CN102633820B - 有机电致发光元件用化合物及有机电致发光元件 - Google Patents

有机电致发光元件用化合物及有机电致发光元件 Download PDF

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CN102633820B
CN102633820B CN201210072915.4A CN201210072915A CN102633820B CN 102633820 B CN102633820 B CN 102633820B CN 201210072915 A CN201210072915 A CN 201210072915A CN 102633820 B CN102633820 B CN 102633820B
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organic electroluminescent
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古森正树
山本敏浩
甲斐孝弘
堀田正则
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Abstract

本发明涉及一种有机电致发光元件(有机EL元件)以及其使用的化合物，所述有机电致发光元件改善元件的发光效率、充分确保驱动稳定性，且具有简单的结构。该有机电致发光元件是在被层合于基板上的阳极和阴极之间具有发光层的有机电致发光元件，该发光层含有磷光发光性掺杂剂和有机电致发光元件用化合物作为主体材料，所述有机电致发光元件用化合物具有2个以上吲哚咔唑骨架。其使用的吲哚咔唑化合物可例示如下述式表示的化合物。

Description

有机电致发光元件用化合物及有机电致发光元件
本专利申请为在2006年11月22日提出申请的专利申请号为200680045030.8、名称为“有机电致发光元件用化合物及有机电致发光元件”的专利申请的分案申请。
技术领域
本发明涉及一种新的有机电致发光元件用化合物及有机电致发光元件(以下称为有机EL元件)，详细地来讲，涉及一种通过并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的有机EL元件。
背景技术
通常，有机EL元件，作为其最简单的结构是由发光层及夹持该层的一对对置电极构成。即，在有机EL元件中，利用的是如下现象，即当在两个电极间施加电场时，从阴极注入电子，从阳极注入空穴，它们在发光层中，在复合能级从传导带返回到价电子带时作为能量发出光。
近年来，对使用了有机薄膜的EL元件进行了开发。特别是为了提高发光效率，通过以下元件的开发，即，为了提高从电极注入载流子的效率而对电极的种类进行最佳化，在电极间作为薄膜设置由芳香族二胺形成的空穴输送层和由8-羟基喹啉铝配合物(以下称为Alq3)形成的发光层，由此与现有的使用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，以实用于具有自发光·高速应答性的特征的高性能平板为目标取得了进展。
另外，作为提高元件的发光效率的尝试，还正在对不使用荧光而使用磷光进行研究。以上述的设置有由芳香族二胺形成的空穴输送层和由Alq3形成的发光层的元件为代表的许多元件利用的是荧光发光，但是，如果使用磷光发光、即利用来自三重激发态的发光，则与目前使用荧光(单态)的元件相比，可期待3倍左右的效率提高。为了这个目的，对将香豆素衍生物、二苯甲酮衍生物作为发光层进行了研究，但只得到非常低的亮度。其后，作为利用三重态的尝试，对使用铕配合物进行了研究，但其也达不到高效率的发光。作为磷光发光掺杂剂，多数进行的是如特表2003-515897号公报(专利文献1)所例举的发明。
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
在有机EL元件开发中，作为用于发光层的主体材料而提出的方案是特开2001-313178号公报中介绍的咔唑化合物的CBP。如果使用CBP作为绿色磷光发光材料的三(2-苯基吡啶)铱配合物(以下称为Ir(ppy)3)的主体材料，由于CBP容易使空穴流动而难以使电子流动的特性，电荷注入平衡瓦解，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。
作为上述的解决手段，有例如如特开2002-305083号公报那样在发光层和电子输送层间设置空穴阻挡层的手段。通过该空穴阻挡层将空穴高效率地积蓄在发光层中，由此可以提高和发光层中的电子的复合几率，达到发光的高效率化。作为目前通常使用的空穴阻挡材料，可例举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-二(2-甲基-8-羟基喹啉-N1，08)铝(以下称为BAlq)。由此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，欠缺作为材料的可靠性，因此元件寿命极其短。另外，报告有BAlq的Tg为约100℃和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。
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)也被提出作为磷光有机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，发光领域成为空穴输送层侧，因此也可以认为，因空穴输送层的材料而导致与Ir(ppy)3的相容性问题，由此来自Ir(ppy)3的发光效率下降。例如，从高性能、高可靠性、长寿命的观点考虑，作为空穴输送层最好使用的4，4’-双(N-(1-萘基)-N-苯氨基)联苯(以下称为NPB)存在的问题如下，即其与Ir(ppy)3的相容性差，从Ir(ppy)3向NPB发生能量转换，发光效率下降。
另外，特开平11-162650号公报及特开平11-176578号公报中对吲哚咔唑化合物进行了公开，但关于本发明的化合物没有公开。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咔唑化合物被推荐作为空穴输送材料的使用，还强调了化合物的稳定性，但并没有教导作为磷光主体材料的使用。
发明内容
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，鉴于上述现状，目的在于提供一种高效率且具有高驱动稳定性的实用上有用的有机EL元件以及适合其的化合物。
本发明人等进行了潜心研究，结果发现，通过将具有特定的吲哚咔唑骨架的化合物使用于有机EL元件可以解决上述问题，以至完成了本发明。
本发明的有机电致发光元件用化合物由下述通式(1)表示。
在此，Z表示由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组成的连接基团，
n表示2以上的整数，
Y表示下述式(1a)表示的基团；
在此，
环A表示和相邻环缩合的式(1b)表示的芳香族环或杂环，
环B表示和相邻环缩合的式(1c)表示的杂环，
X表示碳或氮，
R43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、或和含有X的环缩合的环，
R44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，
R41、R42表示氢、烷基、芳烷基、链烯基、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、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。
在通式(1)中，当Y为下述式(1d)表示的基团时，可得到优异的有机电致发光元件用化合物。或者，当n为2、3或4时，可得到优异的有机电致发光元件用化合物。
在此，
R45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，
R46具有和R44相同的含义，
R47、R48独立地具有和R41相同的含义。
另外，通式(1)表示的本发明的有机电致发光元件用化合物有下述通式(2)或(3)表示的化合物。
在此，
环A、环A’表示和相邻环缩合的式(2a)表示的芳香环，
环B、环B’表示和相邻环缩合的式(2b)表示的杂环。
在此，
环C、环C’表示和相邻环缩合的式(3a)表示的芳香环，
环D、环D’表示和相邻环缩合的式(3b)表示的杂环，
环E、环E’表示和相邻环缩合的式(3c)表示的杂环。
而且，本发明的有机电致发光元件用化合物有下述通式(4)或(5)表示的化合物。
在此，
环F、环F’表示和相邻环缩合的式(5a)表示的杂环。
在上述通式(2)～(5)及式(2a)～(2c)、(3a)～(3c)、(5a)中，当环A、A’、C、C’为苯环、R6、R14、R15、R22、R23、R30、R31、R32为取代或未取代的苯基或吡啶基、且R1～R4、R7～R12、R16～R21、R24～R29为氢或苯基时，可得到优异的有机电致发光元件用化合物。
在上述通式(1)～(5)及式(1a)～(1d)、(2a)～(2c)、(3a)～(3c)、(5a)中，记号具有以下的意义。
X表示碳或氮，
R5、R13、R17、R20、R45独立地表示氢、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，
R6、R14～R15、R22～R23、R30～R32、R44、R46独立地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，
Ar1～Ar4独立地表示由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组成的2价的连接基团，
R1～R4、R7～R12、R16、R18～R19、R21、R24～R29、R41～R42、R47～R48独立地表示烷基、芳烷基、链烯基、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、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。
另外，本发明为在被层合于基板上的阳极和阴极之间具有发光层的有机电致发光元件，其特征在于，该发光层含有磷光发光性掺杂剂和上述有机电致发光元件用化合物作为主体材料。希望该有机电致发光元件在阳极和发光层之间具有空穴注入输送层以及在阴极和发光层之间具有电子注入输送层。或者希望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，将上述通式(1)表示的化合物、优选通式(2)～(5)表示的化合物的任一种以上用于有机EL元件中的至少一个有机层中。
本发明的有机EL元件用化合物由上述通式(1)表示。通式(1)中，Z表示选自不是稠环结构的取代或未取代的芳香族烃基及不是稠环结构的取代或未取代的芳香族杂环基的连接基团。n表示2以上的整数。而且，Z是n价的基团。
在连接基团Z为芳香族烃基时，作为形成芳香族烃基的芳香族烃环，可优选例举苯环、联苯环、三联苯环等。在为芳香族杂环基时，可优选例举吡啶环、三唑环、二唑环、苯基吡啶环、苯基三唑环、三苯基三唑环等。当这些基团具有取代基时，作为取代基可优选例举碳数1～6的烷基、苯基、吡啶基等。取代基的数以0～4、优选0～2为宜。
Y为上述式(1a)表示的基团。式(1a)中，环A及环B表示和相邻环缩合的环。有利的是Y为上述通式(1d)表示的基团。
在R41、R42为取代或未取代的芳香族烃基或芳香族杂环基时，作为芳香族烃基可优选例举苯基、联苯基等。在为芳香族杂环基时，可优选例举吡啶基。当这些基团具有取代基时，作为取代基可优选例举碳数1～6的烷基、苯基、吡啶基等。取代基的个数以0～4、优选0～2为宜。
在R43或R44为芳香族烃基时，作为芳香族烃基可优选例举苯基、联苯基等。在为芳香族杂环基时，可优选例举吡啶基。当这些基团具有取代基时，作为取代基可例举碳数1～6的烷基、苯基、吡啶基等。取代基的个数以0～4、优选0～2为宜。R43除了可以为上述芳香族烃基或芳香族杂环基以外，还可以为氢或和式(1b)中的含有X的6元环缩合的环，优选为氢或上述环。
在为和式(1b)中的含有X的6元环缩合的环时，该环也可以是稠合环。作为其为稠合环时的例子，有通式(3)及(5)中的具有稠合环的环E、E’及环F、F’。即，优选也可以具有R9、R12、R25或R28的吲哚环。此时，吲哚环中的含氮环与含有X的6元环缩合。
在通式(1)中，由于环A为苯环时成为吲哚咔唑衍生物，因此，本发明的化合物可以称为具有吲哚咔唑单元的化合物。该吲哚咔唑单元是提高空穴输送性的单元，为了进一步提高空穴输送性，n必须为2以上。需要说明的是，对于通式(1)而言，由于通式(1)的化合物包括通式(2)～(5)表示的化合物，因此，在称为通式(1)的化合物时，可理解为含有这些式子表示的化合物的意思。
n优选为2～4，更优选为2～3。n为5以上时，分子量变大，升华性下降，在制作电致发光元件时，有时候在使用蒸镀法的情况下发生障碍或因杂质的高分子量升高而导致难以提纯。
作为n为2的通式(1)所含的化合物有通式(2)～(5)表示的化合物。通式(2)～(5)中出现具有和通式(1)相同含义的记号，优选为与通式(1)所述的同样的基团或环。
对本发明的有机EL元件而言，在层合于基板上的阳极和阴极之间具有发光层，该发光层含有磷光发光性掺杂剂和上述有机EL用化合物作为主体材料。有利的是在阳极和发光层之间具有空穴注入输送层以及在阴极和发光层之间具有电子注入输送层。另外，在发光层和电子注入输送层之间具有空穴阻挡层也是有利的。
更有利的是，本发明的有机EL元件，可以使用在上述通式(1)中Y为通式(1d)表示的化合物或通式(2)～(5)表示的化合物作为主体材料。
通式(1)表示的化合物可以用公知的方法容易地制造。例如，以Tetrahedron，1991，Vol.47，No.37，p7739-7750所示的合成例作为参考，可以通过以下的反应式来制造。
通式(2)表示的化合物可以通过以下的反应式来制造。
另外，通式(1)中，Y为通式(1d)、n＝3的化合物可以通过以下的反应式来制造。
通式(2)～(5)中的Ar1～Ar4表示2价的连接基团。具体而言可例举以下的Y-1～Y-118表示的连接基团。
另外，这些连接基团也可以具有取代基。作为取代基的例子可例举烷基、芳烷基、链烯基、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、酰胺基、取代或未取代的芳香族烃基或芳香族杂环基。
作为取代基的优选例子，可例举以下的Z-1～Z-138表示的取代基。
上述通式(2)～(5)表示的化合物的优选具体例如下所示，但并不限于此。
上述通式(1)表示的Y为通式(1d)、n为3以上的有机EL元件用化合物的优选具体例如下所示，但并不限于此。
本发明的有机EL元件，在发光层中含有磷光发光性掺杂剂和上述有机EL用化合物作为主体材料。作为发光层中的磷光发光掺杂剂材料，可以含有包含选自钌、铑、钯、银、铼、锇、铱、铂及金中的至少一种金属的有机金属配合物。该有机金属配合物在上述专利文献等中是公知的，可以对它们进行选择使用。
作为优选的磷光发光掺杂剂，可例举具有Ir的等贵金属元素作为中心金属的Ir(ppy)3等的配合物类、Ir(bt)2·acac3等的配合物类、PtOEt3等的配合物类。这些配合物类的具体例如下所示，但不限定于下述的化合物。
上述磷光发光掺杂剂在发光层中所含有的量优选为5～10重量％的范围。
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一个的发光层的有机EL元件，该发光层含有磷光发光性掺杂剂和通式(1)表示的化合物。
附图说明
图1是表示有机EL元件的一个实例的示意图。
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，对于本发明的有机EL元件的结构，一边参照附图一边进行说明，但是本发明的有机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通常的有机EL元件的结构例的剖示图，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，可具有空穴注入输送层、电子注入输送层，还可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层或这两层，电子注入输送层是指电子注入层和电子输送层的任一层或这两层。
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，如上所述，还可以在至少一个基板的透明性高的2个基板间设置本发明的有机EL元件。此时，也可以根据需要追加层或省略层。
本发明的有机EL元件可以适用于单一元件、含有以阵列状配置成的结构的元件、阳极和阴极以X-Y矩阵状配置成的结构的任一种。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，可以在全色或多彩面板的应用中发挥优异性能。
实施例
以下，通过实施例更详细说明本发明，但本发明并不限于这些实施例，可以以各种形式进行实施。需要说明的是，化合物编号为对上述化学式赋予的编号。
实施例1
(化合物9的合成)
在进行脱气氮气置换了的200ml三口烧瓶中，加入1，2-环己二酮5.0g(44.59mmol)、苯肼盐酸盐12.9g(89.21mmol)，在其中加入乙醇145ml，进行搅拌。然后，在同一烧瓶内用5分钟滴加浓硫酸0.45g(4.59mmo l)。然后加热至65℃，搅拌4小时。冷却至室温后，滤取生成的紫褐色结晶后，将滤取的结晶用乙醇50ml进行两次再淤浆化洗涤(reslurried)。对其进行减压干燥，得到紫褐色粉末12.0g(43.59mmo l、收率97.7％)。
接着，在300ml三口烧瓶中，加入上述紫褐色粉末12.0g(43.59mmol)，在其中加入乙酸140g、三氟乙酸8.0g，进行搅拌。然后加热至100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用乙酸200ml进行漂洗洗涤后，用己烷200ml进行漂洗洗涤。对其进行减压干燥，得到白色粉末5.0g(19.51mmol、收率44.4％)。
在进行脱气氮气置换了的200ml三口烧瓶中，加入上述得到的白色粉末4.0g(15.61mmol)、4，4’-二碘联苯3.2g(7.88mmol)、碘化铜7.6g(39.91mmol)、碳酸钾9.7g(70.18mmol)，在其中加入喹啉150ml，进行搅拌。然后加热至190℃，搅拌24小时。暂时冷却至室温后，加入碘代苯40.0g(196.07mmol)、碘化铜7.6g(39.91mmol)，加热至190℃，搅拌3天。冷却至室温后，加入水200ml、二氯甲烷200ml，进行搅拌后，滤取生成的黄色结晶。将滤液转移到1000ml分液漏斗，分馏为有机层和水层。将有机层用200ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到白色固体(化合物9)3.0g(3.69mmol、收率46.8％)。
化合物9的EI-MS(M+1)为814、熔点为398℃。
实施例2
(化合物40的合成)
在进行脱气氮气置换了的2000ml三口烧瓶中，加入1，2-环己二酮33.3g(297.0mmol)、苯肼盐酸盐86.0g(594.7mmol)，在其中加入乙醇1000ml，进行搅拌。然后，用5分钟在同一烧瓶内滴加浓硫酸3.0g(30.6mmol)。然后加热至65℃，搅拌4小时。冷却至室温后，滤取生成的紫褐色结晶后，将滤取的结晶用乙醇500ml进行两次再淤浆化洗涤。对其进行减压干燥，得到紫褐色粉末80.0g(280.5mmol、收率96.3％)。
接着，在1000ml三口烧瓶中，加入上述紫褐色粉末72.0g(261.5mmol)，在其中加入乙酸720g、三氟乙酸72.0g，进行搅拌。然后加热至100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用乙酸200ml进行漂洗洗涤后，用己烷200ml进行漂洗洗涤。对其进行减压干燥，得到白色粉末30.0g(117.1mmol、收率44.8％)。
接着，在进行脱气氮气置换了的1000ml三口烧瓶中，加入上述得到的白色粉末26.0g(101.4mmol)、碘代苯122.7g(601.4mmol)、碘化铜54.7g(287.2mmol)、碳酸钾66.7g(482.6mmol)，在其中加入喹啉800ml，进行搅拌。然后加热至190℃，搅拌72小时。暂时冷却至室温后，加入水500ml、二氯甲烷500ml，进行搅拌后，滤取生成的黄色结晶。将滤液转移到2000ml分液漏斗，分馏为有机层和水层。将有机层用500ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到白色固体13.7g(41.2mmol、收率40.6％)。
接着，在进行脱气氮气置换了的500ml三口烧瓶中，加入55％氢化钠2.16g(49.5mmol)、脱水N，N’-二甲基甲酰胺70ml，在氮气流中进行搅拌。在上述得到的白色粉末13.7g(41.2mmol)中加入脱水N，N’-二甲基甲酰胺70ml，使其溶解，然后用15分钟滴加在同一烧瓶内。滴加结束后，继续搅拌1小时。然后，在氰尿酰氯3.76g(20.4mmol)中加入脱水N，N’-二甲基甲酰胺70ml，使其溶解，然后用15分钟滴加在同一烧瓶内。滴加结束后，继续搅拌2小时，然后，加入水350g，滤取析出的结晶。将滤取的结晶用水300g进行两次再淤浆化，然后用甲醇300g进行再淤浆化。对其进行减压干燥后，用柱色谱法进行提纯，得到白色粉末10.9g(14.0mmol、收率70.0％)。
接着，在300ml三口烧瓶中，加入上述得到的白色粉末10.0g(12.9mmol)、苯基硼酸2.0g(16.4mmol)、四(三苯基膦)钯(0)1.5g(1.3mmol)、乙醇50ml、甲苯100ml，进行搅拌。然后，使碳酸钠6.5g(47.0mmol)溶解于水50ml，加在同一烧瓶内，加热至85℃，搅拌5小时。暂时冷却至室温后，加入水100ml、甲苯100ml，进行搅拌后，暂时过滤分离不溶物。将滤液转移到1000ml分液漏斗，分馏为有机层和水层。将有机层用100ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到黄色固体5.3g(6.5mmol、收率50.2％)。
化合物40的EI-MS(M+1)为818、熔点未测出。
实施例3
(化合物27的合成)
在进行脱气氮气置换了的2000ml三口烧瓶中，加入1，2-环己二酮33.3g(297.0mmol)、苯肼盐酸盐86.0g(594.7mmol)，在其中加入乙醇1000ml，进行搅拌。然后，用5分钟在同一烧瓶内滴加浓硫酸3.0g(30.6mmol)。然后加热至65℃，搅拌4小时。冷却至室温后，滤取生成的紫褐色结晶后，将滤取的结晶用乙醇500ml进行两次再淤浆化洗涤。对其进行减压干燥，得到紫褐色粉末80.0g(280.5mmol、收率96.3％)。
接着，在1000ml三口烧瓶中，加入上述紫褐色粉末72.0g(261.5mmol)，在其中加入乙酸720g、三氟乙酸72.0g，进行搅拌。然后加热至100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用乙酸200ml进行漂洗洗涤后，用己烷200ml进行漂洗洗涤。对其进行减压干燥，得到白色粉末30.0g(117.1mmol、收率44.8％)。
接着，在进行脱气氮气置换了的1000ml三口烧瓶中，加入上述得到的白色粉末26.0g(101.4mmol)、碘代苯122.7g(601.4mmol)、碘化铜54.7g(287.2mmol)、碳酸钾66.7g(482.6mmol)，在其中加入喹啉800ml，进行搅拌。然后加热至190℃，搅拌72小时。暂时冷却至室温后，加入水500ml、二氯甲烷500ml，进行搅拌后，滤取生成的黄色结晶。将滤液转移到2000ml分液漏斗，分馏为有机层和水层。将有机层用500ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到白色固体13.7g(41.2mmol、收率40.6％)。
接着，在进行脱气氮气置换了的2000ml三口烧瓶中，加入上述得到的白色粉末13.7g(41.2mmol)、6，6’-二溴-2，2’-联二吡啶6.4g(20.4mmol)、碘化铜1.14g(5.98mmol)、磷酸三钾25.22g(118.8mmol)，其中加入1，4-二烷200ml，进行搅拌。一边继续搅拌一边加入tranc-1，2-环己二胺10ml。然后，加热至115℃，搅拌15小时。暂时冷却至室温后，滤取不溶物。将滤液减压蒸馏除去后，加入甲醇，滤取析出的白色固体。然后，用柱色谱法进行提纯，得到白色固体5.0g(6.14mmol、收率30.0％)。
化合物27的EI-MS(M+1)为816、熔点为362℃。
实施例4
在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从蒸镀源蒸镀化合物9，以/秒形成50nm厚的薄膜。用荧光测定装置评价作成的薄膜。
接着，在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从不同的蒸镀源蒸镀化合物9和Ir(ppy)3，以/秒形成50nm厚的Ir(ppy)3的浓度为7.0％的薄膜。
用荧光测定装置评价作成的薄膜。激发波长使用化合物9的极大吸收波长，观察此时发出的光，与单独化合物9的薄膜的情况下发出的光进行比较。结果示于表1。
实施例5
在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从蒸镀源蒸镀化合物40，以/秒形成50nm厚的薄膜。用荧光测定装置评价作成的薄膜。
接着，在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从不同的蒸镀源蒸镀化合物40和Ir(ppy)3，以/秒形成50nm厚的Ir(ppy)3的浓度为7.0％的薄膜。
用荧光测定装置评价作成的薄膜。激发波长使用化合物40的极大吸收波长，观察此时发出的光，并与单独化合物40的薄膜的情况下发出的光进行比较。结果示于表1。
实施例6
在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从蒸镀源蒸镀化合物27，以/秒形成50nm厚的薄膜。用荧光测定装置评价作成的薄膜。
接着，在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从不同的蒸镀源蒸镀化合物27和Ir(ppy)3，以/秒形成50nm厚的Ir(ppy)3的浓度为7.0％的薄膜。
用荧光测定装置评价作成的薄膜。激发波长使用化合物27的最大吸收波长，观察此时发出的光，并与单独化合物27的薄膜的情况下发出的光进行比较。结果示于表1。
比较例1
除将薄膜主要成分变更为Alq3作成薄膜以外，和实施例4同样进行。结果示于表1。由表1可知，在发光层的主要材料使用化合物9、40及27时，Ir(ppy)3发生能量转换，可观察到来自Ir(ppy)3的发光，但使用Alq3时，Ir(ppy)3没有发生能量转换，Alq3自身发出荧光。
[表1]
实施例7
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。在形成有膜厚150nm的由I TO形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。
接着，在空穴输送层上，作为发光层，从不同的蒸镀源共蒸镀化合物9和Ir(ppy)3，形成25nm厚。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。进而，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。
实施例8
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。在形成有膜厚150nm的由ITO形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。
接着，在空穴输送层上，作为发光层从不同的蒸镀源共蒸镀化合物40和Ir(ppy)3，形成25nm厚。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。进而，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。
实施例9
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。在形成有膜厚150nm的由ITO形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。
接着，在空穴输送层上，作为发光层，从不同的蒸镀源共蒸镀化合物27和Ir(ppy)3，形成25nm厚。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。进而，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，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。予以说明的是，已知元件发光光谱的极大波长为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作为发光层的主成分以外，和实施例7同样进行地作成有机EL元件。
比较例3
除使用TAZ作为发光层的主成分以外，和实施例7同样地作成有机EL元件。
[表2]
实施例10
(化合物103的合成)
在进行脱气氮气置换了的200ml三口烧瓶中，加入1，2-环己二酮33.3g(0.297mol)、苯肼盐酸盐86.0g(0.595mol)，在其中加入乙醇1000ml，进行搅拌。然后，用5分钟在同一烧瓶内滴加浓硫酸3.0g(0.03mol)。然后加热至65℃，搅拌4小时。冷却至室温后，滤取生成的紫褐色结晶后，将滤取的结晶用乙醇500ml进行两次再淤浆化洗涤。对其进行减压干燥，得到紫褐色粉末80.0g(0.286mol、收率96.3％)。
接着，在上述紫褐色粉末72.0g(0.258mol)中加入乙酸720g、三氟乙酸72.0g，进行搅拌。然后加热至100℃，搅拌15小时。冷却至室温后，滤取生成的黄色结晶后，将滤取的结晶用乙酸200ml进行漂洗洗涤后，用己烷200ml进行漂洗洗涤。对其进行减压干燥，得到白色粉末30.0g(0.117mol、收率45.3％)。
接着，在进行脱气氮气置换了的1000ml三口烧瓶中，加入上述得到的白色粉末26.0g(0.101mol)、碘代苯122.7g(0.601mol)、碘化铜54.7g(0.287mol)、碳酸钾66.7g(0.482mol)，在其中加入喹啉800ml，进行搅拌。然后加热至190℃，搅拌72小时。暂时冷却至室温后，加入水500ml、二氯甲烷500ml，进行搅拌后，滤取生成的黄色结晶。将滤液转移到2000ml分液漏斗，分馏为有机层和水层。将有机层用500ml水洗涤三次后，将得到的有机层用硫酸镁进行脱水，暂时过滤分离硫酸镁后，将溶剂减压蒸馏除去。然后，用柱色谱法进行提纯，得到白色固体13.7g(0.04mol、收率40.8％)。
接着，在进行脱气氮气置换了的500ml三口烧瓶中，加入55％氢化钠2.16g(49.5mmol)、脱水N，N’-二甲基甲酰胺70ml，在氮气流中进行搅拌。在上述得到的白色粉末13.7g(40mmol)中加入脱水N，N’-二甲基甲酰胺70ml，使其溶解，然后用15分钟滴加在同一烧瓶内。滴加结束后，继续搅拌1小时。然后，在氰尿酰氯2.46g(13mmol)中加入脱水N，N’-二甲基甲酰胺70ml，使其溶解，然后用15分钟滴加在同一烧瓶内。滴加结束后，在内温为80℃下继续搅拌24小时后，冷却至室温。冷却后，在同一烧瓶内加入水350g，滤取析出的结晶。将滤取的结晶用水300g进行两次再淤浆化，然后用甲醇300g进行再淤浆化。对其进行减压干燥后，用柱色谱法进行提纯，得到淡黄色粉末2.1g(2.0mmol、收率15.5％)。
化合物103的EI-MS(M+1)为1072、熔点为492℃。
实施例11
在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从蒸镀源蒸镀化合物103，以/秒形成50nm厚的薄膜。用荧光测定装置评价作成的薄膜。接着，在玻璃基板上利用真空蒸镀法，在真空度4.0×10-4Pa下，从不同的蒸镀源蒸镀化合物3和Ir(ppy)3，以秒形成50nm厚的Ir(ppy)3的浓度为7.0％的薄膜。
用荧光测定装置评价作成的薄膜。激发波长使用化合物103的极大吸收波长，观察此时发出的光，并与单独化合物103的薄膜的情况下发出的光进行比较。结果示于表3。
比较例4
除将薄膜主成分变更为Alq3作成薄膜以外，和实施例11同样进行。结果示于表3。
[表3]
实施例12
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。在形成有膜厚150nm的由ITO形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。
接着，在空穴输送层上，作为发光层从不同的蒸镀源共蒸镀化合物103和Ir(ppy)3，形成25nm厚。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。进而，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4所示的发光特性。在表4中，亮度、电压及发光效率表示在10mA/cm2下的值。予以说明的是，已知元件发光光谱的极大波长为517nm，可得到来自Ir(ppy)3的发光。
比较例5
除使用HMTPD作为空穴输送层、使用TAZ作为发光层的主成分以外，和实施例12同样地作成有机EL元件。
比较例6
除使用TAZ作为发光层的主成分以外，和实施例12同样地作成有机EL元件。
[表4]
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。因此可以认为，本发明的有机EL元件应用于平板显示器(例如OA计算机用或壁挂式电视)、车载显示元件、利用了作为手提电话显示或面发光体的特征的光源(例如复印机的光源、液晶显示器、仪表类的背光光源)、显示板、指示灯，其技术价值大。

Claims (9)

1.有机电致发光元件用化合物，其由下述通式(2)表示，
式中，环A、环A’表示和相邻环缩合的式(2a)表示的芳香环，
环B、环B’表示和相邻环缩合的式(2b)表示的杂环，
Ar1为未取代的或碳数1-6的烷基、苯基或吡啶基取代的、取代基的数为0-4的以下Y-7、Y-26～Y-44的连接基团；
X表示碳，
R5表示氢、未取代的或碳数1-6的烷基、苯基、吡啶基取代的、取代基的数0-4的苯基、联苯基、或吡啶基，
R6表示未取代的或碳数1-6的烷基、苯基、吡啶基取代的、取代基的数0-4的苯基、联苯基、或吡啶基，
R1～R4独立地表示氢、未取代的或碳数1-6的烷基、苯基、或吡啶基取代的、取代基的数0-4的苯基、联苯基、或吡啶基，
2.权利要求1所述的有机电致发光元件用化合物，其由下述通式(4)表示，
式中，Ar3为与通式(2)中的Ar1的含义相同；
R17、R20与通式(2)中的R5的含义相同；
R22、R23与通式(2)中的R6的含义相同；
R16、R18、R19、R21表示氢、未取代的或碳数1-6的烷基、苯基、或吡啶基取代的、取代基的数0-4的苯基、联苯基、或吡啶基，
3.权利要求1所述的有机电致发光元件用化合物，其中通式(2)及式(2a)～(2b)中，环A、环A’为苯环，R6为未取代的或碳数1-6的烷基、苯基或吡啶基取代的、取代基的数为0-4的苯基或吡啶基，且R1-R4为氢或苯基。
4.权利要求2所述的有机电致发光元件用化合物，其中通式(4)中，R22～R23为未取代的、或碳数1-6的烷基、苯基或吡啶基取代的、取代基的数为0-4的苯基或吡啶基，且R16～R21为氢或苯基。
5.权利要求1所述的有机电致发光元件用化合物，其中通式(2)的Ar1为由以下的Y-7或Y-28表示连接基团，
6.如权利要求1所述的有机电致发光元件用化合物，其中，通式(2)表示的有机电致发光元件用化合物，选自以下的化合物：
7.一种有机电致发光元件，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电致发光元件，其中，该发光层含有磷光发光性掺杂剂和权利要求1～6中任一项所述的有机电致发光元件用化合物作为主体材料。
8.如权利要求7所述的有机电致发光元件，其在阳极和发光层之间具有空穴注入输送层以及在阴极和发光层之间具有电子注入输送层而成。
9.如权利要求8所述的有机电致发光元件，其在发光层和电子注入输送层之间具有空穴阻挡层而成。
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KR101082258B1 (ko) 2011-11-09
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