CN112079778A - Organic light-emitting compound and preparation method and device thereof - Google Patents
Organic light-emitting compound and preparation method and device thereofDownload PDFInfo
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- CN112079778A CN112079778ACN202010984289.0ACN202010984289ACN112079778ACN 112079778 ACN112079778 ACN 112079778ACN 202010984289 ACN202010984289 ACN 202010984289ACN 112079778 ACN112079778 ACN 112079778A
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Abstract
Description
Translated fromChinese技术领域technical field
本发明涉及有机发光材料技术领域，具体涉及一种有机发光化合物及其制备方法和器件。The present invention relates to the technical field of organic light-emitting materials, in particular to an organic light-emitting compound and a preparation method and device thereof.
背景技术Background technique
有机发光现象是指使用有机材料将电能转换成光能的现象。利用有机发光现象的有机发光器件通常具有这样的结构，其包括阳极、阴极和其间的有机材料层。The organic light-emitting phenomenon refers to a phenomenon in which an organic material is used to convert electrical energy into light energy. An organic light-emitting device utilizing an organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
有机材料层形成为由不同材料形成的多层结构以提高有机发光器件的效率和稳定性，例如可由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。在这样的有机发光器件结构中，当在两个电极之间施加电压时，空穴和电子分别从阳极和阴极注入有机材料层，当注入的空穴和电子相遇时形成激子，并且当这些激子返回基态时发光。The organic material layer is formed into a multi-layered structure formed of different materials to improve the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In such an organic light-emitting device structure, when a voltage is applied between two electrodes, holes and electrons are injected into the organic material layer from the anode and cathode, respectively, excitons are formed when the injected holes and electrons meet, and when these The excitons emit light when they return to the ground state.
材料类型和搭配形式具有丰富性和多样性的特点。另外，对于不同结构的OLED器件搭配而言，所使用的光电功能材料具有较强的选择性，相同的材料在不同结构器件中的性能表现也可能完全迥异。因此，针对当前OLED器件的产业应用要求以及OLED器件的不同功能膜层，器件的光电特性需求，必须选择更适合、性能更高的OLED功能材料或材料组合，才能实现器件的高效率、长寿命和低电压的综合特性。就当前的OLED显示照明产业的实际需求而言，目前OLED材料的发展还远远不够，落后于面板制造企业的要求，作为材料企业开发更高性能的有机功能材料显得尤为重要。Material types and collocation forms are characterized by richness and diversity. In addition, for the collocation of OLED devices with different structures, the optoelectronic functional materials used have strong selectivity, and the performance of the same material in devices with different structures may also be completely different. Therefore, in view of the current industrial application requirements of OLED devices, the different functional layers of OLED devices, and the optoelectronic characteristics requirements of devices, it is necessary to select more suitable and higher-performance OLED functional materials or material combinations in order to achieve high efficiency and long life of the device. and comprehensive characteristics of low voltage. As far as the actual needs of the current OLED display lighting industry are concerned, the current development of OLED materials is far from enough and lags behind the requirements of panel manufacturing companies. It is particularly important for material companies to develop higher-performance organic functional materials.
发明内容SUMMARY OF THE INVENTION
本发明的目的是提供一种新型结构的有机发光化合物及其制备方法和器件，将其用于有机电致发光器件的制备，作为其中的空穴传输材料，所制得的有机电致发光器件驱动电压明显降低，发光效率以及寿命得到显著提高。The object of the present invention is to provide an organic light-emitting compound with a novel structure and a preparation method and device thereof, which are used for the preparation of organic electroluminescent devices, and as the hole transport material therein, the prepared organic electroluminescent device The driving voltage is significantly reduced, and the luminous efficiency and lifetime are significantly improved.
为了实现上述目的，本发明的技术方案具体如下：In order to achieve the above object, the technical scheme of the present invention is as follows:
本发明提供一种有机发光化合物，其结构式如化学式1所示：The present invention provides an organic light-emitting compound whose structural formula is shown in Chemical Formula 1:
式中：where:
X、Y可为链接键、-O-、-S-、-N(R1)-、-Si(R2)(R3)-或-C(R4)(R5)-；且X和Y至多有一个为连接键；X, Y can be a link bond, -O-, -S-, -N(R1 )-, -Si(R2 )(R3 )- or -C(R4 )(R5 )-; and X and Y have at most one connection key;
R1～R5各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C2-C30烯基、经取代或未经取代的C2-C30炔基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的3到7元杂环烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或多环、具体为C3-C30脂肪族环或(C6-C30)芳香族环，其碳原子可置换成至少一个选自氮、氧和硫的杂原子；R1 to R5 each independently represent substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkynyl or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted 3 to 7 Membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted 3 to 30 membered heteroaryl; or joined with adjacent substituents to form substituted or unsubstituted Monocyclic or polycyclic, in particular C3-C30 aliphatic or (C6-C30) aromatic rings, the carbon atoms of which can be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur;
Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3到30元杂芳基；或与相邻取代基连接形成单环或多环、具体为C3-C30脂肪族环或芳香族环，其碳原子可置换为至少一个选自氮、氧和硫的杂原子；Ar1 and Ar2 each independently represent a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group ; Or connect with adjacent substituents to form a monocyclic or polycyclic ring, specifically a C3-C30 aliphatic ring or an aromatic ring, the carbon atom of which can be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur;
优选所述Ar1和Ar2各自独立地选自经取代或未经取代C6-C20芳基、经取代或未经取代的C15-C26杂芳基；Preferably said Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C15-C26 heteroaryl;
L为链接键或经取代或未经取代的C6-C30芳基；经取代或未经取代的3元-30元杂芳基；优选为链接键或苯、氘代苯；L is a link bond or a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted 3-membered-30-membered heteroaryl group; preferably a link bond or benzene, deuterated benzene;
n为1-4的整数，优选为1或2；n is an integer of 1-4, preferably 1 or 2;
上述所述的“经取代或未经取代”中的“经取代”的取代基选自氢、氘、卤素、氰基、羧基、硝基、羟基、氨基、磺酸基、磺酰基、磷酸基、磷酰基、硅基、硼烷基；经取代或未经取代的(C1-C30)烃类(烷基、烯基、炔基)、经取代或未经取代的(C1-C30)烷氧基、经取代或未经取代的(C3-C30)环烷基、经取代或未经取代的(C3-C30)环烯基、经取代或未经取代的(C3-C30)杂环烷基、经取代或未经取代的(C6-C30)芳基、经取代或未经取代的(3到30元)杂芳基、经取代或未经取代的(C6-C30)芳氧基、经取代或未经取代的(C6-C30)芳胺基；或与相邻取代基连接形成经取代或未经取代的单环或多环(C3-C30)脂肪族环或经取代或未经取代的(3到30元)芳香族环，其碳原子可置换成至少一个选自氮、氧和硫杂原子。The "substituted" substituent in the above-mentioned "substituted or unsubstituted" is selected from hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, sulfonic acid, sulfonyl, phosphate , phosphoryl, silyl, boryl; substituted or unsubstituted (C1-C30) hydrocarbons (alkyl, alkenyl, alkynyl), substituted or unsubstituted (C1-C30) alkoxy base, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (C3-C30)heterocycloalkyl , substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30-membered) heteroaryl, substituted or unsubstituted (C6-C30) aryloxy, Substituted or unsubstituted (C6-C30) arylamine group; or linked with adjacent substituents to form a substituted or unsubstituted monocyclic or polycyclic (C3-C30) aliphatic ring or substituted or unsubstituted (3 to 30 membered) aromatic rings whose carbon atoms can be replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur.
通式1可由式2-5表示：General formula 1 can be represented by formulas 2-5:
X、Y范围与上述相同；The X and Y ranges are the same as above;
L1、L2、L3范围与上述L范围相同；The L1, L2, L3 ranges are the same as the above L ranges;
Ar1-Ar4范围与上述Ar1、Ar2范围相同；The range of Ar1 -Ar4 is the same as the range of Ar1 and Ar2 above;
优选的，上述有机电致发光化合物的结构式为以下结构式中的任一种：Preferably, the structural formula of the above-mentioned organic electroluminescent compound is any one of the following structural formulas:
以上仅列举了一些具体的结构形式，但是这系列化合物不局限于上述分子结构，凡是一些简单基团及其取代的基团和取代位置的简单变换就可以得到其他具体的分子结构，在此不再一一赘述。The above only enumerates some specific structural forms, but this series of compounds is not limited to the above-mentioned molecular structures. Any simple transformation of some simple groups and their substituted groups and substitution positions can obtain other specific molecular structures. Repeat them one by one.
本发明还提供一种有机电致发光化合物的制备方法，包括以下步骤：The present invention also provides a preparation method of an organic electroluminescent compound, comprising the following steps:
通式1制备方法：General formula 1 preparation method:
1：当L不为链接键时：1: When L is not a link key:
将原料1(1eq)和化合物1(1eq)溶于甲苯乙醇和水的混合溶液中，用氮气充分置换空气三次；将氮气保护下加入钯催化剂(0.01eq)和(2eq)碳酸钾，搅拌均匀，升温至回流，反应10h；冷却至室温，分液后，接着用二氯甲烷萃取水相，合并有机层；接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用柱色谱法纯化剩余物质获得通式1所示的化合物。Dissolve raw material 1 (1eq) and compound 1 (1eq) in a mixed solution of toluene ethanol and water, fully replace the air with nitrogen three times; add palladium catalyst (0.01eq) and (2eq) potassium carbonate under nitrogen protection, stir well , heated to reflux, and reacted for 10 h; cooled to room temperature, and after liquid separation, the aqueous phase was then extracted with dichloromethane, and the organic layers were combined; then the extracted organic layers were dried with sodium sulfate, and the solvent was removed with a rotary evaporator; The remaining material was purified by chromatography to obtain the compound of general formula 1 .
2：当L为连接键时：2: When L is the connection key:
在氮气保护下，将原料1-1(1eq)和化合物1(1eq)溶于甲苯溶液中，加入三(二亚苄基丙酮)二钯(0.01eq)，三叔丁基膦(0.05eq)及叔丁醇钠(2eq)，搅拌均匀，升温至90℃，并回流反应5h；反应结束后，稍降温度，使用硅藻土进行过滤，除去盐以及催化剂，滤液冷却至室温后，水洗三遍，保留有机相，接着用乙酸乙酯萃取水相；合并有机相后，使用无水硫酸镁进行干燥，并且使用旋转式蒸发器去除溶剂；利用二氯甲烷和石油醚(V二氯甲烷:V石油醚＝10:4)的混合溶液，通过柱色谱法纯化剩余物质获得通式1-1所示的化合物。Under nitrogen protection, raw material 1-1 (1eq) and compound 1 (1eq) were dissolved in toluene solution, tris(dibenzylideneacetone)dipalladium (0.01eq), tri-tert-butylphosphine (0.05eq) were added and sodium tert-butoxide (2eq), stirred evenly, heated to 90°C, and refluxed for 5h; after the reaction, the temperature was slightly lowered, and celite was used for filtration to remove salt and catalyst. After the filtrate was cooled to room temperature, washed with water for three Again, the organic phase was retained, followed by extraction of the aqueous phase with ethyl acetate; after the combined organic phases were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator; dichloromethane and petroleum ether (V dichloromethane: V petroleum ether=10:4) mixed solution, the remaining substance was purified by column chromatography to obtain the compound represented by the general formula 1-1.
本发明还提供了如上技术方案所述的有机发光化合物的应用，将其应用于有机电致发光器件的制备。The present invention also provides the application of the organic light-emitting compound described in the technical solution above, which is applied to the preparation of the organic electroluminescent device.
经由上述方案，相较于现有技术，本发明具有如下有益效果：Through the above scheme, compared with the prior art, the present invention has the following beneficial effects:
本发明提供了一种有机电致发光化合物，将其用于有机电致发光器件的制备，作为其中的空穴传输材料，所制得的有机电致发光器件驱动电压明显降低，发光效率以及寿命得到显著提高；且本发明提供的有机发光化合物的制备方法，合成步骤简单，产物提纯容易、纯度高、产率高。The present invention provides an organic electroluminescent compound, which is used for the preparation of organic electroluminescent devices. As a hole transport material therein, the obtained organic electroluminescent device has significantly reduced driving voltage, luminous efficiency and lifetime. The method is significantly improved; and the preparation method of the organic light-emitting compound provided by the present invention has simple synthesis steps, easy product purification, high purity and high yield.
具体实施方式Detailed ways
下面将结合本发明的实施例，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts shall fall within the protection scope of the present invention.
实施例1：Example 1:
在氮气保护下，将原料1(50mmol)和化合物1(50mmol)溶于200.0ml甲苯溶液中，加入三(二亚苄基丙酮)二钯(0.5mmol)，三叔丁基膦(2.5mmol)及叔丁醇钠(100mmol)，搅拌均匀，升温至90℃，并回流反应5h；反应结束后，稍降温度，使用硅藻土进行过滤，除去盐以及催化剂，滤液冷却至室温后，水洗三遍，保留有机相，接着用乙酸乙酯萃取水相；合并有机相后，使用无水硫酸镁进行干燥，并且使用旋转式蒸发器去除溶剂；利用二氯甲烷和石油醚(V二氯甲烷:V石油醚＝10:4)的混合溶液，通过柱色谱法纯化剩余物质获得化合物1所示的化合物。(25.0g，产率为71.2％，MW:702.45)。Under nitrogen protection, raw material 1 (50 mmol) and compound 1 (50 mmol) were dissolved in 200.0 ml of toluene solution, tris(dibenzylideneacetone)dipalladium (0.5 mmol), tri-tert-butylphosphine (2.5 mmol) were added and sodium tert-butoxide (100mmol), stirred evenly, heated to 90°C, and refluxed for 5h; after the reaction, the temperature was slightly lowered, and celite was used for filtration to remove salt and catalyst. After the filtrate was cooled to room temperature, washed with water for three Again, the organic phase was retained, followed by extraction of the aqueous phase with ethyl acetate; after the organic phases were combined, dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator; dichloromethane and petroleum ether (V dichloromethane: V petroleum ether=10:4) mixed solution, the remaining substance was purified by column chromatography to obtain the compound represented by compound 1. (25.0 g, 71.2% yield, MW: 702.45).
实施例2：Example 2:
将原料28(50mmol)和化合物28(50mmol)溶于(180ml甲苯60ml乙醇和H2O60ml)的混合溶液中，用氮气充分置换空气三次；将氮气保护下加入四三苯基膦钯(0.5mmol)和碳酸钾(100mmol)，搅拌均匀，升温至回流，反应10h；冷却至室温，分液后，接着用二氯甲烷萃取水相，合并有机层；接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用柱色谱法纯化剩余物质获得化学产物28所示的化合物。(26.1g，产率为65.1％，MW:802.43)。The raw material 28 (50 mmol) and compound 28 (50 mmol) were dissolved in a mixed solution of (180 ml of toluene, 60 ml of ethanol and 60 ml of H2 O), and the air was fully replaced with nitrogen three times; tetrakistriphenylphosphine palladium (0.5 mmol) was added under nitrogen protection. ) and potassium carbonate (100mmol), stirred evenly, heated to reflux, and reacted for 10h; cooled to room temperature, after liquid separation, the aqueous phase was then extracted with dichloromethane, and the organic layers were combined; then use sodium sulfate to dry the extracted organic layer, and The solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography to give the compound shown in chemical product 28. (26.1 g, 65.1% yield, MW: 802.43).
实施例3：Example 3:
将原料25(50mmol)和化合物25-1(50mmol)、化合物25-2(50mmol)溶于(180ml甲苯60ml乙醇和H2O60ml)的混合溶液中，用氮气充分置换空气三次；将氮气保护下加入四三苯基膦钯(0.5mmol)和碳酸钾(100mmol)，搅拌均匀，升温至回流，反应10h；冷却至室温，分液后，接着用二氯甲烷萃取水相，合并有机层；接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用柱色谱法纯化剩余物质获得化学产物25所示的化合物。(26.2g，产率为60.9％，MW:860.42)。Raw material 25 (50 mmol), compound 25-1 (50 mmol) and compound 25-2 (50 mmol) were dissolved in a mixed solution of (180 ml of toluene, 60 ml of ethanol and H2 O 60 ml), and the air was fully replaced with nitrogen three times; Add tetrakistriphenylphosphine palladium (0.5mmol) and potassium carbonate (100mmol), stir evenly, heat up to reflux, and react for 10h; cool to room temperature, after liquid separation, then extract the aqueous phase with dichloromethane, and combine the organic layers; then The extracted organic layer was dried using sodium sulfate, and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography to obtain the compound shown in chemical product 25. (26.2 g, 60.9% yield, MW: 860.42).
实施例4：Example 4:
将原料47(50mmol)和化合物47(50mmol)溶于(180ml甲苯60ml乙醇和H2O60ml)的混合溶液中，用氮气充分置换空气三次；将氮气保护下加入四三苯基膦钯(0.5mmol)和碳酸钾(100mmol)，搅拌均匀，升温至回流，反应10h；接着用二氯甲烷和水萃取混合物；接着使用硫酸钠干燥萃取的有机层，并且使用旋转式蒸发器去除溶剂；用柱色谱法纯化剩余物质获得化学产物47所示的化合物。(14.8g，产率为68.1％，MW:727.41)。The raw material 47 (50 mmol) and compound 47 (50 mmol) were dissolved in a mixed solution of (180 ml of toluene, 60 ml of ethanol and 60 ml of H2 O), and the air was fully replaced with nitrogen three times; tetrakistriphenylphosphine palladium (0.5 mmol) was added under nitrogen protection ) and potassium carbonate (100 mmol), stirred evenly, heated to reflux, and reacted for 10 h; then the mixture was extracted with dichloromethane and water; then the extracted organic layer was dried with sodium sulfate, and the solvent was removed with a rotary evaporator; with column chromatography The remaining material was purified by the method to obtain the compound shown as chemical product 47. (14.8 g, 68.1% yield, MW: 727.41).
其他化合物的合成方法与上述实施例相同，在此不一一赘述，其他合成实施例质谱和分子式如下表所示：The synthetic methods of other compounds are the same as the above-mentioned embodiments, and will not be repeated here. The mass spectra and molecular formulas of other synthetic embodiments are shown in the following table:
器件实施例1：Device Example 1:
将本发明实施例合成的化合物作为空穴传输材料，采用通常方法制备有机电致发光器件。首先ITO(阳极)上面蒸镀N1-(萘-2-yl)-N4,N4-二(4-(萘-2-yl(苯基)氨基)苯基)-N1-苯基苯-1,4-二胺("2-TNATA")45nm厚度，紧接着蒸镀本发明合成的化合物1厚度45nm为空穴传输层、主体物质4,4'-N,N'-二咔唑-联苯("CBP")和掺杂物质三(2-苯基吡啶)合铱("Ir(ppy)3")按照98：2重量比混合蒸镀20nm厚度为发光层、蒸镀空穴阻挡层("BAlq")10nm厚度、蒸镀"Alq3"40nm厚度为电子传输层、蒸镀电子注入层LiF 0.2nm厚度、蒸镀阴极Al135nm厚度，形成有机电致发光器件。Using the compounds synthesized in the embodiments of the present invention as hole transport materials, the organic electroluminescent devices are prepared by common methods. First, N1-(naphthalene-2-yl)-N4, N4-bis(4-(naphthalene-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1, 4-Diamine ("2-TNATA") 45nm thick, followed by vapor deposition of the compound 1 synthesized by the present invention with a thickness of 45nm for the hole transport layer, the host substance 4,4'-N,N'-dicarbazole-biphenyl ("CBP") and dopant tris(2-phenylpyridine) iridium ("Ir(ppy)3") were mixed and evaporated in a weight ratio of 98:2 to a thickness of 20 nm to form a light-emitting layer, an evaporated hole blocking layer ( "BAlq") 10nm thickness, vapor deposition "Alq3" 40nm thickness is electron transport layer, vapor deposition electron injection layer LiF 0.2nm thickness, vapor deposition cathode Al 135nm thickness, forming organic electroluminescence device.
器件实施例2-9：按照器件实施例1的方法，蒸镀器件实施例2-9，不同之处将化合物1替换成化合物12、化合物17、化合物23、化合物25、化合物28、化合物35、化合物44、化合物47；Device Example 2-9: According to the method of Device Example 1, Device Example 2-9 was evaporated, except that Compound 1 was replaced with Compound 12, Compound 17, Compound 23, Compound 25, Compound 28, Compound 35, Compound 44, Compound 47;
比较例：Comparative example:
采用与器件实施例1的同样方法制备有机电致发光器件，不同之处在于实施例1中的化合物1以外，分别用比较化合物1-3来制备得到器件比较例1-器件比较例3。The organic electroluminescent device was prepared by the same method as in Device Example 1, except that the Comparative Compounds 1-3 were used to prepare Device Comparative Example 1 to Device Comparative Example 3 except for Compound 1 in Example 1.
本发明的器件实施例1-器件实施例9，器件比较例1-器件比较例3制备的有机电致发光器件加偏压以后用Photoresearch公司的PR-650测试电致发光特性(EL)，在6000cd/m2基准亮度下，用Mcscience制备的寿命装备测试T95。测定结果如表1表示。Device Example 1 of the present invention - Device Example 9, Device Comparative Example 1 - Device Comparative Example 3 The organic electroluminescent devices prepared by the device were biased and tested for electroluminescence characteristics (EL) with PR-650 of Photoresearch Company. Under the benchmark brightness of 6000cd/m2, T95 was tested with the lifetime equipment prepared by Mcscience. The measurement results are shown in Table 1.
表1：Table 1:
由表1的结果能确认使用本发明提供的化合物作为空穴传输材料制备的有机电致发光器件表现出高的发光效率及长寿命并降低驱动电压。From the results in Table 1, it can be confirmed that the organic electroluminescent device prepared using the compound provided by the present invention as the hole transport material exhibits high luminous efficiency and long life and reduces the driving voltage.
以上的说明是本发明的简单的说明，本发明的应用不限于上述举例，对本领域普通技术人员来说，可以根据上述说明范围内加以改进或变换，所有这些改进和变换应属于本发明权利要求的保护范围。假如本发明实施例是为了说明本发明而已，发明内容范围不是限定在这个范围。本发明的保护范围是必须下面权利要求范围内解析，跟本发明同等范围的一切技术是包含在本发明的权利范围内。The above description is a simple description of the present invention. The application of the present invention is not limited to the above examples. For those of ordinary skill in the art, improvements or transformations can be made within the scope of the above descriptions. All these improvements and transformations should belong to the claims of the present invention. scope of protection. If the embodiments of the present invention are only for illustrating the present invention, the scope of the content of the invention is not limited to this scope. The protection scope of the present invention must be analyzed within the scope of the following claims, and all technologies of the same scope as the present invention are included in the scope of the right of the present invention.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116444467A (en)* | 2023-06-19 | 2023-07-18 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117024454A (en)* | 2022-04-28 | 2023-11-10 | 江苏三月科技股份有限公司 | Resonant organic compound and organic electroluminescent device thereof |
| CN117024454B (en)* | 2022-04-28 | 2025-06-13 | 江苏三月科技股份有限公司 | A resonant organic compound and an organic electroluminescent device thereof |
| CN116444467A (en)* | 2023-06-19 | 2023-07-18 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device |
| CN116444467B (en)* | 2023-06-19 | 2023-10-13 | 吉林奥来德光电材料股份有限公司 | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device |
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