CN114656392A - 有机化合物、有机光电器件及显示或照明装置 - Google Patents

有机化合物、有机光电器件及显示或照明装置 Download PDF

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CN114656392A
CN114656392A CN202210321757.5A CN202210321757A CN114656392A CN 114656392 A CN114656392 A CN 114656392A CN 202210321757 A CN202210321757 A CN 202210321757A CN 114656392 A CN114656392 A CN 114656392A
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CN114656392B (zh
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王鹏
王湘成
何睦
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Shanghai Yaoyi Electronic Technology Co ltd
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

本发明公开了有机化合物、有机光电器件及显示或照明装置，属于有机光电材料技术领域。该化合物具有
Figure DDA0003572000260000011
所示的结构，R选自取代或未取代的C1‑C60烷基或杂烷基、取代或未取代的C3‑C60环烷基或杂环烷基、取代或未取代的C6‑C60芳基或C5‑C60杂芳基；Ar为取代或未取代的C6‑C60芳基或C5‑C60杂芳基；A1、A2……An相同或不相同，选自取代或未取代的C3‑C60环烷基或杂环烷基。本发明的上述化合物可作为电子传输材料、空穴传输材料和主体材料等用于各种有机光电器件以及显示或照明装置，色纯度、亮度和发光效率等光电性能好。

Description

有机化合物、有机光电器件及显示或照明装置
技术领域
本发明属于有机光电材料领域，具体涉及有机化合物、有机光电器件及显示或照明装置。
背景技术
有机电激发光二极管(Organic Light Emitting Diode，简称为OLED)，该发光器件具有薄型且能在低驱动电压下高亮度发光以及通过选择发光材料而进行多色发光的特征，因此倍受关注。该研究自从由柯达公司的C.W.Tang等揭示有机薄膜元件能以高亮度发光以来，大量OLED行业研究人员对于其应用进行很多研究和推进，有机薄膜发光器件被广泛应用在各种主显示屏等中，其实用化取得长足的进展。尽管有机电致发光的研究进展非常迅速，但仍有很多亟待解决的问题，例如外量子效率(EQE)仍然需要提高，如何设计与合成出色纯度更高、高效电子传输/空穴阻挡新材料等。对于有机电致发光器件来说，器件的发光量子效率是各种因素的综合反映，也是衡量器件品质的一个重要指标。
电致发光一般可以分为荧光发光和磷光发光。在荧光发光中，单线态激发状态的有机分子跃迁至基态，由此发出光。另一方面，在磷光发光中，三线态激发状态的有机分子跃迁至基态，由此发出光。目前来看，部分有机电致发光材料由于其性能优秀，已经在商业上有所应用，但仍需要具备有高迁移率的电子传输材料、空穴传输材料。另外，现有的材料需要较高的蒸镀温度，一方面耗能，另一方面对器件的制作不利。再者，作为有机电致发光器件的主体材料，除了三线态能级要高于客体材料，防止激子跃迁释放的能量逆传递以外，更重要的是具有良好的空穴迁移性能。目前，主体材料中同时具有高三线态能级和良好空穴迁移率的材料仍然缺乏。因此，如何设计具有高迁移率的电子传输材料、空穴传输材料以及性能更好的主体材料，一直是本领域技术人员亟待解决的问题。
发明内容
如上所述，在OLED领域设计具有高迁移率的材料、低的蒸镀温度以及性能更好的主体材料是现阶段需要解决的问题。本发明的目的是提供一种有机化合物、有机光电器件及显示或照明装置，该类化合物通过引入环烷烃基或杂环烷烃基，降低材料的蒸镀温度的同时迁移率也有所提升，用于有机光电器件和显示装置的有机层材料具有优异的色纯度、高亮度和高发光效率。
本发明提供的有机化合物，其具有式(1)所示的结构：
Figure BDA0003572000250000021
在式1中，R选自氢、氘、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环；其中，所述取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C5-C60 杂芳基中的杂原子选自O、S、N、P、Si、Se或B；
A1、A2……An相同或不相同，各自独立选自取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基，n为正整数1、2、3、4……；
Ar具有式(2)所示的结构：
Figure BDA0003572000250000022
在式2中，X1和X2相同或不相同，独立选自单键、O、S、-CR3R4-、-SiR5R6-、-SeR7R8-、 -NR9-；
Z1-Z8相同或不相同，各自独立选自-CR10-或N；
R1和R2相同或不相同，独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60 杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基，且R1和R2至少一个选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；
R3-R9各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基，且R3和R4至少一个为氢；
R10选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；
*表示与相邻原子的结合位点，m表示*的数量，为不小于1的正整数。
本发明还提供一种有机光电器件，包括阴极层、阳极层和有机层，其中所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层，包含所述有机化合物，所述有机光电器件包括有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体和有机薄膜晶体管。
本发明还提供一种显示或照明装置，其包括所述有机光电器件。
与现有技术相比，本发明的有机化合物通过引入环烷烃基或杂环烷烃基，降低材料的蒸镀温度的同时迁移率也有所提升，可以作为电子传输材料、空穴传输材料和主体材料等应用于各种有机光电器件以及显示或照明装置，色纯度、亮度和发光效率等光电性能优异。
具体实施方式
为使本发明实施例的目的、技术方案和优点更加清楚，下面将结合本发明实施例，对本发明实施例的技术方案进行清楚、完整地描述。显然，所描述的实施例是本发明的一部分实施例，而不是全部的实施例。基于所描述的本发明的实施例，本领域普通技术人员在无需创造性劳动的前提下所获得的所有其它实施例，都属于本发明保护的范围。
以下实施例中采用的有机化合物，其具有式(1)所示的结构：
Figure BDA0003572000250000031
在式1中，R选自氢、氘、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环；其中，所述取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C5-C60 杂芳基中的杂原子选自O、S、N、P、Si、Se或B；
A1、A2……An相同或不相同，各自独立选自取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基，n为正整数1、2、3、4……；
Ar具有式(2)所示的结构：
Figure BDA0003572000250000032
在式2中，X1和X2相同或不相同，独立选自单键、O、S、-CR3R4-、-SiR5R6-、-SeR7R8-、 -NR9-；
Z1-Z8相同或不相同，各自独立选自-CR10-或N；
R1和R2相同或不相同，独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60 杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基，且R1和R2至少一个选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；
R3-R9各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基，且R3和R4至少一个为氢；
R10选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；
*表示与相邻原子的结合位点，m表示*的数量，为不小于1的正整数。
上述式1所示的有机化合物中，m＝2n。
上述式1所示的有机化合物中取代基的描述如下，当不限于此。
“取代或未取代的”指选自以下一个或多个取代基取代：氢、氘、卤素、腈基、硝基、羟基、羰基、酯基、酰亚胺基、氨基、氧化膦基、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、芳基胺基和杂环基，或未取代；或者连接以上取代基中的两个或多个取代基的取代基取代，或未取代，如“连接两个或多个取代基的取代基”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。
“芳基”可为单环芳基或多环芳基，单环芳基包括苯基、联苯基、三联苯基、四联苯基、五联苯基，多环芳基包括萘基、蒽基、菲基、芘基、苝基、芴基，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。
“杂芳基”包含N、O、P、S、Si、Se或B中的一个或多个作为杂原子，碳原子数为5至60，选自吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、硒吩基、咪唑基、吡唑基、噁唑基、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、或苯并咪唑并菲啶基，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。
作为优选方案，在式1中，A1、A2……An各自独立选自如下任一结构：
Figure BDA0003572000250000051
其中，X5-X30相同或不相同，各自独立选自-NR11-、O、S、-CR12R13-、-SiR13R14-、-SeR15R16-；
R11-R16各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基，*表示与相邻原子的结合位点。
作为优选方案，在式2中，R1和R2分别选自氢或如下任一所示的基团：
Figure BDA0003572000250000052
Figure BDA0003572000250000061
其中，R17选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60 杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环，*表示与相邻原子的结合位点。
作为优选方案，在式2中，R1和R2分别选自氢或如下任一所示的基团：
Figure BDA0003572000250000062
其中，Ar1和Ar2相同或不相同，分别选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环；
R18和R19相同或不相同，独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60 杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环，*表示与相邻原子的结合位点。
作为优选方案，在式1中，Ar选自如下任一个基团：
Figure BDA0003572000250000071
其中，R20-R24相同或不相同，独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的 C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环，*表示与相邻原子的结合位点。
作为优选方案，所述有机化合物选自如下任一化学式所示的化合物：
Figure BDA0003572000250000072
Figure BDA0003572000250000081
Figure BDA0003572000250000091
Figure BDA0003572000250000101
Figure BDA0003572000250000111
Figure BDA0003572000250000121
Figure BDA0003572000250000131
Figure BDA0003572000250000141
Figure BDA0003572000250000151
Figure BDA0003572000250000161
Figure BDA0003572000250000171
Figure BDA0003572000250000181
Figure BDA0003572000250000191
Figure BDA0003572000250000201
Figure BDA0003572000250000211
Figure BDA0003572000250000221
Figure BDA0003572000250000231
Figure BDA0003572000250000241
上述式(1)所示的有机化合物可以使用已知的方法进行合成，例如使用镍、钯等过渡金属的交叉偶合反应，其他合成方法如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。以下合成实施例中列举若干本发明中有机化合物的合成方法，但并不限于这些实施例。
初始原料和溶剂购于江苏三月光电有限公司，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。
以下合成实施例1-30中合成如下有机化合物：
Figure BDA0003572000250000251
实施例1
化合物21的合成
Figure BDA0003572000250000252
在氩气氛围下，向反应容器中加入化合物21-A37.6克(110mmol)，化合物21-B30.0克 (100mmol)、Pd(PPh3)2Cl21.4克(2mmol)、1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME)，80℃加热搅拌一晚。冷却至室温，加入800ml水，大量固体析出，过滤，滤饼用水搅洗3次，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43.0克化合物21，收率83％，HPLC纯度99.9％。
1HNMR(DMSO)：δ8.28(s，1H),8.21(d，1H),8.10(s，1H),8.07–8.06(m,3H)7.84(d,2H),7.66 (s,1H),7.60(m,3H),7.53–7.49(m,4H),7.34(m,1H),2.70(t,4H),1.82(s,6H),1.74(t,4H)。
实施例2
化合物108的合成
Figure BDA0003572000250000261
除了起始原料更换为108-A和108-B以外，其他与实施例1相同。
1HNMR(DMSO)δ8.03(m,2H),7.89(d,1H),7.80(d,1H),7.71(s,1H)7.64(s,1H),7.58(m,2H),7.30(d, 1H),7.24(d,1H),2.74–2.70(m,8H),1.74–1.72(m,8H),1.69(s,6H)。
实施例3
化合物168的合成
Figure BDA0003572000250000262
除了起始原料更换为168-A和168-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.83(d,1H),8.40(s,1H),8.11(d,1H),8.10(s,1H),8.03(d,6H),7.41(m,1H),7.32 (d,6H),2.70(t,4H),1.75(s,6H),1.74(m,4H)。
实施例4
化合物245的合成
Figure BDA0003572000250000263
除了起始原料更换为245-A和245-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.84(d,1H),8.36(d,4H),8.30(s,1H),8.14(d,1H),8.11(d,1H),7.51–7.49(m,8H), 7.41(m,1H),2.74–2.70(m,4H),1.75(s,6H),1.74–1.72(m,4H)。
实施例5
化合物776的合成
Figure BDA0003572000250000264
除了起始原料更换为776-A和776-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.84(s,1H),8.36(d,4H),8.02(s,1H),7.91(d,1H),7.68(d,1H),7.62(m,2H),7.58– 7.56(m,2H),7.50(m,8H),2.70(t,4H),1.74(t,4H)。
实施例6
化合物818的合成
Figure BDA0003572000250000271
除了起始原料更换为818-A和818-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.14(d,4H),7.94(d,2H),7.74(d,1H),7.53(m,4H),7.51(m,3H),7.43(m,2H), 7.05(d,1H),2.97(s,2H),2.92(t,2H),2.74–2.70(m,6H),1.74–1.71(m,8H)。
实施例7
化合物1090的合成
Figure BDA0003572000250000272
除了起始原料更换为1090-A和1090-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.07(d,2H),8.03(d,1H),7.94(d,1H),7.84(d,2H),7.78(s,1H),7.68(d,1H), 7.65(s,1H),7.60(m,3H),7.53(m,2H),7.49(m,1H),2.70(t,4H),1.74(t,4H)。
实施例8
化合物1120的合成
Figure BDA0003572000250000273
除了起始原料更换为1120-A和1120-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.06(d,1H),7.75–7.74(m,4H),7.37(d,1H),7.38(d,2H),7.21(d,1H),2.74–2.70 (m,4H),1.74–1.72(m,4H),0.66(s,6H)。
实施例9
化合物1530的合成
Figure BDA0003572000250000281
除了起始原料更换为1530-A和1530-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.56(d,1H),8.28(s,1H),8.22(s,1H),8.21(d,1H),8.06(d,1H),7.81(d,1H),7.78 (s,1H),7.62(m,1H),7.53–7.51(m,2H),7.48(m,2H),7.38(d,2H),7.34(m,1H),7.28(m,1H),2.85(m,2H),1. 82(s,6H),1.44(m,2H),1.42(m,4H)。
实施例10
化合物1624的合成
Figure BDA0003572000250000282
除了起始原料更换为1624-A和1624-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.02(d,2H),7.98(d,1H),7.95(s,1H),7.81(d,1H),7.62(m,2H),7.59(m,3H),7.51 (d,4H),7.49(d,1H),7.47–7.46(m,4H),7.41(m,1H),7.08(m,2H),7.02(s,1H),4.28(s,4H)。
实施例11
化合物471的合成
Figure BDA0003572000250000283
除了起始原料更换为471-A和471-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.18(s,1H),7.90(d,2H),7.74–7.68(m,2H),7.55(d,2H),7.45(d,1H),7.38 (m,2H),7.33(d,1H),7.28(m,2H),7.26(s,1H),7.24(m,2H),7.20(d,1H),7.19(m,1H),7.17(d,1H),7.14(d,1 H),7.08(d,1H),7.03(d,1H),7.00(m,1H),6.95(m,1H),2.74–2.70(m,4H),1.74–1.72(m,4H),1.69(s,6H)。
实施例12
化合物494的合成
1)中间体494-1的合成
Figure BDA0003572000250000291
除了起始原料更换为494-A和494-B以外，其他与实施例1相同。
2)化合物494的合成
除了起始原料更换为494-1和494-C以外，其他与实施例1相同。
1HNMR(DMSO):δ8.52(d,1H),8.49(d,1H),8.28(d,1H),8.20(d,1H),8.15(d,2H),8.02(d,1H),8.00 (d,1H),7.92(d,2H),7.90(d,1H),7.86(m,1H),7.80(m,3H),7.70(d,2H),7.67(m,2H),7.64(d,1H),7.61(d,1 H),7.30(d,1H),2.74–2.70(m,4H),1.82(s,6H),1.74–1.72(m,4H)。
实施例13
化合物503的合成
1)中间体503-1的合成
Figure BDA0003572000250000292
除了起始原料更换为503-A和503-B以外，其他与实施例1相同。
2)化合物503的合成
Figure BDA0003572000250000293
除了起始原料更换为503-1和503-C以外，其他与实施例1相同。
1HNMR(DMSO):δ8.42(d,1H),8.36(d,4H),8.25(s,1H),8.22(d,2H),8.19(d,2H),8.14(d,1H),8.05(d ,1H),7.66(m,1H),7.50(m,6H),7.49(d,1H),2.74–2.70(m,4H),1.75(s,6H),1.74–1.72(m,4H)。
实施例14
化合物505的合成
1)中间体505-1的合成
Figure BDA0003572000250000294
除了起始原料更换为505-A和505-B以外，其他与实施例1相同。
2)化合物505的合成
Figure BDA0003572000250000301
除了起始原料更换为505-1和505-C以外，其他与实施例1相同。
1HNMR(DMSO):δ8.56(d,1H),8.52(d,1H),8.42(d,1H),8.28(d,1H),8.25(s,1H),8.15(m,2H),8.05( d,1H),7.92(d,2H),7.87(s,1H),7.81(d,1H),7.70(d,2H),7.66(m,1H),7.64(d,1H),7.62(m,1H),7.53(m,1H) ,7.38(d,2H),7.30(d,1H),7.28(m,1H),2.74–2.70(m,4H),1.75(s,6H),1.74–1.72(m,4H).
实施例15
化合物561的合成
1)中间体561-1的合成
Figure BDA0003572000250000302
除了起始原料更换为561-A和561-B以外，其他与实施例1相同。
2)化合物561的合成
Figure BDA0003572000250000303
除了起始原料更换为561-1和561-C以外，其他与实施例1相同。
1HNMR(DMSO):δ9.05(d,1H),8.97(d,1H),8.91(d,1H),8.84(s,1H),8.50(d,1H),8.12(d,1H),8.07(d ,2H),8.02(s,1H),7.97(d,1H),7.93(m,1H),7.84(d,2H),7.77(m,1H),7.62(m,2H),7.60(m,3H),7.58(m,3H ),7.53(m,2H),7.50(m,3H),7.44(s,1H),2.70(t,4H),1.74(t,4H).
实施例16
化合物737的合成
Figure BDA0003572000250000304
除了起始原料更换为737-A和737-B以外，其他与实施例1相同。
1HNMR(DMSO):δ8.84(s,1H),8.46(s,1H),8.15(d,1H),8.12(d,1H),8.11(d,1H),8.06(d,2H),8.02(d, 1H),8.00(d,1H),7.98(d,2H),7.79(m,1H),7.68(d,1H),7.61–7.59(m,4H),7.56(m,1H),7.51(m,5H),7.46( m,4H),7.41(m,2H),2.70(t,4H),1.74(t,4H).
实施例17
化合物1378的合成
Figure BDA0003572000250000311
除了起始原料更换为1378-A和1378-B以外，其他与实施例1相同。
1HNMR(DMSO):δ8.83(d,1H),8.40(s,1H),8.11(d,1H),8.10(s,1H),8.03(d,6H),7.66(s,1H),7.59(m ,3H),7.51(m,1H),7.51(m,1H),7.41(m,1H),7.32(m,6H),2.85(t,4H),1.84–1.76(m,6H).
实施例18
化合物1513的合成
Figure BDA0003572000250000312
在氩气氛围下，向反应容器中加入化合物1513-A40.5克(100mmol)，化合物1513-B26.7 克(110mmol)，叔丁醇钾26.9克(240mmol)，双二亚苄基丙酮钯575毫克(1mmol％)，2-双环己基膦-2',4',6'-三异丙基联苯953毫克(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51.1克化合物1513，HPLC纯度99.9％，收率90％。
1HNMR(DMSO)：δ8.46(d,1H),8.06(d,2H),8.00(d,1H),7.98(d,1H),7.94–7.93(d,2H),7.80(d,1H), 7.61–7.59(m,2H),7.54(s,1H),7.42(d,1H),7.35(m,1H),6.87(m,1H),6.80(s,1H),2.85(m,4H),1.70(s,6H), 1.69–1.67(m,4H),1.44–1.42(m,4H).
实施例19
化合物1658的合成
1)中间体1658-1的合成
Figure BDA0003572000250000321
除了起始原料更换为1658-A和1658-B以外，其他与实施例1相同。
2)化合物1658的合成
Figure BDA0003572000250000322
除了起始原料更换为1658-1和1658-C以外，其他与实施例1相同。
1HNMR(DMSO)：δ9.05(d,1H),8.91(d,1H),8.50(d,1H),7.97(d,1H),7.95(s,1H),7.93(m,1H), 7.91(m,1H),7.84(d,2H),7.82(d,2H),7.77(m,1H),7.68(d,1H),7.62(m,2H),7.58(m,1H),7.56(m,1H), 7.53(m,2H),7.50(d,2H),7.49(m,1H),7.48(m,3H),7.02(s,1H),4.28(s,4H).
实施例20
化合物1673的合成
Figure BDA0003572000250000323
除了起始原料更换为1673-1和1673-C以外，其他与实施例1相同。
1HNMR(DMSO):δ8.40(d,1H),8.03(d,3H),7.86(s,1H),7.83(s,1H),7.74(m,2H),7.59(m,2H),7.38( d,2H),7.36(d,1H),6.95(d,1H),4.59(s,2H),3.70(t,2H),2.74–2.70(m,6H),1.74–1.72(m,4H).
实施例21
化合物506的合成
Figure BDA0003572000250000324
除了起始原料更换为506-A和506-B以外，其他与实施例18相同。
1HNMR(DMSO)：δ8.30(d,1H),8.18(d,1H),8.13(d,1H),8.10(s,1H),8.09(d,2H),8.06(d,3H),7.99 (d,3H),7.89(s,2H),7.77(d,1H),7.66(s,1H),7.63(m,2H),7.60(m,2H),7.58(m,1H),7.55(s,2H),7.52(s,1H) ,7.38(d,2H),7.34(m,1H),2.70(t,4H),1.82(s,6H),1.74(t,4H).
实施例22
化合物509的合成
Figure BDA0003572000250000331
除了起始原料更换为509-A和509-B以外，其他与实施例18相同。
1HNMR(DMSO)：δ8.55(d,1H),8.19(d,1H),8.01(d,1H),7.99(d,1H),7.94(d,1H),7.89(s,1H),7.78 (d,1H),7.76(s,1H),7.65(d,1H),7.58(d,1H),7.55(s,1H),7.50(m,1H),7.47(m,2H),7.38(d,2H),7.35(m,1H ),7.16(m,1H),2.70(t,4H),1.74(t,4H),1.69(s,6H).
实施例23
化合物512的合成
Figure BDA0003572000250000332
除了起始原料更换为512-A和512-B以外，其他与实施例18相同。
1HNMR(DMSO)：δ8.98(d,1H),8.55(d,1H),8.27(d,1H),8.19(d,1H),8.05(s,1H),8.00(d,1H),7.94 (d,1H),7.86(d,1H),7.80(d,1H),7.77(m,1H),7.68(m,1H),7.64(m,1H),7.58(d,1H),7.57(s,1H),7.35(m,1 H),7.30(d,1H),7.20(m,1H),7.16(m,1H),2.74–2.70(m,4H),1.74–1.72(m,4H),1.69(s,6H).
实施例24
化合物516的合成
Figure BDA0003572000250000333
除了起始原料更换为516-A和516-B以外，其他与实施例18相同。
1HNMR(DMSO)：δ8.55(d,1H),8.30(d,1H),8.19(d,1H),8.17(s,1H),8.13(d,1H),7.99–7.94 (m,4H),7.89(s,2H),7.85(s,1H),7.77(d,1H),7.62(m,2H),7.61(s,1H),7.58(d,2H),7.53(m,1H),7.50(m,3 H),7.35(m,1H),7.20(m,1H),7.16(m,1H),2.74–2.70(m,4H),1.75(s,6H),1.74–1.72(m,4H).
实施例25
化合物518的合成
Figure BDA0003572000250000341
除了起始原料更换为518-A和518-B以外，其他与实施例18相同。
1HNMR(DMSO)：δ8.55(d,1H),8.20(s,1H),8.07(d,1H),7.94(d,1H),7.89(s,1H),7.68(m,1H), 7.65(d,2H),7.64(d,1H),7.62(m,2H),7.58(m,3H),7.52(d,1H),7.50(d,2H),7.35(m,2H),7.30(d,1H),7.16( m,2H),2.74–2.70(m,4H),1.75(s,6H),1.74–1.72(m,4H).
实施例26
化合物520的合成
Figure BDA0003572000250000342
除了起始原料更换为520-A和520-B以外，其他与实施例18相同。
1HNMR(DMSO)：δ8.55(d,2H),8.22(d,1H),8.19(d,1H),8.02(d,1H),7.94(d,2H),7.82(m,1H), 7.72(d,1H),7.68(d,1H),7.64(d,1H),7.59(d,1H),7.58(d,1H),7.50(m,1H),7.38(d,1H),7.35(d,2H),7.30(d ,1H),7.20(m,1H),7.16(m,2H),2.74–2.70(m,4H),1.82(s,6H),1.74–1.72(m,4H).
实施例27
化合物528的合成
Figure BDA0003572000250000343
除了起始原料更换为528-A和528-B以外，其他与实施例18相同。
1HNMR(DMSO)：δ8.55(d,1H),8.22(s,1H),8.21(d,1H),8.19(d,1H),7.99(s,1H),7.94(d,1H), 7.68(m,1H),7.60(d,1H),7.58(d,1H),7.50(m,1H),7.47(d,1H),7.35(m,1H),7.20(m,1H),7.17(s,1H),7.16 (m,1H),7.03(d,1H),2.74(t,8H),1.82(s,6H),1.72(t,8H),1.49(s,9H).
实施例28
化合物532的合成
Figure BDA0003572000250000344
除了起始原料更换为532-A和532-B以外，其他与实施例18相同。
1HNMR(DMSO)：δ8.55(d,2H),8.22(d,1H),8.12(d,2H),8.10(d,1H),8.02(d,1H),7.94(d,2H), 7.82(m,1H),7.68(d,1H),7.66(d,1H),7.59(d,1H),7.58(m,1H),7.57(m,2H),7.50(d,2H),7.35(m,2H),7.16 (m,2H),2.70(t,4H),1.82(s,6H),1.74(t,4H).
实施例29
化合物538的合成
Figure BDA0003572000250000351
除了起始原料更换为538-A和538-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.55(d,1H),8.31(s,2H),8.30(d,1H),8.19(d,2H),8.13(d,1H),7.94(d,1H), 7.89(s,2H),7.80(d,1H),7.62(m,2H),7.58(d,3H),7.57(s,1H),7.50(m,3H),7.35(d,1H),7.30(d,1H),7.20( m,2H),7.16(m,1H),2.74–2.70(m,8H),,1.74–1.72(t,8H),1.69(s,6H).
实施例30
化合物1062的合成
Figure BDA0003572000250000352
除了起始原料更换为1062-A和1062-B以外，其他与实施例1相同。
1HNMR(DMSO)：δ8.55(d,1H),8.21(s,1H),8.19(d,1H),7.97(d,1H),7.95(s,1H),7.94(d,1H), 7.68(m,1H),7.67(s,1H),7.60(d,1H),7.58(d,1H),7.50(m,1H),7.47(d,1H),7.35(m,1H),7.20(m,1H),7.16 (m,1H),7.13(d,1H),2.74(t,8H),1.72(t,8H),1.49(s,9H).
以下实施例中制备的有机光电器件，包括阴极层、阳极层和有机层，其中有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层，包含上述任一有机化合物。
一些实施方式中，有机层选为电子传输层，且电子传输层的材料包含上述任一有机化合物。
一些实施方式中，有机层选为空穴传输层，且空穴传输层的材料包含上述任一有机化合物。
一些实施方式中，有机层选为发光层，且发光层的材料包含上述任一有机化合物。
有机光电器件可以为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体和有机薄膜晶体管。
以下实施例中制备的显示或照明装置，其包括上述任一有机光电器件。
通过制备有机光电器件进行发光性能测试和评价，其中所用的各有机层化合物如下所示：
Figure BDA0003572000250000361
实施例31
本实施例中有机光电器件的基本结构模型为： ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/RH-1：RD(Ir配合物)＝94：6(40nm)/ETL(30nm) 本发明中有机化合物/LiF(1nm)/Al(80nm)。
本实施例中有机光电器件的制造方法，步骤如下：
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)(10Ω/sq)玻璃基板进行超声清洗，再用臭氧等离子处理15分钟。
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后，控制体系压力在10-6托，接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN、40nm的TAPC和10nm的TCTA。
(3)在上述TCTA蒸镀厚度为40nm的发光层(EML)，RH-1与RD的质量比为94：6。
(4)在上述发光层蒸镀厚度为30nm的实施例1合成的化合物21作为电子传输层(ETL) 材料。
(5)在上述电子传输层蒸镀厚度为1nm的LiF作为电子注入层。
(6)最后在上述电子注入层蒸镀厚度为80nm的Al作为阴极，且利用玻璃封装盖对器件进行封装，器件测试结果如表1所示。
实施例32
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物108，器件测试结果如表1所示。
实施例33
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物168，器件测试结果如表1所示。
实施例34
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物245，器件测试结果如表1所示。
实施例35
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物776，器件测试结果如表1所示。
实施例36
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物818，器件测试结果如表1所示。
实施例37
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物1090，器件测试结果如表1所示。
实施例38
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物1120，器件测试结果如表1所示。
实施例39
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物1530，器件测试结果如表1所示。
实施例40
本实施例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为化合物1624，器件测试结果如表1所示。
对比例1
本对比例中器件的制备与实施例31相同，除了电子传输层(ETL)材料为ETL-1，器件测试结果如表1所示。
表1
Figure BDA0003572000250000371
Figure BDA0003572000250000381
由上述实施例31至40、对比例1测试发现，器件结构除了ETL不同外，其它均一致，基于ETL-1作为传输层材料的器件性能为参考，可见本发明的有机化合物作为电子传输层材料的器件电流效率有显著提升，同时器件寿命也有所提升。
实施例41
本实施例制备有机光电器件的基本结构模型为： ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/RH(本发明的有机化合物)：RD(Ir配合物)＝94：6(40nm)/ETL(30nm)/LiF(1nm)/Al(80nm)。
本实施例中有机光电器件的制备方法：
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)(10Ω/sq)玻璃基板进行超声清洗，再用臭氧等离子处理15分钟。
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后，控制体系压力在10-6托，接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN，40nm的TAPC和10nm的TCTA。
(3)在上述TCTA蒸镀厚度为40nm的发光层(EML)，RH(本发明化合物471)与RD 的质量比为94：6。
(4)在上述发光层蒸镀厚度为30nm的ETL材料。
(5)在上述电子传输层蒸镀厚度为1nm的LiF作为电子注入层。
(6)在上述电子注入层蒸镀厚度为80nm的Al作为阴极，且利用玻璃封装盖对器件进行封装，器件测试结果如表2所示。
实施例42
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物494，器件测试结果如表2所示。
实施例43
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物503，器件测试结果如表2所示。
实施例44
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物505，器件测试结果如表2所示。
实施例45
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物561，器件测试结果如表2所示。
实施例46
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物737，器件测试结果如表2所示。
实施例47
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物1378，器件测试结果如表2所示。
实施例48
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物1513，器件测试结果如表2所示。
实施例49
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物1658，器件测试结果如表2所示。
实施例50
本实施例中器件的制备与实施例41相同，除了主体材料(RH)为化合物1673，器件测试结果如表2所示。
对比例2
本对比例中器件的制备与实施例41相同，除了主体材料(RH)材料为RH-1，器件测试结果如表2所示。
表2
实施例 主体材料 驱动电压 电流效率(cd/A) LT95(小时)
41 化合物471 3.0 27.3 4100
42 化合物494 3.1 26.9 3600
43 化合物503 3.2 27.0 3500
44 化合物505 3.0 26.6 3300
45 化合物561 3.0 26.5 3200
46 化合物737 3.2 27.0 4100
47 化合物1378 3.2 25.9 3500
48 化合物1513 3.1 26.4 3100
49 化合物1658 3.0 27.3 3800
50 化合物1673 3.2 26.1 3900
对比例2 RH-1 3.4 25.0 3000
由实施例41至50、对比例2测试，发现器件结构除了RH材料不同外，其它均一致，基于RH-1作为主体材料的器件性能为参考，可见本发明的有机化合物作为主体材料的器件电流效率有显著提升，同时器件寿命也有所提升。
实施例51
本实施例中有机光电器件的基本结构模型为：ITO/HAT-CN(10nm)/本发明有机化合物 (HTL)/RH：RD(Ir配合物)＝94：6(40nm)/ETL(30nm)/LiF(1nm)/Al(80nm)。
本实施例中有机光电器件的制备方法：
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟。
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后，控制体系压力在10-6托，接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN，40nm的本发明化合物506作为空穴传输材料(HTL)。
(3)在上述HTL蒸镀厚度为40nm的发光层(EML)，RH-1与RD的质量比为94：6。
(4)在上述发光层蒸镀厚度为30nm的ETL材料。
(5)在上述电子传输层蒸镀厚度为1nm的LiF作为电子注入层。
(6)在上述电子注入层蒸镀厚度为80nm的Al作为阴极，且利用玻璃封装盖对器件进行封装。
实施例52
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物509，器件测试结果如表3所示。
实施例53
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物512，器件测试结果如表3所示。
实施例54
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物516，器件测试结果如表3所示。
实施例55
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物518，器件测试结果如表3所示。
实施例56
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物520，器件测试结果如表3所示。
实施例57
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物528，器件测试结果如表3所示。
实施例58
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物532，器件测试结果如表3所示。
实施例59
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物538，器件测试结果如表3所示。
实施例60
本实施例中器件的制备与实施例51相同，除了空穴传输材料(HTL)为化合物1062，器件测试结果如表3所示。
对比例3
本对比例中器件的制备与实施例41相同，除了空穴传输层材料(HTL)材料为40nm的 TAPC和10nm的TCTA，器件测试结果如表3所示。
表3
Figure BDA0003572000250000411
Figure BDA0003572000250000421
由实施例51至60、对比例3测试，发现器件结构除了HTL材料不同外，其它均一致，基于TAPC、TCPA作为主体材料的器件性能为参考，本发明的化合物作为空穴传输层材料的器件的电流效率有显著提升，同时器件寿命也有所提升。
综上所述，本发明中有机化合物作为OLED器件的有机层材料，在各种有机光电器件、显示或照明装置具有较大的应用价值。
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 (15)

1.有机化合物，具有式(1)所示的结构：
Figure FDA0003572000240000011
在式1中，R选自氢、氘、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环，其中杂原子选自O、S、N、P、Si、Se或B；
A1、A2……An相同或不相同，各自独立选自取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基，n为正整数1、2、3、4……；
Ar具有式(2)所示的结构：
Figure FDA0003572000240000012
在式2中，X1和X2相同或不相同，独立选自单键、O、S、-CR3R4-、-SiR5R6-、-SeR7R8-、-NR9-；
Z1-Z8相同或不相同，各自独立选自-CR10-或N；
R1和R2相同或不相同，独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基，且R1和R2至少一个选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；
R3-R9各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基，且R3和R4至少一个为氢；
R10选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；
*表示与相邻原子的结合位点，m表示*的数量，为不小于1的正整数。
2.根据权利要求1所述的有机化合物，其特征在于，A1、A2……An各自独立选自如下任一结构：
Figure FDA0003572000240000021
其中，X5-X30相同或不相同，各自独立选自-NR11-、O、S、-CR12R13-、-SiR13R14-、-SeR15R16-；R11-R16各自独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基；*表示与相邻原子的结合位点。
3.根据权利要求1所述的有机化合物，其特征在于，R1和R2分别选自氢或如下任一所示的基团：
Figure FDA0003572000240000022
Figure FDA0003572000240000031
其中，R17选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环，*表示与相邻原子的结合位点。
4.根据权利要求1所述的有机化合物，其特征在于，R1和R2分别选自氢或如下任一所示的基团：
Figure FDA0003572000240000032
其中，Ar1和Ar2相同或不相同，分别选自取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环；
R18和R19相同或不相同，独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环；*表示与相邻原子的结合位点。
5.根据权利要求1-4任一项所述的有机化合物，其特征在于，Ar选自如下任一个基团：
Figure FDA0003572000240000041
其中，R20-R24相同或不相同，独立选自氢、氘、卤素、氰基、取代或未取代的C1-C60烷基、取代或未取代的C1-C60杂烷基、取代或未取代的C3-C60环烷基、取代或未取代的C3-C60杂环烷基、取代或未取代的C6-C60芳基、取代或未取代的C5-C60杂芳基或者与临近的原子键合成环，*表示与相邻原子的结合位点。
6.根据权利要求1所述的有机化合物，其特征在于，所述化合物选自如下任一个化学结构：
Figure FDA0003572000240000042
Figure FDA0003572000240000051
Figure FDA0003572000240000061
Figure FDA0003572000240000071
Figure FDA0003572000240000081
Figure FDA0003572000240000091
Figure FDA0003572000240000101
Figure FDA0003572000240000111
Figure FDA0003572000240000121
Figure FDA0003572000240000131
Figure FDA0003572000240000141
Figure FDA0003572000240000151
Figure FDA0003572000240000161
Figure FDA0003572000240000171
Figure FDA0003572000240000181
Figure FDA0003572000240000191
Figure FDA0003572000240000201
Figure FDA0003572000240000211
7.有机光电器件，包括阴极层、阳极层和有机层，其特征在于，所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层，包含权利要求1-6任一项所述的有机化合物。
8.根据权利要求7所述的有机光电器件，其特征在于，所述有机层包含电子传输层，且所述电子传输层的材料包含权利要求1-6任一项所述的有机化合物。
9.根据权利要求8所述的有机光电器件，其特征在于，所述电子传输层的材料包含权利要求3所述的有机化合物。
10.根据权利要求7所述的有机光电器件，其特征在于，所述有机层包含空穴传输层，且所述空穴传输层的材料包含权利要求1-6任一项所述的有机化合物。
11.根据权利要求10所述的有机光电器件，其特征在于，所述空穴传输层的材料包含权利要求4所述的有机化合物。
12.根据权利要求7所述的有机光电器件，其特征在于，所述有机层包含发光层，且所述发光层的材料包含权利要求1-6任一项所述有机化合物。
13.根据权利要求12所述的有机光电器件，其特征在于，所述发光层的材料包含权利要求4所述的有机化合物。
14.根据权利要求7-13任一项所述的有机光电器件，其特征在于，所述有机光电器件包括有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体和有机薄膜晶体管。
15.显示或照明装置，其特征在于，其包括权利要求7-13任一项所述的有机光电器件。
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