CN110872310A - 稠环芳基化合物、有机电子器件及其应用 - Google Patents
稠环芳基化合物、有机电子器件及其应用 Download PDFInfo
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- CN110872310A CN110872310A CN201911119983.XA CN201911119983A CN110872310A CN 110872310 A CN110872310 A CN 110872310A CN 201911119983 A CN201911119983 A CN 201911119983A CN 110872310 A CN110872310 A CN 110872310A
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- aryl
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Abstract
Description
技术领域
本发明涉及光电材料技术领域,具体涉及一种稠环芳基化合物、有机电子器件及其应用。
背景技术
有机电致发光器件(organic light-emitting diodes,OLED)与无机电致发光器件(electro luminescence device,ELD)相比,具有亮度高、响应快、视角宽、工艺简单、颜色纯度高、可实现由蓝光到红光区的全彩色显示、可柔性等优点,在显示和照明领域具有广泛的应用前景,越来越受到人们的重视。
现有技术中的OLED器件通常包含空穴注入层、空穴传输层、发光层、电子传输层、电子注入层,并搭配合适的电极,以上各层分别由以下材料构成:空穴注入材料、空穴传输材料、发光材料、电子传输材料、电子注入材料。OLED器件在通电的情况下,空穴从阳极进入器件后穿过空穴注入层和空穴传输层,电子从阴极进入器件后穿过电子注入层和电子传输层,当空穴与电子在发光层结合时,激发发光材料而发光。因此,对于OLED器件来说,电荷的注入和传输是将电能转化为光的第一步,这一过程对器件的开启电压、发光效率及寿命都起到至关重要的作用。提高载流子的浓度和迁移率可以有效的提升电荷的注入和传输效率,进而降低器件的开启电压,提高发光效率及寿命。在空穴传输层方面,通过在空穴传输材料中掺入空穴性质的小分子,即空穴注入层材料(P掺杂材料),可以有效提升空穴的浓度,提升空穴的传输效率。如果将电子从空穴传输材料的HOMO能级移到掺杂剂的LUMO能级,形成空穴,称之为P型掺杂,所述掺杂剂即为P掺杂材料。
OLED器件常用的空穴传输材料为N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB),现有技术中使用的P掺杂材料虽拥有低LUMO能级,使之可以和NPB的HOMO能级匹配,但仍具有系列缺点,尤其是使用寿命方面的缺陷,严重影响材料的商业化运用。
发明内容
因此,本发明要解决的技术问题在于克服现有技术中的P掺杂材料寿命短的缺陷,从而提供一种稠环芳基化合物。
本发明要解决的另一个技术问题在于提供一种有机电子器件。
本发明要解决的另一个技术问题在于提供一种有机电子器件的应用。
为此,本发明提供一种稠环芳基化合物,具有式(I)或(Ⅱ)所示的结构,
其中,X1、X2、Y1各自独立地选自由连接键、N和CR6所组成的组合,环A和环B为共轭结构,R1-R4、R6中任一基团各自独立地与环A或环B以单键、双键连接,和/或R1-R4、R6中任意相邻的两个之间相互成环C,所述环C为吸电子环,R5选自连接键、R7取代或未取代C6-C30的芳基、R7取代或未取代C2-C30的杂芳基,R1-R4、R6、R7为吸电子基团。
进一步地,所述R1-R4和R6任一基团与环A或环B以单键连接,且所述R1-R4和R6各自独立地选自由氢、氘、卤素、氰基、硝基、R7取代或未取代的C1-C10的烷基、R7取代或未取代的C2-C10的烯基、R7取代或未取代的C2-C10的炔基、R7取代或未取代C6-C30的芳基和R7取代或未取代C2-C30的杂芳基所组成的组合;
所述R7选自由氘、卤素、氰基、硝基、R8取代或未取代的C1-C4的烷基、R8取代或未取代的C2-C4的烯基、R8取代或未取代的C2-C4的炔基、R8取代或未取代的C6-C20的芳基和R8取代或未取代的C2-C20的杂芳基所组成的组合;所述R8选自由氘、卤素、氰基和硝基所组成的组合。
进一步地,所述R1-R4和R6任一基团与环A或环B以双键连接,且各自独立地为氧或硫。
进一步地,所述R1-R4和R6任一基团与环A或环B以双键连接,且为其中两个R1’相同或不同;和/或为其中两个R2’相同或不同;和/或为其中两个R3’相同或不同;和/或为其中两个R4’相同或不同;和/或为其中两个R6’相同或不同,且R1’-R4’和R6’各自独立地选自由氢、氘、卤素、氰基、硝基、R7取代或未取代的C1-C10的烷基、R7取代或未取代的C2-C10的烯基、R7取代或未取代的C4-C10的环烯基、R7取代或未取代C4-C20的环烯酮、R7取代或未取代C4-C20的环烯硫酮、R7取代或未取代的C2-C10的炔基、R7取代或未取代C6-C30的芳基、R7取代或未取代C6-C30的芳酮基和R7取代或未取代C2-C30的杂芳基所组成的组合,或环A和/或环B上相邻两个取代基连接并与所述取代基所键合的碳原子一起形成环C’,其中,所述环C’选自由R7取代或未取代C4-C30的环烯基、R7取代或未取代C6-C30的芳基、R7取代或未取代C2-C30的杂芳基、R7取代或未取代C4-C30的环烯酮和R7取代或未取代C4-C30的环烯硫酮所组成的组合;
所述R7选自由氘、卤素、氰基、硝基、R8取代或未取代的C1-C4的烷基、R8取代或未取代的C2-C4的烯基、R8取代或未取代的C2-C4的炔基、R8取代或未取代的C6-C20的芳基和R8取代或未取代或的C2-C20的杂芳基所组成的组合;所述R8选自由氘、卤素、氰基和硝基所组成的组合。
进一步地,所述环C为R7取代或未取代C6-C30的芳基或R7取代或未取代C2-C30的杂芳基;
所述R7选自由氘、卤素、氰基、硝基、R8取代或未取代的C1-C4的烷基、R8取代或未取代的C2-C4的烯基、R8取代或未取代的C2-C4的炔基、R8取代或未取代的C6-C20的芳基和R8取代或未取代的C2-C20的杂芳基所组成的组合;所述R8选自由氘、卤素、氰基和硝基所组成的组合。
进一步地,所述烷基为C1-C4的烷基,所述烯基为C2-C4的烯基,所述炔基为C2-C4的炔基,所述芳基选自由苯基、联苯基、三联苯基、三亚苯基、四亚苯基、萘基、蒽基、萉基、菲基、芴基、芘基、苣基、苝基和薁基所组成的组合,所述杂芳基选自由二苯并噻吩基、二苯并呋喃基、二苯并硒吩基、呋喃基、噻吩基、苯并呋喃基、苯并噻吩基、苯并硒吩基、咔唑基、吲哚咔唑基、吡啶吲哚基、吡啶嘧啶基、吡咯并吡啶基、吡唑基、咪唑基、三唑基、恶唑基、噻唑基、恶二唑基、恶三唑基、二恶唑基、噻二唑基、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、恶嗪基、恶噻嗪基、恶二嗪基、吲哚基、苯并咪唑基、吲唑基、茚并嗪基、苯并恶唑基、苯并异恶唑基、苯并噻唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喔啉基、萘啶基、酞嗪基、蝶啶基、呫吨基、吖啶基、吩嗪基、吩噻嗪基、苯并噻吩并吡啶基、噻吩并二吡啶基、苯并噻吩并吡啶基、噻吩并二吡啶基、苯并硒吩并吡啶基、硒苯并二吡啶基、邻菲啰啉基、吡嗪并吡嗪基、噻吩酮基、苯并噻唑基和所组成的组合,其中“*”为连接位置。
进一步地,所述环烯酮或环烯硫酮选自如下基团:
其中,T1、T2各自独立地为O或S;“*”为连接位置。
进一步地,所述化合物具有如下结构:
其中,n1为0~2的整数,m1为0~2的整数,n2为0~2的整数,m2为0~2的整数;X3、Y1、Z1各自独立地为CR17或N;R9-R17为吸电子基团,化合物中不含氢原子。
进一步地,所述R9-R17各自独立地选自由氟、三氟甲基、氰基、硝基、R18全取代的苯基、R18全取代的吡嗪基、R18全取代的嘧啶基、R18全取代的吡啶基、R18全取代的三嗪基、R18全取代的环戊二烯基、R18全取代的乙烯基、R18全取代的苯甲酮基、R18全取代的和R18全取代的
所组成的组合,或R9-R17中相邻的两个基团连接并与所述取代基所键合的碳原子一起成环D,环D为R18全取代吡嗪基或R18全取代的萘基;R18取代基选自由氟、氰基、硝基和三氟甲基所组成的组合,R9-R17各自被多个R18取代时,R18可以相同也可以不同,“*”为连接位置。
进一步地,所述化合物具有如下结构:
本发明还提供一种有机电子器件,至少包含空穴注入层、空穴传输层、发光层和电子传输层,所述空穴注入层包括上述任一种所述的化合物。
进一步地,所述有机电子器件选自由有机发光二极管、有机太阳能电池、有机光导体、有机晶体管和照明元件所组成的组合。
本发明还提供一种有机电子器件在显示装置或照明装置中的应用。
本发明技术方案,具有如下优点:
1.本发明提供的稠环芳基化合物,结构为非平面结构(立体结构),分子间无堆叠,减少由高能激子产生的湮灭,促进阳极将空穴注入空穴传输层,避免焦耳热的产生,避免空穴传输层的分子发生堆栈和结晶,提高器件的寿命;母核为刚性结构,稳定性好,利于提高器件的稳定性,取代基为吸电子基团,使得化合物的LUMO能级在-4.6~-6.0eV,可以作为P-掺杂材料。
2.本发明提供的稠环芳基化合物,母核结构中不含活性氢,且取代基中也无氢原子,避免在器件制备工程中因发生化学反应而变质,有利于器件寿命的提高。
3.本发明提供的稠环芳基化合物,化合物引入氟原子,增强分子的电子注入和传输能力,化合物热稳定性高,成膜性好,利于器件寿命的提高;化合物为小分子,分子量小于1000,可以通过蒸发方式制备器件,避免π-π堆积导致的猝灭,从而提高效率。
附图说明
为了更清楚地说明本发明具体实施方式或现有技术中的技术方案,下面将对具体实施方式或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图是本发明的一些实施方式,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1是本发明实施例17中有机电致发光器件的结构示意图;
附图标记:
1-阳极层; 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-阴极层。
具体实施方式
提供下述实施例是为了更好地进一步理解本发明,并不局限于所述最佳实施方式,不对本发明的内容和保护范围构成限制,任何人在本发明的启示下或是将本发明与其他现有技术的特征进行组合而得出的任何与本发明相同或相近似的产品,均落在本发明的保护范围之内。
实施例中未注明具体实验步骤或条件者,按照本领域内的文献所描述的常规实验步骤的操作或条件即可进行。所用试剂或仪器未注明生产厂商者,均为可以通过市购获得的常规试剂产品。
实施例1
中间体1-P-1的合成:在250毫升三颈瓶中,氮气保护下加入4-溴-2,3,5,6-四氟苯甲腈(25.29克,1当量,0.1mol),四氢呋喃(80毫升),-78摄氏度条件下缓慢滴加正丁基锂(0.1mol),滴加完后,室温搅拌5小时,除溶剂,粗产物过硅胶柱(二氯甲烷:石油醚=10:1-5:1),得中间体1-P-1(13.22克,产率:38%)。
P-1的合成:在100毫升三颈瓶中,氮气保护下加入中间体1-P-1(3.48克,1当量,0.01mol),乙醇(30毫升),2,3-二氨基顺丁烯二氰(4.32克),缓慢加入叔丁醇钠(8当量),回流12小时,反应完成后,降至室温,加10毫升冰水猝灭,二氯甲烷萃取,浓缩物旋转蒸发,打浆(正己烷:二氯甲烷:乙腈=10:3:2)三遍,乙腈重结晶一遍,得P-1(2.57克,产率42%)。
元素分析:C30N18理论值:C,58.83;N,41.17;实测值:C,58.80;N,41.20;HRMS(ESI)m/z(M):理论值:612.0553;实测值:612.0561。
实施例2
中间体1-P-2的合成:同中间体1-P-1的合成,区别在于用2-溴-3,4,5,6-四氟苯甲腈替代4-溴-2,3,5,6-四氟苯甲腈,得中间体1-P-2(11.83克,产率34%)。
P-2的合成:同P-1的合成,区别在于用中间体1-P-2代替中间体1-P-1得P-2(2.75克,产量45%)。
元素分析:C30N18理论值:C,58.83;N,41.17;实测值:C,58.80;N,41.20;HRMS(ESI)m/z(M):理论值:612.0553;实测值:612.0560。
实施例3
中间体1-P-3的合成:同中间体1-P-1的合成,区别在于用1-溴-2,3,5,6-四氟-4-硝基苯(27.2克,1当量,0.1mol)替代4-溴-2,3,5,6-四氟苯甲腈,得中间体1-P-3(17.8克,产率46%)。
中间体2-P-3的合成:同P-1的合成,区别在于用中间体1-P-3(3.9克,1当量),替代中间体1-P-1,得中间体2-P-3(3.0克,产率46%)。
P-3的合成:50毫升三颈瓶中,氮气保护下,加入中间体2-P-3(6.5克,1当量,0.01mol),4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷(0.01mol),DMF(15毫升),150℃搅拌1小时,反应完成后冷却至室温,加入水和二氯甲烷的混合物(5:3),产物进入二氯甲烷层,分离后,(正己烷:二氯甲烷:乙腈=10:2:2)打浆三次得P-3(2.2克,产量36%)。
元素分析:C28N16F2理论值:C,56.20;N,37.45;实测值:C,56.25;N,37.42;HRMS(ESI)m/z(M):理论值:598.0460;实测值:598.0456。
实施例4
中间体1-P-5的合成:同中间体1-P-2的合成,区别在于用4-溴-2,3,5,6-四氟吡啶(22.9克,1当量,0.1mol)替代2-溴-3,4,5,6-四氟苯甲腈,得中间体1-P-5(9.60克,产率32%)。
P-5的合成:同P-2的合成,区别在于用中间体1-P-5(3克,1当量,0.01mol)替代中间体1-P-2,得P-5(2.7克,产量48%)。
元素分析:C26N18理论值:C,55.33;N,44.67;实测值:C,55.29;N,44.71;HRMS(ESI)m/z(M):理论值:564.0553;实测值:564.0559。
实施例5
中间体1-P-6的合成:同P-1的合成,区别在于用1-溴-2,3,5,6-四氟-4-硝基苯(0.01mol)替代中间体1-P-1,得中间体1-P-6(1.6克,产率39%)。
中间体2-P-6的合成:在50毫升三颈瓶中,加入中间体1-P-6(0.01mol),四氢呋喃(20毫升),-78摄氏度条件下滴加叔丁基锂(0.01mol),搅拌10分钟后,在室温下加入5-溴-2,4,6-三氟哌啶(0.01mol),室温搅拌2小时,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,过滤,除去有机溶剂,粗产物用(正己烷:乙腈=5:1)打浆3次,得中间体2-P-6(2.3克,产率51%)。
中间体3-P-6的合成:在50毫升三颈瓶中,氮气保护下加入中间体2-P-6(3.3克,0.01mol),5%Pd/C(5mmol),THF(10毫升),除去空气后,关闭氮气、通入氢气,搅拌2小时,反应完成后,过滤除去固体,旋转蒸发除去甲醇,得固体。
中间体4-P-6的合成:在50毫升三颈瓶中,加入上一步所得固体产物,硫酸(2mol/L,10mL),0摄氏度条件下缓慢加入亚硝酸钠(0.01mol)水溶液(1毫升),加完后,加入溴化亚铜(0.01mol),室温搅拌30分钟,粗产物用二氯甲烷萃取,浓缩所得固体产物用(正己烷:乙腈=5:1)打浆3次,得中间体4-P-6(2.1克,产率42%)。
P-6的合成:在100毫升三颈瓶中,氮气保护下,无水环境中加入中间体4-P-6(4.9克,1当量,0.01mol),THF(20毫升),-78摄氏度下加入正丁基锂(2当量),室温反应5小时,反应完成后,蒸发除去溶剂,所得产物用(正己烷:二氯甲烷:乙腈=10:3:2)打浆三次,再用乙腈打浆2次,得P-6(2.7克,产率33%)。
元素分析:C36N20F6理论值:C,52.31;N,33.89;实测值:C,52.27;N,33.93;HRMS(ESI)m/z(M):理论值:826.0519;实测值:826.0524。
实施例6
P-7的合成:同P-6的合成,区别在于用4-溴-2,3,5,6-四氟吡啶(2.3克,0.01mol)替代5-溴-2,4,6-三氟哌啶,得P-7(2.4克,产率28%)。
元素分析:C38N18F8理论值:C,53.04;N,29.30;实测值:C,53.09;N,29.27;HRMS(ESI)m/z(M):理论值:860.0426;实测值:860.0421。
实施例7
P-8的合成:同P-6的合成,区别在于用4-溴-2,3,5,6-四氟苯甲腈(2.5克,0.01mol)替代5-溴-2,4,6-三氟哌啶,得P-8(2.41克,产率28%)。
元素分析:C42N18F8理论值:C,55.52;N,27.75;实测值:C,55.57;N,27.71;HRMS(ESI)m/z(M):理论值:908.0426;实测值:908.0433。
实施例8
P-9的合成:同P-6的合成,区别在于用2-溴-4,6-二氟-1,3,5-三嗪(1.9克,0.01mol)替代5-溴-2,4,6-三氟哌啶,得P-9(4.12克,产率52%)。
元素分析:C34N22F4理论值:C,51.53;N,38.88;实测值:C,51.48;N,38.92;HRMS(ESI)m/z(M):理论值:792.0612;实测值:792.0605。
实施例9
P-10的合成:在100毫升三颈瓶中,氮气保护下加入中间体P-3(5.98克,1当量,0.01mol),丙二腈(1.32克,2当量),DMF(30毫升),0摄氏度下加入叔丁醇钠(2当量),滴加完成后升至120摄氏度,搅拌8小时,降至室温,加5毫升冰水猝灭,二氯甲烷萃取,浓缩物旋转蒸发,甲苯打浆3次,乙醇重结晶两次,得P-10(2.75克,产率40%)。
元素分析:C34N20理论值:C,59.31;N,40.69;实测值:C,59.27;N,40.73;HRMS(ESI)m/z(M):理论值:688.0615;实测值:688.0621。
实施例10
P-11的合成:同P-10的合成,区别在于用1,1,1,3,3,3-六氟丙烷(3.04克,2当量,0.02mol)替代丙二腈,得P-11(2.75克,产率40%)。
元素分析:C34N16F12理论值:C,47.46;N,26.05;实测值:C,47.43;N,26.09;HRMS(ESI)m/z(M):理论值:860.0300;实测值:860.0307。
实施例11
P-12的合成:同P-10的合成,区别在于用1,2,3,4-四氟环戊-1,3-二烯(2.76克,2当量,0.02mol)替代丙二腈,得P-12(3.66克,产率44%)。
元素分析:C38N16F8理论值:C,54.82;N,26.92;实测值:C,54.87;N,26.88;HRMS(ESI)m/z(M):理论值:832.0364;实测值:832.0359。
实施例12
P-13的合成:同P-10的合成,区别在于用4,5,6,7-四氟-1H-茚-1,3(2H)-二酮(4.36克,2当量,0.02mol)替代丙二腈,得P-13(3.66克,产率38%)。
元素分析:C46N16F8O4理论值:C,55.66;N,22.58;实测值:C,55.69;N,22.56;HRMS(ESI)m/z(M):理论值:992.0161;实测值:992.0168。
实施例13
中间体1-P17的合成:在250毫升三颈瓶中,氮气保护下加入2,3,4,5-四氟-2,4-环戊二烯-1-酮(15.20克,1当量,0.1mol),2,3-二氨基顺丁烯二氰(21.60克,2当量),乙醇(80毫升),室温下加入叔丁醇钠(4当量),后回流搅拌5小时,反应完成后,降至室温,加10毫升冰水猝灭,二氯甲烷萃取,浓缩物旋转蒸发,乙醇重结晶,得中间体1-P17(13.06克,产量46%)。
P17的合成:在100毫升三颈瓶中,氮气保护下加中间体1-P17(5.68克,2当量,0.02mol),2,2’(四氟-1,4-亚苯基)二乙腈(2.28克,1当量,0.01mol),加入四氢呋喃(30ml),叔丁醇钠(0.02mol),回流搅拌6小时,加入50毫升水淬灭,旋干溶剂,乙酸乙酯(50毫升×3)萃取,旋干溶剂,粗产物以层析纯化(乙酸乙酯/己烷,1/8),乙腈打浆3次,得到式(P-17)所示的稠杂环化合物(34.28克,产率56%)。
元素分析:C36N18F4理论值:C,56.86;N,33.15;实测值:C,56.89;N,33.12;HRMS(ESI)m/z(M):理论值:760.0489;实测值:760.0493。
实施例14
中间体1-P-23的合成:在100毫升三颈瓶中,氮气保护下加入全氟萘(2.72克,1当量,0.01mol),顺-1,1,1,4,4,4-六氟丁-2-烯-2,3-二胺(3.88克,2当量),DMF(20毫升),室温下缓慢加入叔丁醇钠(4当量),加完后室温至80℃,搅拌6小时,反应完成后,加水猝灭,二氯甲烷萃取,无水硫酸钠干燥,溶剂蒸发,(正己烷:乙腈=5:2)打浆三次,乙腈重结晶一次,得中间体1-P-23(2.5克,产率43%)。
P-23的合成:在50毫升三颈瓶中,氮气保护下加入中间体1-P-23(5.76克,1当量,0.01mol),吡啶(20毫升),三(二乙基胺)膦(0.02当量),在100摄氏度下搅拌1小时,反应完成后降温至室温,滴加5毫升水淬灭,二氯甲烷萃取,浓缩物旋转蒸发,所得混合物用乙醇重结晶,再二甲苯打浆3次,得P-23(3.12克,产率28%)。
元素分析:C36N30F8理论值:C,38.80;N,10.06;实测值:C,38.84;N,10.03;HRMS(ESI)m/z(M):理论值:1113.9767;实测值:1113.9761。
实施例15
中间体1-P-25的合成:同1-P-23,区别在于将全氟-1,8-二氮杂萘(2.38克,1当量,0.01mol)替换全氟萘,得中间体1-P-25(1.44克,产量39%)。
P-25的合成:同P-23的合成,区别在于用中间体1-P-25(3.7克,1当量)替换中间体1-P-23,得P-25(2.46克,产率35%)。
元素分析:C32N20F2理论值:C,54.71;N,39.88;实测值:C,54.73;N,39.86;HRMS(ESI)m/z(M):理论值:702.0583;实测值:702.0578。
实施例16
中间体1-P-29的合成:同1-P-23,区别在于将2,3-二氨基顺丁烯二氰(1.1克,1当量,0.01mol)替换顺-1,1,1,4,4,4-六氟-2-丁烯-2,3-二胺,得中间体1-P-29(1.09克,产量27%)。
P-29的合成:同P-23的合成,区别在于用中间体1-P-29(4.0克,1当量,0.01mol)替换1-P-23,得P-29(2.7克,产率35%)。
元素分析:C36N16F6理论值:C,56.12;N,29.09;实测值:C,56.17;N,29.06;HRMS(ESI)m/z(M):理论值:770.0396;实测值:770.0403。
实施例17
制备有机电致发光器件:
将ITO透明基板放置在蒸镀设备中,其中ITO(铟锡氧化物)作为阳极层1,依次蒸镀10nm空穴注入层2、100nm空穴传输层3(HTL)、50nm有机发光层4(EML)、40nm电子传输层5(ETL)、1nm电子注入层6(EIL)、80nm阴极层7,其中使用,N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺作为空穴传输层3,3wt%Ir(piq)3:CBP作为有机发光层4,BPhen作为电子传输层5,LiF作为电子注入层6,Al作为阴极层7使所述器件形成如图1所示的具体结构。
步骤:
(1)基板清理:将涂布了ITO的透明电机基板在水性清洗剂(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)蒸镀有机发光功能层
把上述带有阳极层1的玻璃基片置于真空腔内,抽真空至1×10-6至2×10-4Pa,在上述阳极层1膜上真空蒸镀空穴注入层材料(P-掺杂材料)作为空穴注入层2,蒸镀速率为0.1nm/s,蒸镀厚度为10nm;
在空穴注入层2上蒸镀N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺作为空穴传输层3,蒸镀速率为0.1nm/s,蒸镀膜厚为100nm;
在空穴传输层3之上蒸镀有机发光层4,有机发光层4由(3wt%Ir(piq)3:CBP)作为有机发光层材料。具体制备方法为:以共蒸的方式真空蒸镀发光主体材料掺杂材料,主体材料蒸镀速率为0.09nm/s,掺杂染料蒸镀速率为0.01nm/s,蒸镀总膜厚为50nm;
在有机发光层4上真空蒸镀一层(BPhen)为器件的电子传输层5,蒸镀速率为0.1nm/s,蒸镀总膜厚为40nm;
在电子传输层5上真空蒸镀一层LiF,为器件的电子注入层6,其蒸镀速率为0.05nm/s,蒸镀总膜厚为1nm;
在电子注入层6蒸镀Al作为器件的阴极层7,其蒸镀速率为0.1nm/s,蒸镀总膜厚为80nm。
其中,在一个对比试验中,选用常用的HAT(CN)6作为空穴注入层材料,HAT(CN)6具有如下所示化学结构:
其余实验例中以本发明所述化合物作为空穴注入层材料。
空穴传输层材料的结构式如下:
有机发光层材料为:
电子传输层材料的结构式为:
表1为本申请所述化合物的热分解温度(Td)及LUMO能级。
表2为用本申请所述化合物及HAT(CN)6作为空穴注入层材料的有机电致发光器件的性能参数。
测试条件:
(1)热分解温度:使用热重分析仪(TGA美国TA TGA55)对样品进行热分解温度测试,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Td;
(2)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)对本发明实施例1~16所得化合物的LUMO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:
(3)器件的电流、亮度、寿命等特性测试:采用PR 650光谱扫描亮度计和KeithleyK 2400数字源表系统同步测试;测试条件:电流密度为10mA/cm2,温度为25℃。
表1
表2
相比对比例1本发明化合物制备的器件寿命提高,本发明化合物结构为非平面结构(立体结构),分子间无堆叠,减少由高能激子产生的湮灭,促进阳极将空穴注入空穴传输层,避免焦耳热的产生,避免空穴传输层的分子发生堆栈和结晶,提高器件的寿命。
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (13)
2.根据权利要求1所述的稠环芳基化合物,其特征在于,所述R1-R4和R6任一基团与环A或环B以单键连接,且所述R1-R4和R6各自独立地选自由氢、氘、卤素、氰基、硝基、R7取代或未取代的C1-C10的烷基、R7取代或未取代的C2-C10的烯基、R7取代或未取代的C2-C10的炔基、R7取代或未取代C6-C30的芳基和R7取代或未取代C2-C30的杂芳基所组成的组合;
所述R7选自由氘、卤素、氰基、硝基、R8取代或未取代的C1-C4的烷基、R8取代或未取代的C2-C4的烯基、R8取代或未取代的C2-C4的炔基、R8取代或未取代的C6-C20的芳基和R8取代或未取代的C2-C20的杂芳基所组成的组合;所述R8选自由氘、卤素、氰基和硝基所组成的组合。
3.根据权利要求1所述的稠环芳基化合物,其特征在于,所述R1-R4和R6任一基团与环A或环B以双键连接,且各自独立地为氧或硫。
4.根据权利要求1所述的稠环芳基化合物,其特征在于,所述R1-R4和R6任一基团与环A或环B以双键连接,且为其中两个R1’相同或不同;和/或为其中两个R2’相同或不同;和/或为其中两个R3’相同或不同;和/或为其中两个R4’相同或不同;和/或为其中两个R6’相同或不同,且R1’-R4’和R6’各自独立地选自由氢、氘、卤素、氰基、硝基、R7取代或未取代的C1-C10的烷基、R7取代或未取代的C2-C10的烯基、R7取代或未取代的C4-C10的环烯基、R7取代或未取代C4-C20的环烯酮、R7取代或未取代C4-C20的环烯硫酮、R7取代或未取代的C2-C10的炔基、R7取代或未取代C6-C30的芳基、R7取代或未取代C6-C30的芳酮基和R7取代或未取代C2-C30的杂芳基所组成的组合,或环A和/或环B上相邻两个取代基连接并与所述取代基所键合的碳原子一起形成环C’,其中,所述环C’选自由R7取代或未取代C4-C30的环烯基、R7取代或未取代C6-C30的芳基、R7取代或未取代C2-C30的杂芳基、R7取代或未取代C4-C30的环烯酮和R7取代或未取代C4-C30的环烯硫酮所组成的组合;
所述R7选自由氘、卤素、氰基、硝基、R8取代或未取代的C1-C4的烷基、R8取代或未取代的C2-C4的烯基、R8取代或未取代的C2-C4的炔基、R8取代或未取代的C6-C20的芳基和R8取代或未取代或的C2-C20的杂芳基所组成的组合;所述R8选自由氘、卤素、氰基和硝基所组成的组合。
5.根据权利要求1所述的稠环芳基化合物,其特征在于,所述环C为R7取代或未取代C6-C30的芳基或R7取代或未取代C2-C30的杂芳基;
所述R7选自由氘、卤素、氰基、硝基、R8取代或未取代的C1-C4的烷基、R8取代或未取代的C2-C4的烯基、R8取代或未取代的C2-C4的炔基、R8取代或未取代的C6-C20的芳基和R8取代或未取代的C2-C20的杂芳基所组成的组合;所述R8选自由氘、卤素、氰基和硝基所组成的组合。
6.根据权利要求2、4或5所述的稠环芳基化合物,其特征在于,所述烷基为C1-C4的烷基,所述烯基为C2-C4的烯基,所述炔基为C2-C4的炔基,所述芳基选自由苯基、联苯基、三联苯基、三亚苯基、四亚苯基、萘基、蒽基、萉基、菲基、芴基、芘基、苣基、苝基和薁基所组成的组合,所述杂芳基选自由二苯并噻吩基、二苯并呋喃基、二苯并硒吩基、呋喃基、噻吩基、苯并呋喃基、苯并噻吩基、苯并硒吩基、咔唑基、吲哚咔唑基、吡啶吲哚基、吡啶嘧啶基、吡咯并吡啶基、吡唑基、咪唑基、三唑基、恶唑基、噻唑基、恶二唑基、恶三唑基、二恶唑基、噻二唑基、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、恶嗪基、恶噻嗪基、恶二嗪基、吲哚基、苯并咪唑基、吲唑基、茚并嗪基、苯并恶唑基、苯并异恶唑基、苯并噻唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喔啉基、萘啶基、酞嗪基、蝶啶基、呫吨基、吖啶基、吩嗪基、吩噻嗪基、苯并噻吩并吡啶基、噻吩并二吡啶基、苯并噻吩并吡啶基、噻吩并二吡啶基、苯并硒吩并吡啶基、硒苯并二吡啶基、邻菲啰啉基、吡嗪并吡嗪基、噻吩酮基、苯并噻唑基和所组成的组合,其中“*”为连接位置。
11.一种有机电子器件,至少包含空穴注入层、空穴传输层、发光层和电子传输层,其特征在于,所述空穴注入层包括权利要求1-9中任一项所述的化合物。
12.根据权利要求11所述的有机电子器件,其特征在于,所述有机电子器件选自由有机发光二极管、有机太阳能电池、有机光导体、有机晶体管和照明元件所组成的组合。
13.权利要求11或12所述的有机电子器件在显示装置或照明装置中的应用。
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