CN107805249A - 一种菲并咪唑衍生物及其有机发光器件 - Google Patents
一种菲并咪唑衍生物及其有机发光器件 Download PDFInfo
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Abstract
本发明提供一种菲并咪唑衍生物及其有机发光器件,属于有机发光材料技术领域。该菲并咪唑衍生物通过引入稠环类刚性、密集结构,使本发明所得到的一种菲并咪唑衍生物热稳定性能高、成膜性好,可用于制备有机发光器件,尤其是作为有机发光器件中的空穴传输材料,表现出高效率、长寿命优点,优于现有常用OLED器件。在OLED发光器件中具有良好的应用效果,具有良好的产业化前景。
Description
技术领域
本发明涉及有机光电材料技术领域,具体涉及一种菲并咪唑衍生物及其有机发光器件。
背景技术
有机电致发光二极管(Organic Light-Emitting Diode,OLED)是指有机发光材料在电流或电场的作用下发光的二极管,它能够将电能直接转化为光能。有机发光器件(OLED)作为一种新兴的平面面板显示,其具有自发光、视角宽、全固化、全彩化、反应速度快、高亮度、低驱动电压、厚度薄、质量轻、可制作大尺寸与弯曲面板等特点,近年来,OLED在显示器市场上得到了越来越多的应用,成为目前最具潜力的面板显示技术。
应用于OLED器件的OLED光电功能材料从用途上可划分为两大类,即电荷注入传输材料和发光材料,进一步,还可将电荷注入传输材料分为电子注入传输材料和空穴注入传输材料,还可以将发光材料分为主体发光材料和掺杂材料。为了制作高性能的OLED发光器件,要求各种有机功能材料具备良好的光电特性,空穴传输材料是有机半导体的重要组成部分,一般来说,空穴传输材料应满足以下几个条件:(1)良好的成膜性和热稳定性;(2)相对较小的电子亲和能,有利于阻挡电子注入;(3)相对较低的电离能,有利于空穴注入;(4)较好的电化学稳定性;(5)高的空穴迁移率,利于空穴传输;(6)具有和发光层相匹配的能级结构。
目前,有机发光器件已经向着实用化、商品化发展,但在器件的效率和寿命上仍需要进一步的提高,这对有机材料也提出了更高的要求。如何设计新的性能更好的材料进行调节,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菲并咪唑衍生物及其有机发光器件,本发明提供的一种菲并咪唑衍生物热稳定性能高、成膜性好,由该衍生物制成的有机发光器件,表现出高效率、长寿命的优点,是性能优良的有机发光材料。
本发明首先提供一种菲并咪唑衍生物,结构式为:
其中,Ar1、Ar2、L独立的选自C6~C60的取代或未取代的芳基、C10~C60的取代或未取代的稠环芳基、C3~C60的取代或未取代的杂芳基、C9~C60的取代或未取代的稠环杂芳基中的一种。
优选的,Ar1、Ar2独立的选自C6~C25的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基、C3~C18的取代或未取代的杂芳基、C9~C20的取代或未取代的稠环杂芳基中的一种;L选自C6~C20的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基、C9~C20的取代或未取代的稠环杂芳基中的一种。
优选的,Ar1、Ar2独立的选自苯基、萘基、菲基、蒽基、芘基、苝基、联苯基、三联苯基、茚基、吲哚基、吡啶基、嘧啶基、三嗪基、呋喃基、噻吩基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基、吩恶嗪基、吩噻嗪基、吖啶基、咔唑基、芴基或螺二芴基。
优选的,L选自如下结构:
其中,R1、R2、R3独立的选自C1~C10的烷基、C6~C20的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基中的一种。
优选的,一种菲并咪唑衍生物选自如下所示结构中的任意一种:
本发明还提供一种菲并咪唑衍生物在有机发光器件中的应用。
优选的,有机发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机化合物层,有机化合物层含有一种菲并咪唑衍生物。
优选的,有机化合物层包括空穴注入层、空穴传输层,电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层;所述有机化合物层中至少一层含有一种菲并咪唑衍生物。
优选的,空穴传输层中含有一种菲并咪唑衍生物。
本发明的有益效果:
本发明首先提供一种菲并咪唑衍生物,该菲并咪唑衍生物具有式(I)所示结构,通过引入稠环类刚性、密集结构,使本发明所得到的菲并咪唑衍生物热稳定性能高、成膜性好,可用于制备有机发光器件,尤其是作为有机发光器件中的空穴传输材料,表现出高效率、长寿命优点,优于现有常用OLED器件。本发明所述的菲并咪唑衍生物在OLED发光器件中具有良好的应用效果,具有良好的产业化前景。
具体实施方式
为了进一步理解本发明,下面结合实施例对本发明优选实施方案进行描述,但是应当理解,这些描述只是为进一步说明本发明的特征和优点,而不是对本发明权利要求的限制。
本发明所述烷基是指烷烃分子中少掉一个氢原子而成的烃基,其可以为直链烷基、支链烷基、环烷基,实例可包括甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、环戊基、环己基等,但不限于此。
本发明所述芳基是指苯基分子的芳核碳上去掉一个氢原子后,剩下一价基团的总称,实例可包括苯基、4-甲基苯基、4-叔丁基苯基、2-乙基苯基、联苯基或三联苯基等,但不限于此。
本发明所述稠环芳基是指芳烃分子的芳核碳上去掉一个氢原子后,剩下一价基团的总称,实例可包括1-萘基、2-萘基、蒽基、菲基、芘基或苝基等,但不限于此。
本发明所述杂芳基是指苯基分子中的一个或多个芳核碳被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫或氮原子,实例可包括吡啶基、嘧啶基、吡咯基、噻吩基、呋喃基、惡唑基或三嗪基等,但不限于此。
本发明所述稠环杂芳基是指芳烃分子中的一个或多个芳核碳被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫或氮原子,实例可包括吲哚基、喹啉基、异喹啉基、苯并噻吩基、苯并呋喃基、二苯并呋喃基、二苯并噻吩基或咔唑基等,但不限于此。
本发明首先提供一种菲并咪唑衍生物,结构式为:
其中,Ar1、Ar2、L独立的选自C6~C60的取代或未取代的芳基、C10~C60的取代或未取代的稠环芳基、C3~C60的取代或未取代的杂芳基、C9~C60的取代或未取代的稠环杂芳基中的一种。
优选的,Ar1、Ar2独立的选自C6~C25的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基、C3~C18的取代或未取代的杂芳基、C9~C20的取代或未取代的稠环杂芳基中的一种;L选自C6~C20的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基、C9~C20的取代或未取代的稠环杂芳基中的一种。
按照本发明,所述的取代的芳基、取代的五元杂环、取代的六元杂环、取代的稠杂环中,取代基独立的选自烷基、烷氧基、氨基、卤素、氰基、硝基、羟基或巯基。
优选的,Ar1、Ar2独立的选自苯基、萘基、菲基、蒽基、芘基、苝基、联苯基、三联苯基、茚基、吲哚基、吡啶基、嘧啶基、三嗪基、呋喃基、噻吩基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基、吩恶嗪基、吩噻嗪基、吖啶基、咔唑基、芴基或螺二芴基。
最优选L选自如下结构:
其中,R1、R2、R3独立的选自C1~C10的烷基、C6~C20的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基中的一种。
具体的,一种菲并咪唑衍生物,选自如下所示结构中的任意一种:
本发明的一种菲并咪唑衍生物,其制备方法如下:
其中,Ar1、Ar2、L独立的选自C6~C60的取代或未取代的芳基、C10~C60的取代或未取代的稠环芳基、C3~C60的取代或未取代的杂芳基、C9~C60的取代或未取代的稠环杂芳基中的一种。
按照本发明,结构式(I)所示的化合物按照如下所示方法制备得到:
在氮气保护下,醋酸钯与三叔丁基膦为催化剂,叔丁醇钠为碱的情况下,将仲胺与二溴代物反应得到中间体B。
将物质a加入到圆底烧瓶中,再加入甲苯使其溶解,向溶液中加入对甲苯磺酰肼,在一定温度条件下反应后,继续向反应液中依次加入中间体B和K2CO3,回流后,将反应液冷却至室温,用去离子水洗涤,有机相经干燥、浓缩、柱层析,得到目标产物(I)。
本发明对所述反应没有特殊的限制,采用本领域技术人员所熟知的偶联反应即可,该制备方法简单,原料易得。
本发明还提供一种菲并咪唑衍生物在有机发光器件中的应用,本发明所述的一种菲并咪唑衍生物可以作为空穴传输层材料在有机发光器件方面得到应用,所述有机发光器件包括阳极、阴极和有机物层,有机物层包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层;所述有机物层中至少一层含有上述所述的一种菲并咪唑衍生物。本发明的有机发光器件是在平面面板显示、平面发光体、照明用面发光OLED发光体、柔性发光体、复印机、打印机、LCD背光灯或计量机类的光源、显示板、标识等使用。
本发明对以下实施例中所采用的原料没有特别的限制,可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
实施例1:化合物1的合成
(1)向圆底烧瓶中依次加入化合物I-1(21.85g,73.8mmol)、化合物II-1(20.88g,73.8mmol)、t-BuONa(10.7g,111mmol)、Pd(OAc)2(0.33g,1.47mmol)以及超声除氧的甲苯(1.5L),在氮气保护下回流过液,待反应液冷却后用乙酸乙酯和水处理,并将得到的有机层用MgSO4干燥,减压蒸去溶剂,得到化合物III-1的粗品,以硅胶为固定相,二氯甲烷/己烷为洗脱剂,将粗品进行柱层析,得到化合物III-1(40.58g,78%)。
(2)将化合物III-1(35.25g,50mmol)加入到圆底烧瓶中,再加入适量的无水THF使其溶解,在-78℃的温度下,向反应瓶中滴加n-BuLi(4.9ml,60mmol),反应0.5h后,向反应液中快速滴加硼酸三甲脂(11.41g,75mmol),将温度缓慢升至室温,继续反应30min,反应完毕后,将反应液倒入稀盐酸水溶液中,有固体物质析出过滤,粗品过硅胶柱得到化合物IV-1(11.41g,75%)。
(3)将化合物V-1(12.64g,30mmol)加入到圆底烧瓶中,再加入甲苯使其溶解,向溶液中加入对甲苯磺酰肼(8.4g,45mmol),在80℃的条件下反应2h后,向反应液中依次加入化合物IV-1(13.69g,45mmol)和K2CO3(12.4g,90mmol),回流反应5h,将反应液冷却至室温,用去离子水洗涤反应液,有机相经干燥、浓缩、柱层析,得到化合物(12.05g,67%)。
质谱m/z:599.25(计算值:599.24)。理论元素含量(%)C44H29N3:C,88.12;H,4.87;N,7.01实测元素含量(%):C,88.13;H,4.86;N,7.01。上述结果证实获得产物为目标产品。
实施例2:化合物5的合成
按照化合物1的合成方法得到化合物5(12.77g,63%)。
质谱m/z:675.28(计算值:675.27)。理论元素含量(%)C50H33N3:C,88.86;H,4.92;N,6.22实测元素含量(%):C,88.87;H,4.91;N,6.22。上述结果证实获得产物为目标产品。
实施例3:化合物8的合成
按照化合物1的合成方法得到化合物8(13.65g,65%)。
质谱m/z:699.28(计算值:699.27)。理论元素含量(%)C52H33N3:C,89.24;H,4.75;N,6.00实测元素含量(%):C,89.25;H,4.74;N,6.00。上述结果证实获得产物为目标产品。
实施例4:化合物9的合成
按照化合物1的合成方法得到化合物9(12.50g,64%)。
质谱m/z:650.26(计算值:650.25)。理论元素含量(%)C47H30N4:C,86.74;H,4.65;N,8.61实测元素含量(%):C,86.74;H,4.64;N,8.62。上述结果证实获得产物为目标产品。
实施例5:化合物13的合成
按照化合物1的合成方法得到化合物13(11.89g,66%)。
质谱m/z:600.24(计算值:600.23)。理论元素含量(%)C43H28N4:C,85.97;H,4.70;N,9.33实测元素含量(%):C,85.97;H,4.71;N,9.32。上述结果证实获得产物为目标产品。
实施例6:化合物31的合成
按照化合物1的合成方法得到化合物31(13.87g,67%)。
质谱m/z:689.26(计算值:689.25)。理论元素含量(%)C50H31N3O:C,87.06;H,4.53;N,6.09;O,2.32实测元素含量(%):C,87.07;H,4.52;N,6.08;O,2.33。上述结果证实获得产物为目标产品。
实施例7:化合物89的合成
按照化合物1的合成方法得到化合物89(12.77g,63%)。
质谱m/z:675.28(计算值:675.27)。理论元素含量(%)C50H33N3:C,88.86;H,4.92;N,6.22实测元素含量(%):C,88.87;H,4.91;N,6.22。上述结果证实获得产物为目标产品。
实施例8:化合物114的合成
按照化合物1的合成方法得到化合物114(14.15g,67%)。
质谱m/z:703.31(计算值:703.30)。理论元素含量(%)C52H37N3:C,88.73;H,5.30;N,5.97实测元素含量(%):C,88.74;H,5.30;N,5.96。上述结果证实获得产物为目标产品。
实施例9:化合物115的合成
按照化合物1的合成方法得到化合物115(15.61g,69%)。
质谱m/z:753.32(计算值:753.31)。理论元素含量(%)C56H39N3:C,89.21;H,5.21;N,5.57实测元素含量(%):C,89.22;H,5.20;N,5.57。上述结果证实获得产物为目标产品。
对比应用实施例1
将ITO玻璃基板放在蒸馏水中清洗2次,超声波洗涤15分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥,转移到等离子体清洗机里,将上述基板洗涤5分钟,送到蒸镀机里。
在已经准备好的ITO透明电极上逐层蒸镀空穴注入层2-TNATA/50nm、蒸镀空穴传输层NPB或本发明实施例物质/30nm、蒸镀主体3Ph-Anthracene:掺杂Ir(tpy)310%混合/30nm、然后蒸镀电子传输层TPBi/30nm、阴极LiF/0.5nm、Al/200nm。
[应用实施例1-9]
将对比应用实施例1中的NPB换成应用实施例1-9中的所示化合物1、5、8、9、13、31、89、114、115。
表1为本发明实施例制备的化合物以及比较物质制备的发光器件的发光特性测试结果。
[表1]发光器件的发光特性测试
以上结果表明,本发明的一种菲并咪唑衍生物应用于有机发光器件中,尤其是作为空穴传输层材料,表现出高发光效率、长寿命的优点,是性能良好的有机发光材料。
显然,以上实施例的说明只是用于帮助理解本发明的方法及其核心思想。应当指出,对于所述技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以对本发明进行若干改进和修饰,这些改进和修饰也落入本发明权利要求的保护范围内。
Claims (8)
1.一种菲并咪唑衍生物,其特征在于,结构通式如式(I)所示:
其中,Ar1、Ar2、L独立的选自C6~C60的取代或未取代的芳基、C10~C60的取代或未取代的稠环芳基、C3~C60的取代或未取代的杂芳基、C9~C60的取代或未取代的稠环杂芳基中的一种。
2.根据权利要求1所述的一种菲并咪唑衍生物,其特征在于,Ar1、Ar2独立的选自C6~C25的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基、C3~C18的取代或未取代的杂芳基、C9~C20的取代或未取代的稠环杂芳基中的一种;L选自C6~C20的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基、C9~C20的取代或未取代的稠环杂芳基中的一种。
3.根据权利要求1所述的一种菲并咪唑衍生物,其特征在于,Ar1、Ar2独立的选自苯基、萘基、菲基、蒽基、芘基、苝基、联苯基、三联苯基、茚基、吲哚基、吡啶基、嘧啶基、三嗪基、呋喃基、噻吩基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基、吩恶嗪基、吩噻嗪基、吖啶基、咔唑基、芴基或螺二芴基。
4.根据权利要求1所述的一种菲并咪唑衍生物,其特征在于,L选自如下结构:
其中,R1、R2、R3独立的选自C1~C10的烷基、C6~C20的取代或未取代的芳基、C10~C20的取代或未取代的稠环芳基中的一种。
5.根据权利要求1所述的一种菲并咪唑衍生物,其特征在于,所述的菲并咪唑选自如下所示结构中的任意一种:
6.一种有机发光器件,其特征在于,所述有机发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机化合物层,所述的有机化合物层含有权利要求1-5任一项所述的一种菲并咪唑衍生物。
7.根据权利要求6中所述的一种有机发光器件,其特征在于,所述有机化合物层包括空穴注入层、空穴传输层,电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层;所述有机化合物层中至少一层含有权利要求1-5任一项所述的一种菲并咪唑衍生物。
8.根据权利要求7中所述的一种有机发光器件,其特征在于,空穴传输层中含有权利要求1-5中所述的一种菲并咪唑衍生物。
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CN109384786A (zh) * | 2018-11-12 | 2019-02-26 | 浙江工业大学 | 基于咪唑的同分异构体发光分子及其制备方法与应用 |
WO2021203663A1 (zh) * | 2020-04-10 | 2021-10-14 | 华南理工大学 | 一类基于菲并咪唑单元的电致发光聚合物及其制备方法与应用 |
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CN109384786A (zh) * | 2018-11-12 | 2019-02-26 | 浙江工业大学 | 基于咪唑的同分异构体发光分子及其制备方法与应用 |
WO2021203663A1 (zh) * | 2020-04-10 | 2021-10-14 | 华南理工大学 | 一类基于菲并咪唑单元的电致发光聚合物及其制备方法与应用 |
WO2022105626A1 (zh) * | 2020-11-18 | 2022-05-27 | Tcl科技集团股份有限公司 | 量子点发光二极管、显示装置和发光光源 |
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