CN1668616A - 含氟化的菲咯啉衍生物的电荷迁移组合物 - Google Patents
含氟化的菲咯啉衍生物的电荷迁移组合物 Download PDFInfo
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- CN1668616A CN1668616A CNA038164620A CN03816462A CN1668616A CN 1668616 A CN1668616 A CN 1668616A CN A038164620 A CNA038164620 A CN A038164620A CN 03816462 A CN03816462 A CN 03816462A CN 1668616 A CN1668616 A CN 1668616A
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Images
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Abstract
本发明涉及一种含有式(I)化合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。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。
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,它含有示于图1的式I菲咯啉衍生物,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、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd;
a、b、c、和d是0或整数,使得a+b=2n+1,并且c+d=5;
n是整数;
x是0或1-3的整数;
y是0、1或2;
附加条件是芳基上的至少一个取代基选自F、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd。
在另一实例中,本发明涉及一种具有示于图2的式II(a)或式II(b)的电荷迁移组合物,其中:
R1、R2、a至d、n、x、和y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;
Q选自单键和多价基团;
m是大于等于2的整数;和
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,该活性层含有示于图1和2的,分别选自式I、II(a)和II(b)的材料,式中R1至R3,Q、a至d、m、n、p、x和y的定义如上,附加条件是在式I中芳基上的至少一个取代基选自F、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd。
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“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“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(亚)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。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(a)和II(b)。
图3显示了本发明电荷迁移组合物的式I(a)至I(i)。
图4显示了用于多配位(multidentate)连接基团的式III(a)至III(h)。
图5显示了场致发光铱配合物的式IV(a)-IV(e)。
图6是发光二极管(LED)的示意图。
图7显示了已知的电子迁移组合物的结构式。
图8显示了LED测试装置的示意图。
具体实施方式
由示于图1的式I所表示的菲咯啉衍生化合物,具有作为电子转移组合物和作为抗淬灭剂(简称为ET/AQ)的特殊用途。
在一个实例中,R1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(arylalkylene)、杂芳烷基、F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd,其中,a至d和n如上限定。
在一个实例中,至少一个R1选自苯基和联苯基,并且它可进一步被选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的基团取代,其中,a至d和n如上限定。
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。
合适的这种类型ET/AQ化合物的例子包括(但并不限于)在图3中给出的式I(a)至I(i)。
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(a)或式II(b)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杂烷基或杂芳基,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。合适的连接基团Q的其他例子,在示于图4中的式III(a)至III(h)中给出。在式III(f)中,任一碳原子可以连于电荷迁移部分。在式III(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菲咯啉部分和Q部分的几何结构。在一个实例中,m是2-10的整数。
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、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、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd,其中,a至d和n如上限定。
在一个实例中,至少一个R1选自苯基和联苯基,并且它可进一步被选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的基团取代,其中,a至d和n如上限定。
在一个实例中,R3选自亚苯基和取代的亚苯基。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、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd,其中,a至d和n如上限定。
在一个实例中,R3选自具有1-20个碳原子的亚烷基。
在一个实例中,在芳基上有选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的至少一个取代基。
式II(a)和式II(b)所表示的组合物可用常规的有机合成技术制备。
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6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))。
本发明菲咯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。
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 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,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。几种合适的铱配合物的例子在图5的式IV(a)-IV(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。本发明的组合物,除了可用于电子迁移和/或抗淬灭层140之外,还可用作光活性层130中发射掺杂物的荷电基质材料。
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(oxinoid)化合物,例如三(8-羟基喹啉)合铝(Alq3),和唑类(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技术,包括但不限于旋转涂覆、蘸涂、和辊对辊技术,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。
本发明的菲咯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1-5
这些实施例阐述了制备具有氟取代基的菲咯啉衍生物的电荷迁移组合物。
实施例1
该实施例阐述了图3中化合物I(c)的制备。
将2,9-二碘-1,10-菲咯啉(900mg,2.08mmol,按Toyota等人,Tetrahedron Letters 1998,39,2697-2700进行制备),3-三氟甲基苯硼酸(trifluoromethylbenzeneboronic acid)(989mg,5.20mmol,Aldrich ChemicalCompany,Milwaukee,WI),四(三苯膦)合钯(tetrakistriphenylphosphinepalladium)(481mg,0.416mmol,Aldrich Chemical Company),和碳酸钠(882mg,8.32mmol)的混合物,在水(20mL)/甲苯(50 mL)中,于氮气下回流15小时。然后,分离出有机层,水层用3×25mL氯仿萃取。合并有机层,用硫酸钠干燥,并蒸干。用己烷/二氯甲烷(1∶1,v∶v)作为洗脱剂,通过硅胶快速色谱完成纯化(产物的Rf=0.25),得到所需产物,1H NMR的纯度>95%,为淡黄色固体(560mg,57%)。1H NMR(CDCl3,300MHz,296K):δ8.81(s,2H),8.63(d,2H,J=7.5Hz),8.36(d,2H,J=8.4Hz),8.19(d,2H,J=8.41Hz),7.84(s,2H),7.68-7.77(m,6H)ppm。19F NMR(CDCl3,282MHz,296K)δ-63.25ppm。
用类似程序制得化合物I(a)、I(g)、I(h)和I(i)。
实施例2
该实施例阐述了图3中化合物I(b)的制备。
用实施例1相同的程序,使用3,8-二溴-1,10-菲咯啉(1.5g,4.4mmol,用Saitoh等人,Canadian Journal of Chemistry 1997,75,1336-1339进行制备)、4-三氟甲基苯硼酸(2.11g,11.1mmol,Lancaster Chemical Company,Windham,NH)、四(三苯膦)合钯(513mg,0.444mmol)和碳酸钠(1.41g,13.3mmol),水(20mL)以及甲苯(100mL)。纯化的实现是通过硅胶快速色谱法(二氯甲烷/甲醇,9∶1,v∶v),然后用冷甲醇洗涤产物,得到白色固体(520mg,25%),1H NMR的纯度>95%。1H NMR(CDCl3,300MHz,296K):δ9.46(d,2H,J=2.3Hz),8.45(d,2H,2.3Hz),7.94(s,2H),7.91(d,4H,J=8.3Hz),7.82(d,4H,J=8.4Hz)ppm。19FNMR(CDCl3,282MHz,296K)δ-63.12ppm。
实施例3
该实施例阐述了图3中化合物I(e)的制备。
让2,9-二碘-1,10-菲咯啉(1.00g,2.31mmol)、4-氟苯硼酸(4-fluorobenzeneboronic acid)(972mg,6.96mmol)、双(二苯基膦基)丁烷(92mg,0.23mmol,Aldrich)、乙酸钯(52mg,0.23mmol,Aldrich)和氟化钾(810mg,13.9mmol,Aldrich)在无水二噁烷(100mL)中回流15小时。之后,减压去除二噁烷,然后按实施例1那样对粗残留物进行水性处理(aqueous work-up)。纯化的完成是通过硅胶快速色谱法(二氯甲烷,100%,产物的Rf=0.57),从而得到浅黄色固体(567mg,67%),1H NMR的纯度>95%。1H NMR(CDC13,300MHz,296K):δ8.43(dd,4H,JHH=10.4Hz,JHF=5.5Hz),8.28(d,2H,J=8.4Hz),7.77(s,2H),7.26(dd,4H,JHH=9.9Hz,JHF=5.9Hz)ppm。19F NMR(CDCl3,282MHz,296K)δ-113.0ppm。
实施例4
该实施例阐述了图3中化合物I(d)的制备。
用实施例20和21相同的程序,使用4,7-二氯-1,10-菲咯啉(300mg,1.20mmol,按J.Heterocyclic Chemistry 1983,20,681-6进行制备)、3,5-双(三氟甲基)苯硼酸(0.930mg,3.60mmol,Aldrich)、双(二苯基膦基)丁烷(154mg,0.361mmol)、乙酸钯(81mg,0.361mmol)、碳酸钠(0.510mg,9.62mmol)、水(5mL)和甲苯(30mL),从而得到所需的固体,为白色固体(410mg,56%)。1H NMR(CDCl3,300MHz,296K):δ9.35(d,2H,J=4.49Hz),8.06(s,2H),8.00(s,4H),7.73(2H,s),7.66(d,2H,J=4.52Hz)ppm。19F NMR(CDCl3,282MHz,296K)δ-63.32ppm。
实施例5
该实施例阐述了图3中化合物I(f)的制备。
用实施例3相同的程序,使用2,9-二氯-菲咯啉(1.0g,4.01mmol,按照Yamada等人Bulletin of the Chemical Society of Japan 1990,63,2710-12进行制备)、3,5-双三氟甲基苯硼酸(2.59g,10.0mmol)、双(二苯基膦基)丁烷(171mg,0.401mmol)、乙酸钯(90mg,0.401mmol)和氟化钾(1.40g,24.1mmol)以及无水二噁烷(100mL)。产物的纯化是通过用二乙醚洗涤粗产物,从而得到所需产物,为白色固体(345mg,14%)。1H NMR(CDCl3,300MHz,296K):δ8.92(d,4H,JHF=1.46Hz),8.45(d,2H,J=8.3Hz),8.25(d,2H,J=8.5Hz),8.02(s,2H),7.91(s,2H)ppm。19F NMR(CDCl3,282MHz,296K)δ-63.50ppm。
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 vsSCE(伏) | LUMO vs真空(eV),E1 |
化合物I(b) | 382 | 318 | -1.56 | -3.28 |
化合物I(a) | 376 | 320 | -1.77 | -3.07 |
化合物I(c) | 368 | 342 | -1.68 | -3.16 |
化合物I(d) | 362 | 310 | -1.54 | -3.3 |
化合物I(e) | 372 | 342 | -1.8 | -3.04 |
化合物I(f) | 370 | 342 | -1.52 | -3.32 |
化合物FDDPA | 368 | 310 | -1.85 | -2.99 |
化合物GDPA | 366 | 316 | -1.95 | -2.89 |
实施例6
本实施例说明图5中式IV(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7
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总结了用本发明的菲咯啉衍生物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(示于图15),而发射层是实施例6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。
表2器件 | |||||
样品 | HT() | EL, | ET/AQ, | ET, | 阴极, |
化合物F | 507 | 407 | 化合物F408 | Al 721 | |
化合物G | 507 | 405 | 化合物G407 | Al 732 | |
2-1 | 505 | 406 | I(a)450 | Al 717 | |
2-2 | 506 | 430 | I(b)405 | Al 736 | |
2-3 | 515 | 407 | I(c)409 | Al 728 | |
2-4 | 516 | 419 | I(d)406 | Al 717 | |
2-5 | 505 | 415 | I(e)432 | Al 740 | |
2-6 | 514 | 402 | I(f)431 | Al 738 | |
2-7 | 515 | 407 | I(g)409 | Al 728 |
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8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。
使用本发明的菲咯啉ET/AQ组合物的器件结果,列于下表3。
表3设备的场致发光特性 | |||
样品 | 峰值辐射强度,cd/m2 | 峰值辐射强度处的效率,cd/A | 峰值效率,cd/A |
化合物F | 3000于22V | 10 | 14 |
化合物G | 4500于19V | 10 | 20 |
2-1 | 4000于19V | 8.5 | 9.5 |
2-2 | 3500于19V | 6 | 17 |
2-3 | 1200±300于24V | 2 | 6 |
2-4 | 2200于25V | 16 | |
2-5 | 1000于23V | 6 | |
2-6 | 900于27V | 8.5 | |
2-7 | 1400于24V | 6 |
Claims (39)
1.一种组合物,其特征在于,它含有示于图1的式I菲咯啉衍生物,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、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd;
a、b、c、和d是0或整数,使得a+b=2n+1,并且c+d=5;
n是整数;
x是0或1-3的整数;
y是0、1或2;
附加条件是芳基上的至少一个取代基选自F、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd。
2.如权利要求1所述的组合物,其特征在于,R1选自苯基、取代的苯基、联苯基、取代的联苯基、吡啶基、取代的吡啶基、联吡啶基和取代的联吡啶基。
3.如权利要求2所述的组合物,其特征在于,R1选自取代的苯基、取代的联苯基、取代的吡啶基和取代的联吡啶基,且具有至少一个选自以下的取代基:烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、CnHaFb、和C6HcFd。
4.如权利要求1所述的组合物,其特征在于,至少一个R1选自取代的苯基和取代的联苯基,且具有至少一个选自以下的取代基:F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
5.如权利要求1所述的组合物,其特征在于,所述的菲咯啉衍生物选自图3中的式I(b)至I(f)。
6.一种组合物,其特征在于,它具有选自示于图2的式II(a)和式II(b)的结构式,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、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd;
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;
Q选自单键和多价基团;
m是大于等于2的整数;
n是整数;
p是0或1;x是0或1-3的整数;以及
y是0、1或2。
7.如权利要求6所述的组合物,其特征在于,Q选自具有至少两个连接点位的烃基,选自脂族基团、杂脂族基团、芳族基团和杂芳族基团。
8.如权利要求7所述的组合物,其特征在于,Q选自亚烷基、亚杂烷基、亚烯基、亚杂烯基、亚炔基、和亚杂炔基。
9.如权利要求6所述的组合物,其特征在于,Q选自单环芳族基团、多环芳族基团、稠环芳族基团、单环杂芳族基团、多环杂芳族基团、稠环杂芳族基团、芳基胺、硅烷和硅氧烷。
10.如权利要求6所述的组合物,其特征在于,Q选自图4中的式III(a)至III(h)。
11.如权利要求6所述的组合物,其特征在于,R1选自苯基、取代的苯基、联苯基、取代的联苯基、吡啶基、取代的吡啶基、联吡啶基和取代的联吡啶基。
12.如权利要求11所述的组合物,其特征在于,R1选自取代的苯基、取代的联苯基、取代的吡啶基、和取代的联吡啶基,且具有至少一个选自以下的取代基:烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
13.如权利要求6所述的组合物,其特征在于,至少一个R1选自取代的苯基和取代的联苯基,且具有至少一个选自以下的取代基:F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
14.如权利要求6所述的组合物,其特征在于,R3选自亚苯基和取代的亚苯基。
15.如权利要求14所述的组合物,其特征在于,具有至少一个选自以下的取代基:烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
16.如权利要求6所述的组合物,其特征在于,R3选自具有1-20个碳原子的亚烷基。
17.如权利要求6所述的组合物,其特征在于,在芳基上有选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的至少一个取代基。
18.一种电子器件,其特征在于,它包括至少一个含有示于图1的式I的菲咯啉衍生物的层,式中:
R1和R2在各种情况下可相同或不同,并且选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd;
a、b、c、和d是0或整数,使得a+b=2n+1,并且c+d=5;
n是整数;
x是0或1-3的整数;
y是0、1或2;
附加条件是芳基上的至少一个取代基选自F、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd。
19.如权利要求18所述的器件,其特征在于,R1选自苯基、取代的苯基、联苯基、取代的联苯基、吡啶基、取代的吡啶基、联吡啶基和取代的联吡啶基。
20.如权利要求19所述的器件,其特征在于,R1选自取代的苯基、取代的联苯基、取代的吡啶基和取代的联吡啶基,且具有至少一个选自以下的取代基:烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、CnHaFb、和C6HcFd。
21.如权利要求18所述的器件,其特征在于,至少一个R1选自取代的苯基和取代的联苯基,且具有至少一个选自以下的取代基:F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
22.如权利要求18所述的电子器件,其特征在于,所述的菲咯啉衍生物选自图3中的式I(a)至I(i)。
23.一种电子器件,其特征在于,它包括至少一个层,所述层含有选自示于图2的式II(a)和式II(b)的结构式的组合物,式中:
R1和R2在各种情况下可相同或不同,并且选自H、F、Cl、Br、烷基、杂烷基、烯基、炔基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd;
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;
Q选自单键和多价基团;
m是大于等于2的整数;和
n是整数;
p是0或1;
x是0或1-3的整数;以及
y是0、1或2。
24.如权利要求23所述的器件,其特征在于,Q选自具有至少两个连接点位的烃基,选自脂族基团、杂脂族基团、芳族基团和杂芳族基团。
25.如权利要求24所述的器件,其特征在于,Q选自亚烷基、亚杂烷基、亚烯基、亚杂烯基、亚炔基、和亚杂炔基。
26.如权利要求23所述的器件,其特征在于,Q选自单环芳族基团、多环芳族基团、稠环芳族基团、单环杂芳族基团、多环杂芳族基团、稠环杂芳族基团、芳基胺、硅烷和硅氧烷。
27.如权利要求23所述的器件,其特征在于,Q选自图4中的式III(a)至III(h)。
28.如权利要求23所述的器件,其特征在于,R1选自苯基、取代的苯基、联苯基、取代的联苯基、吡啶基、取代的吡啶基、联吡啶基和取代的联吡啶基。
29.如权利要求28所述的器件,其特征在于,R1选自取代的苯基、取代的联苯基、取代的吡啶基、和取代的联吡啶基,且具有至少一个选自以下的取代基:烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
30.如权利要求23所述的器件,其特征在于,至少一个R1选自取代的苯基和取代的联苯基,且具有至少一个选自以下的取代基: F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
31.如权利要求23所述的器件,其特征在于,R3选自亚苯基和取代的亚苯基。
32.如权利要求31所述的器件,其特征在于,具有至少一个选自以下的取代基:烷基、杂烷基、芳基、杂芳基、芳烷基、杂芳烷基、F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd。
33.如权利要求23所述的器件,其特征在于,R3选自具有1-20个碳原子的亚烷基。
34.如权利要求23所述的器件,其特征在于,在芳基上有选自F、CnHaFb、OCnHaFb、C6HcFd和OC6HcFd的至少一个取代基。
35.一种组合物,其特征在于,它含有示于图2的式II菲咯啉衍生物,其中:
R2和R3在各种情况下可相同或不同,并且选自H、烷基、杂烷基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd;
a、b、c、和d是整数,使得a+b=2n+1,并且c+d=5;
x是0或1-3的整数;
y是0、1或2;
附加条件是芳基上的至少一个取代基选自F、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd。
36.一种组合物,其特征在于,它选自示于图2的式II(a),其中:
Q选自单键和多价基团;
m是2-10的整数;
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;
R1和R2在各种情况下可相同或不同,并且选自H、烷基、杂烷基、芳基、杂芳基、CnHaFb、OCnHaFb、C6HcFd、和OC6HcFd;
y是0、1或2,
a、b、c、和d是整数,使得a+b=2n+1,并且c+d=5。
37.如权利要求36所述的组合物,其特征在于,Q选自图4中的式III(a)至III(h)。
38.一种电子器件,其特征在于,它包括至少一个层,所述层含有权利要求35-37中任一项所述的组合物。
39.权利要求35-37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。
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