CN111434648B - 一类用于制作有机电致发光器件的化合物及其应用 - Google Patents

一类用于制作有机电致发光器件的化合物及其应用 Download PDF

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CN111434648B
CN111434648B CN201910028891.4A CN201910028891A CN111434648B CN 111434648 B CN111434648 B CN 111434648B CN 201910028891 A CN201910028891 A CN 201910028891A CN 111434648 B CN111434648 B CN 111434648B
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CN111434648A (zh
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吴建德
丰佩川
孙伟
陈义丽
单鸿斌
魏鹏
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Yantai Xianhua Chem Tech Co ltd
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Abstract

本发明属于有机光电材料技术领域，尤其涉及一类用于制作有机电致发光器件的化合物及其应用。本发明制得的化合物不仅传输效率高，且具有高的热和光稳定性。该类材料在OLED显示器领域，可用作空穴注入材料、空穴传输材料和包覆材料，也可应用于光伏电池、有机场效应管、荧光传感或激光等有机电子领域。

Description

一类用于制作有机电致发光器件的化合物及其应用
技术领域
本发明属于有机光电材料技术领域，尤其涉及一类用于制作有机电致发光器件的化合物及其应用。
背景技术
有机发光二极管(英文名Organic Light Emitting Diode，简称OLED)是一种由有机材料薄膜组成的固态器件，施加电压后能够发光。相比于传统的发光二极管(LED)和液晶显示(LCD)，OLED具有自发光、清晰亮丽、轻薄、响应速度快、视角宽、低功耗、适用温度范围大、制造工艺简单等特点。OLED可做成像壁纸般随处折、卷、贴、挂的梦幻显示器，有望将取代液晶显示，被誉为“终极显示技术”。此外，OLED作为平面光源，无论是在结构上还是在光源质量、产品特色等方面都具有传统LED照明无法企及的优势。
发明内容
本发明针对上述现有技术存在的不足，提供一类用于制作有机电致发光器件的化合物及其应用。
本发明解决上述技术问题的技术方案如下：一类用于制作有机电致发光器件的化合物，其结构式如下：
其中，X1、X2、X3、X4、X5各自独立地为CR或N；
m≥1，且m为整数；
R1、R2各自独立地为如下结构：
R为氢、氘、烷基、环烷基、羟基、巯基、烯基、炔基、取代或未取代的芳基、取代或未取代的杂芳基、烷氧基、芳氧基、胺基、酰胺基、硅烷基、卤素、CN、SCN、NO2或CF3。
优选地，上述化合物，其结构式如下：
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本发明的第二个目的在于提供上述化合物作为电致发光材料，在有机电致发光器件中的应用。
一种有机电致发光器件，包括阳极层、阴极层和位于阳极层、阴极层之间的功能层，所述功能层中包含上述化合物，所述功能层是指空穴传输层；上述化合物作为空穴传输材料。
本发明提供的有机物具有良好的热稳定性和光稳定性，可以包覆在有机电致发光元件的阴极层外，或者阳极层外，用于保护阴或阳极，从而增强器件的光热稳定性。
本发明的有益效果是：本发明的化合物作为空穴传输材料，传输效率高，具有高的热和光稳定性。该类材料在OLED显示器领域，可用作空穴注入材料、空穴传输材料及有机被覆材料，亦可用于光伏电池、有机场效应管、荧光传感或激光等有机电子领域。
附图说明
图1为有机电致发光材料的OLED结构示意图；
图中，1、玻璃衬底；2、阳极层；3、空穴注入层；4、空穴传输层；5、发光层；6、电子传输层；7、电子注入层；8、阴极层。
具体实施方式
以下对本发明的原理和特征进行描述，所举实例只用于解释本发明，并非用于限定本发明的范围。
一、化合物的合成实施例
实施例1
化合物8的合成，反应方程式如下：
(1)合成中间体
(2)目标物合成
具体反应过程如下：
(1)将2-溴-9,9’-螺双芴(MW：394)39.4g(0.1mol)、(1,1’-联苯)-2-胺(MW:169.1)17.75g(0.105mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管,温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N-(〔1,1’-联苯〕-2-基)-9,9’-螺双芴-2-胺(MW:483.2)45.9g(0.095mol)，收率95％；
(2)将N-(〔1,1’-联苯〕-2-基)-9,9’-螺双芴-2-胺(MW:483.2)45.9g(0.095mol)、4-(4-溴苯基)吗啡啉(MW:241)23.86g(0.099mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯、350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温,加入140mL乙醇，再过滤，水洗，烘干，得到N-(〔1,1’-聯苯基〕-2基)-N-(4-吗啡啉苯基)-(9,9’-螺双芴)-2-胺基(MW:644.3)57.34g(0.089mole)，收率93.6％。
实施例2
化合物9的合成，反应方程式如下：
(1)合成中间体
(2)目标物合成
具体反应过程如下：
(1)将2-溴-9,9’-螺双芴(MW:394)39.4g(0.1mol)、(1,1’-联苯)-2-胺(MW:169.1)17.75g(0.105mol)、醋酸钯(II))(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N-(〔1,1’-联苯〕-2-基)-9,9’-螺双芴-2-胺(MW:483.2)45.9g(0.095mol)，收率95％；
(2)将N-(〔1,1’-联苯〕-2-基)-9,9’-螺双芴-2-胺(MW:483.2)45.9g(0.095mol)、4-(4’-溴〔1,1’-聯苯基〕-4-基)吗啡啉(MW:317)31.38g(0.099mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管,温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N-(〔1,1’-聯苯基〕-2基)-N-(4-吗啡啉-〔1,1’-聯苯基〕-4-基)-(9,9’-螺双芴)-2-胺基,(MW:720.3)62.95g(0.0874mol)，收率93％。
实施例3
化合物18的合成，反应方程式如下：
(1)合成中间体
(2)目标物合成
具体反应过程如下：
(1)将2-溴-9,9’-螺双芴(MW:394)39.4g(0.1mol)、(1,1’-联苯)-2-胺(MW:169.1)17.75g(0.105mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N(9,9-二甲基-9H-芴-2-基)-9,9’-螺双芴-2-胺(MW:523.2)49.18g(0.094mol)，收率94％；
(2)将N(9,9-二甲基-9H-芴-2-基)-9,9’-螺双芴-2-胺(MW:523.2)49.18g(0.094mol)、4-(4-溴苯基)吗啡啉(MW:241)23.86g(0.099mol)、醋酸钯(II))(分子量224.51)0.22g、三叔丁基磷)(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N-(9,9’-二甲基-9-氢-芴-2基)-N-(4-吗啡啉苯基)-(9,9’-螺双芴)-2-胺基(MW:684.3)59.82g(0.08742mol)，收率93％。
实施例4
化合物19的合成，反应方程式如下：
(1)合成中间体
(2)目标物合成
具体反应过程如下：
(1)将2-溴-9,9’-螺双芴(MW:394)39.4g(0.1mol)、(1,1’-联苯)-2-胺(MW:169.1)17.75g(0.105mol)、醋酸钯(II))(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N(9,9-二甲基-9H-芴-2-基)-9,9’-螺双芴-2-胺(MW:523.2)48.65g(0.093mol)，收率94％；
(2)将N(9,9-二甲基-9H-芴-2-基)-9,9’-螺双芴-2-胺(MW:523.2)48.65g(0.093mol)、4-(4’-溴〔1,1’-聯苯基〕-4-基)吗啡啉(MW:317)31.38g(0.099mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷)(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N-(9,9’-二甲基-9-氢-芴-2基)-N-(4’-吗啡啉基-〔1,1’-聯苯基〕-4-基)-(9,9’-螺双芴)-2-胺基(MW:760.3)66.46g(0.08742mol)，收率93％。
实施例5
化合物83的合成，反应方程式如下：
(1)合成中间体
(2)目标物合成
具体反应过程如下：
(1)将2-溴-9,9’-螺双芴(MW:394)39.4g(0.1mol)、3-(9氢-咔唑-9基)苯胺(MW:258.1)27.1g(0.105mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠)(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管,温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N-(3-(9氢-咔唑-9基)苯基)-9,9’-螺双芴-2-胺(MW:572.2)53.78g(0.094mol)，收率94％；
(2)将N-(3-(9氢-咔唑-9基)苯基)-9,9’-螺双芴-2-胺(MW:572.2)53.78g(0.094mol)、4-(4-溴苯基)吗啡啉(MW:241)23.86g(0.099mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N(3-(9氢-咔唑-9基)苯基)-N(4-吗啡啉苯基)-9,9’-螺双芴-2-胺基(MW:733.3)64.1g(0.08742mol)，收率93％。
实施例6
化合物84的合成，反应方程式如下：
(1)合成中间体
(2)目标物合成
具体反应过程如下：
(1)将2-溴-9,9’-螺双芴(MW:394)39.4g(0.1mol)、3-(9氢-咔唑-9基)苯胺(MW:258.1)27.1g(0.105mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N-(3-(9氢-咔唑-9基)苯基)-9,9’-螺双芴-2-胺(MW:572.2)53.78g(0.094mol)，收率94％；
(2)将N-(3-(9氢-咔唑-9基)苯基)-9,9’-螺双芴-2-胺(MW:572.2)53.78g(0.094mol)、4-(4’-溴〔1,1’-聯苯基〕-4-基)吗啡啉(MW:317)31.38g(0.099mol)、醋酸钯(II)(分子量224.51)0.22g、三叔丁基磷(MW:202.32)0.44g(0.0022mol)、甲苯350mL和叔丁醇钠(MW:96.10)11.5g，置于500mL反应瓶中，插冷凝管，温度计搅拌反应，升温到110℃，反应12hrs，待反应结束后降温，加入140mL乙醇，再过滤，水洗，烘干，得到N(3-(9氢-咔唑-9基)苯基)-N(4-吗啡啉-〔1,1’-聯苯〕-4基)-9,9’-螺双芴-2-胺基(MW:809.3)67.98g(0.084mol)，收率92％。
二、有机电致发光器件应用例
应用例中用到的化合物的结构如下：
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应用例1的有机电致发光器件的制备过程如下：
(1)在玻璃底衬1上沉积一层厚度为100nm的氧化铟锡(ITO)作为透明阳极层2；
(2)在透明阳极层2上真空蒸镀厚度为10nm的NPB(N,N’-二(1-萘基)-N,N’-二苯基-1,1’-联苯-4-4’-二胺)空穴传输材料作为空穴注入层3，其中掺杂质量比3％的F4-TCNQ(2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌)；
(3)空穴注入层3上为一层厚度为100nm的化合物8作为空穴传输层4；
(4)在空穴传输层4上真空蒸镀一层厚度为20nm的蓝色荧光主体CBP(4,4'-二(9-咔唑)联苯)作为发光层作为发光层5，其中掺杂有3wt％的蓝色荧光参杂物TMTP(1,3,6,8-四间甲苯芘)；
(5)再在发光层5上依次真空蒸镀一层厚度为30nm的TPQ(2,3,5,8-四苯基喹喔啉)作为电子传输层6；
(6)在电子传输层上真空蒸镀厚度为1nm的LiF作为电子注入层7；
(7)在电子注入层7上采用真空蒸镀膜沉积技术沉积厚度为100nm的金属铝(Al)作为器件的阴极层8；
(8)最后在阴极层8上蒸镀厚度为30nm的TBBD，包覆在阴极层上。
经性能测试获知，该器件的电致发光光谱的最大发光波长位于490nm，颜色为蓝色，最大外量子效率为6％；电流密度10mA/m2条件下，T95寿命达到380小时。
应用例2
与应用例1相同，与应用例1不同之处在于：空穴传输层4为厚度100nm的化合物9作为空穴传输层4。
经性能测试获知，该器件的电致发光光谱的最大发光波长位于490nm，颜色为蓝色，最大外量子效率为6％；电流密度10mA/m2条件下，T95寿命达到395小时。
应用例3
与应用例1相同，与应用例1不同之处在于：空穴传输层4为厚度100nm的化合物18作为空穴传输层4。
经性能测试获知，该器件的电致发光光谱的最大发光波长位于490nm，颜色为蓝色，最大外量子效率为5％；电流密度10mA/m2条件下，T95寿命达到385小时。
应用例4
与应用例1相同，与应用例1不同之处在于：空穴传输层4为厚度100nm的化合物19作为空穴传输层4。
经性能测试获知，该器件的电致发光光谱的最大发光波长位于490nm，颜色为蓝色，最大外量子效率为7％；电流密度10mA/m2条件下，T95寿命达到405小时。
应用例5
与应用例1相同，与应用例1不同之处在于：空穴传输层4为厚度100nm的化合物83作为空穴传输层4。
经性能测试获知，该器件的电致发光光谱的最大发光波长位于490nm，颜色为蓝色，最大外量子效率为5％；电流密度10mA/m2条件下，T95寿命达到370小时。
应用例6
与应用例1相同，与应用例1不同之处在于：空穴传输层4为厚度100nm的化合物84作为空穴传输层4。
经性能测试获知，该器件的电致发光光谱的最大发光波长位于490nm，颜色为蓝色，最大外量子效率为6％；电流密度10mA/m2条件下，T95寿命达到395小时。
对比例1
与应用例1相同，与应用例1不同之处在于：空穴传输层4为厚度100nm的spiro-TAD(2,2',7,7'-四(二苯基氨基)-9,9'-螺双芴)作为空穴传输层4。
经性能测试获知，该器件的电致发光光谱的最大发光波长位于490nm，颜色为蓝色，最大外量子效率为5％；电流密度10mA/m2条件下，T95寿命达到320小时。
对比例2
与对比例1相同，与对比例1不同之处在于阴极外的包覆层为化合物19。
经性能测试获知，器件性能与对比例1相当，但器件的T95寿命达到360小时。表明本发明提供的有机材料作为包覆层，能够很好的保护有机电致发光器件。
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (4)

1.一类用于制作有机电致发光器件的化合物，其特征在于，其结构式如下：
。
2.一种有机电致发光器件，包括阳极层、阴极层和位于阳极层、阴极层之间的功能层，其特征在于，所述功能层中包含权利要求1所述的化合物。
3.根据权利要求2所述的有机电致发光器件，其特征在于，所述功能层是指空穴传输层；权利要求1所述的化合物作为空穴传输材料。
4.一种有机包覆材料，其特征在于，权利要求1所述的化合物用于包覆有机电致发光器件原件的阴极层或阳极层。
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