CN111995637A - 一种有机化合物及其有机电致发光器件 - Google Patents

一种有机化合物及其有机电致发光器件 Download PDF

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CN111995637A
CN111995637A CN202010939682.8A CN202010939682A CN111995637A CN 111995637 A CN111995637 A CN 111995637A CN 202010939682 A CN202010939682 A CN 202010939682A CN 111995637 A CN111995637 A CN 111995637A
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高春吉
周辉
邹丽鸿
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

本发明提供一种有机化合物及其有机电致发光器件，属于有机光电材料技术领域。本发明的有机化合物具有结构式I所示结构。
Figure DDA0002673197930000011
其中，Ar1和Ar2选自取代或未取代的C6～C30的芳基、取代或未取代的C2～C30的杂芳基中的一种；X选自O、S、Se、C(R1R2)、NR1、Si(R1R2)；R1和R2选自取代或未取代的C1～C15的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种；n是零以外的正整数。使用本发明提供的一种有机化合物制备的有机电致发光器件，具有较高的发光效率、外量子效率和较低的驱动电压。

Description

一种有机化合物及其有机电致发光器件
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种有机电致发光器件。
背景技术
本发明的技术是有机光电材料有关技术，目前有机电致发光器件中空穴传输材料(Hole Transport Layer)的代表物质如下：
Figure BDA0002673197920000011
目前要求的材料的特性是物质具备热稳定性和快速空穴移动度及发光体的高效率及长寿命，本发明是提供比现阶段性能优越的材料。
发明内容
本发明是通过非对称化合物提高空穴移动度，提供空穴传输及发光效果极大化的化合物，并且将这种咔唑衍生物制备成器件，有很好的发光效率。
本发明的技术方案如下，
本发明提供了一种有机化合物，如结构式I所示：
Figure BDA0002673197920000012
其中，Ar1和Ar2选自取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种；
X选自O、S、Se、C(R1R2)、NR1、Si(R1R2)；
n是零以外的正整数。
发本发明通过一种有机化合物可以提供性能优秀的有机电致发光器件用化合物及包括该化合物的有机电致发光器件和包括该有机电致发光器件的显示装置。
具体实施方式
下面将结合本发明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，都属于本发明的保护范围。
本发明所述烷基是指烷烃分子中少掉一个氢原子而成的烃基，其可以为直链烷基、支链烷基、环烷基，实例可包括甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、环戊基、环己基等，但不限于此。
本发明所述芳基是指芳烃分子的芳核碳上去掉一个氢原子后，剩下一价基团的总称，其可以为单环芳基或稠环芳基，实例可包括苯基、联苯基、萘基、蒽基、菲基或芘基等，但不限于此。
本发明所述杂芳基是指芳基中的一个或多个芳核碳被杂原子替代得到的基团的总称，所述杂原子包括但不限于氧、硫或氮原子，所述杂芳基可以为单环杂芳基或稠环杂芳基，实例可包括吡啶基、吡咯基、吡啶基、噻吩基、呋喃基、吲哚基、喹啉基、异喹啉基、苯并噻吩基、苯并呋喃基、二苯并呋喃基、二苯并噻吩基、咔唑基等，但不限于此。
本发明提供了一种有机电致发光器件用化合物，其分子结构通式如化学式1所示：
Figure BDA0002673197920000021
其中，Ar1和Ar2选自取代或未取代的C6～C30的芳基、取代或未取代的C2～C30的杂芳基中的一种；
X选自O、S、Se、C(R1R2)、NR1、Si(R1R2)；
n是零以外的正整数。
优选的，所述的结构式I化合物，包括下述结构式II-1～结构式II-6中任意一个表示的化合物：
Figure BDA0002673197920000031
其中，Ar1和Ar2选自取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种；
R1和R2选自取代或未取代的C1～C15的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种；
n是零以外的正整数。
优选的，权利要求1所述的一种有机化合物，其特征在于，Ar1和Ar2优先选自如下基团：
Figure BDA0002673197920000041
其中，R3选自氢、氟基(F)、氰基(CN)、取代或未取代的C1～C15的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种；
R4和R5独立的选自取代或未取代的C1～C15的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种。
进一步的优选的方式是，所述的有机化合物独立地选自下列化合物：
Figure BDA0002673197920000051
Figure BDA0002673197920000061
Figure BDA0002673197920000071
Figure BDA0002673197920000081
Figure BDA0002673197920000091
Figure BDA0002673197920000101
Figure BDA0002673197920000111
Figure BDA0002673197920000121
Figure BDA0002673197920000131
Figure BDA0002673197920000141
Figure BDA0002673197920000151
Figure BDA0002673197920000161
Figure BDA0002673197920000171
本发明还提供了一种有机电致发光器件，包括阴极层、阳极层和有机化合物层，该有机化合物层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的至少一层，其特征在于：至少一个有机化合物层包含至少一种如本发明所述的一种有机化合物。
优选的，本发明所述的有机化合物作为有机电致发光器件的空穴传输层。
本发明所述的有机电致发光器件可以在有机发光器件(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)中应用。
在本发明中，所述有机电致发光器件用化合物是单一或跟其他化合物混合物形式包括在有机物层里。
在本发明中，所述有机电致发光器件优选包括阳极、阴极以及位于阳极和阴极之间的若干个有机物层，所述“有机化合物层”指的是有机电致发光器件中阳极和阴极之间部署的全部层的术语。所述有机物层可以是具有空穴特性的层和具有电子特性的层。比如，所述有机化合物层包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输的技能层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、既具备电子传输又具备电子注入的技能层中的一种或几种。
在本发明中，所述空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输的技能层中可以采用常规的空穴注入物质、空穴传输物质、既具备空穴注入又具备空穴传输技能的物质以外再包括电子-生成的物质。
比如，所述有机化合物层是包括发光层，所述发光层是包括磷光主体、荧光主体、磷光掺杂和荧光掺杂中的一种或几种。在本发明中，可以采用所述有机电致发光器件用化合物作为荧光主体，也可以作为荧光掺杂，以及同时作为荧光主体和荧光掺杂。
在本发明中，所述发光层可以为红色、黄色或蓝色发光层。在本发明中，所述发光层为蓝色发光层时，采用上述所述的有机电致发光器件用化合物作为蓝色主体或蓝色掺杂，可得到高效率、高分辨率、高亮度及长寿命的有机电致发光器件。
制备方法和材料制备在本发明中，所述有机物层优选包括空穴传输层，所述空穴传输层包括上述技术方案所述的有机电致发光器件用化合物。
在本发明中，所述有机物层优选包括发光层和空穴传输层，所述发光层和空穴传输层均含有上述技术方案所述的有机电致发光器件用化合物，所述发光层和空穴传输层中的有机电致发光器件用化合物可以相同也可以不同。
本发明对所述有机电致发光器件的制备方法没有特殊的限制，除了使用结构式I的有机电致发光器件用化合物之外，采用本领域技术人员熟知的电致器件的得到即可。
中间体L的合成路线如下所示：
1、中间体L-1的合成
Figure BDA0002673197920000191
L-1-1的合成：
在L-1-2中加入碳酸钾和NMP，反应12个小时，用二氯甲烷和蒸馏水进行萃取，将有机化合物层分离成硅胶。通过硅胶分离残余物，得到产物L-1-1
L-1的合成：
将L-1-1和三苯基膦溶解在邻二氯苯中并回流24小时。当反应完成时
通过减压蒸馏除去溶剂后，通过柱色谱分离浓缩的产物，得到所需的L-1。
2、中间体L-2的合成
Figure BDA0002673197920000192
L-2-1的合成：
将L-2-2溶解在三氟甲磺酸中并在室温下搅拌48小时。反应终止。将该反应物倒入水和吡啶的混合溶剂中并回流20分钟。将反应温度冷却至室温，用CH2Cl 2萃取并擦去。用无水MgSO4除去少量水，减压过滤，浓缩有机溶剂使用柱色谱法分离产物，得到所需的L-2-1。
L-2的合成：
将L-2-1和三苯基膦溶解在邻二氯苯中并回流24小时。当反应完成时
通过减压蒸馏除去溶剂后，通过柱色谱分离浓缩的产物，得到所需的L-2。
3、中间体L-3的合成
Figure BDA0002673197920000201
L-3-1的合成：
将L-3-2、乙酸和磷酸混合，并将混合物在50℃下搅拌3小时。冷却到室温，将混合物用NaOH水溶液中和并用EA萃取。用硫酸镁干燥并减压蒸馏。得到产物L-3-1。
L-3的合成：
将L-3-1和三苯基膦溶解在邻二氯苯中并回流24小时。当反应完成时
通过减压蒸馏除去溶剂后，通过柱色谱分离浓缩的产物，得到所需的L-3。
实施例1：化合物1的制备
Figure BDA0002673197920000202
步骤1.将对溴碘苯(31.21g，75mmol)叔丁醇钠(21.62g，225mmol)加入到三口烧瓶中，加入甲苯(500mL)氮气置换两次，加入L-1(21.10g，75mmol)及催化剂Pd2(dba)3(2.06g,2.25mmol)，N2置换三次，注入三叔丁基膦(0.36mL，15mmol)，升温到110℃，反应1h。反应液冷却，水洗，过硅藻土除去钯催化剂，蒸干，用二氯甲烷/石油醚重结晶，得黄色固体，再用甲苯/乙酸乙酯混合溶剂45℃洗2h，抽滤，得1-1(22.91g,70％)。质谱m/z，理论值：436.30；实验值m/z：435.03。
步骤2.将1-1(32.72g，75mmol)叔丁醇钠(21.62g，225mmol)加入到三口烧瓶中，加入甲苯(500mL)氮气置换两次，加入二苯胺(12.69g，75mmol)及催化剂Pd2(dba)3(2.06g,2.25mmol)，N2置换三次，注入三叔丁基膦(0.36mL，15mmol)，升温到110℃，反应1h。反应液冷却，水洗，过硅藻土除去钯催化剂，蒸干，用二氯甲烷/石油醚重结晶，得黄色固体，再用甲苯/乙酸乙酯混合溶剂45℃洗2h，抽滤，得1(35.41g,90％)。质谱m/z，理论值：524.61，实验值m/z：524.19。
实施例2：化合物91的制备
将实施例1中的合成方法，得到化合物91。质谱m/z，理论值：600.71；实测值：600.22。
实施例3：化合物166的制备
将实施例1中的合成方法，得到化合物166。质谱m/z，理论值：650.72；实测值：650.21。
实施例4：化合物167的制备
将实施例1中的合成方法，得到化合物167。质谱m/z，理论值：666.79；实测值：666.19。
实施例5：化合物201的制备
将实施例1中的合成方法，得到化合物201。质谱m/z，理论值：746.94；实测值：746.34。
实施例6：化合物205的制备
将实施例1中的合成方法，得到化合物205。质谱m/z，理论值：742.95；实测值：742.33。
器件制备实施例：
将费希尔公司涂层厚度为
Figure BDA0002673197920000211
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透明电极上蒸镀空穴注入层HI-1/
Figure BDA0002673197920000212
空穴传输层HT-1或表1中的化合物/
Figure BDA0002673197920000213
蓝光主体BH-1,参杂材料BD-1/5％混合
Figure BDA0002673197920000214
的厚度蒸镀、空穴阻挡层及空穴传输层ET-1/
Figure BDA0002673197920000215
阴极
Figure BDA0002673197920000216
上述过程有机物蒸镀速度是保持
Figure BDA0002673197920000217
/sec、LiF是
Figure BDA0002673197920000218
/sec,Al是
Figure BDA0002673197920000219
/sec。
Figure BDA0002673197920000221
上述方法制造的有机电致发光器件的电子发光特性在表1中表示
[表1]
Figure BDA0002673197920000222
从上述表1结果中，能看出本发明的一种有机化合物应用在共同层领域里发光效率及寿命特性有显著的提高。
本发明是利用本发明的有机化合物应用在有机电致发光器件可以得到发光效率和寿命良好的结果，所以本发明是实用性高的OLED产业中有用的。本发明的有机电致发光器件是平面面板显示、平面发光体、照明用面发光OLED发光体、柔性发光体、复印机、打印机、LCD背光灯或计量机类的光源、显示板、标识等适合使用。

Claims (7)

1.一种有机化合物，其特征在于，其化合物结构通式如结构式Ⅰ所示：
Figure FDA0002673197910000011
其中，Ar1和Ar2选自取代或未取代的C6～C30的芳基、取代或未取代的C2～C30的杂芳基中的一种；
X选自O、S、Se、C(R1R2)、NR1、Si(R1R2)；
R1和R2选自取代或未取代的C1～C15的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种。
n是零以外的正整数。
2.根据权利要求1所述的一种有机化合物，所述结构I是下面结构式II-1至结构式II-6任意表示的有机电致发光器件用化合物：
Figure FDA0002673197910000012
其中，Ar1和Ar2选自取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种；
R1和R2选自取代或未取代的C1～C15的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种；
n是零以外的整数。
3.根据权利要求1所述的一种有机化合物，其特征在于，Ar1和Ar2优先选自如下基团：
Figure FDA0002673197910000021
其中，R3选自氢、氟基(F)、氰基(CN)、取代或未取代的C1～C15的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种；
R4和R5独立的选自取代或未取代的C1～C15的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C3～C30的杂芳基中的一种。
4.根据权利要求1所述的一种有机化合物，其特征在于，选自如下所示化学结构中的任意一种：
Figure FDA0002673197910000031
Figure FDA0002673197910000041
Figure FDA0002673197910000051
Figure FDA0002673197910000061
Figure FDA0002673197910000071
Figure FDA0002673197910000081
Figure FDA0002673197910000091
Figure FDA0002673197910000101
Figure FDA0002673197910000111
Figure FDA0002673197910000121
Figure FDA0002673197910000131
Figure FDA0002673197910000141
Figure FDA0002673197910000151
5.一种有机电致发光器件，包括阴极层、阳极层和有机层，该有机层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的至少一层，其特征在于：至少一个有机化合物层包含至少一种如权利要求1～4中所述的一种有机化合物。
6.根据权利要求5所述的一种有机电致发光器件，其特征在于：权利要求1～4中所述的一种有机化合物作为空穴传输材料。
7.根据权利要求5所述的有机电致发光器件在有机发光器件(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)中的应用。
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