CN102227829A - 具有新型空穴传导材料的oled - Google Patents
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
本发明涉及有机发光二极管(OLED)电致发光器件领域,其包括具有螺二
Description
技术领域
本发明涉及有机发光二极管(OLED)电致发光(electroluminescent)器件领域,其包含含有有机金属配位化合物的光发射层,所述有机金属配位化合物具有特定的具有高三重态(triplet)能量的配体。
背景技术
尽管有机电致发光(EL)器件已为人所知超过二十年,但由于数种不利影响,它们的性能通常是受限制的。在其最简单的形式中,有机EL器件包含用于空穴注入的阳极,用于电子注入的阴极和夹在这些电极之间以支持产生光发射的电荷复合的有机介质。这些器件通常被称为有机发光二极管(OLED)。目前,最有效的发射体是磷光发射体,其中辐射跃迁是从三重态到基态。通常,铱或铂络合物被用于现有技术的OLED中。一般地,5重量%至15重量%的磷光发射体被掺杂进材料中。磷光发射体的使用对基质材料的三重态能级(triplet level)有严格要求。
如果基质的三重态能级低于发射体的三重态能级,则能量从发射体转移至基质,淬灭光的发射。只有基质的三重态能级高于发射体的三重态能级,能量转移才被抑制并且所得到的OLED显示是高量子效率的。量子效率是进入OLED的注入电荷载流子对和出射光子(extracted photons)的比值。
对于红色、黄色和黄绿色发射体这一要求并不难满足,因为大多数基质材料的三重态能级与520-550 nm的发射波长对应。只有对于波长小于520 nm,并且尤其小于470 nm的发射体,才只有极少的适合的基质材料。
由于许多磷光金属络合物良好地传导电子,因此使用传导空穴的基质材料。
因此,对具有高三重态能级的空穴传导材料(hole-conducting materials)存在持续需求。
发明内容
因此,本发明的一个目标是提供包含具有高三重态能级的新型空穴传导材料的OLED。
通过包含具有结构I的空穴传导材料的OLED解决了这一目标:
I
其中R1、R2、R3 和R4独立地选自包含部分II和III的组:
II
III
其中每个RI、RII独立地选自包括氢、烷基、烷氧基、卤代烷基、环烷基、杂环烷基、芳基、杂芳基的组。
如稍后将展示的那样,这些材料具有出人意料地高的三重态能级。从现有技术公知,具有这种三重态能级的基质材料可用于发射波长最高约460 nm的蓝色磷光发射体。
通用基团定义
在整个说明书和权利要求中,使用通用基团,例如烷基、烷氧基、芳基。除非另有说明,否则以下是可以用于在本文披露的化合物中发现的通用基团的优选基团:
烷基:直链和支链的C1-C8-烷基,
环烷基:C3-C8-环烷基,
烷氧基:C1-C6-烷氧基,
芳基:选自分子量低于300的同芳香性的(homoaromatic)化合物,
杂芳基:选自由吡啶基;嘧啶基;吡嗪基;三唑基; 哒嗪基;1,3,5-三嗪基;喹啉基; 异喹啉基; 喹喔啉基;咪唑基;吡唑基;苯并咪唑基;噻唑基; 唑烷基;吡咯基;咔唑基;吲哚基和异氮茚基组成的组,其中所述杂芳基可通过所选杂芳基的环中的任何原子连接到化合物,
杂环烷基:选自由吡咯啉基;吡咯烷基;吗啉基;哌啶基;哌嗪基;六亚甲基亚胺;1,4-哌嗪基;四氢噻吩基;四氢呋喃基;1,4,7-三氮杂环壬烷基;1,4,8,11-四氮杂环十四烷基;1,4,7,10,13-五氮杂环十五烷基;1,4-二氮杂-7-硫杂环壬烷基;1,4-二氮杂-7-氧杂环壬烷基;1,4,7,10-四氮杂环十二烷基;1,4-二烷基;1,4,7-三硫杂环壬烷基;四氢吡喃基;和唑烷基组成的组,其中所述杂环烷基可通过所选杂环烷基的环中的任何原子连接到化合物,
卤代烷基:选自由单、双、三、多和全卤代直链和支链C1- C8烷基组成的组
除非另有说明,否则以下是可以应用于在本文披露的化合物中发现的基团的更优选的基团限制:
烷基:直链和支链的C1-C6-烷基,
环烷基:C6-C8-环烷基,
烷氧基:C1-C4-烷氧基,
芳基:选自由苯基;联苯基;萘基;蒽基;和菲基组成的组,
杂芳基:选自由以下组成的组:
吡啶基;嘧啶基;喹啉基;吡唑基;三唑基; 异喹啉基;咪唑基;和唑烷基,其中所述杂芳基可通过所选杂芳基的环中的任何原子连接到化合物,杂亚芳基:选自由吡啶2,3-二基;吡啶-2,4-二基;吡啶-2,6-二基;吡啶-3,5-二基;喹啉-2,3-二基;喹啉-2,4-二基;异喹啉-1,3-二基;异喹啉-1,4-二基;吡唑-3,5-二基;和咪唑-2,4–二基组成的组,
根据本发明的一个优选实施方案,R1、R2、R3和R4中至少一个相对于氧处于对位位置。这已经显示出对于本发明中的各种应用进一步增加所述材料的有益性能。
根据本发明的一个优选实施方案,R1=R2和/或R3=R4;更优选R1=R2=R3=R4。这已经显示出对于本发明中的各种应用进一步增加所述材料的有益性能。
根据本发明的一个优选实施方案,RI、RII中至少一个相对于氮处于对位位置。这已经显示出对于本发明中的各种应用进一步增加所述材料的有益性能。
根据本发明的一个优选实施方案,RI、RII独立地选自包含甲基、乙基、丙基、异丙基、丁基和叔丁基的组。这已经显示出对于本发明中的各种应用进一步增加所述材料的有益性能,特别是就所述材料在各种溶剂中的溶解性而言。
根据本发明的一个优选实施方案,本发明的化合物I用于阻止由OLED的一部分到该OLED的另一部分的三重态激子(triplet exciton)扩散。
本发明的化合物可例如由螺二吨(spirobixanthen)制得,其根据R. G. Clarkson, M. Gomberg, J. Am. Chem. Soc. 1930, 52, 2887 (2881-2891)连同其它参考文献是可行的,通过
-亲电子和/或自由基卤化和
-使用钯催化剂的Hartwig-Buchwald胺化和/或使用铜的Ullman-反应型胺化。
根据本发明的一种优选的照明单元包含如上所述的OLED器件,并可用于家庭应用,商店照明,家居照明,重点照明(accent lighting),局部照明(spot lighting),剧场照明,光纤应用,投影系统,自照明显示器(self-lit displays),医疗照明应用,像素化显示器(pixelated displays),分段显示器(segmented displays),警示标志,指示标志,装饰照明等。
上述组分,以及要求保护的组分和将根据本发明在所描述的实施方案中使用的组分,就其大小、形状、材料选择和技术概念而言不受任何特殊例外限制,使得可以没有限制的应用在相关领域中已知的选择标准。
本发明所述目标的另外的细节、特征、特性和优势披露在从属权利要求、附图和相应附图和实施例的下述描述中,所述实施例以示例性方式示出了根据本发明的OLED的几个优选实施方案。
具体实施方式
实施例I
它可如实施例I那样制得(使用不同的咔唑)并具有436 nm的三重态能级。
所描述的本发明的材料可以两种方式使用:在一个或多个发光层中作为基质材料(通常这些层掺杂有磷光发射体)或作为三重态激子阻挡层。OLED的一种典型结构如下:
阳极-ITO120 nm/空穴注入层,10 nm/空穴传输层30 nm/发射体层30 nm/空穴阻挡层10 nm/电子传输层40 nm/电子注入层1 nm/阴极-Al 100 nm。在这里,所述具有高三重态能级的材料被用于两个层中:
-在发光层中,以重量百分比≥1%至≤50%,优选≥5%至≤20%,更优选≥5%至≤15%掺杂有磷光发射体。
-在空穴传输层中,以阻挡三重态激子扩散出发射区。
在上述详细实施方案中元素和特征的特定结合仅仅是示例性的;还明确地考虑了这些教导与本申请和通过引用并入的专利/申请中的其他教导的交换和替代。如本领域的技术人员将认识到的那样,本领域的普通技术人员不偏离要求保护的本发明的精神与范围,能够认识本文所述的内容的变更、修改和其他实施。因此,上述描述只是通过举例的方式,而不是意图作为限制。本发明的范围定义在下列权利要求和其等价物中。此外,在说明书和权利要求中使用的附图标记不限制要求保护的本发明的范围。
Claims (9)
2. 根据权利要求1所述的OLED,其中R1、R2、R3和R4中的至少一个相对于氧处在对位上。
3. 根据权利要求1所述的OLED,其中R1=R2和/或R3=R4。
4. 根据权利要求1所述的OLED,其中R1=R2=R3=R4。
5. 根据权利要求1所述的OLED,其中RI、RII中的至少一个相对于氮处在对位上。
6. 根据权利要求1所述的OLED,其中RI、RII独立地选自包括甲基、乙基、丙基、异丙基、丁基和叔丁基的组。
7. 根据权利要求1至6任意一项所述的OLED,其中所述化合物I被用于阻止由该OLED的一部分到该OLED的另一部分的三重态激子扩散。
8. 根据权利要求1至7任意一项所述的OLED,其中所述化合物I作为基质材料用在一个或多个发射层中。
9. 根据本发明的照明单元,其包括根据权利要求1至7任意一项所述的OLED并用于一个或多个下列应用:家庭应用,商店照明,家居照明,重点照明,局部照明,剧场照明,光纤应用,投影系统,自照明显示器,医疗照明应用,像素化显示器,分段显示器,警示标志,指示标志,装饰照明。
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TWI491612B (zh) | 2015-07-11 |
US20110227054A1 (en) | 2011-09-22 |
CN102227829B (zh) | 2014-03-26 |
JP5662331B2 (ja) | 2015-01-28 |
WO2010061315A1 (en) | 2010-06-03 |
KR20110102371A (ko) | 2011-09-16 |
JP2012510152A (ja) | 2012-04-26 |
EP2371014B1 (en) | 2013-06-19 |
US8435647B2 (en) | 2013-05-07 |
EP2371014A1 (en) | 2011-10-05 |
TW201030008A (en) | 2010-08-16 |
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