CN111116562A - 一种有机发光化合物及其制备方法和应用 - Google Patents

一种有机发光化合物及其制备方法和应用 Download PDF

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CN111116562A
CN111116562A CN201911347719.1A CN201911347719A CN111116562A CN 111116562 A CN111116562 A CN 111116562A CN 201911347719 A CN201911347719 A CN 201911347719A CN 111116562 A CN111116562 A CN 111116562A
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马晓宇
汪康
王进政
张雪
孙毅
徐佳楠
邱镇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明提供了一种有机发光化合物及其制备方法和应用，将其用于有机电致发光器件的制备，作为其中的电子传输层，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使得器件的发光效率以及亮度提高；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。

Description

一种有机发光化合物及其制备方法和应用
技术领域
本发明涉及光电材料技术领域，特别涉及一种有机发光化合物及其制备方法和应用。
背景技术
有机发光材料是指能够以某种方式吸收能量，将其转化成光能的有机物质，它们在现代电子显示技术中具有非常重要的地位。最受科学界和产业界关注的有机发光材料是OLED(有机发光二极管，organic light-emitting diode)，它是由美籍华裔科学家邓青云博士于1979年在实验室中发现的。有机电致发光器件(OLED)作为一种新兴的平面面板显示，其具有自发光、视角宽、全固化、全彩化、反应速度快、高亮度、低驱动电压、厚度薄、质量轻、可制作大尺寸与弯曲面板等特点，近年来，OLED在显示器市场得到了越来越多的应用，成为目前最具潜力的面板显示技术。
有机电致发光器件其结构一般包括阴极、阳极及处于二者之间的有机物层，其中有机物层主要包括发光层和平衡载流子注入和传输的空穴注入层、空穴传输层、电子注入层、电子传输层等功能层。添加各功能层的目的主要是平衡从阴阳两极注入的空穴和电子，从而利于空穴和电子在发光层的复合，提高器件的激子利用率，最终提高器件的发光效率和使用寿命。
但实际应用中，各功能层的载流子传输良莠不齐，并不能有效的平衡载流子的注入，随着市场对OLED器件要求的进一步提高，更高发光效率、更长寿命、更低成本成为OLED器件发展的趋势，所以如何开发一种高电子传输性能的主体材料及电子传输材料，提高电子迁移率，促进载流子注入平衡，进而使器件发光效率更高、寿命更长是本领域技术人员亟待解决的问题。
发明内容
有鉴于此，本发明提供了一种有机发光化合物及其制备方法以及有机电致发光器件，具有较高的发光效率和寿命。
一种有机发光化合物，其特征在于，结构式如下所示：
Figure BDA0002333858100000021
其中，R为氘、卤素、酰基、羧基、硝基、羟基、胺基、三氟甲基、醚、酯、氰基、硫基、磺酰基、膦基、硅基、硼烷基或磷基中的一种，或烷基、芳烷基、烷氧基、芳氧基、硅烷基、烯基、环烯基、炔基、芳基、杂芳基中的一种以及其组合；
A和B为C6-C60的杂芳基；
m为0～4的整数，n为1～10的整数。
优选的，所述R为烷基、芳基、杂芳基、氘、卤素、三氟甲基以及其组合；所述环A和环B分别选自以下结构：
Figure BDA0002333858100000022
其中，Ar1、Ar2表示烷基、烯基、炔基、芳基、杂芳基中的一种或多种；
Figure BDA0002333858100000031
为连接位置。
优选的，所述R具体的选自以下结构：
Figure BDA0002333858100000032
优选的，所述m为1或2，所述n优选为1～4，更优选的为1或2。
优选的，所述卤素为氟、氯、溴或碘；所述烷基为直链烷基、支链烷基或环烷基；所述环烷基为单环、多环或螺烷基；所述芳基为单环芳香族烃基或多环芳香族环系统；所述杂芳基为包括至少一个杂原子的单环芳香族基团或多环芳香族环系统。
优选的，所述烷基为含有一到十五个碳原子的烷基；所述环烷基为含有3-12个环碳原子的环烷基；所述多环芳香族环系统为含有6-30个碳原子的芳基；所述杂芳基为包括O、S、N、P、B、Si或Se杂原子的碳原子数为2-30的杂环基，优选杂原子为O、S或N，更优选为N，优选的碳原子个数为3-20个，更优选为3-12个；单环杂芳香族系统优选是具有5或6个环原子的单环，并且环可以具有一到六个杂原子，杂多环系统可以具有其中两个原子为两个邻接环(所述环是“稠合的”)共用的两个或更多个环，其中所述环中的至少一个是杂芳基，例如其它环可以是环烷基、环烯基、芳基、杂环和/或杂芳基，杂多环芳香族环系统可以在多环芳香族环系统的每个环上具有一到六个杂原子。
优选的，所述烷基为甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,1-二甲基丙基、1,2-二甲基丙基或2,2-二甲基丙基；
所述环烷基为环丙基、环戊基、环己基、双环[3.1.1]庚基、螺[4.5]癸基、螺[5.5]十一烷基或金刚烷基；
所述芳基中多环可以具有其中两个碳为两个邻接环共用的两个或更多个环，其中所述环中的至少一个是芳香族烃基，例如其它环可以是环烷基、环烯基、芳基、杂芳基，此外多环芳基优选为含有6-30个碳原子的苯基、联苯、联三苯、三亚苯、四亚苯、萘、蒽、菲、芴、芘或苝；更优选为苯基、联苯、联三苯、三亚苯、芴或萘，所述的芴基可以被取代，并且两个取代基可以彼此键合以形成螺环结构，另外，芳基任选地被取代；
所述杂芳基为二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚并咔唑、吡啶并咪唑、菲啰啉、吡啶基吲哚、吡咯并二吡啶、吡唑、咪唑、三唑、噁唑、噻唑、噁二唑、噁三唑、二噁唑、噻二唑、吡啶、哒嗪、嘧啶、吡嗪、三嗪、噁嗪、噁噻嗪、噁二嗪、吲哚、苯并咪唑、吲唑、吲噁嗪、苯并噁唑、苯并异噁唑、苯并噻唑、喹啉、异喹啉、噌啉、喹唑啉、喹喔啉、萘啶、酞嗪、喋啶、氧杂蒽、吖啶、吩嗪、吩噻嗪、吩噁嗪、吡啶并吡咯、苯并呋喃并吡啶、呋喃并二吡啶、苯并噻吩并吡啶、噻吩并二吡啶、苯并硒吩并吡啶或硒吩并二吡啶；更优选为咔唑、吡啶并咪唑、吲哚并咔唑、菲啰啉、吡啶、咪唑、嘧啶、三嗪、苯并咪唑、喹啉、异喹啉、喹唑啉或喹喔啉，杂芳基任选地被取代。
上述的取代是指与化合物的碳原子键合的氢原子变成另外的取代基，并且取代的位置没有限制，只要该位置为氢原子被取代的位置(即，取代基可以取代的位置)即可，并且当两个或更多个取代基取代时，两个或更多个取代基可以彼此相同或不同；所述的取代基选自氘、卤素、酰基、羧基、硝基、羟基、胺基、三氟甲基、醚、酯、氰基、硫基、磺酰基、膦基、硅基、硼烷基或磷基；烷基、芳烷基、烷氧基、芳氧基、硅烷基、烯基、环烯基、炔基、芳基、杂芳基。
具体需要说明的是，本发明提供的有机发光化合物具体选自以下结构：
Figure BDA0002333858100000051
Figure BDA0002333858100000061
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。
本发明还提供了一种如上技术方案所述的有机发光化合物的制备方法，包括以下步骤：
步骤一：在氮气保护下，将化合物Ⅰ、化合物Ⅱ、四(三苯基膦)钯和碳酸钾按摩尔比60：72:0.7:180的比例加入到体积比为3:1:1的甲苯/乙醇/水的混合溶剂中，升温至回流，反应结束后冷却至室温，加入水洗涤、过滤、干燥，将干燥产物置于1,4-二氧六环中重结晶，得到中间体化合物；
步骤二：在氮气保护下，将步骤一中得到的中间体与化合物Ⅲ、四(三苯基膦)钯和碳酸钾按摩尔比45:54:0.45:180的比例加入到体积比为3:1:1的甲苯/乙醇/水的混合溶剂中，升温至回流，反应结束后冷却至室温，加入水洗涤、过滤、干燥，将干燥产物置于1,4-二氧六环中重结晶，得到有机发光化合物；
具体反应如下所示：
Figure BDA0002333858100000071
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。
经由上述方案，相较于现有技术，本发明具有如下有益效果：
本发明提供了一种新型结构的有机发光化合物，将其用于有机电致发光器件的制备，作为其中的电子传输层，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使得器件的发光效率以及亮度提高；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。
具体实施方式
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。
实施例1
中间体化合物的制备：
氮气保护下，将化合物Ⅰ-2(60.0mmol)、化合物Ⅱ-2(72mmol)、碳酸钾(180.0mmol)加入到400mL甲苯/乙醇/水(体积比3:1:1)的混合溶剂中，加入四(三苯基磷)钯(0.7mmol)，升温至回流，待反应结束后，冷却至室温，加入水洗涤、过滤、滤饼干燥，置于1,4-二氧六环中重结晶，得中间体C-2(21.3g，收率83％)，反应式如下：
Figure BDA0002333858100000081
采用上述中间体的制备方法分别制备以下中间体，具体原料及生成物和收率等如下表1所示；
表1.
Figure BDA0002333858100000082
Figure BDA0002333858100000091
有机发光化合物的制备：
采用上述制备的中间体化合物制备有机发光化合物，具体如下：
氮气保护下，将中间体C-2(45.0mmol)、化合物Ⅲ-2(54mmol)、碳酸钾(180.0mmol)加入到400mL甲苯/乙醇/水(体积比3:1:1)的混合溶剂中，之后加入四(三苯基磷)钯(0.45mmol)，升温至回流，待反应结束后，冷却至室温，加入水洗涤、过滤、滤饼干燥，置于1,4-二氧六环中重结晶，得有机发光化合物2(25.7g，收率81％)；具体反应式如下：
Figure BDA0002333858100000101
采用上述有机发光化合物2的制备方法分别制备以下有机发光化合物，具体原料及生成物和收率等如下表2所示；
表2.
Figure BDA0002333858100000102
Figure BDA0002333858100000111
Figure BDA0002333858100000121
试验例1
采用上述实施例1制得的有机发光化合物2制备有机电致发光器件并进行性能评价，具体制备方法如下：
将涂层厚度为
Figure BDA0002333858100000122
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；
首先在ITO(阳极)上面蒸镀厚度20nm的N1-(2-萘基)-N4，N4-二(4-(2-萘基(苯基)氨基)苯基)-N1-苯基苯-1，4-二胺2-TNAT)，紧接着蒸镀厚度100nm的[二-[4-(N,N-二甲苯基-氨基)-苯基]环己烷(TAPC)以及厚度20nm的重量比97:3的主体物质4，4'-N，N'-联苯二咔唑CBP)和掺杂物质化合物Ir(ppy)3混合层，之后蒸镀厚度35nm的有机发光化合物2作为电子传输层，然后蒸镀厚度1.5nm的LiF作为电子注入层，最后蒸镀厚度为15nm镁和银(质量比1:10)作为阴极，制备得到有机电致发光器件2；对得到的器件的性能发光特性测试。
之后采用上述制备方法，不同之处在于将有机发光化合物分别替换为有机发光化合物15、有机发光化合物22、有机发光化合物38、有机发光化合物49、有机发光化合物59、有机发光化合物86、有机发光化合物92、有机发光化合物96、有机发光化合物97、有机发光化合物99、有机发光化合物100制备得到有机电致发光器件15、有机电致发光器件22、有机电致发光器件38、有机电致发光器件49、有机电致发光器件59、有机电致发光器件86、有机电致发光器件92、有机电致发光器件96、有机电致发光器件97、有机电致发光器件99、有机电致发光器件100。
对比例1
按照器件试验例1的方法制备器件，不同之处在于将有机发光化合物2替换为具有以下结构式的Alq3：
Figure BDA0002333858100000131
之后该器件进行性能测试。
试验例1和对比例1中所制得得有机电致发光器件的性能测试方法为：
对有机电致发光器件加以正向直流偏置电压，利用Photo Research公司的PR-650光度测量设备测定有机电致发光特性，并在5000cd/m2的基准灰度下利用McScience公司的寿命测定装置测定了器件寿命，测试结果见表3；
表3.机电致发光器件检测结果
Figure BDA0002333858100000132
Figure BDA0002333858100000141
从上述表3结果中可以看出，使用本发明提供的化合物作为电子传输层所制备的有机电致发光器件，与使用比较例化合物Alq3作为电子传输层所制备的有机电致发光器件相比，驱动电压明显降低，发光效率以及寿命得到显著提高。
本说明书中各个实施例采用递进的方式描述，每个实施例重点说明的都是与其他实施例的不同之处，各个实施例之间相同相似部分互相参见即可。对于实施例公开的装置而言，由于其与实施例公开的方法相对应，所以描述的比较简单，相关之处参见方法部分说明即可。
对所公开的实施例的上述说明，使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的，本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下，在其它实施例中实现。因此，本发明将不会被限制于本文所示的这些实施例，而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。

Claims (10)

1.一种有机发光化合物，其特征在于，结构式如下所示：
Figure FDA0002333858090000011
其中，R为氘、卤素、酰基、羧基、硝基、羟基、胺基、三氟甲基、醚、酯、氰基、硫基、磺酰基、膦基、硅基、硼烷基或磷基中的一种，或烷基、芳烷基、烷氧基、芳氧基、硅烷基、烯基、环烯基、炔基、芳基、杂芳基中的一种以及其组合；
A和B为C6-C60的杂芳基；
m为0～4的整数，n为1～10的整数。
2.根据权利要求1所述的一种有机发光化合物，其特征在于，所述R为烷基、芳基、杂芳基、氘、卤素、三氟甲基以及其组合；所述环A和环B分别选自以下结构：
Figure FDA0002333858090000012
其中，Ar1、Ar2表示烷基、烯基、炔基、芳基、杂芳基中的一种或多种；
Figure FDA0002333858090000021
为连接位置。
3.根据权利要求2所述的一种有机发光化合物，其特征在于，所述R具体的选自以下结构：
Figure FDA0002333858090000022
4.根据权利要求1所述的一种有机发光化合物，其特征在于，所述m为1或2，所述n为1或2。
5.根据权利要求1-4任一项所述的一种有机发光化合物，其特征在于，所述卤素为氟、氯、溴或碘；所述烷基为直链烷基、支链烷基或环烷基；所述环烷基为单环、多环或螺烷基；所述芳基为单环芳香族烃基或多环芳香族环系统；所述杂芳基为包括至少一个杂原子的单环芳香族基团或多环芳香族环系统。
6.根据权利要求5所述的一种有机发光化合物，其特征在于，所述烷基为含有一到十五个碳原子的烷基；所述环烷基为含有3-12个环碳原子的环烷基；所述多环芳香族环系统为含有六到三十个碳原子的芳基；所述杂芳基为包括O、S、N、P、B、Si或Se杂原子的碳原子数为2-30的杂环基。
7.根据权利要求6所述的一种有机发光化合物，其特征在于，所述烷基为甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,1-二甲基丙基、1,2-二甲基丙基或2,2-二甲基丙基；所述环烷基为环丙基、环戊基、环己基、双环[3.1.1]庚基、螺[4.5]癸基、螺[5.5]十一烷基或金刚烷基；所述芳基为苯基、联苯、联三苯、三亚苯、四亚苯、萘、蒽、菲、芴、芘或苝；所述杂芳基为二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚并咔唑、吡啶并咪唑、菲啰啉、吡啶基吲哚、吡咯并二吡啶、吡唑、咪唑、三唑、噁唑、噻唑、噁二唑、噁三唑、二噁唑、噻二唑、吡啶、哒嗪、嘧啶、吡嗪、三嗪、噁嗪、噁噻嗪、噁二嗪、吲哚、苯并咪唑、吲唑、吲噁嗪、苯并噁唑、苯并异噁唑、苯并噻唑、喹啉、异喹啉、噌啉、喹唑啉、喹喔啉、萘啶、酞嗪、喋啶、氧杂蒽、吖啶、吩嗪、吩噻嗪、吩噁嗪、吡啶并吡咯、苯并呋喃并吡啶、呋喃并二吡啶、苯并噻吩并吡啶、噻吩并二吡啶、苯并硒吩并吡啶或硒吩并二吡啶。
8.根据权利要求7所述的一种有机发光化合物，其特征在于，所述芳基为苯基、联苯、联三苯、三亚苯、芴或萘，所述杂芳基为咔唑、吡啶并咪唑、吲哚并咔唑、菲啰啉、吡啶、咪唑、嘧啶、三嗪、苯并咪唑、喹啉、异喹啉、喹唑啉或喹喔啉。
9.一种权利要求1-8任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：
步骤一：在氮气保护下，将化合物Ⅰ、化合物Ⅱ、四(三苯基膦)钯和碳酸钾按摩尔比60：72:0.7:180的比例加入到体积比为3:1:1的甲苯/乙醇/水的混合溶剂中，升温至回流，反应结束后冷却至室温，加入水洗涤、过滤、干燥，将干燥产物置于1,4-二氧六环中重结晶，得到中间体化合物；
步骤二：在氮气保护下，将步骤一中得到的中间体与化合物Ⅲ、四(三苯基膦)钯和碳酸钾按摩尔比45:54:0.45:180的比例加入到体积比为3:1:1的甲苯/乙醇/水的混合溶剂中，升温至回流，反应结束后冷却至室温，加入水洗涤、过滤、干燥，将干燥产物置于1,4-二氧六环中重结晶，得到有机发光化合物；
具体反应如下所示：
Figure FDA0002333858090000041
10.一种权利要求1-8所述的有机发光化合物在有机电致发光器件中的应用。
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