CN109748913B - 基于咔唑及吡啶构建单元的电致发光材料 - Google Patents

基于咔唑及吡啶构建单元的电致发光材料 Download PDF

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CN109748913B
CN109748913B CN201711061710.5A CN201711061710A CN109748913B CN 109748913 B CN109748913 B CN 109748913B CN 201711061710 A CN201711061710 A CN 201711061710A CN 109748913 B CN109748913 B CN 109748913B
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李慧杨
戴雷
蔡丽菲
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Abstract

本发明涉及基于咔唑及吡啶构建单元的电致发光材料，具有式(I)所述的结构，其中，R1、R2独立选自氢，C1‑C4取代或未取代的烷基，C2‑C4取代或者未取代的烯烷基，C2‑C4取代或者未取代的炔烷基，C6‑C10的含有一个或者多个取代基取代或未取代的芳基、芳烃基，C3‑C8的含有一个或者多个取代基取代或未取代的含有一个或者多个杂原子的杂芳基。实验结果表明，本发明的电致发光材料应用于OLED中，具有较高的发光效率，有潜力应用于有机电致发光器件领域。

Description

基于咔唑及吡啶构建单元的电致发光材料
技术领域
本发明涉及新型有机发光二极管电致发光材料，特别是涉及一种基于咔唑及吡啶构建单元的电致发光材料，通过真空沉积成薄膜，作为发光层材料用于有机发光二极管器件。
背景技术
近年来，有机发光二极管(OLED)作为一种有巨大应用前景的照明、显示技术，受到了学术界与产业界的广泛关注。OLED器件具有自发光、广视角、反应时间短及可制备柔性器件等特性，成为下一代显示、照明技术的有力竞争者。但目前OLED仍然存在效率低、寿命短等问题，有待人们进一步研究。
有机发光二极管为电致发光器件，在电压驱动下，电子和空穴分别经电子传输层和空穴传输层进入发光层复合形成激子。之后，激子将能量传递给有发光特性的有机分子，使其受激发，激发态分子回到基态时发生辐射跃迁而发光。自1998年Forrest等人报道电致磷光器件(PHOLED)以来，PHOLED因其可以高效利用三线态和单线态激子发光而备受关注。高效PHOLED器件通常为多层结构，其优点在于可以方便地调节载流子注入、传输及复合等过程。在发光层中，当客体掺杂浓度较高时，会出现浓度淬灭和T1-T1湮灭，导致发光效率降低。为了解决这些问题，通常将客体材料掺杂在主体材料中，从而“稀释”客体材料的浓度。主体中形成的激子通过
Figure BDA0001454922740000011
和Dexter能量转移的方式传递给客体，受激发的客体辐射发光回到基态。因此，为了获得高效PHOLED器件，开发新型高性能的主体材料尤为重要。
主体材料可以分为空穴型、电子型和双极型三种类型。当使用空穴型主体材料时，空穴、电子复合通常发生在发光层和电子传输层界面上；当使用电子型主体材料时，空穴、电子复合通常发生在发光层和空穴传输层界面上。可见，单极型主体材料易于导致载流子复合区域变窄。窄的复合区域会导致局部激子密度升高而加速T1-T1湮灭，不利于器件性能的提升。而双极型主体材料则可以有效地解决上述问题。使用双极型主体材料，既可以平衡器件中的空穴和电子、拓宽载流子复合区域，又可以简化器件结构，引起了该领域研究者的极大兴趣。
发明内容
本发明目的在于提供一种新型基于吡啶和咔唑构建单元的双极型主体材料，将该材料以用于有机发光二极管器件，获得了很好的发光效率。
基于咔唑及吡啶构建单元的电致发光材料，具有化学式(I)的结构：
Figure BDA0001454922740000021
Ar为下列基团中的一个：
Figure BDA0001454922740000022
其中，R1、R2独立选自氢，C1-C4取代或未取代的烷基，C2-C4取代或者未取代的烯烷基，C2-C4取代或者未取代的炔烷基，C6-C10的含有一个或者多个取代基取代或未取代的芳基、芳烃基，C3-C8的含有一个或者多个取代基取代或未取代的含有一个或者多个杂原子的杂芳基；所述取代为被卤元素、C1－C4的烷基所取代。
优选地，R1、R2独立选自氢，C1-C4烷基，C6-C10的含有一个或者多个取代或未取代的芳基、芳烃基；
更优选地，R1、R2独立选自氢，甲基，叔丁基，苯基，甲苯基，萘基；
进一步优选，R1、R2为相同取代基，选自氢，叔丁基，苯基，甲基；
特别优选，其中Ar为下列基团：
Figure BDA0001454922740000023
R1、R2为相同取代基，选自氢，叔丁基，苯基。
进一步优选，其中Ar为下列基团之一：
Figure BDA0001454922740000024
特别优选：R1为氢，R2为叔丁基，苯基，甲苯基，萘基。
有机电致发光二极管器件，包括阴极、阳极和有机层，所述有机层为空穴传输层、发光层、空穴阻挡层、电子传输层中的一层或多层，这些有机层不必每层都存在。
所述空穴传输层、空穴阻挡层、发光层和/或电子传输层中含有式(I)所述的化合物。
所述式(I)所述的化合物为应用于发光层中的主体材料。
本发明的器件有机层的总厚度为1-1000nm，优选1-500nm，更优选5-300nm。
所述有机层可以通过蒸渡或溶液法形成薄膜。
如上面提到的，本发明的式(I)所述的化合物如下，但不限于所列举的结构：
Figure BDA0001454922740000031
Figure BDA0001454922740000041
再优选：式(I)所表示化合物为以下结构
Figure BDA0001454922740000042
Figure BDA0001454922740000051
上述化合物在有机电致发光器件，力致发光器件，有机场效应晶体管，有机太阳能电池和化学传感器上的应用。
实验结果表明，本发明的有机主体材料应用于OLED中，具有较高的发光效率，有潜力应用于有机电致发光器件领域。
附图说明
图1为本发明的有机电致发光器件结构图，
其中10代表为玻璃基板，20代表为阳极，30代表为空穴注入层，40代表为空穴传输层，50代表发光层，60代表空穴阻挡层，70代表电子注入层，80代表为阴极。
具体实施方式
为了更详细叙述本发明，特举以下例子，但是不限于此。
实施例1
化合物1的合成路线
Figure BDA0001454922740000052
化合物1的合成
氮气保护下，将化合物a(3.2g,9.5mmol)(参考文献J.Heterocycl.Chem.,2016,53,615-619合成)、化合物1a(3.0g,10.5mmol)(参考文献J.Mater.Chem.C,2015,3,12529-12538合成)、Pd(PPh3)4(208mg,0.2mmol)、二氧六环(40mL)和碳酸钾水溶液(2M,5mL)依次加入Schlenk管中。加热至80℃，反应12小时。冷至室温后，将上述反应液加入水中，经二氯甲烷萃取三次，合并有机相。有机相经无水硫酸钠干燥后，旋除溶剂，剩余物经柱层析分离得浅黄色固体(5.4g,产率85％),升华后纯度为99.8％。MS(EI):m/z:662.5(M+)
实施例2
化合物2的合成路线
Figure BDA0001454922740000061
化合物2的合成
氮气保护下，将化合物a(2.2g,6.5mmol)、化合物2a(2.3g,8.0mmol)(参考文献J.Mater.Chem.C,2015,3,12529-12538合成)、Pd(PPh3)4(208mg,0.2mmol)、二氧六环(40mL)和碳酸钾水溶液(2M,5mL)依次加入Schlenk管中。加热至80℃，反应12小时。冷至室温后，将上述反应液加入水中，经二氯甲烷萃取三次，合并有机相。有机相经无水硫酸钠干燥后，旋除溶剂，剩余物经柱层析分离得浅黄色固体(3.1g,产率72％),升华后纯度为99.8％。MS(EI):m/z:662.5(M+)
实施例3
化合物3的合成路线
Figure BDA0001454922740000062
化合物3的合成
氮气保护下，将化合物a(3.2g,9.5mmol)、化合物3a(3.0g,10.5mmol)(参考文献J.Mater.Chem.C,2015,3,12529-12538合成)、Pd(PPh3)4(208mg,0.2mmol)、二氧六环(40mL)和碳酸钾水溶液(2M,5mL)依次加入Schlenk管中。加热至80℃，反应12小时。冷至室温后，将上述反应液加入水中，经二氯甲烷萃取三次，合并有机相。有机相经无水硫酸钠干燥后，旋除溶剂，剩余物经柱层析分离得浅黄色固体(3.4g,产率54％),升华后纯度为99.8％。MS(EI):m/z:662.2(M+)
实施例4
化合物12的合成路线
Figure BDA0001454922740000071
化合物12的合成
氮气保护下，将化合物a(1.2g,3.6mmol)、化合物12a(1.1g,3.83mmol)(参考文献CN105601613A合成)、Pd(PPh3)4(50mg,0.04mmol)、二氧六环(20mL)和碳酸钾水溶液(2M,5mL)依次加入Schlenk管中。加热至80℃，反应12小时。冷至室温后，将上述反应液加入水中，经二氯甲烷萃取三次，合并有机相。有机相经无水硫酸钠干燥后，旋除溶剂，剩余物经柱层析分离得浅黄色固体(2.4g,产率83％),升华后纯度为99.7％。MS(EI):m/z:814.5(M+).
实施例5
有机电致发光器件1的制备
使用本发明的有机主体材料制备OLED，见图1
首先，将透明导电ITO玻璃基板10(上面带有阳极20)依次经：洗涤剂溶液和去离子水，乙醇，丙酮，去离子水洗净，再用氧等离子处理30秒。
然后，在ITO上蒸渡10nm厚的HATCN作为空穴注入层30。
然后，蒸渡化合物TAPC,形成40nm厚的空穴传输层40。
然后，在空穴传输层上蒸渡30nm厚的AG-Pt-1(10％)、TCTA(60％)与化合物1(30％)作为发光层50。
然后，在发光层上蒸渡50nm厚的TmPyPb作为空穴阻挡层60。
最后，蒸渡1nm LiF为电子注入层70和100nm Al作为器件阴极80。
器件中所述结构式
Figure BDA0001454922740000081
所制备的器件在20mA/cm2的工作电流密度下，亮度为9060cd/m2,电流效率为45.3cd/A发射绿光。使用本发明的有机材料制备的器件具有很好的电致发光性能，符合高性能OLED器件对主体材料的要求。

Claims (10)

1.基于咔唑及吡啶构建单元的电致发光材料，具有化学式(I)的结构：
Figure FDA0002985876860000011
Ar为下列基团：
Figure FDA0002985876860000012
其中，R1、R2独立选自氢，C1-C4未取代的烷基，C6-C10未取代的芳基；
或者Ar为下列基团：
Figure FDA0002985876860000013
其中，R1为氢，R2为C6-C10未取代的芳基。
2.根据权利要求1所述的电致发光材料，Ar为下列基团：
Figure FDA0002985876860000014
其中R1、R2独立选自氢，C1-C4烷基，C6-C10未取代的芳基。
3.根据权利要求2所述的电致发光材料，其中R1、R2独立选自氢，甲基，叔丁基，苯基，萘基。
4.根据权利要求3所述的电致发光材料，其中R1、R2为相同取代基，选自氢，叔丁基，苯基，甲基。
5.根据权利要求4所述的电致发光材料，其中Ar为下列基团：
Figure FDA0002985876860000015
其中R1、R2为相同取代基，选自氢，叔丁基，苯基。
6.根据权利要求1所述的电致发光材料，其中Ar为下列基团之一：
Figure FDA0002985876860000021
7.根据权利要求6所述的电致发光材料，R1为氢，R2为苯基，萘基。
8.根据权利要求1所述的电致发光材料，所述式(I)的结构为下列化合物结构中的一个：
Figure FDA0002985876860000022
Figure FDA0002985876860000031
Figure FDA0002985876860000041
9.根据权利要求8所述的电致发光材料，所述式(I)的结构为下列化合物结构之一：
Figure FDA0002985876860000042
10.权利要求1-9任一材料在有机电致发光器件，力致发光器件，有机场效应晶体管，有机太阳能电池和化学传感器上的应用。
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