CN101547877B - 苯并[a]荧蒽化合物和使用其的有机发光器件 - Google Patents

苯并[a]荧蒽化合物和使用其的有机发光器件 Download PDF

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CN101547877B
CN101547877B CN2008800009846A CN200880000984A CN101547877B CN 101547877 B CN101547877 B CN 101547877B CN 2008800009846 A CN2008800009846 A CN 2008800009846A CN 200880000984 A CN200880000984 A CN 200880000984A CN 101547877 B CN101547877 B CN 101547877B
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benzo
layer
fluoranthene
fluoranthene compound
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CN101547877A (zh
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山田直树
井川悟史
桥本雅司
中须三奈子
堀内贵行
镰谷淳
冈田伸二郎
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Canon Inc
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Abstract

提供新型苯并[a]荧蒽化合物和具有极好发光效率、极好亮度和耐久性的有机发光器件。该苯并[a]荧蒽化合物由以下通式(I)表示：其中：R11～R22的至少一个表示由以下通式(i)表示的Rm：Rm＝-X1-Ar1(i)其中X1表示取代或未取代的亚苯基、或者取代或未取代的二价单环杂环基，并且Ar1表示以下基团(a)和(b)中的一个：(a)取代或未取代的稠合多环基，和(b)通过结合苯环、单环杂环和稠合多环中的两个或更多个而形成的复合取代基，该复合取代基可以具有取代基。

Description

苯并[a]荧蒽化合物和使用其的有机发光器件
技术领域
本发明涉及苯并[a]荧蒽化合物和使用该化合物的有机发光器件。
背景技术
有机发光器件是将包括荧光性有机化合物或磷光性有机化合物的薄膜夹在阳极和阴极之间的器件。另外，从各自电极注入电子和空穴以产生荧光性化合物或磷光性化合物的激子，由此在激子返回到基态时有机发光器件发光。
有机发光器件近来的发展显著，并且该器件的特性使发光器件能具有低施加电压下的高亮度、各种发射波长、高速响应性、薄而轻的重量。由这一事实表明该器件具有在多种应用中开发使用的潜力。
但是，当前的形势要求具有甚至更高亮度或更高转换效率的光输出。另外，在由长期使用引起的经时变化、由含有氧、湿气等的气氛气体引起的劣化的耐久性方面，仍存在许多有待解决的问题。
另外，当考虑应用于全色显示器或类似器件时，现有技术在克服涉及需要具有高色纯度的蓝、绿和红色发光的问题上仍不足。
作为解决上述问题的方法，提出过使用苯并荧蒽化合物作为有机发光器件用组分。例如，在日本专利申请公开No.H10-189247、日本专利申请公开No.2002-8867和Chem.Master.2003，15，4854-4862的每一篇中，使用苯并荧蒽化合物作为有机发光器件用组分。
发明内容
本发明的目的是提供新型苯并[a]荧蒽化合物。本发明的另一目的是提供具有极好的发光效率、极好的亮度和耐久性的有机发光器件。
本发明的苯并[a]荧蒽化合物由下面的通式(I)表示：
Figure G2008800009846D00021
其中：
R11～R22的至少一个表示由下面的通式(i)表示的Rm：
Rm＝-X1-Ar1            (i)
其中X1表示取代或未取代的亚苯基、或者取代或未取代的二价单环杂环基，并且Ar1表示以下基团(a)和(b)中之一：
(a)取代或未取代的稠合多环基，和
(b)通过结合苯环、单环杂环和稠合多环中的两个或更多个而形成的复合取代基，该复合取代基可以具有取代基；和
均未由Rm表示的R11～R22各自表示氢原子、卤素原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烯基、取代或未取代的炔基、取代或未取代的芳烷基、或者取代或未取代的氨基，并且均未由Rm表示的R11～R22可以彼此相同或不同。
根据本发明，能提供新型苯并[a]荧蒽化合物。另外，根据本发明，能提供具有极好的发光效率、极好的亮度和耐久性的有机发光器件。
由下面参照附图对示例性实施方案的说明，本发明的进一步的特点将变得明了。
附图说明
图1为说明根据本发明第一实施方案的有机发光器件的截面图。
图2为说明根据本发明第二实施方案的有机发光器件的截面图。
图3为说明根据本发明第三实施方案的有机发光器件的截面图。
图4为说明根据本发明第四实施方案的有机发光器件的截面图。
图5为说明根据本发明第五实施方案的有机发光器件的截面图。
具体实施方式
首先说明本发明的苯并[a]荧蒽化合物。
首先说明本发明的苯并[a]荧蒽化合物的第一实施方案。此处，本发明的苯并[a]荧蒽化合物的第一实施方案是由下面的通式(I)表示的化合物。
Figure G2008800009846D00031
在通式(I)中，R11～R22的至少一个表示由下面的通式(i)表示的Rm：
Rm＝-X1-Ar1           (i)
在通式(i)中，X1表示取代或未取代的亚苯基、或者取代或未取代的二价单环杂环基。
X1表示的二价单环杂环基的例子包括亚噻吩基、亚吡咯基、亚吡啶基、亚嘧啶基、亚噁唑基、亚噁二唑基、亚噻唑基和亚噻二唑基。
亚苯基和单环杂环基可以具有的取代基的例子包括：烷基例如甲基、乙基和丙基；芳烷基例如苄基和苯乙基；芳基例如苯基、联苯基、萘基、芴基和芘基；杂环基例如噻吩基、吡咯基和吡啶基；氨基基因例如二甲基氨基、二乙基氨基、二苄基氨基、二苯基氨基、二(甲苯基)氨基和二(苯甲醚基)氨基；烷氧基例如甲氧基、乙氧基和丙氧基；芳氧基例如苯氧基；卤素原子例如氟和氯；氰基；和硝基。
在通式(i)中，Ar1表示以下基团(a)和(b)中之一。优选地，Ar1表示基团(a)。
(a)取代或未取代的稠合多环基。
(b)通过结合苯环、单环杂环和稠合多环中的两个或更多个而形成的复合取代基(该复合取代基可以具有取代基)。
在基团(a)中，稠合多环基的例子包括萘基、薁基、并环戊二烯基、茚基、蒽基、芘基、indacenyl基、苊基、菲基、phenalenyl基、荧蒽基、苯并荧蒽基、醋菲基(acephenanthryl group)、醋蒽基、苯并[9，10]菲基、
Figure G2008800009846D00041
基、并四苯基、苝基、并五苯基、芴基、咪唑基、咔唑基、吖啶基和phenanthrolyl基。
由基团(b)表示的复合取代基的具体例子包括联苯基、苯基吡啶基、联噻吩基、联芴基、芴基苯基、苯基蒽基、联吡啶基和下面的取代基。
基团(a)和(b)中的稠合多环基和复合取代基可具有的取代基的例子包括：烷基例如甲基、乙基和丙基；芳烷基例如苄基和苯乙基；芳基例如苯基、联苯基、萘基、芴基、芘基和荧蒽基；杂环基例如噻吩基、吡咯基和吡啶基；氨基基团例如二甲基氨基、二乙基氨基、二苄基氨基、二苯基氨基、二(甲苯基)氨基和二(苯甲醚基)氨基；烷氧基例如甲氧基、乙氧基和丙氧基；芳氧基例如苯氧基；卤素原子例如氟和氯；氰基；和硝基。
另外，在通式(I)中，均未由Rm表示的R11～R22各自表示氢原子、卤素原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烯基，取代或未取代的炔基、取代或未取代的芳烷基、或者取代或未取代的氨基。
R11～R22表示的卤素原子的例子包括氟、氯、溴和碘。
R11～R22表示的烷基的例子包括甲基、乙基、正丙基、异丙基、正丁基、叔丁基、仲丁基、辛基、1-金刚烷基和2-金刚烷基。
R11～R22表示的烷氧基的例子包括甲氧基、乙氧基和丙氧基。
R11～R22表示的芳氧基的例子包括苯氧基、4-甲基苯氧基和萘氧基。
R11～R22表示的烯基的例子包括乙烯基、丙烯基、丁烯基、苯乙烯基和二苯基乙烯基。
R11～R22表示的炔基的例子包括乙炔基、丙炔基、丁炔基和苯乙炔基。
R11～R22表示的芳烷基的例子包括苄基和苯乙基。
R11～R22表示的氨基基团的例子包括二甲基氨基、二乙基氨基、二苄基氨基、二苯基氨基、二(甲苯基)氨基、二叔丁基氨基和二(苯甲醚基)氨基和咔唑基。
烷基可以具有的取代基的例子包括：烷基例如甲基、乙基和丙基；芳烷基例如苄基和苯乙基；芳基例如苯基和联苯基；杂环基例如噻吩基、吡咯基和吡啶基；氨基基团例如二乙基氨基、二苄基氨基、二苯基氨基、二(甲苯基)氨基和二(苯甲醚基)氨基；烷氧基例如甲氧基、乙氧基和丙氧基；芳氧基例如烷氧基和苯氧基；卤素原子例如氟和氯；氰基；和硝基。
均未由Rm表示的R11～R22可以彼此相同或不同。
由于未取代的苯并[a]荧蒽有具有高度平面性的结构，苯并[a]荧蒽容易引起由发光层中的浓度猝灭导致的有机发光器件亮度的降低。鉴于以上内容，当通式(I)中R11～R22的至少一个表示具有大的空间位阻的Rm时，发光层中的浓度猝灭受到抑制，这样能抑制有机发光器件的亮度的降低。
另外，具有大空间位阻的Rm的引入使苯并[a]荧蒽化合物分子能避免互相重叠。结果，使苯并[a]荧蒽化合物的升华性质和沉积稳定性提高，使该化合物的结晶性降低，并且通过该化合物的高玻璃化转变温度使由该化合物制成的膜的稳定性提高。
下文中，以下示出由通式(I)表示的化合物的具体例子。但本发明并不限于这些例子。
本发明的苯并[a]荧蒽化合物能用作形成有机发光器件的材料。另外，掺入作为有机发光器件用组分的本发明的苯并[a]荧蒽化合物使有机发光器件的发光效率、色纯度和耐久性提高。以下将说明使这些性质提高的原因。
本发明的苯并[a]荧蒽化合物含有五元环结构。此处，本发明的苯并[a]荧蒽化合物通过由五元环结构产生的吸电子性而具有电子注入性。因此，使用本发明的苯并[a]荧蒽化合物作为形成有机发光器件的材料能降低使该器件驱动的电压，因为该使用使从阴极产生的电子得以有效地传输。结果能提高有机发光器件的发光效率。另外，该使用也有利于延长有机发光器件的寿命。
另外，向本发明的苯并[a]荧蒽化合物中引入取代基能适当地调节该化合物的HOMO和LUMO能级。因此，在考虑作为载流子的空穴的注入量和作为另一种载流子的电子的注入量之间的平衡时能对该化合物的分子进行设计。
根据J.Phys.Chem.1994，98，5639-5643，从有机发光器件发出的光的色纯度上的改善要求形成该器件的发光材料满足以下要求：
1.发光材料分子表现出小的Stokes位移(与基态中的分子结构相比激发态中的分子结构的变化小)；
2.发光材料分子的缔合受到抑制；和
3.发光材料分子的发射光谱具有窄的半宽度。
此处，特别地，将由通式(I)中的Arl表示的芴基、苯并荧蒽基、荧蒽基、芘基、苝基等作为取代基引入到本发明的苯并[a]荧蒽化合物中表现出小的Stokes位移。
另外，如上所述，本发明的苯并[a]荧蒽化合物有具有大空间位阻的取代基，因此该化合物分子的缔合受到抑制。
另外，因为能将各种取代基的任一个引入该化合物中，所以能设计符合所需发光色的本发明的苯并[a]荧蒽化合物的分子。
形成有机发光器件的材料的化学稳定性是该器件耐久性的重要因素。
本发明的苯并[a]荧蒽化合物是化学稳定的，因为该化合物借助源于五元环结构的吸电子效应而表现出对单线态氧分子等的亲电反应的低反应性。
另外，当该化合物在其苯并[a]荧蒽骨架中具有取代基时，进一步提高本发明的苯并[a]荧蒽化合物的化学稳定性。该取代基优选为由碳原子和氢原子形成的取代基。
此处，优选将由碳原子和氢原子形成的取代基引入式(I)的苯并[a]荧蒽化合物中的R15的位置。由于该位置是在苯并[a]荧蒽骨架中亲电反应性最高的取代位置，将与氢原子相比具有较低消除能力和较低化学反应性的取代基引入该位置进一步使苯并[a]荧蒽化合物的化学稳定性提高。
更优选将空间上体积大的取代基例如通式(I)中的Rm引入式(I)的R15位置，因为通过降低取代基的空间位阻对该化合物的化学反应性的影响而进一步提高该化合物自身的化学稳定性。
另一方面，当取代苯并[a]荧蒽骨架的取代基具有比苯并[a]荧蒽宽的带隙时，源自该取代基的发光在该化合物的分子自身的发光中变成主导。这是因为该化合物的HOMO或LUMO定域于苯并[a]荧蒽骨架中。在这种情形中，有机发光器件的耐久性得到提高，因为苯并[a]荧蒽骨架的化学稳定性的影响得到进一步提高。
接下来，详细说明本发明的有机发光器件。
本发明的有机发光器件包括阳极、阴极和包括有机化合物的层，该层插入阳极和阴极之间。另外，包括有机层的层含有至少一种本发明的苯并[a]荧蒽化合物。
下文中，将参照附图详细说明本发明的有机发光器件。
附图标记1表示基板；2，阳极；3，发光层；4，阴极；5，空穴传输层；6，电子传输层；7，空穴注入层；8，空穴/激子阻挡层；和10、20、30、40和50均表示有机发光器件。
图1为说明根据本发明第一实施方案的有机发光器件的截面图。图1的有机发光器件10包括阳极2、有机发光层3和阴极4，其依次形成在基板1上。有机发光器件10在发光层3由具有包括空穴传输能力、电子传输能力和发光性能的所有性能的化合物形成的情形或者发光层3由各自具有空穴传输能力、电子传输能力和发光性能的其中一种性能的化合物的混合物形成的情形中有用。
图2为说明根据本发明第二实施方案的有机发光器件的截面图。图2的有机发光器件20包括阳极2、空穴传输层5、电子传输层6和阴极4，其依次形成在基板1上。有机发光器件20在具有电子传输性能和空穴传输性能的其中一种性能的有机发光化合物与只具有电子传输性能或只具有空穴传输性能的有机化合物结合使用的情形中有用。另外，在发光器件20中，空穴传输层5或电子传输层6用作发光层。
图3为说明根据本发明第三实施方案的有机发光器件的截面图。图3的有机发光器件30对将发光层3插在图2的有机发光器件20中的空穴传输层5和电子传输层6之间的结构进行说明。在有机发光器件30中，将载流子传输作用和发光作用互相分离。因此，能将该器件适当地与各自具有空穴传输性能、电子传输性能和发光性能的其中一种性能的有机化合物结合使用。因此，材料选择上的自由度极大地增加，也能使用发射波长互不相同的各种化合物。结果能使发光色的范围变宽。另外，通过有效地在中央发光层3中捕捉载流子或激子，能提高有机发光器件30的发光效率。
图4为说明根据本发明第四实施方案的有机发光器件的截面图。图4的有机发光器件40对将空穴注入层7设置在图3的有机发光器件30中的阳极2和空穴传输层5之间的结构进行说明。在有机发光器件40中空穴注入层7的设置赋予改善阳极2和空穴传输层5之间的粘附性或者空穴注入性能的效果，并且对降低器件的驱动电压有效。
图5为说明根据本发明第五实施方案的有机发光器件的截面图。图5的有机发光器件50对在图3的有机发光器件30中将用于抑制空穴或激子向阴极4侧逃逸的层(空穴/激子阻挡层8)插在发光层3和电子传输层6之间的结构进行说明。使用具有极高电离电位的化合物作为空穴/激子阻挡层8使有机发光器件50的发光效率提高。
应当指出的是，根据第一至第五实施方案的器件结构只是非常基本的结构，并且使用本发明的苯并荧蒽化合物的有机发光器件的结构并不限于这些。例如，可将绝缘层设置在电极和有机层之间的界面上，可将粘合层或干涉层设置在其上，并且空穴传输层可以由具有不同电离电位的两层形成。
本发明的苯并[a]荧蒽化合物能用在上述第一至第五实施方案的任一个中。
本发明的苯并[a]荧蒽化合物能作为有机发光器件用材料使用。具体地，该化合物能用作形成该器件的空穴传输层、电子传输层和发光层的每一层的材料。在这种情形中，可使用一种上述种类的苯并[a]荧蒽化合物或多种上述种类的苯并[a]荧蒽化合物。或者，可将该苯并[a]荧蒽化合物掺入多层中的每一层。本发明的苯并[a]荧蒽化合物的使用使有机发光器件的发光效率和寿命得到提高。
特别优选使用本发明的苯并[a]荧蒽化合物作为形成发光层的材料，不仅因为该化合物能用在各个实施方案的任一个中，而且因为能在色纯度、发光效率和寿命方面提高有机发光器件的性能。
发光层可以仅由本发明的苯并[a]荧蒽化合物形成。或者，发光层可以由主体和客体形成。此处，本发明的苯并[a]荧蒽化合物能用在用作客体的掺杂剂材料和均用作主体的荧光性材料和磷光性材料的任意一种中。本发明的苯并[a]荧蒽化合物作为发光层中的主体或客体的使用能在色纯度、发光效率和寿命方面提高有机发光器件的性能。
当本发明的苯并[a]荧蒽化合物用作发光层用客体时，对对应的主体没有特别限制，从以下观点考虑优选稠合多环衍生物：应提供由稳定的无定形膜形成的有机发光器件。此处，为了可提供具有高效率和耐久性的有机发光器件，主体本身的发射量子产率必须要高，并且主体本身必须是化学稳定的。满足这些要求的优选的稠合多环衍生物为，例如，芴衍生物、芘衍生物、荧蒽衍生物或苯并荧蒽衍生物。这些化合物中每个具有高发射量子产率，并且是化学稳定的。
此处，当本发明的苯并[a]荧蒽化合物用作发光层用客体时，该化合物的含量，相对于形成该发光层的材料的总重量，优选为0.1wt％～30wt％；从抑制浓度猝灭的观点考虑，该含量更优选为0.1wt％～15wt％。
另一方面，当本发明的苯并[a]荧蒽化合物用作发光层用主体时，对对应的客体并无特别限制，并且能依据例如所需的发光色进行适当选择。另外，通过用以下化合物和客体一起掺杂该层，能根据需要使用空穴传输性化合物、电子传输性化合物等以及客体。
本发明的有机发光器件使用本发明的苯并[a]荧蒽化合物尤其作为形成该器件的发光层的材料。另外，根据需要本发明的有机发光器件能将例如常规已知的低分子量类和聚合物类空穴传输性化合物、发光化合物和电子传输性化合物的任一种与本发明的苯并[a]荧蒽化合物一起使用。
空穴传输性化合物的例子包括三芳基胺衍生物、芳基二胺衍生物、酞菁衍生物、卟啉衍生物、聚(乙烯基咔唑)、聚(亚甲硅烷基)、聚(噻吩)和其它导电性聚合物。
除本发明的苯并[a]荧蒽化合物之外的发光化合物的例子包括：稠环芳族化合物(包括萘衍生物、菲衍生物、芴衍生物、芘衍生物、并四苯衍生物、六苯并苯衍生物、
Figure G2008800009846D00111
衍生物、苝衍生物、9，10-二苯基蒽衍生物和红荧烯)；喹吖啶酮衍生物、吖啶酮衍生物；香豆素衍生物；吡喃衍生物；尼罗红；吡嗪衍生物；苯并咪唑衍生物；苯并噻唑衍生物；苯并噁唑衍生物、茋衍生物；有机金属络合物(包括有机铝络合物例如三(8-羟基喹啉合)铝和有机铍络合物)；和高分子衍生物例如聚(亚苯基亚乙烯基)衍生物、聚(芴)衍生物、聚(亚苯基)衍生物、聚(亚噻吩基亚乙烯基)衍生物和聚(乙炔)衍生物。
电子传输性化合物的例子包括噁二唑衍生物、噁唑衍生物、噻唑衍生物、噻二唑衍生物、吡嗪衍生物、三唑衍生物、三嗪衍生物、苝衍生物、喹啉衍生物、喹喔啉衍生物、芴酮(fluorenone)衍生物、蒽酮衍生物、菲咯啉衍生物和有机金属络合物。
可取的阳极材料具有尽可能大的功函数。可利用的阳极的例子包括：金属单质例如金、铂、银、铜、镍、钯、钴、硒、钒和钨，以及它们的合金；和金属氧化物例如氧化锡、氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌。另外，也可使用导电性聚合物例如聚苯胺、聚吡咯、聚噻吩和聚苯硫醚。这些电极物质的每一种可以单独使用。或者，也可以将它们的两种或更多种结合使用。另外阳极可以由单层形成并且可以由多层形成。
可取的阴极材料具有尽可能小的功函数。可利用的阴极的例子包括：金属单质例如锂、钠、钾、钙、镁、铝、铟、钌、钛、锰、钇、银、铅、锡和铬。或者，这些金属单质可作为合金而结合使用。例如，能使用下面的合金：锂-铟、钠-钾、镁-银、铝-锂、铝-镁和镁-铟合金。另外也可以使用金属氧化物例如氧化铟锡(ITO)。这些电极物质的每一种可以单独使用或者两种或更多种结合使用。另外，阴极可以由单层形成并且可以由多层形成。
可在本发明中使用的基板包括：不透明基板例如金属基板和陶瓷基板；和透明基板例如玻璃、石英和塑料片材基板，但并不特别限于这些材料。
另外，滤色膜、荧光色转换膜、介电反射膜等可以用于基板中以控制发射的光。通过连接到在基板上制备的薄膜晶体管(TFT)也能制备本发明的器件。
而且，关于器件的取出光的方向，底部发射结构(将光从基板侧取出的结构)和顶部发射结构(将光从与基板相反侧取出的结构)均能接受。
通过方法例如真空气相沉积法、溶液施涂法、包括使用激光等的转印法或者喷涂法制备本发明的有机发光器件。此处，含有本发明的苯并[a]荧蒽化合物的有机层优选通过例如真空气相沉积法或溶液施涂法形成，因为待形成的该层自身的结晶等几乎不发生，并且该层的经时稳定性优异。
下文中，将参考实施例进一步具体说明本发明，但本发明并不限于它们。
(实施例1)
示例化合物B-1的合成
Figure G2008800009846D00131
(a)中间体化合物1-2的合成
将1.0g(3.96mmol)的化合物1-1和50ml的二氯甲烷装入200-ml的三口烧瓶，并在氮气气氛下搅拌该混合物，同时用冰冷却。在搅拌期间，将通过在10ml的二氯甲烷中溶解0.20ml的溴制备的溶液滴到该混合物中。然后，搅拌得到的混合物5小时。反应后，过滤反应溶液并用甲醇清洗，由此得到1.24g的中间体1-2(黄色晶体)(95％的收率)。
(b)示例化合物B-1的合成
将0.205g(0.623mmol)的化合物1-2、0.164g(0.415mmol)的化合物1-3、50ml的甲苯和20ml的乙醇装入200-ml的三口烧瓶，并在室温下在氮气气氛下搅拌该混合物。在搅拌期间，将通过在50ml水中溶解5g的碳酸铯制备的水溶液滴到该混合物中，然后将0.100g的四(三苯膦)钯(0)加入该混合物中。将得到的混合物的温度升至77℃，并将该混合物搅拌5小时。反应后，用甲苯萃取该有机层，用无水硫酸钠进行干燥，并用硅胶柱(使用甲苯和庚烷的混合展开溶剂)提纯，由此得到0.179g的示例化合物B-1(黄色晶体)(83％的收率)。
质谱确认示例化合物B-1具有520的M+。
1H-NMR(CDCl3，400MHz)σ(ppm)：8.87(d，1H)，8.46(d，1H)，8.07-8.05(m，3H)，7.92-7.75(m，7H)，7.71-7.69(t，1H)，7.64-7.59(m，3H)，7.53-7.42(m，4H)，7.40-7.36(m，2H)，1.59(s，6H)
另外，在具有10-6mol/l浓度的该化合物在甲苯中的稀溶液中的发射光谱显示具有510nm波长的良好绿色。用荧光光度计(由Hitachi，Ltd.制造的F-4500)在340nm的激发波长下进行该测定。
另外，通过使用下表1中所示中间体的对应一个作为中间体1-3能合成每一个示例化合物A-1和B-7。
表1
Figure G2008800009846D00141
(实施例2)
通过下面的方法对示例化合物B-1评价其发射量子收率。
具体地，首先，制备具有10-6mol/l浓度的示例化合物B-1在甲苯中的稀溶液。其次，用分光光度计(由Hitachi，Ltd.制造的U-3310)测定在340nm的波长下稀溶液的吸光度。
其次，当将340nm的波长定义为激发波长时用荧光光度计(由Hitachi，Ltd.制造的F-4500)测定稀溶液的发射光谱，并由得到的发射光谱计算发射峰的面积。
将二苯基蒽的值设定为1.0时，通过使用上述的吸光度和发射峰面积来计算该化合物的发射量子收率的相对值，并定义为相对量子产率1。同时，将苯并[a]荧蒽的值设定为1.0时，类似地计算该化合物的发射量子产率的相对值，并定义为相对量子产率2。表2示出示例化合物B-1中相对量子产率1和相对量子产率2的计算结果。
<比较例1>
制备具有10-6mol/l浓度的以下所示化合物2-1在甲苯中的稀溶液。
Figure G2008800009846D00151
用与实施例2中同样的方式对在甲苯中的稀溶液的吸收光谱和发射光谱各自进行测定。另外，用与实施例2中同样的方式由得到的吸收光谱和得到的发射光谱各自计算相对量子产率1和相对量子产率2。表3示出计算的结果。
<比较例2>
制备具有10-6mol/l浓度的以下所示化合物2-2在甲苯中的稀溶液。
Figure G2008800009846D00152
用与实施例2中同样的方式对在甲苯中的稀溶液的吸收光谱和发射光谱各自进行测定。另外，用与实施例2中同样的方式由得到的吸收光谱和得到的发射光谱各自计算相对量子产率1和相对量子产率2。表2示出计算的结果。
表2
  化合物No.  相对量子产率1  相对量子产率2
 实施例2   B-1   0.34   1.78
 比较例1   2-1   0.19   1.0
 比较例2   2-2   0.23   1.21
<实施例3>(发光器件的制备)
作为阳极，通过溅射法在玻璃基板上形成具有120nm膜厚的氧化铟锡(ITO)膜。其次，依次用丙酮和异丙醇对得到的基板进行超声波净化。然后，用沸腾的IPA清洗产物，接着进行干燥。另外，对产物进行UV/臭氧净化。将这样处理的玻璃基板用作透明导电性支撑基板。
其次，通过旋涂法在透明导电性支撑基板上由以下所示的化合物3-1在氯仿中的0.1wt％溶液形成具有20nm厚的膜，由此形成空穴传输层。
Figure G2008800009846D00161
化合物3-1
其次，在10-5Pa的真空室中通过基于电阻加热的真空气相沉积法连续形成任何其它有机层和形成阴极的层。具体地，首先，将作为客体的示例化合物B-1和以下示出的化合物3-2以5∶95的重量浓度比进行共沉积以作为发光层。此时，发光层的厚度为20nm。其次，将以下示出的化合物3-3形成具有40nm厚的电子传输层。其次，将LiF形成具有0.5nm厚的金属电极层1。其次，将Al形成具有150nm厚的金属电极层2。此处，金属电极层1和金属电极层2各自起到阴极的作用。
Figure G2008800009846D00171
化合物3-2                        化合物3-3
这样，制备有机发光器件。
在这个实施例中对制备的有机发光器件施加6.1V的电压。结果，观察到该器件在18mA/cm2的电流密度下发出具有1720cd/m2发射亮度的绿光。
另外，将电流密度保持在165mA/cm2的同时在氮气气氛下将这个实施例的有机发光器件连续驱动100小时。结果，与器件的起始亮度相比，驱动100小时后该器件的亮度下降的百分比小到低于或等于5％。
尽管参照示例性实施方案对本发明进行了说明，但应理解本发明并不限于公开的示例性实施方案。对下面的权利要求的范围应给予最宽泛的解释以至包括所有这样的变形和等效结构以及功能。
该申请要求于2007年5月16日提交的日本专利申请No.2007-130526和于2008年4月2日提交的日本专利申请No.2008-095674的权益，由此在本文中将其全文引为参考。

Claims (6)

1.由以下通式(I)表示的苯并[a]荧蒽化合物：
Figure FSB00001034227300011
其中：
R15表示由以下通式(i)表示的Rm：
Rm＝-X1-Ar1    (i)
其中X1表示未取代的亚苯基，并且Ar1表示取代或未取代的稠合多环基，
其中所述稠合多环基选自芴基、苯并荧蒽基、芘基和苝基，所述稠合多环基可具有烷基作为取代基；并且
均未由Rm表示的R11～R22各自表示氢原子。
2.根据权利要求1的苯并[a]荧蒽化合物，其中Ar1表示取代或未取代的芴基，所述芴基可具有烷基作为取代基，并且在所述芴基的9位将芴基取代。
3.根据权利要求1的苯并[a]荧蒽化合物，其由以下结构表示：
Figure FSB00001034227300012
4.根据权利要求1的苯并[a]荧蒽化合物，其由以下结构表示：
Figure FSB00001034227300021
5.有机发光器件，包括：
阳极；
阴极；和
包括有机化合物的层，将该层插入该阳极和该阴极之间，
其中该包括有机化合物层含有至少一种根据权利要求1的苯并[a]荧蒽化合物。
6.根据权利要求5的有机发光器件，其中在发光层中含有该苯并[a]荧蒽化合物。
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CN101547877A (zh) 2009-09-30
JP5361238B2 (ja) 2013-12-04
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