CN115141106B - 化合物、有机材料和有机光电器件 - Google Patents

化合物、有机材料和有机光电器件 Download PDF

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CN115141106B
CN115141106B CN202210757960.7A CN202210757960A CN115141106B CN 115141106 B CN115141106 B CN 115141106B CN 202210757960 A CN202210757960 A CN 202210757960A CN 115141106 B CN115141106 B CN 115141106B
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CN115141106A (zh
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王鹏
王湘成
赵顺峰
何睦
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Shandong Yaoyi Material Technology Co ltd
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Abstract

本发明公开了化合物、有机材料和有机光电器件，该化合物具有如式(1)所示的化学结构，Ar1‑Ar4选自取代或未取代的C6‑C30芳基或C5‑C30杂芳基，至少一个含有吸电子基团；L1和L2选自单键、取代或未取代的C6‑C30芳基或C5‑C30杂芳基；A选自取代或未取代的直链或支链的C1‑C30烷基、C1‑C30杂烷基、C3‑C30环烷基或C3‑C30杂环烷基。本发明的化合物以烷基为中心结构，同时连接对称的双胺结构，在芳环或杂芳环上引入如三氟甲基、氰基和硝基等强吸电子基团，具有较低的折射率和紫外吸收性能，作为覆盖层材料用于有机光电器件可以提升器件的发光效率、色纯度和使用寿命。

Description

化合物、有机材料和有机光电器件
技术领域
本发明属于有机光电材料领域，具体涉及用于改善有机光电器件的发光效率和色纯度的化合物、有机材料和有机光电器件，适用于有机EL显示器、照明光源、标示板和标识灯。
背景技术
有机电致发光(Organic Light Emission Diode)器件具有高亮度、材料选择范围宽、驱动电压低和全固化主动发光等特性，同时拥有高清晰、广视角以及可顺畅显示动画的高速响应等优势，是最近十几年热门研究领域。由于OLED的外量子效率与内量子效率之间存在巨大差距，极大地制约其发展，如何提高OLED的光取出效率成为研究热点。ITO薄膜和玻璃衬底的界面以及玻璃衬底和空气的界面处会发生全反射，出射到OLED器件前向外部空间的光约占有机材料薄膜EL总量的20％，其余约80％的光主要以导波形式限制在有机材料薄膜、ITO薄膜和玻璃衬底中，可见常规OLED器件的出光效率较低(约为20％)，严重制约OLED的发展和应用。如何减少OLED器件的全反射效应、提高光耦合到器件前向外部空间的比例(出光效率)引起人们的广泛关注。目前，实现提高OLED外量子效率的一类重要方法是在基底出光表面形成如褶皱、光子晶体、微透镜阵列和添加表面覆盖层等结构，前两种结构会影响OLED的辐射光谱角度分布，第三种结构制作工艺复杂，而使用表面覆盖层工艺简单，发光效率提高30％以上，为人们所关注。
现有技术中，使用具有高折射率的特定结构的芳香胺衍生物或使用符合特定参数要求的材料作为有机覆盖层材料来改善光取出效率和色纯度，但尚未解决兼顾发光效率和色纯度的问题，特别是制备蓝光发光元件的情况。为解决这些问题，双覆盖层结构被提出并取得一些成果，其原理是在高折射率材料层和发光层之间增加一层低折射率层形成第二共振腔，从而提高发光效率并解决色纯度的问题。另外，现有的器件中LiF不可折叠，在柔性体系中不适用，势必需要用有机化合物替代刚性的LiF，但是LiF具有较低的折射率，所以替代的有机化合物必须具有较低的折射率，通常选择长链烷烃，但是长链烷烃在高温下容易分解，不利于器件制作。此外也有选用咪唑、苯并咪唑、咔唑等衍生物作为低折射率材料，但是这些化合物的折射率约为1.7，不能解决上述问题。
发明内容
为了解决上述问题，本发明提供一种以烷基为中心结构的化合物，适用于双覆盖层有机光电器件，提高有机光电器件的光取出效率以及改善色纯度。
本发明的第一方面提供一种化合物，其具有如式(1)所示的化学结构：
式(1)中，Ar1-Ar4相同或不相同，独立选自取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基，且Ar1-Ar4中至少一个含有选自氰基、硝基、三氟甲基、羧基、含氟基团、叔丁基或异丙基的取代基团；
L1和L2相同或不相同，独立选自单键、取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基；
A选自取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、硅原子数为1-30的硅烷基团、亚砜基或磷氧基基团。
本发明的另一方面提供一种有机光电器件，其包含前述化合物作为其覆盖层材料。
本发明的再一方面提供一种显示或照明装置，包括所述有机光电器件。
与现有技术相比，本发明的化合物以烷基为中心结构，同时连接对称的双胺结构，而且在芳环或杂芳环上引入如三氟甲基、氰基和硝基等强吸电子基团，使所形成的化合物具有较低的折射率、具备有一定的紫外吸收，作为双覆盖层材料用于有机光电器件可以提升器件的发光效率、色纯度和使用寿命。
具体实施方式
以下详细说明具体公开的化合物及其在有机光电器件中的应用的实施方式。本领域技术人员可由本说明书所揭露的内容轻易地了解本发明的其他优点与功效。本发明还可以通过另外不同的具体实施方式加以实施或应用，本说明书中的各项细节也可以基于不同观点与应用，在没有背离本发明的精神下进行各种修饰或改变。
在进一步描述本发明具体实施方式之前，应理解，本发明的保护范围不局限于下述特定的具体实施方案；还应当理解，本发明实施例中使用的术语是为了描述特定的具体实施方案，而不是为了限制本发明的保护范围；在本发明说明书和权利要求书中，除非文中另外明确指出，单数形式“一个”、“一”和“这个”包括复数形式。
当实施例给出数值范围时，应理解，除非本发明另有说明，每个数值范围的两个端点以及两个端点之间任何一个数值均可选用。除非另外定义，本发明中使用的所有技术和科学术语与本技术领域技术人员通常理解的意义相同。除实施例中使用的具体方法、设备、材料外，根据本技术领域的技术人员对现有技术的掌握及本发明的记载，还可以使用与本发明实施例中所述的方法、设备、材料相似或等同的现有技术的任何方法、设备和材料来实现本发明。
本发明的发明人经过大量探索研究，提供一种以烷基为中心结构的化合物应用到有机光电器件，使器件具备有较高的发光效率，分子具有高的稳定性进一步提升器件的发光效率和使用寿命，在此基础上完成本发明。
本发明中的取代基的实例描述如下，但取代基并不限于此：
【取代或未取代】是指经选自以下的一个或多个取代基取代：氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基团、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基膦基、杂芳基、苊基，或未取代；或者经连接以上示例的取代基中两个或多个取代基的取代基取代，或未取代；例如“连接两个或多个取代基的取代基”可包括联苯基，即联苯基可为芳基或者为连接两个苯基的取代基。
【烷基】可为直链或支链的，并且碳原子数没有特别限制。在一些实施例中，烷基包括但不限于甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、4-甲基己基、5-甲基己基。
以上对烷基的描述也可用于芳烷基、芳烷基胺基、烷基芳基和烷基胺基中的烷基。
【杂烷基】可为含杂原子的直链或支链的烷基，并且碳原子数没有特别限制。在一些实施例中，杂烷基包括但不限于可以烷氧基、烷硫基、烷基磺酰基等。烷氧基例如可以包括但不限于甲氧基、乙氧基、正丙氧基、异丙氧基(isopropoxy)、异丙氧基(i-propyloxy)、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁氧基、2-乙基丁氧基、正辛氧基、正壬氧基、正癸氧基、苄氧基、对甲基苄氧基等。烷硫基例如可以包括但不限于甲硫基、乙硫基、正丙硫基、异丙硫基、异丙硫基、正丁硫基、异丁硫基、叔丁硫基、仲丁硫基、正戊硫基、新戊硫基、异戊硫基、正己硫基、3,3-二甲基丁硫基、2-乙基丁硫基、正辛硫基、正壬硫基、正癸硫基、苄硫基等。
【环烷基】可为环状的，并且碳原子数没有特别限制。在一些实施例中，环烷基包括但不限于环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等。
【杂环烷基】可为含杂原子的环烷基，并且碳原子数没有特别限制。在一些实施例中，杂环烷基包括但不限于等。
【芳基】没有特别限定，芳基可为单环芳基或多环芳基。在一些实施例中，单环芳基包括但不限于苯基、联苯基、三联苯基、四联苯基、五联苯基等。多环芳基包括但不限于萘基、蒽基、菲基、芘基、苝基、芴基等。芴基可为经取代的，例如9,9’-二甲基芴基、9,9’-二苯并芴基等。此外，取代基中的两个可彼此结合形成螺环结构，例如9,9’-螺二芴基等。
以上对芳基的描述可用于亚芳基，不同之处在于亚芳基为二价。
以上对芳基的描述可用于芳氧基、芳基硫基、芳基磺酰基、芳基膦基、芳烷基、芳烷基胺基、芳烯基、烷基芳基、芳基胺基和芳基杂芳基胺基中的芳基。
【杂芳基】包含N、O、P、S、Si和Se中的一个或多个作为杂原子。杂芳基包括但不限于吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、咪唑基、吡唑基、唑基、异唑基、噻唑基、异噻唑基、三唑基、二唑基、噻二唑基、二噻唑基、四唑基、吡喃基、噻喃基、吡嗪基、嗪基、噻嗪基、二氧杂环己烯基、三嗪基、四嗪基、喹啉基、异喹啉基、喹啉基、喹唑啉基、喹喔啉基、萘啶基、吖啶基、呫吨基、菲啶基、二氮杂萘基、三氮杂茚基、吲哚基、二氢吲哚基、中氮茚基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、苯并噻唑基、苯并噁唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、茚并咔唑基、吩嗪基、咪唑并吡啶基、吩嗪基、菲啶基、菲咯啉基、吩噻嗪基、咪唑并吡啶基、咪唑并菲啶基、苯并咪唑并喹唑啉基、苯并咪唑并菲啶基、螺[芴-9，9'-氧杂蒽]、苯联萘基、二萘并呋喃基、萘苯并呋喃基、二萘并噻吩基、萘苯并噻吩基、三苯基氧化膦、三苯基硼烷等。
以上对杂芳基的描述可用于杂芳基胺基和芳基杂芳基胺基中的杂芳基。
以上对杂芳基的描述可用于亚杂芳基，不同之处在于亚杂芳基为二价的。
本发明的第一方面提供一种化合物，其具有如式(1)所示的化学结构：
式(1)中，Ar1-Ar4相同或不相同，独立选自取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基，且Ar1-Ar4中至少一个含有选自氰基、硝基、三氟甲基、羧基、含氟基团、叔丁基或异丙基的取代基团；
L1和L2相同或不相同，独立选自单键、取代或未取代的C6-C30芳基、取代或未取代的C5-C30杂芳基；
A选自取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基、硅原子数为1-30的硅烷基团、亚砜基或磷氧基基团。
在一些实施方式中，式(1)中，A选自以下基团中的一种或多种：
其中，R1和R2选自取代或未取代的直链或支链的C1-C30烷基、取代或未取代的C1-C30杂烷基、取代或未取代的C3-C30环烷基、取代或未取代的C3-C30杂环烷基，m、n和t选自然数，*为原子连接位点。
在一些实施方式中，式(1)中，Ar1-Ar4相同，选自
中的一种，#为连接位置。
在一些实施方式中，式(1)中，L1和L2相同，选自单健或亚苯基。
在一些实施方式中，所述化合物选自以下化学结构中的一种或多种：
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具体的，上述化学结构可为未取代或者选自以下的一个或多个取代基取代。例如可以是氘、卤素基团、腈基、硝基、羟基、羰基、酯基、酰亚胺基、胺基、氧化膦基团、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基磺酰基、芳基磺酰基、甲硅烷基、硼基、烷基、环烷基、烯基、芳基、芳烷基、芳烯基、烷基芳基、烷基胺基、芳烷基胺基、杂芳基胺基、芳基胺基、芳基杂芳基胺基、芳基膦基和杂芳基等。
上述有机化合物以烷基为中心结构，同时连接对称的双胺结构，而且在芳环或杂芳环上引入强吸电子基团如三氟甲基、氰基和硝基等，使所形成的化合物具有较低的折射率、具备有一定的紫外吸收，将其作为覆盖层材料用于OLED器件中可以有效地提升器件的发光效率和色纯度。
本发明另一方面提供一种有机材料，包括本发明前述的化合物。
本发明另一方面提供如本发明前述的化合物和/或前述的有机材料在有机光电器件中的应用。
本发明提供的有机光电器件中，包括第一电极、第二电极、以及设置在第一电极和第二电极之间的一个或多个有机层，为底部或顶部发光器件结构，其有机层可为单层结构，也可为层合有两个或多个有机层的多层串联结构，所述有机层如具有包括覆盖层、空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层。可使用制备有机光电器件的常见方法和材料来制备。本发明的有机光电器件采用化合物作为有机光电器件的有机层。
本发明提供的有机光电器件中，第一电极作为阳极层，阳极材料例如可以是具有大功函数的材料，使得空穴顺利地注入有机层。更例如可以是金属、金属氧化物、金属和氧化物的组合、导电聚合物等。金属氧化物例如可以是氧化铟锡(ITO)、氧化锌、氧化铟、和氧化铟锌(IZO)等。
本发明提供的有机光电器件中，第二电极作为阴极层，阴极材料例如可以是具有小功函数的材料，使得电子顺利地注入有机层。阴极材料例如可以是金属或多层结构材料。金属例如可以是镁、银、钙、钠、钾、钛、铟、钇、锂、钆、铝、锡和铅、或其合金。阴极材料优选选自镁和银。
本发明提供的有机光电器件中，空穴注入层的材料，优选最高占据分子轨道(HOMO)介于阳极材料的功函数与周围有机层的HOMO之间的材料作为在低电压下有利地从阳极接收空穴的材料。
本发明提供的有机光电器件中，空穴传输层的材料是对空穴具有高迁移率的材料适合作为接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料。空穴传输层的材料包括但不限于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等。
本发明提供的有机光电器件中，本发明提供的化合物可以应用于器件的发光层。
本发明提供的有机光电器件中，电子传输层的材料是对电子具有高迁移率的材料适合作为有利地接收来自阴极的电子并将电子传输至发光层的材料。
本发明提供的有机光电器件中，覆盖层的材料通常具有高折射率或低折射率，因此可有助于有机发光器件的光效率提高，尤其是有助于外部发光效率提高。
本发明提供的有机光电器件中，所述有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管等。
本发明另一方面提供一种显示或照明装置，包括本发明前述的有机光电器件。
以下通过特定的具体实施例说明本发明的实施方式。
合成实施例
上述式(1)所示的化合物合成可以使用已知的方法进行，例如使用镍、钯等过渡金属的交叉偶合反应。其他合成方法是使用镁或锌等过渡金属的C-C、C-N偶联生成反应。上述反应限于反应条件温和、各种官能团的选择性优越等特点，优选Suzuki、Buchwald反应。本发明的化合物用以下实施例举例说明，但并不限于这些实施例举例的化合物和合成方法。本发明的初始原料和溶剂和一些常用的OLED中间体类等产品购于国内的OLED中间体厂商；各种钯催化剂，配体等购于sigma-Aldrich公司，1H-NMR数据使用JEOL(400MHz)核磁共振仪来测定，HPLC数据使用岛津LC-20AD高效液相仪来测定。
实施例中使用物质为：
实施例1
化合物1的合成
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在氩气氛围下，向反应容器中加入化合物1-A 22.8克(100mmol)，化合物1-B118.8克(400mmol)，叔丁醇钠23.4克(240mmol)，双二亚苄基丙酮钯575毫克(1mmol％)，四氟硼酸三叔丁基膦348毫克(1.2mmol％)和1000mL二甲苯(Xylene)，在140℃加热搅拌15小时。反应混合物冷却到室温，加入1000mL水，过滤，滤饼用大量水洗涤，真空干燥，粗品通过硅胶柱层析法精制(洗脱液：乙酸乙酯/己烷)，得到92.8克化合物1，HPLC纯度99.9％，收率76％，LC MS：M/Z 1220.07(M+)。
实施例2
化合物33的合成
除了起始原料更换为33-A以外，其他与实施例1相同，LCMS:M/Z 1330.18(M+)，HPLC纯度：99.9％，收率：70％；
实施例3
化合物65的合成
除了起始原料更换为65-A以外，其他与实施例1相同，LC MS:M/Z 1288.14(M+)。总收率：77％；HPLC纯度：99.9％。
实施例4
化合物88的合成
除了起始原料更换为88-A以外，其他与实施例1相同，LC MS:M/Z 1249.10(M+)。收率：75％；HPLC纯度：99.9％。
实施例5
化合物129的合成
除了起始原料更换为117-A、117-B和54-C以外，其他与实施例1相同，LC MS:M/Z651.18(M+)。收率：70％；HPLC纯度：99.9％。
实施例6
化合物132的合成
除了起始原料更换为132-A以外，其他与实施例1相同，LCMS:M/Z 1374.08(M+)。收率：75％；HPLC纯度：99.9％。
实施例7
化合物164的合成
除了起始原料更换为164-A和164-B以外，其他与实施例1相同，LC MS:M/Z 800.26(M+)。收率：52％；HPLC纯度：99.9％。
实施例8
化合物167的合成
除了起始原料更换为167-A和167-B以外，其他与实施例1相同，LC MS:M/Z 732.20(M+)；收率：53％；HPLC纯度：99.9％。
实施例9
化合物247的合成
除了起始原料更换为247-A和146-B以外，其他与实施例1相同，LC MS:M/Z 634.13(M+)；合成总收率：56％；HPLC纯度：99.9％。
实施例10
化合物253的合成
除了起始原料更换为253-A和253-B以外，其他与实施例1相同，LC MS:M/Z 754.18(M+)；合成总收率：59％；HPLC纯度：99.9％。
实施例11
化合物273的合成
除了起始原料更换为273-A和273-B以外，其他与实施例1相同，LC MS:M/Z1090.99(M+)；合成总收率：51％；HPLC纯度：99.9％。
实施例12
化合物280的合成
除了起始原料更换为280-A和280-B以外，其他与实施例1相同，LC MS:M/Z1056.75(M+)；合成总收率：51％；HPLC纯度：99.9％。
器件实施例1
首先用超声波清洗仪，使用异丙醇洗涤无碱玻璃15分钟，然后在空气中进行30分钟UV臭氧洗涤处理。处理好的基板利用真空蒸镀法，首先蒸镀铝100纳米作为阳极，然后在阳极上蒸镀空穴注入层(HATCN，50纳米)，空穴传输层(NPD，30纳米)，蓝色发光层(主体ADN和掺杂BD(重量比95：5，30纳米)，电子传输层(Alq 3：Liq＝1:1，30纳米)，电子注入层(LiF，0.5纳米)依次层叠蒸镀后，共蒸镀Mg和Ag(重量比10：1，15纳米)作成半透明阴极。在半透明阴极上，依次蒸镀化合物1(60纳米)作为第二覆盖层，膜厚10纳米，TBDB作为第一覆盖层，膜厚50纳米，最后在氮气氛围下利用环氧树脂粘合剂封装封发光器件。
上述发光器件在室温和大气中，用10mA/cm2直流电流，分光放射辉度计(CS1000，柯尼卡美能达株式会社)测试封口板的发光性能，测试得到其发光效率为7.3cd/A、色纯度CIE(x,y)＝(0.139,0.051)，使用化合物1和TBDB作为双覆盖层得到高发光效率和高色纯度的有机电致发光器件，测试结果见表1。
器件实施例2-12
除在形成覆盖层时，分别以化合物33、65、88、129、132、164、167、247、253、273和280替代化合物1外，采用与器件实施例1相同的方法制作有机电致发光器件，测试结果见表1。
对比例1-2
除在形成覆盖层时，分别以化合物TBDB为第一覆盖层(对比例1)、以化合物TBDB为第一覆盖层和化合物NPD作为第二覆盖层替代化合物1(对比例2)外，采用与器件实施例1相同的方法制作有机电致发光器件，测试结果见表1。
表1
由表1可知，本发明的化合物作为第二覆盖层应用于OLED发光器件，与比较例1相比，引入第二覆盖层后光取出得到显著提升，在相同电流密度下，器件效率得到提升。与比较例2相比，具有低折射率的本发明化合物作为第二覆盖层的器件效率有显著提升。同时，由于OLED发光器件的效率得到提升，在同等亮度的功耗下有机电致发光器件的寿命也得以提升。另外，本发明的化合物作为第二覆盖层应用于OLED发光器件，能够得到高色纯度的发光器件，适合于工商业应用，例如作为有机EL显示器、照明光源、标示板和标识灯等显示或照明装置。
以上测试结果证明，本发明提供的化合物适用于有机电致发光器件的覆盖层材料，能够得到高发光效率和高色纯度的发光器件，特别适用于OLED发光器件。
以上所述，仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。

Claims (7)

1.化合物，其特征在于，所述化合物选自以下化学结构中的一种或多种：
2.一种有机材料，包括权利要求1所述化合物中的一种或多种。
3.一种有机光电器件，包括权利要求1所述化合物中的一种或多种、或者权利要求2所述有机材料。
4.根据权利要求3所述的有机光电器件，其特征在于，
包括基板、第一电极、包含发光层在内的一层以上有机层和第二电极元件；
还包括覆盖层，且所述覆盖层材料包括权利要求1所述化合物中的一种或多种、或者权利要求2所述有机材料。
5.根据权利要求3所述的有机光电器件，其特征在于，所述有机光电器件选自有机光伏器件、有机发光器件、电子纸、有机感光体或有机薄膜晶体管。
6.根据权利要求5所述的有机光电器件，其特征在于，所述有机光伏器件是有机太阳电池。
7.一种显示或照明装置，其特征在于，包括权利要求3-6任一项所述有机光电器件。
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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009190977A (ja) * 2008-02-12 2009-08-27 Konica Minolta Business Technologies Inc アミン化合物、電子写真感光体、画像形成方法及び画像形成装置
CN103828485A (zh) * 2011-09-12 2014-05-28 保土谷化学工业株式会社 有机电致发光器件
KR20160141360A (ko) * 2015-05-27 2016-12-08 삼성디스플레이 주식회사 유기 발광 소자
KR20190128954A (ko) * 2018-05-09 2019-11-19 에스에프씨 주식회사 고효율의 유기 발광 소자
KR20200032658A (ko) * 2018-09-18 2020-03-26 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN112028853A (zh) * 2020-09-09 2020-12-04 长春海谱润斯科技股份有限公司 一种芳胺衍生物及其有机电致发光器件
CN112028913A (zh) * 2019-06-03 2020-12-04 北京鼎材科技有限公司 一种新型含硼有机电致发光材料及其应用
WO2021036683A1 (zh) * 2019-08-27 2021-03-04 东丽先端材料研究开发（中国）有限公司 芳香胺化合物、覆盖层材料及发光元件
CN112979623A (zh) * 2021-02-22 2021-06-18 吉林奥来德光电材料股份有限公司 一种五元杂环基化合物及其制备方法，有机电致发光器件及元件
WO2022034907A1 (ja) * 2020-08-12 2022-02-17 東ソー株式会社 金属パターニング用材料、アミン化合物、および電子機器、ならびに、金属パターンの形成方法

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009190977A (ja) * 2008-02-12 2009-08-27 Konica Minolta Business Technologies Inc アミン化合物、電子写真感光体、画像形成方法及び画像形成装置
CN103828485A (zh) * 2011-09-12 2014-05-28 保土谷化学工业株式会社 有机电致发光器件
KR20160141360A (ko) * 2015-05-27 2016-12-08 삼성디스플레이 주식회사 유기 발광 소자
KR20190128954A (ko) * 2018-05-09 2019-11-19 에스에프씨 주식회사 고효율의 유기 발광 소자
KR20200032658A (ko) * 2018-09-18 2020-03-26 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN112028913A (zh) * 2019-06-03 2020-12-04 北京鼎材科技有限公司 一种新型含硼有机电致发光材料及其应用
WO2021036683A1 (zh) * 2019-08-27 2021-03-04 东丽先端材料研究开发（中国）有限公司 芳香胺化合物、覆盖层材料及发光元件
WO2022034907A1 (ja) * 2020-08-12 2022-02-17 東ソー株式会社 金属パターニング用材料、アミン化合物、および電子機器、ならびに、金属パターンの形成方法
CN112028853A (zh) * 2020-09-09 2020-12-04 长春海谱润斯科技股份有限公司 一种芳胺衍生物及其有机电致发光器件
CN112979623A (zh) * 2021-02-22 2021-06-18 吉林奥来德光电材料股份有限公司 一种五元杂环基化合物及其制备方法，有机电致发光器件及元件

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