CN1602344A - 电致发光铂化合物和由这种化合物制造的器件 - Google Patents

电致发光铂化合物和由这种化合物制造的器件 Download PDF

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CN1602344A
CN1602344A CNA02822129XA CN02822129A CN1602344A CN 1602344 A CN1602344 A CN 1602344A CN A02822129X A CNA02822129X A CN A02822129XA CN 02822129 A CN02822129 A CN 02822129A CN 1602344 A CN1602344 A CN 1602344A
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D·D·莱克洛克斯
V·A·佩特罗夫
E·M·史密斯
Y·王
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Abstract

本发明总体上涉及在可见光区具有最大发射值的电致发光Pt(II)配合物和用Pt(II)配合物制造的器件。

Description

电致发光铂化合物和由这种化合物制造的器件
发明领域
本发明涉及在可见光区具有发射光谱的电致发光铂(II)配合物。还涉及其中的活性层包含一种电致发光Pt(II)配合物的电子器件。
有关技术的说明
许多不同种类的电子设备中有能发光的有机器件，比如构成显示器的发光二极管。在所有这些器件中，有机发光层被夹在两个电接触层之间。至少一个电接触层是透光的，因此，光能通过电接触层。当在这两个电接触层上施加电压时有机层发光通过透光电接触层。
用有机电致发光化合物作为发光二极管中的活性组分是众所周知的。已知简单的有机分子，比如蒽，噻二唑衍生物和香豆素衍生物，能显示电致发光。半导体共轭聚合物也被用作电致发光组分，比如，Friend等的美国专利5247190，Heeger等的美国专利5408109和Nakano等的已公开欧洲专利申请443861中所公开内容。8-羟基喹啉根和三价金属离子，特别是铝，的配合物，被广泛用作电致发光组分，比如Tang等的美国专利5552678中所公开内容。
Burrows和Thompson在已公开的PCT申请WO 00/57676中公开了一种具有用铂的有机金属配合物掺杂的聚合物发光层的电致发光器件。
但是，仍然有必要提供在可见光区发光的有效的电致发光化合物。
发明概述
本发明涉及一种具有通式I或通式II的金属配合物：
    PtL1L2                                    (I)
    PtL1L3L4                                  (II)
其中：
通式I中：
    L2是单阴离子二齿配位体；
通式II中：
    L3是单齿配位体；和
    L4是单齿膦配位体；
在通式I和II中：
    L1选自图1所示的通式III和图2所示的通式VII，其中：
在通式III和VII中：
E1到E4当各自存在时是相同或不同的，是CR2或N；
R2当各自存在时是相同或不同的，选自H，D，Cn(H+F)2n+1，F，OCn(H+F)2n+1，OCF2Y，SR3和N(R3)2，或者相邻的R2基团可连接成五元或六元环；
R3是H，CnH2n+1；
Y是H，Cl或Br；
N是1到12的整数：
在通式III中：
A是N或SR3；
R1当各自存在时是相同或不同的，选自D，Cn(H+F)2n+1，F，OCn(H+F)2n+1，OCF2Y，SR3和N(R3)2，或相邻的R基团可连接成五元或六元环；
α是0，1或2；和
在通式VII中：
R4到R7当各自存在时是相同或不同的，选自H，D，Cn(H+F)2n+1，F，OCn(H+F)2n+1，OCF2Y，SR3和N(R3)2，或相邻的R基团可连接成五元或六元环。
在另一个实例中，本发明涉及具有至少一个包含上述金属配合物或其组合的活性层的一种有机电子器件。
这里所用术语“化合物”是指由进一步由无法被物理方法分离的原子组成的分子所构成的一种不带电荷的物质。术语“配位体”是指与金属离子配位层结合的分子，离子或原子。字母“L”用来表示由中性母体化合物“HL”失去一个氢离子而形成的具有名义电荷(-1)的配位体。术语名词“配合物”是指具有至少一个金属离子和至少一个配位体的一种化合物。术语“β-二羰基”是指其中的两个酮基被一个CHR基团分隔的一种中性化合物。术语“β-烯醇根”是指β-二羰基的阴离子形式，其中两个羰基之间的CHR基团的H已被夺取。术语“基团”是指化合物的一部分，比如有机化合物中的取代基或配合物中的配位体。术语“相邻”当用来指器件中的层时，不一定指一层紧邻另一层。另一方面，短语“相邻R基团”是指化学通式中彼此邻近的R基团(即，通过一个键连接的两个原子上的两个R基团)。术语“光活性”是指具有电致发光和/或光敏性的任何物质。另外，全文采用IUPAC编号体系，周期表中的族从左到右编号为1到18(《CRC化学物理手册》(CRC Handbook of Chemistry andPhysics)，第81版，2000)。在通式和反应式中，用字母A，E，L，R，Q，Y和Z表示本文定义的原子或基团。用所有其他字母表示传统原子符号。术语“(H+F)”是指氢和氟的全部组合，包括完全氢化的，部分氟化的或全氟化取代基。“最大发射值”是指获得电致发光最大强度处的纳米波长。电致发光通常在二极管结构中测量，其中待测物质被夹在两个电接触层之间，并施加电压。可以分别用光电二极管和光谱仪测定光强和波长。
附图说明
图1表示本发明金属配合物中配位体L1的通式III到VII。
图2表示本发明金属配合物中配位体L1的通式VII到X。
图3表示可用于本发明的β-烯醇根配位体的通式XI和膦醇根配位体的通式XII。
图4表示可用于本发明的母体配位体化合物HL1的合成反应式(1)。
图5表示可用于本发明的L3配位体的通式。
图6A和6B表示可用于本发明的L4配位体的通式。
图7表示可用于本发明的形成通式I配合物的反应式(2)和(3)。
图8表示可用于本发明的形成通式II配合物的反应式(4)。
图9是一种发光器件(LED)的示意图。
图10是一种LED测试设备的示意图。
较佳实施方式的详细说明
本发明金属配合物具有上述通式I或通式II，并被称为环状金属取代(cyclometallated)配合物。铂以+2价氧化态存在，并且是四配位的。通式I中的配合物是具有一个附加单阴离子二齿配位体L2的环状金属取代配合物。通式II中的配合物是具有两个附加单齿配位体L3和L4的环状金属取代配合物。优选的环状金属取代配合物是中性和非离子的，可以完全升华。通过真空淀积获得的这些物质的膜具有良好到极佳的电致发光特性。
本发明配合物发射光谱的最大值在蓝光到红光区域。通过下述方法选择合适配位体，可以调节发射光的颜色。
图1中所示具有通式III的配位体L1，得自于其中的噻吩基(A是S时)或吡咯基(A是NR3时)与具有至少一个氮的六元环连接的母体化合物。优选α是0。当A是NR3时，优选R3是CH3。
当全部E都是CR2，而且R2基是不连接成环的独立取代基时，配位体得自于噻吩基和吡咯基-吡啶母体化合物。优选有至少一个氘或含氟取代基位于吡啶环上，更优选位于E1和E3位。优选的含氟取代基是F和CF3。
具有通式III的一般结构的其他种类的配位体，具有代替吡啶的喹啉或异喹啉基团，如图1所示的通式IV到VI。具有图1所示通式IV的配位体L1，得自于噻吩基或吡咯基-喹啉母体化合物。具有图1所示通式V或通式VI的配位体L1，得自于噻吩基或吡咯基-异喹啉母体化合物。其中δ是0或1到4的整数，R1，α和A如上述通式III中所定义。优选至少一个喹啉或异喹啉环上的取代基选自D，Cn(F)2n+1，F，OCn(F)2n+1和OCF2Y。
具有图2所示通式VII的配位体L1，得自于其中的苯基与具有至少一个氮的六元环相连的母体化合物。
当所有E都是CR2，而且R2基团是不连接成环的独立取代基时，配位体得自于苯基-吡啶母体化合物。优选有至少一个氘或含氟取代基位于配位体上，更优选位于E1和E3位。优选的含氟取代基是F和CF3。
具有通式VII一般结构的其他种类的配位体，具有代替吡啶的喹啉或异喹啉基团，如图2中通式VIII到X所示。具有图2所示通式VIII的配位体L1，得自于苯基-喹啉母体化合物。具有图2所示通式IX或通式X的配位体L1，得自于苯基-异喹啉母体化合物。其中δ是0或1到4的整数，而且R1和α如上述通式III中所定义，R4到R7如上述通式VII中所定义。优选配位体上至少一个取代基选自D，Cn(F)2n+1，F，OCn(F)2n+1和OCF2Y。
母体配位体化合物HL1，通常可以由标准钯催化的相应杂环芳基氯化物与有机硼酸或有机镁试剂的Suzuki或Kumada交叉偶联反应制备，如0.Lohse，P.Thevenin和E.Waldvogel在Synlett，1999，45-48中所述。图4中的反应式(1)说明了苯基-异喹啉的这个反应，其中R和R’表示取代基。部分或全部氘化的配位体母体化合物通常可以用氘化组分由相同偶联方法制备。氘化组分通常可以购得或由已知合成方法制得。
L2配位体是单阴离子二齿配位体。总的来说，这些配位体具有N，O，P，或S作为配位原子，而且与铂配位时形成五元或六元环。适用的配位基团包括氨基，亚氨基，酰胺基，醇根，羧酸根，膦基，硫醇根等。这些配位体的适用母体化合物的实例包括β-二羰基(β-烯醇根配位体)，及其N和S的类似物；氨基羧酸(氨基羧酸根配位体)；吡啶羧酸(亚氨基羧酸根配位体)；水杨酸衍生物(水杨酸根配位体)；羟基喹啉(羟基喹啉根配位体)及其S的类似物；和二芳基膦链烷醇(二芳基膦醇根配位体)。
β-烯醇根配位体通常具有附图3所示的通式XI，其中R8当各自存在时是相同或不同的。R8基团可以是氢，卤素，取代或未取代的烷基，芳基，烷芳基或杂环基团。相邻的R8基团可以连接成可以被取代的五元和六元环。优选的R8基团选自H，F，Cn(H+F)2n+1，-C6H5，-C4H3S和-C4H3O，其中n是1到12，优选1到6的整数。
适用β-烯醇根配位体的实例包括下列化合物。β-烯醇根的缩写形式以括号形式表示。
2，4-戊二酮根[acac]
1，3-二苯基-1，3-丙二酮根[DI]
2，2，6，6-四甲基-3，5-庚二酮根[TMH]
4，4，4-三氟-1-(2-噻吩基)-1，3-丁二酮根[TTFA]
7，7-二甲基-1，1，1，2，2，3，3-七氟-4，6-辛二酮根[FOD]
1，1，1，3，5，5，5-七氟-2，4-戊二酮根[F7acac]
1，1，1，5，5，5-六氟-2，4-戊二酮根[F6acac]
1-苯基-3-甲基-4-异丁酰-吡唑酮根[FMBP]
β-二羰基母体化合物通常可以购得。母体化合物1，1，1，3，5，5，5-七氟-2，4-戊二酮，CF3C(O)CFHC(O)CF3，可以通过全氟2-戊二烯和氨的反应和随后的水解步骤的两步合成制得。这种化合物由于容易水解，应该在无水条件下储存和反应。
可以用如部分或全氟化的烷基或烷氧基取代羟基喹啉根配位体。适用羟基喹啉根配位体的实例包括(缩写在括号中)：
8-羟基喹啉根[8hq]
2-甲基-8-羟基喹啉根[Me-8hq]
10-羟基苯并喹啉根[10-hbq]
母体羟基喹啉化合物通常可以购得。
膦醇根配位体通常具有图3所示的通式XII，其中
R9当各自存在时可以是相同或不同的，选自Cn(H+F)2n+1和C6(H+F)5，
R15当各自存在时可以是相同或不同的，选自H和Cn(H+F)2n+1和φ是2或3。适用膦醇根配位体的实例包括(缩写在括号中)：
3-(二苯基膦基)-1-氧丙烷[dpp0]
1，1-双(三氟甲基)-2-(二苯基膦基)-乙醇根[tfmdpe0]一些母体膦链烷醇化合物可以购得，或通过已知方法制得，比如，《无机化学》(Inorg.Chem.)1985，第24卷，第3680页中报道的tfmdpe0的制备方法。
L3配位体是单齿配位体。优选该配位体是单阴离子的。这种配位体可以具有O或S作为配位原子，配位基团可以是，比如醇根，羧酸根，硫代羧酸根，二硫代羧酸根，磺酸根，硫醇根，氨基甲酸根，二硫代氨根甲酸根，硫代卡巴腙阴离子，磺酰胺阴离子等。一些情况下，如β-烯醇根等配位体可以作为单齿配位体。L3配位体还可以是配位阴离子，比如卤离子，硝酸根，硫酸根，六卤锑酸根等。适用L3配位体的实例如图5中所示。
L3配位体通常可以购得。
L4配位体是单齿膦配位体。优选这种配位体是非离子的。膦配位体可以具有通式XIII
PAr3                                           (XIII)其中Ar代表芳基或杂芳基。Ar基团可以被烷基，杂烷基，芳基，杂芳基，卤基，羧基，次硫酸基，或氨基取代，或不被取代。适用L4配位体的实例如附图6A和6B所示，其中用“Me”在附6A的通式6-3，6-8，6-8中和图6B的通式6-13，6-16，6-17，6-18，6-19和6-21中代表甲基。L4膦配位体通常可以购得。
通式I和II的配合物的发光颜色，很大程度上取决于配位体L1，L2，L3和L4的选择。总的来说，当L1具有通式III时，颜色移向较长波长(“红移”)。当L1具有通式VII时，颜色移向较短波长(“蓝移”)。当配位体的含氮环具有至少一个通过具有非键合π电子，最优选是氧，的杂原子成键的取代基时，或具有至少一个能供给σ电子，比如烷基，优选是甲基，的取代基时，配合物也会发生蓝移。但是，也会发生违反这些一般原则的例外情况。
使用其中部分或全部氢被氘代替的L1配位体，可以提高配合物的发光效率。
通式I配合物的制备通常是从金属氯化物盐形成桥接氯化物二聚物开始的。图7所示的反应式(2)用噻吩-吡啶配位体说明了这个反应。然后向桥接氯化物二聚物中加入母体配位体化合物的盐，比如NaL2，形成通式I的配合物。图7中的反应式(3)用β-烯醇根配位体的钠盐说明了这个反应。母体配位体化合物的盐可以由任何传统方法制得，比如在惰性溶剂中，将氢化钠加入HL2中。
具有通式I的本发明金属配合物的实例列在下表1中。α和δ当各自存在时都是0。
                         表1
配合物 L1通式  A  取代基  L2
 1-a III  N-CH3  E1＝E3＝E4＝CHE1＝CCF3  acac
 1-b IX  -  无  acac
 1-c IX  -  R6＝叔-丁基  acac
 1-d IX  -  R5＝OCH3  acac
 1-e IX  -  R6＝CF3  acac
 1-f IX  -  R6＝F  acac
 1-g VII  -  E1＝E2＝E4＝CHE3＝CCH3R5＝CF3R7＝CF3  TMH
 1-h VII  -  E1＝E3＝E4＝CHE2＝COCH3R5＝CF3  tfmdpe0
 1-i VII  -  E1＝E3＝E4＝CHE2＝COCH3R4＝FR6＝F  TMH
 1-j VII  -  E1＝E2＝E4＝CHE3＝CCH3R4＝FR6＝F  tfmdpe0
 1-k VII  -  E1＝E3＝E4＝CHE2＝COC(CH3)3R4＝FR6＝F  TMH
 1-l VII  -  E1＝E2＝E4＝CHE3＝CCH3R4＝FR6＝F  TMH
 1-m VII  -  E1＝E2＝E4＝CHE3＝CCH3R5＝CF3  TMH
通式II的配合物通常也可以由首先形成桥接氯化物二聚物制备。然后向该二聚物中加入其他两种配位体。优选L3是单阴离子的，而且以银盐AgL3形式加入。L4作为中性配位体加入，或者在阴离子配位体情况下，以NaL4的盐形式加入。图8所示的反应式(4)用具有苯基-吡啶配位体的桥接氯化物二聚物说明了优选反应。
制备一组具有通式II的配合物，其中L1选自下表2中列出的一种配位体，L3选自图5所示的配位体，而且L4选自图6A和6B所示的配位体。
                           表2
配位体 L1通式   A   α   取代基
  2-a   III   S   0   E1＝E2＝E4＝CHE3＝CCF3
  2-b   III   N-CH3   0   E1＝E2＝E4＝CHE3＝CCF3
  2-c   VII   -   -   E1＝E3＝E4＝CHE2＝COCH3R5＝CF3
  2-d   VII   -   -   E1＝E2＝E4＝CHE3＝COCH3R5＝CF3
  2-e   VII   -   -   E1＝E3＝E4＝CHE2＝CCH3R4＝FR6＝F
  2-f   VII   -   -   E1＝E3＝E4＝CHE2＝COCH3R4＝FR6＝F
大部分具有配位体2-a或2-b的配合物具有红色到红桔色发光。大部分具有配位体2-c，2-d，2-e，或2-f配位体的配合物具有蓝色或蓝绿色发光，
电子器件
本发明还涉及包括至少一个位于两个电接触层之间的光活性层的一种电子器件，其中该器件的至少一个光活性层包括本发明的配合物。如图9所示，一个典型器件100具阳极层110和阴极层150和介于阳极110和阴极150之间的电活性层120，130和任选的140。与阳极相邻的是空穴注入/输运层120。与阴极相邻的是包含电子输运物质的任选层140。在空穴注入/输运层120和阴极(或任选的电子输运层)之间是光活性层130。层120，130和140各自并一起被称为活性层。
根据器件100的应用，光活性层130可以是被施加的电压激活的发光层(比如在发光二极管或发光电化学电池中)，其中的物质不论是否施加偏压，都能够响应辐射能并产生信号的层(比如在光检测器中)。光检测器的实例包括光电导管，光敏电阻器，光控开关，光电晶体管和光电管和光伏电池，这些术语在Markus，John的《电子学和核子学词典》(Electronics and NucleonicsDictionary)470和476(McGraw-Hill，Inc.1996)中有说明。
本发明的配合物特别适用作OLED发光层中的活性物质，或层140中的电子输运物质。优选本发明的铂配合物被用作二极管中的发光物质。当被用于层130中时，发现本发明的配合物无须为了有效而存在于固体基质稀释剂中。包含占该层总重量大于20重量％，最高基本上100重量％的金属配合物的层，可以用作发光层。“基本上100％”是指金属配合物是层中除了形成层过程中可能产生的杂质或外来副产物之外唯一的物质。金属配合物发光层中还可以含有附加物质。比如，可以含有荧光颜料来改变发射光的颜色。还可以添加稀释剂。优选的稀释剂有助于层中的电荷输运。稀释剂可以是聚合物质，比如聚(N-乙烯基咔唑)和聚硅烷。也可以是一种小分子，比如4，4’-N，N’-二咔唑联苯或三元芳香胺。使用稀释剂时，金属配合物的含量通常较少，一般小于该层总重量的20重量％，优选小于10重量％。
一种适用于本发明铂金属配合物的稀释剂是共轭聚合物，其中该聚合物的三重受激态处于具有比铂配合物的三重受激态更高的能级。适用共轭聚合物的实例包括聚亚芳基亚乙烯基，聚芴，聚噁二唑，聚苯胺，聚噻吩，聚吡啶，聚亚苯基，它们的共聚物，及它们的组合。共轭聚合物可以是含有非共轭部分的共聚物，比如含有丙烯酸类、甲基丙烯酸类、或乙烯基的单体单元。特别适用的是芴和取代芴的均聚物和共聚物。
一些情况下，本发明的金属配合物可以以超过一种同分异构形式存在，或以不同配合物的混合形式存在。当然在上述关于OLED的讨论中，术语“金属配合物”包括配合物的混合物和/或异构体。
器件通常还包括可与阳极或阴极相邻的支承层(未示出)。支承层通常与阳极相邻。支承层可以是柔性的或刚性的，有机或无机的。通常用玻璃或柔性的有机膜作为支承层。阳极110是能特别有效地注入或收集正电荷载流子的电极。阳极优选由包含金属，混合金属，合金，金属氧化物或混合金属氧化物的物质制成。适用金属包括第11族金属，第4，5和6族中的金属和第8-10族的过渡金属。如果要求阳极是透光的，则通常使用第12，13和14族金属的混合金属氧化物，比如铟-锡-氧化物。阳极110还可以包含一种有机物质，比如聚苯胺，如《自然》(Nature)第357卷第477-479页(1992年6月11日)的《由可溶性导电聚合物制成的柔性发光二极管》(Flexible light-emitting diodesmade from soluble conducting polymers)中所述。
阳极层110通常是由物理蒸汽淀积方法或旋转浇铸方法制得的。术语“物理蒸汽淀积”是指在真空中进行的各种淀积方法。因此，物理蒸汽淀积包括所有形式的溅射，包括电子束溅射和所有形式的蒸汽淀积，比如电子束蒸发和电阻蒸发。特别适用的物理蒸气淀积是射频磁控管溅射。
通常有空穴输运层120与阳极相邻。层120的空穴输运物质的实例，如Y.Wang所著《Kirk-Othmer化学技术百科全书》(Kirk-Othmer Encyclopedia ofChemical Technology)第四版，第18卷，第837-860页，1996中所概述。空穴输运分子和聚合物都可以使用。除上述TPD和MPMP之外的常用空穴输运分子是：1，1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC)；N，N’-双(4-甲苯基)-N，N’-双(4-乙苯基)-[1，1’-(3，3’-二甲基)联苯基]-4，4’-二胺(ETPD)；四-(3-甲苯基)-N，N，N’，N’-2，5-亚苯基二胺(PDA)；α-苯基-4-N，N-二苯基氨基苯乙烯(TPS)；对-(二乙氨基)苯甲醛二苯腙(DEH)；三苯胺(TPA)；1-苯基-3-[对-(二乙氨基)苯乙烯基]-5-[对-(二乙氨基)苯基]吡唑啉(PPR或DEASP)；1，2-反式-双(9H-咔唑-9-基)环丁烷(DCZB)；N，N，N’，N’-四(4-甲苯基)-(1，1’-联苯基)-4，4’-二胺(TTB)；和卟啉化合物，比如酞菁铜。常用的空穴输运聚合物是聚乙烯基咔唑，(苯基甲基)聚硅烷，聚(3，4-亚乙基二氧噻吩)(PEDOT)和聚苯胺。也可以通过向聚苯乙烯和聚碳酸酯等聚合物中掺杂上述空穴输运分子的方法获得空穴输运聚合物。
任选的层140不仅起可以帮助电子输运的作用，而且能起到缓冲层或抗猝灭层，防止在层界面上发生猝灭反应的作用。优选该层能促进电子迁移和降低猝灭反应。任选层140中的电子输运物质的实例包括金属螯合oxinoid化合物，比如三(8-羟基喹啉根合)铝(Alq3)；菲咯啉基化合物，比如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)和吡咯化合物，比如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)。
阴极150是对注入或收集电子或负电荷载流子特别有效的电极。阴极可以是任何具有比第一电接触层(此处指阳极)更低功函数的金属或非金属。第二电接触层的物质可以选自第1族的碱金属(比如，Li，Cs)，第2族(碱土)金属，第12族金属，镧系金属和锕系金属。可以使用物质比如铝，铟，钙，钡，钐或镁，及其混合。
已知有机电子器件中还有其他层。比如，在导电聚合层120和活性层130之间具有一个层(未示出)，能帮助层的正电荷输运和/或带隙匹配，或起到保护层的作用。相似地，在活性层130和阴极层150之间可以有附加层(未示出)，能帮助层之间的负电荷输运和/或带隙匹配，或作为保护层。可以使用本领域已知的层。另外，任何上述层都可由两层或更多层构成。或者，可以对无机阳极层110，导电聚合层120，活性层130和阴极层150的部分和全部，进行表面处理，提高电荷载流子输运效率。每个组成层的物质选择优选通过权衡提供具有高器件效率的器件的目标来确定。
当然每个功能层都可以由超过一层构成。
器件可以通过将各层按顺序蒸汽淀积于合适基片上制成。可以使用如玻璃和聚合物膜作为基片。可以使用传统蒸汽淀积技术，比如热蒸发，化学蒸汽淀积等。或者，可以采用任何传统涂覆技术，可由溶液或合适溶剂中的分散体涂覆有机层。总的来说，不同层具有以下范围的厚度：阳极110，500-5000埃，优选1000-2000埃；空穴输运层120，50-2500埃，优选200-2000埃；发光层130，10-1000埃，优选100-800埃；任选电子输运层140，50-1000埃，优选100-800埃；阴极150，200-10,000埃，优选300-5,000埃。电子-空穴复合区在器件中的位置，以及器件的发射光谱，受每个层相对厚度的影响。比如，使用Alq3等发射体作为电子输运层时，电子-空穴复合区就在Alq3层中。那时发射是Alq3的发射，而不是所需的尖锐的镧系发射。因此，电子输运层的厚度必须选择成使电子-空穴复合区位于发光层中。所需的层厚度比例取决于所用物质的确切特性。
当然优化器件中的其他层，能进一步提高本发明由金属配合物制成的器件的效率。例如，可以使用更高效的阴极，比如Ca，Ba，Mg/Ag，或LiF/Al。也可以使用某些形状的基片和新颖的空穴输运物质，降低工作电压或提高量子效率。也可以添加附加层，满足不同层的能级要求，有助于电致发光的产生。
本发明的配合物通常是发出磷光和荧光的，也可用于其他应用中。比如，该配合物可以用作氧敏性指示器，生物测定中的荧光指示和催化剂。
实施例
以下实施例说明本发明的某些特点和优点。这些实施例是对发明的说明，而不是限制。所有百分比除了另有说明之外，都是摩尔百分比。
实施例1
本实施例说明母体配位体化合物2-(2，4-二氟苯基)-4-甲氧基吡啶的制备。
将2-氯-4-甲氧基吡啶(Lancaster Synthesis Inc.，3.50克，24.4毫摩尔)，2，4-二氟苯基硼酸(Aldrich Chemical Co.，3.85克，24.4毫摩尔)，碳酸钾(EM Science，6.74克，48.8摩尔)，四-三苯基膦钯(O)(Aldrich ChemicalCo.，400毫克，0.346毫摩尔)，二甲氧基乙烷(Aldrich，50毫升)和水(50毫升)在氮气中回流搅拌15小时。然后分离有机组分，用3×25毫升二乙醚萃取含水部分。用硫酸钠干燥合并的有机部分，并蒸发至干。以己烷/乙酸乙酯(6∶1)作为洗脱溶剂用硅胶闪式色谱法纯化所得的粗制油状物，得到所需的无色油状产物，用1H NMR分析纯度大于95％。分离产率＝3.8克(70％)。1H NMR(CDCl3，296K，300MHz)：δ8.52(1H，d，J＝5.9Hz)，7.99(1H，m)，7.27(1H，dd，J＝2.1和2.0Hz)，6.98(1H，m)，6.89(1H，m)，6.82(1H，d，J＝2.4Hz)，3.89(3H，s)ppm。19F NMR(CDCl3，296K，282MHz)δ＝-109.05(1F，dd，JF-F＝11Hz和JF-H＝18Hz)，-112.80(1F，brs)ppm。
实施例2
本实施例说明桥接氯化物二聚物[PtCl{2-(2，4-二氟苯基)-4-甲氧基-吡啶}]2的形成。
将实施例1的2-(2，4-二氟苯基)-4-甲氧基-吡啶(1.50克，6.79毫摩尔)，氯化铂(II)(Strem Chemicals，1.641克，6.17毫摩尔)，无水四丁基氯化铵(Aldrich Chemical Co.，171毫克，0.617毫摩尔)和氯苯(Aldrich)在氮气中回流15小时，然后过滤分离制得的沉淀产物，用甲醇洗涤，并在真空中干燥，制得所需的灰白色固体产物。分离产率＝2.31克(75％)。1H NMR(DMSO-d6，296K，300MHz)：δ9.32(1H，d，J＝7.0Hz)，8.01(1H，dd，J＝10.8和2.4Hz)，7.50(1H，dd，J＝3.0和2.9Hz)，7.18(1H，dd，J＝6.9和2.7Hz)，7.05(1H，m)，3.99(3H，s)ppm。19F NMR(DMSO-d6，296K，282MHz)δ＝-106.79(1F，d，JF-F＝11Hz)，-110.16(1F，d，JF-F＝11Hz)ppm。
实施例3
本实施例说明Pt(TMH){2-(2，4-二氟苯基)-4-甲氧基吡啶}，化合物1-i的形成。
将实施例2的[PtCl{2-(2，4-二氟苯基)-4-甲氧基吡啶}]2(200毫克，0.22毫摩尔)，2，2，6，6-四甲基-3，5-庚二酮，钠盐(从2，2，6，6-四甲基-3，5-庚二酮，(Aldrich Chemical Co.)和氢化钠(Aldrich)制备；120毫克，0.56毫摩尔)和2-乙氧基乙醇(Aldrich，20毫升)在120℃下搅拌45分钟。然后在真空下除去挥发性组分，将得到的残余物再溶解于CD2Cl2中，用CD2Cl2作为洗脱溶剂通过一块硅胶。收集发出蓝色荧光的部分(Rf＝1.0)并蒸发至干，获得所需的米色固体产物。分离产率＝212毫克(80％)。1H NMR(CD2Cl2，296K，300MHz)：δ8.76(1H，d，J＝6.8Hz)，7.51(1H，dd，J＝2.7和2.6Hz)，7.08(1H，dd，J＝8.7和2.3Hz)，6.58(1H，m)，5.85(1H，s)，3.95(3H，s)，1.27(18H，s)ppm。19FNMR(CD2Cl2，296K，282MHz)δ＝-108.26(1F，d，JF-F＝11Hz)，-113.36(1F，d，JF-F＝11Hz)ppm。
按照与实施例1-3相似的方式制备化合物1-a到1-h和1-j到1-m。
实施例4
本实施例说明用本发明的铂配合物形成OLED。
通过热蒸发技术制造包括空穴输运层(HT层)，电致发光层(EL层)和至少一个电子输运层(ET层)的薄膜OLED器件。使用带油扩散泵的Edward Auto 306蒸发器。全部薄膜淀积的基础真空度在10-6乇范围内。无须影响真空度就能在淀积室中淀积五个不同的膜。
使用有铟锡氧化物(ITO)涂层的玻璃基片，ITO层厚度是约1000-1000埃。先在基片上用1N盐酸溶液蚀刻掉不需要的ITO区域，形成第一电极图案。使用聚酰亚胺带作掩模。然后在洗涤剂水溶液中对蚀刻有图案的ITO基片进行超声清洗。然后用蒸馏水，异丙醇依次清洗基片，并在甲苯蒸汽中对其除油脂约3小时。或者，使用从Thin Film Devices，Inc获得的有图案的ITO。这些ITO是涂覆有1400埃ITO涂层的Corning 1737玻璃，具有30欧姆/方块的薄膜电阻和80％的透光率。
然后将清洁的有图案的ITO基片置于真空室中，将真空室抽真空至10-6乇。然后用氧等离子体进一步清洁处理基片约5-10分钟。清洁后，将多层薄膜用热蒸发技术依次淀积于基片上。最后，通过掩模淀积有图案的Al金属电极。在淀积时用石英晶体监视器(Sycon STC-200)测量膜的厚度。实施例中报道的全部膜厚度都是很小的，假设淀积物质的密度为1的计算值。然后从真空室中取出完成的OLED器件，不进行封装直接表征。
器件层和厚度列在表3中。全部样品阳极都是上述ITO。
                           表3
样品 HT层厚度，埃 EL层厚度，埃 ET层厚度，埃 阴极厚度，埃
 1  MPMP511 化合物1-a412  DPA408  Al737
 2  MPMP507 化合物1-b421  DPA407  Al725
 3  MPMP507 化合物1-c419  DPA415  Al738
 4  MPMP534 化合物1-d420  DPA405  Al729
 5  MPMP616 化合物1-e404  DPA406  Al730
 6  MPMP521 化合物1-f430  DPA401  Al728
 7  MPMP518 化合物1-g407  DPA418  Al727
 8  MPMP532 化合物1-h570  DPA412  Al600
 9  MPMP528 化合物1-i418  DPA404  Al736
 10  MPMP514 化合物1-j483  DPA416  Al727
 11  MPMP519 化合物1-k423  DPA403  Al721
 12  MPMP525 化合物1-l411  DPA412  Al752
 13  MPMP550 化合物1-m406  DPA409  Al918
DPA＝4，7-二苯基-1，10-菲咯啉
ET＝电子输运
EL＝电致发光
HT＝空穴输运
MPMP＝双[4-(N，N-二乙氨基)-2-甲苯基](4-甲苯基)甲烷
通过测定OLED样品的以下性质进行表征(1)电流-电压(I-V)曲线，(2)电致发光辐射强度对电压和(3)电致发光光谱对电压。所用仪器200如图10所示。用Keithley Source-Measurement Unit Model 237，280测定OLED样品220的I-V曲线。用Minolta LS-110荧光计210测定电致发光辐射强度(以坎德拉/平方米为单位)对电压的曲线，同时用Keithley SMU扫描电压。用一对透镜230通过电子光间(shutter)240聚集光线，通过光谱仪250分散，然后用二极管阵列式检测器260测量，获得电致发光光谱。全部三种测定都同时进行，并由计算机270控制。用LED的电致发光辐射强度除以器件运行所需的电流密度，求得器件在某一电压的效率。单位是坎德拉/安培。
结果列在下表4中。
             表4.铂化合物的电致发光特性
样品 辐射峰值，坎德拉/平方米 效率峰值，坎德拉/安培 波长大致峰值，纳米
 1  19伏时是8  0.15  620
 2  15伏时是0.02
 3  19伏时是30  0.6  600和640
 4  20伏时是80  0.38  640和690
 5  20伏时是25  0.3  600和640
 6  19伏时是120  1.7  590和640
 7  20伏时是16  0.4  540
 8  21伏时是60  4  475和505
 9  23伏时是130  4  458和489
 10  20伏时是80  7  476和508
 11  23伏时是0.2  0.035
 12  19伏时是90  4.5  473和507
 13  22伏时是700  9  474和507
实施例5(预示性)
本实施例说明用本发明的红光发射Pt物质在聚(芴)聚合基质中形成OLED。将制得的混合物作为OLED中的活性红光发射层。按照实施例3所述制备铂配合物，Pt(acac){1-(5-叔-丁基-苯基)-异喹啉}，表1中的化合物1-c。按照Yamamoto所著《聚合物科学进展》(Progress in Polymer Science)第17卷，第1153页(1992)中所述制备聚芴，用二卤代，优选二溴代的单体单元衍生物与化学计量的零价镍化合物，比如双(1，5-环辛二烯)镍(O)反应。
本实施例中的有机膜组分都经过溶液处理。器件安装如下：在ITO/玻璃基片(Applied Films)上形成图案(器件活性面积＝整个3平方厘米)，并按实施例4所述进行清洁。将基片置于300瓦等离子体炉中进一步清洁15分钟。将聚(亚乙基二氧噻吩)-聚(苯乙烯磺酸)(PEDOT-PSSA，Bayer Corp.)缓冲层(即，空穴输运/注入层)旋涂至90纳米厚度。将膜在200℃的热板上干燥3分钟。然后将基片转移至充有氮气的手套箱中，将聚(芴)聚合物，[Pt(acac){1-(5-叔丁基-苯基)异喹啉}](1.6微摩尔)和无水甲苯(7.5毫升)的溶液旋涂于基片上至厚度为70纳米。然后将基片转移入高真空室中，在2.0×10-6乇真空度下，依次热沉积Ba(3.5纳米)和Al(400纳米)。用可UV固化的环氧树脂将载玻片粘结于阴极顶部，将制得的OLED器件密封隔绝空气。
通过获得电流-电压，亮度-电压，亮度-电流，效率-电压和效率-电流曲线，全面表征器件。使用计算机控制的(Labview软件)Keithley Source-Measurement Unit和光电二极管完成这一工作，后者能对整个3平方厘米器件活性面积的光输出积分。

Claims (14)

1.一种活性层，包括至少一种具有选自通式I和通式II的通式的化合物：
PtL1L2                                       (I)
PtL1L3L4                                     (II)
其中：
在通式I中：
L2是单阴离子二齿配位体；
在通式II中：
L3是单齿配位体；和
L4是单齿膦配位体；
在通式I和II中：
L1选自图1所示的通式III和图2所示的通式VII，其中：
在通式III和VII中：
E1到E4当各自存在时是相同或不同的，而且是CR2或N；
R2当各自存在时是相同或不同的，而且选自H，D，Cn(H+F)2n+1，F，OCn(H+F)2n+1，OCF2Y，SR3和N(R3)2，或相邻的R2基团可连接成五元或六元环；
R3是H，CnH2n+1；
Y是H，Cl，或Br；
N是1到12的整数；
在通式III中：
A是N或SR3；
R1当各自存在时是相同或不同的，而且选自D，Cn(H+F)2n+1，F，OCn(H+F)2n+1，OCF2Y，SR3和N(R3)2，或相邻的R基团可连接成五元或六元环；
α是0，1或2；和
在通式VII中：
R4到R7当各自存在时是相同或不同的，而且选自H，D，Cn(H+F)2n+1，F，OCn(H+F)2n+1，OCF2Y，SR3和N(R3)2，或相邻的R基团可连接成五元或六元环；条件是活性层包含小于20重量％的至少一种化合物，还包含一种稀释剂。
2.一种包含如权利要求1所述的活性层的有机电子器件。
3.如权利要求1所述的活性层或权利要求2所述的器件，其中E1到E4是CR2，而且至少一个R2选自D，Cn(F)2n+1，F，OCn(F)2n+1和OCF2Y。
4.如权利要求1和3中一项或两项所述的活性层，或如权利要求2所述的器件，其中L1具有选自图1所示通式IV，通式V和通式VI的通式，其中δ是0或1到4的整数，或L1具有选自图2所示通式VIII，通式IX和通式X的通式，其中δ是0或1到4的整数，或L1具有通式III，E1到E4中至少一个是CR2，而且R2选自D，F，CF3和OCF3，或L1选自通式IV，通式V和通式VI，α是0，而且至少一个R1选自D，F，CF3和OCF3，或L1具有通式VII，E1到E4中至少一个是CR2，而且R2选自D，F，CF3和OCF3，或L1选自通式VIII，通式IX和通式X，而且至少一个R1选自D，F，CF3和OCF3。
5.如权利要求1，3和4中任一项或多项所述的活性层，或如权利要求2和4中一项或两项所述的器件，其中L3是单阴离子的而且L4是非离子的。
6.如权利要求1和3-5中任一项或多项所述的活性层，或如权利要求2和4-5中一项或两项所述的器件，其特征在于该化合物具有通式I，而且L2选自β-烯醇根，氨基羧酸根，亚氨基羧酸根，水杨酸根，羟基喹啉根和二芳基膦基醇根。
7.如权利要求1和3-6中任一项或多项所述的活性层，或权利要求2和4-6中一项或多项所述的器件，其特征在于该化合物具有通式II，而且L3包含选自醇根，羧酸根，硫代羧酸根，二硫代羧酸根，磺酸根，硫醇根，氨基甲酸根，二硫代氨基甲酸根，硫代卡巴腙阴离子，磺酰胺阴离子，卤离子，硝酸根，硫酸根和六卤锑酸根的配位基团。
8.如权利要求1和3-7中任一项或多项所述的活性层，或如权利要求2和4-7中任一项或多项所述的器件，其特征在于至少一种化合物具有通式II，而且L4具有通式XIII，
PAr3                                        (XIII)
其中Ar选自芳基和杂芳基。
9.如权利要求1和3-8中任一项或多项所述的活性层，或如权利要求2和4-8中任一项或多项所述的器件，其特征在于基本上100重量％的活性层包含至少一种具有选自通式I和通式II的通式的化合物。
10.如权利要求2和4-9中任一项或多项所述的器件，其特征在于该活性层是电荷输运层。
11.如权利要求1和3-8中任一项或多项所述的活性层，或如权利要求2和4-10中任一项或多项所述的器件，其特征在于该稀释剂选自聚(N-乙烯基咔唑)；聚硅烷；4，4’-N，N’-二咔唑联苯；和三元芳香胺；或者该稀释剂是一种选自聚亚芳基亚乙烯基，聚芴，聚噁二唑，聚苯胺，聚噻吩，聚吡啶，聚亚苯基它们的共聚物，及它们的组合的共轭聚合物。
12.如权利要求2和4-11中任一项或多项所述的器件，其还包括：
空穴输运层，其选自N，N’-二苯基-N，N’-双(3-甲苯基)-[1，1’-联苯基]-4，4’-二胺；1，1-双[(二-4-甲苯基氨基)苯基]环己烷；N，N’-双(4-甲苯基)-N，N’-双(4-乙苯基)-[1，1’-(3，3’-二甲基)联苯基]-4，4’-二胺；四-(3-甲苯基)-N，N，N’，N’-2，5-亚苯基二胺；α-苯基-4-N，N-二苯基氨基苯乙烯；对-(二乙氨基)苯甲醛二苯腙；三苯基胺；双[4-(N，N-二乙氨基)-2-甲苯基](4-甲苯基)甲烷；1-苯基-3-[对-(二乙氨基)苯乙烯基]-5-[对-(二乙氨基)苯基]吡唑啉；1，2-反式-双(9H-咔唑-9-基)环丁烷；N，N，N’，N’-四(4-甲苯基)-(1，1’-联苯基)-4，4’-二胺；卟啉化合物；及其组合；和/或
电子输运层，其选自三(8-羟基喹啉根合)铝；2，9-二甲基-4，7-二苯基-1，10-菲咯啉；4，7-二苯基-1，10-菲咯啉；2-(4-联苯基)-5-(4-叔丁基苯基)-1，3，4-噁二唑；3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1，2，4-三唑；三(2-苯基吡啶根合)铱；及其组合。
13.一种选自表1所示配合物1-a到1-m的化合物。
14.如权利要求1和3-9中任一项或多项所述的活性层，或如权利要求2和4-12中任一项或多项所述的器件，其特征在于至少一种化合物选自表1所示的配合物1-a到1-m。
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