为光子的比例。另一方面，外部量子效率是基于将所述光子释放至发光元件的外部的量而算出，发光层中所产生的光子的一部分在发光元件的内部持续被吸收或者反射而不释放至发光元件的外部，因此外部量子效率低于内部量子效率。The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency. The internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the light-emitting element as electrons (or holes) that is purely converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons released to the outside of the light-emitting element. A portion of the photons generated in the light-emitting layer is continuously absorbed or reflected inside the light-emitting element and is not released outside the light-emitting element. Therefore, the external quantum efficiency is lower than the internal quantum efficiency.

外部量子效率的测定方法如下所述。使用爱德万测试(Advantest)公司制造的电压/电流产生器R6144，施加元件的亮度成为1000cd/m²的电压而使元件发光。使用拓普康(TOPCON)公司制造的分光放射亮度计SR-3AR，自相对于发光面垂直的方向测定可见光区域的分光放射亮度。假定发光面为完全扩散面，所测定的各波长成分的分光放射亮度的值除以波长能量并乘以π而获得的数值为各波长下的光子数。继而，在所观测的全波长区域累计光子数，并设为自元件释放出的总光子数。将施加电流值除以元电荷(elementary charge)而获得的数值设为注入至元件的载子(carrier)数，自元件释放出的总光子数除以注入至元件的载子数而获得的数值为外部量子效率。The determination method of external quantum efficiency is as follows. Using the voltage/current generator R6144 manufactured by Advantest, the brightness of the component is applied to a voltage of 1000cd/^m2 to make the component emit light. Using the spectroradiometer SR-3AR manufactured by TOPCON, the spectroradiometric brightness of the visible light region is measured from the direction perpendicular to the luminous surface. Assuming that the luminous surface is a completely diffuse surface, the value of the spectroradiometric brightness of each wavelength component measured is divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Then, the number of photons is accumulated in the observed full wavelength region and is set to the total number of photons released from the component. The value obtained by dividing the applied current value by the elementary charge is set to the number of carriers injected into the component, and the value obtained by dividing the total number of photons released from the component by the number of carriers injected into the component is the external quantum efficiency.

＜实施例1＞<Example 1>

将实施例1所制造的有机EL元件的层结构示于表1中。Table 1 shows the layer structure of the organic EL device produced in Example 1.

[表1][Table 1]

以将通过溅镀而制膜为180nm的厚度的ITO研磨至150nm的26mm×28mm×0.7mm的玻璃基板(光科学(Opto Science)(股)制造)为透明支撑基板。将所述透明支撑基板固定于市售的蒸镀装置(长洲产业(股)制造)的基板固定器上，并装设分别放入有HI、HAT-CN、HT-1、HT-2、化合物(H-1)、化合物(D-114)、ET-1及ET-2的钽制蒸镀用舟皿；分别放入有Liq、镁及银的氮化铝制蒸镀用舟皿。A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) on which ITO film having a thickness of 180 nm was formed by sputtering and polished to 150 nm was used as a transparent support substrate. The transparent support substrate was fixed on a substrate holder of a commercially available vapor deposition apparatus (manufactured by Nagasu Industry Co., Ltd.), and a tantalum vapor deposition boat containing HI, HAT-CN, HT-1, HT-2, compound (H-1), compound (D-114), ET-1, and ET-2, respectively, and an aluminum nitride vapor deposition boat containing Liq, magnesium, and silver, respectively, were installed.

在透明支撑基板的ITO膜上依次形成下述各层。将真空槽减压至5×10^-4Pa，首先，对HI进行加热、且以使膜厚成为40nm的方式进行蒸镀来形成空穴注入层1。接着，对HAT-CN进行加热、且以使膜厚成为5nm的方式进行蒸镀来形成空穴注入层2。接着，对HT-1进行加热、且以使膜厚成为45nm的方式进行蒸镀来形成空穴传输层1。接着，对HT-2进行加热、且以使膜厚成为10nm的方式进行蒸镀来形成空穴传输层2。接着，对化合物(H-1)与化合物(D-114)同时进行加热、且以使膜厚成为25nm的方式进行蒸镀来形成发光层。以使化合物(H-1)与化合物(D-114)的质量比成为约98比2的方式调节蒸镀速度。接着，对ET-1进行加热、且以使膜厚成为5nm的方式进行蒸镀来形成电子传输层1。接着，对ET-2与Liq同时进行加热、且以使膜厚成为25nm的方式进行蒸镀来形成电子传输层2。以使ET-2与Liq的质量比成为约50比50的方式调节蒸镀速度。各层的蒸镀速度为0.01nm/sec～1nm/sec。然后，对Liq进行加热、且以使膜厚成为1nm的方式以0.01nm/sec～0.1nm/sec的蒸镀速度进行蒸镀，继而，对镁与银同时进行加热、且以使膜厚成为100nm的方式进行蒸镀来形成阴极，从而获得有机EL元件。此时，以使镁与银的原子数比成为10比1的方式在0.1nm/sec～10nm/sec之间调节蒸镀速度。The following layers are formed in sequence on the ITO film of the transparent supporting substrate. The vacuum tank is depressurized to 5×10^-4 Pa. First, HI is heated and vapor-deposited in a manner that the film thickness is 40 nm to form a hole injection layer 1. Next, HAT-CN is heated and vapor-deposited in a manner that the film thickness is 5 nm to form a hole injection layer 2. Next, HT-1 is heated and vapor-deposited in a manner that the film thickness is 45 nm to form a hole transport layer 1. Next, HT-2 is heated and vapor-deposited in a manner that the film thickness is 10 nm to form a hole transport layer 2. Next, compound (H-1) and compound (D-114) are heated at the same time and vapor-deposited in a manner that the film thickness is 25 nm to form a light-emitting layer. The vapor deposition rate is adjusted so that the mass ratio of compound (H-1) to compound (D-114) is about 98 to 2. Next, ET-1 is heated and vapor-deposited in a manner that the film thickness is 5 nm to form an electron transport layer 1. Next, ET-2 and Liq are heated simultaneously and vapor-deposited in a manner that the film thickness becomes 25nm to form an electron transport layer 2. The vapor deposition rate is adjusted so that the mass ratio of ET-2 to Liq is about 50 to 50. The vapor deposition rate of each layer is 0.01nm/sec to 1nm/sec. Then, Liq is heated and vapor-deposited at a vapor deposition rate of 0.01nm/sec to 0.1nm/sec so that the film thickness becomes 1nm, and then magnesium and silver are heated simultaneously and vapor-deposited in a manner that the film thickness becomes 100nm to form a cathode, thereby obtaining an organic EL element. At this time, the vapor deposition rate is adjusted between 0.1nm/sec and 10nm/sec so that the atomic number ratio of magnesium to silver becomes 10 to 1.

将ITO电极作为阳极、将镁/银电极作为阴极来施加直流电压，并测定1000cd/m²发光时的特性，结果获得蓝色发光。驱动电压为4.21V，外部量子效率为6.78％，元件寿命为263小时。The ITO electrode was used as the anode and the magnesium/silver electrode was used as the cathode. A DC voltage was applied and the characteristics of the luminescence at 1000 cd/m² were measured. The result was blue luminescence. The driving voltage was 4.21 V, the external quantum efficiency was 6.78%, and the device life was 263 hours.

示出在实施例1中所制作的有机EL元件中的各层的材料。“HI”为N⁴,N⁴'-二苯基-N⁴,N⁴'-双(9-苯基-9H-咔唑-3-基)-[1,1'-联苯基]-4,4'-二胺，“HAT-CN”为1,4,5,8,9,12-六氮杂三亚苯六碳腈，“HT-1”为N-([1,1'-联苯]-4-基)-9,9-二甲基-N-(4-(9-苯基-9H-咔唑-3-基)苯基)-9H-芴-2-胺，“HT-2”为N,N-双(4-(二苯并[b,d]呋喃-4-基)苯基)-[1,1'：4',1”-三联苯基]-4-胺。另外，“ET-1”为1-(4-(10-([1,1'-联苯]-4-基)蒽-9-基)苯基)-2-乙基-1H-苯并[d]咪唑，“ET-2”为9,9'-[(5-(6-(1,1'-联苯)-4-基)-2-苯基嘧啶-4-基)-1,3-亚苯基]双(9H-咔唑)。以下与“Liq”以及后述的比较实施例中所使用的比较化合物(1)～比较化合物(4)一起示出化学结构。The materials of each layer in the organic EL element produced in Example 1 are shown. "HI" is N⁴ ,N⁴ '-diphenyl-N⁴ ,N⁴ '-bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, "HT-1" is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, and "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1 "-Triphenyl]-4-amine. In addition, "ET-1" is 1-(4-(10-([1,1'-biphenyl]-4-yl)anthracene-9-yl)phenyl)-2-ethyl-1H-benzo[d]imidazole, and "ET-2" is 9,9'-[(5-(6-(1,1'-biphenyl)-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene]bis(9H-carbazole). The chemical structure is shown below together with "Liq" and comparative compounds (1) to (4) used in the comparative examples described below.

＜实施例2～实施例49及比较例1～比较例4＞<Example 2 to Example 49 and Comparative Examples 1 to 4>

利用与实施例1相同的步骤来制作有机EL元件(其中，依据下述表2A～表2D来变更发光层中的主体与掺杂剂的组合)，并测定EL特性。An organic EL device was produced by the same procedure as in Example 1 (wherein the combination of the host and the dopant in the light-emitting layer was changed according to Tables 2A to 2D below), and the EL characteristics were measured.

[表2A][Table 2A]

[表2B][Table 2B]

[表2C][Table 2C]

[表2D][Table 2D]

以上，对本发明的化合物的一部分进行作为有机EL元件用材料的评价，示出为优异的材料，但未进行评价的其他化合物也为具有相同的基本骨架且整体而言也具有类似的结构的化合物，对于本领域技术人员而言，可同样地理解为是优异的有机EL元件用材料。As mentioned above, a part of the compounds of the present invention were evaluated as materials for organic EL devices and were shown to be excellent materials, but other compounds that were not evaluated also have the same basic skeleton and similar structures as a whole, and for those skilled in the art, they can be similarly understood as excellent materials for organic EL devices.

[产业上的可利用性][Industrial Applicability]

根据本发明的优选形态，通过制作包括含有特定结构的蒽系化合物与多环芳香族化合物的发光层的有机EL元件，可提供驱动电压、量子效率及元件寿命优异的有机EL元件。According to a preferred embodiment of the present invention, an organic EL element having excellent driving voltage, quantum efficiency and element life can be provided by manufacturing an organic EL element including a light-emitting layer containing an anthracene compound and a polycyclic aromatic compound of a specific structure.

Claims (24)

Translated fromChinese

1.一种有机电场发光元件，包括：一对电极，包含阳极及阴极；以及发光层，配置于所述一对电极间，且所述有机电场发光元件中，1. An organic electroluminescent element, comprising: a pair of electrodes, including an anode and a cathode; and a light-emitting layer, disposed between the pair of electrodes, wherein:所述发光层包含下述式(H)所表示的蒽系化合物与作为下述式(D)所表示的单量体或具有多个下述式(D)所表示的部分结构的多聚体的多环芳香族化合物；The light-emitting layer comprises an anthracene compound represented by the following formula (H) and a polycyclic aromatic compound which is a monomer represented by the following formula (D) or a polymer having a plurality of partial structures represented by the following formula (D);式(H)中，In formula (H),R¹～R¹⁰分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，R¹ to R¹⁰ are each independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl,其中，R¹～R¹⁰的任意n个构成L，Among them, any n of R¹ to R¹⁰ constitute L,R²¹～R³⁰分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，R²¹ to R³⁰ are each independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl,R²¹～R³⁰中的邻接的基彼此可键结而形成芳基环或杂芳基环，所形成的环中的至少一个氢能由可经烷基或环烷基取代的芳基、可经烷基或环烷基取代的杂芳基、烷基或环烷基取代，Adjacent groups in R²¹ to R³⁰ may be bonded to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring may be substituted by an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group,其中，R²¹～R³⁰的任意一个构成L，Among them, any one of R²¹ to R³⁰ constitutes L,X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂、＞Si(-R)₂或＞Se，所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，X is independently >O, >S, >NR, >C(-R)₂ , >Si(-R)₂ or >Se, and R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl,作为X的所述＞C(-R)₂或＞Si(-R)₂中的两个R可相互键结而形成环，The two Rs in the >C(-R)₂ or >Si(-R)₂ as X may be bonded to each other to form a ring,作为X的所述＞N-R的R可通过连结基或单键而与R²¹或R³⁰键结，The R of the >NR as X may be bonded to R²¹ or R³⁰ via a linking group or a single bond,L与R¹～R¹⁰的任一个所键结的碳原子及R²¹～R³⁰的任一个所键结的碳原子键结，L is bonded to the carbon atom to which any one of R¹ to R¹⁰ is bonded and to the carbon atom to which any one of R²¹ to R³⁰ is bonded,L为单键、亚烷基、可由烷基或环烷基取代的亚芳基、或者可由烷基或环烷基取代的亚杂芳基，L is a single bond, an alkylene group, an arylene group which may be substituted by an alkyl group or a cycloalkyl group, or a heteroarylene group which may be substituted by an alkyl group or a cycloalkyl group,n为1～3的整数，n is an integer from 1 to 3,当n为2或3时，多个L、多个X、多个R²¹、多个R²²、多个R²³、多个R²⁴、多个R²⁵、多个R²⁶、多个R²⁷、多个R²⁸、多个R²⁹、多个R³⁰分别可相互相同也可不同，When n is 2 or 3, multiple L, multiple X, multiple R²¹ , multiple R²² , multiple R²³ , multiple R²⁴ , multiple R²⁵ , multiple R²⁶ , multiple R²⁷ , multiple R²⁸ , multiple R²⁹ , and multiple R³⁰ may be the same as or different from each other.式(H)所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代，At least one hydrogen in the compound represented by formula (H) may be substituted by a substituted silyl group, a cyano group, a halogen or a deuterium group.式(D)中，In formula (D),A环、B环及C环分别独立地为芳基环或杂芳基环，这些环中的至少一个氢可经取代，Ring A, Ring B and Ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted.X¹及X²分别独立地为＞O、＞C(-R)₂或＞N-R，所述＞N-R的R为可经取代的芳基、可经取代的杂芳基、可经取代的烷基或可经取代的环烷基，另外，所述＞N-R的R可通过连结基或单键而与所述A环、B环及C环中的至少一个环键结，所述＞C(-R)₂的R分别独立地为可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，所述＞C(-R)₂中的两个R可相互键结而形成环，^X1 and^X2 are independently >O, >C(-R)₂ or >NR, wherein R of the >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted or a cycloalkyl group which may be substituted. In addition, R of the >NR may be bonded to at least one of the rings A, B and C via a linking group or a single bond, R of the >C(-R)₂ is independently an aryl group which may be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, and two R of the >C(-R)₂ may be bonded to each other to form a ring,选自由所述单量体或所述多聚体中的芳基环及杂芳基环所组成的群组中的至少一者可由至少一个环烷烃缩合，所述环烷烃中的至少一个氢可经取代，所述环烷烃中的至少一个-CH₂-可由-O-取代，At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the monomer or the multimer may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one -CH₂ - in the cycloalkane may be substituted with -O-,所述单量体或所述多聚体中的B环与C环可经由单键或-O-、-S-、-C(-R)₂-而键结，所述-C(-R)₂-的R为氢、烷基或环烷基，两个R可相互键结而形成环，The B ring and the C ring in the monomer or the polymer may be bonded via a single bond or -O-, -S-, or -C(-R)₂ -, wherein R of -C(-R)₂ - is hydrogen, alkyl, or cycloalkyl, and two Rs may bond to each other to form a ring.所述单量体或所述多聚体中的至少一个氢可由氰基、卤素或氘取代。At least one hydrogen in the monomer or the polymer may be substituted with a cyano group, a halogen, or a deuterium.2.根据权利要求1所述的有机电场发光元件，其中，所述蒽系化合物由下述式(HA)、下述式(HB)、下述式(HC)、下述式(HD)或下述式(HE)表示；2. The organic electroluminescent element according to claim 1, wherein the anthracene compound is represented by the following formula (HA), the following formula (HB), the following formula (HC), the following formula (HD) or the following formula (HE);式(HA)、式(HB)、式(HC)、式(HD)及式(HE)中，In formula (HA), formula (HB), formula (HC), formula (HD) and formula (HE),R¹、R²、R³、R⁶、R⁷、R⁸、R⁹及R¹⁰分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除下述式(BO)所表示的化合物的任一氢而获得的一价基，R¹ , R² , R³ , R⁶ , R⁷ , R⁸ , R⁹ and R¹⁰ are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of a compound represented by the following formula (BO),R²¹～R³⁰分别独立地为氢、碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R²¹～R³⁰中的邻接的基彼此可键结而形成碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢可由碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基取代，R²¹ to R³⁰ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms; adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,其中，R²¹～R³⁰的任意一个构成L，Among them, any one of R²¹ to R³⁰ constitutes L,X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂，所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，X is independently >O, >S, >NR, >C(-R)₂ or >Si(-R)₂ , and R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms,作为X的所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结，所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基，R of the >NR as X may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond, wherein R of -C(-R)₂ - is an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基，L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,式(HA)、式(HB)、式(HC)、式(HD)及式(HE)所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in each of the compounds represented by Formula (HA), Formula (HB), Formula (HC), Formula (HD) and Formula (HE) may be substituted with a substituted silyl group, a cyano group, a halogen or a deuterium.3.根据权利要求2所述的有机电场发光元件，其中，所述蒽系化合物由式(HA)或式(HB)表示。3 . The organic electroluminescent element according to claim 2 , wherein the anthracene compound is represented by formula (HA) or formula (HB).4.根据权利要求3所述的有机电场发光元件，其中，4. The organic electroluminescent element according to claim 3, wherein:R²、R³、R⁶及R⁷均为氢，R² , R³ , R⁶ and R⁷ are all hydrogen,R⁹为碳数6～18的芳基或去除式(BO)所表示的化合物的任一氢而获得的一价基，^R9 is an aryl group having 6 to 18 carbon atoms or a monovalent group obtained by removing any hydrogen atom of the compound represented by the formula (BO),R²¹～R³⁰中，构成L的一个以外的均为氢，Among R²¹ to R³⁰ , all except one constituting L are hydrogen atoms,X分别独立地为＞O、＞S、＞N-R或＞C(-R)₂，所述＞N-R的R为碳数6～16的芳基，所述＞C(-R)₂的R均为甲基，X is independently >O, >S, >NR or >C(-R)₂ , R of the >NR is an aryl group having 6 to 16 carbon atoms, and R of the >C(-R)₂ is a methyl group,L为单键或碳数6～10的亚芳基，L is a single bond or an arylene group having 6 to 10 carbon atoms,式(HA)及式(HB)各自所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in the compound represented by each of Formula (HA) and Formula (HB) may be substituted by a substituted silyl group, a cyano group, a halogen, or a deuterium.5.根据权利要求4所述的有机电场发光元件，其中，所述蒽系化合物由下述结构式的任一者表示；5. The organic electroluminescent element according to claim 4, wherein the anthracene compound is represented by any one of the following structural formulas;式中，D表示氘，Me表示甲基。In the formula, D represents deuterium, and Me represents methyl group.6.根据权利要求2所述的有机电场发光元件，其中，所述蒽系化合物由式(HC)、式(HD)或式(HE)表示。6 . The organic electroluminescent element according to claim 2 , wherein the anthracene compound is represented by formula (HC), formula (HD) or formula (HE).7.根据权利要求6所述的有机电场发光元件，其中，7. The organic electroluminescent element according to claim 6, wherein:R¹、R⁸及R¹⁰均为碳数6～18的芳基，R¹ , R⁸ and R¹⁰ are all aryl groups having 6 to 18 carbon atoms,R²¹～R³⁰中，构成L的一个以外的均为氢，Among R²¹ to R³⁰ , all except one constituting L are hydrogen atoms,X分别独立地为＞O、＞S、＞N-R或＞C(-R)₂，所述＞N-R的R为碳数6～16的芳基，所述＞C(-R)₂的R均为甲基，X is independently >O, >S, >NR or >C(-R)₂ , R of the >NR is an aryl group having 6 to 16 carbon atoms, and R of the >C(-R)₂ is a methyl group,L为单键或碳数6～10的亚芳基，L is a single bond or an arylene group having 6 to 10 carbon atoms,式(HC)、式(HD)及式(HE)各自所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in the compound represented by each of Formula (HC), Formula (HD) and Formula (HE) may be substituted by a substituted silyl group, a cyano group, a halogen or a deuterium.8.根据权利要求7所述的有机电场发光元件，其中，所述蒽系化合物由下述结构式的任一者表示；8. The organic electroluminescent element according to claim 7, wherein the anthracene compound is represented by any one of the following structural formulas;式中，D表示氘。In the formula, D represents deuterium.9.根据权利要求2所述的有机电场发光元件，其中，式(HA)、式(HB)、式(HC)、式(HD)或式(HE)所表示的化合物中的全部的氢由氘取代。9 . The organic electroluminescent element according to claim 2 , wherein all hydrogen atoms in the compound represented by formula (HA), formula (HB), formula (HC), formula (HD) or formula (HE) are substituted with deuterium atoms.10.根据权利要求1至9中任一项所述的有机电场发光元件，其中，所述多环芳香族化合物为作为下述式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的单量体或具有多个式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的部分结构的多聚体的多环芳香族化合物；10. The organic electroluminescent element according to any one of claims 1 to 9, wherein the polycyclic aromatic compound is a monomer represented by the following formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f), or a polymer having a plurality of partial structures represented by formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f);式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)及式(D-f)中，In formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) and formula (D-f),R¹～R¹¹分别独立地为氢、芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、二芳基硼基且其中两个芳基可经由单键或连结基键结、烷基、环烷基、烷氧基、芳氧基或取代硅烷基，它们中的至少一个氢可由芳基、杂芳基、烷基、环烷基或取代硅烷基取代，另外，R¹～R¹¹中的邻接的基彼此可键结并与a环、b环或c环一起形成芳基环或杂芳基环，所形成的环中的至少一个氢可由芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、二芳基硼基且其中两个芳基可经由单键或连结基键结、烷基、环烷基、烷氧基、芳氧基或取代硅烷基取代，它们中的至少一个氢可由芳基、杂芳基、烷基、环烷基或取代硅烷基取代，R¹ to R¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, wherein two aryl groups may be bonded via a single bond or a linking group, alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, at least one hydrogen in them may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl group, in addition, adjacent groups in R¹ to R¹¹ may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, at least one hydrogen in the formed ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, wherein two aryl groups may be bonded via a single bond or a linking group, alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, at least one hydrogen in them may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl group,X_X分别独立地为＞O、＞S、＞N-R或＞C(-R)₂，所述＞N-R的R为可经取代的芳基、可经取代的杂芳基、可经取代的烷基或可经取代的环烷基，另外，所述＞C(-R)₂的R分别独立地为氢、可由烷基或环烷基取代的芳基、可由烷基或环烷基取代的杂芳基、烷基或环烷基，_XX is independently >O, >S, >NR or >C(-R)₂ , R of >NR is aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, and R of >C(-R)₂ is independently hydrogen, aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, alkyl or cycloalkyl,X¹及X²分别独立地为＞O、＞C(-R)₂或＞N-R，所述＞N-R的R为碳数6～12的芳基、碳数2～15的杂芳基、碳数1～6的烷基或碳数3～14的环烷基，所述＞N-R的R中的碳数6～12的芳基及碳数2～15的杂芳基均可由碳数1～6的烷基或碳数3～14的环烷基、或者取代硅烷基取代，所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与a环、b环及c环的至少一个键结，^X1 and^X2 are independently >O, >C(-R)₂ or >NR, wherein R of the >NR is an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, wherein the aryl group having 6 to 12 carbon atoms and the heteroaryl group having 2 to 15 carbon atoms in R of the >NR may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, or a substituted silyl group, and the R of the >NR may be bonded to at least one of the a ring, the b ring and the c ring via -O-, -S-, -C(-R)_2- or a single bond,所述＞C(-R)₂的R分别独立地为碳数6～12的芳基、碳数2～15的杂芳基、碳数1～6的烷基或碳数3～14的环烷基，所述＞C(-R)₂的R中的碳数6～12的芳基及碳数2～15的杂芳基均可由碳数1～6的烷基或碳数3～14的环烷基、或者取代硅烷基取代，所述＞C(-R)₂中的两个R可相互键结而形成环，The R of the >C(-R)₂ is independently an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. The aryl group having 6 to 12 carbon atoms and the heteroaryl group having 2 to 15 carbon atoms in the R of the >C(-R)₂ may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, or a substituted silyl group. The two R of the >C(-R)₂ may be bonded to each other to form a ring.所述单量体或所述多聚体中的a环、b环、c环、所述所形成的环、所述芳基及所述杂芳基的至少一者可由碳数3～24的至少一个环烷烃缩合，所述环烷烃中的至少一个氢可由碳数6～30的芳基、碳数2～30的杂芳基、碳数1～24的烷基或碳数3～24的环烷基取代，所述环烷烃中的至少一个-CH₂-可由-O-取代，At least one of the a ring, b ring, c ring, the formed ring, the aryl group and the heteroaryl group in the monomer or the multimer may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, at least one -CH₂ - in the cycloalkane may be substituted with -O-,所述单量体或所述多聚体中的至少一个氢可由氰基、卤素或氘取代，At least one hydrogen in the monomer or the polymer may be substituted by cyano, halogen or deuterium,在多聚体的情况下，为具有2个或3个式(D-a)、式(D-b)、式(D-c)、式(D-d)、式(D-e)或式(D-f)所表示的部分结构的二聚体或三聚体。In the case of a multimer, it is a dimer or trimer having 2 or 3 partial structures represented by formula (D-a), formula (D-b), formula (D-c), formula (D-d), formula (D-e) or formula (D-f).11.根据权利要求10所述的有机电场发光元件，其中，所述多环芳香族化合物为作为式(D-a)所表示的单量体或具有多个式(D-a)所表示的部分结构的多聚体的多环芳香族化合物。11. The organic electroluminescent element according to claim 10, wherein the polycyclic aromatic compound is a monomer represented by formula (D-a) or a polymer having a plurality of partial structures represented by formula (D-a).12.根据权利要求11所述的有机电场发光元件，其中，所述多环芳香族化合物由下述结构式的任一者表示；12. The organic electroluminescent element according to claim 11, wherein the polycyclic aromatic compound is represented by any one of the following structural formulas:式中，D表示氘，Me表示甲基，tBu表示叔丁基。In the formula, D represents deuterium, Me represents methyl group, and tBu represents tert-butyl group.13.根据权利要求10所述的有机电场发光元件，其中，所述多环芳香族化合物为作为式(D-b)所表示的单量体或具有多个式(D-b)所表示的部分结构的多聚体的多环芳香族化合物。13. The organic electroluminescent element according to claim 10, wherein the polycyclic aromatic compound is a monomer represented by formula (D-b) or a polymer having a plurality of partial structures represented by formula (D-b).14.根据权利要求13所述的有机电场发光元件，其中，所述多环芳香族化合物由下述结构式的任一者表示；14. The organic electroluminescent element according to claim 13, wherein the polycyclic aromatic compound is represented by any one of the following structural formulas:式中，Me表示甲基，tBu表示叔丁基。In the formula, Me represents a methyl group, and tBu represents a tert-butyl group.15.根据权利要求1至9中任一项所述的有机电场发光元件，其具有配置于所述阴极与所述发光层之间的电子传输层及电子注入层的至少一层，所述电子传输层及电子注入层的至少一层含有选自由硼烷衍生物、吡啶衍生物、荧蒽衍生物、BO系衍生物、蒽衍生物、苯并芴衍生物、氧化膦衍生物、嘧啶衍生物、芳基腈衍生物、三嗪衍生物、苯并咪唑衍生物、菲咯啉衍生物、羟基喹啉系金属络合物、噻唑衍生物、苯并噻唑衍生物、噻咯衍生物及唑啉衍生物所组成的群组中的至少一种。15. An organic electric field light-emitting element according to any one of claims 1 to 9, which has at least one layer of an electron transport layer and an electron injection layer arranged between the cathode and the light-emitting layer, and at least one layer of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aromatic nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and oxazoline derivatives.16.根据权利要求15所述的有机电场发光元件，其中，所述电子传输层及电子注入层的至少一层还含有选自由碱金属、碱土金属、稀土金属、碱金属的氧化物、碱金属的卤化物、碱土金属的氧化物、碱土金属的卤化物、稀土金属的氧化物、稀土金属的卤化物、碱金属的有机络合物、碱土金属的有机络合物及稀土金属的有机络合物所组成的群组中的至少一种。16. The organic electroluminescent element according to claim 15, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes.17.一种显示装置，包括如权利要求1至16中任一项所述的有机电场发光元件。17 . A display device comprising the organic electroluminescent element according to claim 1 .18.一种照明装置，包括如权利要求1至16中任一项所述的有机电场发光元件。18. A lighting device comprising the organic electroluminescent element according to any one of claims 1 to 16.19.一种化合物，其由下述式(HA')或下述式(HB')表示；19. A compound represented by the following formula (HA') or the following formula (HB');式(HA')及式(HB')中，In formula (HA') and formula (HB'),R²、R³、R⁶、R⁷及R⁹分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除下述式(BO)所表示的化合物的任一氢而获得的一价基，R² , R³ , R⁶ , R⁷ and R⁹ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of a compound represented by the following formula (BO),R²¹～R³⁰分别独立地为氢、碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R²¹～R³⁰中的邻接的基彼此可键结而形成碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢可由碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基取代，R²¹ to R³⁰ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms; adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,其中，R²¹～R³⁰的任意一个构成L，Among them, any one of R²¹ to R³⁰ constitutes L,R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R is each independently an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结，所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基，R may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond, wherein R of -C(-R)₂ - is an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基，L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,式(HA')及式(HB')所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in each of the compounds represented by Formula (HA') and Formula (HB') may be substituted with a substituted silyl group, a cyano group, a halogen, or a deuterium.20.根据权利要求19所述的化合物，其中，R²、R³、R⁶、R⁷均为氢，R⁹为未经取代的碳数6～30的芳基或去除式(BO)所表示的化合物的任一氢而获得的一价基，且为未经取代的碳数6～12的芳基或去除式(BO)所表示的化合物的任一氢而获得的一价基，R为未经取代的碳数6～16的芳基，L均为单键。20. The compound according to claim 19, wherein^R2 ,^R3 ,^R6 , and^R7 are all hydrogen,^R9 is an unsubstituted aryl group having 6 to 30 carbon atoms or a monovalent group obtained by removing any hydrogen atoms of the compound represented by formula (BO), and is an unsubstituted aryl group having 6 to 12 carbon atoms or a monovalent group obtained by removing any hydrogen atoms of the compound represented by formula (BO), R is an unsubstituted aryl group having 6 to 16 carbon atoms, and L is a single bond.21.一种化合物，其由下述式(HC')或下述式(HE')表示；21. A compound represented by the following formula (HC') or the following formula (HE');式(HC')及式(HE')中，In formula (HC') and formula (HE'),R¹、R²、R³、R⁶、R⁷及R⁸分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除下述式(BO)所表示的化合物的任一氢而获得的一价基，R¹ , R² , R³ , R⁶ , R⁷ and R⁸ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of a compound represented by the following formula (BO),R²¹～R³⁰分别独立地为氢、碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，R²¹～R³⁰中的邻接的基彼此可键结而形成碳数6～10的芳基环或碳数2～10的杂芳基环，所形成的环中的至少一个氢可由碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基取代，R²¹ to R³⁰ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms; adjacent groups among R²¹ to R³⁰ may be bonded to each other to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,其中，R²¹～R³⁰的任意一个构成L，Among them, any one of R²¹ to R³⁰ constitutes L,X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂，所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，X is independently >O, >S, >NR, >C(-R)₂ or >Si(-R)₂ , and R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms,作为X的所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结，所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基，R of the >NR as X may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond, wherein R of -C(-R)₂ - is an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基，L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,式(HC')及式(HE')所表示的化合物各自中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in each of the compounds represented by Formula (HC') and Formula (HE') may be substituted with a substituted silyl group, a cyano group, a halogen, or a deuterium.22.根据权利要求21所述的化合物，其中，R²、R³、R⁶、R⁷均为氢，R¹及R⁸分别独立地为未经取代的碳数6～30的芳基，L均为单键。22. The compound according to claim 21, wherein^R2 ,^R3 ,^R6 , and^R7 are all hydrogen,^R1 and^R8 are each independently an unsubstituted aryl group having 6 to 30 carbon atoms, and L is a single bond.23.一种化合物，其由下述式(HD')表示；23. A compound represented by the following formula (HD');式(HD')中，In the formula (HD'),R²、R³、R⁶、R⁷及R¹⁰分别独立地为氢、碳数6～30的芳基、碳数2～15的杂芳基、碳数1～12的烷基、碳数3～16的环烷基、或去除下述式(BO)所表示的化合物的任一氢而获得的一价基，R² , R³ , R⁶ , R⁷ and R¹⁰ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or a monovalent group obtained by removing any hydrogen atom of a compound represented by the following formula (BO),R²¹～R³⁰中，任意一个为未经取代的碳数6～16的芳基，R²¹～R³⁰的任意一个构成L，R²¹～R³⁰的其他的任意一个为未经取代的碳数6～16的芳基，其他为氢，Any one of R²¹ to R³⁰ is an unsubstituted aryl group having 6 to 16 carbon atoms, any one of R²¹ to R³⁰ constitutes L, any other one of R²¹ to R³⁰ is an unsubstituted aryl group having 6 to 16 carbon atoms, and the others are hydrogen atoms,X分别独立地为＞O、＞S、＞N-R、＞C(-R)₂或＞Si(-R)₂，所述＞N-R、＞C(-R)₂及＞Si(-R)₂的R分别独立地为碳数6～16的芳基、碳数2～15的杂芳基、碳数1～12的烷基或碳数3～16的环烷基，X is independently >O, >S, >NR, >C(-R)₂ or >Si(-R)₂ , and R of >NR, >C(-R)₂ and >Si(-R)₂ is independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms,作为X的所述＞N-R的R可通过-O-、-S-、-C(-R)₂-或单键而与R²¹或R³⁰键结，所述-C(-R)₂-的R为碳数1～12的烷基或碳数3～16的环烷基，R of the >NR as X may be bonded to R²¹ or R³⁰ via -O-, -S-, -C(-R)₂ - or a single bond, wherein R of -C(-R)₂ - is an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,L分别独立地为单键、碳数1～6的亚烷基、可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数6～16的亚芳基、或者可由碳数1～5的烷基或碳数5～10的环烷基取代的碳数2～15的亚杂芳基，L is each independently a single bond, an alkylene group having 1 to 6 carbon atoms, an arylene group having 6 to 16 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms which may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,式(HD')所表示的化合物中的至少一个氢可由取代硅烷基、氰基、卤素或氘取代。At least one hydrogen in the compound represented by the formula (HD') may be substituted by a substituted silyl group, a cyano group, a halogen or a deuterium.24.根据权利要求23所述的化合物，其中，R²、R³、R⁶、R⁷均为氢，R¹⁰为未经取代的碳数6～30的芳基。The compound according to claim 23, wherein R² , R³ , R⁶ and R⁷ are all hydrogen, and R¹⁰ is an unsubstituted aryl group having 6 to 30 carbon atoms.