WO2020073479A1 - 有机发光化合物及其制备方法和含该化合物的有机电致发光器件 - Google Patents

有机发光化合物及其制备方法和含该化合物的有机电致发光器件 Download PDF

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WO2020073479A1
WO2020073479A1 PCT/CN2018/120962 CN2018120962W WO2020073479A1 WO 2020073479 A1 WO2020073479 A1 WO 2020073479A1 CN 2018120962 W CN2018120962 W CN 2018120962W WO 2020073479 A1 WO2020073479 A1 WO 2020073479A1
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emitting
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王辉
马晓宇
李文军
王进政
汪康
李贺
毕岩
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吉林奥来德光电材料股份有限公司
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Definitions

  • the present application relates to the technical field of organic light-emitting materials, in particular to an organic light-emitting compound, a preparation method thereof, and an organic electroluminescent device containing the compound.
  • organic electroluminescent device also known as an organic light-emitting diode (OLED)
  • OLED organic light-emitting diode
  • LED light-emitting diode Due to the advantages of low voltage operation, high brightness, light weight, wide viewing angle, and high contrast value, organic electroluminescent devices have been gradually used in flat panel displays in recent years.
  • an organic electroluminescent display includes an organic light emitting diode pixel array that has self-luminous characteristics, so no external backlight is required.
  • the organic light emitting diode assembly includes a pair of electrodes, and an organic light emitting medium layer between the electrodes.
  • the object of the present application includes, for example, providing an organic light-emitting compound, a preparation method thereof, and an organic electroluminescent device containing the compound.
  • the organic light-emitting compound of the present application is a combination of acridine-based functional groups with high electron hole transport efficiency and triarylamines with excellent hole transport performance to form a class of compounds with high thermal stability and excellent light-emitting efficiency.
  • the present disclosure provides an organic light-emitting compound, the general structure of which is shown in formula (I):
  • R 1 is selected from any of the following structures:
  • R 2 is selected from any of the following structures:
  • Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C14-C17 aryl groups.
  • Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C12-C13 aryl groups.
  • the organic light-emitting compound is any one of the following structures:
  • the present disclosure also provides a method for preparing an organic light-emitting compound, including the following steps:
  • the present application also provides an application of the compound of formula (I) described in the present application in the preparation of an organic electroluminescent device;
  • the organic layer includes at least a hole injection layer, a hole transport layer, a layer with both hole injection and hole transport skills, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer And one or more of the layers with both electronic transmission and electronic injection skills.
  • At least one of the hole injection layer, the hole transport layer, and the layer having both hole injection and hole transport skills is a conventional hole injection substance, a hole transport substance, or both It also has a hole transport skill substance, and may also be a substance generated by an electron transport substance.
  • the compound of formula (I) when the compound of formula (I) is present in the light-emitting layer of the organic layer, the compound of formula (I) may be used as a light-emitting host or doped in other fluorescent hosts; for example: the light-emitting layer may It is a red, yellow or blue light-emitting layer. Doping the compound of formula (I) on the blue host can provide the efficiency, brightness, resolution and long life of the resulting light-emitting device.
  • the electron transport layer When a compound of the structure of formula (I) is present in the electron transport layer, the electron transport layer also includes a metal-containing compound.
  • the compound of formula (I) may exist in one or two layers.
  • the organic light emitting device is an organic light emitting diode (OLED).
  • the device prepared by the compound containing the structure of formula (I) described in this application can be used for organic light emitting device (OLED), organic solar cell (OSC), electronic paper (e-Paper), organic photoreceptor (OPC) or organic Thin film transistor (OTFT).
  • OLED organic light emitting device
  • OSC organic solar cell
  • e-Paper electronic paper
  • OPC organic photoreceptor
  • OTFT organic Thin film transistor
  • the device described in this application can be deposited on the substrate by thin-film evaporation, electron beam evaporation, physical vapor deposition and other methods to form an anode on the substrate and conductive oxides and their alloys, can also use spin coating (spin- coating) or thin strip lead evaporation; tape-casting, doctor-blading, screen-printing, ink-jet printing or thermal-imaging methods can also be used Reduce the number of layers to manufacture.
  • the organic light-emitting device is a flat panel display.
  • the present application proposes an organic luminescent compound, which is a combination of acridine functional groups with high electron hole transport efficiency and triarylamines with excellent hole transport performance to form a class of thermally stable
  • the compound with high performance and excellent luminous efficiency, the introduction of different substituents can change the electronic transition, so that the luminescence peak position can be adjusted, and the device made of the material of the present application can meet the needs of industrial production.
  • the preparation method of the organic luminescent compound provided by the present application has a simple preparation method, which is suitable for industrial production, and by adjusting the ratio of the reactants, and the reaction time and temperature, a compound with better performance can be prepared.
  • the organic electroluminescent device provided by the present application has excellent luminous efficiency, brightness, resolution, and long life.
  • V-2 to V-4 The synthesis method of the products shown in V-2 to V-4 is similar to that of V-1.

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Abstract

涉及有机发光材料技术领域，具体提供一种有机发光化合物及其制备方法和含该化合物的有机电致发光器件，该有机发光化合物是将吖啶类官能基与三芳基胺类组合，具备空穴传输性能。

Description

有机发光化合物及其制备方法和含该化合物的有机电致发光器件
相关申请的交叉引用
本申请要求于2018年10月11日提交中国国家知识产权局的申请号为201811180993.X、名称为“有机发光化合物及其制备方法和含该化合物的有机电致发光器件”的中国专利申请的优先权，其全部内容通过引用结合在本申请中。
技术领域
本申请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含该化合物的有机电致发光器件。
背景技术
有机电致发光装置(organic electroluminescent device)，也称作有机发光二极管(organic light-emitting diode；OLED)，是以有机层作为主动层的一种发光二极管(LED)。由于有机电致发光装置具有低电压操作、高亮度、重量轻、广视角、以及高对比值等优点，近年来已渐渐使用于平面面板显示器(flat panel display)上。与液晶显示器不同，有机电致发光显示器所包含的有机发光二极管象素数组是具有自发光的特性，因此不需外加背光源。一般而言，有机发光二极管组件包括一对电极，以及在电极之间的一有机发光介质层。在外加电场的作用下，电子和空穴分别从阴极和阳极向夹在电极之间的有机发光介质层注入，注入的电子和空穴分别从电子传输层和空穴传输层向发光层迁移，电子和空穴在有机发光介质层中相遇产生激子(excitons)，激子在有机发光介质层中不断地作自由扩散运动，并以辐射或无辐射的方式失活，当激子由激发态以辐射跃迁的方式回到基态，就可以观察到电致发光现象，发射光的颜色由激发态到基态的能级差所决定。
依据空穴和电子的自旋态(spin state)，由空穴和电子的再结合而产生的激子可具有三重态(triplet)或单重态(singlet)的自旋态。由单重态激子(singlet exciton)所产生的发光为荧光(fluorescence)，而由三重态激子(triplet exciton)所产生的发光为磷光(phosphorescence)。磷光的发光效率是荧光的三倍。因此，发展高效率的磷光材料以增进有机发光二极管组件的发光效率是非常重要的。
发明内容
本申请的目的包括例如提供一种有机发光化合物及其制备方法和含该化合物的有机电致发光器件。本申请的有机发光化合物是将具有高电子空穴传输效率的吖啶类官能基与空穴传输性能优异的三芳胺类组合，形成了一类热稳定性能高，发光效率优异的化合物。
本公开提供了一种有机发光化合物，其结构通式如式(Ⅰ)所示：
Figure PCTCN2018120962-appb-000001
式中：R 1选自下述结构中的任意一个：
Figure PCTCN2018120962-appb-000002
其中“*”指代与N原子相连接的位置；
式中：R 2选自下述结构中的任意一个：
Figure PCTCN2018120962-appb-000003
其中“*”指代与苯环相连接的位置；
L为苯基或氢；
Ar 1和Ar 2各自独立地选自取代或未取代的C6-C25的芳基、或者取代或未取代的C12-C22的杂芳基。
在一种或多种实施方式中，Ar 1和Ar 2各自独立地选自取代或未取代的C10-C21的芳基、或者取代或未取代的C16-C18的杂芳基。
在一种或多种实施方式中，Ar 1和Ar 2各自独立地选自取代或未取代的C14-C17的芳基。
在一种或多种实施方式中，Ar 1和Ar 2各自独立地选自取代或未取代的C12-C13的芳基。
在一种或多种实施方式中，所述有机发光化合物为下述结构中的任意一个：
Figure PCTCN2018120962-appb-000004
Figure PCTCN2018120962-appb-000005
Figure PCTCN2018120962-appb-000006
Figure PCTCN2018120962-appb-000007
Figure PCTCN2018120962-appb-000008
Figure PCTCN2018120962-appb-000009
本公开还提供了一种有机发光化合物的制备方法，包括以下步骤：
(1)将具有式(II)所示结构的化合物分别与式(III)或式(IV)所示结构的化合物反应，得到式(V)或式(VI)所示结构的化合物；
(2)将式(V)或式(VI)所示结构的化合物分别与式(VII)所示结构的化合物反应，得到式(I)所示结构的化合物；
Figure PCTCN2018120962-appb-000010
在一种或多种实施方式中，所述式(II)所示结构的化合物由下述方法制备：
式(A)所示结构的化合物和式(C)所示结构的化合物反应生成式(B)所示结构的化合物，式(B)所示结构的化合物再与R 2的格氏试剂反应生成式(II)所示结构的化合物；
Figure PCTCN2018120962-appb-000011
其中，式(C)中X 1和X 2独立地选自卤素，且不同时为同一种卤素；X为X 1或X 2。
按照本申请，本申请将具有式(II)所示结构的化合物与式(III)或式(IV)所示结构的化合物反应，得到式(V)或式(VI)所示结构的化合物，其中，R 1和R 2基团的选择与前述相同；所述式(II)所示结构的化合物与式(III)或式(IV)所示结构的化合物的摩尔比为1：(0.9～1.6)；所述反应的催化剂优选为四三苯基膦钯；所述反应的碱为碳酸钠；所述反应的温度优选为130～180℃，更优选为150～160℃；所述反应的时间优选为20～40小时，更优选为24～30小时。
本申请对式(II)所示结构的化合物与式(III)或式(IV)所示结构的化合物的来源没有特殊限定，通过本领域公知的制备方法制得即可。
按照本申请，本申请将式(V)或式(VI)所示结构的化合物分别与式(VII)所示结构的化合物反应，得到式(I)所示结构的化合物；其中，R 1和R 2基团的选择与前述相同；所述式(V)或式(VI)所示结构的化合物与式(VII)所示结构的化合物的摩尔比为1：(0.9～1.6)；所述反应中所用碱为叔丁醇钠，所述反应的催化剂为乙酸钯和三叔丁基膦；所述反应的温度优选为130～180℃，更优选为150～160℃；所述反应的时间优选为20～40小时，更优选为24～30小时。
按照本申请，本申请将具有式(A)所示结构的化合物与式(C)所示结构的化合物反应，得到式(B)所示结构的化合物；所述式(A)所示结构的化合物与式(C)所示结构的化合物的摩尔比为(0.9～1.6)：1；所述反应的催化剂优选为醋酸钯；所述反应的碱为叔丁醇钠；所述反应的温度优选为130～180℃，更优选为150～160℃；所述反应的时间优选为20～40小时，更优选为24～30小时。
按照本申请，本申请将具有式(B)所示结构的化合物与R 2的格氏试剂反应，得到式(II)所示结构的化合物，其中，R 2基团的选择与前述相同；所述式(B)所示结构的化合物与R 2的格氏试剂的摩尔比为1：(1～3)；所述反应的温度优选为0℃～5℃；更优选为0℃；所述反应的时间优选为0.5～4小时，更优选为1～3小时。
本申请还提供了一种本申请所述的式(I)结构的化合物在制备有机电致发光器件中的应用；
具体的，所述有机电致发光器件优选为，包括：
第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含有式(I)所示结构的化合物；式(I)所示结构的化合物可以是单一形态或与其它物质混合存在于有机物层中。
其中，所述有机物层至少包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层，电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
所述空穴注入层、所述空穴传输层、所述既具备空穴注入又具备空穴传输技能层中至少有一个是常规的空穴注入物质、空穴传输物质或者既具备空穴注入又具备空穴传输技能物质，也有可能是电子传输物质生成的物质。
本申请中“有机物层”指的是有机电子器件第一电极和第二电极之间部署的全部层的术语。
具体的，当式(I)结构的化合物存在于所述有机物层中的发光层时，所述式(I)结构的化合物可以作为发光主体或者掺杂在其它荧光主体中；例如：发光层可以是红色、黄色或蓝色发光层。而将式(I)结构的化合物掺杂在蓝色主体上，可以提供得到的发光器件的效率、亮度、分辨率及长寿命。
当式(I)结构的化合物存在于电子传输层时，所述电子传输层还包括含有金属的化合物。
所述有机物层包括发光层以及电子传输层时，所述式(I)结构的化合物可以存在于其中一层或两层。
在一种或多种实施方式中，有机发光器件为有机发光二极管(OLED)。
本申请所述的包含有式(I)结构的化合物制备的器件可以用于有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-Paper)、有机感光体(OPC)或有机薄膜晶体管(OTFT)。
本申请所述的器件可以通过薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属及具有导电性的氧化物及他们的合金形成阳极，也可以采用旋转涂膜(spin-coating)或薄带带头蒸镀；还可以采用成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等方法减少层数制造。
本申请还提供了一种有机发光装置，包括多个上述的有机电致发光器件。
在一种或多种实施方式中，有机发光装置为平面面板显示器。
本申请的有益效果是：
与现有技术相比，本申请提出一种有机发光化合物，其是将具有高电子空穴传输效率的吖啶类官能基与空穴传输性能优异的三芳胺类组合，形成了一类热稳定性能高，发光效率优异的化合物，不同取代基的引入，能改变电子跃迁，使其发光峰位可以调节，用本申请的材料制作成的器件能够满足工业化生产的需求。
本申请提供的有机发光化合物的制备方法，其制法简单，适于工业化生产，并且通过调节反应物用量比，及反应时间和温度可以制备得到性能更优异的化合物。
本申请提供的有机电致发光器件，其具有优异的发光效率、亮度、分辨率，并且寿命长。
具体实施方式
下面将结合本申请实施例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申请一部分实施例，而不是全部的实施例。基于本申请中的实施例，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，都属于本申请保护的范围。
中间体式(B)结构化合物的制备
Figure PCTCN2018120962-appb-000012
取100mL三口瓶，分别放入20.0mmol起始原料(A)、1-溴-4-碘苯(C)24.0mmol、碘化亚铜1.0mmol、邻菲罗啉4mmol、碳酸铯40mmol，脱气三次，确保整体反应处于氮气系统，加入无水甲苯溶剂30mL，并且将反应瓶上的回流管回流冷凝，反应4小时后，使用TLC片确定反应结束，降至室温，过滤，并用二氯甲烷过滤清洗，收集滤液，旋转蒸发得到微黄色液体，柱层析，使用正己烷/乙酸乙酯＝9:1为洗脱液，进行纯化分离，最终可得产物B-1，产率约85％。
中间体式(II)结构化合物的制备
Figure PCTCN2018120962-appb-000013
取100mL三口瓶，放入10.0mmol化合物B-1，脱气三次，确保整体反应处于氮气系统，加入无水THF溶剂20mL，之后将反应瓶置于0℃的冷井中，待整体系统温度达到平衡后，使用针头吸取12.0mmol联苯基溴化镁，慢慢滴加到反应瓶内，维持低温反应1小时后，让整体反应由0℃慢慢反应至室温。在室温下反应两个小时后，经TLC确认反应终点。加20mL饱和氯化铵水溶液进行淬灭，分液，浓缩。将得到中间体不经纯化直接加入到100mL三口瓶中，加入30mL甲苯溶剂和20mmol的甲磺酸，加热到回流，反应3小时，让整体反应降温至室温。经TLC确认反应终点。将反应液滴加到150mL水溶液中，抽滤，烘干。将得到固体使用柱层析进行纯化，使用石油醚/乙酸乙酯＝1:1为洗脱液，进行纯化分离，最终可得产物II-1，产率约78％。
式(II-2)～式(II-6)的合成方法与式(II-1)的合成方法类似，其合成的原料以及产物和收率见表1；
表1
Figure PCTCN2018120962-appb-000014
Figure PCTCN2018120962-appb-000015
中间体(V)和(VI)的制备
Figure PCTCN2018120962-appb-000016
在氮气保护体系下，加入10.0mmol中间体II-1与12.0mmol中间体III-1，加入碳酸钠25mmol和溶剂30mL，溶剂为甲苯和水，比例为2:1，对反应体系脱气，加入催化剂四三苯基膦钯0.2mmol，将反应体系的温度升至回流，反应24小时，使用石油醚：二氯甲烷＝2:1重结晶，得到中间体V-1，产率为75％。
Figure PCTCN2018120962-appb-000017
在氮气保护体系下，加入10.0mmol中间体II-1与12.0mmol中间体IV-1，加入叔丁醇钠30mmol和溶剂30mL，溶剂为无水甲苯。对反应体系脱气，加入催化剂三(二亚苄基丙酮)二钯0.1mmol，三(叔丁基)膦1mmol将反应体系的温度升至回流，反应12小时。反应结束后加入超纯水搅拌，抽滤，乙醇和超纯水淋洗，烘干后得VI-1。
V-2～V-4所示产物的合成方法与V-1的合成方法类似。
VI-2～VI-13所示产物的合成方法与VI-1的合成方法类似。
其合成的原料以及产物和收率见表2。
表2
Figure PCTCN2018120962-appb-000018
Figure PCTCN2018120962-appb-000019
Figure PCTCN2018120962-appb-000020
目标产物式(I)结构化合物的制备
实施例1
Figure PCTCN2018120962-appb-000021
在氮气保护体系下，加入10mmL中间体VI-1与12mmL中间体VII-1，加入叔丁醇钠30mmol和溶剂30mL，溶剂为无水甲苯。对反应体系脱气，加入0.1mmol催化剂三(二亚苄基丙酮)二钯，1mmol三(叔丁基)膦将反应体系的温度升至回流，反应12小时。反应结束后加入超纯水搅拌，抽滤，乙醇和超纯水淋洗，烘干后得化合物21，质谱值为625.32。
将上述实施例中的中间体VI-1替换为中间体V-1，制备得到化合物1。
其它化合物的合成方法与化合物1的合成方法类似，其合成的原料以及产物和收率见表3。
表3
Figure PCTCN2018120962-appb-000022
Figure PCTCN2018120962-appb-000023
Figure PCTCN2018120962-appb-000024
用实施例1的制备方法，替换结构式(1)中R 1、R 2、Ar 1、Ar 2、L取代基可以得到不同的目标产物，这里就不一一列举。
应当理解的是，本申请的应用不限于上述的举例，对本领域普通技术人员来说，可以根据上述说明加以改进或变 换，所有这些改进和变换都应属于本申请所附权利要求的保护范围。
对得到的式(I)所示化合物进行性能测试
将涂层厚度为
Figure PCTCN2018120962-appb-000025
的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥，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。将已经准备好的ITO透明电极上蒸镀厚度为50nm的4，4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)作为空穴注入层。然后将上述制备的化合物1、6、13、19、21、33、38、50、64、71、72、73、75、77、81、84、90、a-NPD或对比例样品在形成的空穴注入层上面真空蒸镀厚度为30nm的空穴传输层。然后在上述空穴传输层上蒸镀厚度为30nm的蓝色主体材料9，10-二(2-萘基)蒽(ADN)和掺杂材料N1，N1，N6，N6-四苯基芘-1，6-二胺(TPPDA)。主体材料和掺杂材料的重量比为95:5。接着在上述发光层上真空蒸镀厚度为40nm的TPBi作为空穴阻挡层及电子传输层。在上述电子传输层上真空蒸镀厚度为0.5nm氟化锂(LiF)，作为电子注入层。最后蒸镀厚度为150nm的铝作为阴极，以此完成了有机电致发光器件的制备。对得到的器件的性能发光特性测试，测量采用KEITHLEY吉时利2400型源测量单元，CS-2000分光辐射亮度计，以评价驱动电压，发光亮度，发光效率，发光颜色。结果见表4，表4为本申请实施例制备的化合物以及a-NPD制备的发光器件的发光特性测试结果。
Figure PCTCN2018120962-appb-000026
对比例样品
表4为本申请实施例制备的化合物以及a-NPD制备的发光器件的发光特性测试结果。
表4
Figure PCTCN2018120962-appb-000027
Figure PCTCN2018120962-appb-000028
从表4可知，由本申请提供的有机发光化合物作为空穴传输层制备的有机电致发光器件的发光效率及寿命相对于由a-NPD及对比例样品分别作为空穴传输层制备的有机电致发光器件有显著的提高。
以上实施例的说明只是用于帮助理解本申请的方法及其核心思想。应当指出，对于本技术领域的普通技术人员来说，在不脱离本申请原理的前提下，还可以对本申请进行若干改进和修饰，这些改进和修饰也落入本申请权利要求的保护范围内。
工业实用性：
本申请的有机发光化合物是一类热稳定性能高，发光效率优异的化合物，不同取代基的引入，能改变电子跃迁，使其发光峰位可以调节，用本申请的材料制作成的器件能够满足工业化生产的需求。本申请的有机发光化合物的制备方法简单，适于工业化生产，并且通过调节反应物用量比，及反应时间和温度可以制备得到性能更优异的化合物。本申请的有机电致发光器件具有优异的发光效率、亮度、分辨率，并且寿命长。

Claims (20)

  1. 一种有机发光化合物，其特征在于，其结构通式如式(Ⅰ)所示：
    Figure PCTCN2018120962-appb-100001
    式中：R 1选自下述结构中的任意一个：
    Figure PCTCN2018120962-appb-100002
    其中“*”指代与N原子相连接的位置；
    式中：R 2选自下述结构中的任意一个：
    Figure PCTCN2018120962-appb-100003
    其中“*”指代与苯环相连接的位置；
    L为苯基或氢；
    Ar 1和Ar 2各自独立地选自取代或未取代的C6-C25的芳基、或者取代或未取代的C12-C22的杂芳基。
  2. 根据权利要求1所述的有机发光化合物，其特征在于，Ar 1和Ar 2各自独立地选自取代或未取代的C10-C21的芳基、或者取代或未取代的C16-C18的杂芳基。
  3. 根据权利要求1所述的有机发光化合物，其特征在于，Ar 1和Ar 2各自独立地选自取代或未取代的C14-C17的芳基。
  4. 根据权利要求1所述的有机发光化合物，其特征在于，Ar 1和Ar 2各自独立地选自取代或未取代的C12-C13的芳基。
  5. 根据权利要求1所述的有机发光化合物，其特征在于，所述有机发光化合物为下述结构中的任意一个：
    Figure PCTCN2018120962-appb-100004
    Figure PCTCN2018120962-appb-100005
    Figure PCTCN2018120962-appb-100006
    Figure PCTCN2018120962-appb-100007
    Figure PCTCN2018120962-appb-100008
    Figure PCTCN2018120962-appb-100009
  6. 一种权利要求1-5任意一项所述的有机发光化合物的制备方法，其特征在于，包括以下步骤：
    (1)将具有式(II)所示结构的化合物分别与式(III)或式(IV)所示结构的化合物反应，得到式(V)或式(VI)所示结构的化合物；
    (2)将式(V)或式(VI)所示结构的化合物分别与式(VII)所示结构的化合物反应，得到式(I)所示结构的化合物；
    Figure PCTCN2018120962-appb-100010
  7. 根据权利要求6所述的有机发光化合物的制备方法，其特征在于，式(II)所示结构的化合物由下述方法制备：
    式(A)所示结构的化合物和式(C)所示结构的化合物反应生成式(B)所示结构的化合物，式(B)所示结构的化合物再与R 2的格氏试剂反应生成式(II)所示结构的化合物；
    Figure PCTCN2018120962-appb-100011
    其中，式(C)中X 1和X 2独立地选自卤素，且不同时为同一种卤素；X为X 1或X 2。
  8. 根据权利要求6所述的有机发光化合物的制备方法，其特征在于，
    步骤(1)中：所述式(II)所示结构的化合物与式(III)或式(IV)所示结构的化合物的摩尔比为1：(0.9～1.6)；所述反应的催化剂优选为四三苯基膦钯；所述反应的碱为碳酸钠；所述反应的温度为130～180℃；所述反应的时间为20～40小时；
    步骤(2)中：所述式(V)或式(VI)所示结构的化合物与式(VII)所示结构的化合物的摩尔比为1：(0.9～1.6)；所述反应所用碱为叔丁醇钠，所述反应的催化剂为乙酸钯和三叔丁基膦；所述反应的温度为130～180℃；所述反应的时间为20～40小时。
  9. 根据权利要求6所述的有机发光化合物的制备方法，其特征在于，
    步骤(1)所述反应的温度为150～160℃，所述反应的时间为24～30小时；
    步骤(2)所述反应的温度为150～160℃，所述反应的时间为24～30小时。
  10. 根据权利要求7所述的有机发光化合物的制备方法，其特征在于，
    所述式(A)所示结构的化合物与式(C)所示结构的化合物的摩尔比为(0.9～1.6)：1；所述反应的催化剂优选为醋酸钯；所述反应的碱为叔丁醇钠；所述反应的温度优选为130～180℃，更优选为150～160℃；所述反应的时间优选为20～40小时，更优选为24～30小时。
  11. 根据权利要求7所述的有机发光化合物的制备方法，其特征在于，
    所述式(B)所示结构的化合物与R 2的格氏试剂的摩尔比为1：(1～3)；所述反应的温度优选为0℃～5℃；更优选为0℃；所述反应的时间优选为0.5～4小时，更优选为1～3小时。
  12. 一种有机电致发光器件，包括第一电极、第二电极和置于所述两电极之间的有机物层，其特征在于，所述有机物层中包含权利要求1-5任意一项所述的式(I)所示结构的化合物，所述式(I)所示结构的化合物是单一形态或与其它物质混合存在于有机物层中。
  13. 根据权利要求16所述的有机电致发光器件，其特征在于，所述有机物层至少包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层，电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
  14. 根据权利要求12所述的有机电致发光器件，其特征在于，所述有机物层至少包括发光层，所述式(I)所示结构的化合物存在于所述发光层中。
  15. 根据权利要求14所述的有机电致发光器件，其特征在于，所述式(I)所示结构的化合物作为发光主体或者以掺杂在其它荧光主体的形式存在于所述发光层中。
  16. 根据权利要求12所述的有机电致发光器件，其特征在于，所述有机物层至少包括电子传输层，所述式(I)所示结构的化合物存在于所述电子传输层，所述电子传输层还包括含有金属的化合物。
  17. 根据权利要求12所述的有机电致发光器件，其特征在于，所述有机物层至少包括发光层和电子传输层，所述式(I)结构的化合物存在于所述发光层和所述电子传输层中的一层或两层中。
  18. 根据权利要求1至5任一项所述有机发光化合物在制备有机电致发光器件中的应用。
  19. 一种有机发光装置，包括多个根据权利要求12-18任一项所述的有机电致发光器件。
  20. 根据权利要求19所述的有机发光装置，其中所述有机发光装置为平面面板显示器。
PCT/CN2018/120962 2018-10-11 2018-12-13 有机发光化合物及其制备方法和含该化合物的有机电致发光器件 WO2020073479A1 (zh)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130118269A (ko) * 2012-04-19 2013-10-29 에스에프씨 주식회사 방향족 화합물 및 이를 포함하는 유기전계발광소자
CN105111143A (zh) * 2015-08-15 2015-12-02 吉林奥来德光电材料股份有限公司 一种性能优良的有机发光材料及其制备方法
CN105153031A (zh) * 2015-08-15 2015-12-16 吉林奥来德光电材料股份有限公司 一种新颖的有机电致发光材料及其制备方法和应用
US20160099421A1 (en) * 2014-10-01 2016-04-07 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
CN108912102A (zh) * 2018-07-27 2018-11-30 吉林奥来德光电材料股份有限公司 一种芳胺衍生物、其制备方法与应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130118269A (ko) * 2012-04-19 2013-10-29 에스에프씨 주식회사 방향족 화합물 및 이를 포함하는 유기전계발광소자
US20160099421A1 (en) * 2014-10-01 2016-04-07 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same
CN105111143A (zh) * 2015-08-15 2015-12-02 吉林奥来德光电材料股份有限公司 一种性能优良的有机发光材料及其制备方法
CN105153031A (zh) * 2015-08-15 2015-12-16 吉林奥来德光电材料股份有限公司 一种新颖的有机电致发光材料及其制备方法和应用
CN108912102A (zh) * 2018-07-27 2018-11-30 吉林奥来德光电材料股份有限公司 一种芳胺衍生物、其制备方法与应用

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