CN100491351C - 聚合物电荷迁移组分和由其制得的电子器件 - Google Patents

聚合物电荷迁移组分和由其制得的电子器件 Download PDF

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CN100491351C
CN100491351C CNB038161850A CN03816185A CN100491351C CN 100491351 C CN100491351 C CN 100491351C CN B038161850 A CNB038161850 A CN B038161850A CN 03816185 A CN03816185 A CN 03816185A CN 100491351 C CN100491351 C CN 100491351C
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heteroaryl
aryl
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CN1666357A (zh
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N·海隆
N·S·拉杜
E·M·史密斯
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EIDP Inc
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EI Du Pont de Nemours and Co
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Abstract

本发明涉及一种聚合物电荷迁移组分。本发明还涉及电子器件，其至少一层活性层包括这种电荷迁移组合物。

Description

聚合物电荷迁移组分和由其制得的电子器件
相关申请
本申请要求2002年7月10日提交的美国临时申请60/394767和2003年3月28日提交的美国临时申请60/458277的优先权。
技术领域
本发明涉及聚合物电荷迁移组分(composition)。本发明还涉及电子器件，它具有至少一层含这种电荷迁移组分的活性层。
背景技术
在有机光活性电子器件(例如制造有机发光二极管显示器的发光二极管(OLED))中，有机活性层夹在有机发光二极管显示器的两层电气接触层之间。在有机发光二极管中，通过向两层透光电接触层施加电压，所述有机光活性层透过所述电气接触层发射光线。
已知在发光二极管中使用有机场致发光化合物作为活性组分。业已使用简单的有机分子、共轭聚合物和有机金属配合物。
使用光活性物质的器件通常包括一层或多层电荷迁移层，该电荷迁移层位于光活性(例如发光)层和一层所述电气接触层之间。一层空穴迁移层可位于所述光活性层和空穴注入接触层(也称为阳极(anode))之间。一层电子迁移层可位于所述光活性层和电子注入接触层(也称为阴极(cathode))之间。
仍然需要开发电荷迁移物质。
发明的概述
本发明涉及已知电荷迁移组分，它是一种低聚物或聚合物。在本文中，术语“聚合物”的范围包括具有一种或多种不同类型的单体单元的聚合物和低聚物，并指至少具有两个重复的单体单元的化合物。术语“聚合物的”与术语“聚合物”具有相同的范围。
在一个实例中，本发明涉及聚合物电荷迁移组分，它含有至少一种图1所示的式1(a)第一单体单元，其中：
Ar1可相同或不同，各自选自芳基和杂芳基；
Ar2可相同或不同，各自选自亚芳基和亚杂芳基；
R1可相同或不同，各自选自H、烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、CnHaFb和C6HcFd；或者相邻的R1基团可连接在一起形成5元或6元环；
n是整数；
a、b、c和d为0或整数，使得a+b＝2n+1，c+d＝5。
在一个实例中，本发明涉及一种聚合物电荷迁移组分，它含有至少一种式1(b)的第一单体单元：
Figure C03816185D00051
其中，Ar1可相同或不同，各自选自芳基和杂芳基；
Ar2可相同或不同，各自选自亚芳基和亚杂芳基；
R5可相同或不同，各自选自H、F、Cl、Br、羟基、羧基、羰基、甲硅烷基、甲硅烷氧基、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHaFb、OCnHaFb、C6HcFd和OCbHcFd；或者两个R5基团一起形成一个亚芳基或杂亚芳基；
a、b、c和d为0或整数，使得a+b＝2n+1，c+d＝5；
n是整数(如上所述)；
y是0或1-3的整数；
z是0或1-4的整数。
在一个实例中，本发明涉及一种聚合物电荷迁移组分，它含有至少一种图1式1(c)的第一单体单元：
Figure C03816185D00061
其中，Ar1可相同或不同，各自选自芳基和杂芳基；
Ar2可相同或不同，各自选自亚芳基和亚杂芳基；
R1可相同或不同，各自选自H、烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、CnHaFb和C6HcFd；或者相邻的R1基团可连接在一起形成5元或6元环；
R5可相同或不同，各自选自H、F、Cl、Br、羟基、羧基、羰基、甲硅烷基、甲硅烷氧基、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHaFb、OCnHaFb、C6HcFd和OCbHcFd；或者两个R5基团一起形成一个亚芳基或杂亚芳基；
a、b、c和d为0或整数，使得a+b＝2n+1，c+d＝5；
n是整数(如上所述)；
y是0或1-3的整数；
z是0或1-4的整数。
在一个实例中，本发明涉及一种聚合物电荷迁移组分，它含有至少一种选自图2式II(a)、II(b)和II(c)的第一单体单元，其中：
R2和R3可相同或不同，各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd；
R4可相同或不同，各自选自亚烷基、亚杂烷基、亚烯基、亚芳基、亚杂芳基、亚炔基或亚芳基亚炔基；
a、b、c和d为0或整数，使得a+b＝2n+1，c+d＝5；
n是整数；
p是0或1；
x是0、1或2；
y是0或1-3的整数。
在一个实例中，本发明涉及一种聚合物电荷迁移组分，它含有至少一种选自上述图2式II(a)、II(b)和II(c)的第一单体单元，并且在芳香基团上至少具有一个选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的取代基。
在一个实例中，本发明涉及一种聚合物电荷迁移组分，它含有至少一种选自图3式III(a)、III(b)、III(c)和III(d)的第一单体单元，其中：
R4可相同或不同，各自选自亚烷基、亚杂烷基、亚烯基、亚芳基、亚杂芳基或亚芳基亚炔基；
R5可相同或不同，各自选自H、F、Cl、Br、羟基、羧基、羰基、甲硅烷基、甲硅烷氧基、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd；或者两个R5基团一起形成一个亚芳基或杂亚芳基；
a、b、c和d为0或整数，使得a+b＝2n+1，c+d＝5；
n是整数；
x是0、1或2；
y是0或1-3的整数；
z是0或1-4的整数。
在一个实例中，本发明涉及一种聚合物电荷迁移组分，它含有至少一种选自上述图1的式I(a)、I(b)和I(c)的第一单体单元、至少一种选自上述图2的式II(a)-II(c)以及上述图3的式III(a)、III(b)、III(c)和III(d)的第二单体单元。
在一个实例中，本发明涉及一种具有至少一层活性层的电子器件，所述活性层包括含有至少一种第一单体单元的聚合物，所述单体单元选自图1-3所示的式I(a)、I(b)、I(c)、II(a)、II(b)、II(c)、III(a)、III(b)、III(c)和III(d)，其中，Ar1、Ar2、R1-R5、a-d、n、p和x-z如上所定义。
在一个实例中，本发明涉及一种具有至少一层活性层的电子器件，所述活性层包括含有至少一种上述图1所示的式I(a)、I(b)、I(c)的第一单体单元和至少一种上述图2所示的式II(a)、II(b)、II(c)以及上述图3所示的式III(a)、III(b)、III(c)和III(d)的第二单体单元的聚合物。
在本文中，术语“电荷迁移组分”是指一种材料，它能从电极接受电荷，使之沿该材料的厚度以相对高的效率迁移，并且电荷的损耗小。空穴迁移组分能够接受来自阳极的正电荷并迁移之。电子迁移组分能够接受来自阴极的负电荷并迁移之。
术语“抗淬灭组分”是指一种材料，它能够防止、延缓或者减少光活性层激发态的能量迁移和电子迁移。
术语“光活性”是指呈现场致发光、光致发光和/或光敏感性的任何材料。
术语“HOMO”是指化合物的最高占据分子轨道。
术语“LUMO”是指化合物的最低未占据分子轨道。
术语“基团”是指化合物的一部分，例如有机化合物中的取代基。
前缀“杂”是指一个或多个碳原子被一个不同原子所取代。
术语“烷基”是指具有一个连接点位的由脂肪烃衍生的基团，该基团可以是未取代的或者是取代的。
术语“杂烷基”是指由至少具有一个杂原子的脂肪烃形衍生的并具有一个连接点位的基团，该基团可以是取代的或者是未取代的。
术语“亚烷基”是指具有两个或多个连接点位的由脂肪烃衍生的基团。
术语“亚杂烷基”是指具有两个或多个连接点位的由具有至少一个杂原子的脂肪烃衍生的基团。
术语“烯基”是指具有一个连接点位的由具有一根或多根碳-碳双键的烃衍生的基团，该基团可以是未取代的或者是取代的。
术语“炔基”是指具有一个连接点位的由具有一根或多根碳-碳三键的烃衍生的基团，该基团可以是未取代的或者是取代的。
术语“亚烯基”是指具有两个或多个连接点位的由具有一根或多根碳-碳双键的烃衍生的基团，该基团可以是未取代的或者是取代的。
术语“亚炔基”是指具有两个或多个连接点位的由具有一根或多根碳-碳三键的烃衍生的基团，该基团可以是未取代的或者是取代的。
术语“杂烯基”、“亚杂烯基”、“杂炔基”、“亚杂炔基”是指具有一个或多个杂原子的类似基团。
术语“亚杂烷基”是指由具有至少一个杂原子的脂肪烃衍生并具有两个或多个连接点位的基团。
术语“芳基”是指具有一个连接点位、由芳香烃衍生的基团，该基团可以是未取代的或者是取代的。
术语“杂芳基”是指具有一个连接点位的由具有至少一个杂原子的芳香基团衍生的基团，该基团可以是未取代的或者是取代的。
术语“芳烷基”是指具有一个芳基取代基的烷基衍生的基团，该基团可以进一步被取代或未取代。
术语“杂芳烷基”是指具有杂芳基取代基的烷基衍生的基团，该基团可进一步被取代或未取代。
术语“亚芳基”是指由芳香烃形成的具有两个连接点位的基团，该基团可以是未取代的或者是取代的。
术语“亚杂芳基”是指由具有至少一个杂原子的芳基衍生的具有两个连接点位的基团，该基团可以是未取代的或者是取代的。
术语“亚芳基亚烷基”是指具有芳基和烷基的基团，它在烷基上具有一个连接点位，在芳基上具有一个连接点位。
术语“杂亚芳基亚烷基”是指具有芳基和烷基的基团，它在芳基上具有一个连接点位，在烷基上具有一个连接点位，并至少具有一个杂原子。
除非另有说明，否则所有基团均可以是未取代的或者是取代的。短语“相邻”在用于限定一个器件中的层时并不一定指一层与另一层紧邻。另一方面，短语“相邻的R基团”是指在一个化学通式中相互邻近的多个R基团(即多个R基团位于通过化学键连接的原子上)。
术语“化合物”是指由分子形成的不带电物质，所述分子由原子组成，所述原子不能通过物理方法分离。
术语“配位体”是指附着在金属离子配位层上的分子、离子或原子。
术语“配合物”作为名词时是指具有至少一个金属离子和至少一个配位体的化合物。另外，在本文中使用IUPAC编号系统，其中周期表的族由左至右编号为1-18(CRC化学物理手册，第81版，2000)。
除非另有说明，否则本文使用的所有技术和科学术语的含义与本领域普通技术人员通常认知的术语具有相同的含义。除非另有说明，否则附图中的所有字母符号代表具有该原子缩写的原子。尽管在本发明实践或试验中可使用与本文所述的方法和材料相似或等同的方法或材料，但是合适的方法和材料描述如下。本文提到的所有出版物、专利申请、专利和其它参考文献均在此全文引为参考。在发生矛盾时，以本说明书，包括定义为准。另外，所述材料、方法和实施例是说明性的而非限定性的。
由下列详细描述和权利要求书可显示本发明的其它特征和优点。
附图说明
图1显示电荷迁移单体单元的通式I(a)、I(b)、I(c)；
图2显示电荷迁移单体单元的通式II(a)-II(c)；
图3显示电荷迁移单体单元的通式III(a)、III(b)、III(c)、III(d)；
图4显示本发明聚合物电荷迁移组分的式IV(a)-IV(f)；
图5是发光二极管(LED)的示意图；
图6是场致发光铱配合物的式V(a)-V(e)。
较好实例的详细描述
本发明聚合物组分用作电荷迁移物质。它们可单独使用或者与其它材料组合使用。它们可以用作光活性材料的基质材料(host)。
带有式I(a)-I(c)的三芳基甲烷衍生物单体单元的聚合物特别适合作为空穴迁移材料。
一般来说，n是整数。在一个实例中，n是1-20的整数。在一个实例中，n是1-12的整数。
在一个实例中，Ar1选自苯基和联苯基，其中的一个或多个碳原子可被杂原子所取代。所有这些基团均可被进一步取代。取代基的例子包括，但不限于烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、CnHaFb和C6HcFd，其中，a-d和n如上限定。
在一个实例中，Ar2选自亚苯基和亚苯基亚烷基，它可以被进一步取代。
在一个实例中，N(R1)2是稠合的杂环基团。这种基团的例子包括，但不限于咔唑、苯并二唑和苯并三唑。
在一个实例中，R1选自具有1-12个碳原子的烷基、苯基和苄基。
具有式II(a)-II(c)的菲咯啉衍生物单体单元的聚合物特别适合作为电子迁移材料和抗淬灭材料。
在一个实例中，R2选自苯基、联苯基、吡啶基和联吡啶基，它可被进一步取代。取代基的例子包括，但不限于烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、F、CnHdFb、OCnHaFb、C6HcFd和OC6HcFd，其中，a-d和n如上限定。
在一个实例中，至少一个R2选自苯基和联苯基，它可被一个选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的基团取代，其中，a-d和n如上限定。
在一个实例中，R3选自具有1-12个碳原子的烷基。
在一个实例中，R4选自亚苯基、亚苯基亚烷基、亚烷基和亚烯基。
在一个实例中，芳环上至少具有一个选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的取代基，其中，a-d和n如上限定。
一般来说，n是整数。在一个实例中，n是1-20的整数。在一个实例中，n是1-12的整数。
具有式III(a)、III(b)、III(c)和III(d)的喹啉衍生物单体单元并且是非均聚物的聚合物尤其适合作为电子迁移材料和抗淬灭材料。
一般来说，n是整数。在一个实例中，n是1-20的整数。在一个实例中，n是1-12的整数。
在一个实例中，R4选自亚苯基、亚苯基亚烷基、亚烷基和亚烯基。
在一个实例中，R5选自苯基烯基和苯基炔基，它们可进一步被取代。
在一个实例中，R5选自乙酸烷酯基和芳基羰基，它们可进一步被取代。
在一个实例中，R5选自具有1-12个碳原子的烷基。
在一个实例中，R5选自苯基、取代的苯基吡啶基和取代的吡啶基。所述取代基可选自F、Cl、Br、羟基、羧基、羰基、甲硅烷基、甲硅烷氧基、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
在一个实例中，两个相邻的R5一起形成亚联芳基，它可以进一步被取代。在一个实例中，所述亚联芳基选自亚联苯基和亚联吡啶基。所述取代基可选自F、Cl、Br、羟基、羧基、羰基、甲硅烷基、甲硅烷氧基、烷基、杂烷基、烯基、炔基、芳基、杂芳基、亚烷基芳基、烯基芳基、炔基芳基、亚烷基杂芳基、烯基杂芳基、炔基杂芳基、CnHdFb、OCnHaFb、C6HcFd和OC6HcFd。
在聚合物结构中还可同时使用空穴迁移单体单元和电子迁移单体单元。在一个实例中，混合的电荷迁移材料包括含有至少一种图1所示的式I(a)-I(c)的第一单体单元和至少一种图2所示的式II(a)-II(c)以及图3所示的式III(a)、III(b)、III(c)和III(d)的第二单体单元的聚合物。
所述空穴和电子迁移单体单元可以与同样的单体单元聚合成均聚物。也可与一种或多种不同的单体单元聚合成共聚物。空穴和电子迁移单体单元可相互共聚或者与其它单体单元(例如三芳基胺、芴、亚苯基、亚苯基亚乙烯基、噁二唑、噻二唑、三唑、咔唑等)共聚。低聚的或共聚的空穴迁移和电子迁移材料的例子包括，但不限于图4式IV(a)-IV(f)聚合物，其中，
s和t可相同或不同，为1或更大的整数。
所述聚合物可采用已知的如实施例所述的合成技术(例如Suzuki或Yamamoto偶联反应)制得。
可采用蒸发技术或常规的溶液加工方法将本发明化合物施涂成膜。在本文中，术语“溶液加工”是指由液体介质成膜。所述液体介质可以是溶液、分散液、乳液或其它形式。典型的溶液加工技术包括，例如溶液流延、下滴流延、帘流流延、旋转涂覆、网印、喷墨印刷、凹槽辊印刷等。
电子器件
本发明还涉及一种电子器件，它包括放在其光活性层和一个电极之间的至少一种本发明电荷迁移组分。一种典型的电子器件结构如图5所示。电子器件100具有阳极层110和阴极层160。与阳极层相邻的是包括空穴迁移材料的层120。与阴极层相邻的是包括电子迁移和/或抗淬灭材料的层140。在迁移空穴迁移层和电子迁移/抗淬灭层之间的是光活性层130。在靠近阴极处所述器件还通常任选地使用另一层电子迁移层150。层120、130、140和150可各自和共同地被称为活性层。
根据器件100的用途，所述光活性层130可以是通过施加电压激活的发光层(例如在发光二极管或发光电化学电池中的发光层)，通过施加或不施加偏压响应辐射能并产生信号的材料(例如光探测器)。光探测器的例子包括光导电池、光敏电阻、光开关、光晶体管和光电管，以及光伏电池(参见Markus，John，Electronics and Nucleonics Directionary，470和476(McGraw-Hill，Inc.1966))。
所述器件上的各层可以使用已知适合这些层的任何材料制得。阳极110是对注入正电荷载荷子特别有效的电极。它可以由例如含金属、混合金属、合金、金属氧化物或混合金属氧化物的材料制得，或它可以是导电聚合物，或它们的混合物。合适的金属包括第11族的金属、第4、5、6族的金属和第8-10族的过渡金属。如果要求阳极是透光的，则一般使用第12、13和14族的混合金属氧化物，例如氧化铟锡。阳极110还可包括有机材料，例如聚苯胺(参见“Flexiblelight-emitting diodes made from soluble conducting polymer”，Nature Vol.357，pp477-479(1992年6月11日))。阳极和阴极中应至少有一个是至少部分透明的，以观察产生的光线。
本发明式I(a)-I(c)的三芳基甲烷衍生物的聚合物特别适合在层120中作为迁移空穴的组分。
适合作为层120的其它空穴迁移材料的例子概述在例如Y.Wang的Kirk-Othmer Encyclopedia of Chemical Technology，第4版，18卷，p837-860，1996。可同时使用空穴迁移分子和聚合物。常用的空穴迁移分子有N，N’-二苯基-N，N’-二(3-甲基苯基)-[1，1’-联苯基]-4，4’-二胺(TPD)、1，1-二[(二-4-甲苯基氨基)苯基]环己烷(TAPC)、N，N’-二(4-甲基苯基)-N，N’-二(4-乙基苯基)-[1，1’-(3，3’-二甲基)联苯基]-4，4’-二胺(ETPD)、四(3-甲基苯基)-N，N，N’，N’-2，5-苯二胺(PDA)、α-苯基-4-N，N-二苯基氨基苯乙烯(TPS)、对-(二乙基氨基)苯甲醛二苯基腙(DEH)、三苯胺(TPA)、二[4-(N，N-二乙基氨基)-2-甲基苯基](4-甲基苯基)甲烷(MPMP)、1-苯基-3-[对(二乙基氨基)苯乙烯基]-5-[对(二乙基氨基)苯基]二氢吡唑(PPR或DEASP)、1，2-反式二(9H-咔唑-9-基)环丁烷(DCZB)、N，N，N’，N’-四(4-甲基苯基)-(1，1’-联苯基)-4，4’-二胺(TTB)以及卟啉化合物，例如酞菁铜。常用的空穴迁移聚合物是聚乙烯基咔唑、(苯基甲基)聚硅烷和聚苯胺及其混合物。还可通过将例如上述的空穴迁移分子掺杂至聚合物(例如聚苯乙烯和聚碳酸酯)中制得空穴迁移聚合物。
光活性层130的例子包括所有已知的场致发光材料。较好是有机金属场致发光化合物。最好的化合物包括环金属化的铱和铂场致发光化合物及其混合物。铱与苯基吡啶、苯基喹啉或苯基嘧啶配体的配合物公开在Petrov等的PCT公开申请WO 02/02714中作为场致发光化合物。其它有机金属配合物可参见例如US2001/0019782、EP 1191612、WO02/15645和EP 1191614。带有掺杂铱的金属配合物的聚乙烯基咔唑(PVK)活性层的场致发光器件可参见Burrows和Thompson的PCT WO 00/70655和WO 01/41512。包括电荷载带基质材料和磷光铂配合物的场致发光发射层可参见Thompson等的US 6,303,238、Bradley等的Synth.Met.(2001)，116(1-3)，379-383和Campbell等的Phys.Rev.B.Vol.65085210。几种合适的铱配合物的例子可参见图6的式V(a)-V(f)。也可使用类似的四配合的铂配合物。这些场致发光配合物可以单独使用或者如上所述掺杂在电荷迁移基质材料中。本发明聚合物电荷迁移材料可作为有机金属和其它发射体的基质材料。
本发明菲咯啉衍生物和喹啉衍生物的聚合物(式II(a)-II(c)、III(a)-III(d))特别适合在层140中作为电子迁移/抗淬灭组分，或者在层150中作为电子迁移组分。较好的是，本发明菲咯啉衍生物和喹啉衍生物的聚合物在发光二极管中用作电子迁移/抗淬灭层。
可用于层150的其它电子迁移材料的例子包括金属鳌合的8-羟基喹啉化合物，例如三(8-羟基喹啉)合铝(Alq3)，和唑(azole)化合物，例如2-(4-联苯基)-5-(4-叔丁基苯基)-1，3，4-噁二唑(PBD)和3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1，2，4-三唑(TAZ)及其混合物。
阴极160是对于注入电子或负载荷子特别有效的电极。阴极可以是功函低于阳极的任何金属或非金属。阴极材料可选自第一族碱金属(例如Li、Cs)、第二族金属(碱土金属)、第12族金属，包括稀土元素和镧系和锕系元素。可使用例如铝、铟、钙、钡、钐和镁及其混合材料。还可将含锂有机金属化合物、LiF、Li2O沉积在有机层和阴极层之间以降低运行电压。
在有机电子器件中已知还有其它层。例如，在阳极110和空穴迁移层120之间还可具有一层(未显示)用于促进正电荷迁移和/或层间带隙匹配，或者作为保护层的层。可使用本领域已知的层。另外，上述各层可以由两层或多层组成。或者，可对阳极层110、空穴迁移层120、电子迁移层140和150以及阴极层160中的一部分或全部进行表面处理以提高载荷子迁移效率。各组分层材料的选择较好兼顾提供高效器件的目的和合适的器件寿命。
可以理解各功能层可由多于一层的层形成。
所述器件可由多种技术制得，包括将各层依次蒸气沉积在合适的基片上。可使用的基片有例如玻璃和聚合物膜。可使用常规的蒸气沉积技术，例如热蒸发、化学气相沉积等。或者，可使用任何常规的涂覆技术，包括但不限于旋转涂覆、蘸涂、辊对辊技术、喷墨打印、网印和凹槽辊印刷由合适的溶剂液体加工有机层。一般来说，各层可具有下列厚度范围：阳极110：500-5000
Figure C03816185D0014100638QIETU
，较好1000-2000
Figure C03816185D0014100638QIETU
；空穴迁移层120：50-2000
Figure C03816185D0014100638QIETU
，较好200-1000
Figure C03816185D0014100638QIETU
；光活性层130：10-2000
Figure C03816185D0014100638QIETU
，较好100-1000
Figure C03816185D0014100638QIETU
；电子迁移层140和150：50-2000
Figure C03816185D0014100638QIETU
，较好100-1000
Figure C03816185D0014100638QIETU
；阴极160：200-10000
Figure C03816185D0014100638QIETU
，较好300-5000
Figure C03816185D0014100638QIETU
。各层的相对厚度可影响器件中的电子-空穴结合区的位置，从而影响器件的发射光谱。因此应选择电子迁移层的厚度使得电子-空穴结合区在发光层中。所需的层厚比例将取决于所用材料的实际性能。
本发明三芳基甲烷、菲咯啉衍生物和喹啉衍生物的聚合物可用于除有机发光二极管以外的用途。例如，这些组分可用于光伏器件中用于太阳能转换。还可用于场效应晶体管用于智能卡和薄膜晶体管(TFT)显示驱动器用途。
实施例
下列实施例说明本发明的一些特征和优点。它们用于说明而非限定本发明。除非另有说明，否则所有的百分数均是重量百分数。
实施例1
本实施例说明制造图4所示的聚合物IV(c)。
Figure C03816185D00151
在氮气氛中向1a(3.96g，9mmol)、1b(3.63g，9mmol)、锌(4.0g，61.2mmol)、NiCl2(0.234g，1.80mmol)、PPh3(1.87g，7.2mmol)和联吡啶(0.29g，1.8mmol)的混合物中加入DMF(100ml)。形成的混合物在90℃加热48小时。将其冷却至室温并用CH2Cl2稀释。过滤后，用CH2Cl2洗涤固体，用1N HCl和盐水洗涤合并的有机层。浓缩该溶液并用甲醇沉淀，得到聚合物IV(c)。
实施例2
本实施例说明制备图4所示的聚合物IV(a)。
按与聚合物IV(c)相似的聚合方法制备聚合物IV(a)。
Figure C03816185D00161
实施例3
本实施例说明制备图4所示的聚合物IV(d)。
按与聚合物IV(c)相似的聚合方法制备聚合物IV(d)。
Figure C03816185D00162
实施例4
本实施例说明制备图4所示的聚合物IV(f)。
Figure C03816185D00171
向置于氮气氛中装有Dean-Stark分水器的圆底烧瓶中加入4a(5mmol，根据J.P.Chen等的Synthetic Metals 2003，132，173所述方法合成)、苯甲醛4b(5mmol)、对甲苯磺酸(9.5mmol)和氯苯(20ml)。将形成的混合物回流三天，通过甲醇沉淀分离聚合物。
实施例5
本实施例说明制备图4所示的聚合物IV(e)。
Figure C03816185D00181
在惰性氮气氛中，向圆底烧瓶中加入5a(0.5mol)、5b(0.5mol)、Pd(PAc)2(0.05mol)、P(oTol)3(0.15mol)、Et3N和DMF。将形成的混合物回流三天，用CH2Cl2稀释并用甲醇沉淀而分离产物。

Claims (5)

1.一种组合物，它包括含有至少一种选自下式II(a)的第一单体单元的聚合物，
Figure C03816185C00021
其中：
R2和R3相同或不同，各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd；
R4相同或不同，各自选自亚烷基、亚杂烷基、亚烯基、亚芳基、亚杂芳基；
a、b、c和d为0或整数，使得a+b＝2n+1，c+d＝5；
n是整数；
x是0、1或2；
y是0或1-3的整数；
条件是在芳环上具有至少一个选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的取代基。
2.一种组合物，它包括含有至少一种选自下式II(b)的第一单体单元的聚合物，
Figure C03816185C00022
其中：
R2和R3相同或不同，各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd；
R4相同或不同，各自选自亚烷基、亚杂烷基、亚烯基、亚芳基、亚杂芳基；
a、b、c和d为0或整数，使得a+b＝2n+1，c+d＝5；
n是整数；
x是0、1或2；
y是0或1-3的整数；
条件是在芳环上具有至少一个选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的取代基。
3.一种组合物，它包括含有至少一种选自下式II(c)的第一单体单元的聚合物，
其中：
R2和R3相同或不同，各自选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd；
R4相同或不同，各自选自亚烷基、亚杂烷基、亚烯基、亚芳基、亚杂芳基；
a、b、c和d为0或整数，使得a+b＝2n+1，c+d＝5；
n是整数；
p是0或1；
y是0或1-3的整数；
条件是在芳环上具有至少一个选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的取代基。
4.如权利要求1-3中任一项所述的组合物，其特征在于R2选自苯基、联苯基、吡啶基、联吡啶基或者上述基团各自被至少一个选自下列的取代基所取代后形成的基团：F、CnHaFb、OCnHaFb、C6HcFd或者OC6HcFd，其中，n是1-20的整数；a、b、c和d为0或一个整数，使得a+b＝2n+1，c+d＝5。
5.如权利要求1-3中任一项所述的组合物，其特征在于R4选自亚苯基、亚苯基亚烷基、亚烷基和亚烯基。
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KR100481315B1 (ko) * 2002-02-27 2005-04-07 이석현 유기 광굴절 물질에 사용되는 정공 수송능이 있는자기배열 중합체 및 이를 포함하는 광굴절 혼합물
JP3723140B2 (ja) * 2002-03-04 2005-12-07 Ｎｅｃトーキン株式会社 キノキサリン系化合物を用いた蓄電素子
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