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CN101511834B - 有机场致发光元件用化合物及有机场致发光元件 - Google Patents

有机场致发光元件用化合物及有机场致发光元件 Download PDF

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CN101511834B
CN101511834B CN2007800323985A CN200780032398A CN101511834B CN 101511834 B CN101511834 B CN 101511834B CN 2007800323985 A CN2007800323985 A CN 2007800323985A CN 200780032398 A CN200780032398 A CN 200780032398A CN 101511834 B CN101511834 B CN 101511834B
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甲斐孝弘
古森正树
山本敏浩
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Abstract

提供元件发光效率得到改善、充分确保驱动稳定性并且具有简单的结构的有机场致发光元件(有机EL元件)。本发明的有机EL元件为在基板上叠层设置的阳极和阴极之间具有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吲哚并咔唑衍生物作为主体材料。作为吲哚并咔唑化合物，可以例示以下式(2)或(3)表示的化合物。式中，X为N或CH，X的至少1个为N，Ar1～Ar3为可以具有取代基的芳香族基。

Description

有机场致发光元件用化合物及有机场致发光元件
技术领域
本发明涉及新型有机场致发光元件用化合物及有机场致发光元件(以下称为有机EL元件)，更详细地说，涉及通过同时使用磷光发光掺杂剂和具有特定结构的主体化合物而显示高亮度率的有机EL元件。
背景技术
一般地说，有机EL元件最简单的结构是由发光层和夹持该层的一对对向电极构成。即，对有机EL元件而言，利用如下现象：在两电极间施加电场时，电子从阴极注入，空穴从阳极注入，它们在发光层中再结合能级从传导带返回价电子带时发出作为能量的光。
近年来已开始进行使用了有机薄膜的EL元件的开发。特别是为了提高发光效率，以提高来自电极的载流子的注入效率为目的，对电极种类进行了最优化，通过开发将由芳香族二胺形成的空穴传输层和由8-羟基喹啉铝络合物(以下称为Alq3)形成的发光层作为薄膜设置在电极间的元件，与以往使用了蒽等的单晶的元件相比大幅度改善了发光效率，因此以向具有自发光、高速响应性特征的高性能平板的实际应用为目标而不断发展。
另外，作为提高元件发光效率的尝试，还在研究使用不是荧光而是磷光。以上述设置了由芳香族二胺形成的空穴传输层和由Alq3形成的发光层的元件为首的很多元件利用了荧光发光，然而，如果使用磷光发光，即利用来自三重线激发态的发光，与以往使用了荧光(单线态)的元件相比，可望提高3倍左右的效率。为此目的，研究了以香豆素衍生物、二苯甲酮衍生物为发光层，但只得到极低的亮度。其后，作为利用三线态的尝试，虽然研究了使用铕络合物，但其也没有实现高效率的发光。
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
在专利文献1等中公开了大量在有机EL元件的发光层中使用的磷光发光掺杂剂。代表性地，有三(2-苯基吡啶)铱络合物(以下，称为Ir(ppy)3)。
作为有机EL元件的发光层中使用的主体材料提出的是专利文献2中介绍的咔唑化合物CBP。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具有空穴容易流过，电子难以流过的特性，电荷注入平衡破坏，过剩的空穴在电子传输层侧流出，其结果来自Ir(ppy)3的发光效率降低。
作为上述问题的解决手段，例如在专利文献3中，提出了在发光层和电子传输层之间设置空穴阻挡层的方式。通过借助该空穴阻挡层在发光层中高效地蓄积空穴，从而提高在发光层中与电子的再结合几率，能够实现发光的高效率化。作为现在一般使用的空穴阻挡材料，可以例示2，9-二甲基-4，7-二苯基-1，10-菲绕啉(以下称为BCP)以及对-苯基苯酚盐-双(2-甲基-8-喹啉酚盐-N1，O8)铝(以下称为BAlq)。借此能够防止在电子传输层发生电子和空穴再次结合，但由于BCP即使在室温下也容易发生结晶，作为材料的可靠性欠缺，元件的寿命非常短。另外，BAlq的Tg为约100℃和比较良好的元件寿命结果已有报道，但空穴阻挡能力不足，来自Ir(ppy)3的发光效率降低。
另一方面，专利文献4中介绍的3-苯基-4(1’-萘基)-5-苯基-1，2，4-三唑(以下称为TAZ)也作为磷光有机EL元件的主体材料提出，由于电子容易流过，空穴难以流过的特性，发光区域变成空穴传输层侧。因此，还要考虑由于因空穴传输层材料的不同与Ir(ppy)3的相容性问题，来自Ir(ppy)3的发光效率降低。例如，从高性能、高可靠性、高寿命方面考虑，作为空穴传输层最常用的4，4’-双(N-(1-萘基)-N-苯基氨基)联苯(以下称为NPB)，与Ir(ppy)3的相容性差，具有产生从Ir(ppy)3向NPB的能量迁移，发光效率降低的问题。
另外，专利文献5和6中公开的吲哚并咔唑化合物建议作为空穴传输材料使用，还赞扬了化合物的稳定性，但没有教导用作磷光主体材料。另外，化合物的结构也与本发明的化合物不同。
发明内容
发明要解决的问题
为了将有机EL元件应用于平板显示器等的显示元件，在改善元件发光效率的同时，需要充分地确保驱动时的稳定性。鉴于上述现状，本发明的目的在于提供具有高效率和高驱动稳定性的可应用于实际使用的有机EL元件以及适于其的化合物。
解决问题的方式
本发明人经过锐意研究结果发现，通过在有机EL元件中使用特定结构的化合物，能够解决上述问题，从而完成本发明。
即，本发明通过使用特定的吲哚并咔唑骨架的化合物，提供具有高效率和高驱动稳定性的可应用于实际使用的有机EL元件。
本发明的有机场致发光元件用化合物用下述通式(1)表示。
Figure G2007800323985D00031
其中，环A表示与邻接环在任意位置稠合的式(1a)表示的杂环，X表示N或CH，X中至少一个为氮原子。Ar1～Ar3独立地表示不是稠环结构的取代或未取代的芳族烃基或芳族杂环基，Ar2、Ar3可以与含有X的环形成稠合环。R表示氢或1价的取代基。
在通式(1)表示的有机场致发光元件用化合物中，具有下述通式(2)或(3)表示的化合物。
Figure G2007800323985D00041
通式(2)和(3)中，X以及Ar1～Ar3与通式(1)中的X以及Ar1～Ar3的含义相同。
另外，本发明为具有含上述有机场致发光元件用化合物的有机层的有机场致发光元件。有利地，为以下有机场致发光元件，其是在基板上叠层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，该发光层含有磷光发光性掺杂剂和作为主体材料的上述通式(1)、(2)或(3)表示的有机场致发光元件用化合物。
附图说明
图1表示示出有机EL元件一例的截面示意图。
符号说明
1基板、2阳极、3空穴注入层、4空穴传输层、5发光层、6电子传输层、7阴极
具体实施方式
以下详细地说明本发明的实施方式。
本发明的有机EL元件用化合物由上述通式(1)表示。通式(1)表示的化合物具有咔唑环和吲哚环稠合的吲哚并咔唑骨架。此外，含有3个X的环(称为X含有环)与咔唑环的N键合，各环具有键合了R或者Ar1～Ar3的结构。另外，吲哚环为环A和苯环的稠合环。
式中，环A表示与邻接环稠合的式(1a)表示的杂环。这里，式(1a)表示的杂环可在邻接的咔唑环的任意位置稠合。具体地说，可在咔唑环的2，3-位、3，4-位或4，5-位的位置稠合。
与咔唑环的N键合的X含有环中，X表示CH或N，至少1个X为氮原子。优选地，1、2或3个X是氮原子。
Ar1～Ar3表示非稠环结构的取代或未取代的芳族烃基或非稠环结构的取代或未取代的芳族杂环基。作为优选的未取代的芳族烃基，可以例举苯基、联苯基、联三苯基、联四苯基等。作为优选的未取代的芳族杂环基，可以例举吡啶基、嘧啶基、三嗪基、咪唑基、噻吩基等。
这些芳族烃基或芳族杂环基具有取代基时，作为优选的取代基，可以例举C1～C4的烷基、C1～C4的烷氧基、苯氧基、烷硫基、取代氨基、乙酰基等。另外，可以例举碳原子数为5～18的芳族烃基和碳原子数为3～17的芳族杂环基等。
另外，Ar2或Ar3可以与X含有环稠合形成稠合环。
与咔唑环的N键合的X含有环中，当该环为吡啶环时，通式(1)中，优选相对于与咔唑环的N键合的碳，对位的X为氮，其为嘧啶环时，优选邻位的2个X为氮。
R表示氢或1价的取代基。R独立地为氢或烷基、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、烷氧基羰基、羧基、烷氧基、烷基磺酰基、卤代烷基、羟基、酰氨基、取代或未取代的芳族烃基或芳族杂环基。作为优选的1价的取代基，可以例举C1～C4的烷基、C1～C4的烷氧基、苯氧基、烷硫基、取代的氨基、乙酰基等。另外，优选例举取代或未取代的碳原子数为5～18的芳族烃基或碳原子数为3～17的芳族杂环基。
上述通式(1)表示的化合物中，作为优选的化合物，有上述通式(2)和(3)表示的化合物。此外，通式(2)和(3)中的X、Ar1～Ar3以及R与通式(1)中的X、Ar1～Ar3以及R对应，表示同样的含义。对于优选的X、Ar1～Ar3以及R也与以上所述的相同。另外，所谓含义相同，是指这些记号的定义相同，这些记号存在多个时，在上述定义的范围内可以相互变化。
本发明的有机EL元件用化合物可以用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中所示的合成例根据以下反应式进行制备。
Figure G2007800323985D00061
另外，通式(3)可以参考Archiv der Pharmazie(Weinheim，Germany)，1987，320(3)，p280-2所示的合成例根据以下反应式进行制备。下式中，L具有与Ar1～Ar3相同的含义。
Figure G2007800323985D00071
以下示出通式(1)或(2)、(3)表示的化合物的优选具体例，但并不限于这些化合物。
Figure G2007800323985D00072
Figure G2007800323985D00081
Figure G2007800323985D00091
Figure G2007800323985D00101
Figure G2007800323985D00131
Figure G2007800323985D00141
Figure G2007800323985D00151
Figure G2007800323985D00161
Figure G2007800323985D00171
本发明的有机场致发光元件用化合物，通过含有在有机EL元件的有机层中，得到优异的有机场致发光元件。有利地，可以在选自发光层、空穴传输层、电子传输层以及空穴阻挡元件层中的至少一个有机层中含有该有机场致发光元件用化合物。更优选地，可作为含有磷光发光掺杂剂的发光层的主体材料而含有该有机场致发光元件用化合物。
有利地，本发明的有机场致发光元件为叠层在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，该发光层含有磷光发光性掺杂剂、和上述有机EL元件用化合物作为主体材料。有机EL元件的结构只要具有基板、阳极、阴极以及发光层即可，但优选在阳极和发光层之间具有空穴注入传输层以及在阴极和发光层之间具有电子注入传输层。此外，优选在发光层和电子注入传输层之间具有空穴阻挡层。
作为发光层中的磷光发光掺杂剂材料，可以含有含选自钌、铑、钯、银、铼、锇、铱、铂以及金中的至少一种金属的有机金属络合物。涉及的有机金属络合物在前述专利文献等中公知，可以从这些络合物中选择使用。
作为优选的磷光发光掺杂剂，可以例举具有Ir等贵金属元素作为中心金属的Ir(ppy)3等络合物类、Ir(bt)2.acac3等络合物类、PtOEt3等络合物类。以下示出这些络合物类的具体例子，但并不限于下列化合物。
Figure G2007800323985D00181
前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。
其次，参照附图对本发明的有机EL元件的结构进行说明，但本发明的有机EL元件的结构不限于图示内容。
图1是示意地表示用于本发明的一般的有机EL元件的结构例的截面图，附图标记分别表示：1为基板、2为阳极、3为空穴注入层、4为空穴传输层、5为发光层、6为电子传输层、7为阴极。本发明的有机EL元件中，具有基板、阳极、发光层和阴极作为必需的层，但除了必需的层以外，可以具有空穴注入传输层、电子注入传输层，还可以在发光层和电子注入传输层之间具有空穴阻挡层。另外，空穴注入传输层意指空穴注入层和空穴传输层的任一种或者两者，电子注入传输层意指电子注入层和电子传输层的任一种或者两者。
另外，也可以为与图1相反的结构，即在基板1上以阴极7、电子传输层6、发光层5、空穴传输层4、阳极2的顺序叠层，如前已述，也可以在至少一方是高透明性的2片基板之间设置本发明的有机EL元件。这种情形下，可以根据需要追加或省略层。
本发明可适用于有机EL元件为单一元件、由配置为阵列状的结构形成的元件、以及阳极和阴极配置为X-Y矩阵状的结构的任一种。本发明的有机EL元件，通过使发光层中含有具有特定骨架的化合物和磷光发光掺杂剂，得到的元件与以前使用来自单线态的发光的元件相比，发光效率高并且驱动稳定性也得到大幅改善，可在全色或多色的显示屏中应用上发挥优异的性能。
实施例
以下通过实施例对本发明进行更详细的说明，当然本发明并不限于这些实施例，只要不超过本发明的要旨，可以以各种形式实施。另外，化合物序号对应于上述化学式所带的序号。
实施例1
在脱气氮置换的2000ml三口烧瓶中加入33.3g(297.0mmol)的1，2-环己二酮、86.0g(594.7mmol)的苯基肼盐酸盐，向其加入1000ml的乙醇并搅拌。之后，在同一烧瓶内用5分钟滴入3.0g(30.6mmol)的浓硫酸。之后，加热到65℃，搅拌4小时。冷却至室温后，滤取生成的紫茶色结晶后，将滤取的结晶用500ml的乙醇进行两次再成浆(reslurry)洗涤。将其减压干燥，得到80.0g(280.5mmol、收率96.3％)的紫茶色粉末。
然后，在1000ml的三口烧瓶中加入72.0g(261.5mmol)的上述紫茶色粉末，向其加入720g的醋酸、72.0g的三氟醋酸并进行搅拌。之后，加热到100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用200ml的醋酸进行漂洗洗涤后，用200ml己烷进行漂洗洗涤。将其减压干燥得到30.0g(117.1mmol，收率44.8％)的白色粉末A’。得到的白色粉末A’为吲哚并[2，3-a]咔唑。
然后，在脱气氮置换的1000ml三口烧瓶中加入26.0g(101.4mmol)的上述得到的白色粉末、122.7g(601.4mmol)的碘代苯、54.7g(287.2mmol)的碘化铜和66.7g(482.6mmol)的碳酸钾，在其中加入800ml的喹啉并搅拌。之后，加热到190℃，搅拌72小时。暂且冷却至室温后，加入500ml的水和500ml的二氯甲烷，进行搅拌后，滤取生成的黄色结晶。将滤液移至2000ml分液漏斗，分层为有机层和水层。用500ml的水对有机层进行三次洗涤，之后，对得到的有机层用硫酸镁进行脱水，一旦过滤分离硫酸镁后，减压馏去溶剂。之后，用柱色谱精制得到13.7g(41.2mmol，收率40.6％)的白色固体A。得到的白色固体A为11-苯基吲哚并[2，3-a]咔唑。
然后，在脱气氮置换的200ml的三口烧瓶中加入12.5g(0.068mol)的三聚氰酰氯、55ml的脱水THF，在冰浴中并在氮气流下进行搅拌。之后，在同一烧瓶中用2小时滴入105.6g(0.186mol)的32％溴化苯基镁THF溶液。滴入过程中的温度保持在15℃以下。滴加结束后，继续搅拌1.5小时。之后，在同一烧瓶内加入80g的甲苯。之后，在冰浴中进行冷却，在同一烧瓶中用15分钟滴入76.5g(0.254mol)的12％HCl水溶液。滴入过程中的温度保持在30℃以下。将烧瓶内的物质移至500ml的分液漏斗中，分层为有机层和水层。利用100ml的水对有机层进行三次洗涤，之后将得到的有机层用硫酸镁进行脱水，一旦过滤分离硫酸镁后，减压馏去溶剂，得到21.1g的粗产品。之后，加入110g的甲醇，搅拌1小时后，过滤分离析出物，用真空干燥机进行减压干燥，得到14.5g(6.5mmol、收率50.2％)的白色固体B。得到的白色固体B为2-氯-4，6-二苯基-1，3，5-三嗪。
然后，在脱气氮置换的2000ml的三口烧瓶中加入2.18g(50.0mmol)的55％氢化钠、70ml的脱水N，N’-二甲基甲酰胺，在氮气流中进行搅拌。将150ml的脱水N，N’-二甲基甲酰胺加入到13.5g(40.6mmol)的上述得到的白色固体A中，使其溶解，之后用10分钟滴加到同一烧瓶内。滴加结束后，继续进行1小时的搅拌。之后，将150ml的脱水N，N’-二甲基甲酰胺加入到10.4g(39.0mmol)的上述得到的白色固体B中，使其溶解，之后用1小时滴加到同一烧瓶内。滴加结束后，继续搅拌3小时。之后，加入600g的水，滤取析出的结晶。用300g的水对滤取的结晶进行两次再成浆，之后，用300g的甲醇进行再成浆。对得到的结晶利用真空干燥机进行减压干燥，得到21.0g的黄色结晶。
然后，在1000ml的烧瓶中加入21.0g的上述得到的黄色结晶、108.6g的THF，使其溶解。在同一烧瓶中滴加660g的甲醇。过滤分离析出物，利用真空干燥机进行减压干燥，得到12.7g(22.6mmol、收率54.6％)的黄色固体(化合物3)。
化合物3的EI-MS(M+1)为563，熔点为263℃。
实施例2
在玻璃基板上通过真空蒸镀法在真空度为4.0×10-4Pa的条件下，从蒸镀源蒸镀化合物3，以0.1nm/秒形成50nm厚度的薄膜。对形成的薄膜利用荧光测定装置进行评价，结果观察到发光。
另外，在玻璃基板上通过真空蒸镀法在真空度为4.0×10-4Pa的条件下，从不同的蒸镀源蒸镀化合物3和Ir(ppy)3，以0.1nm/秒形成Ir(ppy)3的浓度为7.0％并且厚度为50nm的薄膜。用荧光测定装置对该制作的薄膜进行评价。激发波长使用化合物3的最大吸收波长，观察此时发出的光，与单独只有化合物3的薄膜情形下发出的光比较。结果在表1中示出。
比较例1
除了把薄膜的主体材料替换成化合物3并且换成Alq3制作薄膜以外，与实施例2同样地进行评价。将结果示于表1中。
[表1]
  来自主体的发光   来自掺杂剂的发光
  实施例2   ×   ○
  比较例1   ○   ×
可知发光层的主体材料中使用化合物3的情形下，能量向Ir(ppy)3迁移，观察到来自Ir(ppy)3的发光，使用了Alq3的情形下，能量不向Ir(ppy)3迁移，Alq3自身发出荧光。
实施例3
图1中，制作省略空穴注入层、追加电子注入层的结构的有机EL元件。在形成了膜厚150nm的由ITO形成的阳极的玻璃基板上，通过真空蒸镀法，在真空度为4.0×10-4Pa下叠层各薄膜。首先，在ITO上形成60nm厚的作为空穴传输层的NPB。
其次，在空穴传输层上，作为发光层，从不同的蒸镀源共蒸镀化合物3和Ir(ppy)3，形成25nm的厚度。此时，Ir(ppy)3的浓度为7.0wt％。然后，形成50nm厚度的Alq3作为电子传输层。另外，在电子传输层上，形成0.5nm厚度的氟化锂(LiF)作为电子注入层。最后，在电子注入层上，形成170nm厚度的铝(Al)作为电极，从而作成有机EL元件。
将得到的有机EL元件连接外部电源而施加直流电压，结果确认具有表2中的发光特性。在表2中，亮度、电压以及发光效率表示在10mA/cm2下的值。另外可知，元件发光谱的最大波长为517nm，得到来自Ir(ppy)3的发光。
比较例2
除了使用HMTPD作为空穴传输层，使用TAZ作为发光层主体材料以外，与实施例3同样地制作有机EL元件。
比较例3
除了使用TAZ作为发光层的主体材料以外，与实施例3同样地制作有机EL元件。
[表2]
  亮度(cd/m2)   电压(V)   视感发光效率(1m/W)
  实施例3   2720   5.2   16.4
  比较例2   2050   13.2   4.9
  比较例3   1270   9.5   4.2
实施例4
(化合物114的合成)
在脱气氮置换的2000ml的三口烧瓶中加入50.69g(0.2058mol)的3，3’-亚甲基二吲哚、加入30.55g(0.2061mol)的原甲酸三乙酯，向其加入640g的甲醇并搅拌。用3分钟向其中滴入5.0g(0.0515mol)的浓硫酸后，加热回流1小时。冷却至室温后，滤取生成的红茶色结晶，将得到的结晶用500ml的甲醇进行两次再成浆洗涤。减压馏去溶剂，得到36.81g(0.1438mol、收率69.9％)的红茶色粉末状固体C。该固体C为吲哚并[3，2-b]咔唑。
然后，在脱气氮置换的2000ml的三口烧瓶中加入4.36g(100.0mmol)的55％氢化钠、70ml的脱水DMF，在氮气流下搅拌。用10分钟向其滴入10.4g(40.6mmol)上述固体C的脱水DMF(150ml)溶液，滴入结束后，搅拌1小时。然后，用1小时滴入20.9g(78.0mmol)的2-氯-4，6-二苯基-1，3，5-三嗪的脱水DMF(300ml)溶液。滴加结束后，继续搅拌3小时，之后，加入900g的水，滤取析出的结晶。将滤取的结晶用450g的水进行两次再成浆洗涤，再利用450g的甲醇进行再成浆洗涤。减压馏去溶剂后，得到42.0g的褐色结晶。利用THF以及甲醇对其进行晶析精制后，减压馏去溶剂，得到13.4g(18.6mmol，收率46％)的淡褐色固体(化合物114)。
APCI-MS，m/z 719[M+1]+  熔点：498℃。
实施例5
(化合物116的合成)
在脱气氮置换的200ml的三口烧瓶中加入1.3g(5.1mmol)的吲哚并[3，2-b]咔唑、1.4g(14.6mmol)的叔丁醇钠、8.2mg(0.037mmol)的醋酸钯、6.4g(17.9mmol)的2，6-二苯基-4-碘吡啶以及80ml的二甲苯，室温下搅拌1小时。向其加入64mg(0.32mmol)的三叔丁基膦，在120℃下加热搅拌40小时。冷却至室温后，加入70ml的水，滤取析出物。通过用甲醇、甲苯、氯仿依次对得到的固体进行加热再成浆精制，得到1.0g(1.4mmol、收率27.5％)的淡褐色固体(化合物116)。
APCI-MS：m/z 715[M+1]+  熔点：426℃
实施例6
(化合物2的合成)
在脱气氮置换的1000ml的三口烧瓶中加入2.18g(0.056mol)的55％氢化钠、240ml的脱水DMF，在氮气流下进行搅拌。用10分钟向其滴加11-苯基吲哚并[2，3-a]咔唑13.3g(0.04mol)的脱水DMF(25ml)溶液，滴加结束后，搅拌1小时。再用1小时滴加8.8g(0.048mol)的2，4，6-三氯-1，3-嘧啶的脱水DMF(150ml)溶液。滴加结束后，继续搅拌3小时，之后，加入500ml的水，滤取析出的结晶。将滤取的结晶用300g的水进行两次再成浆洗涤，再用300g的甲醇进行再成浆洗涤。减压馏去溶剂，得到18.2g的淡黄色结晶。不对得到的结晶进行精制，用于接下来的反应。
然后，在2000ml的三口烧瓶中加入18.2g(0.038mmol)的上述得到的淡黄色结晶、9.73g(0.08mol)的苯基硼酸、1.84g(0.0016mol)的四(三苯基膦)钯、150ml的乙醇、450ml的甲苯并进行搅拌。之后，加入29.8g(0.28mol)的碳酸钠的水溶液(140ml)，在85℃下搅拌4小时。冷却至室温后，加入200ml的水、200ml的甲苯，分层为有机层和水层，用200ml的水洗涤有机层。用硫酸镁将有机层脱水，过滤分离硫酸镁后，减压馏去溶剂。用二氯甲烷和乙醇对其进行晶析精制后，减压馏去溶剂，得到5.2g(0.0092mol，收率23％)的白色固体(化合物2)。
APCI-MS：m/z 563[M+1]+  熔点：252℃。
实施例7
(化合物29的合成)
在脱气氮置换的100ml的三口烧瓶中加入0.21g(0.94mmol)的醋酸钯(II)、20ml的二甲苯、0.76g(3.76mmol)的三叔丁基膦，在60℃下加热搅拌30分钟。在氮气流下将该溶液传输到加热到60℃的4.61g(0.0180mol)的吲哚并[2，3-a]咔唑、5.8g(0.018mol)的4-咔唑基溴苯以及7.7g(0.080mol)的叔丁氧基钠的甲苯(180ml)溶液中。之后，升温到130℃，在相同温度下加热搅拌5小时。冷却至室温后，加入200ml的水。油水分离后，减压浓缩有机层，得到粗生成物。将其用二氯甲烷和乙醇进行晶析精制后，减压馏去溶剂，得到4.2g(0.0084mol、收率47％)的11-(4-咔唑基苯基)吲哚并[2，3-a]咔唑。
然后，在脱气氮置换的200ml的三口烧瓶中加入0.42g(0.0096mol)的55％氢化钠、10ml的脱水DMF，在氮气流下搅拌。用10分钟滴加4.0g(0.008mol)的上述11-(4-咔唑基苯基)吲哚并[2，3-a]咔唑的脱水DMF(20ml)溶液。滴加结束后，进行1小时程度的搅拌后，用1小时向其滴入2.14g(0.008mol)的2-氯-4，6-二苯基-1，3，5-三嗪的脱水DMF(20ml)溶液。滴加结束后，搅拌3小时后，加入100g的水，滤取析出的结晶。将滤取的结晶用100g的水进行两次再成浆洗涤，再利用100g的甲醇进行再成浆洗涤。减压馏去溶剂，利用THF/甲醇进行晶析精制，得到3.0g(0.0041mol，收率51％)的黄色固体(化合物29)。
APCI-MS：m/z 729[M+1]+  熔点：319℃
实施例8
(化合物37的合成)
在脱气氮置换的2000ml的三口烧瓶中加入4.80g(110.0mmol)的55％氢化钠、70ml的脱水DMF，在氮气流下搅拌。用10分钟向其滴加13.5g(52.7mmol)的吲哚并[2，3-a]咔唑的脱水DMF(150ml)溶液。滴加结束后，进行1小时程度的搅拌后，用1小时向其滴入29.4g(110.0mmol)的2-氯-4，6-二苯基-1，3，5-三嗪的脱水DMF(150)溶液。滴加结束后，搅拌3小时后，加入900g的水，滤取析出的结晶。将滤取的结晶用450g的水进行两次再成浆洗涤，再利用450g的甲醇进行再成浆洗涤。减去馏去溶剂，得到35.0g的结晶。对其利用THF/甲醇进行晶析精制，得到24g(33.4mmol，收率63.4％)的黄色固体(化合物37)。
APCI-MS：m/z 729[M+1]+  熔点：426℃
实施例9
(化合物1的合成)
在脱气氮置换的20ml的三口烧瓶中加入0.071g(0.32mmol)的醋酸钯(II)、二甲苯(5ml)、0.32ml(1.26mmol)的三叔丁基膦，60℃下加热搅拌30分钟。在氮气流下将该溶液传输到加热到60℃的1.99g(0.0060mol)的11-苯基吲哚并[2，3-a]咔唑、2.46g(0.0069mol)的2，6-二苯基-4-碘吡啶以及2.57g(0.0267mol)的叔丁氧基钠的二甲苯(60ml)溶液中。之后，升温到130℃，在相同温度下加热搅拌5小时。冷却至室温后，加入70ml的水。油水分离，减压浓缩有机层，得到4.85g的粗生成物。将其用二氯甲烷和乙醇进行晶析精制后，减压馏去溶剂，得到1.43g(0.0025mol、收率36％)的白色固体化合物。
APCI-MS：m/z 562[M+1]+  熔点：277℃、287℃
实施例10
图1中，制作追加了电子注入层的结构的有机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为4.0×10-4Pa下叠层各薄膜。首先，在ITO上形成20nm厚的酞菁铜(CuPC)作为空穴注入层。其次，形成40nm厚的NPB作为空穴传输层。然后，在空穴传输层上，从不同的蒸镀源共蒸镀化合物3和Ir(ppy)3作为发光层并形成35nm的厚度。此时，Ir(ppy)3的浓度为7.0wt％。其次，形成40nm厚的Alq3作为电子传输层。另外，在电子传输层上形成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，从而制成有机EL元件。
将得到的有机EL元件连接外部电源而施加直流电压，结果确认具有表3中的发光特性。在表3中，亮度、电压以及发光效率表示在10mA/cm2下的值。另外可知，元件发光谱的最大波长为517nm，得到来自Ir(ppy)3的发光。
实施例11～16
除了使用实施例4～8中得到的化合物(化合物No.114、116、2、29、37和1)作为发光层的主成分以外，与实施例10同样地制成有机EL元件。表3示出发光特性。在实施例4～8中得到的所有化合物(化合物No.114、116、2、29、37和1)中，确认得到来自Ir(ppy)3的发光。
[表3]
  化合物No   亮度(cd/m2)   电压(V)   视感发光效率(lm/W)
  实施例10   3   2850   4.9   18.3
  实施例11   114   1970   6.1   10.1
  实施例12   116   3100   7.9   12.3
  实施例13   2   2900   5.5   16.6
  实施例14   29   3320   6.3   16.6
  实施例15   37   2280   6.5   11.0
  实施例16   1   2740   6.7   12.8
工业上利用的可能性
本发明的有机EL元件能够在低电压下以高亮度、高效率发光。因此，考虑将本发明涉及的有机EL元件应用于平板显示器(例如OA电脑用或壁挂电视)、车载显示元件、移动电话显示或利用了面发光体的特征的光源(例如，复印机的光源、液晶显示器以及仪表类背照光光源)、显示板、标识灯，其技术价值大。

Claims (7)

1.下述通式(1)表示的有机场致发光元件用化合物，
Figure FSB00000994363700011
其中，环A表示与邻接环在任意位置稠合的由式(1a)表示的杂环，X表示CH或N，X中至少一个为氮原子，Ar1～Ar3独立地表示非稠环结构的取代或未取代的苯基、联苯基、吡啶基、嘧啶基、三嗪基、咪唑基或噻吩基，Ar1～Ar3具有取代基时，取代基为C1～C4的烷基、C1～C4的烷氧基、碳原子数为5～18的芳族烃基或碳原子数为3～17的芳族杂环基，R表示氢或者C1～C4的烷基、C1～C4的烷氧基、碳原子数为5～18的芳族烃基或碳原子数为3～17的芳族杂环基。
2.下述通式(2)或(3)表示的权利要求1所述的有机场致发光元件用化合物，
Figure FSB00000994363700021
其中，X以及Ar1～Ar3与式(1)以及(1a)中的X以及Ar1～Ar3的含义相同。
3.有机场致发光元件，其具有含有权利要求1～2中任一项所述的有机场致发光元件用化合物的有机层。
4.权利要求3所述的有机场致发光元件，其中，含有有机场致发光元件用化合物的有机层为选自发光层、空穴传输层、电子传输层以及空穴阻挡元件层中的至少一层。
5.权利要求3所述的有机场致发光元件，其中，含有有机场致发光元件用化合物的有机层为在基板上叠层设置的阳极和阴极之间具有发光层的有机场致发光元件的发光层，该发光层含有磷光发光性掺杂剂和作为主体材料的该有机场致发光元件用化合物。
6.权利要求5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传输层，在阴极和发光层之间具有电子注入传输层。
7.权利要求6所述的有机场致发光元件，其中，在发光层和电子注入传输层之间具有空穴阻挡层。
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