CN113501810B - 一种有机化合物和含其的有机光电元件 - Google Patents

一种有机化合物和含其的有机光电元件 Download PDF

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CN113501810B
CN113501810B CN202110640090.0A CN202110640090A CN113501810B CN 113501810 B CN113501810 B CN 113501810B CN 202110640090 A CN202110640090 A CN 202110640090A CN 113501810 B CN113501810 B CN 113501810B
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王子兴
王朋超
廖张程
吴空物
张迪
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

本发明属于有机光电领域，具体涉一种有机化合物及包含其的有机光电元件，特别是有机电致发光二极管，其中有机化合物的结构如式(I)所示：
Figure DDA0003107246680000011
式(I)代表的有机化合物群组具有一个显著的特征是它们的单线态能级S1与三线态能级T1的差值≤0.35电子伏特，详细说明信息及其有机光电元件可通过参照本文中提供的具体描述进行理解。本发明的有机化合物具有热活化延迟荧光特性，应用于有机电致发光二极管中，可提升三线态激子的利用效率，具体为使本发明的化合物作为发光元件功能层，可以使发光元件的电流效率提升，驱动电压降低，使用寿命明显延长，具有很好的商业化前景。

Description

一种有机化合物和含其的有机光电元件
技术领域
本发明属于有机光电领域，具体涉及一种有机化合物及包含其的有机光电元件，特别是有机电致发光二极管。
背景技术
有机电致发光器件(OLED)有视角广阔、响应速度快、色彩质量高、可实现柔性发光等优点，具有广阔的应用前景。一个效率高、寿命长的有机电致发光器件通常是器件结构与各种有机材料的优化搭配的结果。常见的OLED器件通常包括以下种类的有机材料：空穴注入材料、空穴传输材料、电子传输材料，以及各色的发光材料(染料或者掺杂客体材料)和相应的主体材料等。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，比如效率的提高，色纯度更高的新材料的设计与合成；高效三线态激子利用率的主客体材料的设计与合成等。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。因而，设计发展三线态激子利用率高的主体材料具有重要意义。
本发明提供了一种有机化合物，该有机化合物通过芳香或杂芳香环连接给体和受体基团，使电子和空穴的传递更加平衡；分子具有合适的三线态能级和热活化延迟荧光特性，即有机化合物的单线态能级S1与三线态能级T1的差值≤0.35电子伏特，可以提升发光器件中三线态激子能量的利用率，具体表现为使用本发明的有机化合物构建的器件的效率提高，电压降低，使用寿命延长。
发明内容
本发明提供一种有机化合物，其结构式如式(I)所示:
Figure BDA0003107246660000011
其中，X1至X3独立选自N或C-R4，且至少有两个为N；环CY1为C7～C30的芳香稠环或芳香杂稠环，Ar1、Ar2独立选自取代或未取代的C6～C60的芳基、取代或未取代的C1～C60的杂芳基；R1至R5各自独立地选自氢、氘、CN、卤素、取代或未取代的C1～C60的烷基、取代或未取代的C2～C60的烯基、取代或未取代的C1～C60的烷氧基、取代或未取代的C1～C60的环烷基、取代或未取代的C1～C60的杂烷基、取代或未取代的C6～C60的芳基、取代或未取代的C1～C60的杂芳基、取代或未取代的C1～C60的胺基、取代或未取代的C1～C60的硅基、取代或未取代的C6～C60的芳族稠环、取代或未取代的C1～C60的杂芳族稠环；Ar1、Ar2、R1至R4各自独立地可被部分或全部氘代、各自独立地可被部分或全氟代；R1至R5可以根据价健原则不取代或多取代；相邻的R1至R5可以成环，n独立地为0至8的整数；且所述有机化合物的单线态能级S1与三线态能级T1的差值≤0.35电子伏特。
优选地，结构式(I)中环CY1独立选自式(A)至式(H)中的一种，但并不代表本发明限于以下结构：
Figure BDA0003107246660000021
其中，Y独立选自O、S、N-R7、CR7R7、SiR7R7、B-R7中的一种，Z独立地为N或C-R；R5至R7各自独立地选自氢、氘、CN、卤素、取代或未取代的C1～C60的烷基、取代或未取代的C2～C60的烯基、取代或未取代的C1～C60的烷氧基、取代或未取代的C1～C60的环烷基、取代或未取代的C1～C60的杂烷基、取代或未取代的C6～C60的芳基、取代或未取代的C1～C60的杂芳基、取代或未取代的C1～C60的胺基、取代或未取代的C1～C60的硅基、取代或未取代的C6～C60的芳族稠环、取代或未取代的C1～C60的杂芳族稠环；当两个或以上相邻的R5至R7可以相互成环；n独立地为0至8的整数；m为1或2；*、**表示与N或C相连的位置。
更加优选地，式(I)中的环CY1独立地选自以下代表结构式的一种，但并不代表本发明限于以下结构：
Figure BDA0003107246660000031
其中，R8独立地选自CN、取代或未取代的C1～C60的烷基、取代或未取代的C2～C60的烯基、取代或未取代的C1～C60的环烷基、取代或未取代的C1～C60的杂烷基、取代或未取代的C6～C60的芳基、取代或未取代的C1～C60的杂芳基、取代或未取代的C1～C60的胺基、取代或未取代的C1～C60的硅基、取代或未取代的C6～C60的芳族稠环、取代或未取代的C1～C60的杂芳族稠环；Y、Z、R6、R7和n与上述的定义相同。
结合以上对CY1的描述，优选地，式(I)所示的化合物独立地选自以下代表结构的一种，但并不代表本发明限于以下结构：
Figure BDA0003107246660000041
其中，Y、Z、R8；X1至X3、R1至R7、Ar1、Ar2、n与上述的定义相同。
优选地，以上所述的结构式中，R1至R8独立选自氢、氘、卤素、CN外，还可以独立选自以下基团的一种或多种的组合，但并不代表本发明限于以下基团：
Figure BDA0003107246660000051
Figure BDA0003107246660000061
根据以上描述，特别优选地，本发明所述的一种有机化合物，选自以下代表结构式的一种，但并不代表本发明限于以下结构：
Figure BDA0003107246660000071
Figure BDA0003107246660000081
Figure BDA0003107246660000091
Figure BDA0003107246660000101
Figure BDA0003107246660000111
Figure BDA0003107246660000121
Figure BDA0003107246660000131
Figure BDA0003107246660000141
Figure BDA0003107246660000151
Figure BDA0003107246660000161
Figure BDA0003107246660000171
Figure BDA0003107246660000181
Figure BDA0003107246660000191
Figure BDA0003107246660000201
Figure BDA0003107246660000211
Figure BDA0003107246660000221
Figure BDA0003107246660000231
Figure BDA0003107246660000241
Figure BDA0003107246660000251
Figure BDA0003107246660000261
Figure BDA0003107246660000271
Figure BDA0003107246660000281
Figure BDA0003107246660000291
Figure BDA0003107246660000301
Figure BDA0003107246660000311
Figure BDA0003107246660000321
Figure BDA0003107246660000331
Figure BDA0003107246660000341
Figure BDA0003107246660000351
Figure BDA0003107246660000361
Figure BDA0003107246660000371
Figure BDA0003107246660000381
Figure BDA0003107246660000391
Figure BDA0003107246660000401
Figure BDA0003107246660000411
Figure BDA0003107246660000421
Figure BDA0003107246660000431
Figure BDA0003107246660000441
本发明还要求保护一种制剂，这种制剂包含式(I)所述化合物与一种或多种与溶剂形成，所用的溶剂没有特别限制，可以使用本领域技术人员熟知的例如甲苯、二甲苯、均三甲苯、四氢化萘、十氢萘、双环己烷、正丁基苯、仲丁基苯、叔丁基苯等不饱和烃溶剂、四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、溴戊烷、氯己烷、溴己烷、氯环己烷、溴环己烷等卤化饱和烃溶剂，氯苯、二氯苯、三氯苯等卤化不饱和烃溶剂，四氢呋喃、四氢吡喃等醚溶剂，苯甲酸烷基酯等酯类溶剂。
本发明要求保护一种有机发光元件，
包括：第一电极；
第二电极，与所述第一电极相面对；
有机功能层，夹设于所述第一电极和所述第二电极之间；
其中，有机功能层包含所述的有机化合物。
本发明优选地保护一种有机发光元件，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、电子传输层中至少一层，其中该器件的发光层中含有所述的有机化合物。
本发明所述的有机发光元件发光层中含有所述有机化合物和相应的客体材料，客体材料没由特别的限制，其中客体材料的质量百分数在1％-50％，客体材料没有任何限制，可以是荧光材料或磷光材料。
本发明还要求保护一种有机发光元件，该发光元件的发光层中含有所述有机化合物作为发光敏化剂及一种主体材料和一种客体材料形成的三元组合，其中本发明所述有机化合物的质量百分数在0.5％至50％；一种主体和客体材料之间的比例没有特别的要求。
本发明所述的有机化合物还可以与一种金属配合物共同形成电子传输，应用于有机发光元件，金属配合物没有特别限制，所述有机化合物的质量百分数在0.5％至70％。
在本发明中，有机发光元件是可以利用喷溅涂覆法、电子束蒸发、真空蒸镀等方法在基板上蒸镀金属或具有导电性的氧化物以及它们的合金形成阳极；在制备得到的阳极表面按顺序蒸镀空穴注入层、空穴传输层、发光层、空穴阻挡层和电子传输层，以后再蒸镀阴极的方法制备。本发明的有机发光元件可以分为顶发射、低发射或双面发射。
本发明的有机发光元件适用于构成显示、照明需求的各种电子产品。
本发明的涉及一种有机化合物，其主要特征是改善了此类有机化合物的单线态能级S1与三线态能级T1之间的差值(ΔST)，通过引入特别的环CY1，可以调节本发明所述有机化合物的ΔST≤0.35电子伏特。本发明的有机化合物具有高的发光效率，可产生热延迟荧光，明显提升主体和客体之间的能量传输和有机发光器件中三线态激子的利用效率；具体表现为使用本发明的有机化合物作为功能层，尤其作为发光层中的主体材料搭配合适的红光客体材料，与同类型但>0.37电子伏特的化合物相比，制作的有机发光器件其电流效率得到提升，操作电压适当降低，同时提升了有机发光元件的使用寿命，提供了一个创新的思路。
附图说明
图1为本发明有机电致发光二极管器件结构层图。
其中，110代表基板，120表示阳极，130表示空穴注入层，140表示空穴传输层，150表示发光层或活性层，160表示空穴阻挡层，170表示电子传输层，180表示电子注入层，190表示阴极。
图2为本发明化合物N-15和对比化合物RH-2的瞬态荧光光谱图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合具体实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
在本发明的一种优选实施方式中，本发明的OLED器件中含有空穴传输层，空穴传输材料可以优选自已知或未知的材料，特别优选地选自以下结构，但并不代表本发明限于以下结构：
Figure BDA0003107246660000461
在本发明的一种优选实施方式中，本发明的OLED器件中含有的空穴传输层，其包含一种或多种p型掺杂剂。本发明优选的p型掺杂剂为以下结构，但并不代表本发明限于以下结构：
Figure BDA0003107246660000471
本发明的一种优选实施方式中，所述的电子传输层可以选自化合物ET-1至ET-13的至少一种，但并不代表本发明限于以下结构：
Figure BDA0003107246660000472
电子传输层可以有机材料与一种或多种n型掺杂剂(如LiQ)共同形成。
用以下代表化学结构式说明本发明的创新点：
Figure BDA0003107246660000481
Figure BDA0003107246660000491
对比化合物RH-1～RH-6与本发明的代表化合物N-07至N-19-5的HOMO、LUMO、三线态能级、ΔST列于表1中：
表1
Figure BDA0003107246660000492
Figure BDA0003107246660000501
Figure BDA0003107246660000511
通过第三方定制获得以下中间体：
Figure BDA0003107246660000512
根据已有的文献和相关技术储备，本发明的有机化合物通用合成步骤如下：
Figure BDA0003107246660000513
通用合成步骤：在氮气氛下，将中间体1(10毫摩尔)、中间体2(10毫摩尔)、KOH(30毫摩尔)、DMF(120毫升)加热至130度，反应24小时。反应结束后，将混合物倒入冰水中，过滤，固体粗品用冰水、冷甲醇洗涤，干燥。用二氯甲烷/甲醇(100:1～10:1)过硅胶柱纯化得到本发明的目标有机化合物，产率及化合物的质谱鉴定结果如下：
化合物 中间体 产率 实测MS 理论MS
N-07 IN-07 67％ 748.3 748.26
N-09 IN-09 75％ 698.2 698.25
N-11 IN-11 78％ 724.3 724.26
N-13 IN-13 81％ 800.3 800.29
N-15 IN-15 81％ 774.3 774.28
N-16 IN-16 82％ 774.3 774.28
N-17 IN-17 78％ 814.3 814.27
N-18 IN-18 65％ 830.3 830.25
N-110 IN-110 86％ 840.3 840.33
N-115 IN-115 80％ 814.3 814.27
N-118 IN-118 77％ 856.3 856.30
N-119 IN-119 76％ 840.3 840.33
N-120 IN-120 75％ 814.3 814.27
N-11-2 IN-11-2 79％ 724.2 724.26
N-13-2 IN-13-2 78％ 800.3 800.29
N-15-2 IN-15-2 87％ 774.3 774.28
N-16-2 IN-16-2 83％ 774.3 774.28
N-17-2 IN-17-2 86％ 814.3 814.27
N-18-2 IN-18-2 74％ 830.3 830.25
N-110-2 IN-110-2 84％ 840.3 840.33
N-111-2 IN-111-2 78％ 814.3 814.27
N-118-2 IN-118-2 83％ 856.3 856.30
N-11-3 IN-11-3 79％ 724.3 724.26
N-14-3 IN-14-3 74％ 800.3 800.29
N-15-3 IN-15-3 72％ 774.3 774.28
N-16-3 IN-16-3 71％ 774.3 774.28
N-17-3 IN-17-3 76％ 814.3 814.27
N-18-3 IN-18-3 69％ 830.2 830.25
N-110-3 IN-110-3 74％ 840.3 840.33
N-111-3 IN-111-3 77％ 814.3 814.27
N-11-4 IN-11-4 84％ 724.3 724.26
N-15-4 IN-15-4 81％ 774.3 774.28
N-16-4 IN-16-4 80％ 774.3 774.28
N-18-4 IN-18-4 80％ 830.3 830.25
N-11-5 IN-11-5 67％ 715.2 715.24
N-12-5 IN-12-5 71％ 715.2 715.24
N-13-5 IN-13-5 72％ 715.2 715.24
N-14-5 IN-14-5 71％ 715.2 715.24
N-15-5 IN-15-5 65％ 715.2 715.24
N-16-5 IN-16-5 75％ 765.2 765.25
OLED器件实施例：
具体实施顶发射OLED器件的结构为在含有ITO/Ag/ITO的玻璃上，空穴注入层为HT-1:P-3(95:5v/v％)，厚度为10纳米；空穴传输层为HT-1，厚度为100纳米；电子阻挡层为HT-8，厚度为10纳米，发光层为[RH-1或RH-2或本发明的有机化合物]:RD-1(97:2v/v％)，厚度为35纳米，电子传输层为ET-13：LiQ(50:50v/v％)，厚度为35纳米，然后蒸镀阴极Yb为1纳米，Ag为14纳米，蒸镀CPL层为70纳米。
Figure BDA0003107246660000531
依据上述器件实施例，具有不同的发光层的OLED器件的电流效率、操作电压、寿命等特性综合于表2中。
表2
Figure BDA0003107246660000532
从表1中，对比化合物RH-1至RH-6与本发明的优选化合物具有十分接近的HOMO在-5.40至-5.60电子伏特之间，LUMO能级在-2.80至-3.10电子伏特之间，其三线态能级也比较接近，均在2.30-2.40电子伏特之间。但对比化合物RH-1至RH-6的单线态能级S1与三线态能级T1的差值ΔST在0.41至0.47电子伏特。发明人意外地发现，将RH-1至RH-6中连接的苯基、萘基或芴等换成本发明的环CY1后[代表化合物(表1)]发现它们的ΔST可以降低至0.35电子伏特以下。图2显示降低ΔST后，本发明的代表化合物N-15产生明显的热活化延迟荧光。根据现有的发光理论，本发明中的大部分有机化合物的ΔST低于0.35电子伏特的化合物，它们也可以产生热活化延迟荧光。用它们作为红光客体材料RD-1的主体，制备了器件例1至21，器件性能结果如表2所示。
从表2中，优选的器件例1至21与对比器件例1-2相比，器件的驱动电压有适当的降低，但其发光效率得到了明显的提升，器件的使用寿命也有延长。器件例3采用N-11作为主体，对比器件2采用RH-2作为主体，发现N-11仅比RH-2多了1个苯环，器件例3的电流效率达到了52.7cd/A，是对比器件2的129％，器件的寿命增加了106小时(55％)。特别地，器件例10的电流效率达到了对比器件2的135％，器件的使用寿命增加了60％，同时操作电压降低了0.3伏。
本发明的有机化合物N-07和N-09的ΔST在0.34eV，用它们作为主体的器件例1和2的电流效率为50.3和51.2cd/A，随着ΔST的降低，本发明中其他有机化合物的器件效果又有明显的提升。结合表1和表2的结果充分说明，本发明涉及的化合物为具有热活化延迟荧光的特性，把它们作为红光客体的主体构建有机发光器件的发光层，可以显著提升主客体之间的能量传输，从而降低器件的操作电压，提升效率和寿命。
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 (8)

1.一种有机化合物，其特征在于，所述有机化合物式独立选自以下代表结构的一种：
Figure FDA0003559679010000011
Figure FDA0003559679010000021
Figure FDA0003559679010000031
2.一种制剂，其特征在于，包含权利要求1所述的有机化合物和至少一种溶剂，所述溶剂为不饱和烃溶剂、卤化饱和烃溶剂、卤化不饱和烃溶剂或醚溶剂，
所述不饱和烃溶剂为甲苯、二甲苯、均三甲苯、四氢化萘、正丁基苯、仲丁基苯或叔丁基苯；
所述卤化饱和烃溶剂为四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、溴戊烷、氯己烷、溴己烷、氯环己烷或溴环己烷；
所述卤化不饱和烃溶剂为氯苯、二氯苯或三氯苯；
所述醚溶剂为四氢呋喃或四氢吡喃。
3.一种有机发光元件，其特征在于，包括：
第一电极；
第二电极，与所述第一电极相面对；
有机功能层，夹设于所述第一电极和所述第二电极之间；
其中，有机功能层包含权利要求1所述的有机化合物。
4.一种有机发光元件，包括阴极层、阳极层和有机功能层，该有机功能层包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层中至少一层，其特征在于，该元件的任一层中含有权利要求1所述的有机化合物。
5.根据权利要求3或4所述的有机发光元件，其特征在于，发光层中含有权利要求1所述有机化合物和相应的客体材料，其中所述客体材料的质量百分数在1％至50％，客体材料可以是荧光材料或磷光材料。
6.根据权利要求3或4所述的有机发光元件，其特征在于，发光层中含有权利要求1所述有机化合物作为发光敏化剂及一种主体材料和一种客体材料形成三元组合，所述有机化合物的质量百分数在0.5％至50％。
7.根据权利要求3或4所述的有机发光元件，其特征在于，电子传输层中含有权利要求1所述有机化合物和一种n型掺杂剂，所述有机化合物的质量百分数在0.5％至70％。
8.一种显示或照明装置，其特征在于，所述的显示或照明装置含有权利要求3或4所述的有机发光元件。
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