CN114516803A - 一种稠环化合物及其应用 - Google Patents

一种稠环化合物及其应用 Download PDF

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CN114516803A
CN114516803A CN202011310370.7A CN202011310370A CN114516803A CN 114516803 A CN114516803 A CN 114516803A CN 202011310370 A CN202011310370 A CN 202011310370A CN 114516803 A CN114516803 A CN 114516803A
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陈志宽
蔡烨
魏定纬
丁欢达
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Ningbo Lumilan Advanced Materials Co Ltd
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Abstract

本发明提供一种稠环化合物及其应用,所述稠环化合物具有如下式I所示结构,本发明的稠环化合物用作空穴传输材料,能够提高有机发光元件的效率、延长寿命,降低驱动电压,利用本发明所述稠环化合物用作空穴传输材料的有机电致发光器件,具有较低的驱动电压,较高的电流效率以及延长了寿命。

Description

一种稠环化合物及其应用
技术领域
本发明属于有机电致发光材料领域,涉及一种稠环化合物及其应用。
背景技术
有机发光材料按功能大致可分为发光材料、空穴注入材料、空穴传输材料、电子传输材料、电子注入材料等。
目前为止,关于空穴传输材料,具有咔唑骨架的胺衍生物被大量研究,但是在驱动电压、效率和寿命方面还存在很多问题,因此,需要开发一种新型的空穴传输材料,提高有机发光元件的效率、延长寿命、降低驱动电压。
发明内容
针对现有技术的不足,本发明的目的在于提供一种稠环化合物及其应用。本发明的稠环化合物用作空穴传输材料,能够提高有机发光元件的效率、延长寿命,降低驱动电压。
为达到此发明目的,本发明采用以下技术方案:
一方面,本发明提供一种稠环化合物,所述稠环化合物具有如下式I所示结构:
Figure BDA0002789622490000011
其中
Figure BDA0002789622490000012
各自独立选自5-30元芳环或芳杂环,
R1、R2各自独立选自氢、氘、取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
R3-R6各自独立选自氢、氘、卤素、氰基、取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基、-L-NAr1Ar2、-L-SiR7R8R9、-LOR10、-LSR11
R7-R11各自独立选自氢、氘、取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
R3-R6至少有一者选自-L-NAr1Ar2,R3-R6各自独立存在或相邻两者成环,
各L相同或不同,选自单键、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
Ar1、Ar2各自独立选自取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
所述杂芳基中杂原子选自O、S、N中的至少一者,
a、b、c、d各自独立为0-3的整数;
如上所述基团具有取代基时,所述取代基独立地选自氘、卤素、硝基、氰基、R12取代或未取代的C1-C4的烷基、R12取代或未取代的C1-C4的烷氧基、R12取代或未取代的C6-C12的芳基、R12取代或未取代的C6-C12的芳氧基、R12取代或未取代的C6-C12的芳胺基、R12取代或未取代的C3-C12的杂芳基、R12取代或未取代的C3-C12的杂芳胺基;
R12选自氘、卤素、氰基、C1-C4的烷基、C6-C12的芳基,多个R12相同或不同。
本发明所述化合物具有式I所示的稠环结构,使得该化合物具有合适的空穴传输能力,进入发光层的电子和空穴能平衡,使得用其作为空穴传输材料的有机电致发光器件具有较高的效率,较低的驱动电压,并延长了其使用寿命。
优选地,所述
Figure BDA0002789622490000021
各自独立选自苯环、萘环、菲环、吡啶环、吲哚环、苯并呋喃环或苯并噻吩环,优选苯环、萘环或菲环。
优选地,所述稠环化合物为具有如下结构之一的化合物:
Figure BDA0002789622490000022
其中各基团的限定范围与式I所示化合物中的限定相同。
优选地,所述稠环化合物为具有如下式II所示结构的化合物:
Figure BDA0002789622490000031
其中X1、X2各自独立选自单键、O、S、NAr6、CAr7Ar8,且一者为单键,
Ar6取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
Ar7-Ar8各自独立选自取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基;
其余基团的限定与式I所示化合物中的限定相同。
优选地,所述Ar1、Ar2、Ar6、Ar7、Ar8各自独立选自取代或未取代的如下基团:吡啶、苯基、联苯基、联三苯基、萘基、联萘基、苯基萘基、芴基、苯基芴基、苯并芴基、二苯并芴基、菲基、苯基菲基、蒽基、茚基、亚三苯基、芘基、并四苯基、苝基、屈基、稠四苯基、荧蒽基、螺联二芴基、呋喃基、二苯并呋喃基、噻吩基、二苯并噻吩基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、吡啶基、咔唑基或二氢吖啶基;当为取代的所述基团时,取代基为卤素、氰基、C1-C4的烷基、C6-C12的芳基。
优选地,所述Ar1、Ar2、Ar6、Ar7、Ar8各自独立选自取代或未取代的如下基团:
Figure BDA0002789622490000041
R13选自甲基、乙基、丙基、丁基、异丙基、叔丁基、苯基、联苯基、三联苯基、萘基、蒽基、菲基,T选自NAr3、O、S、C Ar4Ar5
Ar3选自苯基、联苯基、三联苯基、萘基、蒽基或菲基;
Ar4-Ar5各自独立选自甲基、乙基、丙基、丁基、异丙基、叔丁基、苯基、联苯基、三联苯基、萘基、蒽基、菲基,Ar4-Ar5独立存在或两者连接成环。
当为取代的如上所述基团时,取代基为卤素、氰基、C1-C4的烷基、C6-C12的芳基。
优选地,所述稠环化合物为如下化合物W-1~W-156中的任意一种:
Figure BDA0002789622490000042
Figure BDA0002789622490000051
Figure BDA0002789622490000061
Figure BDA0002789622490000071
Figure BDA0002789622490000081
Figure BDA0002789622490000091
Figure BDA0002789622490000101
Figure BDA0002789622490000111
Figure BDA0002789622490000121
Figure BDA0002789622490000131
本发明所述的稠环化合物可以通过原料a和原料b,由以下合成路线合成:
Figure BDA0002789622490000132
本发明所述烷基可以为直链及支链中的任一种,可选的,所述直链烷基包括但不限于甲基、乙基、丙基、丁基,所述支链烷基包括但不限于异丙基、2-丁基、异丁基、叔丁基。
本发明所述环烷基包括但不限于环丙烷、环丁烷、环己烷。
本发明所述烯基是指衍生自具有一个或多个碳-碳双键并具有2至40个碳原子的直链或支链不饱和烃的单价取代基。其实例包括但不限于乙烯基、烯丙基、异丙烯基、2-丁烯基等。
本发明所述芳基包括单环、多环、稠环类芳基,所述环之间可以被短的非芳族单元(例如亚甲基)所间断。优选的,所述芳基选自苯基、联苯基、联三苯基、萘基、联萘基、苯基萘基、萘基苯基、芴基、苯基芴基、苯并芴基、二苯并芴基、菲基、苯基菲基、蒽基、茚基、亚三苯基、芘基、并四苯基、苝基、屈基、稠四苯基、荧蒽基或螺二芴基。
本发明所述杂芳基包括单环、多环、稠环类,所述环之间可以被短的非芳族单元(例如亚甲基、O、S、N)所间断。优选的,所述杂芳基选自呋喃基、苯硫基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋吖基、吡啶基、吡嗪基、嘧啶基、哒嗪基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喔啉基、咔唑基、吩噁嗪基、吩噻嗪基、菲啶基、苯并间二氧杂环戊烯基或二氢吖啶基。
另一方面,本发明提供一种空穴传输材料,所述空穴传输材料包括如上所述的稠环化合物中的任意一种或至少两种的组合。
另一方面,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第一电极、第二电极以及位于第一电极和第二电极之间的有机层,所述有机层包括如上所述的稠环化合物中的任意一种或至少两种的组合。
优选地,所述有机层包括空穴传输层和/或发光辅助层。
优选地,所述空穴传输层的材料包括如上所述的稠环化合物中的任意一种或至少两种的组合。
优选地,所述发光辅助层包括如上所述的稠环化合物中的任意一种或至少两种的组合。
另一方面,本发明提供一种有机电致发光产品,所述有机电致发光产品包括如上所述的有机电致发光器件。
相对于现有技术,本发明具有以下有益效果:
本发明的稠环化合物用作空穴传输材料,能够提高有机发光元件的效率、延长寿命,降低驱动电压,利用本发明所述稠环化合物用作空穴传输材料的有机电致发光器件具有较低的驱动电压,较高的电流效率以及延长了寿命。
附图说明
图1为本发明所述有机电致发光器件的结构示意图,其中1为基板,2为阳极、3为空穴注入层、4为空穴传输层、5为发光层、6为电子传输层、7为电子注入层,8为阴极。
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。
合成实施例
合成方法如下:
Figure BDA0002789622490000151
中间体1-W-1的合成:在100毫升三颈瓶中,氮气保护下加入原料1(3.38克,0.01mol),无水THF(25毫升),将反应液冷却至-78摄氏度。在搅拌条件下,加入正丁基锂(0.011mol),在此温度下反应1小时。将丙酮(0.58g,0.01mmol)溶于10ml无水四氢呋喃中,滴加至反应瓶中。室温条件下反应完成后,向反应体系加入水,经二氯甲烷萃取,所得到的萃取液依序加入硫酸镁干燥、过滤及旋干;粗产物以层析纯化(乙酸乙酯/正己烷,1/10),得中间体1-W-1(1.36克,产率43%)。
以类似方法制备以下化合物
Figure BDA0002789622490000152
Figure BDA0002789622490000153
中间体2-W-1的合成:在100毫升三颈瓶中,氮气保护下加入中间体1-W-1(3.16克,0.01mol),无水THF(35毫升),将反应液冷却至-78摄氏度。在搅拌条件下,加入正丁基锂(0.011mol),在此温度下反应1小时。将原料2(2.58g,0.01mmol)溶于20ml无水四氢呋喃中,滴加至反应瓶中。室温条件下反应完成后,向反应体系加入水,经二氯甲烷萃取,所得到的萃取液依序加入硫酸镁干燥、过滤及旋干;粗产物以层析纯化(乙酸乙酯/正己烷,1/10),得中间体2-W-1(1.36克,产率36%)。
以类似方法制备以下化合物
Figure BDA0002789622490000161
Figure BDA0002789622490000171
Figure BDA0002789622490000172
中间体3-W-1的合成:在100毫升三颈瓶中,加入中间体2-W-1(4.96克,0.01mol),加入醋酸(30毫升),盐酸(2毫升),回流下搅拌4小时,反应结束后,用饱和的碳酸氢钠水溶液洗涤,有机层用无水硫酸镁干燥,除去有机溶剂,粗产物用四氢呋喃:乙醇=1:4重结晶,得到中间体3-W-1的合成(1.93克,产率42%)。
以类似方法制备以下化合物
Figure BDA0002789622490000181
Figure BDA0002789622490000191
Figure BDA0002789622490000192
W-1的合成:在100毫升三颈瓶中,氮气保护下加入中间体3-W-1(0.01mol),二苯胺(0.01mol),二氧六环(30毫升),醋酸钯(5mmol),三叔丁基磷(8mmol),碳酸铯(0.02mol),100摄氏度下反应过夜,反应完成后,加水猝灭,二氯甲烷萃取,有机层用无水硫酸镁干燥,除去有机溶剂,粗产物用层析纯化(乙酸乙酯/正己烷,1/10),得W-1(4.45克,产率81%)。
元素分析:C42H31N,理论值:C 91.77,H 5.68,N 2.55,实测值:C 91.75,H 5.70,N2.55;
HRMS(ESI)m/z(M+):理论值:549.2457,实测值:549.2464。
以类似方法制备以下化合物
Figure BDA0002789622490000201
Figure BDA0002789622490000211
Figure BDA0002789622490000221
W-60的合成:取100毫升三颈瓶,并放入搅拌子与上接回流管,充入氮气,加入中间体3-W-60(4.60克,0.01mol),原料4(4.54克,0.01mol),碳酸钾(0.015mol),四(三苯基膦)钯(0.5mmol),甲苯(40毫升),水(10毫升),氮气保护下,60℃反应12小时,反应完成后冷却至室温,加入3毫升冰水淬灭,二氯甲烷(3×30毫升)萃取,所得到的萃取液依序加入硫酸镁干燥、过滤及旋干,粗产物以层析纯化(乙酸乙酯/正己烷,1/10(体积比)),得W-60(6.48克,产率82%)。
以类似方法制备以下化合物
Figure BDA0002789622490000222
测试:本发明中的中间体和化合物的分析检测使用质谱仪(型号型号OrbitrapID-X Tribrid)和有机元素分析仪(型号PE2400Ⅱ)。
Figure BDA0002789622490000223
Figure BDA0002789622490000231
器件实施例
本实施例提供一种有机电致发光器件,如图1所示,包括依次层叠设置在基板1上的阳极2、空穴注入层3、空穴传输层4、发光层5、电子传输层6、电子注入层7和阴极8。
其中,阳极2选用ITO材料;
空穴注入层3材料由下述所示结构的化合物PD与化合物NPB掺杂形成:其中PD与NPB掺杂的质量比为3:97;
Figure BDA0002789622490000241
空穴传输层4材料选用合成实施例制备的化合物或者对比例的化合物(如表3中所示):
发光层5以主体材料和客体材料共掺杂形成,其中主体材料选用CBP,客体材料选用化合物Ir(piq)2(acac),主体材料和客体材料掺杂的质量比为95:5;其中化合物CBP、Ir(piq)2(acac)的化学结构如下所示:
Figure BDA0002789622490000242
电子传输层6材料由下述所示结构的化合物BPhen与化合物LiQ掺杂形成:其中BPhen与LiQ掺杂的质量比为1:1;
Figure BDA0002789622490000243
电子注入层7材料选用如下所述结构的化合物LiQ:
Figure BDA0002789622490000244
阴极8材料选用金属Mg和Ag的混合材料,其中,金属Mg和Ag的质量比为9:1。
上述有机电致发光器件的制备包括如下步骤:
1)基板清理:
将涂布了ITO透明电极的玻璃基板1在水性清洗剂(所述水性清洗剂的成分及浓度:乙二醇类溶剂≤10wt%,三乙醇胺≤1wt%)中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂(体积比1:1)中超声除油,在洁净环境下烘烤至完全除去水份,然后用紫外光和臭氧清洗;
2)蒸镀:
把上述带有阳极2的玻璃基板1置于真空腔内,抽真空至1×10-6至2×10-4Pa,在上述阳极层膜上以共蒸的方式真空蒸镀空穴注入层3材料,其中PD与NPB按质量比调整速率,蒸镀总速率为0.1nm/s,蒸镀厚度为10nm;
3)在空穴注入层3之上蒸镀空穴传输层4,蒸镀速率为0.1nm/s,蒸镀膜厚为80nm;
4)在空穴传输层4之上蒸镀发光层5,以共蒸的方式真空蒸镀发光主体材料和客体材料,主体材料与客体材料按质量比调整蒸镀速率,蒸镀总速率为0.1nm/s,蒸镀总膜厚为40nm;
5)在发光层5之上真空蒸镀一层电子传输层6,按化合物BPhen与LiQ的质量比调整蒸镀速率,其蒸镀总速率为0.1nm/s,蒸镀总膜厚为30nm;
6)在电子传输层6上真空蒸镀一层电子注入层7,其蒸镀速率为0.05nm/s,蒸镀总膜厚为1nm;
7)在电子注入层7上蒸镀阴极8,按金属Mg和Ag的质量比调整蒸镀速率,蒸镀总速率为0.1nm/s,蒸镀总膜厚为80nm。
对比例1-4中使用的化合物如下:
Figure BDA0002789622490000251
Figure BDA0002789622490000261
测试例1
1、测定化合物热分解温度
化合物热分解温度的测定:使用热重分析仪(美国TA TGA55)对本发明含氮杂环化合物进行热分解温度(Td)测试,测试范围室温至600℃,升温速率10℃/min,氮气氛围下,重量损失5%的温度定义为分解温度,测试结果如表1所示。
表1含氮杂环化合物热分解温度
化合物 T<sub>d</sub>(℃)
W-1 307
W-69 371
W-60 440
W-67 439
W-82 453
W-101 361
W-112 418
W-129 367
W-137 415
W-144 387
2、LUMO和HOMO能级测试
使用电化学工作站利用循环伏安法(CV上海辰华CHI-600E)对实施例1-13制备的含氮杂环化合物的LUMO和HOMO能级进行测试,以铂丝(Pt)为对电极,银/氯化银(Ag/AgCl)为参比电极,在氮气氛围下,在含有0.1M四丁基六氟磷酸铵的二氯甲烷电解液中以100mV/s的扫描速率进行测试,以二茂铁进行电位标定,设定二茂铁的电位在真空状态下的绝对能级为-4.8eV:
HOMO能阶=-e(Eox-E1/2,ferrocene)+(-4.8)eV
LUMO能阶=-e(Ere-E1/2,ferrocene)+(-4.8)eV;
其中Eox为氧化电位,Ere为还原电位,E1/2,ferrocene为二茂铁电位。
三线态能级测试条件:以甲苯作为溶剂,将待测试化合物配制成溶液(浓度2*10- 5mol/L),使用荧光分光光度计(日立F-4600)对上述溶液在-78℃条件下进行测试。其中ET1(eV)表示化合物的三线态能级,其用如下公式进行计算,
ET1=1240/最短吸收波长。
测试结果如表2所示。
表2含氮杂环化合物的能级测试结果
Figure BDA0002789622490000271
测试例2
仪器:器件的电流、电压、亮度、发光光谱等特性采用PR 650光谱扫描亮度计和Keithley K 2400数字源表系统同步测试;
测试条件:电流密度为20mA/cm2,室温。
寿命测试:器件亮度下降至原始亮度的98%时记录时间(以小时计)。
对器件实施例1-9和对比例1-2中的所提供的有机电致发光器件进行测试,结果如表3所示:
表3器件性能测试结果
器件实施例 空穴传输材料 发光辅助层 电压(V) 电流效率cd/A 寿命(h)
器件实施例1 W-1 / 4.1 19 57
器件实施例2 W-1 W-69 4.0 21 89
器件实施例3 W-60 / 4.0 20 67
器件实施例4 W-67 / 3.9 23 65
器件实施例5 W-82 / 4.0 21 72
器件实施例6 W-101 / 4.0 22 64
器件实施例7 W-112 / 4.0 20 82
器件实施例8 W-129 / 3.9 24 91
器件实施例9 W-137 / 4.0 26 76
器件实施例10 W-144 / 4.0 22 75
器件对比例1 Ref-1 / 4.2 16 28
器件对比例2 Ref-2 / 4.2 17 25
器件对比例3 Ref-3 / 4.3 16 17
器件对比例4 Ref-4 / 4.4 14 21
由表3可以看出,
Figure BDA0002789622490000281
结构的刚性过强,平面性过好,导致载流子向水平方向移动,而减少向垂直方向的移动,导致进入发光层的载流子数量减少,器件的效率降低,驱动电压升高,寿命缩短;
Figure BDA0002789622490000282
的空穴传输能力较弱,导致空穴与电子的传输不平衡,器件的效率降低,驱动电压升高,寿命缩短。
申请人声明,本发明通过上述实施例来说明本发明的稠环化合物及其应用,但本发明并不局限于上述实施例,即不意味着本发明必须依赖上述实施例才能实施。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 (10)

1.一种稠环化合物,其特征在于,所述稠环化合物具有如下式I所示结构:
Figure FDA0002789622480000011
其中
Figure FDA0002789622480000012
各自独立选自5-30元芳环或芳杂环,
R1、R2各自独立选自氢、氘、取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
R3-R6各自独立选自氢、氘、卤素、氰基、取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基、-L-NAr1Ar2、-L-SiR7R8R9、-LOR10、-LSR11
R7-R11各自独立选自氢、氘、取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
R3-R6至少有一者选自-L-NAr1Ar2,R3-R6各自独立存在或相邻两者成环,
各L相同或不同,选自单键、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
Ar1、Ar2各自独立选自取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
所述杂芳基中杂原子选自O、S、N中的至少一者,
a、b、c、d各自独立为0-3的整数,
如上所述基团具有取代基时,所述取代基独立地选自氘、卤素、硝基、氰基、R12取代或未取代的C1-C4的烷基、R12取代或未取代的C1-C4的烷氧基、R12取代或未取代的C6-C12的芳基、R12取代或未取代的C6-C12的芳氧基、R12取代或未取代的C6-C12的芳胺基、R12取代或未取代的C3-C12的杂芳基、R12取代或未取代的C3-C12的杂芳胺基;
R12选自氘、卤素、氰基、C1-C4的烷基、C6-C12的芳基,多个R12相同或不同。
2.根据权利要求1所述的稠环化合物,其特征在于,所述
Figure FDA0002789622480000021
各自独立选自苯环、萘环、菲环、吡啶环、吲哚环、苯并呋喃环或苯并噻吩环,优选苯环、萘环或菲环。
3.根据权利要求1或2所述的稠环化合物,其特征在于,所述稠环化合物为具有如下结构之一的化合物:
Figure FDA0002789622480000022
其中各基团的限定范围与式I所示化合物中的限定相同。
4.根据权利要求1-3中任一项所述的稠环化合物,其特征在于,所述稠环化合物为具有如下式II所示结构的化合物:
Figure FDA0002789622480000023
其中X1、X2各自独立选自单键、O、S、NAr6、CAr7Ar8,且一者为单键,
Ar6取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,
Ar7-Ar8各自独立选自取代或未取代C1-C10的直链烷基、取代或未取代C3-C10的支链烷基、取代或未取代C3-C10的环烷基、取代或未取代C2-C10的烯基、取代或未取代C2-C10的炔基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基;
其余基团的限定与式I所示化合物中的限定相同。
5.根据权利要求1-4中任一项所述的稠环化合物,其特征在于,所述Ar1、Ar2、Ar6、Ar7、Ar8各自独立选自取代或未取代的如下基团:吡啶基、苯基、联苯基、联三苯基、萘基、联萘基、苯基萘基、芴基、苯基芴基、苯并芴基、二苯并芴基、菲基、苯基菲基、蒽基、茚基、亚三苯基、芘基、并四苯基、苝基、屈基、稠四苯基、荧蒽基、螺联二芴基、呋喃基、二苯并呋喃基、噻吩基、二苯并噻吩基、苯并呋喃基、苯并噻吩基、异苯并呋喃基、吡啶基、咔唑基或二氢吖啶基;当为取代的所述基团时,取代基为卤素、氰基、C1-C4的烷基、C6-C12的芳基。
6.根据权利要求1-5中任一项所述的稠环化合物,其特征在于,所述Ar1、Ar2、Ar6、Ar7、Ar8各自独立选自取代或未取代的如下基团:
Figure FDA0002789622480000031
R13选自甲基、乙基、丙基、丁基、异丙基、叔丁基、苯基、联苯基、三联苯基、萘基、蒽基、菲基,T选自NAr3、O、S、CAr4Ar5
Ar3选自苯基、联苯基、三联苯基、萘基、蒽基或菲基;
Ar4-Ar5各自独立选自甲基、乙基、丙基、丁基、异丙基、叔丁基、苯基、联苯基、三联苯基、萘基、蒽基、菲基,Ar4-Ar5独立存在或两者连接成环;
当为取代的如上所述基团时,取代基为卤素、氰基、C1-C4的烷基、C6-C12的芳基。
7.根据权利要求1-6中任一项所述的稠环化合物,其特征在于,所述稠环化合物为如下化合物W-1~W-156中的任意一种:
Figure FDA0002789622480000032
Figure FDA0002789622480000041
Figure FDA0002789622480000051
Figure FDA0002789622480000061
Figure FDA0002789622480000071
Figure FDA0002789622480000081
Figure FDA0002789622480000091
Figure FDA0002789622480000101
Figure FDA0002789622480000111
Figure FDA0002789622480000121
8.一种空穴传输材料,其特征在于,所述空穴传输材料包括如权利要求1-7中任一项所述的稠环化合物中的任意一种或至少两种的组合。
9.一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第一电极、第二电极以及位于第一电极和第二电极之间的有机层,所述有机层包括如权利要求1-7中任一项所述的稠环化合物中的任意一种或至少两种的组合;
优选地,所述有机层包括空穴传输层和/或发光辅助层;
优选地,所述空穴传输层的材料包括如上所述的稠环化合物中的任意一种或至少两种的组合;
优选地,所述发光辅助层包括如上所述的稠环化合物中的任意一种或至少两种的组合。
10.一种有机电致发光产品,其特征在于,所述有机电致发光产品包括如权利要求9所述的有机电致发光器件。
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