CN1726603B - 喹喔啉衍生物的电荷迁移组合物和由其制得的电子器件 - Google Patents
喹喔啉衍生物的电荷迁移组合物和由其制得的电子器件 Download PDFInfo
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- CN1726603B CN1726603B CN038164671A CN03816467A CN1726603B CN 1726603 B CN1726603 B CN 1726603B CN 038164671 A CN038164671 A CN 038164671A CN 03816467 A CN03816467 A CN 03816467A CN 1726603 B CN1726603 B CN 1726603B
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Images
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Abstract
本发明涉及一种含有式I、II或III的喹喔啉衍生物的电荷迁移组合物。本发明还涉及电子器件,其中有至少一个活性层包括这种电荷迁移组合物。
Description
发明背景
相关申请的交叉引用
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
本发明涉及电荷迁移组合物(composition)。本发明还涉及光活性电子器件,其中有至少一层活性层含有这种电荷迁移组合物。
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,通过向两层透光电气接触层施加电压,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的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。在光活性器件中,一层电子迁移层可位于光活性层(如有机金属发光材料)和电子注入接触层(也称为阴极(cathode))之间。
存在对电荷迁移物质和抗淬灭物质的持续需求。
发明内容
本发明涉及一种电荷迁移组合物,它是喹喔啉衍生物。该喹喔啉衍生物具有示于图1的式I,其中:
R1和R2在各种情况下可相同或不同,并且选自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R2一起构成亚芳基或亚杂芳基;
a、b、c、和d是0或整数,使得a+b=2n+1,并且c+d=5;
n是1-12的整数;和
z是0或1-4的整数。
在另一实例中,本发明涉及一种具有示于图2的式II的电荷迁移组合物,其中:
R1、R2、a至d、和n的定义如上;
R3在各种情况下可相同或不同,并且选自单键或选自以下的基团:亚烷基、亚杂烷基、亚芳基、亚杂芳基、亚芳基亚烷基、和杂亚芳基亚烷基;亚炔基、亚炔基亚芳基、亚炔基杂亚芳基。
Q选自单键和多价基团;
m是大于等于2的整数;
p是0或1和
x是0或1-3的整数。
在另一实例中,本发明涉及一种具有示于图3的式III的电荷迁移组合物,其中:
R1、R2、a至d、n和z的定义如上;
R3在各种情况下可相同或不同,并且选自单键或选自以下的基团:亚烷基、亚杂烷基、亚芳基、亚杂芳基、亚芳基亚烷基、和杂亚芳基亚烷基;亚炔基、亚炔基亚芳基、亚炔基杂亚芳基。
Q选自单键和多价基团;
m是大于等于2的整数;
p是0或1。
在另一实例中,本发明涉及一种电子器件,它具有至少一个活性层,该活性层含有选自示于图1-3中的式I、II和III的材料,式中Ar1、R1至R3,Q、a至d、m、n、p、x和z的定义如上。
如本文所用,术语“电荷迁移组合物”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、延缓或者减少从光活性 层激发态向相邻层的能量迁移和电子迁移,或反之。
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并具有一个连接点位的、由脂肪烃衍生的基团,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“芳基”是指具有一个连接点位的、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(arylalkylene)”是指具有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”是指具有两个连接点位的、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“亚杂芳基”是指由具有至少一个杂原子的且具有两个连接点位的、由芳基衍生的基团,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且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且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(即位于通过化学键连接的原子上的多个R基团)。
术语“化合物”是指由分子形成的不带电物质,所述分子进一步由原子组成,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。术语“聚合物(的)”包括寡聚物种类,并且包括具有2个或多个单体单元的材料。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、方法和实施例仅仅是说明性的而非限定性。
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显示了本发明电荷迁移组合物的式I。
图2显示了本发明电荷迁移组合物的式II。
图3显示了本发明电荷迁移组合物的式III。
图4显示了本发明电荷迁移组合物的式I(a)至I(ag)。
图5显示了用于多配位(multidentate)连接基团的式IV(a)至IV(h)。
图6显示了本发明电荷迁移组合物的式II(a)至II(I)。
图7显示了场致发光铱配合物的式V(a)至V(e)。
图8是发光二极管(LED)的示意图。
图9是LED测试装置的示意图。
图10显示了已知的电子迁移组合物的结构式。
具体实施方式
由示于图1的式I所表示的喹喔啉衍生化合物,具有作为电子转移组合物和作为抗淬灭剂的特殊用途。该喹喔啉化合物还可用作发光材料的基质(host)。
通常,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,R1选自苯基烯基和苯基炔基,它们可被进一步取代。
在一个实例中,R1选自烷基乙酸基(alkylacetate)和芳基羰基,它们可被进一步取代。
在一个实例中,R1选自具有1-12个碳原子的烷基。
在一个实例中,R2选自苯基、取代的苯基、吡啶基、和取代的吡啶基。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R2一起构成亚联芳基(biarylene),它可进一步被取代。在一个实例中,该亚联芳基选自亚联苯基和亚联吡啶基。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。
合适的这种类型电子迁移/抗淬灭(ET/AQ)化合物的例子包括(但并不限于)在图4中给出的式I(a)至I(ag)。
式I表示的物质可用常规的有机合成技术制备,如实施例中所阐述的那样。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。如本文所用,术语“溶液加工”是指由液体介质形成膜。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。
在某些情况下,需要增加化合物的Tg,以便提高稳定性、可涂覆性或其他性能。这可以通过将两个或多个化合物通过连接基团连接在一起,从而形成示于图2的式II或图3中的式III化合物而实现。在这些结构式中,Q是单键或多价连接基团,它具有两个或多个连接点位。多价连接基团可以是具有两个或多个连接点位的烃基,并且可以是脂族或芳族的。多价连接基团可以是亚杂烷基或亚杂芳基,其中杂原子可以是,例如N、O、S或Si。多价基团Q的例子包括(但并不限于):亚烷基、亚烯基和亚炔基,和具有杂原子的类似化合物;单环、多环和稠环的芳族基团和杂芳族基团;芳基胺如三芳基胺;硅烷和硅氧烷。多价Q基团的其他例子,在示于图5中的式V(a)至V(h)中给出。在式IV(f)中,任一碳原子可以连于电荷迁移部分。在式IV(h)中,任一Si原子可以连于电荷迁移部分。还可以使用诸如Ge和Sn之类的杂原子。连接基团还可以是-[SiMeR1-SiMeR1]n-,式中R1和n如上定义。
通常,m是大于等于2的整数。确切的数目取决于Q上可供连接的位置数目以及在喹喔啉部分和Q部分的几何结构。在一个实例中,m是2-10的整数。
在一个实例中,在式II中,R1选自苯基和取代的苯基。取代基可选自:F、Cl、Br、烷基、杂烷基、烯基、和炔基。
在一个实例中,在式II中,R1选自烷基乙酸基和芳基羰基,它们可被进一步取代。
在一个实例中,在式II中,R1选自具有1-12个碳原子的烷基。
在一个实例中,在式II中,R2选自苯基、取代的苯基、吡啶基、和取代的吡啶基。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,在式II中,两个R2一起构成亚联芳基(biarylene),它可进一步被取代。在一个实例中,该亚联芳基选自亚联苯基和亚联吡啶基。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,在式II中,x是0。
在一个实例中,在式II中,R3选自芳基、杂芳基、烷基和杂烷基。在一个实例中,在式II中,R3选自苯基和取代的苯基。在一个实例中,在式II中,R3 选自具有1-12个碳原子的烷基和杂烷基,它可进一步被取代。
在一个实例中,在式III中,R1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,在式III中,R1选自烷基乙酸基和芳基羰基,它们可被进一步取代。
在一个实例中,在式III中,R1选自具有1-12个碳原子的烷基。
在一个实例中,在式III中,R2是H。
在一个实例中,在式III中,R3选自芳基、杂芳基、烷基和杂烷基。在一个实例中,在式III中,R3选自苯基和取代的苯基。在一个实例中,在式III中,R3 选自具有1-12个碳原子的烷基和杂烷基,它们可进一步被取代。
式II所表示的连接型化合物的具体例子,在图6中的式II(a)至II(I)中给出。
电子器件
本发明还涉及一种电子器件,它包括放置在光活性层和一个电极之间的至少一种本发明的电荷迁移组合物。一种典型的电子器件结构如图8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含空穴迁移材料的层120。与阴极层相邻的是包含电子迁移和/或抗淬灭材料(“ET/AQ”)的层140。在空穴迁移层和电子迁移和/或抗淬灭层之间的是光活性层130。作为一种任选方式,所述器件还通常在靠近阴极处使用另一层电子迁移层150。层120、130、140和150可单独地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而激活的发光层(例如在发光二极管或发光电化学电池中),在施加或不施加偏压下响应辐射能并产生信号的材料层(例如在光探测中)。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(这些术语的描述可参见Markus,John,Electronics and Nucleonics Dictionary,470和476(McGraw-Hill,Inc.1966))。
本发明喹喔啉衍生化合物特别适合用作层140中的电子转移和/或抗淬灭组合物,或者作为层150中的电子转移组合物。例如,在一个实例中,本发明的喹喔啉衍生化合物可用作发光二极管中的电子迁移和/或抗淬灭层。
还应理解,ET/AQ材料必须与所用的光活性材料在化学上是相容的。例如,当沉积在光活性材料层上时,ET/AQ材料必须形成光滑膜。如果发生团聚,器 件的性能将下降。
器件中的其他各层可使用已知适用于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,或是它们的混合物。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(如“Flexiblelight-emitting diodes made from soluble conducting polymer”,Nature Vol.357,pp477-479(1992年6月11日)中所述)。阳极和阴极中至少有一个应是至少部分透明的,以便观察到所产生的光线。
适合用作层120的空穴迁移材料的例子概述在例如Y.Wang的Kirk-OthmerEncyclopedia ofChemical 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,从而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。有机金属场致发光化合物是优选的。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位体的配合物,已作为场致发光化合物而公开于Petrov等的PCT公开申请WO 02/02714。其它的有机金属配合物描述于例如出版的申请US 2001/0019782、EP 1191612、WO02/15645和EP1191614。带有掺杂铱金属配合物的聚乙烯基咔唑(PVK)活性层的场致发光器件,已由Burrows和Thompson描述于出版的PCT申请WO 00/70655和WO01/41512。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,已由 Thompson等描述于US专利6,303,238,Bradley等人描述于Synth.Met.(2001),116(1-3),379-383和Campbell等人描述于Phys.Rev.B.Vol.65 085210。作为几种合适的铱配合物的例子在图7中的式VI(a)-VI(e)中给出。也可使用类似的四配位的铂配合物。如上所述,这些场致发光配合物可以单独使用,或者掺杂在荷电(charge-carrying)基质材料中。本发明的喹喔啉材料还可用作发射层中荷电基质。
阴极160是对于注入电子或负载荷子特别有效的电极。阴极可以是功函数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。还可将含锂的有机金属化合物、LiF和Li2O可沉积在有机层和阴极层之间以降低工作电压。
已知在有机电子器件中可有其它层。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/或层间带隙的匹配,或者作为保护层。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,以提高载荷子的迁移效率。各组分层材料的选择,宜兼顾提供高效器件和提供合适的器件工作寿命的目的。
可以理解各功能层可由多于一层的层所形成。
所述器件可由各种不同技术制得,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或印刷技术,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,用合适的溶剂中的溶液或分散液涂覆形成有机层。一般来说,各层可具有下列厚度范围:阳极110:500-5000_,较好1000-2000_;空穴迁移层120:50-2000_,较好200-1000_;光活性层130:10-2000_,较好100-1000_;电子迁移层140和150:50-2000_,较好100-1000_;阴极160:200-10000_,较好300-5000_。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。
本发明的喹喔啉衍生化合物可用于除有机发光二极管(OLED)以外的用途。例如,这些组合物可用于进行太阳能转换的光伏器件。还可用在场效应晶体管中,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1-16
这些实施例阐述了喹喔啉衍生物ET/AQ组合物的制备。
实施例1
该实施例阐述了图4中化合物I(n)的制备。
在烘干的可再密封的Schlenk烧瓶中,装入2,3-(二-4-氟苯基)-6-溴喹喔啉(2.00g,5.00mmol),对-叔丁基苯乙烯(1.02g,6.40mmol),Na2CO3(0.68g,6.40mmol),反式-二(μ-乙酸根合)二[o-(二-邻-甲苯基-膦基)苄基]二钯(II)(trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium)(0.020g,0.02mmol)和2,6-二-叔丁基-对甲苯酚(0.552g,2.50mmol)和N,N-二甲基乙酰胺(12mL)。Schlenk烧瓶用Teflon阀密封,然后将混合物在130℃加热21小时。形成的混合物冷却至室温,稀释于Et2O(230mL)中,然后通过二氧化硅垫进行过滤。滤液用水(2×100mL)和盐水(1×50mL)洗涤。有机层被干燥并浓缩,得到粗产物,然后通过快速色谱法进行纯化,得到纯化的产物,为浅黄色固体,产率为72%(1.71g)。 19F NMR(376.8Hz,CD2Cl2):δ-113.48和-113.58。
实施例2
该实施例阐述了图4中化合物I(o)的制备。
在烘干的可再密封的Schlenk烧瓶中,装入4-氟苯基乙炔(0.334g,2.78mmol)、2,3-(二-4-氟苯基)-6-溴喹喔啉(1.00g,2.53mmol),Pd2(dba)3(0.046g,0.05mmol)、三苯基膦(0.066g,0.253mmol),CuI(0.010g,0.05mmol)和三乙胺(15mL)。然后密封烧瓶并在60℃加热24小时。形成的混合物用二氯甲烷稀释,用水和盐水洗涤,用硫酸镁干燥,过滤和浓缩,得到米色固体。粗产物通过用己烷(3×20mL)重复洗涤而纯化,得到0.924g(84%产率)。1H NMR(CD2Cl2,500MHz)δ8.37(d,1H,J=1.6),8.20-8.18(d,1H,8.8),7.98-7.95(dd,1H,J=8.3,1.5),7.74-7.70(dd,2H,J=5.4,3.6),7.64-7.60(m,4H),7.24-7.14(m,6H)。19F NMR(CD2Cl2,500MHz)δ-111.14(m,1F),-113.1(m,2F)。
实施例3
该实施例阐述了图4中化合物I(q)的制备。
在反应器中装入来自实施例1的化合物I(n)(1.70g,3.55mmol),ESCAT 140Pd/C催化剂(0.056g)和MeOH(45mL)。反应混合物用氮气吹洗,加压至500psigH2然后加热至60℃8小时。真空去除挥发物,然后产物通过快速色谱法(5%EtOAc/己烷,其中“Et”表示乙基,而“OAc”表示乙酸根)纯化,得到浅黄色粉末(0.220g,13%)。19F NMR(376.8Hz,CD2Cl2):δ-111.14和-114.60。
实施例4
该实施例阐述了图4中化合物I(b)的制备。
将3,4-二氨基甲苯(28.78g,0.236mol)和苯偶酰(45g,0.214mol)的混合物,在738mL氯仿中与2.16mL三氟乙酸一起回流3小时。混合物用10%HCl、盐水洗涤三次,然后用硫酸镁干燥,过滤,再通过二氧化硅床真空过滤。得到的溶液被蒸干。从550毫升甲醇中重结晶出69克粗产物。过滤的固体在真空炉中于50℃干燥1小时,得到55.56g干燥固体,产率为78.8%。
实施例5
该实施例阐述了图4中化合物I(e)的制备。
将3,4-二氨基甲苯(4.49g,0.037mol)和4,4′-二甲氧基苯偶酰(9.46g,0.035mol)的混合物,在125mL氯仿中与0.35mL三氟乙酸回流6小时。混合物用水洗涤2次,用硫酸镁干燥,并蒸干至约11g。将固体溶解于1∶1的乙酸乙酯∶氯仿中进行快速色谱,然后用乙酸乙酯洗脱。蒸干后得到9.7克暗色固体,产率72%。
实施例6
该实施例阐述了图4中化合物I(c)的制备。
将3,4-二氨基甲苯(0.603g,4.93mmol)和1,10-菲咯啉-5,6-二酮(0.945g,4.50mmol)的混合物,在602mL氯仿中与0.35mL三氟乙酸一起回流6小时。该混合物趁热用中孔烧结玻璃过滤器(medium frit)进行过滤,在干燥后得到0.85g浅黄色固体。产率63%。
在冷却后,从母液获得第二批收获产物,即得到额外的0.31克。
实施例7
该实施例阐述了图4中化合物I(d)的制备。
将3,4-二氨基甲苯(5.36g,44mmol)和菲醌(8.33g,0.040mol)的混合物,在119mL氯仿中与0.4mL三氟乙酸一起回流6小时。混合物通过中孔烧结玻璃过滤器过滤,然后从430g甲基乙基酮中重结晶,得到5.5g毛茸茸样的黄色产物。产率46%。
实施例8
该实施例阐述了图4中化合物I(f)的制备。
将3,4-二氨基甲苯(5.36g,44mmol)和2,2′-吡啶偶酰(pyridil)(8.49g,40mmol)的混合物,在119mL氯仿中与0.4mL三氟乙酸一起回流4小时。分离反应混合物,用100mL水洗涤4次,然后蒸干至10.4g。获得的固体溶解于1∶1的乙酸乙酯∶氯仿中进行快速色谱,并用乙酸乙酯洗脱。蒸发获得9.3g固体。
实施例9
该实施例阐述了图4中化合物I(g)的制备。
将3,4-二氨基苯甲酸甲酯(7.28g,44mmol)和苯偶酰(8.41g,40mmol)的混合物,在140ml二氯甲烷中回流21小时。将反应混合物蒸干,然后回流溶解于520mL甲醇和150mL二氯甲烷。该溶液然后被部分蒸发,从而选择性地结晶出所需产物。
实施例10
该实施例阐述了图4中化合物I(k)的制备。
将3,4-二氨基苯甲酸甲酯(6.37g,0.038mol)和4,4′-二甲氧基苯偶酰(9.46g,.035mol)的混合物,在142mL二氯甲烷中与3滴三氟乙酸一起回流5小时。加入10.7g N-甲基吡咯烷酮,然后再继续回流26小时。混合物用水洗涤3次,用硫酸镁干燥,过滤,然后通过将有机溶液倾倒入550克甲醇而使产物沉淀。放置过夜后,过滤产物,并在95℃下真空干燥,得到10.39g产物。
实施例11
该实施例阐述了图4中化合物I(r)的制备。
将3,4-二氨基苯甲酸甲酯(6.12g,0.037mol)和菲醌(7.08g,0.034mol)的混合物,在119mL二氯甲烷中回流。加入100g of N-甲基吡咯烷酮,然后对蒸馏去 除氯化溶剂。将器皿加热至150℃,从而获得澄清的溶液,并用气相色谱跟踪反应。通过倒入410g甲醇而使产物沉淀,然后滤掉固体沉淀。产物用甲苯重结晶,然后用1200g甲基乙基酮、150g甲苯和1100g四氢呋喃的混合溶剂再次结晶。得到3.3g of带珠光的金色毛状物质。
实施例12
该实施例阐述了图4中化合物I(1)的制备。
将1,2-苯二胺(13.91g,0.129mol)和4,4′-二溴苯偶酰(45g,0.116mol)的混合物,在558mL氯仿中与1.0ml三氟乙酸一起回流6小时。混合物用10%HCl洗涤3次,并蒸干至约51克。在回流下用600mL乙酸乙酯和100mL甲醇重结晶。过夜形成大晶体,然后过滤,用甲醇洗涤2次,干燥得到29.63g,并且从冷却的母液中获得4.9g的第二批收获产物。
实施例13
该实施例阐述了图4中化合物I(h)的制备。
将2,3-二氨基甲苯(4.84g,0.040mol)和苯偶酰(7.56g,0.036mol)的混合物,在112mL二氯甲烷中回流19小时。混合物用12%HCl洗涤4次,用硫酸镁干燥,过滤并蒸干,得到约9.5g棕色固体。将该固体在回流下溶解于495g甲醇,然后蒸馏去除约300克溶剂。用冰冷却,产生细小晶体。过滤并用甲醇洗涤晶体滤饼。
实施例14
该实施例阐述了图4中化合物I(i)的制备。
将2,3-二氨基甲苯(5.05g,0.041mol)和菲醌(7.84g,0.038mol)的混合物,在112ml氯仿中回流29小时。形成的溶液在二氧化硅柱上用氯仿洗脱剂进行色谱分离。将产物与溶剂蒸发分开,得到约10g,然后进行真空炉干燥。产物是晶体。
实施例15
该实施例阐述了图4中化合物I(j)的制备。
将3,4-二氨基苯甲酸甲酯(7.28g 0.044mol)和2,2′-吡啶偶酰(pyridil)(8.48g,0.040mol)的混合物,在140mL二氯甲烷中回流7小时。蒸干溶液至15.7g,然后 将固体在回流下溶解于240mL二氯甲烷和140mL甲醇中。在加入280mL甲醇和蒸发掉约150mL溶剂后,将溶液放置过夜。收集形成的固体,并干燥得到9.8g。取7.7g该物质,溶解于203g甲醇和50g二氯甲烷中。蒸馏去除50mL以上的溶剂。晶体在过夜后形成。过滤并在真空炉中干燥。
实施例16
该实施例阐述了图4中化合物I(t)的制备。
在烘干的可再密封的Schlenk烧瓶中,装入2,3-(二-4-氟苯基)-6-溴喹喔啉(1.23g,3.08mmol)、1,3-二乙烯基四甲基二硅氧烷(3.40mL,14.8mmol)、KOAc(0.440g,4.48mmol)、Pd(OAc)2(0.012g,0.06mmol)、P(o-Tol)3(0.06g,0.20mmol)、NEt3(0.300mL)、DMF(约2mL)和水(0.45mL)。Sehlenk烧瓶用Teflon阀密封,然后将混合物在95℃加热48小时。形成的混合物冷却至室温,稀释于水(15mL)中,然后产物用二氯甲烷(15毫升)萃取。有机层被干燥和浓缩,得到粗产物。粗产物通过色谱法(3%EtOAc/己烷)进行纯化,得到浅黄色固体(0.478g,31%产率)。19FNMR(376.8Hz,CD2Cl2):δ-113.45(brm)。
实施例17-19
这些实施例阐述了具有一个以上喹喔啉基团的电荷迁移组合物的制备。
实施例17
该实施例阐述了图6中化合物II(e)的制备。
在500mL配有氮气导入管和冷凝器的3颈圆底烧瓶中,装入1,4-苯二硼酸(2g,12.1mmol)、2,3-(二-4-氟苯基)-6-溴喹喔啉(9.54g,24.1mmol)、Pd(PPh3)4(2.78g,2.41mmol)、碳酸钾(6.67g,48.3mmol)、DME(150mL)和水(150mL)。反应混合物回流24小时,之后用水和二氯甲烷稀释。有机层含有沉淀物,将沉淀物通过过滤而分离出,用二氯甲烷洗涤,得到2.75g(32%产率)米色粉末。1H NMR(CD2Cl2,500MHz)δ8.56-8.55(m,2H),8.35-8.33(d,2H),8.29(m,2H),8.12(s,4H),7.68-7.64(m,8H),7.29-7.16(m,8H)。19F NMR(CD2Cl2,500MHz)δ-113.35(m,2F)。
实施例18
该实施例阐述了图6中化合物II(k)的制备。
1,4-二苯偶酰(bisbenzil)(1g,2.92mmol)和4,5-二甲基-1,2-苯二胺(0.769g,5.84mmol)在氯仿(20mL)中的混合物,在氮气气氛下回流15小时。向反应混合物中加入己烷,沉淀出鲜黄色沉淀物,该沉淀物通过过滤而分离出,用己烷洗涤,得到鲜黄色粉末的产物(1.32g,83%产率).1H NMR(CD2Cl2,500MHz)δ7.89-7.88(d,4H,J=7.1Hz),7.50-7.48(dd,4H.,J=1.5Hz,7.7Hz),7.45(s,4H),7.35-7.31(m,10H),2.53(s,12H)。
实施例19
该实施例阐述了图6中化合物II(a)的制备。
将3,3-二氨基联苯胺(0.4580g,2.14mmol)和1,10-菲咯啉-5,6-二酮(0.9458g,4.5mmol)的混合物,在10克N-甲基吡咯烷酮中与0.045ml三氟乙酸一起在85℃加热23小时。在室温下将氯仿加入反应器皿中,然后将内含物用细孔烧结玻璃过滤器(frit)过滤,用丙酮和乙醚洗涤,然后90℃真空干燥。
实施例20
该实施例阐述了图4中化合物I(m)的制备。
该化合物的合成,按照制备I(o)的合成方法进行,得到所需产物,产率58%。 1H NMR(CD2Cl2,500MHz)δ8.38(d,1H,J=1.8Hz),8.20-8.18(d,1H,8.4Hz),7.99-7.97(dd,1H,J=1.8Hz,8.7Hz),7.73-7.71(m,2H),7.64-7.61(m,4H),7.52-7.50(m,3H),7.19-7.14(m,4H)。19F NMR(CD2Cl2,500MHz)δ-113.14(m,2F)。
实施例21
该实施例阐述了图6中化合物II(g)的制备。
该化合物的合成,按照制备II(e)的合成方法进行,得到所需产物,产率13%。 1H NMR(CD2Cl2,500 MHz)δ8.42-8.41(d,2H,J=1.9),8.20-8.18(d,2H,J=8.5),8.13-8.11(dd,2H,J=9.1Hz,2.0Hz),8.00(s,4H),7.54-7.51(dd,8H,J=8.7 Hz,3.1Hz),6.9-6.9(q,8H),5.48(s,12H)。
实施例22
该实施例阐述了图6中化合物II(d)的制备。
该化合物的合成,按照制备II(e)的合成方法进行,得到所需产物,产率10%。 1H NMR(CD2Cl2,500 MHz)δ 8.62-8.61(d,2H,J=1.5),8.44-8.41(m,4H),8.41- 8.39(d,2H,J=9.5 Hz),8.34-8.31(dd,2H,J=8.3 Hz,1.6 Hz),8.14(m,6H),8.12-8.11(m,2H),7.98-7.94(m,4H),7.38-7.34(m,4H)。
实施例23
该实施例阐述了图6中化合物II(k)的制备。
该化合物的合成,按照制备II(j)的合成方法进行,得到所需产物,产率66%。 1H NMR(CD2Cl2,500 MHz)δ8.09-8.06(t,2H,J=7.4 Hz),7.98-7.96(d,2H,J=7.2Hz),7.69-7.67(d,2H,8.9),7.59-7.51(m,10H),7.43-7.40(m,8H),2.67(s,6H)。
实施例24
该实施例阐述了图6中化合物II(i)的制备。
该化合物的合成,按照制备II(j)的合成方法进行,得到所需产物,产率65%。 1H NMR(CD2Cl2,500 MHz)δ8.29-8.24(m,1H),8.07-8.01(m,1H),7.90-7.86(m,1H),7.80-7.78(m,0.6H),7.72-7.66(m,1H),7.64-7.59(m,4H),7.51-7.44(m,3H)。19F NMR(CD2Cl2,500MHz)δ-108.4(m,2F),-108.9(m,3F),-109.2(m,8F),-109.4(m,8F)。
实施例25
该实施例阐述了图4中化合物II(m)的制备。
该化合物的合成,用下列所示的合成路线进行。
化合物II(ma)的获得是所用制备I(o)的合成方法,从而得到所需产物,产率65%。1H NMR(CD2Cl2,500MHz)δ7.64-7.60(m,4H),7.27(s,2H),7.20-7.16(t,4H,J=8.9Hz)。19F NMR(CD2Cl2,500MHz)δ-111.10(m,2F)。在氮气下,在配有冷凝器的3颈圆底烧瓶中,装入化合物II(ma)(2.00g,6.25mmol,0.1当量),Adogen464(0.125g),高锰酸钾(4.9g,31.25mmol,5.00当量),碳酸氢钠(1.05g,12.5mmol,2.0当量),水(80mL)和二氯甲烷(50mL)。将混合物回流36小时。冷却至室温后,将反应混合物中缓慢加入9.3g碳酸氢钠和4mL HCl,以中和和去除过量的氧化剂。反应混合物用二氯甲烷和水稀释,分离各层,并将有机部分用水、盐水洗涤,然后用硫酸镁干燥。产物通过蒸发溶剂而分离,然后用乙醇进行重结晶,得到0.6g(25%产率)II(mb),为黄色针状晶体。1H NMR(CD2Cl2,500MHz):δ8.25-8.21(dd,4H,J=8.9Hz,5.6Hz),7.98(s,2H),7.36-7.32(t,4H,J=8.70Hz)。19F NMR(CD2Cl2,500MHz):δ-101.8(m,2F)。化合物II(m)的合成,按照用于制备II(k)的程序进行,得到所需产物,产率20%。1HNMR(CD2Cl2,500MHz)δ8.25-8.21(m,1H),8.19-8.15(m,1H),7.85-7.78(m,2H),7.73-7.64(m,6H),7.29-7.25(t,4H),6.69-6.66(m,2H)。19F NMR(CD2Cl2 500MHz)δ-108.7,-108.8(m,2F),-112.4(m,1F),-112.6(m,1F)。
电子迁移和/或抗淬灭的组合物的性能总结于下表1。
化合物 | 吸收起始 (nm),E1-E5 | 吸收最大值 (nm) | E1/2 vs SCE(伏) | LUMO vs真 空(eV),E1 |
化合物I(a) | 375 | 345 | -1.5 | -3.33 |
化合物I(b) | 378 | 339 | -1.6 | -3.24 |
化合物I(c) | 400 | 385 | -1.17 | -3.67 |
化合物I(d) | 410 | 397 | -1.3 | -3.54 |
化合物I(g) | 390 | 352 | -1.29 | -3.55 |
化合物II(a) | -- | -- | -- | --该行的目的是什么? |
化合物I(e) | 405 | 369 | -1.66 | -3.18 |
化合物I(f) | 378 | 339 | -1.53 | -3.31 |
化合物I(o) | 420 | 382 | -1.35 | -3.49 |
化合物I(l) | 407 | 394 | -1.28 | -3.56 |
化合物I(k) | 385 | 343 | -1.59 | -3.25 |
化合物I(w) | 417 | 401 | -1.03 | -3.81 |
化合物I(p) | 380 | 347 | -1.49 | -3.35 |
化合物I(x) | 380 | 342 | -1.22 | -3.62 |
对照ADDPA | 368 | 310 | -1.85 | -2.99 |
对照BDPA | 366 | 316 | -1.95 | -2.89 |
实施例27
本实施例说明图7中式V(a)所示的铱场致发光配合物的制备。
苯基吡啶配位体,2-(4-氟苯基)-5-三氟甲基吡啶
使用的通用方法描述于O.Lohse、P.Thevenin、E.Waldvogel的Synlett 1999,45-48中。将200ml经脱气的水、20g碳酸钾、150ml 1,2-二甲氧基乙烷、0.5gPd(PPh3)4、0.05mol 2-氯-5-三氟甲基吡啶和0.05mol 4-氟苯基硼酸的混合物,回流(80-90℃)16-30小时。用300ml水稀释形成的反应混合物,并用二氯甲烷(2×100ml)萃取。合并的有机层用硫酸镁干燥,真空除去溶剂。通过真空分馏纯化液体产物。在己烷中重结晶固态产物。分离材料的纯度大于98%。
铱配合物
在氮气流中边将温度缓慢(30分钟)上升至185℃(油浴),边搅拌IrCl3·nH2O(54%Ir,508mg)、2-(4-氟苯基)-5-三氟甲基吡啶(由上面制得,2.20g)、AgOCOCF3(1.01g)和水(1ml)的混合物。在185-190℃2小时后,该混合物固化。将混合物冷却至室温。用二氯甲烷萃取该固体至萃取液无色。用短二氧化硅柱过滤合并的二氯甲烷溶液并蒸发。向残余物中加入甲醇(50ml)以后,将烧瓶在-10℃保持过夜。分离三环金属化的配合物黄色沉淀(图5中的化合物IVa),用甲醇洗涤,并真空干燥。得到1.07g产物(82%)。通过缓慢冷却其在1,2-二氯乙烷中的热溶液,得到该配合物的X-射线品质的晶体。
实施例28
本实施例说明使用本发明电荷迁移组合物形成有机发光二极管。
用热蒸发技术制得薄膜有机发光二极管器件,它包括空穴迁移层(HT层)、场致发光层(EL层)和至少一层电子迁移和/或抗淬灭层(ET/AQ层)。使用带油扩散泵的Edward Auto 306蒸发机。所有薄膜沉积的基本真空度在10-6乇范围内。沉积室能在不中止真空的情况下沉积5种不同的薄膜。
使用购自Thin Film Devices,Inc.的带图案的氧化铟锡(ITO)涂覆的玻璃基 片。这些ITO是涂覆1400_ ITO涂层的康宁1737玻璃,片电阻为30Ω/平方,透光率80%。随后在洗涤剂水溶液中超声波清洗该带图案的ITO基片。该基片随后用蒸馏水、异丙醇漂清,在甲苯蒸气中脱脂约3小时。
接着将该清洁的带图案ITO基片装入真空室,并将该真空室抽真空至10-6乇。随后用氧等离子体将该基片进一步清洁约5-10分钟。清洁后,通过热沉积将多层薄膜依次沉积在该基片上。最后,通过掩模沉积Al或LiF和Al的带图案的金属电极。在沉积过程中使用石英晶体监测器(Sycon STC-200)测量薄膜的厚度。实施例中所有给出的薄膜厚度均是标称的,假设沉积材料的密度为1而计算得出。随后从真空室中取出完成的有机发光二极管器件,不包装立即鉴定。
表2总结了用本发明的喹喔啉衍生物ET/AQ组合物制得的器件。在所有情况下,阳极是ITO(如上所述),空穴迁移层是MPMP,而发射层是实施例27中制备的铱配合物,它们具有所示的厚度。当存在时,电子迁移层150是具有给定厚度的三(8-羟基喹啉)合铝(III)(Alq)。阴极是具有给定厚度的Al层或LiF/Al双层。
有机发光二极管样品的鉴定是测量其(1)电流-电压(I-V)曲线;(2)场致发光光度与电压的关系;(3)场致发光光谱与电压的关系。使用的设备200如图9所示。使用237、280型Keithley Source-Measurement Unit测量有机发光二极管样品220的I-V曲线。使用Minolta LS-110发光仪210测量场致发光光度(单位cd/m2)与电压的关系,同时使用Keithley SMU扫描电压。场致发光光谱是如下获得的:使用一对透镜230收集光线,使之通过电子快门240,经分光仪250分散,随后用二极管阵列探测器260测量。所有这三组测量均是同时进行的,并由计算机270控制。器件在某一电压下的效率是将LED的场致发光光度除以运行该器件所需的电流密度得到的。单位为cd/A。
使用本发明的喹喔啉ET/AQ组合物的器件结果,列于下表3。
Claims (33)
1.一种式I喹喔啉衍生物:
其中,R1选自氢原子、C1-12烷基、烷基乙酸基、C6HcFd和OCnHaFb;
R2选自H、C6HcFd、OCnHaFb、杂芳基、苯基、亚烷基芳基、烯基芳基、炔基芳基,或者两个R2一起构成亚芳基或亚杂芳基;
a、b、c和d是0或整数,使得a+b=2n+1,并且c+d=5;
n是1-12的整数;和
z是0或1-4的整数。
2.如权利要求1所述的衍生物,其特征在于R1选自C1-12烷基、烷基乙酸基。
3.如权利要求1所述的衍生物,其特征在于R2选自苯基和吡啶基。
4.如权利要求1所述的衍生物,其特征在于两个R2一起构成亚联吡啶基。
6.如权利要求1所述的衍生物,其特征在于,所述的喹喔啉衍生物是:
7.一种喹喔啉衍生物,它具有下列通式:
或者
8.一种式II化合物:
其中,R1是氢原子;
R2选自杂芳基、OCnHaFb、C6HcFd,或者两个R2一起构成亚芳基或亚杂芳基;
R3是单键;
Q选自单键和亚芳基;
a、b、c和d是0或整数,使得a+b=2n+1,并且c+d=5;
m是大于或等于2的整数;
n是1-12的整数;
p是0或1;和
x是0或1-3的整数。
9.如权利要求8所述的化合物,其特征在于,
m是2-10的整数;
Q是单键。
10.如权利要求8所述的化合物,其特征在于Q选自:
和
11.如权利要求8所述的化合物,其特征在于所述R2选自苯基或者吡啶基。
14.如权利要求13所述的化合物,其特征在于R1是具有1-12个碳原子的烷基。
15.如权利要求13所述的化合物,其特征在于R2是氢原子。
17.一种电子器件,它包括一个光活性层和一个第二层,其中至少一层含有式I的喹喔啉衍生物:
其中,R1选自氢原子、C1-12烷基、烷基乙酸基、C6HcFd和OCnHaFb;
R2选自H、C6HcFd、OCnHaFb、杂芳基、苯基、亚烷基芳基、烯基芳基、炔基芳基,或者两个R2一起构成亚芳基或亚杂芳基;
a、b、c和d是0或整数,使得a+b=2n+1,并且c+d=5;
n是1-12的整数;和
z是0或1-4的整数。
18.如权利要求17所述的电子器件,其特征在于R1选自C1-12烷基、烷基乙酸基。
19.如权利要求17所述的电子器件,其特征在于R2选自苯基和吡啶基。
20.如权利要求17所述的电子器件,其特征在于两个R2一起构成亚联吡啶基。
24.一种电子器件,它包括一个光活性层和一个第二层,其中至少一层含有选自下式II的喹喔啉衍生物:
其中,R1是氢原子;
R2选自杂芳基、OCnHaFb、C6HcFd,或者两个R2一起构成亚芳基或亚杂芳基;
R3是单键;
Q选自单键和亚芳基;
a、b、c和d是0或整数,使得a+b=2n+1,并且c+d=5;
m是大于或等于2的整数;
n是1-12的整数;
p是0或1;和
x是0或1-3的整数。
25.如权利要求24所述的电子器件,其特征在于,
m是2-10的整数;
Q是单键。
27.如权利要求24所述的电子器件,其特征在于所述R2选自苯基或者吡啶基。
29.一种电子器件,它包括一个光活性层和一个第二层,其中至少一层含有选自下式III的喹喔啉衍生物:
其中,
R1选自氢原子、C1-12烷基、F、Cl、Br;
R2选自氢、芳基、或者C6HcFd;和
R3是单键;
Q选自芳基或者杂芳基;
a和b是0或者整数,使得a+b=2n+1;
m是2或大于2的整数;
p是0或1;
z是1-4的整数。
30.如权利要求29所述的电子器件,其特征在于R1是具有1-12个碳原子的烷基。
31.如权利要求29所述的电子器件,其特征在于R2是氢原子。
33.如权利要求17-32中任一项所述的电子器件,其特征在于该器件是发光二极管、发光电化学电池或光探测器。
Applications Claiming Priority (5)
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PCT/US2003/021618 WO2004006355A2 (en) | 2002-07-10 | 2003-07-09 | Charge transport compositions which are quinazoline derivatives and electronic devices made with such compositions |
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CNA038164159A Pending CN1668703A (zh) | 2002-07-10 | 2003-07-09 | 基于三芳基甲烷的电荷迁移组合物及其在电子器件中的应用 |
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