CN111848587A - Partial triazine derivative, electronic device and application - Google Patents
Partial triazine derivative, electronic device and applicationDownload PDFInfo
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Abstract
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and relates to a partial triazine derivative and an electronic device containing the partial triazine derivative. More particularly, the present invention relates to a partial triazine derivative suitable for electronic devices, particularly organic electroluminescent devices, organic field effect transistors, and organic solar cells, and an electronic device using the partial triazine derivative.
Background
The organic electroluminescent device has a series of advantages of self-luminescence, low-voltage driving, full curing, wide viewing angle, simple composition and process and the like, and compared with a liquid crystal display, the organic electroluminescent device does not need a backlight source. Therefore, the organic electroluminescent device has wide application prospect.
Organic electroluminescent devices generally comprise an anode, a metal cathode and an organic layer sandwiched therebetween. The organic layer mainly comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.
The research on the improvement of the performance of the organic electroluminescent device includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the organic electroluminescent device, not only the innovation of the device structure and the manufacturing process but also the continuous research and innovation of the photoelectric functional material are needed to create the organic electroluminescent functional material with higher performance.
Photoelectric functional materials applied to organic electroluminescent devices can be divided into two major types from the aspect of application, namely charge injection transport materials and luminescent materials, further, the charge injection transport materials can be divided into electron injection transport materials and hole injection transport materials, and the luminescent materials can be divided into main luminescent materials and doping materials. In order to fabricate a high-performance organic electroluminescent device, various organic functional materials are required to have good photoelectric properties, such as good carrier mobility and high glass transition temperature as charge transport materials, and the material used as a light emitting layer is required to have a high triplet state energy level and high stability.
At present, research on organic electroluminescent materials has been widely conducted in academia and industry, and a large number of organic electroluminescent materials with excellent performance have been developed. In view of the above, the future direction of organic electroluminescent devices is to develop high efficiency, long lifetime, low cost white light devices and full color display devices, but the industrialization of the technology still faces many key problems. Therefore, designing and searching a stable and efficient compound as a novel material of an organic electroluminescent device to overcome the defects of the organic electroluminescent device in the practical application process is a key point in the research work of the organic electroluminescent device material and the future research and development trend.
Disclosure of Invention
The invention aims to provide a metatriazine derivative. The metatriazine derivative has high thermal stability, good transmission performance and simple preparation method, and an organic light-emitting device prepared from the metatriazine derivative has the advantages of high light-emitting efficiency, long service life and low driving voltage, and is an organic electroluminescent material with excellent performance.
It is another object of the present invention to provide an electronic device using the partial triazine derivative, which has advantages of high efficiency, high durability and long life.
The metatriazine compound has a special biphenyl structure, has higher thermal stability, chemical stability and carrier transport property, and more importantly has proper singlet state, triplet state and molecular orbital energy level. Therefore, the organic electroluminescent material is introduced into molecules with electroluminescent characteristics, so that the stability and the luminous efficiency of a device are improved, and the driving voltage of the device is reduced.
The invention is characterized in that the unsym-triazine derivative has good film forming property and thermal stability by introducing a rigidity structure of the unsym-triazine, can be used for preparing electronic devices such as organic electroluminescent devices, organic field effect transistors and organic solar cells, especially used as a constituent material of a hole injection layer, a hole transmission layer, a luminescent layer, an electron blocking layer, a hole blocking layer or an electron transmission layer in the organic electroluminescent devices, can show the advantages of high luminous efficiency, long service life and low driving voltage, and is obviously superior to the existing organic electroluminescent devices.
In addition, the preparation method of the unsym-triazine derivative is simple, raw materials are easy to obtain, and the industrial development requirement can be met.
The invention has good application effect in organic electroluminescent devices, organic field effect transistors, organic solar cells and other electronic devices, and has wide industrialization prospect.
The metatriazine derivative has high electron injection and moving speed. Therefore, with the organic electroluminescent device having an electron injection layer and/or an electron transport layer prepared using the partial triazine derivative of the present invention, the electron transport efficiency from the electron transport layer to the light emitting layer is improved, thereby improving the light emitting efficiency. And, the driving voltage is reduced, thereby enhancing durability of the resulting organic electroluminescent device.
The metatriazine derivative has excellent hole blocking capacity and excellent electron transport performance, and is stable in a thin film state. Therefore, the organic electroluminescent device having a hole blocking layer prepared using the partial triazine derivative of the present invention has high luminous efficiency, a reduced driving voltage, and improved current resistance, so that the maximum luminous brightness of the organic electroluminescent device is increased.
The partial triazine derivative can be used as a constituent material of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, a hole blocking layer or an electron transport layer of an organic electroluminescent device. With the organic electroluminescent device of the present invention, excitons generated in the light emitting layer can be confined, and the possibility of recombination of holes and electrons can be further increased to obtain high luminous efficiency. Further, the driving voltage is relatively low, and thus high durability can be achieved.
Drawings
FIG. 1 shows a fluorescence spectrum (PL) of example 1 (Compound 1-1) of the present invention in a dichloromethane solution.
Fig. 2 is an electroluminescence spectrum of example 5 (organic electroluminescence device 2) of the present invention.
FIG. 3 is a view showing the structures of organic electroluminescent devices of examples 4 to 6 of the present invention and organic electroluminescent devices of comparative examples 1 to 2.
Description of the reference numerals
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-electron barrier layer, 6-luminescent layer, 7-hole barrier layer, 8-electron transport layer, 9-electron injection layer and 10-cathode.
Detailed Description
The present invention will be described in detail below with reference to specific embodiments. However, the present invention is not limited to the following embodiments.
The partial triazine derivative of the present invention is a novel compound having a partial triazine structure, and is represented by the following general formula (1).
Specifically, the partial triazine derivative has the following general formula (I) or (II):
in the above general formulae (1), (I) and (II),
L1and L2Each independently represents one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms;
m and n are each independently an integer of 0 to 5, and m and n are not 0 at the same time;
A1and A2Each independently represents Ar1、Ar2、
Ar1～Ar4Each independently represents optionally substituted one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms;
z represents CR1Or N;
R1represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、N(R2)2、OR2、SR2、C(＝O)R2、P(＝O)R2、Si(R2)3Substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or substituted or unsubstituted aryl group havingOne or more of aromatic heterocyclic groups of 5 to 40 carbon atoms;
R2represents one or more of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
(L1And L2)
L1And L2Each independently represents one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms.
In the present invention, the hetero atom in the aromatic heterocyclic group having 5 to 18 carbon atoms is preferably selected from N, O and/or S. In the present invention, the number of hetero atoms may be 1 to 5. An aromatic hydrocarbon group or aromatic heterocyclic group in the sense of the present invention means a system which does not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be interrupted by non-aromatic units (preferably less than 10% of non-hydrogen atoms), which may be, for example, carbon atoms, nitrogen atoms, oxygen atoms or carbonyl groups. For example, systems of 9, 9' -spirobifluorenes, 9, 9-diarylfluorenes, triarylamines, diaryl ethers, etc., as well as systems in which two or more aryl groups are interrupted, for example by linear or cyclic alkyl groups or by silyl groups, are also intended to be considered aromatic hydrocarbon groups in the sense of the present invention. Furthermore, systems in which two or more aryl or heteroaryl groups are bonded directly to one another, such as biphenyl, terphenyl or quaterphenyl, are likewise intended to be regarded as aromatic hydrocarbon groups or aromatic heterocyclic groups.
From L1And L2The aromatic hydrocarbon group having 6 to 18 carbon atoms or the aromatic heterocyclic group having 5 to 18 carbon atoms represented may be exemplified by: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, perylenyl, fluoranthenyl, benzofluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenylPentabiphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, cis-or trans-monobenzoindenofluorenyl, cis-or trans-dibenzoindenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolocarbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, phenanthridinyl, and the like, Benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazenanthranyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazpyrenyl, 1, 8-diazpyrenyl, 4, 5-diazapynyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescentrynyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, and the like.
In the present invention, preferably, L1And L2Each independently represents a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 5 to 12 carbon atoms. More preferably, L1And L2Each independentlyRepresents one or more of a single bond, a carbonyl group, a phenyl group, a triazinyl group or a biphenyl group.
From L1And L2The aromatic hydrocarbon group having 6 to 18 carbon atoms or the aromatic heterocyclic group having 5 to 18 carbon atoms represented may be unsubstituted, but may also have a substituent. The substituents may be exemplified by the following: a deuterium atom; a cyano group; a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; an alkyl group having 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, or a n-hexyl group; alkoxy having 1 to 6 carbon atoms such as methoxy, ethoxy or propoxy; alkenyl, such as vinyl or allyl; aryloxy groups such as phenoxy or tolyloxy; arylalkoxy, such as benzyloxy or phenethyloxy; aromatic hydrocarbon radicals or condensed polycyclic aromatic radicals, e.g. phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthryl, benzo [9,10 ] benzo]Phenanthryl or spirobifluorenyl; an aromatic heterocyclic group such as pyridyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuryl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalyl, benzimidazolyl, pyrazolyl, dibenzofuryl, dibenzothienyl, azafluorenyl, diazafluorenyl, carbolinyl, azaspirobifluorenyl or diazaspiro-bifluorenyl; arylethenyl, such as styryl or naphthylethenyl; acyl groups such as acetyl or benzoyl and the like.
The alkyl group having 1 to 6 carbon atoms and the alkoxy group having 1 to 6 carbon atoms may be linear or branched. Any of the above substituents may be further substituted with the above exemplary substituents. The above substituents may be present independently of each other, but may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.
(A1And A2)
A1And A2Each independently represents Ar1、Ar2、
(Ar1To Ar4)
Ar1～Ar4Each independently represents optionally substituted one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms.
From Ar1～Ar4The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented may be exemplified by: phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, perylenyl, fluoranthenyl, benzofluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, biphenylyl, terphenyl, quaterphenyl, pentabiphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, hydropyranyl, cis-or trans-indenofluorenyl, cis-or trans-monobenzindenofluorenyl, cis-or trans-dibenzoindenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridecyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, benzothienyl, benzothiophenocarbazolyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolocarbazolyl, indenocarbazolyl, pyridyl, bipyridyl, perylenyl, pyranthrylyl, benzopyrenyl, pentacenyl, benzopyrenyl, terphenyl, Terpyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxaloimidazolyl, oxazolyl, benzoxazolyl, benzooxadiazolyl, naphthooxazolyl, anthraoxazolyl, phenanthrooxazolyl, isoxazolyl, thiazolyl, isothiazolyl, benzothiazolyl, benzothiadiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, quinazolinyl, azaazaspiroxazinyl, benzoxazolyl, phenanthroidinyl, isoxazolyl, isothiazolyl, benzimidazolyl, benzoxazolyl, and phenanthroimidazolylFluorenyl, diazanthryl, diazpyrenyl, tetraazaperylenyl, diazaphthyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluoresceinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, triazolyl, benzotriazolyl, oxadiazolyl, thiadiazolyl, triazinyl, tetrazolyl, tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, pyridopyrrolyl, pyridotriazolyl, xanthenyl, benzofurocarbazolyl, benzofluorenocarbazyl, N-phenylcarbazolyl, diphenyl-benzimidazolyl, diphenyl-oxadiazolyl, diphenyl-boryl, triphenylphophatyloxy, diphenylphosphinyloxy, triphenylsilyl, tetraphenylsilyl, and the like.
In the present invention, preferably, Ar1～Ar4Each independently selected from the following groups:
wherein the dotted line represents and L1、L2Or an N-bonded bond;
R1has the meaning as defined for the general formula (1).
From Ar1～Ar4The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented may be unsubstituted, but may also have a substituent. Preferably, from Ar1～Ar4The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented by1Substituted, aromatic hydrocarbon radicals having 5 to 30 carbon atoms or substituted by one or more R1A substituted aromatic heterocyclic group having 5 to 30 carbon atoms.
(R1)
R1Represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、N(R2)、OR2、SR2、C(＝O)R2、P(＝O)R2、Si(R2)3One or more of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms.
From R1The alkyl group having 1 to 20 carbon atoms represented may be exemplified by: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like. The alkyl group having 1 to 20 carbon atoms may be linear, branched or cyclic.
From R1The alkyl group having 1 to 20 carbon atoms represented may be unsubstituted, but may also have a substituent. Preferably, from R1Alkyl having 1 to 20 carbon atoms represented by one or more of the following R2And (4) substitution. In addition, one or more non-adjacent CH in the alkyl group2The group can be represented by R2C＝CR2、C≡C、Si(R2)3、C＝O、C＝NR2、P(＝O)R2、SO、SO2、NR2O, S or CONR2And wherein one or more hydrogen atoms may be replaced with deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, nitro group.
From R1The alkenyl group having 2 to 20 carbon atoms represented may be exemplified by: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, 2-ethylhexenyl, allyl, cyclohexenyl and the like. The alkenyl group having 2 to 20 carbon atoms may be linear, branched or cyclic.
From R1The alkenyl group having 2 to 20 carbon atoms represented may be unsubstituted or may have a substituent. The substituents can be exemplified by the group consisting of R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents.
From R1The alkynyl group having 2 to 20 carbon atoms represented may be exemplified by: ethynyl, isopropynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl and the like.
From R1The alkynyl group having 2 to 20 carbon atoms represented may be unsubstituted or may have a substituent. The substituents can be exemplified by the group consisting of R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents.
From R1The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms represented by the above formula may be exemplified by the group consisting of Ar1～Ar4The aromatic hydrocarbon group having 6 to 30 carbon atoms or the aromatic heterocyclic group having 5 to 30 carbon atoms represented by the above formula represent the same groups.
From R1Having 6 to 40 carbon atoms or having 5 to 40The aromatic heterocyclic group of carbon atoms may be unsubstituted or may have a substituent. The substituents can be exemplified by the group consisting of R1The alkyl group having 1 to 20 carbon atoms represented by (b) may have the same substituent as that represented by the substituent(s). The substituents may take the same pattern as that of the exemplary substituents. In addition, two adjacent R1Substituents or two adjacent R2The substituents optionally may form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more R2Substitution; where two or more substituents R1May be connected to each other and may form a ring.
Preferably represented by R1The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms represented by (a) may be exemplified by: phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzothienocarbazolyl, benzofurocarbazolyl, benzofluorenocarbazolyl, benzanthracenyl, benzophenanthryl, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-oxadiazolyl, diphenyl boron, triphenyl phosphoxy, diphenyl phosphoxy, triphenyl silicon group, tetraphenyl silicon group, and the like. The aromatic hydrocarbon group having 6 to 40 carbon atoms or the aromatic heterocyclic group having 5 to 40 carbon atoms may be substituted with one or more R2And (4) substitution.
(R2)
R2Represents one or more of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
From R2The alkyl group having 1 to 20 carbon atoms represented by R can be enumerated by1The alkyl groups represented by the formulae having 1 to 20 carbon atoms represent the same groups.
From R2Having 6 to 3 ofAn aromatic hydrocarbon group of 0 carbon atom or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms can be exemplified by the aforementioned R1The same groups as those shown for the aromatic hydrocarbon group having 6 to 30 carbon atoms or the substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
From R2The alkyl group having 1 to 20 carbon atoms, the aromatic hydrocarbon group having 6 to 30 carbon atoms, or the substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms represented may be unsubstituted, or may also have a substituent. The substituents may be exemplified by: a deuterium atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; cyano, and the like.
(m and n)
m and n are each independently an integer of 0 to 5, and m and n are not 0 at the same time;
(Z)
z represents CR1Or N.
R1Have the meaning as defined above.
(production method)
The partial triazine derivative of the present invention can be produced, for example, by the following method:
the obtained compound can be purified by, for example, purification by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, or the like, recrystallization or crystallization using a solvent, sublimation purification, or the like. Identification of compounds can be carried out by mass spectrometry, elemental analysis.
Specific examples of preferred compounds among the partial triazine derivatives of the present invention are shown below, but the present invention is by no means limited to these compounds.
(electronic devices)
Various electronic devices containing the present invention's metatriazine derivatives can be produced using the present invention's metatriazine derivatives for producing organic materials that can be configured, in particular, in the form of layers. In particular, the partial triazine derivatives can be used for organic electroluminescent devices, organic solar cells, organic diodes, and particularly organic field effect transistors. Particularly in the case of an organic electroluminescent device or a solar cell, the assembly may have a plug structure (the device has one or more p-doped hole transport layers and/or one or more n-doped electron transport layers) or an inverted structure (from the light emitting layer, the upper electrode and the hole transport layer are located on the same side while the substrate is on the opposite side), without being limited to these structures. The injection layer, transport layer, light-emitting layer, barrier layer, etc. can be produced, for example, by forming a layer comprising or consisting of the partial triazine derivative according to the invention between the electrodes. However, the use of the partial triazine derivative according to the present invention is not limited to the above-described exemplary embodiments.
(organic electroluminescent device)
The organic electroluminescent device of the present invention comprises: the light-emitting element includes a first electrode, a second electrode provided so as to face the first electrode, and at least one organic layer located between the first electrode and the second electrode, wherein the at least one organic layer includes the partial triazine derivative of the present invention.
Fig. 3 is a view showing the configuration of an organic electroluminescent device of the present invention. As shown in fig. 3, in the organic electroluminescent device of the present invention, for example, ananode 2, ahole injection layer 3, ahole transport layer 4, anelectron blocking layer 5, alight emitting layer 6, ahole blocking layer 7, anelectron transport layer 8, anelectron injection layer 9, and acathode 10 are sequentially disposed on asubstrate 1.
The organic electroluminescent device of the present invention is not limited to such a structure, and for example, some organic layers may be omitted in the multi-layer structure. For example, it may be a configuration in which thehole injection layer 3 between theanode 2 and thehole transport layer 4, thehole blocking layer 7 between the light emittinglayer 6 and theelectron transport layer 8, and theelectron injection layer 9 between theelectron transport layer 8 and thecathode 10 are omitted, and theanode 2, thehole transport layer 4, thelight emitting layer 6, theelectron transport layer 8, and thecathode 10 are sequentially provided on thesubstrate 1.
The organic electroluminescent device according to the present invention can be manufactured by materials and methods known in the art, except that the above organic layer contains the compound represented by the above general formula (1). In addition, in the case where the organic electroluminescent device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic electroluminescent device according to the present invention may be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. At this time, the following can be made: an anode is formed by depositing metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and a substance which can be used as a cathode is deposited on the organic layer. However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode of the organic electroluminescent device of the present invention may be made of a known electrode material. For example, an electrode material having a large work function, such as a metal of vanadium, chromium, copper, zinc, gold, or an alloy thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; such as ZnO, Al or SNO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyanilineAnd the like. Among these, ITO is preferable.
As the hole injection layer of the organic electroluminescent device of the present invention, a known material having a hole injection property can be used. For example: porphyrin compounds represented by copper phthalocyanine, naphthalenediamine derivatives, star-shaped triphenylamine derivatives, triphenylamine trimers such as arylamine compounds having a structure in which 3 or more triphenylamine structures are connected by a single bond or a divalent group containing no heteroatom in the molecule, tetramers, receptor-type heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, an ink jet method, or the like.
As the hole transport layer of the organic electroluminescent device of the present invention, it is preferable to use a compound containing the present invention. In addition, other known materials having a hole-transporting property can be used. For example: a compound containing a m-carbazolylphenyl group; benzidine derivatives such as N, N ' -diphenyl-N, N ' -di (m-tolyl) benzidine (TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N ' -tetrakisbiphenylylbenzidine, and the like; 1, 1-bis [ (di-4-tolylamino) phenyl ] cyclohexane (TAPC); various triphenylamine trimers and tetramers; 9,9 ', 9 "-triphenyl-9H, 9' H, 9" H-3,3 ': 6', 3 "-tricarbazole (Tris-PCz), and the like. These may be used as a single layer formed by film formation alone or by mixing with other materials to form a film, or may be used as a laminated structure of layers formed by film formation alone, a laminated structure of layers formed by mixing into a film, or a laminated structure of layers formed by film formation alone and layers formed by mixing into a film. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, an ink jet method, or the like.
In addition, in the hole injection layer or the hole transport layer, a material obtained by further P-doping tribromoaniline antimony hexachloride, an axial olefin derivative, or the like to a material generally used in the layer, a polymer compound having a structure of a benzidine derivative such as TPD in a partial structure thereof, or the like may be used.
As the electron blocking layer of the organic electroluminescent device of the present invention, a compound containing the triazine derivative of the present invention is preferably used. In addition, other known compounds having an electron blocking effect may be used. For example, the following: carbazole derivatives such as 4,4', 4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), 9-bis [4- (carbazol-9-yl) phenyl ] fluorene, 1, 3-bis (carbazol-9-yl) benzene (mCP), and 2, 2-bis (4-carbazol-9-ylphenyl) adamantane (Ad-Cz); a compound having a triphenylsilyl and triarylamine structure represented by 9- [4- (carbazol-9-yl) phenyl ] -9- [4- (triphenylsilyl) phenyl ] -9H-fluorene; and compounds having an electron-blocking effect, such as monoamine compounds having a high electron-blocking property and various triphenylamine dimers. These may be used as a single layer formed by film formation alone or by mixing with other materials to form a film, or may be used as a laminated structure of layers formed by film formation alone, a laminated structure of layers mixed to form a film, or a laminated structure of layers formed by film formation alone and layers mixed to form a film. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, an ink jet method, or the like.
As the light-emitting layer of the organic electroluminescent device of the present invention, a light-emitting layer containing the present invention is preferably used. In addition to this, Alq can also be used3Various metal complexes such as metal complexes of a first hydroxyquinoline derivative, compounds having a pyrimidine ring structure, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, and the like.
The light emitting layer may be composed of a host material and a dopant material. As the host material, it is preferable to use a material containing the present invention. In addition to these, mCBP, mCP, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, heterocyclic compounds having a partial structure in which an indole ring is a condensed ring, and the like can be used.
As the doping material, it is preferable to use a compound containing the present invention. In addition to these, aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like can be used. Examples thereof include pyrene derivatives, anthracene derivatives, quinacridones, coumarins, rubrenes, perylenes and their derivatives, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, spirobifluorene derivatives, and the like. These may be used as a single layer formed by film formation alone or by mixing with other materials to form a film, or may be used as a laminated structure of layers formed by film formation alone, a laminated structure of layers mixed to form a film, or a laminated structure of layers formed by film formation alone and layers mixed to form a film. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, an ink jet method, or the like.
As the hole blocking layer of the organic electroluminescent device of the present invention, a hole blocking layer containing the present invention is preferably used. In addition, the hole-blocking layer may be formed using another compound having a hole-blocking property. For example, a phenanthroline derivative such as 2,4, 6-tris (3-phenyl) -1,3, 5-triazine (T2T), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), Bathocuproine (BCP), a metal complex of a quinolyl derivative such as aluminum (III) bis (2-methyl-8-hydroxyquinoline) -4-phenylphenate (BAlq), and a compound having a hole-blocking effect such as various rare earth complexes, oxazole derivatives, triazole derivatives, and triazine derivatives can be used. These may be used as a single layer formed by film formation alone or by mixing with other materials to form a film, or may be used as a laminated structure of layers formed by film formation alone, a laminated structure of layers formed by mixing into a film, or a laminated structure of layers formed by film formation alone and layers formed by mixing into a film. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, an ink jet method, or the like.
The above-described material having a hole-blocking property can also be used for formation of an electron transport layer described below. That is, by using the known material having a hole-blocking property, a layer which serves as both a hole-blocking layer and an electron-transporting layer can be formed.
As the electron transport layer of the organic electroluminescent device of the present invention, it is preferable to use a compound containing the present invention. In addition, the compound may be formed using other compounds having an electron-transporting property. For example, Alq can be used3And (B) Hydroxyquine including BALqMetal complexes of quinoline derivatives; various metal complexes; a triazole derivative; a triazine derivative; an oxadiazole derivative; a pyridine derivative; bis (10-hydroxybenzo [ H ]]Quinoline) beryllium (Be (bq)2) (ii) a Such as 2- [4- (9, 10-dinaphthalen-2-anthracen-2-yl) phenyl]Benzimidazole derivatives such as-1-phenyl-1H-benzimidazole (ZADN); a thiadiazole derivative; an anthracene derivative; a carbodiimide derivative; quinoxaline derivatives; pyridoindole derivatives; phenanthroline derivatives; silole derivatives and the like. These may be used as a single layer formed by film formation alone or by mixing with other materials to form a film, or may be used as a laminated structure of layers formed by film formation alone, a laminated structure of layers formed by mixing into a film, or a laminated structure of layers formed by film formation alone and layers formed by mixing into a film. These materials can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method, an ink jet method, or the like.
As the electron injection layer of the organic electroluminescent device of the present invention, a material known per se can be used. For example, alkali metal salts such as lithium fluoride and cesium fluoride; alkaline earth metal salts such as magnesium fluoride; metal complexes of quinolinol derivatives such as lithium quinolinol; and metal oxides such as alumina.
In the electron injection layer or the electron transport layer, a material obtained by further N-doping a metal such as cesium, a triarylphosphine oxide derivative, or the like can be used as a material generally used for the layer.
As the cathode of the organic electroluminescent device of the present invention, an electrode material having a low work function such as aluminum, magnesium, or an alloy having a low work function such as magnesium-silver alloy, magnesium-indium alloy, aluminum-magnesium alloy is preferably used as the electrode material.
As the substrate of the present invention, a substrate in a conventional organic light emitting device, such as glass or plastic, can be used. In the present invention, a glass substrate is selected.
Examples
The production of the compound represented by the above general formula (1) and the organic electroluminescent device comprising the same is specifically described in the following examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
Example 1: synthesis of Compound 1-1
(Synthesis of intermediate M1)
The synthetic route for intermediate M1 is shown below:
in a 250mL single-neck flask, p-bromobenzimidate hydrazide hydrochloride (5.0g, 20mmol), 4-bromophenyl glyoxal hydrate (4.6g, 20mmol) and 120mL of anhydrous ethanol were sequentially added, and the reaction was stirred under reflux for 12 hours. After the reaction, the solid was collected by suction filtration and washed with a small amount of anhydrous ethanol. The crude product was further purified by column chromatography (petroleum ether: dichloromethane ═ 3: 1 (V/V)). The solvent was evaporated and dried to give 5.1g of a pale yellow solid in 65% yield. Ms (ei): m/z: 390.88[ M ]+]。Anal.calcdfor C15H9Br2N3(％)：C 46.07，H 2.32，N 10.75；found：C 46.03，H 2.36，N 10.74。
(Synthesis of Compound 1-1)
The synthetic route for compound 1-1 is shown below:
under nitrogen protection, intermediate M1(2.0g, 5mmol), carbazole (1.8g, 11mmol), palladium acetate (22.4mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (1.9g, 20mmol) and 120mL of toluene were added in this order to a 250mL Schlenk flask, and the reaction was stirred under reflux for 12 hours. After completion of the reaction, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane and 50mL of water, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, the organic layers were combined, the solvent was distilled off, and the residue was separated by column chromatography (petroleum ether: dichloromethane ═ 3: 1 (V/V)). The solvent was evaporated and dried to give 2.2g of a yellow solid in 78% yield. Ms (ei): m/z: 563.28[ M ]+]。Anal.calcd for C39H25N5(％)：C83.10，H 4.47，N 1242; found: c83.06, H4.50, N12.39. The fluorescence spectrum of compound 1-1 in dichloromethane solution is shown in FIG. 1.
Example 2: synthesis of Compounds 1-17
(Synthesis of intermediate M2)
The synthetic route for intermediate M2 is shown below:
in a 250mL single-neck flask, p-bromobenzimidate hydrazide hydrochloride (5.0g, 20mmol), phenylglyoxal hydrate (2.7g, 20mmol) and 120mL of absolute ethanol were added in this order, and the reaction was stirred under reflux for 12 hours. After the reaction, the solid was collected by suction filtration and washed with a small amount of anhydrous ethanol. The crude product was further purified by column chromatography (petroleum ether: dichloromethane ═ 3: 1 (V/V)). The solvent was evaporated and dried to give 3.7g of a pale yellow solid with a yield of 60%. Ms (ei): m/z: 312.02[ M ]+]。Anal.calcd forC15H10BrN3(％)：C 57.71，H 3.23，N 13.46；found：C 57.69，H 3.25，N 13.43。
(Synthesis ofCompounds 1 to 17)
The synthetic routes for compounds 1-17 are shown below:
under nitrogen protection, intermediate M2(1.6g, 5mmol), 9-phenyl-9H, 9 'H-3, 3' -bicarbazole (2.1g, 5.2mmol), palladium acetate (11mg, 0.05mmol), tri-tert-butylphosphine tetrafluoroborate (29mg, 0.1mmol), sodium tert-butoxide (960mg, 10mmol) and 120mL of toluene were added in sequence to a 250mL Schlenk flask, and the reaction was stirred under reflux for 12 hours. After completion of the reaction, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane and 50mL of water, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, the organic layers were combined, the solvent was distilled off, and the residue was separated by column chromatography (petroleum ether: dichloromethane ═ 3: 1 (V/V)). The solvent was evaporated and dried to give 2.4g of a yellow solid in 76% yield. Ms (ei): m/z: 639.52[ M ]+]。Anal.calcdfor C45H29N5(％)：C 84.48，H 4.57，N 10.95；found：C 84.45，H 5.51，N 10.92。
Example 3: synthesis of Compounds 1-58
(Synthesis of Compounds 1-58)
The synthetic routes for compounds 1-58 are shown below:
under nitrogen protection, intermediate M2(1.6g, 5mmol), bis (4-biphenylyl) amine (1.7g, 5.2mmol), palladium acetate (11mg, 0.05mmol), tri-tert-butylphosphine tetrafluoroborate (29mg, 0.1mmol), sodium tert-butoxide (960mg, 10mmol) and 120mL of toluene were added in this order to a 250mL Schlenk flask, and the reaction was stirred under reflux for 12 hours. After completion of the reaction, the solvent was distilled off, the residue was dissolved in 200mL of dichloromethane and 50mL of water, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15mL of dichloromethane, the organic layers were combined, the solvent was distilled off, and the residue was separated by column chromatography (petroleum ether: dichloromethane ═ 3: 1 (V/V)). The solvent was evaporated and dried to give 1.8g of a yellow solid in 65% yield. Ms (ei): m/z: 552.34[ M ]+]。Anal.calcd forC39H28N4(％)：C 84.76，H 5.11，N 10.14；found：C 84.72，H 5.14，N 10.10。
Example 4: preparation of organic electroluminescent device 1 (organic EL device 1)
Ahole injection layer 3, ahole transport layer 4, anelectron blocking layer 5, alight emitting layer 6, ahole blocking layer 7, anelectron transport layer 8, anelectron injection layer 9 and acathode 10 were sequentially formed on atransparent anode 2 previously formed on aglass substrate 1 to prepare an organic electroluminescent device as shown in fig. 3.
Specifically, a glass substrate on which an ITO film having a film thickness of 100nm was formed was subjected to ultrasonic treatment in a Decon 90 alkaline cleaning solution, rinsed in deionized water, washed three times in acetone and ethanol, respectively, baked in a clean environment to completely remove moisture, washed with ultraviolet light and ozone, and bombarded on the surface with a low-energy cation beam. The strip is provided with ITOPlacing the glass substrate into a vacuum chamber, and vacuumizing to 4 × 10-4-2×10-5Pa. Then, 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN) was deposited on the ITO electrode-equipped glass substrate at a deposition rate of 0.2 nm/sec to form a layer having a film thickness of 10nm as a hole injection layer. N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB) was vapor-deposited on the hole injection layer at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 40nm as a hole transport layer. 4,4' -tris (N-carbazolyl) triphenylamine (TCTA) was vapor-deposited on the hole transport layer at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 5nm as an Electron Blocking Layer (EBL). On the electron blocking layer, double-source co-evaporation was performed at a deposition rate of 0.2nm/s for the compound of example 1 (compound 1) as a host material and 0.016nm/s for RD1 as a dopant material to form a layer with a thickness of 20nm as a light-emitting layer, and the doping weight ratio of RD1 was 2 wt%. On the light-emitting layer, aluminum (III) bis (2-methyl-8-quinolinolato) -4-phenylphenolate (BALq) was vapor-deposited at a vapor deposition rate of 0.2nm/s to form a layer having a film thickness of 10nm as a Hole Blocking Layer (HBL). On the hole-blocking layer, BALq was deposited at a deposition rate of 0.2nm/s to form a layer having a thickness of 40nm as an electron-transporting layer (ETL). On the electron transport layer, 8-hydroxyquinoline-lithium (Liq) was vapor-deposited at a vapor deposition rate of 0.1nm/s to form a layer having a film thickness of 2nm as an electron injection layer. Finally, aluminum is vapor-deposited at a vapor deposition rate of 0.5nm/s or more to form a cathode having a film thickness of 100 nm.
Examples 5 to 6: preparation of organic EL devices 2-3
An organic EL device was produced under the same conditions as theorganic EL device 1 except that the compounds in table 1 below were used instead of the compounds in each layer of example 4, respectively. The electroluminescence spectrum of theorganic EL device 2 is shown in fig. 2.
Comparative examples 1 to 2: preparation of organic EL device comparative examples 1 to 2
Comparative examples of organic EL devices were prepared under the same conditions as theorganic EL device 1 except that the compounds in table 1 below were used instead of the compounds in each layer of example 4.
The examples and comparative examples relate to the following structures of compounds:
TABLE 1
The light emission characteristics of theorganic EL devices 1 to 3 produced in examples 4 to 8 and the organic EL devices produced in comparative examples 1 to 2 were measured at normal temperature under the application of a direct current voltage in the atmosphere. The measurement results are shown in table 2.
The current-luminance-voltage characteristics of the device were obtained from a Keithley source measuring system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) with calibrated silicon photodiodes, the electroluminescence spectra were measured by a Photo research PR655 spectrometer, and the external quantum efficiencies of the devices were calculated by the method of the documents adv.mater, 2003,15, 1043-.
The lifetime of the device was measured as: the emission luminance (initial luminance) at the start of light emission was set to 10000cd/m2Constant current driving is performed until the light emission luminance decays to 9500cd/m2(corresponding to 95%, where the initial brightness is taken as 100%: 95% decay). Device lifetime with RD1 as dopant is 10000cd/m2For initial luminance, attenuation to 9500cd/m2(corresponding to 95%, where the initial brightness is taken as 100%: 95% decay). All devices were encapsulated in a nitrogen atmosphere.
TABLE 2
As can be seen from table 2, the present invention's metatriazine derivatives give excellent performance data.
Organic EL device comparative example 2 andorganic EL device 2 used RD1 as a dopant, and the host material constituting material of theorganic EL device 2 wascompounds 1 to 17 of the present invention. As can be seen from the comparison of the device performance data, theorganic EL device 2 has a lower operating voltage, the maximum external quantum efficiency is improved by nearly 10%, and the device lifetime (95%) is also longer.
Compared with the materials commonly used in the prior art, the unsym-triazine derivative can effectively reduce the working voltage, improve the external quantum efficiency and prolong the service life of devices.
The invention of the partial triazine derivatives have excellent luminous efficiency and life characteristics, low driving voltage. Therefore, an organic electroluminescent device having an excellent lifetime can be prepared from the compound.
The above description is only for the purpose of illustrating the present invention and is not intended to limit the scope of the present invention, and it will be apparent to those skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope of the present invention.
Claims (10)
1. A partial triazine derivative represented by the following general formula (1):
wherein L is1And L2Each independently represents one or more of a single bond, a carbonyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or an aromatic heterocyclic group having 5 to 18 carbon atoms;
m and n are each independently an integer of 0 to 5, and m and n are not 0 at the same time;
A1and A2Each independently represents Ar1、Ar2、
Ar1～Ar4Each independently represents optionally substituted one or more R1Substituted, aromatic hydrocarbon radical having 6 to 30 carbon atoms or optionally substituted by one or more R1One or more substituted aromatic heterocyclic groups having 5 to 30 carbon atoms;
z represents CR1Or N;
R1represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, NO2、N(R2)2、OR2、SR2、C(＝O)R2、P(＝O)R2、Si(R2)3One or more of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms;
R2represents one or more of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 carbon atoms.
2. The metatriazine derivative according to claim 1, which is represented by the following general formula (I) or (II):
said L1、L2And said Ar1～Ar4Have the meaning as defined in claim 1.
3. The metatriazine derivative according to claim 1, wherein Ar is selected from the group consisting of1、Ar2、Ar3And Ar4Each independently selected from the following groups:
wherein the dotted line represents and L1、L2Or an N-bonded bond.
R1Has the meaning as defined for the general formula (1).
4. The partial triazine derivative according to any one of claims 1 to 3,
m and n are each independently an integer of 0 to 2, and m and n are not 0 at the same time;
L1、L2each independently represents one or more of a single bond, a carbonyl group, a phenyl group, a triazinyl group or a biphenyl group;
R1and R2Each independently represents one or more of phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzothienocarbazole, benzofurocarbazole, benzofluorenocarbazole, benzanthracene, triphenylene, fluorenyl, spirobifluorenyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, indenocarbazolyl, benzimidazolyl, diphenyl-oxadiazolyl, diphenyl boron group, triphenyl phosphoxy, diphenyl phosphoxy, triphenyl silicon group, or tetraphenyl silicon group.
5. The partial triazine derivative according to any one of claims 1 to 3, wherein the partial triazine derivative represented by the general formula (1) is selected from the group consisting of:
6. an electronic device comprising the triazine derivative according to any one of claims 1 to 5.
7. The electronic device according to claim 6, wherein the electronic device is an organic electroluminescent device, an organic field effect transistor, or an organic solar cell;
wherein the organic electroluminescent device comprises: a first electrode, a second electrode provided so as to face the first electrode, and at least one organic layer located between the first electrode and the second electrode, wherein at least one of the organic layers comprises the partial triazine derivative according to any one of claims 1 to 5.
8. The electronic device of claim 7, wherein the organic layer is one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, or an electron transport layer.
9. Use of the partial triazine compound according to any one of claims 1 to 3 as a light-emitting material, an electron-transporting material, an electron-blocking material, a hole-injecting material or a hole-blocking material in an electronic device.
10. Use according to claim 9, characterized in that the electronic device is an organic electroluminescent device, an organic field effect transistor or an organic solar cell.
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| WO2020064662A2 (en)* | 2018-09-27 | 2020-04-02 | Merck Patent Gmbh | Method for producing sterically hindered, nitrogen-containing heteroaromatic compounds |
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| US3594349A (en)* | 1966-11-08 | 1971-07-20 | Ashland Oil Inc | Substituted polymeric as-triazines |
| CN107857759A (en)* | 2017-12-04 | 2018-03-30 | 吉林奥来德光电材料股份有限公司 | Organic luminescent compounds and preparation method and organic luminescent device |
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