CN109503391A - 一种芴类化合物及其有机发光器件 - Google Patents
一种芴类化合物及其有机发光器件 Download PDFInfo
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Abstract
本发明提供一种芴类化合物及其有机发光器件,涉及有机光电材料技术领域。本发明通过在芳胺类主体上连接三亚苯基、芴基或苯基芴基或螺芴基,得到一种芴类化合物,应用于有机发光器件中作为空穴传输层,可有效提高空穴的传输及减少电子向阳极的逸散,提高空穴和电子在发光层的复合率,提高器件的发光效率,其热稳定性好,成膜性好,合成简单易操作,可作为空穴传输层,有效解决有机发光器件中载流子传输不平衡的问题,其有机发光器件具有发光效率高的优点。
Description
技术领域
本发明涉及有机光电材料技术领域,尤其涉及一种芴类化合物及其有机发光器件。
背景技术
最早的有机电致发光现象发现于1963年。当时利用有机蒽晶体作为发光材料。由于该器件的驱动电压高达400V,而且器件的效率和寿命都远不及无机电致发光器件,因此有机电致发光在当时并未引起人们足够的重视。1987年Tang和Van Silyke利用真空沉积镀膜的方法,首次用芳胺衍生物HTM1作为空穴传输层,8-羟基喹啉铝(Alq3)作为发光层,实现了在10V的驱动电压下,亮度为1000cd/m2的绿光发射,而且器件的效率为1.5lm/W,寿命在100h以上。自此,有机发光器件由于其体积小、重量轻、移动电压低、响应快、视角广以及可实现大面积全色平板显示等优点而成为研究的热点并有着极好的商业和市场前景。多年来的研究不仅在有机电致发光理论上,而且在器件的实用性能,如亮度、驱动电压、寿命等诸多方面都有了长足的发展。
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,譬如,用于有机电致发光研究的空穴传输材料,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。
总体来看,未来OLED的方向是发展高效率、高亮度、长寿命、低成本的白光器件和全彩色显示器件,但该技术的产业化进程仍面临许多关键问题,如何平衡载流子注入,如何提高光耦合输出效率成为亟待解决的问题。
发明内容
本发明的目的是提供一种芴类化合物及其有机发光器件,本发明提供的有机化合物具有良好的空穴传输及电子阻挡性能,热稳定性好,成膜性好,合成方法简单易操作,使用该芴类化合物制备的有机发光器件具有良好的发光效率。
本发明提供了一种芴类化合物,其分子结构通式如化学式Ⅰ所示:
其中,Ar1、Ar2独立地选自取代或未取代的C6~C25芳基、取代或未取代的C3~C18杂芳基中的一种;
R1、R2独立地选自C1~C10烷基、C6~C25芳基中的一种,其中R1、R2可连接成环。
优选的,其分子结构通式如化学式Ⅱ、Ⅲ、Ⅳ所示:
优选的,Ar1、Ar2选自如下所示的基团:
其中,R3、R4、R5、R6、R7独立地选自H、甲基、乙基、异丙基、叔丁基、苯基、萘基、蒽基、菲基、芘基、芴基、螺二芴基、芴基、吡啶基、吩噻嗪基、吩噁嗪基、吖啶基、二苯并噻吩基、二苯并呋喃基、苯并噻吩基、苯并呋喃基中的任意一种;
R8选自甲基、乙基、异丙基、叔丁基、取代或未取代的苯基、取代或未取代的萘基中的任意一种,其中取代基为甲基、乙基、异丙基、叔丁基、苯基、萘基中的任意一种或多种。
优选的,Ar1、Ar2选自如下所示的基团:
最优选,本发明的芴类化合物选自如下所示化学结构中的任意一种:
本发明还提供了一种有机发光器件,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物层,所述的有机物层含有本发明所述的任一种芴类化合物。
优选的,本发明所述有机物层包括空穴传输层,空穴传输层中含有本发明所述的任一种芴类化合物。
本发明的有益效果:
本发明提供一种芴类化合物及其有机发光器件。本发明通过在芳胺类主体结构上,连接三亚苯基、芴基或苯基芴基或螺芴基,一方面,该组合方式形成的芴类化合物具有良好的空穴传输能力及电子阻挡能力,应用于有机发光器件中作为空穴传输层,可有效提高空穴的传输及减少电子向阳极的逸散,提高空穴和电子在发光层的复合率,提高器件的发光效率。
一方面,该组合方式增大了共轭体系,使得电荷更加分散,提高了材料的稳定性。
一方面,该组合方式,三亚苯基、苯基、联苯基、萘基等基团的引入,既可以增加化合物的分子量,从而提高玻璃化温度而不易结晶,又降低了分子的共平面性,易于成膜。
本发明所述芴类化合物制备方法简单,原料易得,能够满足工业化需求。
本发明所述芴类化合物应用于有机发光器件中,可作为空穴传输层,采用本发明所述芴类化合物制备的有机发光器件具有良好的发光效率。
具体实施方式:
下面将结合本发明实施例的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明的保护范围。
本发明提供了一种芴类化合物,其分子结构通式如化学式Ⅰ所示:
其中,Ar1、Ar2独立地选自取代或未取代的C6~C25芳基、取代或未取代的C3~C18杂芳基中的一种;
R1、R2独立地选自C1~C10烷基、C6~C25芳基中的一种,其中R1、R2可连接成环。
优选的,其分子结构通式如化学式Ⅱ、Ⅲ、Ⅳ所示:
优选的,Ar1、Ar2选自如下所示的基团:
其中,R3、R4、R5、R6、R7独立地选自H、甲基、乙基、异丙基、叔丁基、苯基、萘基、蒽基、菲基、芘基、芴基、螺二芴基、芴基、吡啶基、吩噻嗪基、吩噁嗪基、吖啶基、二苯并噻吩基、二苯并呋喃基、苯并噻吩基、苯并呋喃基中的任意一种;
R8选自甲基、乙基、异丙基、叔丁基、取代或未取代的苯基、取代或未取代的萘基中的任意一种,其中取代基为甲基、乙基、异丙基、叔丁基、苯基、萘基中的任意一种或多种。
优选的,Ar1、Ar2选自如下所示的基团:
最优选,作为举例,没有特别限定,本发明所述的一种芴类化合物选自如下所示化学结构中的任意一种:
本发明的芴类化合物通过一系列Buchward偶联反应等合成本发明所述的化学式Ⅰ结构的芴类化合物。
本发明对上述反应没有特殊的限制,采用本领域技术人员所熟知的常规反应即可,该制备方法简单,易于操作。
本发明还提供了一种有机发光器件,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物层,所述的有机物层含有本发明所述的芴类化合物。
优选的,所述有机物层包括主体材料,主体材料中含有本发明所述的任一种芴类化合物。
优选的,本发明所述的发光层主体材料选自ADN、CBP、mCP、TCTA、α-ADN、4P-NPB、TCP等,其可以是单一物质构成的单层结构,也可是不同物质形成的单层结构或多层结构。
优选的,本发明所述绿光发光层客体选自Ir(ppy)3、Ir(ppy)2(acac)、DMQA、DBQA、TMDBQA等。
本发明对上述反应没有特殊的限制,采用本领域技术人员所熟知的常规反应即可,该制备方法简单,易于操作。
本发明还提供了一种有机发光器件,所述有机发光器件包括阴极、阳极和置于所述两电极之间及之外的一个或多个有机物层,所述的有机物层含有本发明所述的芴类化合物。
优选的,所述有机物层包括空穴传输层,空穴传输层中含有本发明所述的任一种芴类化合物。
本发明所述的有机发光器件结构为:ITO作为透明阳极;2-TNATA用作空穴注入层;NPB或本发明所述的芴类化合物作为空穴传输层;CBP/Ir(ppy)3用作发光层物质;TPBi用作电子传输层;LiF用作电子注入层;Al用作阴极。
本发明所述的芴类化合物用作空穴传输材料,用以制造有以下相同构造的有机发光器件:
ITO/2-TNATA(50nm)/本发明所述的芴类化合物(30nm)/CBP:Ir(ppy)3(30nm)/TPBi(30nm)/LiF(0.5nm)/Al(200nm)。
本发明所述的芴类化合物及其有机发光器件其结构优选为:基板/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/阴极。然而,有机发光器件的结构不限于此。本发明所述的芴类化合物及其有机发光器件可根据器件参数要求及材料的特性进行选择及组合,也可增加或省略部分有机层。
本发明所述有机发光器件可广泛应用于面板显示、照明光源、柔性OLED、电子纸、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。
[实施例1]化合物1的合成
Step1:反应器中加入2-氨基-9,9-二甲基芴(1.67g,8mmol)、2-溴-三亚苯(2.05g,6.67mmol)、Pd2(dba)3(0.17g,0.2mmol)、P(t-Bu)3(0.14,0.67mmol)、NaOt-Bu(2.24g,20mmol)、甲苯溶液100mL,100℃条件下反应24h,反应结束后用***和水萃取有机相,有机层用MgSO4干燥,浓缩有机物,过柱层析、重结晶得到中间体1-a(1.56g,73%)。
Step2:反应器中加入苯胺(0.75g,8mmol)、溴苯(1.05g,6.67mmol)、Pd2(dba)3(0.17g,0.2mmol)、P(t-Bu)3(0.14,0.67mmol)、NaOt-Bu(2.24g,20mmol)、甲苯溶液100mL,100℃条件下反应24h,反应结束后用***和水萃取有机相,有机层用MgSO4干燥,浓缩有机物,过柱层析、重结晶得到中间体1-b(1.43g,75%)。
Step3:反应容器里加入中间体1-a(2.68g,8.4mmol)、4,4’-二溴-1,1-联苯(2.87g,9.2mmol)、叔丁醇钾(2.83g,25.2mmol)、Pd2(dba)3(0.07g,0.08mmol)、超声除氧的二甲苯40mL,搅拌溶解,置换空气三次,加入P(t-Bu)3(0.07g,0.34mmol),再次置换空气三次,回流反应6h,冷却至室温,加入足量的二氯甲烷使得产品完全溶解,过少量硅胶漏斗,除掉催化剂和盐,滤液浓缩至粘稠状,过柱层析,得到化合物1-c(3.14g,68%)。
Step4:反应容器里加入中间体1-c(4.62g,8.4mmol)、中间体1-b(2.63g,9.2mmol)、叔丁醇钾(2.83g,25.2mmol)、Pd2(dba)3(0.07g,0.08mmol)、超声除氧的二甲苯40mL,搅拌溶解,置换空气三次,加入P(t-Bu)3(0.07g,0.34mmol),再次置换空气三次,回流反应6h,冷却至室温,加入足量的二氯甲烷使得产品完全溶解,过少量硅胶漏斗,除掉催化剂和盐,滤液浓缩至粘稠状,过柱层析,得到化合物1(4.12g,65%)。
质谱m/z:754.34(计算值:754.33)。理论元素含量(%)C57H42N2:C,90.68;H,5.61;N,3.71实测元素含量(%):C,90.68;H,5.60;N,3.72。上述结果证实获得产物为目标产品。
[实施例2]化合物2的合成
按照化合物1的合成方法得到化合物2(4.72g,62%)。
质谱m/z:906.41(计算值:906.40)。理论元素含量(%)C69H50N2:C,91.36;H,5.56;N,3.09实测元素含量(%):C,91.36;H,5.57;N,3.08。上述结果证实获得产物为目标产品。
[实施例3]化合物4的合成
按照化合物1的合成方法得到化合物4(4.14g,63%)。
质谱m/z:782.38(计算值:782.37)。理论元素含量(%)C59H46N2:C,90.50;H,5.92;N,3.58实测元素含量(%):C,90.51;H,5.91;N,3.58。上述结果证实获得产物为目标产品。
[实施例4]化合物5的合成
按照化合物1的合成方法得到化合物5(4.53g,63%)。
质谱m/z:854.38(计算值:854.37)。理论元素含量(%)C65H46N2:C,91.30;H,5.42;N,3.28实测元素含量(%):C,91.31;H,5.40;N,3.29。上述结果证实获得产物为目标产品。
[实施例5]化合物8的合成
按照化合物1的合成方法得到化合物8(4.65g,61%)。
质谱m/z:906.41(计算值:906.40)。理论元素含量(%)C69H50N2:C,91.36;H,5.56;N,3.09实测元素含量(%):C,91.37;H,5.55;N,3.09。上述结果证实获得产物为目标产品。
[实施例6]化合物24的合成
按照化合物1的合成方法得到化合物24(4.43g,60%)。
质谱m/z:878.38(计算值:878.37)。理论元素含量(%)C67H46N2:C,91.54;H,5.27;N,3.19实测元素含量(%):C,91.55;H,5.26;N,3.19。上述结果证实获得产物为目标产品。
[实施例7]化合物59的合成
按照化合物1的合成方法得到化合物59(4.35g,59%)。
质谱m/z:876.36(计算值:876.35)。理论元素含量(%)C67H44N2:C,91.75;H,5.06;N,3.19实测元素含量(%):C,91.75;H,5.07;N,3.18。上述结果证实获得产物为目标产品。
[实施例8]化合物69的合成
按照化合物1的合成方法得到化合物69(4.43g,60%)。
质谱m/z:878.38(计算值:878.37)。理论元素含量(%)C67H46N2:C,91.54;H,5.27;N,3.19实测元素含量(%):C,91.55;H,5.26;N,3.19。上述结果证实获得产物为目标产品。
[实施例9]化合物93的合成
按照化合物1的合成方法得到化合物93(4.35g,59%)。
质谱m/z:876.36(计算值:876.35)。理论元素含量(%)C67H44N2:C,91.75;H,5.06;N,3.19实测元素含量(%):C,91.75;H,5.07;N,3.18。上述结果证实获得产物为目标产品。
[对比实施例1]器件制备实施例:
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/30nm、蒸镀主体CBP:掺杂Ir(ppy)3 5%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、2、4、5、8、24、59、69、93。
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,本发明的芴类化合物应用于有机发光器件中,尤其是作为空穴传输层,其有机发光器件的发光效率显著提高,本发明的芴类化合物是性能良好的有机发光材料。
应当指出,本发明用个别实施方案进行了特别描述,但在不脱离本发明原理的前提下,本领域普通技术人可对本发明进行各种形式或细节上的改进,这些改进也落入本发明的保护范围内。
Claims (7)
1.一种芴类化合物,其特征在于,其分子结构通式如化学式Ⅰ所示:
其中,Ar1、Ar2独立地选自取代或未取代的C6~C25芳基、取代或未取代的C3~C18杂芳基中的一种;
R1、R2独立地选自C1~C10烷基、C6~C25芳基中的一种,其中R1、R2可连接成环。
2.根据权利要求1所述的一种芴类化合物,其特征在于,其分子结构通式如化学式Ⅱ、Ⅲ、Ⅳ所示:
3.根据权利要求1所述的一种芴类化合物,其特征在于,Ar1、Ar2选自如下所示的基团:
其中,R3、R4、R5、R6、R7独立地选自H、甲基、乙基、异丙基、叔丁基、苯基、萘基、蒽基、菲基、芘基、芴基、螺二芴基、咔唑基、吡啶基、吩噻嗪基、吩噁嗪基、吖啶基、二苯并噻吩基、二苯并呋喃基、苯并噻吩基、苯并呋喃基中的任意一种;
R8选自甲基、乙基、异丙基、叔丁基、取代或未取代的苯基、取代或未取代的萘基中的任意一种,其中取代基为甲基、乙基、异丙基、叔丁基、苯基、萘基中的任意一种或多种。
4.根据权利要求1所述的一种芴类化合物,其特征在于,Ar1、Ar2选自如下所示的基团:
5.根据权利要求1所述的一种芴类化合物,其特征在于,选自如下所示化学结构中的任意一种:
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物层,所述的有机物层含有权利要求1~5任一项所述的芴类化合物。
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,所述有机物层包括空穴传输层,空穴传输层中含有权利要求1~5任一项所述的芴类化合物。
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