CN100483779C - 有机电致发光元件 - Google Patents
有机电致发光元件 Download PDFInfo
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- CN100483779C CN100483779C CNB2004800081874A CN200480008187A CN100483779C CN 100483779 C CN100483779 C CN 100483779C CN B2004800081874 A CNB2004800081874 A CN B2004800081874A CN 200480008187 A CN200480008187 A CN 200480008187A CN 100483779 C CN100483779 C CN 100483779C
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- organic electroluminescent
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- 239000010410 layer Substances 0.000 claims abstract description 214
- -1 azole compound Chemical class 0.000 claims abstract description 39
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims abstract description 9
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- 150000004696 coordination complex Chemical class 0.000 claims description 9
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Abstract
本发明涉及在基板上叠层阳极、有机层及阴极制的有机电致发光元件，其中至少1层的有机层是含主剂和掺杂剂的发光层，至少1层的有机层使用同一分子中兼具噁二唑结构和三唑结构的唑化合物。该唑化合物除了作为发光层的主剂使用外，还可以在空穴阻止层或电子传输层中使用。该有机EL元件适合用于全色或多色的板，成为发光效率比使用来自单态的发光的EL元件高、驱动稳定性得到改善的有机电致发光元件。
Description
技术领域
本发明涉及有机电致发光元件，详细地讲，涉及对有机化合物构成的发光层施加电场发出光的薄膜型器件。
技术背景
使用有机材料的电致发光元件(以下称有机EL元件)的开发，为了提高来自电极的电荷注入效率，通过电极种类的最佳化，开发在电极间设置芳香族二胺构成的空穴传输层和8-羟基喹啉合铝络合物构成的发光层形成薄膜的元件(Appl.Phys.Lett.，Vol.，51，pp913，1987)，其发光效率比以往使用蒽等的单晶的元件得到大幅度的改善，故向具有自发光、高速响应性特征的高性能平板显示器的实用化发展。
为了进一步提高这种有机EL元件的效率，众知以上述的阳极/空穴传输层/发光层/阴极的构成作为基本构成，再适当设置空穴注入层、电子注入层或电子传输层，例如阳极/空穴注入层/空穴传输层/发光层/阴极，或阳极/空穴注入层/发光层/电子传输层/阴极、阳极/空穴注入层/发光层/电子传输层/电子注入层/阴极等的构成的元件。该空穴传输层具有使由空穴注入层注入的空穴传输到发光层的功能，而电子输送层具有使由阴极注入的电子传输到发光层的功能。
迄今配合这类构成层的功能已开发了许多的有机材料。
另外，虽然以设有上述的芳香族二胺构成的空穴传输层与8-羟基喹啉的铝络合物构成的发光层的元件为代表的众多的元件利用荧光发光，但如果利用磷光发光，即如果利用三重激发状态产生的发光，则与以往使用荧光(单态)的元件相比，可期待提高3倍左右的效率。为此目的研究了以香豆酮衍生物或二苯甲酮衍生物为发光层，但只能得到极低的辉度。此后，作为利用三重态的尝试，研究了使用铕络合物，但这也没有达到高效率的发光。
Nature，Vol.395，p151，(1998)中报道了通过使用铂络合物(PtOEP)可高效率的红色发光。此后，Appl.Phys.Lett.，Vol.75，P4，(1999)报道了通过在发光层中掺杂铱络合物(Ir(Ppy)3)大幅度改善绿色发光效率。此外，又报道了这些的铱络合物通过使发光层最佳化，即使元件结构更单纯化也呈现极高的发光效率。
为了使有机EL元件应用于平板显示器等显示器件中，必须改善元件的发光效率，同时又充分确保驱动时的稳定性。然而，使用该文献中所述的磷光分子(Ir(Ppy)3)的高效率的有机EL元件目前在实用上驱动稳定性并不充分。
上述的驱动劣化的主要原因估计由于基板/阳极/空穴传输层/发光层/空穴阻止层/电子传输层/阴极、或基板/阳极/空穴传输层/发光层/电子传输层/阴极构成的元件结构中发光层的薄膜形状劣化所致。这种薄膜形状的劣化，估计由元件驱动时的放热等造成的有机非晶薄膜的结晶化(或凝聚)等引起，耐热性低是由于材料的玻璃化转变温度(Tg)低。
上述Appl.Phys.Lett.，中，发光层使用咔唑化合物(CBP)或三唑系化合物(TAZ)，而空穴阻止层使用菲绕啉衍生物(HB-1)，但由于这些化合物对称性好、分子量小，故容易结晶化·凝聚后薄膜形状发生劣化，而且由于结晶性高甚至难观测Tg。这种发光层内的薄膜形状不稳定造成元件的驱动寿命缩短，耐热性也降低之类的不良影响。由于如上所述的理由，实际状况是使用磷光的有机EL元件，元件的驱动稳定性还存在很大的问题。
然而，JP 2002-352957A公开了发光层中含有主剂和发磷光的掺杂剂的有机EL元件，作为主剂使用具有噁二唑基的化合物。JP2001-230079A公开了有机层中具有噻唑结构或吡唑结构的有机EL元件。JP 2001-313178A公开了具有含磷光性的铱络合化合物和咔唑化合物的发光层的有机EL元件。JP 2003-45611A公开了具有含咔唑化合物(PVK)、具有噁二唑基的化合物(PBD)及Ir(Ppy)3的发光层的有机EL元素。JP 2002-158091A提出了正金属化金属及卟啉金属络合物作为磷光性发光性化合物的方案。但这些也有如上所述的问题。JP 2001-230079A没有公开利用磷光的有机EL元件。
发明内容
在考虑平板显示器等显示器件或照明等的应用上，必须要求改善使用磷光的有机EL元件的驱动稳定性及耐热性，本发明鉴于这样的实际状况，其目的在于提供具有高效率且高驱动稳定性的有机EL元件。
本发明者们潜心进行研究的结果，发现通过在发光层或电子传输层或空穴阻止层使用特定的化合物可以解决上述课题，从而完成了本发明。
即，本发明涉及阳极、有机层和阴极叠层在基板上的有机电致发光元件，由使同一分子中兼具下述式I表示的噁二唑结构和下述式II表示的三唑结构的唑系化合物存在于至少1层的有机层中的结构构成。
(式中，Ar1～Ar3各自独立地表示可以具有取代基的芳香族烃环基或芳香族杂环基，但当式I的结构是2价的基团时，Ar1是单键，当式II的结构是2价或3价的基团时，Ar2和Ar3的任何一个或两者是单键)。
这里，唑系化合物优选列举下述通式IV～VIII的任何一个表示的化合物。
(式中，Ar1～Ar3各自独立地表示可以具有取代基的芳香族烃环基或芳香族杂环基，X1表示2价的芳香族烃环基)。
另外，本发明涉及至少1层的有机层是含主剂和掺杂剂的发光层，作为该主剂使用前述的唑系化合物为特征的有机电致发光元件。
作为掺杂剂，优选举出含有选自磷光发光性的正金属化金属络合物及卟啉金属络合物的至少一种的掺杂剂。另外，作为金属络合物的中心金属，优选含有含选自周期表7～11族的至少一种金属的有机金属络合物的中心金属。
另外，本发明涉及使前述唑系化合物存在于空穴阻止层或电子传输层中为特征的有机EL元件。
本发明的有机电致发光元件(有机EL元件)具有基板上配置在阳极与阴极之间的至少1层的有机层，该有机层的至少1层含有特定的唑系化合物。作为含有该唑系化合物的层，优选列举发光层、空穴阻止层或电子传输层。
存在于发光层中的场合，使该唑系化合物作为主剂存在，含发磷光的掺杂剂。而且通常含主剂作为主成分，含掺杂剂作为副成分。这里，所谓主成分意味着形成该层的材料中占50重量％以上的成分，所谓副成分是指该成分以外的成分。作为主剂的化合物，具有比磷光性的掺杂剂的激发三重态能级高的能级状态的激发三重态能级。以下，对该唑系化合物作为主剂存在的场合进行说明。
作为本发明中发光层使用的主剂，必须是赋予稳定的薄膜形状，具有高玻璃化转变温度(Tg)，可高效地传输空穴和/或电子的化合物。还要求是电化学上且化学上稳定，制造时或使用时难产生成为阱或消除发光的杂质的化合物。作为满足这种要求的化合物，使用兼具前述通式I和II表示的1，3，4-噁二唑结构和1，2，4-三唑结构的化合物(以下称唑系化合物)。
通式I和II中，Ar1～Ar3具有上述的意思，但作为优选的基团可列举下述表示的基团。再者，Ar1、Ar2及Ar3既可以彼此相同也可以不同。
作为Ar1可优选举出1～3环的芳香族烃环基，可以具有取代基。作为取代基优选举出C1～C5的低级烷基。取代基的数优选0～3的范围。具体地，优选举出如下的芳香族烃环基。苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2，4-二甲基苯基，3，4-二甲基苯基、4-乙基苯基、2，4，5-三甲基苯基、4-叔丁基苯基、1-萘基、9-蒽基、9-菲基等。
作为Ar2可优选举出1～3环的芳香族烃环基，可以具有取代基。作为取代基优选举出C1～C5的低级烷基。取代基的数优选0～3的范围。具体地，优选列举如下的芳香族烃环基。苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2，4-二甲基苯基、3，4-二甲基苯基、2，3-二甲基苯基、2，5-二甲基苯基、2，6-二甲基苯基、3，5-二甲基苯基、4-乙基苯基、2-仲丁基苯基、2-叔丁基苯基、4-正丁基苯基、4-仲丁基苯基、4-叔丁基苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-菲基等。
作为Ar3可优选举出1～3环的芳香族烃环基，可以具有取代基。作为取代基优选举出C1～C5的低级烷基。取代基的数优选0～3的范围。具体地，优选列举如下的芳香族烃环基。苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-乙基苯基、4-乙基苯基、2，3-二甲基苯基、2，4-二甲基苯基、2，5-二甲基苯基、2，6-二甲基苯基、3，4-二甲基苯基、3，5-二甲基苯基、2，4，5-三甲基苯基、2，4，6-三甲基苯基、4-正丙基苯基、4-仲丁基苯基、4-叔丁基苯基、1-萘基、2-萘基、9-蒽基等。
本发明使用的唑系化合物是兼具1，3，4-噁二唑结构和1，2，4-三唑结构的化合物，各结构可以具有1个以上，也可以具有多个，但各结构是1～2的范围，优选合计2～4的范围。
在1，3，4-噁二唑结构与1，2，4-三唑结构合计具有3个以上的场合，该一个以上位于中间时的1，3，4-噁二唑结构或1，2，4-三唑结构为2价或3价的基团。该场合Ar1～Ar3与其价数相对应为单键，即不存在。式I表示的1，3，4-噁二唑结构为2价的基团的场合，Ar1为单键。式II表示的1，2，4-三唑结构为2价的基团的场合，Ar2～Ar3的任何一个为单键，为3价的基团的场合，两者为单键。一般，式I及式II表示的结构中，优选具有2～3个为1价基团的结构。
作为优选的唑系化合物，可列举前述通式IV～VIII表示的化合物。通式IV～VIII中，Ar1～Ar3是与通式I及II中说明的同样的基团，但不是单键，另外，X1是2价的连接基，由2价的芳香族烃环基构成。作为2价的连接基，优选1～2环的芳香族烃环基。具体地，优选列举如下的2价的芳香族烃环基。1，4-亚苯基、1，3-亚苯基、1，4-亚萘基、2，6-亚萘基、4，4′-亚联苯基等。
本发明使用的唑系化合物，其特征在于具有噁二唑结构和三唑结构的两种结构。迄今的见识认为噁二唑结构或三唑结构单独存在的化合物(例如PBD或TAZ)由于结晶性高，故缺乏薄膜稳定性，作为有机EL元件材料缺乏实用性。这种高结晶性的原因估计是因为噁二唑基或三唑基这种极性较高的官能基的存在造成强的分子间相互作用的缘故。由这样的考察推测使用同一分子内共存异种的高极性官能团，通过赋予极性相互抵消的作用而抑制分子间相互作用，结果出现薄膜稳定性提高。
把通式IV所示化合物的优选具体例示于表1～4，把通式V所示化合物的优选具体例示于表5～7，把通式VI所示化合物的优选具体例示于表8～10，把通式VII所示化合物的优选具体例示于表11～12，把通式VIII所示化合物的优选具体例示于表13～14，但不限定于这些。此外，表中的Ar1、X1、Ar2及Ar3与通式IV～VIII的Ar1、X1、Ar2及Ar3相对应。
通式IV表示的化合物的例子。
(表1)
(表2)
(表3)
(表4)
通式V表示的化合物的例子。
(表5)
(表6)
(表7)
通式VI表示的化合物的例子。
(表8)
(表9)
(表10)
通式VII表示的化合物的例子。
(表11)
(表12)
通式VIII表示的化合物的例子。
(表13)
(表14)
本发明的有机EL元件在发光层中含有上述主剂材料的场合，发光层中含有副成分，即磷光性掺杂剂。作为这种掺杂剂，可以使用前述文献所述的公知的磷光性金属络合化合物，这些的金属络合物的中心金属优选是含选自周期表7～11族的金属的磷光性有机金属络合物。作为这种金属优选举出选自钌、铑、钯、银、铼、锇、铱、铂及金的金属。该掺杂剂及金属可以是1种也可以是2种以上。
磷光性掺杂剂如JP2002-352957A等所述是公知物。另外，磷光性掺杂剂优选是磷光发光性的正金属化金属络合物或卟啉金属络合物，这样的正金属化金属络合物或卟啉金属络合物，如JP2002-158091A等所述是公知物。因此，可以广泛地使用这些公知的磷光性掺杂剂。
作为优选的有机金属络合物，包括作为中心金属具有Ir等贵金属元素的Ir(Ppy)3等的络合物类(式A)、Ir(bt)2·acac3等的络合物类(式B)，PtOEt3等的络合物类(式C)。
以下列出这些络合物类的具体例，但不限于下述的化合物。
(式A)
(式B)
(式C)
这种唑系化合物也可以存在于发光层以外，该场合下存在于发光层中的化合物可以是公知的发光材料，也可以不含掺杂剂。存在于发光层以外的场合下，优选存在于空穴阻止层或电子传输层中，但也可以根据层构成存在于其他的层中，或与其他的化合物一起存在于多个层中。
附图说明
图1表示呈现有机EL元件的层结构的模式图。是在基板1上层叠阳极2、空穴注入层3、空穴传输层4、发光层5、空穴阻止层6、电子传输层7及阴极8的例。
具体实施方式
以下，对本发明的有机EL元件的一个例子边参照附图边进行说明。图1是模式地表示本发明使用的一般的有机EL元件结构例的截面图，图中符号分别表示1-基板、2-阳极、3-空穴注入层、4-空穴传输层、5-发光层、6-空穴阻止层、7-电子传输层、8-阴极。通常，空穴注入层3～电子传输层7是有机层，本发明的有机EL元件有一层以上的含发光层5的有机层。优选具有含发光层5有三层以上，更优选有五层以上的有机层。另外，图1是1个例子，除此之外可以有一个以上的其他层，也可以省去一个以上的层。
基板1是作为有机EL元件支撑体的板，可以使用石英或玻璃板、金属板或金属箔、塑料薄膜或片材等。特别优选玻璃板、聚酯、聚甲基丙烯酸酯、聚碳酸酯、聚砜等的透明合成树脂板。使用合成树脂基板的场合要注意气体阻隔性。基板的气体阻隔性太小时，有时有机EL元件会被透过基板的外界气体老化而不好。因此，在合成树脂基板的至少一面设置致密的硅氧化膜等确保气体阻隔性的方法是优选的方法之一。
基板1上设置阳极2，阳极2起空穴注入到空穴传输层的作用。该阳极通常由铝、金、银、镍、钯、铂等金属，铟和/或锡的氧化物等金属氧化物、碘化铜等卤化金属、炭黑或聚(3-甲基噻吩)、聚吡咯、聚苯胺等导电性高分子等构成。通常，阳极2的形成大多采用溅射法、真空蒸镀法等进行。另外，银等的金属微粒、碘化铜等的微粒、炭黑、导电性的金属氧化物微粒、导电性高分子微粉末等的场合，也可以分散在适当的粘合树脂溶液中，涂布在基板1上形成阳极2。此外，导电性高分子的场合，还可以通过电解聚合直接在基板1上形成薄膜，或在基板1上涂布导电性高分子形成阳极2。阳极2也可使用不同的物质叠层形成。阳极2的厚度依所需的透明性而不同。需要透明性的场合，通常使可见光的透过率为60％以上，优选80％以上。此时厚度通常为5～1000nm，优选是10～500nm左右。不透明的场合，阳极2可以与基板1相同。另外，还可以在上述的阳极2的上面叠层不同的导电材料。
为了提高空穴注入效率，并且改善有机层整体对阳极的附着力，也可以在空穴传输层4与阳极2之间插入空穴注入层3。通过插入空穴注入层3，具有降低初期元件的驱动电压，同时也抑制恒电流下连续驱动元件时的电压升高的效果。
作为用于空穴注入层的材料所要求的条件，要求可以与阳极充分接触形成均匀的薄膜，热稳定，即熔点与玻璃化转变温度高，要求熔点300℃以上，玻璃化转变温度100℃以上。此外，可列举离子化电势低、来自阳极的空穴注入容易，空穴迁移率大。
为了此目的，迄今报道了铜酞菁等的酞菁化合物、聚苯胺、聚噻吩等的有机化合物，溅射碳膜，钯氧化物、钌氧化物、钼氧化物等的金属氧化物。阳极缓冲层的场合，可与空穴传输层同样地形成薄膜，但无机物的场合，还可以采用溅射法或电子束蒸镀法，等离子CVD法。如上所述形成的空穴注入层3的膜厚通常是3～100nm，优选是5～50nm。
在空穴注入层3的上面设置空穴传输层4。作为空穴传输层使用的材料所要求的条件，必须是来自空穴注入层3的空穴注入效率高，而且可以高效率地传输所注入空穴的材料。因此，要求离子化电势小，对可见光透明性高，而且空穴迁移率大，稳定性又好，在制造时或使用时难产生作为阱的杂质。并且，为了与发光层5相接，要求消除来自发光层的发光，或在与发光层之间形成受激态络合物而不降低效率。除了上述的一般要求外，考虑车载显示用的应用时，元件还要求耐热性。因此，期望具有Tg为90℃以上值的材料。
作为这样的空穴传输材料，例如，可列举4，4′-二[N-(1-萘基)-N-苯基氨基]联苯所代表的含2个以上叔胺，2个以上的缩合芳香族环取代于氮原子上的芳香族二胺、4，4′，4″-三(1-萘基苯基氨基)三苯胺等具有繁星式结构的芳香族胺化合物、三苯胺的四聚体构成的芳香族胺化合物、2，2′，7，7′-四(二苯基氨基)-9，9′-螺二芴等的螺化合物等。这些化合物可以单独使用，也可以混合使用。
除了上述的化合物以外，作为空穴传输层4的材料，可列举聚乙烯基咔唑、聚乙烯基三苯胺、含有四苯基联苯胺的聚芳醚砜等高分子材料。涂布法的场合，添加1种以上的空穴传输材料和根据需要不变成空穴的阱的粘合树脂或涂布性改性剂等添加剂，溶解制备涂布溶液，采用旋转涂布法等方法涂布在阳极2或空穴注入层3上，干燥形成空穴传输层4。作为粘合树脂可列举聚碳酸酯、聚芳酯、聚酯等。粘合树脂添加量多时由于使空穴迁移率降低，故最好添加量少，通常优选50重量％以下。
真空蒸镀法的场合，把空穴传输材料加到设置在真空容器内的坩埚中，使用适当的真空泵将真空容器内排气到10-4Pa左右后，将坩埚加热使空穴传输材料蒸发，与坩埚相对置在形成有阳极的基板1上形成空穴传输层4。空穴传输层4的膜厚通常是5～300nm，优选是10～100nm。为了一样地形成这样薄的膜，一般优选采用真空蒸镀法。
在空穴传输层4的上面设置发光层5。发光层5含有前述主剂和发磷光的掺杂剂，在施加电场的电极间，通过从阳极注入并经空穴传输层移动的空穴和从阴极注入并经电子传输层7(或空穴阻止层6)移动的电子的再结合进行激发呈现强的发光。
使发光层存在唑系化合物作为主材料的场合，作为发光层主剂使用的材料所要求的条件，必须来自空穴传输层4的空穴注入效率高，且来自电子传输层7(或空穴阻止层6)的电子注入效率高。因此，要求离子化电势显示适度的值，而且空穴、电子的迁移率大，电稳定性又好，制造或使用时难产生成为阱的杂质。另外还要求在邻接的空穴传输层4、电子传输层7(或空穴阻止层6)之间形成受激态络合物而不降低效率。除了上述的一般要求以外，在考虑车载显示用的应用的场合，还要求元件耐热性。因此期望具有Tg为90℃以上值的材料。此外，发光层在不破坏本发明的性能的范围内也可以含有唑系化合物以外的其他的主材料或荧光色素等其他成分。
另外，不使发光层存在唑系化合物作为主体材料的本发明的另外的方案，发光层除了可以使用公知的主体材料及掺杂材料等的任意的化合物外，也可以使用不取决于主体材料与客体材料组合的单独的发光材料。在这种情况下，唑系化合物存在于空穴阻止层或电子传输层中。
作为掺杂剂使用前述式A～C表示的有机金属络合物的场合，该有机金属络合物在发光层中的含量优选在0.1～30重量％的范围。0.1重量％以下时无助于元件的发光效率提高，超过30重量％时，引起有机金属络合物彼此形成二聚物等的浓度消光，导致发光效率降低。在以往使用荧光(单重态)的元件中，存在优选比发光层中含有的荧光性色素(掺杂物)的量多若干的倾向。有机金属络合物朝膜厚方向部分地含在发光层中，也可不均匀地分布。发光层5的膜厚通常是10～200nm，优选是20～100nm。采用与空穴传输层4同样的方法形成薄膜。
发光层5最好是采用真空蒸镀法形成。把主剂、掺杂剂两者加到设置在真空容器内的坩埚中，使用适当的真空泵把真空容器内排气到10-4Pa左右后，加热坩埚，使主剂、掺杂剂两者同时蒸发，在空穴传输层4的上面形成发光层5。此时，边对主剂、掺杂剂分别监视蒸镀速度，边控制掺杂剂进入主剂的含量。
空穴阻止层6叠层在发光层5的上面使之与发光层5的阴极侧的界面相接，但由阻止空穴传输层移动过来的空穴到达阴极的作用，和可高效率地将由阴极注入的电子向发光层方向传输的化合物形成。作为构成空穴阻止层的材料所要求的物性，必须是电子迁移率高且空穴迁移率低。空穴阻止层6把空穴和电子封闭在发光层内，具有提高发光效率的作用。
电子传输层7由在施加了电场的电极间可以高效率地将由阴极注入的电子向空穴阻止层6的方向传输的化合物形成。作为电子传输层7使用的电子传输性化合物，必须是来自阴极8的电子注入效率高，且具有高的电子迁移率并可以高效率地传输所注入电子的化合物。
作为满足这样条件的材料，可列举8-羟基喹啉的铝络合物等金属络合物、10-羟基苯并[h]喹啉的金属络合物、噁二唑衍生物、二苯乙烯基联苯衍生物、硅烷醇衍生物、3-或5-羟基黄酮金属络合物、苯并噁唑金属络合物、苯并噻唑金属络合物、三苯并咪唑基苯、喹喔啉化合物、菲绕啉衍生物、2-叔丁基-9，10-N，N′-二氨基蒽醌二亚胺、n型氢化非晶碳化硅、n型硫化锌、n型硒化锌等。电子传输层7的膜厚通常是5～200nm，优选是10～100nm。
电子传输层7与空穴传输层4同样地采用涂布法或真空蒸镀法叠层在空穴阻止层6上而形成。通常使用真空蒸镀法。
阴极8起向发光层5注入电子的作用。作为阴极8使用的材料，可以使用前述阳极2所使用的材料，但为了高效率地进行电子注入，优选功函数低的金属，可以使用锡、镁、铟、钙、铝、银等适当的金属或这些金属的合金。作为具体例，可列举镁-银合金、镁-铟合金、铝-锂合金等低功函数合金电极。此外，在阴极与电子传输层的界面上插入LiF、MgF2、Li2O等的极薄绝缘膜(0.1～5nm)，这也是提高元件效率的有效方法。阴极8的膜厚通常与阳极2一样。为了保护低功函数金属构成的阴极，在阴极上面再叠层功函数高且对大气稳定的金属层从而增加元件的稳定性。为了此目的使用铝、银、铜、镍、铬、金、铂等金属。
此外，也可以是与图1相反的结构，例如，在基板1上按照阴极8、空穴阻止层6、发光层5、空穴传输层4、阳极2的顺序，或基板1/阴极8/电子传输层7/空穴阻止层6/发光层5/空穴传输层4/空穴注入层3/阳极2的顺序叠层。
实施例
合成例1
3-[4-(苯基-1，3，4-噁二唑基-(5))-苯基]-4，5-二苯基-1，2，4-三唑(以下称POT)的合成。
反应式如下所示。
对由化合物(6)和(8)合成POT的反应进行描述。
在1000ml的四口烧瓶中加入化合物(6)43.6g(0.150mol)和化合物(8)64.8g(0.300mol)及吡啶493.1g，升温到114℃，进行2小时加热·回流。反应后，把反应混合物投到3000ml的甲醇中，过滤析出的结晶，用1500ml甲醇洗涤结晶，100℃减压下进行干燥，制得干燥结晶51.3g。用二甲基甲酰胺将干燥结晶进行3次再结晶，制得POT的精制结晶31.0g。纯度99.97％(HPLC面积比)、质量分析值441、熔点273.0℃、收率46.8％。POT是表1的NO1的化合物。
把POT的IR分析结果示于下述。
IR(KBr)3432，3060，1614，1578，1548，1496，1470，1450，1424，1400，1270，1070，1018，972，966，848，776，740，716，694，620，608，536，492
合成例2
3，4-二[4-(2-苯基-1，3，4-噁二唑基-(5))-苯基]-5-苯基-1，2，4-三唑(以下称3，4-BPOT)的合成
反应式示于下述。
对由化合物(14)与(10)合成3，4-BPOT的反应进行描述。
在200ml的四口烧瓶中加入化合物(14)6.1g(0.011mol)和化合物(10)4.9g(0.034mol)及吡啶73.3g，升温到117℃，进行2小时加热·回流。反应后，添加10.9g的甲醇，过滤析出的结晶，结晶使用二氯甲烷进行再结晶，制得3，4-BPOT的精制结晶3.6g。纯度99.16％(HPLC面积比)，质量分析值585，熔点324.0℃，收率55.9％。此外，3，4-BPOT是表8的No55的化合物。
把3，4-BPOT的IR分析结果示于下述。
IR(KBr)3448，3060，2920，2856，1932，1612，1582，1550，1502，1488，1470，1448，1424，1316，1270，1190，1160，1100，1064，1016，990，962，924，868，850，776，746，734，712，690，638，608，532，506，488
合成例3
3，5-二[4-(2-苯基-1，3，4-噁二唑基-(5))-苯基]-5-苯基-1，2，4-三唑(以下称3，5-BPOT)的合成
把反应式示于下述。
对由化合物(19)与(10)合成3，5-BPOT的反应进行描述。
在300ml的四口烧瓶中加入化合物(19)5.6g(0.011mol)和化合物(10)4.2g(0.030mol)及吡啶87.9g，升温到117℃，进行2小时加热·回流。反应后，添加136.5g的甲醇，过滤析出的结晶，结晶用二氯甲烷进行再结晶，制得3，5-BPOT的精制结晶3.3g。纯度99.31％(HPLC面积比)，质量分析值585，熔点344.1℃，收率51.3％。此外，3，5-BPOT是表5的NO37的化合物。
把3，5-BPOT的IR分析结果示于下述。
IR(KBr)3452，3060，2924，1612，1548，1472，1450，1412，1314，1270，1174，1152，1104，1066，1026，1016，964，924，850，780，744，714，690，640，612，534，500
实施例1
如下所述制造图1中具有省去空穴注入层3和空穴阻止层6的层结构的有机EL元件。
使用电阻加热方式的真空蒸镀装置，在电极面积2×2mm2的洗涤的带ITO电极的玻璃基板上(三洋真空制)，利用アルバツク公司制的水晶振动子型膜厚控制器边控制蒸镀速度，边在蒸镀中的真空度7～9×10-4Pa的条件下，在上述带ITO的玻璃基板1的ITO层(阳极2)的上面形成4，4′-二[N，N′-(3-甲苯基)氨基]-3，3′-二甲基联苯(以下为HMTPD)60nm厚的膜，形成空穴传输层4。不破坏真空度而在同一真空蒸镀装置内，由不同的蒸镀源采用二元同时蒸镀法，在空穴传输层4上形成作为发光层主要成分的POT和作为磷光性有机金属络合物的三(2-苯基吡啶)铱络合物(以下称Ir(Ppy)3)的25nm的膜厚，形成发光层5。此时，Ir(Ppy)3的浓度是7wt％。不破坏真空度而在同一真空蒸镀装置内，在发光层5上形成三(8-羟基喹啉)铝(以下称Alq3)的50nm的膜厚，得到电子传输层7。仍维持真空条件再在电子传输层7上蒸镀氟化锂(以下称LiF)0.5nm、铝170nm的膜厚，形成阴极8。
将外部电源与制得的有机EL元件相连并施加直流电压，结果确认这些有机EL元件具有如表15的发光特性。此外，元件发光光谱的极大波长是512nm，确认得到Ir(Ppy)3发出的光。
实施例2
作为发光层5的主要成分，除了使用3，4-BPOT以外，其他与实施例1同样地制造有机EL元件。把该元件特性示于表15。
实施例3
作为发光层5的主要成分，除了使用3，5-BPOT以外，其他与实施例1同样地制造有机EL元件。由该有机EL元件也确认得到Ir(Ppy)3发出的光。
比较例1
作为发光层5的主要成分，除了使用3-苯基-4-(1′-萘基)-5-苯基-1，2，4-三唑(以下称TAZ)以外，其他与实施例1同样地制造有机EL元件。
实施例4
如下所述制造图1中具有省去空穴注入层3的层结构的有机EL元件。
与实施例1同样地，设置ITO层(阳极2)，在ITO层上形成N，N′-二萘基-N，N′-二苯基4，4′-二氨基联苯(以下称NPD)40nm的膜厚，形成空穴传输层4。不破坏真空而在同一真空蒸镀装置内，由不同的蒸镀源采用二元同时蒸镀法，在空穴传输层4上形成作为发光层主要成分的4，4′-N，N′-二咔唑联苯(以下称CBP)、作为磷光性有机金属络合物的Ir(Ppy)3 20nm的膜厚，形成发光层5。此时，Ir(Ppy)3的浓度是6wt％。不破坏真空而在同一真空蒸镀装置内在发光层5上形成6nm的POT膜厚，制得空穴阻止层6。仍维持真空条件在空穴阻止层6上形成20nm的Alq3膜厚，制得电子传输层7。此外，仍维持真空条件再在电子传输层7上蒸镀0.6nm的LiF、150nm的铝，形成阴极8。
对制得的有机EL元件连接外部电源并施加直流电压，结果确认这些有机EL元件具有如表15的发光特性。此外，元件发光光谱的极大波长是512nm，确认获得Ir(Ppy)3发出的光。
实施例5
作为空穴阻止层6，除了使用3，4-BPOT以外，其他与实施例4同样地制造有机EL元件。
实施例6
作为空穴阻止层6，除了使用3，5-BPOT以外，其他与实施例4同样地制造有机EL元件。
比较例2
作为空穴阻止层6，除了使用2，9-二甲基-4，7-二苯基-1，10-菲绕啉(以下称BCP)以外，其他与实施例4同样地制造有机EL元件。
把元件特性归纳示于表15。
(表15)
| 发光开始电压(V) | 最大亮度功率(cd/A) | 最大视感功率(1m/W) | |
| 实施例1 | 3.5 | 39.7 | 14.72 |
| 实施例2 | 3.5 | 30.3 | 13.58 |
| 比较例1 | 4.0 | 27.0 | 11.07 |
| 实施例4 | 3.5 | 35.4 | 18.72 |
| 实施例5 | 3.5 | 33.8 | 17.11 |
| 实施例6 | 3.0 | 4.1 | 19.32 |
| 比较例2 | 4.0 | 31.7 | 16.61 |
参考例
对作为发光层主要成分(主体材料)候补的化合物的耐热特性，采用DSC测定进行玻璃化转变温度(Tg)的测定。此外，TAZ、CBP、BCP及OXD-7是已知的主体材料，OXD-7是1，3-二[(4-叔丁基苯基)-1，3，4-噁二唑]亚苯基的简称。把测定结果示于表16。
(表16)
| 主体 | 玻璃化转变温度(Tg)(℃) |
| POT | 102 |
| 3，4-BPOT | 122 |
| 3，5-BPOT | 115 |
| TAZ | —<sup>1)</sup> |
| CBP | —<sup>1)</sup> |
| BCP | —<sup>1)</sup> |
| OXD-7 | —<sup>1)</sup> |
1)因结晶性高而不能观测
本发明的有机EL元件可适用于单一的元件、配置成阵列状的结构构成的元件、阳极与阴极配置成X-Y矩阵状的结构的任何一种。本发明的有机BL元件通过使发光层含有具有特定骨架的化合物和磷光性的金属络合物，可获得发光效率比使用以往来自单重态发光的元件高，而且驱动稳定性得到大幅度改善的元件，在用于全色或多色的平板显示器的应用中可发挥优异的性能。
Claims (8)
1.有机电致发光元件，是在基板上叠层阳极、有机层及阴极制的有机电致发光元件，其特征在于使至少1层的有机层中存在同一分子中兼具下述式I表示的噁二唑结构和下述式II表示的三唑结构的唑系化合物，
式中，Ar1～Ar3各自独立地表示可以具有取代基的芳香族烃环基或芳香族杂环基，但式I的结构是2价的基团的场合，Ar1是单键，式II的结构是2价或3价的基团的场合，Ar2及Ar3的任何一个或两者是单键。
2.权利要求1所述的有机电致发光元件，其中，唑系化合物是下述通式IV～VIII的任何一个表示的化合物，
式中，Ar1～Ar3各自独立地表示可以具有取代基的芳香族烃环基或芳香族杂环基，X1表示2价的芳香族烃环基。
3.权利要求1或2所述的有机电致发光元件，其特征在于，所述的至少1层的有机层是含主剂和掺杂剂的发光层，作为该主剂使用同一分子中兼具式I表示的噁二唑结构和式II表示的三唑结构的唑系化合物。
4.权利要求3所述的有机电致发光元件，其中，掺杂剂是含有选自磷光发光性的正金属化金属络合物及卟啉金属络合物的至少一种的掺杂剂。
5.权利要求4所述的有机电致发光元件，其中，金属络合物的中心金属是选自钌、铑、钯、银、铼、锇、铱、铂及金的至少一种的金属。
6.权利要求1所述的有机电致发光元件，其特征在于，所述有机电致发光元件具有发光层，在发光层与阴极之间有空穴阻止层。
7.权利要求1所述的有机电致发光元件，其特征在于，所述有机电致发光元件具有发光层，在发光层与阴极之间有电子传输层。
8.权利要求1或2所述的有机电致发光元件，其中，存在唑系化合物的层是空穴阻止层或电子传输层。
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| JP2002352957A (ja) * | 2001-05-23 | 2002-12-06 | Honda Motor Co Ltd | 有機エレクトロルミネッセンス素子 |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR101032355B1 (ko) | 2011-05-03 |
| TW200504174A (en) | 2005-02-01 |
| JP4673744B2 (ja) | 2011-04-20 |
| KR20060016099A (ko) | 2006-02-21 |
| WO2004107822A1 (ja) | 2004-12-09 |
| JPWO2004107822A1 (ja) | 2006-07-20 |
| TWI341860B (zh) | 2011-05-11 |
| US20060186791A1 (en) | 2006-08-24 |
| CN1765158A (zh) | 2006-04-26 |
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