CN101878279B - 含甲亚胺金属配合物的有机电致发光器件 - Google Patents

含甲亚胺金属配合物的有机电致发光器件 Download PDF

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CN101878279B
CN101878279B CN200880115344.XA CN200880115344A CN101878279B CN 101878279 B CN101878279 B CN 101878279B CN 200880115344 A CN200880115344 A CN 200880115344A CN 101878279 B CN101878279 B CN 101878279B
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埃米尔·侯赛因·帕勒姆
乔纳斯·瓦伦丁·克罗巴
安雅·格哈德
罗科·福特
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Abstract

本发明涉及发磷光的有机电致发光器件，它包含式(I)的金属配合物作为发射层的基质材料。

Description

含甲亚胺金属配合物的有机电致发光器件
在例如US4539507、US5151629、EP0676461和WO98/27136中描述了其中使用有机半导体作为功能材料的有机电致发光器件(OLED)的结构。近年来，表现出磷光而不是荧光的有机金属配合物使用得越来越多(M.A.Baldo等，Appl.Phys.Lett.1999，75，4-6)。由于量子-力学原因，使用有机金属化合物作为磷光发光体，有可能获得高达4倍的能量和电能效率的提高。通常，在显示出三线态发射的OLED中仍存在相当多的问题。例如，对于在高质量和长寿命电致发光器件中使用三线态发射体来说，磷光OLED的物理性质在效率、操作电压和寿命方面仍然不令人满意。
根据现有技术，通常使用4，4′-双(N-咔唑基)联苯(CBP)作为磷光OLED中的基质材料。缺点是用其生产的器件的寿命短和操作电压高，这导致了低的电能效率。此外，CBP的玻璃态转变温度不够高。尽管CBP具有所有这些缺点，但它仍然继续用作三线态基质材料，因为使用其它基质材料上述问题也还不能获得令人满意的解决。
此外，已知铝配合物，特别是B-Alq，被用作三线态基质材料(例如Chem.Phys.Lett.2005，404，121-125)。
US2006/040139描述了使用带有基于希夫碱的配体的金属配合物作为用于光敏材料的主体材料。但是，只公开了五或六配位的含有三价金属的配合物，特别是铝配合物。
本发明的目的是提供三线态基质材料，它具有足够高的玻璃态转变温度和非常良好的热稳定性，并且对水解稳定，与现有技术相比，在有机电致发光器件中产生改进的效率、寿命和操作电压。
令人吃惊的是，现在已发现，某些具有二价金属离子、其中配体通过两个亚胺氮原子与金属配位的金属螯合配合物表现出显著的改进，特别是在寿命、效率、对温度应力的稳定性、玻璃态转变温度和水解稳定性方面。这些配合物也可以是二聚体的形式，含有在四方-平面、四面体或准四面体配位中处于氧化态+II的四配位的金属离子。因此，本发明涉及在发射层中含有这些配合物作为基质材料的磷光电致发光器件。
因此，本发明涉及在发射层中含有至少一种磷光化合物和至少一种式(I)的化合物的有机电致发光器件
式(I)
其中使用的符号和下标含义如下：
M每次出现时，相同或不同地是处于氧化态+II的金属离子，选自Be、Mg、Ca、Sr、Ba、Fe、Ru、Os、Co、Ni、Pd、Cu、Zn、Cd、Hg、Sn和Pb；
X每次出现时，相同或不同地是O、S或CO-O；
Ar1是具有5到60个芳香性环原子的芳香性或杂芳香性环体系，其可以被一个或多个基团R取代，其中单独的芳香基团可以通过具有1到10个C原子的亚烷基彼此相连，此外，其中一个或多个非相邻的C原子可以被O或S替代；
Ar2每次出现时，相同或不同地是具有5到60个芳香环原子的芳香性或杂芳香性环体系，其可以被一个或多个基团R取代；
Y每次出现时，相同或不同地是单键或具有1到10个C原子的亚烷基，此外，其中一个或多个非相邻的、没有与氮成键的C原子可以被O替代，并且可以被一个或多个基团R取代；
R每次出现时，相同或不同地是H，F，Cl，Br，I，N(R2)2，CN，NO2，Si(R2)3，B(OR2)2，C(＝O)R2，P(＝O)(R2)2，S(＝O)R2，S(＝O)2R2，OSO2R2，具有1到40个C原子的直链烷基、烷氧基或硫代烷基，或具有3到40个C原子的支链或环状烷基、烷氧基或硫代烷基，它们各自可以被一个或多个基团R2取代，其中一个或多个非相邻的CH2基团可以被R2C＝CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C＝O、C＝S、C＝Se、C＝NR2、P(＝O)(R2)、SO、SO2、NR2、O、S或CONR2替代，并且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2替代，或具有5到60个芳香环原子的芳香性或杂芳香性环体系，它们各自可以被一个或多个基团R2取代，或具有5到60个芳香环原子的芳氧基或杂芳氧基，它们可以被一个或多个基团R2取代，或这些体系的组合；在这里，两个或多个取代基R也可以彼此形成单环或多环脂族或芳香性环体系；
R1每次出现时，相同或不同地是H，F，CF3，具有1到40个C原子的直链烷基，或具有3到40个C原子的支链或环状烷基，它们各自可以被一个或多个基团R2取代，其中一个或多个非相邻的CH2基团可以被R2C＝CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2替代，并且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2替代，或具有5到60个芳香性环原子的芳香性或杂芳香性环体系，它们各自可以被一个或多个基团R2取代，或这些体系的组合；在这里，R1也可以与一个或多个取代基R形成单环或多环脂族或芳香性环体系；
R2每次出现时，相同或不同地是H、F或具有1到20个C原子的脂族、芳香族或杂芳族烃类基团，此外，其中一个或多个H原子可以被F取代；在这里，两个或多个取代基R2也可以彼此形成单环或多环脂族或芳香性环体系；
n每次出现时，相同或不同地是0、1或2。
式(I)的化合物优选具有高于100℃、特别优选高于120℃的玻璃态转变温度Tg。
出于本发明的目的，磷光化合物是指从具有较高自旋多重性、即自旋态＞1的激发态，特别是从激发三线态发光的化合物。这里的发射可以从纯的三线态或从有三线态参与的混合态发生。出于本发明的目的，任何从铱或铂配合物的发光被当作是指磷光。
出于本发明的目的，芳基含有6到40个C原子；出于本发明的目的，杂芳基含有2到40个C原子和至少一个杂原子，前提是C原子和杂原子的总和至少为5。杂原子优选选自N、O和S。这里的芳基和杂芳基是指简单的芳香性环，即苯，或简单的杂芳香性环，例如吡啶、嘧啶、噻吩，或缩合的芳基或杂芳基，例如萘、蒽、菲、喹啉、异喹啉。
出于本发明的目的，芳环体系在环体系中包含6到40个C原子。出于本发明的目的，杂芳环体系在环体系中包含2到40个C原子和至少一个杂原子，前提是C原子和杂原子的总和至少为5。杂原子优选选自N、O和S。出于本发明的目的，芳环或杂芳环体系被认为是指无需仅包含芳基或杂芳基的体系，而是其中多个芳基或杂芳基也可以被非芳香性单元(非H原子优选少于10％)间断，例如sp3-杂化的C、N或O原子。因此，例如，出于本发明的目的，体系例如9，9′-螺二芴、9，9-二芳基芴、三芳基胺、二芳基醚、芪，也被当作芳环体系，以及类似的其中两个或多个芳基被例如直链或环状烷基或被甲硅烷基间断的体系。
出于本发明的目的，其中单独的H原子或CH2基团可以另外被上面提到的基团取代的C1-到C40-烷基，优选是指下列基团：甲基，乙基，正丙基，异丙基，正丁基，异丁基，仲丁基，叔丁基，2-甲基丁基，正戊基，仲戊基，环戊基，正己基，环己基，正庚基，环庚基，正辛基，环辛基，2-乙基己基，三氟甲基，五氟乙基，2，2，2-三氟乙基，乙烯基，丙烯基，丁烯基，戊烯基，环戊烯基，己烯基，环己烯基，庚烯基，环庚烯基，辛烯基，环辛烯基，乙炔基，丙炔基，丁炔基，戊炔基，己炔基，庚炔基或辛炔基。C1-到C40-烷氧基优选是指甲氧基，三氟甲氧基，乙氧基，正丙氧基，异丙氧基，正丁氧基，异丁氧基，仲丁氧基，叔丁氧基或2-甲基丁氧基。具有5到40个芳环原子的芳环或杂芳环体系，其在每种情况下也可以被上面提到的基团R取代，并且其可以经任何所希望的位置与芳环或杂芳环体系相连，尤其是指源自于下列的基团：苯，萘，蒽，菲，芘，屈，苯并蒽，二萘嵌苯，荧蒽，苯并荧蒽，并四苯，并五苯，苯并芘，二苯并蒽，联苯，联苯撑，三联苯，亚三联苯，芴，螺二芴，二氢菲，二氢芘，四氢芘，顺式或反式茚并芴，顺式或反式单苯并茚并芴，顺式或反式二苯并茚并芴，三聚茚，异三聚茚，螺三聚茚，螺异三聚茚，呋喃，苯并呋喃，异苯并呋喃，二苯并呋喃，噻吩，苯并噻吩，异苯并噻吩，二苯并噻吩，吡咯，吲哚，异吲哚，咔唑，吡啶，喹啉，异喹啉，吖啶，菲啶，苯并-5，6-喹啉，苯并-6，7-喹啉，苯并-7，8-喹啉，吩噻嗪，吩噁嗪，吡唑，吲唑，咪唑，苯并咪唑，萘并咪唑，菲并咪唑，吡啶并咪唑，吡嗪并咪唑，喹喔啉并咪唑，噁唑，苯并噁唑，萘并噁唑，蒽并噁唑，菲并噁唑，异噁唑，1，2-噻唑，1，3-噻唑，苯并噻唑，哒嗪，苯并哒嗪，嘧啶，苯并嘧啶，喹喔啉，1，5-二氮杂蒽，2，7-二氮杂芘，2，3-二氮杂芘，1，6-二氮杂芘，1，8-二氮杂芘，4，5-二氮杂芘，4，5，9，10-四氮杂芘，吡嗪，吩嗪，吩噁嗪，吩噻嗪，荧红环，萘啶，氮杂咔唑，苯并咔啉，菲咯啉，1，2，3-三唑，1，2，4-三唑，苯并三唑，1，2，3-噁二唑，1，2，4-噁二唑，1，2，5-噁二唑，1，3，4-噁二唑，1，2，3-噻二唑，1，2，4-噻二唑，1，2，5-噻二唑，1，3，4-噻二唑，1，3，5-三嗪，1，2，4-三嗪，1，2，3-三嗪，四唑，1，2，4，5-四嗪，1，2，3，4-四嗪，1，2，3，5-四嗪，嘌呤，蝶啶，中氮茚和苯并噻二唑。
在本发明的优选实施方案中，金属M选自Be、Mg、Pd、Zn或Cd。金属M特别优选为Zn。
此外，下标n优选＝0或1。下标n特别优选为0。
此外，符号Y每次出现时相同或不同地优选表示单键或C(R)2基团，特别优选表示单键。
此外，符号X每次出现时相同或不同地优选表示O或S，特别优选表示O。
特别优选的是式(I)的化合物，其中上面提到的优选情况同时存在，即在化合物中，金属M选自Be、Mg、Pd、Zn或Cd，其中下标n＝0或1，并且其中符号Y每次出现时相同或不同地表示单键或C(R)2基团，其中符号X每次出现时相同或不同地表示O或S。非常特别优选的是式(I)的化合物，其中金属M是Zn，其中下标n＝0，并且其中符号Y表示单键，其中符号X表示O。
此外，对于n＝0的情况，符号Ar1优选表示具有5到24个芳环原子的芳环或杂芳环体系，它们各自可以被一个或多个基团R取代。对于n＝0的情况，基团Y-Ar1-Y特别优选表示下列式(II)到(XV)的基团：
此外，对于n＝1的情况，符号Ar1优选表示具有5到24个芳环原子、特别是具有6到12个芳环原子的芳环或杂芳环体系，它们各自可以被一个或多个基团R取代。对于n＝1的情况，符号Ar1尤其优选表示下列式(XVI)到(XXI)的基团：
在每种情况下，在式(II)到(XXI)中的虚线键表示与亚胺氮的连接。式(XIX)中的下标m是1到10。
特别优选的是这样的式(I)的化合物，其中同时具有上面提到的对于M、n、Y和X以及选自上面描述的式(II)到(XXI)的基团Ar1的优选情况。
此外，符号Ar2每次出现时相同或不同地优选表示具有5到16个芳香性环原子的芳基或杂芳基，它可以被一个或多个基团R取代。符号Ar2每次出现时相同或不同地特别优选表示选自下列的芳基或杂芳基：苯基，1-或2-萘基，4-联苯基，1-或2-蒽基，2-或3-噻吩基，2-或3-吡咯基，2-或3-呋喃基，2-、3-或4-吡啶基，3-或4-哒嗪基，4-或5-嘧啶基，吡嗪基，2-、3-、4-、5-、6-、7-或8-喹啉基，或3-、4-、5-、6-、7-或8-异喹啉基，其各自可以被一个或多个基团R取代。非常特别优选的是苯基，1-萘基，2-萘基和4-联苯基，特别是苯基，它们各自可以被一个或多个基团R取代。
特别优选的是这样的式(I)的化合物，其同时具有上面提到的优选基团Ar2和选自上面描述的式(II)到(XXI)的基团Ar1。非常特别优选的是这样的式(I)的化合物，其中同时具有上面提到的M、n、Y、X和Ar2以及选自上面描述的式(II)到(XV)的基团Ar1的特别优选情况。
此外，符号R，每次出现时，相同或不同地优选代表H、F，N(R2)2，Si(R2)3，C(＝O)R2，P(＝O)(R2)2，具有1到10个C原子的直链烷基或具有3到10个C原子的支链或环状烷基，其各自可以被一个或多个基团R2取代，其中一个或多个非相邻的CH2基团可以被R2C＝CR2、O或S替代，一个或多个H原子可以被F替代，或具有5到16个芳香性环原子的芳基或杂芳基，它们各自可以被一个或多个基团R2取代，或这些体系的组合；在这里，两个或多个取代基R2也可以彼此形成单环或多环脂族或芳香性环体系。符号R，每次出现时，相同或不同地特别优选代表H，F，具有1到4个C原子的直链烷基或具有3到4个C原子的支链烷基，其各自可以被一个或多个基团R2取代，其中一个或多个H原子可以被F各自，或具有6到10个芳香性环原子的芳基，它们在每种情况下可以被一个或多个基团R2取代；在这里，两个或多个取代基R也可以彼此形成单环或多环脂族或芳香性环体系。
此外，符号R1每次出现时，相同或不同地优选代表H，具有1到6个C原子的直链烷基或具有3到6个C原子的支链或环状烷基，其中在每种情况下，一个或多个H原子也可以被F替代，或代表具有5到16个芳香性环原子的芳基或杂芳基，它们各自可以被一个或多个基团R2取代。符号R1每次出现时，相同或不同地特别优选代表H，甲基或苯基或萘基，它们各自可以被一个或多个基团R2取代。
式(I)的化合物可以任选采取固态二聚体或寡聚体的形式，而不是必须采取简单配合物的形式，如式(I)中以简化形式所描述的。因此，含有采用二聚体或寡聚体形式的式(I)化合物的有机电致发光器件，以与含有简单配合物形式的式(I)化合物的电致发光器件相同的方式，自然包括在本发明内。
此外，优选对称化合物，即其中所有的符号Ar2都相同，所有的符号X都相同，所有的符号R1都相同，所有的符号Y都相同，并且都被相同地取代的化合物。
含有式(I)的结构要素的优选化合物的例子是下面图示的化合物(1)到(180)：
式(I)的化合物可以通过有机化学标准方法来合成。这里特别适用的有两种可能的合成方法。因此，可以首先从相应的二胺和醛或酮合成配体，同时形成了希夫碱，然后使它在后续步骤中与适合的金属盐反应，得到相应的金属配合物。此外，也可以通过使二胺、醛或酮与适合的金属盐彼此同时在一个步骤中(模板合成)反应，进行配体合成和络合反应(Eur.J.Inorg.Chem.2004，4561-65)。
式(I)的化合物用于在有机电致发光器件的发射层中作为用于磷光发射体的基质材料。
因此，本发明此外还涉及式(I)的化合物在有机电致发光器件中作为用于磷光化合物的基质材料的用途。
有机电致发光器件包含阴极、阳极和至少一个发射层。除了这些层之外，它还可以包含其它层，例如在每种情况下一个或多个空穴注入层，空穴传输层、电子阻挡层、空穴阻挡层、电子传输层、电子注入层、电荷产生层(IDMC2003，Taiwan；Session21OLED(5)，T.Matsumoto，T.Nakada，J.Endo，K.Mori，N.Kawamura，A.Yokoi，J.Kido，MultiphotonOrganicELDeviceHavingChargeGenerationLayer(带有电荷产生层的多光子有机EL器件))和/或有机或无机p/n结。同样，也可以将具有例如激子阻挡功能的中间层引入到两个发射层之间。但是，应该指出，这些各个层并非必须存在。
在本发明的优选实施方案中，包含式(I)化合物和磷光发射体的发射层是红、绿或蓝光发射层。
在本发明进一步优选的实施方案中，有机电致发光器件包含多个发射层，其中至少一个层包含至少一种式(I)的化合物和至少一种磷光化合物。特别优选的情况下，发射层在380nm～750nm之间总计具有众多发射最大值，总体产生了白色发射，即在发射层中使用了各种不同的能够发射荧光或磷光的发射化合物。特别优选的是这样的三层体系，其中所述的三层表现出蓝色、绿色和橙色或红色的发射(基本结构，例如参见WO05/011013)。
磷光化合物(＝三线态发射体)包含至少一种如下化合物，该化合物在适当激发下优选在可见光区域发射光，此外还包含至少一个原子序数大于20，优选大于38并小于84，特别优选大于56并小于80的原子。使用的磷光发射体优选是包含铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物，特别是含有铱或铂的化合物。
特别优选的有机电致发光器件包含至少一种式(XXII)到(XXV)的化合物作为磷光发射体
其中R具有与上面对于式(I)描述定义相同的含义，使用的其它符号意义如下：
DCy每次出现时，相同或不同地是这样的环状基团，所述环状基团包含至少一个供体原子，优选为氮、碳烯形式的碳或磷，环状基团通过所述供体原子与金属键合，并且所述供体原子反过来可以带有一个或多个取代基R；基团DCy和CCy通过共价键彼此相连；
CCy每次出现时，相同或不同地是这样的环状基团，所述环状基团包含碳原子，环状基团通过所述碳原子与金属键合，并且所述碳原子可以反过来带有一个或多个取代基R；
A每次出现时，相同或不同地是单阴离子、二齿螯合配体，优选为二酮化物(diketonate)配体。
多个基团R之间环体系的形成也可以在基团DCy和CCy之间产生桥接。
上面描述的发射体的例子公开在专利申请WO00/70655，WO01/41512，WO02/02714，WO02/15645，EP1191613，EP1191612，EP1191614和WO05/033244中。一般来说，适合的磷光配合物都是在现有技术中用于磷光OLED的磷光配合物，并且它们对于有机光致发光技术领域的本领域技术人员来说是公知的。
基于发射体和基质材料的整个混合物计，至少一种式(I)的化合物与至少一种磷光发射体的混合物含有1到99wt％，优选2到90wt％，特别优选3到40wt％，特别是5到15wt％的至少一种磷光发射体。相应地，基于发射体和基质材料的整个混合物计，混合物含有99到1wt％，优选98到10wt％，特别优选97到60wt％，特别是95到85wt％的至少一种式(I)的基质材料。除了式(I)的基质材料之外，整个混合物还可以含有其它基质材料。
此外，优选这样的有机电致发光器件，其特征在于利用升华工艺方法施加一个或多个层，其中在真空升华装置中，在低于10-5mbar、优选低于10-6mbar的压力下气相沉积所述材料。
同样，优选这样的有机电致发光器件，其特征在于通过OVPD(有机气相沉积)方法或借助于载气升华施加一个或多个层，其中在10-5mbar～1bar的压力下施加所述材料。这种方法的一个具体例子是OVJP(有机气相喷印)方法，其中通过喷嘴直接施加材料并从而被构建(例如M.S.Arnold等，Appl.Phys.Lett.2008，92，053301)。
此外，优选这样的有机电致发光器件，其特征在于通过例如旋涂或利用任何所需的印刷方法从溶液产生一个或多个层，这些印刷方法例如丝网印刷，柔性版轮转印刷或胶版印刷，但是特别优选LITI(光诱导的热成像，热转移印刷)或喷墨印刷。为此目的需要可溶性化合物。
这些方法对于本领域技术人员来说一般是公知的，可以由他毫无问题地施加到本发明的含有式(I)化合物和三线态发射体的体系中。
式(I)的化合物在用于有机电致发光器件中时，与现有技术相比具有下列令人吃惊的优点：
1.在使用式(I)的化合物时，与B-Alq和其它铝配合物相比，操作电压明显降低，这导致显著更高的电能效率。
2.在使用式(I)的化合物作为三线态基质材料时，器件的寿命也增加了。
3.此外，在使用式(I)的化合物作为三线态基质材料时，器件的效率增加了。
4.式(I)的化合物与在现有技术中通常用作三线态基质材料的CBP相比，具有明显更高的玻璃态转变温度。
上面提到的这些优点没有伴随对其它电子性质的损害。
通过下面的实施例对本发明进行更详细地解释，不希望本发明受到这些实施例的限制。
实施例：
除非另有指明，否则下面的合成都在无水溶剂中，在保护性气体环境下进行。起始材料可以从ALDRICH购买，或可以通过从文献已知的工艺方法进行制备。从2，2′-二硝基联苯合成2，2′-二氨基联苯，按照在Chem.Commun.2005，46，5799-5801中描述的工艺方法进行。4，4′-二溴-2，2′-二硝基联苯的合成描述在J.Am.Chem.Soc.2006，128，9034-9035中。2-巯基苯甲醛的合成描述在Synlett2001，1956-1958中。
实施例1：3′，2″-二氨基-对四联苯的合成
a)制备3′，2″-二硝基-对四联苯
将2.4g(2.1mmol)Pd(PPh3)4添加到18.8g(154.5mmol)苯基硼酸、30g(74.6mmol)2，5-二溴硝基苯和53g(212.7mmol)碳酸钾在300ml水和300mlTHF的混合物中的充分搅拌的脱气悬浮液中，将混合物回流加热20小时。冷却后，分离出有机相，用200ml水清洗3次，用200ml饱和氯化钠溶液清洗一次，在硫酸镁上干燥，并在旋转蒸发器中真空蒸发至干燥。将灰色残余物从己烷重结晶。使用抽吸将沉积的晶体过滤出来，用少量MeOH洗涤，在真空中干燥；产率：23g，理论产率的80％；纯度：根据HPLC为99.2％。
b)3′，2″-二氨基-对四联苯的制备
将16.6g(42mmol)3′，2″-二硝基-对四联苯和1.99gPd/C(10％)悬浮在200ml甲醇中，分步加入8.4g(222mmol)硼氢化钠，同时在0℃搅拌。在搅拌2小时后，将澄清的溶液用稀HCl中和。然后除去溶剂，将残余物用水充分洗涤，从二噁烷重结晶。将沉淀过滤，在真空中干燥，得到11g(35.6mmol)结晶固体。总产率为78％。
实施例2：金属配合物的通用合成步骤
制备配合物有两种通用方法：
A)将芳香胺与金属盐和邻羟基醛或邻羟基酮反应；
B)将芳香胺的希夫碱与金属盐反应。
如果副产物(H2O)不破坏待制备的配合物，可以使用方法A。如果该配合物对水分敏感，或如果亚胺的形成不定量，方法B是适合的。
方法A：通用合成步骤
将260mmol邻羟基醛或邻羟基酮添加到121mmol芳香二胺在1000ml无水甲醇和100ml三乙基胺的溶液中。然后向混合物中加入127mmol金属盐，例如乙酸锌，将它在室温搅拌24小时，然后过滤并用冷甲醇洗涤。产品通过重结晶纯化。
方法B：通用合成步骤
i)配体合成
配体合成使用共沸蒸馏移除形成的水来进行。将300ml无水甲苯在带有三颈烧瓶、搅拌器、内部温度计和滴液漏斗的蒸馏装置中加热至沸腾。然后缓慢地滴加60mmol芳香胺在50ml无水甲苯中的溶液和120mmol醛或酮在50ml甲苯中的溶液。向混合物加入催化量的对甲苯磺酸。蒸馏一直进行到出现澄清、粘稠的甲苯。残余溶剂在油泵真空(130Pa)中移除。偶氮甲碱作为黄色固体分离，从甲苯重结晶，并用MeOH洗涤。
ii)配合物合成
将相应亚胺配体在100ml甲醇中的溶液(17mmol)添加到19mmol适合的金属盐溶液中，例如3.4g二水乙酸锌在100ml甲醇的溶液中，并将混合物在室温搅拌3天。过滤后，将固体在真空中干燥，然后在保护性气体下重结晶。
实施例3：Zn配合物(1)的合成
通过方法(B)进行[[2，2′-[[1，1′-联苯基]-2，2′-二基双(次氮基次甲基)]双[苯酚]](2-)-N，N′，O，O′]锌的合成，首次描述在JournaloftheChemicalSociety，DaltonTransactions：InorganicChemistry1996，2835-2838中。通过该方法获得的配合物含有作为副产物的自由配体，使得纯度＞99％的配合物的制备更加困难。上面描述的方法(A)，从400ml无水MeOH中的8.9g(48mmol)2，2′-二氨基联苯、17g(140mmol)2-羟基苯甲醛、8.8g(48mmol)二水乙酸锌和40ml三乙基胺开始，以非常高的产率得到了配合物，纯度＞99.9％。24小时后，将沉淀固体用冷甲醇洗涤，在真空中干燥，然后在保护性气体下从无水EtOH重结晶，给出21.5g(47mmol)结晶固体。总产率为98％(Tg＝152.0℃，Tm＝280.0℃)。
实施例4：Zn配合物(22)的合成
通过方法(A)，从400ml无水MeOH中的8.9g(48mmol)2，2′-二氨基联苯、24.3g(140mmol)3，4-二叔丁基-2-羟基-苯甲醛、8.8g(48mmol)二水乙酸锌和40ml三乙基胺开始合成该配合物。24小时后，将沉淀固体用冷甲醇洗涤，在真空中干燥，然后在保护性气体下从无水EtOH重结晶，给出29g(42mmol)结晶固体。总产率为96％(Tg＝170.5℃，Tm＝314.2℃)。
实施例5：Zn配合物(16)的合成
通过方法(A)，从400ml无水MeOH中的16g(48mmol)3′，2″-二氨基-对四联苯、24.3g(140mmol)2-羟基-苯甲醛、8.8g(48mmol)二水乙酸锌和40ml三乙基胺开始合成该配合物。24小时后，将沉淀固体用冷甲醇洗涤，在真空中干燥，然后在保护性气体下从无水EtOH重结晶，给出27g(44mmol)结晶固体。总产率为96％(Tg＝252.7℃，Tm＝367.6℃)。
实施例6：Zn配合物(2)的合成
该配合物通过方法(B)合成。
a)配体合成
从400ml甲苯中的11.16g(60.59mmol)2，2′-二氨基联苯、16.3g(120mmol)2-羟基乙酰苯和0.2g(1.1mmol)对甲苯磺酸进行合成。24小时后，将沉淀固体用冷甲醇洗涤，给出20g(47mmol)结晶固体。总产率为76％。
b)配合物合成
从200ml甲醇中的3.4g(19mmol)二水乙酸锌和6g(17mmol)配体进行合成。24小时后，将沉淀固体用冷甲醇洗涤，在真空中干燥，然后在保护性气体下从无水EtOH重结晶，给出6g(13.1mmol)结晶固体。总产率为86％(Tg＝143.4℃，Tm＝261.0℃)。
实施例7：Zn配合物(15)的合成
通过方法(B)合成该配合物。
a)配体合成
从400ml甲苯中的11.16g(60.59mmol)2，2′-二氨基联苯、23g(120mmol)2-羟基二苯酮和0.2g(1.1mmol)对甲苯磺酸进行合成。24小时后，将沉淀固体用冷甲醇洗涤，给出22.5g(41mmol)结晶固体。总产率为70％。
b)配合物合成
从200ml甲醇中的3.4g(19mmol)二水乙酸锌和9.2g(17mmol)配体进行合成。24小时后，将沉淀固体用冷甲醇洗涤，在真空中干燥，然后在保护性气体下从无水EtOH重结晶，给出7.5g(11mmol)结晶固体。总产率为73％(Tg＝232.8℃，Tm＝354.5℃)。
实施例8：Zn配合物(134)的合成
通过方法(A)，从400ml无水MeOH中的8.9g(48mmol)2，2′-二氨基联苯、19.3g(140mmol)2-巯基苯甲醛、8.8g(48mmol)二水乙酸锌和40ml三乙基胺开始合成该配合物。24小时后，将沉淀固体用冷甲醇洗涤，在真空中干燥，然后在保护性气体下从无水EtOH重结晶，给出22g(45mmol)结晶固体。总产率为94％(Tg＝165.5℃，Tm＝290.0℃)。
实施例9到11：含有式(I)化合物的有机电致发光器件的生产和性质
可以按照例如在WO05/003253中的描述来生产本发明的电致发光器件。在这里，对各种不同OLED的结果进行了比较。为了更好的可比性，基本结构、使用的材料、掺杂程度及其层厚度是相同的。只有发射层中的主体是不同的。第一个器件实施例描述了根据现有技术的比较标准，其中发射层由主体材料B-Alq和客体材料(掺杂物)Ir(piq)3组成。此外，描述了具有由主体材料Zn配合物(1)和客体材料(掺杂物)Ir(piq)3组成的发射层的OLED。以类似于上面提到的通用工艺方法生产具有下列结构的OLED：
空穴注入层(HIL)10nm的2，2′，7，7′-四(二-对甲苯基-氨基)螺
-9，9′-二芴
空穴传输层(HTL)30nm的NPB(N-萘基-N-苯基-4，4′-二氨基
联苯)
发射层(EML)主体材料：B-Alq(气相沉积的；来自E-Ray，
并进一步纯化，升华两次；双(2-甲基-8-喹啉
基-N1，O8)-(1，1′-联苯基-4-基)铝或CBP(
-(咔唑-9-基)联苯)作为对比或Zn配合物(1)。
掺杂物：Ir(piq)3(10％掺杂，气相沉积；按照
WO03/0068526合成)。
电子导体(ETL)20nm的AlQ3(从E-Ray购买，三(喹啉)铝
(III))
阴极1nm的LiF，顶上有150nm的Al。
为了清楚起见，Ir(piq)3的结构显示如下：
通过标准方法对这些尚未最优化的OLED进行了性质研究；为此，确定了电致发光光谱，从电流/电压/发光特征线(IUL特征线)计算的作为发光函数的效率(以cd/A为单位测量)，以及寿命。
以使用主体材料CBP生产的OLED作为对比实验，在上面描述的条件下，通常获得大约6.5cd/A的最大效率，CIE的颜色坐标为x＝0.68，y＝0.32。对于1000cd/m2的参比发光密度来说，需要6.8V的电压。在1000cd/m2的初始发光密度下，寿命为大约6000小时(参见表1)。
以使用主体材料B-Alq生产的OLED作为另一个对比实验，在上面描述的条件下，通常获得大约8.0cd/A的最大效率，CIE的颜色坐标为x＝0.68，y＝0.32。对于1000cd/m2的参比发光密度来说，需要7.5V的电压。在1000cd/m2的初始发光密度下，寿命为约7000小时(参见表1)。
相比较而言，使用主体材料Zn配合物(1)生产的本发明的OLED，使用其它都相同的结构，表现出8.5cd/A的最大效率，CIE的颜色坐标为x＝0.68，y＝0.32，其中对于1000cd/m2的参比发光密度来说，需要的电压是5.0V(参见表1)。在1000cd/m2的初始发光密度下，寿命为9000小时，明显更长，并且5.0V的电压，比在参比材料CBP和B-Alq的情况下明显更低(参见表1)。
表1：使用各种不同主体材料并使用Ir(piq)3作为掺杂物的器件的结果
实验 EML 最大效率 [cd/A] 1000cd/m2时 的电压[V] CIE(x，y) 1000cd/m2初始发光 下的寿命[h]
实施例9 (对比) CBP：10％的 Ir(piq)3(40nm) 6.5 6.8 0.68/0.32 6000
实施例10 (对比) BAlq：10％的 Ir(piq)3(40nm) 8.0 7.5 0.68/0.32 7000
实施例11 Zn配合物(1)： 10％的Ir(piq)3 (40nm) 8.5 5.0 0.68/0.32 9000

Claims (14)

1.有机电致发光器件，其在发射层中包含至少一种磷光化合物和至少一种式(I)的化合物
其中使用的符号和下标含义如下：
M每次出现时，相同或不同地是处于氧化态+II的金属离子，选自Be，Mg，Ca和Zn；
X每次出现时，相同或不同地是O或S；
Ar1是具有5到60个芳香环原子的芳香性或杂芳香性环体系，其可以被一个或多个基团R取代，且其中单独的芳香性基团可以通过具有1到10个C原子的亚烷基彼此相连，此外，其中一个或多个非相邻的C原子可以被O或S替代；
Ar2每次出现时，相同或不同地是具有5到60个芳香环原子的芳香性或杂芳香性环体系，其可以被一个或多个基团R取代；
Y是单键；
R每次出现时，相同或不同地是H，F，Cl，Br，I，N(R2)2，CN，NO2，Si(R2)3，B(OR2)2，C(＝O)R2，P(＝O)(R2)2，S(＝O)R2，S(＝O)2R2，OSO2R2，具有1到40个C原子的直链烷基、烷氧基或硫代烷基，或具有3到40个C原子的支链或环状烷基、烷氧基或硫代烷基，它们各自可以被一个或多个基团R2取代，其中一个或多个非相邻的CH2基团可以被R2C＝CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C＝O、C＝S、C＝Se、C＝NR2、P(＝O)(R2)、SO、SO2、NR2、O、S或CONR2替代，并且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2替代，或具有5到60个芳香环原子的芳香性或杂芳香性环体系，它们各自可以被一个或多个基团R2取代，或具有5到60个芳香性环原子的芳氧基或杂芳氧基，它们可以被一个或多个基团R2取代，或这些体系的组合；在这里，两个或多个取代基R也可以彼此形成单环或多环脂族或芳香性环体系；
R1每次出现时，相同或不同地是H，F，CF3，具有1到40个C原子的直链烷基，或具有3到40个C原子的支链或环状烷基，它们各自可以被一个或多个基团R2取代，其中一个或多个非相邻的CH2基团可以被R2C＝CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2替代，并且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2替代，或具有5到60个芳香环原子的芳香性或杂芳香性环体系，它们各自可以被一个或多个基团R2取代，或这些体系的组合；在这里，R1也可以与一个或多个取代基R形成单环或多环脂族或芳香性环体系；
R2每次出现时，相同或不同地是H、F或具有1到20个C原子的脂族、芳香族或杂芳族烃类基团，此外，其中一个或多个H原子可以被F替代；在这里，两个或多个取代基R2也可以彼此形成单环或多环脂族或芳香性环体系；
n是0。
2.权利要求1所述的有机电致发光器件，其特征在于，基团Y-Ar1-Y表示式(II)到(X)和(XIII)到(XV)的基团，其中虚线表示与亚胺氮的连接：
3.权利要求1所述的有机电致发光器件，其特征在于，符号Ar2每次出现时，相同或不同地代表具有5到16个芳香性环原子的芳基或杂芳基，它可以被一个或多个基团R取代。
4.权利要求3所述的有机电致发光器件，其特征在于，符号Ar2每次出现时，相同或不同地选自苯基，1-或2-萘基，4-联苯基，1-或2-蒽基，2-或3-噻吩基，2-或3-吡咯基，2-或3-呋喃基，2-、3-或4-吡啶基，3-或4-哒嗪基，4-或5-嘧啶基，吡嗪基，2-、3-、4-、5-、6-、7-或8-喹啉基，或3-、4-、5-、6-、7-或8-异喹啉基，其各自可以被一个或多个基团R取代。
5.权利要求1所述的有机电致发光器件，其特征在于，符号R每次出现时，相同或不同地代表F，N(R2)2，Si(R2)3，C(＝O)R2，P(＝O)(R2)2，具有1到10个C原子的直链烷基或具有3到10个C原子的支链或环状烷基，其各自可以被一个或多个基团R2取代，其中一个或多个非相邻的CH2基团可以被R2C＝CR2、O或S替代，且一个或多个H原子可以被F替代，或具有5到16个芳香性环原子的芳基或杂芳基，它们各自可以被一个或多个基团R2取代，或这些体系的组合；在这里，两个或多个取代基R2也可以彼此形成单环或多环脂族或芳香性环体系。
6.权利要求1所述的有机电致发光器件，其特征在于，符号R1每次出现时相同或不同地代表H，具有1到6个C原子的直链烷基或具有3到6个C原子的支链或环状烷基，其中在每种情况下，一个或多个H原子也可以被F替代，或代表具有5到16个芳香性环原子的芳基或杂芳基，它们各自可以被一个或多个基团R2取代。
7.权利要求1所述的有机电致发光器件，其特征在于式(I)的化合物采取固态的简单配合物的形式或二聚体或寡聚体的形式。
8.权利要求1所述的有机电致发光器件，其特征在于在式(I)的化合物中，所有符号Ar2是相同的，所有符号X是相同的，所有符号R1是相同的，所有符号Y是相同的，并且化合物被相同地取代。
9.权利要求1所述的有机电致发光器件，其特征在于它包含阴极、阳极以及至少一个发射层，并任选包含其它层，所述其它层选自空穴注入层，空穴传输层、电子阻挡层、空穴阻挡层、电子传输层、电子注入层、电荷产生层和有机或无机p/n结。
10.权利要求1所述的有机电致发光器件，其特征在于有机电致发光器件包含多个发射层，其中至少一个层包含至少一种式(I)的化合物和至少一种磷光化合物。
11.权利要求1所述的有机电致发光器件，其特征在于磷光化合物包含铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕。
12.权利要求11所述的有机电致发光器件，其特征在于磷光化合物包含至少一种式(XXII)到(XXV)的化合物
其中R具有与权利要求1中定义相同的含义，且使用的其它符号意义如下：
DCy每次出现时，相同或不同地是环状基团，所述环状基团包含至少一个供体原子，环状基团通过所述供体原子与金属键合，并且所述供体原子可以反过来带有一个或多个取代基R；基团DCy和CCy通过共价键彼此相连；
CCy每次出现时，相同或不同地是包含碳原子的环状基团，环状基团通过所述碳原子与金属键合，并且所述碳原子可以反过来带有一个或多个取代基R；
A每次出现时，相同或不同地是单阴离子、二齿螯合配体。
13.用于生产权利要求1到12中的一项所述的有机电致发光器件的方法，其特征在于利用升华方法，或利用有机气相沉积方法，或利用有机气相喷印方法，或借助于载气升华而施加所述一个或多个层，或者通过旋涂或利用印刷方法从溶液产生所述一个或多个层。
14.权利要求1到8中的一项所述的式(I)化合物作为用于有机电致发光器件中磷光化合物的基质材料的用途。
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