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CN110627659A - Organic light-emitting compound and its preparation method and device - Google Patents

Organic light-emitting compound and its preparation method and device Download PDF

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Publication number
CN110627659A
CN110627659A CN201910916424.5A CN201910916424A CN110627659A CN 110627659 A CN110627659 A CN 110627659A CN 201910916424 A CN201910916424 A CN 201910916424A CN 110627659 A CN110627659 A CN 110627659A
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China
Prior art keywords
substituted
group
unsubstituted
compound
organic light
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CN201910916424.5A
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Chinese (zh)
Inventor
汪康
孙向南
金成寿
张鹤
赵贺
孙峰
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Priority to CN201910916424.5A priority Critical patent/CN110627659A/en
Publication of CN110627659A publication Critical patent/CN110627659A/en
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Abstract

The invention relates to an organic light-emitting compound, a preparation method and a device thereof, wherein the structure of the organic light-emitting compound is shown as a chemical formula 1:

Description

有机发光化合物及其制备方法和器件Organic light-emitting compound and its preparation method and device

技术领域technical field

本发明涉及发光材料技术领域，具体涉及一种有机发光化合物及其制备方法和器件。The invention relates to the technical field of luminescent materials, in particular to an organic luminescent compound, a preparation method and a device thereof.

背景技术Background technique

OLED有机半导体功能材料，作为新一代显示技术应运而生，从信息显示到固态照明器件，伴随着广阔的应用前景和技术上的突飞猛进，OLED已经逐渐迈入了产业化进程。OLED organic semiconductor functional materials have emerged as a new generation of display technology. From information display to solid-state lighting devices, with broad application prospects and rapid technological advancement, OLED has gradually entered the process of industrialization.

OLED是空穴和电子双注入型发光器件，将电能直接转化为有机半导体材料分子的光能。OLED通常为双加层结构，即有机功能层夹在透明导电阳极和金属阴极之间。在阳极接正极、金属阴极接负极的正向电压驱动下，空穴和电子分别从透明阳极和金属阴极注入有机功能层，经过其他功能层传输到发光层，在库伦作用力下相互靠近，最后成功俘获成为处于束缚能级的电子空穴对即激子，激子辐射退激发发出光子，即有机半导体材料发光。OLED is a hole and electron double-injection light-emitting device, which directly converts electrical energy into light energy of organic semiconductor material molecules. OLEDs usually have a double-layer structure, that is, an organic functional layer is sandwiched between a transparent conductive anode and a metal cathode. Driven by the positive voltage of the anode connected to the positive electrode and the metal cathode connected to the negative electrode, holes and electrons are respectively injected into the organic functional layer from the transparent anode and the metal cathode, transported to the light-emitting layer through other functional layers, and approach each other under the Coulomb force, and finally Successful capture becomes electron-hole pairs in the bound energy level, namely excitons, and the excitons radiate and de-excite to emit photons, that is, the organic semiconductor material emits light.

目前有机电致发光材料的研究已经应用到很多领域，很多企业和人才已经纷纷投身到这一领域，大量性能优良的有机电致发光材料被陆续开发出来，但该技术的产业化进程仍然面临很多关键性问题，开发更多更高效性能的有机材料就显得尤为重要和迫切。At present, the research on organic electroluminescent materials has been applied to many fields. Many enterprises and talents have devoted themselves to this field. A large number of organic electroluminescent materials with excellent performance have been developed one after another. As a key issue, it is particularly important and urgent to develop more and more efficient organic materials.

发明内容Contents of the invention

本发明的目的是新型的具有蒽和胺结构的有机发光化合物及其制备方法和器件。含有该类材料的有机电致发光器件具有较高的发光效率以及较长的寿命。The object of the present invention is a novel organic light-emitting compound with anthracene and amine structure and its preparation method and device. The organic electroluminescent device containing this kind of material has higher luminous efficiency and longer life.

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 solution of the present invention is specifically as follows:

本发明提供一种有机发光化合物，其结构如化学式1所示：The present invention provides an organic luminescent compound, the structure of which is shown in Chemical Formula 1:

其中，Ar1、Ar2各自独立地为经取代或未经取代的芳基、经取代或未经取代的芳基胺基、或者经取代或未经取代的杂环基，或者彼此结合成环；Wherein, Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a ring ;

Ar3为氢、氘、卤素、腈基、硝基、羟基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、或者取代或未取代的杂环基，或者与相邻基团彼此结合成环； Ar is hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocycle group, or combine with adjacent groups to form a ring;

R为氢、氘、卤素、腈基、硝基、羟基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、取代或未取代的芳基烷基、取代或未取代的芳基膦基、或者取代或未取代的杂环基，或者相邻基团彼此结合成环；R is hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl , a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group, or adjacent groups combine to form a ring;

L为连接键，或者选自取代或未取代的烷基、取代或未取代的芳基、或取代或未取代的杂环基。L is a linking bond, or is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

在上述技术方案中，Ar3优选自芳香取代基团，具体的优选为经取代或未经取代的苯基、联苯基、三联苯基、萘基、芴基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、二苯并噻吩基、芘基、和菲基中的一种。In the above-mentioned technical scheme, Ar 3 is preferably selected from aromatic substituent groups, specifically preferably substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofuryl, benzo One of thienyl, dibenzofuryl, dibenzothienyl, pyrenyl, and phenanthrenyl.

在上述技术方案中，Ar3进一步优选为苯基、联苯基、三联苯基、萘基、芴基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、二苯并噻吩基、芘基、和菲基中的一种。 In the above technical scheme, Ar is further preferably phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, One of pyrenyl, and fiji.

在上述技术方案中，L优选为苯基、联苯基、三联苯基、萘基、芘基、菲基、芴基、螺基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、和二苯并噻吩基中的一种。In the above technical scheme, L is preferably phenyl, biphenyl, terphenyl, naphthyl, pyrenyl, phenanthrenyl, fluorenyl, spiroyl, benzofuryl, benzothienyl, dibenzofuryl , and one of dibenzothienyl.

在上述技术方案中，L进一步优选为苯基或联苯基。In the above technical scheme, L is further preferably phenyl or biphenyl.

本发明中的烷基优选指的是C1～C20的直链烷基、支链烷基、环烷基；芳基为含有6～60个碳原子的芳基；杂环基为含有3～20个碳原子的杂环烷基或者杂芳基。The alkyl group in the present invention preferably refers to straight chain alkyl, branched chain alkyl, cycloalkyl of C1～C20; Aryl is the aryl that contains 6～60 carbon atoms; carbon atom heterocycloalkyl or heteroaryl.

在本发明中，相邻基团可任意指取代与相应取代基取代的原子直接连接的原子的取代基、在空间上最接近相应取代基设置的取代基，或者取代相应取代基取代的原子的另一取代基。与相邻基团结合形成环的含义是与相邻基团结合形成经取代或未经取代的脂肪族烃环、经取代或未经取代的芳族烃环、经取代或未经取代的脂肪族杂环、经取代或未经取代的芳族杂环、或经取代或未经取代的其稠环。In the present invention, the adjacent group can arbitrarily refer to the substituent that replaces the atom directly connected to the atom substituted by the corresponding substituent, the substituent that is located closest to the corresponding substituent in space, or the substituent that replaces the atom substituted by the corresponding substituent another substituent. Combining with an adjacent group to form a ring means combining with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic Aromatic heterocycle, substituted or unsubstituted aromatic heterocycle, or substituted or unsubstituted fused ring thereof.

在本发明中，“经取代或未经取代的”意指经选自以下的一个或更多个取代基取代：氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、胺基、氧化膦基团、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基膦基和杂环基，或者未经取代；或者意指经以上例示的取代基中两个或更多个取代基连接的取代基取代，或者未经取代。例如，两个或更多个取代基连接的取代基”可包括联苯基。换言之，联苯基可为芳基，或者可解释为两个苯基连接的取代基。In the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from: deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, acyl group Imino group, amine group, phosphine oxide group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, silyl group, boronyl group, alkyl group, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphino, and The heterocyclic group is either unsubstituted; or means substituted by a substituent connecting two or more substituents among the substituents exemplified above, or is unsubstituted. For example, a "substituent" in which two or more substituents are linked may include a biphenyl group. In other words, a biphenyl group may be an aryl group, or may be construed as a substituent in which two phenyl groups are linked.

在上述技术方案中，本发明的有机发光化合物最优选自以下结构中的任意一种：In the above technical scheme, the organic light-emitting compound of the present invention is optimally selected from any one of the following structures:

本发明还提供一种有机发光化合物的制备方法，包括以下步骤：The present invention also provides a method for preparing an organic luminescent compound, comprising the following steps:

将原料A与B、四三苯基膦合钯、及碳酸钾，加入甲苯中进行偶合反应，生成中间体C；在NBS的作用下溴化，生成中间体D；中间体D在正丁基锂的作用下形成硼酸中间体E；中间体E与原料F在四三苯基膦钯与碳酸钾作用下形成化学式1所示化合物；Add raw materials A and B, tetrakistriphenylphosphine palladium, and potassium carbonate to toluene for coupling reaction to generate intermediate C; brominate under the action of NBS to generate intermediate D; intermediate D is in n-butyl Boric acid intermediate E is formed under the action of lithium; intermediate E and raw material F form a compound shown in Chemical Formula 1 under the action of tetrakistriphenylphosphine palladium and potassium carbonate;

其合成路线如下：Its synthetic route is as follows:

其中，Hal代表卤素，其余取代基团与化学式1中的限定一致，这里不再赘述。Wherein, Hal represents halogen, and the remaining substituent groups are consistent with those defined in Chemical Formula 1, and will not be repeated here.

本发明还提供一种有机电致发光器件，包括阳极、阴极、及至于阳极和阴极之间的有机物层，所述有机物层含有本发明化学式1所示的化合物。The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer containing the compound represented by Chemical Formula 1 of the present invention.

在上述技术方案中，本发明化学式1所示的化合物是作为空穴传输层材料。In the above technical solution, the compound represented by Chemical Formula 1 of the present invention is used as the material of the hole transport layer.

本发明的有益效果是：The beneficial effects of the present invention are:

本发明提供的有机发光化合物是具有蒽和胺结构的新型结构的有机发光化合物，含有该类化合物的有机电致发光器件具有较高的发光效率以及较长的寿命。The organic luminescent compound provided by the invention is a novel organic luminescent compound with anthracene and amine structures, and the organic electroluminescent device containing the compound has higher luminous efficiency and longer life.

本发明提供的有机发光化合物的制备方法，原料易得，合成步骤简单，产率较高。The preparation method of the organic luminescent compound provided by the invention has easy-to-obtain raw materials, simple synthesis steps and high yield.

具体实施方式Detailed ways

实施例1化合物4的制备：The preparation of embodiment 1 compound 4:

在500mL的三口瓶，在通入氮气的保护下，加入27.06g化合物E-4(50mmol)、14.1g化合物F-4(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-4消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得27.97g化合物4，收率：80％，MW:700.02。In a 500mL three-necked flask, under the protection of nitrogen gas, 27.06g of compound E-4 (50mmol), 14.1g of compound F-4 (50mmol), 0.58g of tetrakistriphenylphosphine palladium (0.5mmol), 13.8 g potassium carbonate (100mmol), 150mL toluene, heated to reflux for 24 hours, followed by TLC until compound E-4 disappeared. After the completion of the reaction, naturally cool to 25°C, filter, rinse with 20mL*3 of toluene, wash the filtrate with 200g*3 of water to pH=7, dry the organic phase, and pass through a silica gel column. After passing through the column, rinse the silica gel column with 20mL*3. After passing through the column, combine the eluent and the liquid through the column by rotary evaporation to remove the solvent, beat the mixed solution of 300mL methanol and 100mL toluene twice, and obtain 27.97g of compound 4 after drying. Rate: 80%, MW: 700.02.

实施例2化合物7的制备：The preparation of embodiment 2 compound 7:

在500mL的三口瓶，在通入氮气的保护下，加入24.46g化合物E-7(50mmol)、11.6g化合物F-7(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-7消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得23.59g化合物7，收率：79％，MW:597.10。In a 500mL three-necked flask, under the protection of nitrogen gas, 24.46g of compound E-7 (50mmol), 11.6g of compound F-7 (50mmol), 0.58g of tetrakistriphenylphosphine palladium (0.5mmol), 13.8 g potassium carbonate (100mmol), 150mL toluene, heated to reflux for 24 hours, followed by TLC until compound E-7 disappeared. After the completion of the reaction, naturally cool to 25°C, filter, rinse with 20mL*3 of toluene, wash the filtrate with 200g*3 of water to pH=7, dry the organic phase, and pass through a silica gel column. After passing through the column, rinse the silica gel column with 20mL*3. After passing through the column, combine the eluent and the liquid through the column to remove the solvent by rotary evaporation. The mixed solution of 300mL methanol and 100mL toluene is beaten twice, and after drying, 23.59g of compound 7 is obtained. Rate: 79%, MW: 597.10.

实施例3化合物14的制备：The preparation of embodiment 3 compound 14:

在500mL的三口瓶，在通入氮气的保护下，加入31.51g化合物E-14(50mmol)、7.8g化合物F-14(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-14消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得27.15g化合物14，收率：82％，HPLC：99.8％，MW:662.42。In a 500mL three-necked flask, under the protection of nitrogen gas, 31.51g of compound E-14 (50mmol), 7.8g of compound F-14 (50mmol), 0.58g of tetrakistriphenylphosphine palladium (0.5mmol), 13.8 g potassium carbonate (100mmol), 150mL toluene, heated to reflux for 24 hours, followed by TLC until compound E-14 disappeared. After the completion of the reaction, naturally cool to 25°C, filter, rinse with 20mL*3 of toluene, wash the filtrate with 200g*3 of water to pH=7, dry the organic phase, and pass through a silica gel column. After passing through the column, rinse the silica gel column with 20mL*3. After passing through the column, combine the eluent and the passing liquid by rotary evaporation to remove the solvent, beat the mixed solution of 300mL methanol and 100mL toluene twice, and obtain 27.15g of compound 14 after drying. Yield: 82%, HPLC: 99.8%, MW: 662.42.

实施例4化合物31的制备：The preparation of embodiment 4 compound 31:

在500mL的三口瓶，在通入氮气的保护下，加入29.46g化合物E-31(50mmol)、9.4g化合物F-31(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-31消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得25.54g化合物31，收率：77％，MW:663.15。In a 500mL three-necked flask, under the protection of nitrogen gas, 29.46g of compound E-31 (50mmol), 9.4g of compound F-31 (50mmol), 0.58g of tetrakistriphenylphosphine palladium (0.5mmol), 13.8 g potassium carbonate (100mmol), 150mL toluene, heated to reflux for 24 hours, followed by TLC until compound E-31 disappeared. After the completion of the reaction, naturally cool to 25°C, filter, rinse with 20mL*3 of toluene, wash the filtrate with 200g*3 of water to pH=7, dry the organic phase, and pass through a silica gel column. After passing through the column, rinse the silica gel column with 20mL*3. After passing through the column, combine the eluent and the passing liquid by rotary evaporation to remove the solvent, beat the mixed solution of 300mL methanol and 100mL toluene twice, and obtain 25.54g of compound 31 after drying. Rate: 77%, MW: 663.15.

实施例5化合物33的制备：The preparation of embodiment 5 compound 33:

在500mL的三口瓶，在通入氮气的保护下，加入32.3g化合物E-33(50mmol)、11.6g化合物F-33(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-33消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得28.29g化合物33，收率：75％，MW:754.81。In a 500mL three-necked flask, under the protection of nitrogen gas, 32.3g of compound E-33 (50mmol), 11.6g of compound F-33 (50mmol), 0.58g of tetrakistriphenylphosphine palladium (0.5mmol), 13.8 g potassium carbonate (100mmol), 150mL toluene, heated to reflux for 24 hours, followed by TLC until compound E-33 disappeared. After the completion of the reaction, naturally cool to 25°C, filter, rinse with 20mL*3 of toluene, wash the filtrate with 200g*3 of water to pH=7, dry the organic phase, and pass through a silica gel column. After passing through the column, rinse the silica gel column with 20mL*3. After passing through the column, combine the eluent and the liquid through the column by rotary evaporation to remove the solvent, beat the mixed solution of 300mL methanol and 100mL toluene twice, and obtain 28.29g of compound 33 after drying. Rate: 75%, MW: 754.81.

实施例6化合物34的制备：The preparation of embodiment 6 compound 34:

在500mL的三口瓶，在通入氮气的保护下，加入39.82g化合物E-34(50mmol)、11.6g化合物F-34(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-34消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得32.56g化合物34，收率：72％，MW:903.79。In a 500mL three-necked flask, under the protection of nitrogen gas, 39.82g of compound E-34 (50mmol), 11.6g of compound F-34 (50mmol), 0.58g of tetraphenylphosphine palladium (0.5mmol), 13.8 g potassium carbonate (100mmol), 150mL toluene, heated to reflux for 24 hours, followed by TLC until compound E-34 disappeared. After the completion of the reaction, naturally cool to 25°C, filter, rinse with 20mL*3 of toluene, wash the filtrate with 200g*3 of water to pH=7, dry the organic phase, and pass through a silica gel column. After passing through the column, rinse the silica gel column with 20mL*3. After passing through the column, combine the eluent and the liquid through the column and rotate to remove the solvent. The mixed solution of 300mL methanol and 100mL toluene is beaten twice, and after drying, 32.56g of compound 34 is obtained. Rate: 72%, MW: 903.79.

实施例7化合物45的制备The preparation of embodiment 7 compound 45

在500mL的三口瓶，在通入氮气的保护下，加入32.87g化合物E-45(50mmol)、11.6g化合物F-45(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-45消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得30.23g化合物45，收率：79％，MW:765.14。In a 500mL three-necked flask, under the protection of nitrogen, add 32.87g compound E-45 (50mmol), 11.6g compound F-45 (50mmol), 0.58g tetrakistriphenylphosphine palladium (0.5mmol), 13.8 g potassium carbonate (100mmol), 150mL toluene, heated to reflux for 24 hours, followed by TLC until compound E-45 disappeared. After the completion of the reaction, naturally cool to 25°C, filter, rinse with 20mL*3 of toluene, wash the filtrate with 200g*3 of water to pH=7, dry the organic phase, and pass through a silica gel column. After passing through the column, rinse the silica gel column with 20mL*3. After passing through the column, combine the eluent and the liquid through the column and rotate to remove the solvent. The mixed solution of 300mL methanol and 100mL toluene is beaten twice, and after drying, 30.23g of compound 45 is obtained. Rate: 79%, MW: 765.14.

实施例8化合物50的制备The preparation of embodiment 8 compound 50

在500mL的三口瓶，在通入氮气的保护下，加入39.86g化合物E-50(50mmol)、11.6g化合物F-50(50mmol)、0.58g四三苯基膦合钯(0.5mmol)、13.8g碳酸钾(100mmol)、150mL甲苯，加热回流24小时，TLC跟踪至化合物E-50消失。反应完成后自然冷却至25℃，过滤，甲苯20mL*3淋洗，滤液水洗200g*3至pH＝7，有机相干燥后，过硅胶柱。过柱毕，20mL*3淋洗硅胶柱，过柱毕，淋洗液与过柱液合并旋蒸脱出溶剂，300mL甲醇与100mL甲苯混合溶液打浆两次，烘干后得33.0g化合物50，收率：73％，MW:905.21。In a 500mL three-necked flask, under the protection of nitrogen gas, 39.86g of compound E-50 (50mmol), 11.6g of compound F-50 (50mmol), 0.58g of tetrakistriphenylphosphine palladium (0.5mmol), 13.8 g potassium carbonate (100mmol), 150mL toluene, heated to reflux for 24 hours, followed by TLC until compound E-50 disappeared. After the completion of the reaction, naturally cool to 25°C, filter, rinse with 20mL*3 of toluene, wash the filtrate with 200g*3 of water to pH=7, dry the organic phase, and pass through a silica gel column. After passing through the column, rinse the silica gel column with 20mL*3. After passing through the column, combine the eluent and the liquid through the column and rotate to remove the solvent. The mixed solution of 300mL of methanol and 100mL of toluene is beaten twice, and after drying, 33.0g of compound 50 is obtained. Rate: 73%, MW: 905.21.

器件实施例1：Device Embodiment 1:

选取ITO玻璃为阳极，在蒸馏水中清洗2次，超声波洗涤30分钟，按异丙醇、丙酮、甲醇按顺序洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，干燥，转移到等离子体清洗机里，将上述基板洗涤5分钟，送到蒸镀机里。在已经准备好的ITO透明电极上依次蒸镀空穴注入层2-TNATA真空蒸镀厚度为60mm、空穴材料层为化合物4，真空蒸镀厚度为20nm、发光材料层按照90:10掺杂的CBP和Ir(ppy)3真空蒸镀厚度为30nm，电子传输层Alq3厚度为40nm、电子注入层LiF厚度为0.2nm，阴极Al厚度为150nm。Select ITO glass as the anode, wash it twice in distilled water, wash it ultrasonically for 30 minutes, wash it in sequence with isopropanol, acetone, and methanol for 30 minutes, wash it twice with distilled water, wash it ultrasonically for 10 minutes, dry it, and transfer it to plasma In the washing machine, wash the above-mentioned substrate for 5 minutes, and send it to the evaporation machine. On the prepared ITO transparent electrode, the hole injection layer 2-TNATA vacuum evaporation thickness is sequentially evaporated to 60mm, the hole material layer is compound 4, the vacuum evaporation thickness is 20nm, and the luminescent material layer is doped according to 90:10 The thickness of CBP and Ir(ppy)3 vacuum evaporation is 30nm, the thickness of electron transport layer Alq3 is 40nm, the thickness of electron injection layer LiF is 0.2nm, and the thickness of cathode Al is 150nm.

器件实施例2：Device embodiment 2:

本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例2制备的化合物7。The difference between this example and device example 1 is that the material of the hole transport layer of the device is changed from compound 4 to compound 7 prepared in example 2.

器件实施例3：Device embodiment 3:

本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例3制备的化合物14。The difference between this example and device example 1 is that the material of the hole transport layer of the device is changed from compound 4 to compound 14 prepared in example 3.

器件实施例4：Device Embodiment 4:

本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例4制备的化合物31。The difference between this example and device example 1 is that the material of the hole transport layer of the device is changed from compound 4 to compound 31 prepared in example 4.

器件实施例5：Device Embodiment 5:

本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例5制备的化合物33。The difference between this example and device example 1 is that the material of the hole transport layer of the device is changed from compound 4 to compound 33 prepared in example 5.

器件实施例6：Device embodiment 6:

本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例6制备的化合物34。The difference between this example and device example 1 is that the material of the hole transport layer of the device is changed from compound 4 to compound 34 prepared in example 6.

器件实施例7：Device Embodiment 7:

本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例7制备的化合物45。This example differs from Device Example 1 in that the material of the hole transport layer of the device is changed from Compound 4 to Compound 45 prepared in Example 7.

器件实施例8：Device Embodiment 8:

本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为实施例8制备的化合物50。This example differs from Device Example 1 in that the material of the hole transport layer of the device is changed from Compound 4 to Compound 50 prepared in Example 8.

器件对比例1：Device comparison example 1:

本实施例与器件实施例1不同之处在于：器件的空穴传输层材料由化合物4变为TCTA(4,4’,4”-三(咔唑-9-基)三苯胺)。The difference between this example and the device example 1 is that the material of the hole transport layer of the device is changed from compound 4 to TCTA (4,4',4"-tris(carbazol-9-yl)triphenylamine).

下表为本发明实施例制备的化合物以及TCTA制备的发光器件的发光特性测试结果。The following table shows the test results of the light-emitting characteristics of the compounds prepared in the examples of the present invention and the light-emitting devices prepared by TCTA.

由上表可知：与对比例化合物作为空穴传输层材料制备的有机电致发光器件相比，由本发明的化合物作为空穴传输层材料制备的有机电致发光器件具有更低的驱动电压，高的效率，及长寿命。As can be seen from the above table: compared with the organic electroluminescent device prepared by the compound of the present invention as the hole transport layer material, the organic electroluminescent device prepared by the compound of the present invention as the hole transport layer material has a lower driving voltage, high efficiency and long life.

显然，上述实施例仅仅是为清楚地说明所作的举例，而并非对实施方式的限定。对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。Apparently, the above-mentioned embodiments are only examples for clear description, rather than limiting the implementation. For those of ordinary skill in the art, other changes or changes in different forms can be made on the basis of the above description. It is not necessary and impossible to exhaustively list all the implementation manners here. And the obvious changes or changes derived therefrom are still within the scope of protection of the present invention.

Claims (9)

1. An organic light emitting compound having a structure represented by chemical formula 1:
wherein Ar is1、Ar2Each independently is a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heterocyclic group, or are combined with each other to form a ring;
Ar3hydrogen, deuterium, halogen, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other to form a ring;
r is hydrogen, deuterium, halogen, a nitrile group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylphosphino group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a ring;
l is a bond or is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
2. The organic light-emitting compound according to claim 1, wherein Ar is Ar3Selected from substituted or unsubstitutedPhenyl, biphenyl, terphenyl, naphthyl, fluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, pyrenyl, and phenanthryl.
3. The organic light-emitting compound according to claim 1, wherein Ar is Ar3One selected from phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyrenyl and phenanthryl.
4. The organic light-emitting compound according to claim 1, wherein L is one of phenyl, biphenyl, terphenyl, naphthyl, pyrenyl, phenanthrenyl, fluorenyl, spiroyl, benzofuranyl, benzothienyl, dibenzofuranyl, and dibenzothiophenyl.
5. The organic light-emitting compound of claim 1, wherein L is phenyl or biphenyl.
6. An organic light-emitting compound according to claim 1, characterized in that it is selected from any one of the following structures:
7. a method for producing an organic light-emitting compound according to any one of claims 1 to 6, comprising the steps of:
adding the raw materials A, B, palladium tetratriphenylphosphine and potassium carbonate into toluene for coupling reaction to generate an intermediate C; brominating under the action of NBS to generate an intermediate D; forming a boric acid intermediate E by the intermediate D under the action of n-butyl lithium; the intermediate E and the raw material F form a compound shown in a chemical formula 1 under the action of palladium tetratriphenylphosphine and potassium carbonate;
the synthetic route is as follows:
wherein Hal represents halogen.
8. An organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer contains the organic luminescent compound according to any one of claims 1 to 6.
9. The organic electroluminescent device of claim 8, wherein the organic light-emitting compound is used as a hole transport layer material.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111233764A (en) * 2020-03-31 2020-06-05 烟台显华化工科技有限公司 A class of organic compounds with acridine-derived triarylamine structures and their applications
CN112266353A (en) * 2020-10-20 2021-01-26 吉林奥来德光电材料股份有限公司 Aromatic anthracene organic light-emitting compound and preparation method and application thereof
CN112961131A (en) * 2021-02-04 2021-06-15 吉林奥来德光电材料股份有限公司 Organic compound, preparation method and application thereof
CN113214237A (en) * 2021-05-15 2021-08-06 吉林奥来德光电材料股份有限公司 Organic electroluminescent material and preparation method and application thereof
WO2022126362A1 (en) * 2020-12-15 2022-06-23 京东方科技集团股份有限公司 D-a type organic light emitting material and application thereof, light emitting device, light emitting substrate, and light emitting apparatus

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006151844A (en) * 2004-11-26 2006-06-15 Canon Inc Aminoanthryl-derived-group-substituted compound and organic luminescent element
US20140249606A1 (en) * 2011-05-12 2014-09-04 Merck Patent Gmbh Patents & Scientific Information Organic ionic compounds, compositions and electronic devices
JP2016181556A (en) * 2015-03-23 2016-10-13 Tdk株式会社 Compound for organic electroluminescent element and organic electroluminescent element using the same
KR20180127832A (en) * 2017-05-22 2018-11-30 머티어리얼사이언스 주식회사 Organic electroluminescent device
CN109651173A (en) * 2018-12-28 2019-04-19 武汉天马微电子有限公司 Compound, display panel and display device
CN109879811A (en) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 Organic light-emitting material, preparation method and application

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006151844A (en) * 2004-11-26 2006-06-15 Canon Inc Aminoanthryl-derived-group-substituted compound and organic luminescent element
US20140249606A1 (en) * 2011-05-12 2014-09-04 Merck Patent Gmbh Patents & Scientific Information Organic ionic compounds, compositions and electronic devices
JP2016181556A (en) * 2015-03-23 2016-10-13 Tdk株式会社 Compound for organic electroluminescent element and organic electroluminescent element using the same
KR20180127832A (en) * 2017-05-22 2018-11-30 머티어리얼사이언스 주식회사 Organic electroluminescent device
CN109651173A (en) * 2018-12-28 2019-04-19 武汉天马微电子有限公司 Compound, display panel and display device
CN109879811A (en) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 Organic light-emitting material, preparation method and application

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KOJI KUBOTA，等: "Olefin-accelerated solid-state C-N cross-coupling reactions using mechanochemistry", 《NATURE COMMUNICATIONS》 *
吕宏飞，等: "含蒽核小分子有机电致发光材料研究进展", 《化工新型材料》 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111233764A (en) * 2020-03-31 2020-06-05 烟台显华化工科技有限公司 A class of organic compounds with acridine-derived triarylamine structures and their applications
CN112266353A (en) * 2020-10-20 2021-01-26 吉林奥来德光电材料股份有限公司 Aromatic anthracene organic light-emitting compound and preparation method and application thereof
WO2022126362A1 (en) * 2020-12-15 2022-06-23 京东方科技集团股份有限公司 D-a type organic light emitting material and application thereof, light emitting device, light emitting substrate, and light emitting apparatus
CN112961131A (en) * 2021-02-04 2021-06-15 吉林奥来德光电材料股份有限公司 Organic compound, preparation method and application thereof
CN113214237A (en) * 2021-05-15 2021-08-06 吉林奥来德光电材料股份有限公司 Organic electroluminescent material and preparation method and application thereof
CN113214237B (en) * 2021-05-15 2022-05-24 吉林奥来德光电材料股份有限公司 Organic electroluminescent material and preparation method and application thereof

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