CN111533751A - 一种红色磷光主体化合物及使用该化合物的有机发光器件 - Google Patents

一种红色磷光主体化合物及使用该化合物的有机发光器件 Download PDF

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CN111533751A
CN111533751A CN202010226922.XA CN202010226922A CN111533751A CN 111533751 A CN111533751 A CN 111533751A CN 202010226922 A CN202010226922 A CN 202010226922A CN 111533751 A CN111533751 A CN 111533751A
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高春吉
叶绪兵
钱烨
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

本发明提供一种红色磷光化合物和使用该化合物的有机发光器件，具体涉及一种具有优异的色纯度、高亮度及发光效率的可溶性磷光主体化合物以及使用该化合物的OLED器件。本发明提供的红色磷光主体化合物结构如式1所示，其中L两边不同时链接喹唑啉复合体结构：
Figure DDA0002428003620000011
； 上述结构式1中，L独立地选自联苯、二苯并呋喃、二苯并噻吩、9,9‑二甲基芴、9,9‑烷基‑9H‑9‑硅杂芴、咔唑、9,10‑二氢‑9,9‑烷基吖啶、吩噻嗪；Ar1和Ar2各自独立地选自取代或未取代的C6‑C30芳基、取代或未取代的C2‑C30杂芳基；R1至R2独立的选自取代或未取代的烷基、取代或未取代的C6‑C60芳基、取代或未取代的C3‑C60含氮的杂芳基、或者是它们的组合中的一种。

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一种红色磷光主体化合物及使用该化合物的有机发光器件
技术领域
本发明涉及一种红色磷光主体化合物和使用该化合物的有机发光器件，更具体而言，涉及一种具有优异的色纯度和高亮度及发光效率的可溶性磷光主体化合物以及使用该化合物的OLED器件。
背景技术
随着多媒体技术的发展及信息化要求的提高，对面板显示器性能的要求越来越高。其中，OLED具有自主发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列的优点，在新一代显示器和照明技术中的潜在应用而引起广泛注意，应用前景十分广阔。有机电致发光器件是自发的发光器件，OLED发光的机理是在外加电场作用下，电子和空穴分别从正负两极注入后在有机材料中迁移、复合并衰减而产生发光。OLED的典型结构包括阴极层、阳极层、电子注入层、电子传输层、空穴阻挡层、空穴传输层、空穴注入层和有机发光层中的一种或几种功能层。
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，比如外量子效率(EQE)的提高，色纯度更高的新材料的设计与合成、高效电子传输/空穴阻挡新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。
发光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，但作为有机电致发光器件中的主体材料，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，如何设计新的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
本发明的目的是提供一种红色磷光主体化合物及其使用该化合物的有机发光器件，本发明的磷光化合物适于溶液工艺，具有优异的纯色度、高亮度和优异的发光效率
本发明提供一种红色磷光主体化合物，其特征在于：其结构式如1所示，
Figure BDA0002428003600000021
上述结构式1中，L独立地选自联苯、二苯并呋喃、二苯并噻吩、9,9-二甲基芴、9,9-烷基-9H-9-硅杂芴、咔唑、9,10-二氢-9,9-烷基吖啶、吩噻嗪；Ar1和Ar2各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基；R1和R2独立的选自取代或未取代的烷基、取代或未取代的C6-C60芳基、取代或未取代的C3-C60含氮的杂芳基、或者是它们的组合中的一种。
优选的，L独立地选自取代或未取代的苯基取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的
Figure BDA0002428003600000022
基、取代或未取代的咔唑基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的吡嗪基、取代或未取代的三嗪基、取代或未取代的苯并咪唑基、取代或未取代的吲哚基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的菲啰啉基、取代或未取代的吖啶基、取代或未取代的吩噻嗪基、取代或未取代的吩噁嗪基、取代或未取代的萘啶基、或者是它们的组合中的一种。
优选的，所述的Ar1、Ar2独立地选自取代或未取代的苯并呋喃、苯并噻吩、1,1-二烷基-1H-茚、2,3-苯并吡咯、苯并[b]硅烷、苯并噻嗪，取代或未取代的苯基取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的
Figure BDA0002428003600000023
基、取代或未取代的咔唑基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的吡嗪基、、取代或未取代的苯并咪唑基、取代或未取代的吲哚基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的菲啰啉基、取代或未取代的吖啶基、取代或未取代的吩噻嗪基、取代或未取代的吩噁嗪基、取代或未取代的萘啶基、或者是它们的组合中的一种。
进一步的优选的方式是，所述的红色磷光主体化合物中L独立地选自以下结构：
Figure BDA0002428003600000031
其中，R3、R4、R5独立地选自取代或未取代的C1-C16的烷基、取代或未取代的C6-C30芳基、C2-C30的取代或未取代的杂芳基。
进一步的优选的方式是，红色磷光主体化合物中Ar1嘧啶复合体和Ar2的嘧啶复合体独立地选自以下结构：
Figure BDA0002428003600000041
其中，R1、R2、R6、R7独立的选自取代或未取代的烷基、取代或未取代的C6～C60芳基、取代或未取代的C3～C60含氮的杂芳基、或者是它们的组合中的一种。
进一步的优选的方式是，所述的红色磷光主体化合物独立地选自下列化合物：
Figure BDA0002428003600000051
Figure BDA0002428003600000061
本发明还提供上述一种含嘧啶复合体的化合物在有机发光器件中的应用。
优选的，所述有机发光器件包括阳极、阴极以及位于阳极与阴极之间的若干个有机功能层，所述的有机功能层含有所述的一种含嘧啶复合体的化合物。
本发明的有益效果：
本发明提供一种含嘧啶复合体的化合物，该含嘧啶复合体的化合物具有式1所示结构，嘧啶复合体的化合物结构中的富电子的两个嘧啶链接结构整个化合物分子的光电性质产生很大的影响，有利于减少不必要的振动能量损失，实现高效的发光性能。通过调节取代基基团，使络合物具有更好的热稳定性和化学性质。本发明的一种含嘧啶复合体的化合物，制备方法简单，原料易得，能够满足工业化需求。
将嘧啶复合体的化合物制备成器件，尤其是作为主体材料，器件表现出驱动电压低、发光效率高的优点，优于现有常用OLED器件。
在本发明中，所述有机电致器件优选包括阳极、阴极以及位于阳极和阴极之间的若干个有机物层，所述“有机物层”指的是有机电致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，所述发光层为红色发光层时，采用上述所述的有机电致器件用化合物作为红色主体，可得到高效率、高分辨率、高亮度及长寿命的有机电致器件。
在本发明中，所述的红色磷光主体化合物的有机电致发光二极管器件，其特征在于，所述的有机电致发光器件包括顺次沉积的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极，所述红色磷光化合物作为主体材料。
本发明对所述有机电致器件的制备方法没有特殊的限制，除了使用式1的有机化合物之外，采用本领域技术人员熟知的发光器件的制备方法和材料制备得到即可。
附图说明
图1为有机电发光二极管发光色度和可见度关系图。表示随有机电致发光器件的色纯度增加(即随色度坐标的X值变得更大)可见度降低。
具体实施方式
为了使本发明实现的技术手段、创作特征、达成目的与功效易于明白了解，下面结合图示与具体实施例，进一步阐述本发明。
器件实施例中所用的各有机层化合物如下所示：
Figure BDA0002428003600000081
形成例
实施例1：化合物1的制备
中间体Sub-1的合成
Figure BDA0002428003600000082
在500mL反应瓶中加入中间体苯硼酸(7.49g,61.4mmol)，2,4-二溴噻唑(17.68g,61.4mmol)，四(三苯基膦)钯(5mol％)，K2CO3(17.0g,122.8mmol)，1,4-二氧六环(200mL)和水(50mL)。反应体系升温至80℃，氮气保护下反应12小时。反应完成后，将反应液冷却至室温，用邻二氯苯和水萃取。有机层用无水硫酸镁干燥、浓缩、重结晶所得粗品过硅胶柱得到中间体Sub-1(13.13g,产率75％)LC-MS：M/Z283.99(M+H)+。
中间体Sub-2的合成
Figure BDA0002428003600000083
在500mL反应瓶中加入[1,1'-联苯]-4,4'-二基二硼酸(5.12g,20.0mmol)，Sub-1(5.96g,20.9mmol)，碳酸钾(14.5g,104.6mmol)，四三苯基膦钯(2.4g,2.1mmol)，1,4-二氧六环(140mL)和水(70mL)。反应体系升温至60℃，氮气保护下反应十小时。将反应液倒入450mL甲醇中，过滤析出的固体。用氯苯溶解析出的固体，用装有硅藻土和硅胶粉的漏斗过滤。过滤得到的橙色液体浓缩蒸干并用甲醇重结晶得到中间体Sub-2(8.05g,产率65％)LC-MS：M/Z402.15(M+H)+。
化合物1的合成
Figure BDA0002428003600000091
在500mL反应瓶中加入Sub-2(8.05g,20.0mmol)，Sub-3(6.80g,20.9mmol)，碳酸钾(14.5g,104.6mmol)，四三苯基膦钯(2.4g,2.1mmol)，1,4-二氧六环(140mL)和水(70mL)。反应体系升温至60℃，氮气保护下反应十小时。将反应液倒入450mL甲醇中，过滤析出的固体。用氯苯溶解析出的固体，用装有硅藻土和硅胶粉的漏斗过滤。过滤得到的橙色液体浓缩蒸干并用甲醇重结晶得到中间体化合物1(7.83g,产率65％)LC-MS：M/Z602.21(M+H)+。
实施例2：化合物2的制备
中间体Sub-4的合成
Figure BDA0002428003600000092
在500mL反应瓶中加入2,4-二溴噻唑(12.04g,41.8mmol)，4-联苯硼酸(8.28g,41.8mmol)，碳酸钾(14.5g,104.6mmol)，四三苯基膦钯(2.4g,2.1mmol)，1,4-二氧六环(140mL)和水(70mL)。反应体系升温至60℃，氮气保护下反应十小时。将反应液倒入450mL甲醇中，过滤析出的固体。用氯苯溶解析出的固体，用装有硅藻土和硅胶粉的漏斗过滤。过滤得到的橙色液体浓缩蒸干并用甲醇重结晶得到中间体Sub-4(9.81g,产率65％)LC-MS：M/Z360.03(M+H)+。
中间体Sub-5的合成
Figure BDA0002428003600000101
在500mL反应瓶中加入[1,1'-联苯]-4,4'-二基二硼酸(5.12g,20.0mmol)，Sub-1(11.92g,20.9mmol)，碳酸钾(14.5g,104.6mmol)，四三苯基膦钯(2.4g,2.1mmol)，1,4-二氧六环(140mL)和水(70mL)。反应体系升温至60℃，氮气保护下反应十小时。将反应液倒入450mL甲醇中，过滤析出的固体。用氯苯溶解析出的固体，用装有硅藻土和硅胶粉的漏斗过滤。过滤得到的橙色液体浓缩蒸干并用甲醇重结晶得到中间体Sub-2(8.05g,产率65％)LC-MS：M/Z402.15(M+H)+。
化合物2的合成：
Figure BDA0002428003600000102
在500mL反应瓶中加入Sub-1(11.92g,41.8mmol)，Sub-4(24.01g,41.8mmol)，碳酸钾(14.5g,104.6mmol)，四三苯基膦钯(2.4g,2.1mmol)，1,4-二氧六环(140mL)和水(70mL)。反应体系升温至60℃，氮气保护下反应十小时。将反应液倒入450mL甲醇中，过滤析出的固体。用氯苯溶解析出的固体，用装有硅藻土和硅胶粉的漏斗过滤。过滤得到的橙色液体浓缩蒸干并用甲醇重结晶得到中间体化合物2(19.11g,产率66％)LC-MS：M/Z692.22(M+H)+。
实施例3：化合物50的制备
Figure BDA0002428003600000103
参考实施例2的方法合成化合物50，其他步骤均参考了实施例2的合成，得到化合物50(17.92g，产率59％)。LC-MS：M/Z726.24(M+H)+。
实施例4：化合物71的制备
Figure BDA0002428003600000111
参考实施例1的方法合成化合物71，其他步骤均参考了实施例1的合成，得到化合物71(15.26g,产率49％)。LC-MS：M/Z744.23(M+H)+。
实施例5：化合物96的制备
Figure BDA0002428003600000112
(14.38g，产率43％)。LC-MS：M/Z799.37(M+H)+。
器件实施方案
第一实施方案
把ITO玻璃基板图案化，以具有3mm×3mm的发光区域。然后洗涤图案化的ITO玻璃基板。
随后将该基板安放在真空室。标准压力设定为1×10-6托。此后，在ITO基板上以
Figure BDA0002428003600000113
化合物
Figure BDA0002428003600000114
和
Figure BDA0002428003600000115
的顺序形成有机物质的层。
第二实施方案
采用上述第一实施方案同样的方法制备第二实施方案的有机发光器件，仅把有机发光器件的主体材料层由第一实施方案化合物1替换为化合物2。
第三实施方案
采用上述第一实施方案同样的方法制备第三实施方案的有机发光器件，仅把有机发光器件的主体材料层由第一实施方案化合物1替换为化合物50。
第四实施方案
采用上述第一实施方案同样的方法制备第四实施方案的有机发光器件，仅把有机发光器件的主体材料层由第一实施方案化合物1替换为化合物71。
第五实施方案
采用上述第一实施方案同样的方法制备第五实施方案的有机发光器件，仅把有机发光器件的主体材料层由第一实施方案化合物1替换为化合物96。
对比例
采用上述第一实施方案同样的方法制备对比例的有机发光器件，仅把有机发光器件的主体材料层由第一实施方案化合物1替换为化合物RH-1。
制作的有机发光器件在10mA/cm2电流条件下测试电压、效率和寿命。
表1为本发明实施例和比较例制备得到的有机发光器件的性能检测结果。
表1
Figure BDA0002428003600000121
如表1所示，该器件在低电压下也高效率地运行。并且与对比例相比，实施方案的电流效率明显增加，另外寿命至少增加38％以上。
以上描述了本发明的基本原理、主要特征和本发明的优点。本行业的技术人员应该了解，本发明不受上述实施例的限制，上述实施例和说明书中描述的只是说明本发明的原理，在不脱离本发明精神和范围的前提下本发明还会有各种变化和改进，这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等同物界定。

Claims (7)

1.一种红色磷光主体化合物，其特征在于：其化合物的结构式如式1所示，
Figure FDA0002428003590000011
上述结构式1中，L独立地选自联苯、二苯并呋喃、二苯并噻吩、9,9-二甲基芴、9,9-烷基-9H-9-硅杂芴、咔唑、9,10-二氢-9,9-烷基吖啶、吩噻嗪；Ar1和Ar2各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C2-C30杂芳基；R1至R2独立的选自取代或未取代的烷基、取代或未取代的C6-C60芳基、取代或未取代的C3-C60含氮的杂芳基、或者是它们的组合中的一种。
2.根据权利要求1中所述的一种红色磷光主体化合物，其特征在于，L独立地选自取代或未取代的苯基取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的
Figure FDA0002428003590000012
基、取代或未取代的咔唑基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的吡嗪基、取代或未取代的三嗪基、取代或未取代的苯并咪唑基、取代或未取代的吲哚基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的菲啰啉基、取代或未取代的吖啶基、取代或未取代的吩噻嗪基、取代或未取代的吩噁嗪基、取代或未取代的萘啶基、或者是它们的组合中的一种。
3.根据权利要求1中所述的一种红色磷光主体化合物，其特征在于，Ar1和Ar2独立地选自取代或未取代的苯并呋喃、苯并噻吩、1,1-二烷基-1H-茚、2,3-苯并吡咯、苯并[b]硅烷、苯并噻嗪，取代或未取代的苯基取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的
Figure FDA0002428003590000013
基、取代或未取代的咔唑基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的吡嗪基、、取代或未取代的苯并咪唑基、取代或未取代的吲哚基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的菲啰啉基、取代或未取代的吖啶基、取代或未取代的吩噻嗪基、取代或未取代的吩噁嗪基、取代或未取代的萘啶基、或者是它们的组合中的一种。
4.根据权利要求1所述的红色磷光主体化合物，其特征在于，所述的L独立地选自以下结构：
Figure FDA0002428003590000021
其中，R3、R4、R5独立地选自取代或未取代的C1-C16的烷基、取代或未取代的C6-C30芳基、C2-C30的取代或未取代的杂芳基。
5.根据权利要求1所述的红色磷光主体化合物，其特征在于，所述的Ar1嘧啶复合体和Ar2的嘧啶复合体独立地选自以下结构：
Figure FDA0002428003590000031
其中，R1、R2、R6、R7独立的选自取代或未取代的烷基、取代或未取代的C6～C60芳基、取代或未取代的C3～C60含氮的杂芳基、或者是它们的组合中的一种。
6.根据权利要求1-5中任意一权利要求所述的红色磷光主体化合物，其特征在于，所述的红色磷光主体化合物独立地选自下列化合物：
Figure FDA0002428003590000041
Figure FDA0002428003590000051
7.一种使用权利要求1-6中任意一权利要求所述的红色磷光主体化合物的有机电致发光二极管器件，其特征在于，所述的有机电致发光器件包括顺次沉积的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极，所述红色磷光化合物作为主体材料。
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