CN115141144A - 一种有机化合物、有机电致发光器件及其应用 - Google Patents

一种有机化合物、有机电致发光器件及其应用 Download PDF

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CN115141144A
CN115141144A CN202210615961.8A CN202210615961A CN115141144A CN 115141144 A CN115141144 A CN 115141144A CN 202210615961 A CN202210615961 A CN 202210615961A CN 115141144 A CN115141144 A CN 115141144A
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CN115141144B (zh
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邓东阳
刘营
代文朋
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Wuhan Tianma Microelectronics Co Ltd
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Abstract

本发明提供一种有机化合物、有机电致发光器件及其应用，所述有机化合物具有如式I所示结构，其含有特殊的稠环母核结构，通过分子结构的设计，使所述有机化合物具有适宜的HOMO能级和LUMO能级，单线态能级较高，光电性能优异，而且玻璃化转变温度适宜，热稳定性和成膜性优异，易形成稳定均一的薄膜，保持器件的稳定性。所述有机化合物用于OLED器件，能够与相邻层材料的能级相匹配，具有较高的载流子传输速率以及平衡的载流子传输性能，能够获得较宽的载流子复合区域，从而提升器件发光效率和寿命，降低器件的电压，使OLED器件具有更加优异的综合性能。

Description

一种有机化合物、有机电致发光器件及其应用
技术领域
本发明属于有机电致发光材料技术领域，具体涉及一种有机化合物、有机电致发光器件及其应用。
背景技术
有机电致发光器件(Organic Light Emitting Diode，OLED)作为新一代显示技术，具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点，近年来获得长足发展，已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
OLED器件通常包括阴极、阳极以及位于两电极之间的有机层。有机层是OLED器件的核心部分，包括发光层，以及电子传输层、空穴传输层、空穴注入层和电子注入层等辅助传输的功能层。通电时，电子和空穴被分别注入、传输到发光区域并复合，从而产生激子并发光。
OLED器件中的发光材料按发光机理可分为电致荧光和电致磷光两种，电致荧光是单重态激子的辐射衰减跃迁，电致磷光则是三重态激子辐射衰减到基态所发射的光。根据自旋量子统计理论，单重态激子和三重态激子的形成概率比例是1:3，因此荧光材料的内量子效率不超过25％的限制，外量子效率普遍低于5％。电致磷光材料的内量子效率理论上可以达到100％，外量子效率可以达到20％。1998年，吉林大学的马於光教授和美国普林斯顿大学的Forrest教授分别报道了采用锇配合物和铂配合物作为发光染料掺杂入发光层，第一次成功得到并解释了磷光电致发光现象，并开创性地将所制备磷光材料应用于电致发光器件。
由于磷光重金属材料有较长的寿命，可以达到μs的级别，其在高电流密度下，可能导致三线态-三线态湮灭和浓度淬灭，造成器件性能衰减，因此通常将重金属磷光材料掺杂到合适的主体材料中，形成一种主客体掺杂体系，使得能量传递最优化，发光效率和寿命最大化。在目前的研究现状中，重金属掺杂材料商业化已成熟，很难开发可替代的掺杂材料。因此，把重心放在研发磷光主体材料是研究者们共通的思路。
随着显示技术的发展，人们对OLED器件的显示性能和光电性质提出了更高的要求。但是，目前使用的主体材料在发光效率、驱动电压、稳定性、工作寿命、加工性能等方面的表现还难以满足OLED器件的性能要求。因此，开发更多种类、更高性能的有机电致发光材料，是本领域亟待解决的问题。
发明内容
为了开发更多种类、更高性能的有机电致发光材料，本发明的目的之一在于提供一种有机化合物，所述有机化合物具有如式I所示结构：
Figure BDA0003673332200000021
式I中，L1、L2各自独立地选自单键、C6-C30亚芳基或C3-C30亚杂芳基中的任意一种。
式I中，R1、R2、R3各自独立地选自卤素、氰基、取代或未取代的C1-C30直链或支链烷基、取代或未取代的C3-C30环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C6-C30芳胺基、取代或未取代的C6-C30芳基酮基、取代或未取代的C3-C30杂芳基酮基、取代或未取代的C6-C30芳基砜基、取代或未取代的C6-C30芳基硼基中的任意一种。
式I中，n1、n2各自独立地选自0-3的整数，例如可以为0、1、2或3；n3选自0-2的整数，例如可以为0、1或2；n1、n2和n3不同时为0。
本发明提供的有机化合物具有式I所示的结构，其含有特殊的稠环母核，使化合物表现出适宜的HOMO能级和LUMO能级，单线态能级较高，光电性能优异，而且具有适宜的玻璃化转变温度和优异的热稳定性，易形成良好的无定形薄膜，适于OLED器件的加工和使用。所述有机化合物用于OLED器件(有机电致发光器件)，能够与相邻层材料的能级相匹配，有效地传输电荷，并将空穴和激子限制在发光区，利于扩宽发光区域，从而提升器件发光效率和寿命，降低器件的电压和能耗。
本发明中，所述C6-C30均可以为C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
所述C3-C30均可以为C3、C4、C5、C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
所述C1-C30均可以为C1、C2、C3、C4、C5、C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
本发明中，所述卤素均可以为F、Cl、Br或I。
本发明的目的之二在于提供一种有机电致发光器件，所述有机电致发光器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机层，所述有机层包括至少一种目的之一所述的有机化合物。
本发明的目的之三在于提供一种显示面板，所述显示面板包括如目的之二所述的有机电致发光器件。
本发明的目的之四在于提供一种显示装置，所述显示装置包括如目的之三所述的显示面板。
相对于现有技术，本发明具有以下有益效果：
本发明提供的有机化合物中含有特殊的稠环母核结构，通过分子结构的设计，使所述有机化合物具有适宜的HOMO能级和LUMO能级，单线态能级较高，光电性能优异，而且玻璃化转变温度适宜，热稳定性和成膜性优异，易形成稳定均一的薄膜，保持器件的稳定性。所述有机化合物用于OLED器件，能够与相邻层材料的能级相匹配，具有较高的载流子传输速率和平衡的载流子传输性能，能够获得较宽的载流子复合区域，从而提升器件发光效率和寿命，降低器件的驱动电压，使OLED器件具有更加优异的综合性能。
附图说明
图1为本发明一个实施方式中提供的OLED器件的结构示意图；
图2为本发明另一实施方式中提供的OLED器件的结构示意图；
其中，110-阳极，120-第一有机薄膜层，121-第一空穴传输层，122-第二空穴传输层，130-发光层，140-第二有机薄膜层，141-第一电子传输层，142-第二电子传输层，150-阴极，160-基板，170-盖帽层。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了，所述实施例仅仅是帮助理解本发明，不应视为对本发明的具体限制。
在一个实施方式中，本发明提供一种有机化合物，所述有机化合物具有如式I所示结构：
Figure BDA0003673332200000031
式I中，L1、L2各自独立地选自单键、C6-C30亚芳基或C3-C30亚杂芳基中的任意一种；当L1为单键时，代表基团R1与稠环母核通过单键直接相连；当L2为单键时，代表基团R2与稠环母核通过单键直接相连。
式I中，R1、R2、R3各自独立地选自卤素、氰基、取代或未取代的C1-C30直链或支链烷基、取代或未取代的C3-C30环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C6-C30芳胺基、取代或未取代的C6-C30芳基酮基、取代或未取代的C3-C30杂芳基酮基、取代或未取代的C6-C30芳基砜基、取代或未取代的C6-C30芳基硼基中的任意一种。
式I中，n1、n2分别代表
Figure BDA0003673332200000032
的数目，各自独立地选自0-3的整数，例如可以为0、1、2或3。
式I中，n3代表取代基R3的数目，选自0-2的整数，例如可以为0、1或2。
式I中，n1、n2和n3不同时为0。
本发明提供的有机化合物具有式I所示结构，其以包含菲环和萘环的特殊稠环作为母核结构，使化合物具有适宜的HOMO和LUMO能级，单线态能级较高，光电性能优异，而且具有优良的热稳定性和成膜性，玻璃化转变温度Tg适宜，利于在热真空蒸镀过程中形成稳定、均一的薄膜，同时减少相分离，保持器件的稳定性，适于OLED器件的加工和使用。
所述有机化合物用于OLED器件，尤其适用于发光层材料和/或电子传输层材料(ETL)，能够与相邻层材料的能级相匹配，有效地传输电荷。所述有机化合物作为发光材料(磷光主体材料)，具有较高的载流子传输速率以及平衡的载流子传输性能，以利于器件中空穴和电子传输的平衡同时获得较宽的载流子复合区域，提高发光效率，而且能够延长器件的工作寿命，降低器件的电压和能耗。
本发明中，Ca-Cb的表达方式代表该基团具有的碳原子数为a-b，若无特殊说明，该碳原子数不包括取代基的碳原子数。
本发明中，对于化学元素的表述包含化学性质相同的同位素，例如，氢(H)则包括1H(氕)、2H(氘，D)、3H(氚，T)等；碳(C)则包括12C、13C等。
本发明中，所述C6-C30均可以为C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
所述C3-C30均可以为C3、C4、C5、C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
所述C1-C30均可以为C1、C2、C3、C4、C5、C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
本发明中，所述卤素均可以为F、Cl、Br或I。
具体地，所述C6-C30芳基可以为C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等的芳基；示例性地包括但不限于：苯基、联苯基、三联苯基、萘基、蒽基、菲基、茚基、芴基及其衍生物(9,9-二甲基芴基、9,9-二乙基芴基、9,9-二苯基芴基、9,9-二萘基芴基、螺二芴基、苯并芴基等)、荧蒽基、三亚苯基、芘基、苝基、
Figure BDA0003673332200000041
基或并四苯基等。
所述C3-C30杂芳基可以为C3、C4、C5、C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等的杂芳基，其中的杂原子包括O、S、N、P或B等；示例性地包括但不限于：呋喃基、噻吩基、吡咯基、吡啶基、吡嗪基、哒嗪基、嘧啶基、三嗪基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、噌啉基、邻菲罗啉基、咪唑基、噻唑基、恶唑基、苯并咪唑基、苯并噻唑基、苯并恶唑基、苯并呋喃基、苯并噻吩基、吲哚基、二苯并呋喃基、二苯并噻吩基、氮杂二苯并呋喃基、氮杂二苯并噻吩基、咔唑基及其衍生物(N-苯基咔唑基、N-萘基咔唑基、苯并咔唑基、二苯并咔唑基、吲哚并咔唑基、氮杂咔唑基等)、吩噻嗪基、吩恶嗪基、氢化吖啶基及其衍生物等。
所述C6-C30(例如C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等)亚芳基的具体示例，可以为上述芳基中去掉一个氢原子而得到的二价基团；所述C3-C30(例如C3、C4、C5、C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等)亚杂芳基的具体示例，可以为上述杂芳基中去掉一个氢原子而得到的二价基团。
本发明中，所述C6-C30(例如C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等)芳基酮基的具体示例，为
Figure BDA0003673332200000051
(酮基)与上述列举的芳基相连形成的一价基团；所述C3-C30(例如C3、C4、C5、C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等)杂芳基酮基的具体示例，为
Figure BDA0003673332200000052
(酮基)上述列举的杂芳基相连形成的一价基团；所述C6-C30(例如C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等)芳基砜基的具体示例，为
Figure BDA0003673332200000053
(砜基)与上述列举的芳基相连形成的一价基团；所述C6-C30(例如C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等)芳基硼基的具体示例，为-BH2中的至少一个H被上述列举的芳基取代而形成的一价基团。所述C6-C30(例如C6、C9、C10、C12、C14、C16、C18、C20、C22、C24、C26或C28等)芳胺基的具体示例，为-NH2中的至少一个H被上述列举的芳基取代而形成的一价基团。
需要说明的是，芳基酮基中的酮基数目≥1(例如1、2或3等)，芳基砜基中的砜基数目≥1(例如1、2或3等)。
所述C1-C30直链或支链烷基可以为C1、C2、C3、C4、C5、C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等的直链或支链烷基，示例性地包括但不限于：甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基、正辛基、正庚基、正壬基、正癸基等。
所述C1-C30(例如C1、C2、C3、C4、C5、C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等)烷氧基的具体示例，为O与上述列举的直链或支链烷基相连形成的一价基团。
所述C3-C30环烷基可以为C3、C4、C5、C6、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等的环烷基；示例性地包括但不限于：环丙基、环丁基、环戊基、环己基、金刚烷基等。
本发明中，所述“取代或未取代”的基团，可以取代有一个取代基，也可以取代有多个取代基，当取代基为多个(至少2个)时，多个(至少2个)为相同或不同的基团；取代基可以连接在基团中任意可以连接的位置。下文涉及到相同的表达方式时，均具有同样的含义。
在一个实施方式中，R1、R2、R3中所述取代的取代基各自独立地选自卤素、氰基、未取代或R'取代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)直链或支链烷基、未取代或R'取代的C3-C10(例如C4、C5、C6、C7、C8或C9等)环烷基、未取代或R'取代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)烷氧基、未取代或R'取代的C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、未取代或R'取代的C3-C20(例如C3、C4、C5、C6、C9、C10、C12、C14、C16或C18等)杂芳基、未取代或R'取代的C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基中的至少一种。
R'选自卤素、氰基、C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)直链或支链烷基、C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C3-C20(例如C3、C4、C5、C6、C9、C10、C12、C14、C16或C18等)杂芳基或C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基中的至少一种。
在一个实施方式中，所述有机化合物具有如式IA或式IB所示结构：
Figure BDA0003673332200000061
其中，L1、L2、R1、R2、R3、n1、n2具有与式I中相同的限定范围。
在一个实施方式中，所述L1、L2各自独立地选自单键、亚苯基
Figure BDA0003673332200000062
亚联苯基
Figure BDA0003673332200000063
亚萘基
Figure BDA0003673332200000064
亚吡啶基
Figure BDA0003673332200000065
或亚嘧啶基
Figure BDA0003673332200000071
中的任意一种；虚线代表基团的连接位点。
在一个实施方式中，所述R1、R2、R3各自独立地选自卤素、氰基、未取代或卤代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)直链或支链烷基、未取代或卤代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)烷氧基、取代或未取代的C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、取代或未取代的C3-C20(例如C3、C4、C5、C6、C9、C10、C12、C14、C16或C18等)杂芳基、取代或未取代的C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基、C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基酮基、C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基砜基中的任意一种。
R1、R2、R3中所述取代的取代基各自独立地选自卤素、氰基、未取代或卤代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)直链或支链烷基、C3-C10(例如C4、C5、C6、C7、C8或C9等)环烷基、未取代或卤代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)烷氧基、C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C3-C20(例如C3、C4、C5、C6、C9、C10、C12、C14、C16或C18等)杂芳基或C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基中的至少一种。
在一个实施方式中，所述R1、R2、R3各自独立地选自卤素、氰基、未取代或卤代的C1-C6直链或支链烷基、未取代或卤代的C1-C6烷氧基、
Figure BDA0003673332200000072
Figure BDA0003673332200000073
Figure BDA0003673332200000081
其中，X1、X3各自独立地选自O、S、N-R13或CR13R14中的任意一种。
X2选自CR13R14、
Figure BDA0003673332200000082
中的任意一种。
R11、R12各自独立地选自卤素、氰基、未取代或卤代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)直链或支链烷基、C3-C10(例如C4、C5、C6、C7、C8或C9等)环烷基、未取代或卤代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)烷氧基、C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C3-C20(例如C3、C4、C5、C6、C9、C10、C12、C14、C16或C18等)杂芳基或C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基中的任意一种。
R13、R14各自独立地选自氢、卤素、氰基、未取代或卤代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)直链或支链烷基、C3-C10(例如C4、C5、C6、C7、C8或C9等)环烷基、未取代或卤代的C1-C10(例如C2、C3、C4、C5、C6、C7、C8或C9等)烷氧基、C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C3-C20(例如C3、C4、C5、C6、C9、C10、C12、C14、C16或C18等)杂芳基或C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基中的任意一种。
m1、m2代表取代基R11、R12的数目，各自独立地选自0-3的整数，例如可以为0、1、2或3；当m1≥2时，多个R11为相同或不同的基团；当m2≥2时，多个R12为相同或不同的基团。
虚线代表基团的连接位点。
在一个实施方式中，所述R1、R2、R3各自独立地选自卤素、氰基、未取代或卤代的C1-C6(例如C2、C3、C4或C5等)直链或支链烷基、未取代或卤代的C1-C6(例如C2、C3、C4或C5等)烷氧基、
Figure BDA0003673332200000091
Figure BDA0003673332200000092
Figure BDA0003673332200000101
Figure BDA0003673332200000102
其中，虚线代表基团的连接位点。
R21、R22各自独立地选自氰基、C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C3-C20(例如C3、C4、C5、C6、C9、C10、C12、C14、C16或C18等)杂芳基、未取代或卤代的C1-C6(例如C2、C3、C4或C5等)直链或支链烷基中的任意一种。
R23、R24各自独立地选自氢、氰基、C6-C20(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C3-C20(例如C3、C4、C5、C6、C9、C10、C12、C14、C16或C18等)杂芳基、未取代或卤代的C1-C6(例如C2、C3、C4或C5等)直链或支链烷基中的任意一种。
在一个实施方式中，所述R21、R22各自独立地选自氰基、未取代或卤代的C1-C6(例如C2、C3、C4或C5等)直链或支链烷基、
Figure BDA0003673332200000103
Figure BDA0003673332200000111
中的任意一种；前述基团可选地被全部氘代或部分氘代。
在一个实施方式中，所述R23、R24各自独立地选自氢、氰基、
Figure BDA0003673332200000112
Figure BDA0003673332200000113
Figure BDA0003673332200000114
中的任意一种；前述基团可选地被全部氘代或部分氘代。
在一个实施方式中，所述n1、n2各自独立地为0或1。
在一个实施方式中，所述n1+n2＝1。
在一个实施方式中，所述n1为0，所述n2为1，所述R2为吸电子基团；或，所述n1为1，所述n2为0，所述R1为吸电子基团。
所述“吸电子基团”意指能够降低苯环上电子云密度的基团，示例性地包括但不限于：氰基取代的C6-C30芳基、C3-C30氮杂芳基、C6-C30芳基酮基、C6-C30芳基砜基等。
在一个实施方式中，所述R1、R2、R3中的至少一个为吸电子基团。
在一个实施方式中，所述R1、R2、R3中的一个为吸电子基团。
在一个实施方式中，式I所示结构中含有一个吸电子基团(R1、R2、R3中的一个)，通过吸电子基团与母核的复配，使所述有机化合物具有较深的LUMO能级，从而降低电子传输的势垒，提高电子的注入能力，有效降低OLED器件的驱动电压。
在一个实施方式中，所述R1、R2、R3中还包括供电子基团。
所述“供电子基团”意指能够提高苯环上电子云密度的基团，示例性地包括但不限于：咔唑基及其衍生物、芳胺基、吩噻嗪基、吩噁嗪基、氢化吖啶基等。
在一个实施方式中，所述有机化合物选自如下化合物H1-H162中的任意一种：
Figure BDA0003673332200000121
Figure BDA0003673332200000131
Figure BDA0003673332200000141
Figure BDA0003673332200000151
Figure BDA0003673332200000161
Figure BDA0003673332200000171
Figure BDA0003673332200000181
在一个实施方式中，本发明提供一种有机电致发光器件，所述有机电致发光器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机层，所述有机层包括至少一种目的之一所述的有机化合物。
在一个实施方式中，所述有机层包括发光层，所述发光层包括至少一种(例如一种或两种)如目的之一所述的有机化合物。
在一个实施方式中，所述有机化合物作为发光层的磷光主体材料。
在一个实施方式中，所述有机化合物可单独作为发光层的磷光主体材料，即所述发光层的磷光主体材料只有一种所述有机化合物；也可将至少两种所述有机化合物复配作为磷光主体材料。
在一个实施方式中，所述OLED器件的有机薄膜层包括至少一层发光层(EML)和设置于发光层两侧的其他功能层，包括电子传输层(ETL)、空穴传输层(HTL)、空穴注入层(HIL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子注入层(EIL)中的任意一种或至少两种的组合，其中空穴/电子注入及传输层可以为咔唑类化合物、芳胺类化合物、苯并咪唑类化合物及金属化合物等。所述OLED器件的阴极上(远离阳极的一侧)还可以任选地设置盖帽层(CPL)。
在一个实施方式中，所述有机层包括发光层以及设置于所述发光层与阳极之间的空穴传输区，所述空穴传输区包括至少一种如目的之一所述的有机化合物。
在一个实施方式中，所述有机层包括发光层以及设置于所述发光层与阴极之间的电子传输区，所述电子传输区包括至少一种如目的之一所述的有机化合物。
在一个实施方式中，所述OLED器件的阳极材料可以为金属、金属氧化物或导电性聚合物；其中，所述金属包括铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金，所述金属氧化物包括氧化铟锡(ITO)、氧化铟锌(IZO)、氧化锌、氧化铟镓锌(IGZO)等，所述导电性聚合物包括聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除以上有助于空穴注入的材料及其组合，还包括已知的适合做阳极的材料。
在一个实施方式中，所述OLED器件的阴极材料可以为金属或多层金属材料；其中，所述金属包括铝、镁、银、铟、锡、钛等及它们的合金，所述多层金属材料包括LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合，还包括已知的适合做阴极的材料。
在一个实施方式中，所述OLED器件的结构示意图如图1所示，包括阳极110和阴极150，设置于所述阳极110和阴极150之间的发光层130，在发光层130的两侧设置有第一有机薄膜层120和第二有机薄膜层140，所述第一有机薄膜层120为空穴传输区，包括空穴传输层(HTL)、空穴注入层(HIL)或电子阻挡层(EBL)中的任意一种或至少两种的组合，所述第二有机薄膜层140为电子传输区，包括电子传输层(ETL)、空穴阻挡层(HBL)或电子注入层(EIL)中的任意一种或至少两种的组合。
在一个实施方式中，所述发光层130中包括至少一种本发明提供的有机化合物。
可选地，所述阴极150上(远离110的一侧)还可以设置盖帽层(CPL)。
所述OLED器件可以通过以下方法制备：在透明或不透明的光滑的基板上形成阳极，在阳极上形成有机薄层，在有机薄层上形成阴极。其中，形成有机薄层可采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明的目的之三在于提供一种显示面板，所述显示面板包括如目的之二所述的有机电致发光器件。
本发明的目的之四在于提供一种显示装置，所述显示装置包括如目的之三所述的显示面板。
在一个实施方式中，本发明提供的有机化合物可以通过如下合成路线制备得到：
Figure BDA0003673332200000201
Figure BDA0003673332200000202
其中，L1、L2、R1、R2具有与式I相同的限定范围；Me代表甲基；该合成路线得到具有式IB所示结构的化合物。
式IB所示结构的化合物按照如下合成路线可获得当n3为1的所述有机化合物，R3具有与式I相同的限定范围：
Figure BDA0003673332200000203
以下示例性地列举几种本发明所述有机化合物的制备实施例：
制备例1
含母核结构的中间体F的合成：
Figure BDA0003673332200000204
Figure BDA0003673332200000211
(1)化合物B的合成
将70.9mmol化合物A、141.8mmol双(频哪醇合)二硼、2.13mmol双(三苯基膦)二氯化钯(II)PdCl2(PPh3)2和212.7mmol乙酸钾(KOAc)添加到350mL的1,4-二噁烷中，充分溶解。之后，将混合物回流100min。在反应完成之后，将有机层用乙酸乙酯EA/水萃取，并且之后通过柱色谱法分离以获得化合物B。
(2)化合物D的合成
在烧瓶中，将55.1mmol化合物B、56.7mmo化合物C、2.76mmol四三苯基膦钯Pd(PPh3)4和137.8mmol K2CO3溶解在280mL的甲苯中，回流24h。在反应完成之后，将有机层用EA/水萃取，并且之后通过柱色谱法分离以获得化合物D。
(3)化合物E的合成
在烧瓶中，将41.0mmol化合物D和61.6mmol化合物d溶解在200mL的四氢呋喃(THF)中，并且然后将61.6mmol叔丁醇钾(KOtBu，在THF中)滴加到烧瓶中，并将混合物搅拌2h。在反应完成之后，将有机层用EA/水萃取，并且之后通过柱色谱法分离以获得化合物E。
(4)中间体F的合成
在烧瓶中，将41.0mmol化合物E溶解在200mL的氯苯中，然后将7.0mL的伊顿试剂(Eaton's reagent)添加到混合物中，回流7h。在反应完成之后，将有机层用EA/水萃取，之后通过柱色谱法分离以获得中间体F。
实施例1
一种有机化合物H2，结构为
Figure BDA0003673332200000212
该有机化合物H2的制备方法包括如下步骤：
Figure BDA0003673332200000213
在氮气保护下，向反应瓶中加入170mmol中间体F、170mmol化合物G2、480mL甲苯、240mL乙醇、120mL水和360mmol碳酸钾，滴加完毕后搅拌并加热升温至55℃，然后迅速加入3.33mmol Pd(PPh3)4和33.25mmol四丁基溴化铵(TBAB)，滴加完毕后，继续升温至75℃回流反应20h，反应完毕，降温，用二氯甲烷萃取，有机相水洗至中性，干燥，过滤，浓缩。用乙酸乙酯和正庚烷混合溶剂重结晶后烘干得到目标产物H2。
通过基质辅助激光解吸电离飞行时间质谱分析得到MALDI-TOF：m/z计算值：C31H17N，403.14；m/z实测值：403.42。
化合物元素分析结果(％)：计算值：C 92.28，H 4.25，N 3.47；测试值：C 92.25，H4.26，N 3.48。
实施例2
一种有机化合物H22，结构为
Figure BDA0003673332200000221
该有机化合物H22的制备方法包括如下步骤：
Figure BDA0003673332200000222
在氮气保护下，向反应瓶中加入170mmol中间体F、170mmol化合物G22、480mL甲苯、240mL乙醇、120mL水和360mmol碳酸钾，滴加完毕后搅拌并加热升温至60℃，然后迅速加入3.33mmol Pd(PPh3)4和33.25mmol TBAB，滴加完毕后，继续升温至72℃回流反应20h，反应完毕，降温，用二氯甲烷萃取，有机相水洗至中性，干燥，过滤，浓缩。用乙酸乙酯和正庚烷混合溶剂重结晶后烘干得到目标产物H22。
MALDI-TOF：m/z计算值：C43H25N，555.20；m/z实测值：555.57。
化合物元素分析结果(％)：计算值C 92.94，H 4.53，N 2.52；测试值：C 92.96，H4.52，N 2.52。
实施例3
一种有机化合物H54，结构为
Figure BDA0003673332200000223
该有机化合物H54的制备方法如下：
Figure BDA0003673332200000231
与实施例1的区别仅在于，将化合物G2替换为等摩尔量的化合物G54，其他原料、用量及工艺参数均与实施例1相同，得到目标产物H54。
MALDI-TOF：m/z计算值：C44H26N2，582.21；m/z实测值：582.53。
化合物元素分析结果(％)：计算值：C 90.69，H 4.50，N 4.81；测试值：C 90.67，H4.51，N 4.82。
实施例4
一种有机化合物H66，结构为
Figure BDA0003673332200000232
该有机化合物H66的制备方法包括如下步骤：
Figure BDA0003673332200000233
与实施例1的区别仅在于，将化合物G2替换为等摩尔量的化合物G66，其他原料、用量及工艺参数均与实施例1相同，得到目标产物H66。
MALDI-TOF：m/z计算值：C42H24N2，556.19；m/z实测值：556.26。
化合物元素分析结果(％)：计算值：C 90.62，H 4.35，N 5.03；测试值：C 90.64，H4.34，N 5.02。
实施例5
一种有机化合物H82，结构为
Figure BDA0003673332200000241
该有机化合物H82的制备方法包括如下步骤：
Figure BDA0003673332200000242
与实施例1的区别仅在于，将化合物G2替换为等摩尔量的化合物G82，其他原料、用量及工艺参数均与实施例1相同，得到目标产物H82。
MALDI-TOF：m/z计算值：C42H24N2，556.19；m/z实测值：556.37。
化合物元素分析结果(％)：计算值：C 90.62，H 4.35，N 5.03；测试值：C 90.61，H4.36，N 5.03。
实施例6
一种有机化合物H94，结构为
Figure BDA0003673332200000243
该有机化合物H94的制备方法包括如下步骤：
Figure BDA0003673332200000244
与实施例1的区别仅在于，将化合物G2替换为等摩尔量的化合物G94，其他原料、用量及工艺参数均与实施例1相同，得到目标产物H94。
MALDI-TOF：m/z计算值：C45H27N3，609.22；m/z实测值：609.48。
化合物元素分析结果(％)：计算值：C 88.64，H 4.46，N 6.89；测试值：C 88.66，H4.45，N 6.88。
实施例7
一种有机化合物H119，结构为
Figure BDA0003673332200000251
该有机化合物H119的制备方法包括如下步骤：
Figure BDA0003673332200000252
与实施例1的区别仅在于，将化合物G2替换为等摩尔量的化合物G119，其他原料、用量及工艺参数均与实施例1相同，得到目标产物H119。
MALDI-TOF：m/z计算值：C44H22D4N2，586.23；m/z实测值：586.47。
化合物元素分析结果(％)：计算值：C 90.07，H 5.15，N 4.77；测试值：C 90.09，H5.15，N 4.76。
实施例8
一种有机化合物H156，结构为
Figure BDA0003673332200000253
该有机化合物H156的制备方法包括如下步骤：
Figure BDA0003673332200000261
(1)化合物H155-1的合成
在氮气保护下，向反应瓶中加入170mmol中间体F、170mmol化合物G155、480mL甲苯、240mL乙醇、120mL水和360mmol碳酸钾，滴加完毕后搅拌并加热升温至58℃，然后迅速加入3.33mmol Pd(PPh3)4和33.25mmol TBAB，滴加完毕后，继续升温至75℃回流反应20h，反应完毕，降温，用二氯甲烷萃取，有机相水洗至中性，干燥，过滤，浓缩。用乙酸乙酯和正庚烷混合溶剂重结晶后烘干得到H155-1。
(2)H155-2的合成
在氮气流下，加入4.27mmol化合物H155-1、4.70mmol N-溴代琥珀酰亚胺(NBS)和40mL二氯甲烷，在60℃下搅拌15h。反应完成后，混合物用二氯甲烷萃取，然后用无水MgSO4除去有机层中的水分，再除去溶剂并通过柱色谱法(己烷/二氯甲烷＝9/1)进行纯化，得到H155-2。
(3)H155的合成
在氮气保护下，向反应瓶中加入170mmol化合物H155-2、170mmol化合物G155-1、480mL甲苯、240mL乙醇、120mL水、360mmol碳酸钾，滴加完毕后搅拌并加热升温至60℃，然后迅速加入3.33mmol Pd(PPh3)4和33.25mmol TBAB，滴加完毕后，继续升温至72℃回流反应24h，反应完毕，降温，用二氯甲烷萃取，有机相水洗至中性，干燥，过滤，浓缩。用乙酸乙酯和正庚烷混合溶剂重结晶后烘干得到目标产物H155。
MALDI-TOF：m/z计算值：C63H36N4O，864.29；m/z实测值：864.53。
化合物元素分析结果(％)：计算值C 87.48，H 4.19，N 6.48，O 1.85；测试值：C87.49，H 4.18，N 6.49，O 1.85。
以下列举几种本发明所述有机化合物应用于OLED器件中的应用例：
应用例1
一种OLED器件，其结构示意图如图2所示，依次层叠的基板160，阳极110(氧化铟锡ITO，15nm)，第一空穴传输层121(10nm)，第二空穴传输层122(95nm)，发光层130(30nm)，第一电子传输层141(35nm)，第二电子传输层142(5nm)，阴极150(镁银电极，镁银质量比为1:9，15nm)，盖帽层170(CPL，100nm)。
所述OLED器件的制备方法包括如下步骤：
(1)将玻璃基板切成50mm×50mm×0.7mm的大小，分别在异丙醇和去离子水中超声处理30min，然后暴露在臭氧下清洁10min；将通过磁控溅射所得的具有ITO阳极的玻璃基板安装到真空沉积设备上；
(2)在真空度为2×10-6Pa下，在ITO阳极上真空蒸镀化合物HAT-CN，厚度为10nm，作为第一空穴传输层；
(3)在第一空穴传输层上真空蒸镀化合物TAPC作为第二空穴传输层，厚度为95nm；
(4)在第二空穴传输层上真空蒸镀发光层，采用本发明提供的有机化合物H2和有机化合物H162作为主体材料(H2与H162的质量比为38:62)，Ir(piq)2(acac)作为掺杂材料，主体材料和Ir(piq)2(acac)的质量比为97:3，厚度为30nm；
(5)在发光层上真空蒸镀化合物BCP作为第一电子传输层，厚度为35nm；
(6)在第一电子传输层上真空蒸镀化合物Alq3作为第二电子传输层，厚度为5nm；
(7)在第二电子传输层上真空蒸镀镁银电极作为阴极，Mg和Ag质量比为1:9，厚度为15nm；
(8)在阴极上真空蒸镀高折射率的化合物CBP，厚度为100nm，作为盖帽层(阴极覆盖层，CPL)，得到所述OLED器件。
所述OLED器件中所使用的材料结构如下：
Figure BDA0003673332200000271
Figure BDA0003673332200000281
应用例2-7
一种OLED器件，其与应用例1的区别仅在于，将步骤(4)中的有机化合物H2分别替换为等量的化合物H22、H54、H66、H82、H94、H119；器件的结构、厚度、其它材料及制备方法均与应用例1相同。
应用例8
一种OLED器件，其与应用例1的区别仅在于，将步骤(4)中的主体材料(H2与H162的组合)用等量的有机化合物H155替换；器件的结构、厚度、其它材料及制备方法均与应用例1相同。
对比例1
一种OLED器件，其与应用例1的区别仅在于，将步骤(4)中的主体材料(H2与H162的组合)用等量的对比化合物HH
Figure BDA0003673332200000282
替换；器件的结构、厚度、其它材料及制备方法均与应用例1相同。
OLED器件的性能评价：
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流，然后用电流除以发光面积得到OLED器件在不同电压下的电流密度；用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度；根据OLED器件在不同电压下的电流密度和亮度，得到在相同电流密度下(10mA/cm2)的启亮电压和电流效率(CE，Cd/A)，Von为亮度1Cd/m2下的启亮电压；通过测量OLED器件的亮度达到初始亮度的95％时的时间而获得寿命LT95(在50mA/cm2测试条件下)。
以对比例1(REF)的启亮电压Von、电流效率CE和寿命LT95的测试数据为100％计，应用例1-8的Von、CE和LT95分别为各自的测试数据与对比例1的测试数据的比值，即为与对比例1相比的相对值；具体数据如表1所示。
表1
OLED器件 发光层主体材料 V<sub>on</sub> CE LT95
应用例1 H2/H162 95.5％ 107.2％ 105.4％
应用例2 H22/H162 95.9％ 106.9％ 106.6％
应用例3 H54/H162 96.1％ 106.6％ 107.5％
应用例4 H66/H162 95.1％ 105.9％ 106.4％
应用例5 H82/H162 95.8％ 106.3％ 106.8％
应用例6 H94/H162 95.3％ 105.7％ 107.1％
应用例7 H119/H162 96.0％ 106.2％ 106.5％
应用例8 H155 95.7％ 104.3％ 109.6％
对比例1(REF) 对比化合物HH 100％ 100％ 100％
从表1可以看出，相对于对比例1中的器件，使用本发明所述有机化合物的OLED器件具有较低的工作电压(启亮电压)、较高的发光效率以及较长的寿命。具体地，相对于对比例1，采用本发明所述有机化合物的OLED器件的工作电压得到降低，启亮电压降低了3.9-5％，电流效率提高了4.3-7.2％，LT95寿命延长了5.4-10％，发光效率和工作寿命得到明显改善。这可能得益于本发明的有机化合物具有较高的载流子传输速率和平衡的载流子传输性能，有助于器件中空穴和电子传输的平衡同时获得较宽的载流子复合区域，提高发光效率；同时有助于电子更加顺利地注入，降低器件电压，而且具有优良的成膜性和热稳定性，在蒸镀中形成良好的无定形薄膜，有利于保持器件的稳定性，延长工作寿命。
申请人声明，本发明通过上述实施例来说明本发明的有机化合物、有机电致发光器件及其应用，但本发明并不局限于上述工艺步骤，即不意味着本发明必须依赖上述工艺步骤才能实施。所属技术领域的技术人员应该明了，对本发明的任何改进，对本发明所选用原料的等效替换及辅助成分的添加、具体方式的选择等，均落在本发明的保护范围和公开范围之内。

Claims (15)

1.一种有机化合物，其特征在于，所述有机化合物具有如式I所示结构：
Figure FDA0003673332190000011
其中，L1、L2各自独立地选自单键、C6-C30亚芳基或C3-C30亚杂芳基中的任意一种；
R1、R2、R3各自独立地选自卤素、氰基、取代或未取代的C1-C30直链或支链烷基、取代或未取代的C3-C30环烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C6-C30芳胺基、取代或未取代的C6-C30芳基酮基、取代或未取代的C3-C30杂芳基酮基、取代或未取代的C6-C30芳基砜基、取代或未取代的C6-C30芳基硼基中的任意一种；
n1、n2各自独立地选自0-3的整数，n3选自0-2的整数；
n1、n2和n3不同时为0。
2.根据权利要求1所述的有机化合物，其特征在于，R1、R2、R3中所述取代的取代基各自独立地选自卤素、氰基、未取代或R'取代的C1-C10直链或支链烷基、未取代或R'取代的C3-C10环烷基、未取代或R'取代的C1-C10烷氧基、未取代或R'取代的C6-C20芳基、未取代或R'取代的C3-C20杂芳基、未取代或R'取代的C6-C20芳胺基中的至少一种；
R'选自卤素、氰基、C1-C10直链或支链烷基、C6-C20芳基、C3-C20杂芳基或C6-C20芳胺基中的至少一种。
3.根据权利要求1所述的有机化合物，其特征在于，所述有机化合物具有如式IA或式IB所示结构：
Figure FDA0003673332190000021
其中，L1、L2、R1、R2、R3、n1、n2具有与式I中相同的限定范围。
4.根据权利要求1或3所述的有机化合物，其特征在于，所述L1、L2各自独立地选自单键、亚苯基、亚联苯基、亚萘基、亚吡啶基或亚嘧啶基中的任意一种。
5.根据权利要求1或3所述的有机化合物，其特征在于，所述R1、R2、R3各自独立地选自卤素、氰基、未取代或卤代的C1-C10直链或支链烷基、未取代或卤代的C1-C10烷氧基、取代或未取代的C6-C20芳基、取代或未取代的C3-C20杂芳基、取代或未取代的C6-C20芳胺基、C6-C20芳基酮基、C6-C20芳基砜基中的任意一种；
R1、R2、R3中所述取代的取代基各自独立地选自卤素、氰基、未取代或卤代的C1-C10直链或支链烷基、C3-C10环烷基、未取代或卤代的C1-C10烷氧基、C6-C20芳基、C3-C20杂芳基或C6-C20芳胺基中的至少一种。
6.根据权利要求5所述的有机化合物，其特征在于，所述R1、R2、R3各自独立地选自卤素、氰基、未取代或卤代的C1-C6直链或支链烷基、未取代或卤代的C1-C6烷氧基、
Figure FDA0003673332190000031
Figure FDA0003673332190000032
Figure FDA0003673332190000041
其中，X1、X3各自独立地选自O、S、N-R13或CR13R14中的任意一种；
X2选自CR13R14、
Figure FDA0003673332190000042
中的任意一种；
R11、R12各自独立地选自卤素、氰基、未取代或卤代的C1-C10直链或支链烷基、C3-C10环烷基、未取代或卤代的C1-C10烷氧基、C6-C20芳基、C3-C20杂芳基或C6-C20芳胺基中的任意一种；
R13、R14各自独立地选自氢、卤素、氰基、未取代或卤代的C1-C10直链或支链烷基、C3-C10环烷基、未取代或卤代的C1-C10烷氧基、C6-C20芳基、C3-C20杂芳基或C6-C20芳胺基中的任意一种；
m1、m2各自独立地选自0-3的整数；
虚线代表基团的连接位点。
7.根据权利要求1或6所述的有机化合物，其特征在于，所述R1、R2、R3各自独立地选自卤素、氰基、未取代或卤代的C1-C6直链或支链烷基、未取代或卤代的C1-C6烷氧基、
Figure FDA0003673332190000043
Figure FDA0003673332190000044
Figure FDA0003673332190000051
Figure FDA0003673332190000061
其中，虚线代表基团的连接位点；
R21、R22各自独立地选自氰基、C6-C20芳基、C3-C20杂芳基、未取代或卤代的C1-C6直链或支链烷基中的任意一种；
R23、R24各自独立地选自氢、氰基、C6-C20芳基、C3-C20杂芳基、未取代或卤代的C1-C6直链或支链烷基中的任意一种。
8.根据权利要求1或3所述的有机化合物，其特征在于，所述n1、n2各自独立地为0或1。
9.根据权利要求1或3所述的有机化合物，其特征在于，所述有机化合物选自如下化合物H1-H162中的任意一种：
Figure FDA0003673332190000062
Figure FDA0003673332190000071
Figure FDA0003673332190000081
Figure FDA0003673332190000091
Figure FDA0003673332190000101
Figure FDA0003673332190000111
Figure FDA0003673332190000121
Figure FDA0003673332190000131
10.一种有机电致发光器件，其特征在于，所述有机电致发光器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机层，所述有机层包括至少一种如权利要求1-9任一项所述的有机化合物。
11.根据权利要求10所述的有机电致发光器件，其特征在于，所述有机层包括发光层，所述发光层包括至少一种如权利要求1-9任一项所述的有机化合物。
12.根据权利要求10所述的有机电致发光器件，其特征在于，所述有机层包括发光层以及设置于所述发光层与阳极之间的空穴传输区，所述空穴传输区包括至少一种如权利要求1-9任一项所述的有机化合物。
13.根据权利要求10所述的有机电致发光器件，其特征在于，所述有机层包括发光层以及设置于所述发光层与阴极之间的电子传输区，所述电子传输区包括至少一种如权利要求1-9任一项所述的有机化合物。
14.一种显示面板，其特征在于，所述显示面板包括如权利要求10-13任一项所述的有机电致发光器件。
15.一种显示装置，其特征在于，所述显示装置包括如权利要求14所述的显示面板。
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