CN100438123C - 含有氟化苯基吡啶、苯基嘧啶和苯基喹啉的电致发光铱化合物及用该化合物制备的器件 - Google Patents

含有氟化苯基吡啶、苯基嘧啶和苯基喹啉的电致发光铱化合物及用该化合物制备的器件 Download PDF

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CN100438123C
CN100438123C CNB018148611A CN01814861A CN100438123C CN 100438123 C CN100438123 C CN 100438123C CN B018148611 A CNB018148611 A CN B018148611A CN 01814861 A CN01814861 A CN 01814861A CN 100438123 C CN100438123 C CN 100438123C
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V·A·佩特洛夫
Y·王
V·格鲁辛
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Abstract

本发明一般涉及电致发光的Ir(III)化合物，用来制造Ir(III)化合物的取代的2-苯基吡啶、苯基嘧啶和苯基喹啉，以及用该Ir(III)化合物制备的器件。

Description

含有氟化苯基吡啶、苯基嘧啶和苯基喹啉的电致发光铱化合物及用该化合物制备的器件
发明背景
发明领域
本发明涉及铱(III)与氟化的苯基吡啶、苯基嘧啶和苯基喹啉的电致发光配合物，其还涉及其中活性层包含电致发光的Ir(III)配合物的电子器件。
相关技术描述
在许多不同种类的电子设备中存在发光的有机电子器件，如构成显示的发光二极管。在所有这样的器件中，有机活性层夹在两个电接触层之间。至少一个电接触层是透光的，使得光可以通过该电接触层。在对电接触层施加电压时有机活性层发射通过透光电接触层的光。
众所周知，在发光二极管中使用有机电致发光化合物作为活性成分。已知简单的有机分子如蒽、噻二唑衍生物和香豆素衍生物呈现电致发光现象。半导体共轭聚合物也已经用作电致发光成分，例如在Friend等的U.S.5,247,190、Heeger等的U.S.5,408,109和Nakano等的公开欧洲专利申请443861中公开的。8-羟基喹啉酸盐(quinolate)与三价金属离子的配合物，尤其是与铝的配合物已经广泛用作电致发光成分，例如在Tang等的U.S.5,552,678中所公开的。
Burrows和Thompson已经报道，面式-三(2-苯基吡啶)铱可以用作有机发光器件中的活性成分(Appl.Phys.Lett.1999，75，4.)。当在主体导电材料中存在铱化合物时，性能可以最大化。Thompson进一步报道了其中活性层是用面式-三[2-(4’，5’-二氟苯基)吡啶-C’2，N]铱(III)掺杂的聚(N-乙烯基咔唑)的器件(Polymer Preprints 2000，41(1)，770)。
但是，对于改善效率的电致发光化合物存在越来越多的需求。
发明概述
本发明涉及一种铱化合物(一般称为“Ir(III)化合物”)，其具有至少两个2-苯基吡啶配体，其中，在该配体上存在至少一个氟或氟化的基团。该铱化合物具有以下的第一分子式：
IrLaLbLc xL’yL”z                 (第一分子式)
这里：
x＝0或1，y＝0、1或2，且z＝0或1，条件是：
x＝0或y+z＝0且
当y＝2时，则z＝0；
L’＝二齿配体或单齿配体，并且不是苯基吡啶、苯基嘧啶或苯基喹啉；条件是：
当L’为单齿配体时，y+z＝2，且
当L’为二齿配体时，z＝0；
L”＝单齿配体，并且不是苯基吡啶、和苯基嘧啶或苯基喹啉；且
La、Lb和Lc彼此相同或不同并且La、Lb和Lc的每一个具有以下结构(I)：
Figure C0181486100141
其中：
相邻的R1-R4和R5-R8对可以结合形成5元或6元环，
R1-R8的至少一个选自F、CnF2n+1、OCnF2n+1和OCF2X，这里，n＝1-6且X＝H、Cl或Br，且
A＝C或N，条件是当A＝N时，没有R1。
在另一个实施方案中，本发明涉及取代的2-苯基吡啶、苯基嘧啶和苯基喹啉前驱体化合物，由其制备以上的Ir(III)化合物。该前驱体化合物具有以下结构(II)或(III)：
Figure C0181486100151
这里，A和R1-R8是如以上结构(I)中所定义的，
且R9为H。
Figure C0181486100152
这里：
R10-R19的至少之一选自F、CnF2n+1、OCnF2n+1和OCF2X，这里，n＝1-6且X＝H、Cl或Br，且R20为H。
可以理解，没有关于苯基吡啶、苯基嘧啶和苯基喹啉键的自由旋转。但是，对于本文的讨论，该化合物按照一个取向描述。
在另一个实施方案中，本发明涉及一种具有至少一个发光层的有机电子器件，该发光层包含上述Ir(III)化合物，或上述Ir(III)化合物的组合。
本文所有的术语“化合物”是指一种由分子构成的未荷电物质，这些分子进一步由原子组成，其中，这些原子不能通过物理方法分开。术语“配体”是指连接到金属离子的配位球的分子、离子或原子。术语“配合物”在用作名词时，是指有至少一个金属离子和至少一个配体的化合物。术语“基团”是指化合物的一部分，如在有机化合物中的取代基或在配合物中的配体。术语“表面的”是指配合物Ma3b3的异构体，其具有八面体几何结构，其中，三个“a”基团都是相邻的，即在八面体一个面的角部。术语“经式”是指具有八面体几何结构的配合物Ma3b3的异构体，其中，三个“a”基团占据使得两个相互反位(trans)的三个位置。术语“相邻”在用于提及器件中的层时，不一定是指一个层直接与另一个层相邻。另一方面，短语“相邻的R基团”用来指在化学分子式中相互靠近的R基团(即在通过一个键结合的原子上的R基团)。术语“光敏的”是指呈现出电致发光和/或光敏性的任何材料。
附图简述
图1是发光器件(LED)的示意图。
图2是LED测试装置的示意图。
优选的实施方案详述
本发明的Ir(III)化合物具有以上的第一分子式Ir(III)LaLbLc xL’y。
上述Ir(III)化合物通常称为环金属化的配合物：具有以下第二分子式的Ir(III)化合物通常还称为双-环金属化配合物：
IrLaLbL’yL”z               (第二分子式)
这里：
y、z、La、Lb、L’和L”是在以上第一分子式中所定义的。
具有以下第三分子式的Ir(III)化合物通常还称为三-环金属化配合物：
IrLaLbLc                   (第三分子式)
其中：
La、Lb和Lc是在以上第一分子式中定义的。
优选的环金属化配合物是中性和非离子的，并且可以完整无缺地升华。通过真空沉积获得的这些材料的薄膜表现出良好到优异的电致发光性能。向铱原子上的配体引入氟取代基提高配合物的稳定性和挥发性。结果，可以在较低温度进行真空沉积并且可以避免配合物的分解。向配体中引入氟取代基通常可以减小非辐射性衰减速度和固体状态的自猝灭现象。这些减小可能导致发光效率增大。具有供电子和吸电子性质的取代基的变化可以进行化合物电致发光性能的微调，因此优化电致发光器件中的亮度和效率。
不希望受理论限制，可以认为来自铱化合物的发射是基于配体的，来源于金属与配位体的电荷转移。所以，可以表现出电致发光现象的化合物包括以上第二分子式IrLaLbL’yL”z的化合物，和以上第三分子式IrLaLbLc的化合物，其中在第三分子式中的所有的La、Lb和Lc是苯基吡啶、苯基嘧啶或苯基喹啉。结构(I)和(II)的R1-R8基团和以上结构(III)的R10-R19基团可以选自有机化合物的常规取代基，如烷基、烷氧基、卤素、硝基和氰基以及氟、氟代烷基和氟代烷氧基。这些基团可以部分或全部氟化(全氟化)。优选的铱化合物具有选自氟、全氟代烷基(CnF2n+1)和全氟代烷氧基(OCnF2n+1)或者分子式OCF2X基团的全部R1-R8和R10和R19基团，其中全氟代烷基和烷氧基含有1-6个碳原子，X＝H、Cl或Br。
已经发现，当R1-R8和R10-R19基团的任一个或多个是硝基时，环金属化铱配合物的电致发光性能较差。所以，优选的是R1-R8和R10-R19基团中没有一个是硝基。
含氮环可以是吡啶环、嘧啶或喹啉。优选的是至少一个氟化取代基在含氮环上；最优选的是CF3。
对于过渡金属配位化学已知的任何常规配体适合于用作L’和L”配体。二齿配体的实施例包括有两个配位基团的化合物，如乙二胺和乙酰基丙酮酸盐，其可以被取代。单齿配体的实施例包括氯化物和硝酸根离子以及一元胺。优选的是铱配合物是中性且可升华的。如果使用单一的二齿配体，其应该具有-1的净电荷。如果使用两个单齿配体，它们应该具有-1的总净电荷。双-环金属化配合物可以用于制备三-环金属化配合物，其中配体不都是相同的。
在一个优选的实施方案中，铱化合物具有如上所述的第三分子式IrLaLbLc。
在更优选的实施方案中，La＝Lb＝Lc·如用单晶X-射线衍射所测定的，这些更优选的化合物通常表现出面式几何结构，其中，配位到铱的氮原子相对于配位到铱的碳原子是反位的。这些更优选的化合物具有以下第四分子式：
面式-Ir(La)3                    (第四分子式)
其中，La具有以上的结构(I)。
这些化合物可以表现出经式几何结构，其中配位到铱的两个氮原子相互是反位的。这些化合物具有以下第五分子式：
经式-Ir(La)3                  (第五分子式)
其中，La具有以上的结构(I)。
以上第四分子式和第五分子式的化合物的实例在下表1中给出：
Figure C0181486100181
以上第二分子式IrLaLbL’yL”z的化合物的实例包括化合物1-n、1- o、1-p、1-w和1-x，分别具有以下的结构(IV)、(V)、(VI)、(IX)和(X)：
Figure C0181486100192
Figure C0181486100201
以上第三分子式IrLaLbLc的铱配合物一般用适当取代的2-苯基吡啶、苯基嘧啶或苯基喹啉制备。使用取代的2-氯代吡啶、2-氯代嘧啶或2-氯代喹啉与芳基硼酸的Suzuki偶合，以良好到优异的产率制备了如以上结构(II)所示的取代2-苯基吡啶、苯基嘧啶和苯基喹啉，如O.Lohse，P.Thevenin，E.Waldvogel Synlett，1999，45-48中所述。对于吡啶衍生物用以下方程(1)说明了该反应，其中，X和Y表示取代基：
Figure C0181486100211
具有以上结构(II)的2-苯基吡啶和2-苯基嘧啶化合物的实例在下表2中给出：
Figure C0181486100212
Figure C0181486100221
具有以上结构(III)的取代的2-苯基喹啉化合物的一个实例是化合物2-u，其中，R17＝CF3且R10-R16和R18-R20＝H。
如此制备的2-苯基吡啶、嘧啶和喹啉用于合成环金属化铱配合物。使用市售水合三氯化铱和三氟乙酸银，已经开发了方便的一步法。这些反应通常在3当量AgOCOCF3的存在下没有溶剂，用过量的2-苯基吡啶、嘧啶或喹啉进行。对于2-苯基吡啶，在以下方程(2)中说明了该反应：
Figure C0181486100222
三-环金属化铱配合物经分离、提纯并通过元素分析、1H和19F NMR谱数据完全表征，并且对于化合物1-b、1-c和1-e，进行单晶X-射线衍射。在某些情况下，获得异构体的混合物。通常可以使用该混合物而不分离各种异构体。
具有以上第二分子式IrLaLbL’yL”z的铱配合物在某些情况下可以使用与制备具有以上第三分子式IrLaLbLc的化合物的相同合成过程与反应混合物分离。通过先制备具有以下结构VII的中间体铱二聚物，也可以制备这些配合物：
其中：
B＝H、CH3或C2H5且
其中，La、Lb、Lc和Ld可以彼此相同或不同并且La、Lb、Lc和Ld的每一个具有以上的结构(I)。
一般通过先使水合三氯化铱与2-苯基吡啶、苯基嘧啶或苯基喹啉反应，并加入NaOB，可以制备铱二聚物。
一种特别有用的铱二聚物是羟基铱二聚物，具有以下结构VIII：
Figure C0181486100232
该中间体可以通过加入乙酰乙酸乙酯来制备化合物1-p。
电子器件
本发明还涉及包含至少一个光敏层的电子器件，该光敏层位于两个电接触层之间，其中，该器件的所述至少一层包括本发明的铱配合物。这些器件通常有额外的空穴传输和电子传输层。典型的结构表示在图1中。器件100有阳极层110和阴极层150。靠近阳极是包含空穴输送材料的层120。靠近阴极的是包含电子输送材料的层140。在空穴输送层与电子输送层之间的是光敏层130。
取决于器件100的用途，光敏层130可以是由外加电压激活的发光层(如在发光二极管或发光电化学电池中)，对辐射能量产生反应并在有或没有外加偏压下产生信号的材料层(如在光电检测器中)。光电检测器的实例包括光电导管、光敏电阻、光电开关、光电晶体管和光电管，以及光电池，这些术语描述在Karkus，John，Electronics andNucleonics Dictionary，470和476页中(McGraw-Hill，Inc.1966)。
本发明的铱化合物特别用作层130中的光敏材料，或者用作层140中的电子传输材料。优选地，本发明的铱配合物用作二极管中的发光材料。已经发现，在这些用途中，本发明的氟化化合物不需要在固体基质稀释剂中来使其有效。按所述层的总重量计，大于20重量％铱化合物到100重量％铱化合物的层可以用作发光层。这与非氟化的铱化合物反式(2-苯基吡啶)铱(III)形成对比，该化合物在发射层中的存在量仅为6-8重量％时获得最高效率。这对减少自猝灭效应是必要的。其它材料可以存在于用所述铱化合物的发射层中。例如，可以存在荧光染料以改变发射的颜色。还可以加入稀释剂。稀释剂可以是聚合材料如聚(N-乙烯基咔唑)和聚硅烷。其也可以是小分子，如4，4’-N，N’-二咔唑联苯或叔芳胺。当使用稀释剂时，铱化合物一般少量存在，通常小于20重量％，优选小于10重量％，以所述层的总重量为基准。
在某些情况下，铱配合物可以以一种以上的异构形式存在，或者可以存在不同配合物的混合物。可以理解，在OLED的以上讨论中，术语“铱化合物”意欲包括化合物和/或异构体的混合物。
为了获得高效率的LED，空穴传输材料的HOMO(最高被占据分子轨道)应该与阳极的功函数一致(align)，电子传输材料的LUMO(最低未占据分子轨道)应该与阴极的功函数一致。材料的化学相容性和升华温度在选择电子和空位传输材料中也是重要的因素。
在OLED中的其它层可以用该层中可用的任何已知材料制成。阳极110是对于注入正电荷载流子特别有效的电极。例如其可以用含有金属、混合金属、合金、金属氧化物或混合金属氧化物制成，或者其可以是导电聚合物。合适的金属包括第11族金属、在第4、5和6族中的金属以及第8-10族过渡金属。如果阳极是透光的，一般使用第12、13和14族金属的混合金属氧化物如铟-锡氧化物。全文中使用IUPAC编号系统，其中元素周期表的族从左到右编号为1-18(CRCHandbook of Chemistry and Physics，第81版，2000)。阳极110还可以包含有机材料如聚苯胺，如在“用可溶性导电聚合物制备的柔性发光二极管”Nature vol.357，第477-479页(1992年6月11日)。阳极和阴极至少之一应该至少部分透明，以便可以观察到所产生的光。
例如，层120的空穴传输材料的实例已经由Y.Wang总结在Kirk-Othmer Othmer Encyclopedia of Chemical Technology，第四版，Vol.18，第837-860页中。可以使用空穴传输分子和聚合物。常用的空穴传输分子是：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)、a-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)、三苯基胺(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]吡唑啉(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-1-苯基)-(1，1’-联苯基)-4，4’-二胺(TTB)，和卟啉化合物如酞青铜。常用的空穴传输聚合物是聚乙烯基咔唑、(苯基甲基)聚硅烷和聚苯胺。通过向聚合物如聚苯乙烯和聚碳酸酯中掺杂诸如以上提及的空穴传输分子也可以获得空穴传输聚合物。
层140的电子传输材料的实例包括金属螯合oxinoid化合物，如三(8-羟基氢醌)铝(Alq3)；菲咯啉型化合物，如2，9-二甲基-4，7-二苯基-1，10-菲咯啉(DDPA)或4，7-二苯基-1，10-菲咯啉(DPA)；和唑化合物如2-(4-联苯基)-5-(4-叔丁基苯基)-1，3，4-噁二唑(PDB)和3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1，2，4-三唑(TAZ)。层140可以用来促进电子传输，还用作缓冲层或限制层，以防止在层边界处的激发子猝灭。优选地，该层促进电子迁移并减少激发子猝灭。
阴极150是注入电子或负电荷载流子特别有效的电极。阴极可以是具有比阳极更低的功函数的任何金属或非金属。用于阴极的材料可以选自第1族(例如Li、Cs)的碱金属、第2族(碱土)金属、第12族金属，包括稀土元素和镧系元素以及锕系元素。可以使用诸如铝、铟、钙、钡、钐和镁及其组合的材料。含锂的有机金属化合物也可以沉积在有机层和阴极层之间，以降低操作电压。
已知在有机电子器件中有其它层。例如，在导电聚合物层120和活性层130之间可以有一层(未示出)，以促进正电荷传输和/或层的能带间隙匹配，或者作为保护层。类似地，在活性层130与阴极层150之间可以有附加层(未示出)，以促进负电荷传输和/或各层之间能带间隙匹配，或者用作保护层。可以使用本领域已知的层。此外，任何上述层可以由两层或多层构成。此外，一些或全部无机阳极层110、导电聚合物层120、活性层130和阴极层150可以被表面处理，以提高电荷载流子传输效率。对于每个成分层的材料选择优选通过平衡提供具有高器件效率的器件的目的决定。
可以理解，每个功能层可以由一层以上的层构成。
通过在合适的基体上依次气相沉积各个层可以制备该器件。可以使用诸如玻璃和聚合薄膜的基质。可以使用常规的气相沉积技术，如热蒸发、化学气相沉积等。另外，这些有机层可以使用任何传统涂敷技术从合适溶剂中的溶液或分散体中涂敷。一般来说，不同层具有以下厚度范围：阳极110，500-5000埃，优选为1000-2000埃；空穴传输层120，50-1000埃，优选为200-800埃；发光层130，10-1000埃，优选为100-800埃；电子传输层140，50-1000埃，优选为200-800埃；阴极150，200-10000埃，优选为300-5000埃。器件中电子-空穴再结合区的位置，以及由此产生的器件的发射光谱可以受每层的相对厚度影响。因此，应该选择电子传输层的厚度使得电子-空穴再结合区在发光层中。希望的层厚比取决于所用材料的具体性质。
可以理解，用本发明的铱化合物制备的器件的效率可以进一步通过优化器件中的其它层来进一步改善。例如，可以使用更有效的阴极如Ca、Ba或LiF。导致操作电压降低或提高量子效率的成型基质和新的空穴传输材料也是可以应用的。还可以加入其它层以设计各层的能级并促进电致发光。
本发明的铱配合物通常是磷光的和电致发光的，可以用于除了OLED以外的用途中。例如，铱的有机金属配合物已经用作氧敏指示剂，在生物测定中作为荧光指示剂，以及用作催化剂。双环金属化配合物可以用来和成其中三个配位体相同或不同的三环金属化配合物。
实施例
以下实施例说明本发明的一些特征和优点。它们是本发明的说明，但不是限制性的。除了另外说明，所有的百分比按重量计。
实施例1
本实施例说明用来形成铱化合物的2-苯基吡啶和2-苯基嘧啶的制备。
所用的一般过程描述在O.Lohse，P.Thevenin，E.WaldvogelSynlett，1999，45-48页中。在典型的实验中，把200毫升脱气水、20克碳酸钾、150毫升1，2-二甲氧基乙烷、0.5克Pd(PPh3)4、0.05摩尔取代的2-氯代吡啶(喹啉或嘧啶)和0.05摩尔取代的苯基硼酸的混合物回流(80-90℃)16-30小时。所得的反应混合物用300毫升水稀释，并用CH2Cl2(2×100毫升)萃取。组合的有机层在MgSO4上干燥，并且通过真空排出溶剂。液体产物通过部分真空蒸馏提纯。固体材料从己烷中重结晶。所分离的材料的典型纯度＞98％。新材料的原料、产率、熔点和沸点在表3中给出。NMR数据和分析数据在表4中给出。
表3
2-苯基吡啶、苯基嘧啶和苯基喹啉的制备
Figure C0181486100271
表4
2-苯基吡啶、苯基嘧啶和苯基喹啉的性质
表4
(续)
Figure C0181486100291
表4
(续)
Figure C0181486100301
实施例2
本实施例说明以上第四分子式的面式-Ir(La)3的铱化合物的制备。
在典型的实验中，把IrCl3·nH2O(53-55％Ir)、AgOCOCF3(3.1当量/Ir)、2-芳基吡啶(过量)和(任选)少量水的混合物在180-195℃(油浴)在N2下剧烈搅拌2-8小时。所得的混合物用CH2Cl2充分萃取直至萃取物无色。萃取物通过二氧化硅柱过滤以产生清澈的黄色溶液。该溶液的蒸发得到残渣，其用甲醇处理以产生有色晶体三-环金属化的Ir配合物。通过过滤、用甲醇洗涤、在真空下干燥、并通过结晶化(任选)提纯、真空升华、或Soxhlet萃取来分离配合物。产率：10-82％。所有的材料用NMR光谱数据和元素分析表征，结果在下表5中给出。对于该系列的三种配合物，获得单晶X-射线结构。
化合物1-b
在温度缓慢(30分钟)升高到185℃(油浴)过程中，把IrCl3·nH2O(54％Ir；508毫克)、2-(4-氟代苯基)-5-三氟甲基吡啶，化合物kk(2.20克)、AgOCOCF3(1.01克)和水(1毫升)的混合物在N2流下剧烈搅拌。在185-190℃下2小时后，该混合物凝固。把该混合物冷却到室温。用二氯甲烷萃取固体直至萃取物脱色。混合的二氯甲烷溶液通过短二氧化硅柱过滤并蒸发。在向残渣中加入甲醇(50毫升)后，把烧瓶在-10℃保温一整夜。分离三-环金属化配合物的黄色沉淀物，化合物b，用甲醇洗涤并在真空下干燥。产率：1.07克(82％)。通过在1，2-二氯乙烷中缓慢冷却其温热溶液，获得该配合物的X-射线级晶体。
化合物1-e
在温度缓慢(15分钟)升高到192℃(油浴)过程中，把IrCl3·nH2O(54％Ir；504毫克)、2-(3-氟代甲基苯基)-5-三氟甲基吡啶，化合物bb(1.60克)、和AgOCOCF3(1.01克)的混合物在N2流下剧烈搅拌。在190-195℃下6小时后，该混合物凝固。把该混合物冷却到室温。把固体放在二氧化硅柱上，然后用大量二氯甲烷洗涤。滤液蒸发后的残渣用甲醇处理，以产生黄色固体。收集该固体并用二氯甲烷在25毫升微-Soxhlet萃取器中萃取提纯。分离三-环金属化配合物的黄色沉淀物，化合物e，用甲醇洗涤并在真空下干燥。产率：0.59克(39％)。从热的1，2-二氯乙烷中获得配合物的X-射线级晶体。
化合物1-d
在190-195℃(油浴)把IrCl3·nH2O(54％Ir；508毫克)、2-(2-氟代苯基)-5-三氟甲基吡啶，化合物aa(1.53克)、和AgOCOCF3(1.01克)的混合物在N2流下剧烈搅拌6小时15分。把该混合物冷却到室温，然后用热1，2-二氯乙烷萃取。把该萃取物通过短二氧化硅柱过滤并蒸发。用甲醇(20毫升)处理残渣导致希望产物即化合物d的沉淀，其通过过滤分离，用甲醇洗涤并在真空下干燥。产率：0.63克(49％)。从二氯甲烷/甲醇中获得配合物的X-射线级晶体。
化合物1-i
在190-195℃(油浴)把IrCl3·nH2O(54％Ir；503毫克)、2-(4-氟代甲氧基苯基)-5-三氟甲基吡啶，化合物ee(2.00克)、和AgOCOCF3(1.10克)的混合物在N2流下剧烈搅拌2小时45分。把该混合物冷却到室温，然后用二氯甲烷萃取。把该萃取物通过短二氧化硅柱过滤并蒸发。用甲醇(20毫升)处理残渣导致希望产物即化合物i的沉淀，其通过过滤分离，用甲醇洗涤并在真空下干燥。产率为0.86克。另外，通过蒸发母液并向残渣中加入石油醚获得0.27克配合物。总产率：1.13克(72％)。
化合物1-q
在温度缓慢(30分钟)升高到185℃(油浴)过程中，把IrCl3·nH2O(54％Ir；530毫克)、2-(3-甲氧基苯基)-5-三氟甲基吡啶(2.50克)、AgOCOCF3(1.12克)和水(1毫升)的混合物在N2流下剧烈搅拌。在185℃下1小时后，该混合物凝固。把该混合物冷却到室温。把固体用二氯甲烷萃取直至萃取物脱色。把混合的二氯甲烷溶液通过短二氧化硅柱过滤并蒸发。残渣用己烷洗涤，然后从1，2-二氯乙烷-己烷中重结晶(两次)。产率：0.30克。19F NMR(CD2Cl2，20℃)，δ：-63(s).1H NMR(CD2Cl2，20℃)，δ：8.1(1H)，7.9(1H)，7.8(1H)，7.4(1H)，6.6(2H)，4.8(3H)。从1，2-二氯乙烷-己烷中获得配合物(1，2-二氯乙烷，己烷溶剂化物)的X-射线级晶体。这种面式配合物是橙色荧光物质。
类似地制备化合物1-a、1-c、1-f-1-h、1-j-1-m和1-r。在化合物1-j的制备中，获得氟在R6或R8位置上的异构体的混合物。
Figure C0181486100332
实施例3
本实施例说明以上第二分子式IrLaLbLc xL’yL”z的铱配合物的制备。
化合物1-n
在190-195℃把IrCl3·nH2O(54％Ir；510毫克)、2-(3-氟代甲基苯基)喹啉(1.80克)、和三氟代乙酸银(1.10克)的混合物在N2流下剧烈搅拌4小时。所得的固体在二氧化硅上用二氯甲烷层析，以产生二环金属化配合物与未反应配体的混合物。通过用温热己烷萃取把后者从混合物中去除。在萃取物变成无色后，收集不溶于己烷的固体，并在真空下干燥。产率为0.29克。19F NMR：-63.5(s，6F)，-76.5(s，3F)。通过单晶X射线衍射研究获得该配合物的结构。
化合物1-o
在190℃把IrCl3·nH2O(54％Ir；500毫克)、2-(2-氟代苯基)-3-氯-5-三氟代甲基吡啶(2.22克)、水(0.3毫升)和三氟代乙酸银(1.00克)的混合物搅拌1.5小时。固体产物在二氧化硅上用二氯甲烷层析，以产生0.33克2∶1的二环金属化配合物水合三氟代乙酰基配合物，化合物1-p和未反应配体的共结晶加成物。19F NMR：-63.0(9F)，-76.5(3F)，-87.7(2F)，-114.4(1F)。通过从二氯甲烷-己烷中重结晶去除共结晶的苯基吡啶配体。通过单晶X-射线衍射研究获得加成物和配合物的结构。
实施例4
本实施例说明具有以上结构(VIII)的羟基铱二聚物的制备。
把IrCl3·nH2O(54％Ir；510毫克)、2-(4-氟代苯基)-5-三氟代甲基吡啶(725毫克)、水(5毫升)和2-乙氧基乙醇(20毫升)的混合物在回流下剧烈搅拌4.5小时。在加入NaOH(2.3克)在水(5毫升)中的溶液后，加入20毫升水，把该混合物在回流下搅拌2小时。把该混合物冷却到室温，用50毫升水稀释，并过滤。把固体产物用30毫升1，2-二氯乙烷和NaOH水溶液(2.2克在8毫升水中)在回流下剧烈搅拌6小时。从混合物中蒸发有机溶剂，留下有机固体在水相中的悬浮液。有机固体通过过滤分离，用水充分洗涤，并在真空下干燥，以产生0.94克(95％)的铱羟基二聚物(光谱纯)。1H NMR(CD2Cl2)：-1.0(s，1H，IrOH)，5.5(dd，2H)，6.6(dt，2H)，7.7(dd，2H)，7.9(dd，2H)，8.0(d，2H)，9.1(d，2H)。19F NMR(CD2Cl2)：-62.5(s，3F)，-109.0(ddd，1F)。
实施例5
本实施例说明从铱二聚物制备二-环金属化配合物。
化合物1-p
把来自实施例4的铱羟基二聚物(100毫克)、乙酰乙酸乙酯(0.075毫升；4倍过量)和二氯甲烷(4毫升)的混合物在室温搅拌一整夜。该溶液通过短二氧化硅柱过滤并蒸发，获得橙黄色固体，其用己烷洗涤并干燥。配合物的产率为109毫克(94％)。1H NMR(CD2Cl2)：1.1(t，CH3)，3.9(dm，CH2)，4.8(s，CH3COCH)，5.9(m)，6.7(m)，7.7(m)，8.0(m)，8.8(d)。19F NMR(CD2Cl2)：-63.1(s，3F)，-63.2(s，3F)，-109.1(ddd，1F)，-109.5(ddd)。分析：计算：C，44.9；H，2.6；N，3.5。实测：C，44.4；H，2.6；N，3.3。
化合物1-w
把来自实施例4的铱羟基二聚物(0.20克)在THF(6毫升)中的溶液用50毫克三氟乙酸处理，通过短二氧化硅柱过滤，蒸发到约0.5毫升，用己烷(8毫升)处理，放置一整夜。分离黄色晶体固体，用己烷洗涤，并在真空下干燥。产率(1∶1THF溶剂化物)：0.24克(96％)。19F NMR(CD2Cl2，20℃)，δ：-63.2(s，3F)，-76.4(s，3F)，-107.3(ddd，1F)。1H NMR(CD2Cl2，20℃)，δ：9.2(br s，1H)，8.2(dd，1H)，8.1(d，1H)，7.7(m，1H)，6.7(m，1H)，5.8(dd，1H)，3.7(m，2H，THF)，1.8(m，2H，THF)。
化合物1-x
把三氟乙酸酯中间体即化合物1-w(75毫克)和2-(4-溴甲基)-5-溴代吡啶(130毫克)在150-155℃在N2下搅拌30分钟。把所得的固体冷却到室温并溶解在CH2Cl2中。所得的溶液通过硅胶过滤并蒸发。把残渣用温热的己烷洗涤数次并在真空下干燥，留下黄色的发黄色荧光的固体。产率：74毫克(86％)。19F NMR(CD2Cl2，20℃)，δ：-63.1(s，3F)，-63.3(s，3F)，-108.8(ddd，1F)，-109.1(ddd，1F)。1H NMR(CD2Cl2，20℃)，δ：8.2(s)，7.9(m)，7.7(m)，7.0(d)，6.7(m)，6.2(dd)，6.0(dd)。该配合物是经式的，氟化配体的氮是反式的，如X-射线分析所证实的。
实施例6
本实施例说明以上第五分子式的经式-Ir(La)3的铱化合物的制备。
化合物1-s
该配合物用与化合物1-n类似的方法合成。根据NMR、TLC和TGA数据，结果是面式和经式异构体的1∶1混合物。
化合物1-t
在温度缓慢(30-40分钟)升高到165℃(油浴)过程中，把IrCl3·nH2O(54％Ir；0.40克)、2-(3，5-二氟苯基)-5-三氟甲基吡啶(1.40克、AgOCOCF3(0.81克)和水(0.5毫升)的混合物在N2流下剧烈搅拌。在165℃下40分钟后，该混合物凝固。把该混合物冷却到室温。把固体用二氯甲烷萃取直至萃取物脱色。把混合的二氯甲烷溶液通过短二氧化硅柱过滤并蒸发。残渣用己烷充分洗涤，并在真空下干燥。产率：0.53克(49％)。19F NMR(CD2Cl2，20℃)，δ：-63.55(s，3F)，-63.57(s，3F)，-63.67(s，3F)，-89.1(t，1F)，-100.6(t，1F)，-102.8(dd，1F)，-118.6(ddd，1F)，-119.3(ddd，1F)，-123.3(ddd，1F)。1H NMR(CD2Cl2，20℃)，δ：8.4(s)，8.1(m)，7.9(m)，7.6(s)，7.5(m)，6.6(m)，6.4(m)。该配合物是经式的，如还用X-射线分析所证实的。
化合物1-u
与化合物1-q类似地制备并分离该配合物，然后通过从1，2-二氯乙烷-己烷中结晶进行提纯。提纯产物的产率为53％。按照NMR数据，该配合物是经式的。19F NMR(CD2Cl2，20℃)，δ：-63.48(s，3F)，-63.52(s，6F)，-105.5(ddd，1F)，-105.9(ddd，1F)，-106.1(ddd，1F)，-107.4(t，1F)，-107.9(t，1F)，-109.3(t，1F)。1H NMR(CD2Cl2，20℃)，δ：8.6(m)，8.3(s)，8.2(s)，8.1(m)，7.9(m)，7.6(m)，6.6(m)，6.4(m)，6.0(m)，5.8(m)。
化合物1-v
使用三氟乙酸酯二环金属化中间体化合物1-x和2-(4-氟代苯基)-5-三氟甲基吡啶，用与化合物1-w类似的方法制备该经式配合物。19F NMR(CD2Cl2，20℃)，δ：-63.30(s，3F)，-63.34(s，3F)，-63.37(s，3F)，-108.9(ddd，1F)，-109.0(ddd，1F)，-109.7(ddd，1F)。1HNMR(CD2Cl2，20℃)，δ：8.3-7.6(m)，6.7(m)，6.6(dd)，6.3(dd)，6.0(dd)。在1大气压升华时，这种发黄色荧光的经式配合物异构化成绿色荧光面式异构体化合物1-b。
实施例7
该实施例说明使用本发明的铱配合物形成OLED。
通过热蒸发技术制备包括空穴传输层(HT层)、电致发光层(EL层)和至少一个电子传输层(ET层)的薄膜OLED器件。使用带有油扩散泵的Edward Auto 306蒸发器。所有薄膜沉积的基础真空在10-6乇范围内。该沉积室能够沉积5种不同的薄膜而不需要中断真空。
使用氧化铟锡(ITO)涂敷的玻璃基质，ITO涂层约1000-2000埃。该基质首先用1N的HCl溶液腐蚀掉不想要的ITO区域形成图案，以形成第一种电极图案。使用聚酰亚胺代作为掩模。形成图案的ITO基质然后在洗涤剂水溶液中超声波清洗。然后把该基质用蒸馏水漂洗，然后用异丙醇漂洗，然后在甲苯蒸气中脱脂～3小时。
然后把清洗且形成图案的ITO基质装入真空室中，并把该真空室抽真空到10-6乇。然后把该基质用氧等离子体进一步清洗约5-10分钟。在清洗后，通过热蒸发依次向该基质上沉积多层薄膜。最后，通过掩模沉积有图案的Al金属电极。在沉积过程中使用石英晶体监测器(Sycon STC-200)测定薄膜的厚度。在实施例中报告的所有薄膜厚度是标称的，假定沉积的材料密度相同来计算的。然后把制成的OLED器件取出真空室并立即表征而没有包封。
器件层和厚度总结在表6中。在所有情况下，阳极是如上讨论的ITO，阴极是厚度为700-760埃的Al。在一些样品中，使用两层电子传输层。先表示的层靠近EL层施加。
通过测定其(1)电流-电压(I-V)曲线、(2)电致发光辐射率与电压的关系和(3)电致发光光谱与电压的关系来表征OLED样品。所用的设备200如图2所示。OLED样品220的I-V曲线用Keithley Source-Measurement Unit Model 237，280测定。用Minolta LS-110光度仪测定电致发光辐射率(用Cd/m2的单位表示)与电压的关系，并使用Keithley SMU扫描电压。使用一对透镜230聚集光，通过电子快门240，并通过光谱仪250分散，然后用二极管阵列检测器260测定，获得电致发光光谱。所有这三种测量同时进行并用计算机270控制。用LED的电致发光辐射率除以运行该器件所需的电流密度，测定在某一电压下的器件效率。其单位是Cd/A。
结果在下表7中给出：
Figure C0181486100401
Figure C0181486100411
峰值效率是器件中电致发光化合物价值的最好表示。它给出为了获得某一光子数的输出(辐射率)必须向器件中输入多少电子的量度。它是一个根本的重要参数，其反映发光材料的固有效率。它对于实际应用也是重要的，因为更高的效率意味着为了获得相同的辐射率需要更少的电子，这又意味着更低的功率消耗。更高效率的器件往往还有更长的寿命，因为更高比例的注入电子被转变成光子，而不是产生热量或者导致不希望的化学副反应。大多数本发明的铱配合物具有比母体面式-三(2-苯基吡啶)铱配合物远远更高的峰值效率。具有更低效率的那些配合物作为磷光或荧光材料或者作为催化剂也发现了实用性，如以上所讨论的。

Claims (21)

1.一种包含发射层的有机电子器件，该发射层包含至少一种具有以下分子式的铱化合物：
IrLaLbLc xL’yL”z
这里：
x＝0或1，y＝0、1或2，且z＝0或1，条件是：
x＝0或y+z＝0且
当y＝2时，则z＝0；
L’＝二齿配体或单齿配体，并且不是苯基吡啶、苯基嘧啶或苯基喹啉；条件是：
当L’为单齿配体时，y+z＝2，且
当L’为二齿配体时，z＝0；
L”＝单齿配体，并且不是苯基吡啶、和苯基嘧啶或苯基喹啉；且
La、Lb和Lc彼此相同或不同并且La、Lb和Lc的每一个具有以下结构(I)：
Figure C018148610002C1
其中：
相邻的R1-R4和R5-R8对任选结合形成5元或6元环，
R1-R8的至少一个选自F、CnF2n+1、OCnF2n+1和OCF2X，这里，n＝1-6且X＝H、Cl或Br，并且
A＝C或N，条件是当A＝N时，没有R1，
其中，该铱化合物以该发射层重量的至少20％的量存在。
2.权利要求1的器件，其中，x＝1，y＝0且z＝0。
3.权利要求2的器件，其中，A＝C且R1-R8中没有一个选自硝基。
4.权利要求1的器件，其中，R3是CF3。
5.权利要求4的器件，其中，R5-R8的至少之一选自F、CnF2n+1、OCnF2n+1和OCF2X，这里，n＝1-6且X＝H、Cl或Br。
6.权利要求2的器件，其中，A＝C，R3＝CF3，R7＝F，且R1、R2、R4-R6和R8＝H。
7.权利要求2的器件，其中，A＝C，R3和R6＝CF3，且R1、R2、R4、R5、R7和R8＝H。
8.权利要求2的器件，其中，A＝C，R3＝CF3，R6和R8＝F，且R1、R2、R4、R5和R7＝H。
9.权利要求1的器件，其中，x＝0且y＝1，具有以下结构(VI)：
Figure C018148610003C1
10.一种包含发射层的有机电子器件，其中，发射层包含稀释剂和小于20重量％的至少一种具有以下第二分子式的化合物：
IrLaLbL’yL”z    (第二分子式)
其中：
y＝0、1或2，且z＝0或1，条件是：
当y＝2时，z＝0；
L’＝二齿配体或单齿配体，并且不是苯基吡啶、苯基嘧啶或苯基喹啉；条件是：
当L’为单齿配体时，y+z＝2，且
当L’为二齿配体时，z＝0；
L”＝单齿配体，并且不是苯基吡啶、和苯基嘧啶或苯基喹啉；且
La和Lb彼此相同或不同并且La和Lb的每一个具有以下结构(I)：
Figure C018148610004C1
其中：
相邻的R1-R4和R5-R8对任选结合形成5元或6元环，
R1-R8的至少之一选自F、CnF2n+1、OCnF2n+1和OCF2X，这里，n＝1-6且X＝H、Cl或Br，且
A＝C或N，条件是当A＝N时，没有R1。
11.权利要求10的器件，其中，稀释剂选自聚(N-乙烯基咔唑)、聚硅烷、4，4’-N，N’-二咔唑联苯和叔芳胺。
12.权利要求1的器件，其还包含空穴传输层，选自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)、三苯基胺(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]吡唑啉(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)、卟啉化合物及其组合。
13.权利要求1的器件，其还包含选自三(8-羟基氢醌)铝、2，9-二甲基-4，7-二苯基-1，10-菲咯啉(DDPA)、4，7-二苯基-1，10-菲咯啉(DPA)、2-(4-联苯基)-5-(4-叔丁基苯基)-1，3，4-噁二唑(PBD)、3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1，2，4-三唑(TAZ)及其组合的电子传输层。
14.一种具有选自面式-Ir(L)3和经式-Ir(L)3的分子式的化合物，其中，L选自下列的基团1-a到1-m和1-q到1-v，并且具有以下结构(I)：
Figure C018148610005C1
  化合物   A   R<sub>1</sub>   R<sub>2</sub>   R<sub>3</sub>   R<sub>4</sub>   R<sub>5</sub>   R<sub>6</sub>   R<sub>7</sub>   R<sub>8</sub>   分子式 1-a C H H CF<sub>3</sub> H H H H H 第四 1-b C H H CF<sub>3</sub> H H H F H 第四   1-c   C   H   H   CF<sub>3</sub>   H   F   H   H   H   第四   1-d   C   H   H   H   H   F   H   H   H   第四   1-e   C   H   H   CF<sub>3</sub>   H   H   CF<sub>3</sub>   H   H   第四   1-f   C   H   H   H   H   H   CF<sub>3</sub>   H   H   第四   1-g   C   H   H   H   H   H   H   F   H   第四   1-h   C   Cl   H   CF<sub>3</sub>   H   H   H   H   H   第四   1-i   C   H   H   CF<sub>3</sub>   H   H   H   OCH<sub>3</sub>   H   第四   1-j   C   H   H   CF<sub>3</sub>   H   H   F   H   H   第四   1-k   C   H   H   NO<sub>2</sub>   H   H   CF<sub>3</sub>   H   H   第四   1-l   C   H   H   CF<sub>3</sub>   H   H   H   OCF<sub>3</sub>   H   第四 1-m N -- CF<sub>3</sub> H H H H F H 第四   1-q   C   H   H   CF<sub>3</sub>   H   H   OCH<sub>3</sub>   H   H   第四
Figure C018148610005C2
15.一种具有选自以下结构(IV)、(V)、(VI)、(IX)和(X)的结构的化合物：
Figure C018148610007C1
16.一种包含发射层的有机电子器件，该发射层包含一种选自以下(i)和(ii)的化合物：
(i)一种具有选自面式-Ir(L)3和经式-Ir(L)3的分子式的化合物，其中，L是选自下列的1-a到1-m和1-q到1-v的基团，并且具有以下结构(I)：
Figure C018148610008C1
(ii)具有以下结构(IV)、(V)、(VI)、(IX)和(X)之一的化合物：
Figure C018148610008C2
  化合物   A   R<sub>1</sub>   R<sub>2</sub>   R<sub>3</sub>   R<sub>4</sub>   R<sub>5</sub>   R<sub>6</sub>   R<sub>7</sub>   R<sub>8</sub>   分子式   1-a   C   H   H   CF<sub>3</sub>   H   H   H   H   H   第四 1-b C H H CF<sub>3</sub> H H H F H 第四   1-c   C   H   H   CF<sub>3</sub>   H   F   H   H   H   第四   1-d   C   H   H   H   H   F   H   H   H   第四   1-e   C   H   H   CF<sub>3</sub>   H   H   CF<sub>3</sub>   H   H   第四   1-f   C   H   H   H   H   H   CF<sub>3</sub>   H   H   第四   1-g   C   H   H   H   H   H   H   F   H   第四   1-h   C   Cl   H   CF<sub>3</sub>   H   H   H   H   H   第四   1-i   C   H   H   CF<sub>3</sub>   H   H   H   OCH<sub>3</sub>   H   第四   1-j   C   H   H   CF<sub>3</sub>   H   H   F   H   H   第四   1-k   C   H   H   NO<sub>2</sub>   H   H   CF<sub>3</sub>   H   H   第四 1-l C H H CF<sub>3</sub> H H H OCF<sub>3</sub> H 第四   1-m   N   --   CF<sub>3</sub>   H   H   H   H   F   H   第四   1-q   C   H   H   CF<sub>3</sub>   H   H   OCH<sub>3</sub>   H   H   第四
17.权利要求16的器件，其中，发射层还包含稀释剂。
18.权利要求17的器件，其中，稀释剂选自聚(N-乙烯基咔唑)、聚硅烷、4，4’-N，N’-二咔唑联苯和叔芳胺。
19.一种化合物，其选自下列的2-a到2-d、2-f到2-r、2-t到2-w，以及2-y到2-aa的化合物，具有以下结构(II)：
Figure C018148610011C1
  化合物   A   R<sub>1</sub>  R<sub>2</sub>   R<sub>3</sub>   R<sub>4</sub>   R<sub>5</sub>   R<sub>6</sub>   R<sub>7</sub>   R<sub>8</sub>   R<sub>9</sub>   2-a   C   H  H   CF<sub>3</sub>   H   F   H   H   H   H   2-b   C   H  H   CF<sub>3</sub>   H   H   CF<sub>3</sub>   H   H   H   2-c   C   H  H   NO<sub>2</sub>   H   H   CF<sub>3</sub>   H   H   H   2-d   C   H  H   CF<sub>3</sub>   H   H   F   H   H   H   2-e   C   H  H   CF<sub>3</sub>   H   H   H   CH<sub>3</sub>O   H   H   2-f   C   Cl  H   CF<sub>3</sub>   H   H   H   H   H   H   2-g   C   H  H   H   CH<sub>3</sub>   H   H   F   H   H   2-h   N   --  H   H   H   H   H   F   H   H   2-i   C   H  H   CF<sub>3</sub>   H   H   H   CF<sub>3</sub>O   H   H   2-j   N   --  CF<sub>3</sub>   H   H   F   H   H   H   H   2-k   C   H  H   CF<sub>3</sub>   H   H   H   F   H   H 2-l C CF<sub>3</sub> H H H H H H H H   2-m   C   Cl  H   CF<sub>3</sub>   H   H   H   F   H   H   2-n   C   CF<sub>3</sub>  H   H   H   H   H   F   H   H   2-o   C   CF<sub>3</sub>  H   H   H   H   H   CH<sub>3</sub>O   H   H 2-p C Cl H CF<sub>3</sub> H H H CH<sub>3</sub>O H H
Figure C018148610011C2
20.一种具有以下结构VII的化合物：
Figure C018148610012C1
其中：
B＝H、CH3或C2H5；
La、Lb、Lc和Ld彼此相同或不同；并且
La、Lb、Lc和Ld的每一个具有以下结构(I)：
Figure C018148610012C2
其中：
相邻的R1-R4和R5-R8对任选结合形成5元或6元环，
R1-R8的至少一个选自F、CnF2n+1、OCnF2n+1和OCF2X，这里，n＝1-6且X＝H、Cl或Br，并且
A＝C或N，条件是当A＝N时，没有R1。
21.权利要求20的化合物，其中：
La＝Lb＝Lc＝Ld；
B＝H；
R3＝CF3；
R7＝F；
R1、R2、R4-R6和R8＝H。
CNB018148611A 2000-06-30 2001-06-27 含有氟化苯基吡啶、苯基嘧啶和苯基喹啉的电致发光铱化合物及用该化合物制备的器件 Expired - Lifetime CN100438123C (zh)

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Patentee after: LG CHEM, Ltd.

Address before: Wilmington, Delaware, USA

Patentee before: E. I. du Pont de Nemours and Co.

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Granted publication date: 20081126

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