CN101371377A - 有机场致发光元件 - Google Patents
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Abstract
本发明涉及改善元件的发光效率、充分确保驱动稳定性、且具有简单的构成的有机场致发光元件(有机EL元件)。该有机场致发光元件是在层合于基板上的阳极和阴极之间具有空穴输送层、发光层及电子输送层发光层的有机场致发光元件,该发光层含有磷光发光性掺杂剂和特定结构的吲哚并咔唑化合物作为主体材料。作为该吲哚并咔唑化合物,可例示N,N’-二苯基吲哚并咔唑或双(N-苯基吲哚)咔唑。
Description
技术领域
本发明涉及有机场致发光元件(以下称为有机EL元件),详细地来讲,涉及通过并用磷光发光掺杂剂和具有特定结构的主体化合物来显示高亮度率的有机EL元件。
背景技术
通常,对于有机EL元件而言,作为其最简单的结构是由发光层及夹持该发光层的一对对置电极构成。即,在有机EL元件中,利用如下现象:如果在两电极之间施加电场,从阴极注入电子,从阳极注入空穴,这些物质在发光层中,在复合能级从传导带回到价电子带时形成能量而发出光。
近年来,对使用有机薄膜的EL元件进行了开发。特别是为了提高发光效率,以从电极注入载流子的效率提高为目的进行了电极的种类的最优化,通过在电极之间作为薄膜设置了由芳香族二胺构成的空穴输送层和由8-羟基喹啉铝络合物(以下称为Alq3)构成的发光层的元件的开发,与现有的使用了蒽等的单晶的元件相比,发光效率得到了大幅度的改善,因此,朝着在具有自发光·高速应答性的特征的高性能平板上使用进行。
另外,作为提高元件的发光效率的尝试,也正在研究不使用荧光而使用磷光。以上述的设置了由芳香族二胺构成的空穴输送层和由Alq3构成的发光层的元件为代表的许多元件是利用荧光发光的元件,但如果使用磷光发光、即利用来自三重激发态的发光,则和目前使用了荧光(单态)的元件相比,可期待其效率提高3倍左右。为了该目的而对将香豆素衍生物或二苯甲酮衍生物作为发光层进行了研究,但仅能得到极低的亮度。其后,作为利用三重态的尝试,对使用铕络合物进行了研究,但其也达不到高效率的发光。
专利文献1:特表2003-515897号公报
专利文献2:特开2001-313178号公报
专利文献3:特开2002-305083号公报
专利文献4:特开2002-352957号公报
专利文献5:特开平11-162650号公报
专利文献6:特开平11-176578号公报
作为用于有机EL元件的发光层的磷光发光掺杂剂,在特表2003-515897号公报等中公开有许多。代表性的有三(2-苯基吡啶)铱络合物(以下称为Ir(ppy)3)。
作为用于有机EL元件的发光层中的主体材料而提出来的,是特开2001-313178号公报中介绍的咔唑化合物的CBP。当使用CBP作为绿色磷光发光材料的Ir(ppy)3的主体材料时,由于CBP容易使空穴流动而难以使电子流动的特性,因此电荷注入平衡破坏,过剩的空穴流出至电子输送侧,结果来自Ir(ppy)3的发光效率下降。
作为解决上述问题的手段有:例如如特开2002-305083号公报那样,在发光层和电阻输送层之间设置空穴阻挡层的手段。通过该空穴阻挡层将空穴有效地积蓄在发光层,由此可以提高在发光层中和电子的复合几率,实现发光的高效率化。作为目前通常使用的空穴阻挡材料,可列举2,9-二甲基-4,7-二苯基-1,10-菲咯啉(以下称为BCP)及对苯基苯酚盐-二(2-甲基-8-羟基喹啉-N1,08)铝(以下称为BAlq)。利用这些物质可以防止在电子输送层电子和空穴发生复合,但由于BCP即使在室温下也容易结晶、作为材料的可靠性欠缺,因此元件的寿命极短。另外,虽然BAlq的Tg为约100℃和报道为比较良好的元件寿命结果,但空穴阻挡能力不充分,来自Ir(ppy)3的发光效率下降。而且还存在因层构成增加一层而使得元件结构变复杂、成本增加的问题。
另一方面,特开2002-352957号公报中介绍的3-苯基-4-(1’-萘基)-5-苯基-1,2,4-三唑(以下称为TAZ)也提出作为磷光有机EL元件的主体材料,但由于容易使电子流动而难以使空穴流动的特性,发光区域成为空穴输送层侧。因此,可以认为,由于空穴输送层的材料引起与Ir(ppy)3的相容性问题,由此导致来自Ir(ppy)3的发光效率下降。例如,从高性能、高可靠性、长寿命的方面考虑作为空穴输送层最好使用的4,4’-双(N-(1-萘基)-N-苯基氨基)联苯(以下称为NPB)存在的问题为:其和Ir(ppy)3的相容性差,发生从Ir(ppy)3向NPB的能量跃迁,发光效率下降。
另外,特开平11-162650号公报及特开平11-176578号公报中公开的吲哚并咔唑化合物被推荐作为空穴输送材料使用,还表明了化合物的稳定性,但没有教导作为磷光主体材料使用。
发明内容
发明要解决的技术问题
为了将有机EL元件应用于平板显示器等的显示元件,必须在改善元件的发光效率的同时充分确保驱动时的稳定性。本发明的目的在于,鉴于上述现状,提供高效率且具有高驱动稳定性的实用上有用的有机EL元件。
用于解决问题的手段
本发明人等进行了潜心研究,结果发现,通过将具有特定结构的吲哚并咔唑骨架的化合物作为磷光主体材料可以解决上述技术问题,以至完成了本发明。
本发明的在层合于基板上的阳极和阴极之间具有发光层的有机场致发光元件,在发光层含有磷光发光性掺杂剂和下述通式(1)所示的化合物作为主体材料。
这里,
环A表示和邻接环缩合的式(1a)表示的芳香环或杂环,
环B表示和邻接环缩合的式(1b)表示的杂环,
X表示碳或氮,
R1、R5表示不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基,
R4表示氢、不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基、或和包含X的环缩合的环,
R2、R3表示氢、烷基、芳烷基、烯基、炔基、氰基、二烷基氨基、二芳基氨基、二芳烷基氨基、氨基、硝基、酰基、烷氧羰基、羧基、烷氧基、烷基磺酰基、卤代烷基、羟基、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。
作为通式(1)表示的化合物,为下述通式(2)或者(3)表示的化合物。
这里,
环A’表示和邻接环缩合的式(2a)表示的芳香环或杂环,
环B表示和邻接环缩合的式(2b)表示的杂环,
R14表示氢、不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基,
X、R1~R3、R5和上述的含义相同。
这里,
环C表示和邻接环缩合的式(3a)表示的芳香环或杂环,
环D表示和邻接环缩合的式(3b)表示的杂环,
环E表示和邻接环缩合的式(3c)表示的杂环,
X表示碳或氮,
R6、R11、R12独立地和R1的含义相同,
R10和R14的含义相同,
R7~R9独立地和R2的含义相同。
在通式(2)或(3)中,环A’或环C为苯环、R1、R5、R6、R11、R12为取代或未取代的苯基或吡啶基、且R2、R3、R7、R8、R9为氢或苯基的化合物可产生优异的有机场致发光元件。
本发明的有机场致发光元件,优选在阳极和发光层之间有空穴注入输送层、在阴极和发光层之间有电子注入输送层。此外,优选在发光层和电子注入输送层之间具有空穴阻挡层。
在本发明中,作为磷光主体材料,使用上述通式(1)表示的化合物。在通式(1)表示的化合物中,作为优选化合物有通式(2)或(3)表示的化合物。在通式(1)中,环A表示和邻接环缩合的式(1a)表示的芳香环或杂环,环B表示和邻接环缩合的式(1b)表示的杂环。在通式(2)中,环A’表示和邻接环缩合的式(2a)表示的芳香环或杂环,环B表示和邻接环缩合的式(2b)表示的杂环。在通式(3)中,环C表示和邻接环缩合的式(3a)表示的芳香环或杂环,环D表示和邻接环缩合的式(3b)表示的杂环,环E表示和邻接环缩合的式(3c)表示的杂环。式(1a)、(2a)及式(3a)中,X为碳或氮,但优选为碳。
式中,R1、R5~R6、R11~R12独立地表示不是稠环结构的取代或未取代的芳香族烃基、不是稠环结构的取代或未取代的芳香族杂环基。作为芳香族烃基,可例举苯基、联苯基。R10、R14独立地除可以为这些芳香族烃基或芳香族杂环基之外,还可以为氢。R4除可以为这些芳香族烃基或芳香族杂环基或氢之外,也可以为缩合在式(1a)、(2a)、(3a)中的含有X的6元环上的环。在为环的情况下,该环也可以为稠环。作为其为环的情况的例子,有式(3)表示的具有稠环的环E。优选为可以具有R9的吲哚环,此时,含氮环缩合在含有X的6元环上。
R2、R3、R7、R8、R9独立地表示氢、烷基、芳烷基、烯基、炔基、氰基、二烷基氨基、二芳基氨基、二芳烷基氨基、氨基、硝基、酰基、烷氧羰基、羧基、烷氧基、烷基磺酰基、卤代烷基、羟基、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。这里,在这些基团为具有脂肪族烃链的情况下,碳数可以为1~4的范围;在具有芳香族基团或芳香族基团和脂肪族烃链的情况下,碳数可以为5~12的范围。
本发明中使用的通式(1)、(2)或(3)表示的化合物可以通过公知的方法容易地制造。例如,通式(2)表示的化合物可以参考Synlett,2005,No.1,p42-48所示的合成例通过以下的反应式来制造。
通式(1)、(2)或(3)表示的化合物的优选具体例如下所示,但并不限于这些物质。赋予化学式的编号为化合物编号。
作为发光层中的磷光发光掺杂剂,可以是含有有机金属络合物的物质,所述有机金属络合物含有选自钌、铑、钯、银、铼、锇、铱、铂和金中的至少一种金属。这样的有机金属络合物在上述专利文献等中是公知的,可以选择使用这些化合物。
作为优选的磷光发光掺杂剂,可例举具有Ir等的贵金属元素作为中心金属的Ir(ppy)3等的络合物类、Ir(bt)2·acac3等的络合物类、PtOEt3等的络合物类。这些络合物的具体例如下所示,但并不限于下述的化合物。
上述磷光发光掺杂剂在发光层中的含量优选在5~10重量%的范围。
附图说明
图1为有机EL元件的示意图
符号的说明
1 基板
2 阳极
3 空穴注入层
4 空穴输送层
5 发光层
6 电子输送层
7 阴极
具体实施方式
下面,对将上述通式(1)表示的化合物用于磷光主体材料的本发明的有机EL元件进行说明。
本发明的有机EL元件是在层合于基板上的阳极和阴极之间具有至少1层发光层的有机EL元件,该发光层含有磷光发光性掺杂剂和通式(1)、优选通式(2)或(3)表示的化合物作为主体材料。
下面,对本发明的有机EL元件的结构,一边参照附图一边进行说明,但本发明的有机EL元件的结构不受这些图示的任何限制。
图1是示意地表示在本发明中使用的一般的有机EL元件的一个结构例的图,1表示基板、2表示阳极、3表示空穴注入层、4表示空穴输送层、5表示发光层、6表示电子输送层、7表示阴极。在本发明的有机EL元件中,具有基板、阳极、发光层及阴极作为必须的层,但除了必须的层以外的层,可以具有空穴注入输送层、电子注入输送层,进一步可以在发光层和电子注入输送层之间具有空穴阻挡层。需要说明的是,空穴注入输送层是指空穴注入层和空穴输送层的任一方或双方,电子注入输送层是指电子注入层和电子输送层的任一方或双方。
需要说明的是,也可以是和图1相反的结构,即,在基板1上依次层合阴极7、电子输送层6、发光层5、空穴输送层4、阳极2,还可以在如上所述的至少一个基板透明性高的2个基板之间设置本发明的有机EL元件。该情况下,可以根据需要追加层或省略层。
本发明有机EL元件可以应用于单一的元件、由配置成阵列状的结构构成的元件、阳极和阴极配置成X-Y矩阵状的结构的任一种。根据本发明的有机EL元件,通过使发光层含有具有特定的骨架的化合物和磷光发光掺杂剂,可以得到与目前使用来自单态的发光的元件相比发光效率高、且驱动稳定性也得到大大改善的元件,可以在全色或多彩的面板的应用中发挥优异的性能。
实施例
下面,通过实施例来更详细说明本发明,但本发明并不限于这些实施例。
实施例1
用荧光测定装置评价作成的薄膜。激发波长使用示例化合物1的极大吸收波长,观察此时发出的光,和单独用化合物1的薄膜的情况下发出的光进行比较。结果示于表1。
实施例2
在实施例1中,除用化合物5代替化合物1外,同样作成薄膜。结果示于表1。
比较例1
实施例1中,除用Alq3代替化合物1外,同样作成薄膜。结果示于表1。
表1
来自主体的发光 | 来自掺杂剂的发光 | |
实施例1 | × | ○ |
实施例2 | × | ○ |
比较例1 | ○ | × |
得知,在发光层的主体材料使用化合物1或化合物5的情况下,在Ir(ppy)3上发生能量跃迁,可观察到来自Ir(ppy)3的发光,但在使用Alq3的情况下,在Ir(ppy)3上没有发生能量跃迁,Alq3自身发出荧光。
实施例3
在图1中,作成省略了空穴注入层、追加了电子注入层的构成的有机EL元件。在形成了膜厚150nm的由ITO构成的阳极的玻璃基板上,利用真空蒸镀法,在真空度4.0×10-4Pa下使各薄膜层合。首先,在ITO上形成60nm厚的NPB作为空穴输送层。
其次,在空穴输送层上,将化合物1和Ir(ppy)3由不同的蒸镀源进行共蒸镀,形成25nm的厚作为发光层。此时,Ir(ppy)3的浓度为7.0%。接着形成50nm厚的Alq3作为电子输送层。进一步在电子输送层上,形成0.5nm厚的氟化锂(LiF)作为电子注入层。最后,在电子注入层上,形成170nm厚的铝(Al)作为电极,作成有机EL元件。
在得到的有机EL元件上连接外部电源、施加直流电压,结果可以确认具有表2所示的发光特性。在表2中,亮度、电压及发光效率表示在10mA/cm2下的值。需要说明的是,得知元件发光谱图的极大波长为517nm,可得到来自Ir(ppy)3的发光。
比较例2
除使用HMTPD作为空穴输送层、使用TAZ作为发光层的主要成分以外,和实施例3同样,作成有机EL元件。
比较例3
除使用TAZ作为发光层的主要成分以外,和实施例3同样,作成有机EL元件。
结果示于表2。
表2
亮度(cd/m2) | 电压(V) | 视觉发光效率(1m/W) | |
实施例3 | 2387 | 7.8 | 9.6 |
比较例2 | 2050 | 13.2 | 4.9 |
比较例3 | 1270 | 9.5 | 4.2 |
产业上的可利用性
本发明的有机EL元件可以在低电压下以高亮度·高效率进行发光。因此,可认为本发明的有机EL元件应用于平板显示器(例如OA计算机用或壁挂电视)、车载显示元件、作为手提电话显示或面发光体发挥特征的光源(例如复印机的光源、液晶显示器或仪表类的背光光源)、显示屏、标识灯,其技术价值大。
Claims (5)
1.有机场致发光元件,其是在层合于基板上的阳极和阴极之间具有发光层的有机场致发光元件,其特征在于,所述发光层含有磷光发光性掺杂剂和下述通式(1)表示的化合物作为主体材料,
式中,环A表示和邻接环缩合的式(1a)表示的芳香环或杂环,环B表示和邻接环缩合的式(1b)表示的杂环,X表示碳或氮,R1、R5表示不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基,R4表示氢、不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基、或和包含X的环缩合的环,R2、R3表示氢、烷基、芳烷基、烯基、炔基、氰基、二烷基氨基、二芳基氨基、二芳烷基氨基、氨基、硝基、酰基、烷氧羰基、羧基、烷氧基、烷基磺酰基、卤代烷基、羟基、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。
2.如权利要求1所述的有机场致发光元件,其是在层合于基板上的阳极和阴极之间具有发光层的有机场致发光元件,所述发光层含有磷光发光性掺杂剂和下述通式(2)或者(3)表示的化合物作为主体材料,
式中,环A’表示和邻接环缩合的式(2a)表示的芳香环或杂环、环B表示和邻接环缩合的式(2b)表示的杂环,X表示碳或氮,R1、R5表示不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基,R14表示氢、不是稠环结构的取代或未取代的芳香族烃基或芳香族杂环基,R2、R3表示氢、烷基、芳烷基、烯基、炔基、氰基、二烷基氨基、二芳基氨基、二芳烷基氨基、氨基、硝基、酰基、烷氧羰基、羧基、烷氧基、烷基磺酰基、卤代烷基、羟基、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基;
式中,环C表示和邻接环缩合的式(3a)表示的芳香环或杂环,环D表示和邻接环缩合的式(3b)表示的杂环,环E表示和邻接环缩合的式(3c)表示的杂环,X表示碳或氮,R6、R11、R12独立地和R1的含义相同,R10和R14的含义相同,R7、R8、R9独立地和R2的含义相同。
3.如权利要求2所述的有机场致发光元件,其中,在通式(2)或(3)中,环A’或环C为苯环,R1、R5、R6、R11、R12为取代或未取代的苯基或吡啶基,且R2、R3、R7、R8、R9为氢或苯基。
4.如权利要求1或2所述的有机场致发光元件,其中,在阳极和发光层之间具有空穴注入输送层,在阴极和发光层之间具有电子注入输送层。
5.如权利要求3所述的有机场致发光元件,其中,在发光层和电子注入输送层之间具有空穴阻挡层。
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- 2006-11-27 CN CNA200680044883XA patent/CN101371377A/zh active Pending
- 2006-11-27 KR KR1020087016107A patent/KR20080085000A/ko not_active Application Discontinuation
- 2006-11-27 EP EP06833362A patent/EP1956666A4/en not_active Withdrawn
- 2006-11-27 US US12/085,348 patent/US20090295276A1/en not_active Abandoned
- 2006-11-27 TW TW095143778A patent/TW200735709A/zh unknown
- 2006-11-27 WO PCT/JP2006/323558 patent/WO2007063796A1/ja active Application Filing
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Also Published As
Publication number | Publication date |
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WO2007063796A1 (ja) | 2007-06-07 |
KR20080085000A (ko) | 2008-09-22 |
US20090295276A1 (en) | 2009-12-03 |
JPWO2007063796A1 (ja) | 2009-05-07 |
EP1956666A4 (en) | 2010-06-16 |
TW200735709A (en) | 2007-09-16 |
EP1956666A1 (en) | 2008-08-13 |
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