CN101160369B - 红色磷光化合物和使用它的有机电致发光器件 - Google Patents
红色磷光化合物和使用它的有机电致发光器件 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及有机电致发光器件,更特别地,涉及红色磷光化合物和使用它的有机电致发光器件。最特别地,本发明涉及用作有机电致发光器件的发光层中的掺杂剂的红色磷光体,所述有机电致发光器件通过顺次沉积阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极而形成。
背景技术
近年来,随着显示器件的尺寸越来越大,越来越需要占用较少空间的平板显示器件。该平板显示器件包括有机电致发光器件,也称为有机发光二极管(OLED)。该有机电致发光器件的技术正在以巨大的速度发展,已经公开了许多原型。
当电荷注入到在电子注入电极(阴极)和空穴注入电极(阳极)之间形成的有机层中时,有机电致发光器件发光。更具体地,当电子和空穴形成一对时发光,新产生的电子-空穴对衰减。可以在柔性透明基板如塑料上形成有机电致发光器件。也可以在比等离子体显示板或无机电致发光(EL)显示器中需要的电压更低的电压(即低于或等于10V的电压)下驱动有机电致发光器件。有机电致发光器件的有利之处在于,其与其它显示器件相比消耗更少的能量和提供优异的颜色显示。而且,由于有机电致发光器件通过使用三色(即绿色、蓝色和红色)可以再现图片,所以有机电致发光器件被广泛地认为是可以再现清晰图像的下一代颜色显示器件。
制造有机电致发光(EL)器件的过程描述如下:
(1)将阳极材料涂布在透明基板上。一般地,使用氧化铟锡(ITO) 作阳极材料。
(2)在阳极材料上沉积空穴注入层(HIL)。空穴注入层由具有10纳米(nm)至30纳米(nm)厚度的铜酞菁(CuPc)层形成。
(3)然后沉积空穴传输层(HTL)。空穴传输层主要由4,4’-双[N-(1-萘基)-N-苯氨基]联苯(NPB)形成,其用真空蒸发处理,然后涂布至具有30纳米(nm)至60纳米(nm)的厚度。
(4)此后,形成有机发光层。此时,如果需要,可以加入掺杂剂。在绿色发光的情况中,有机发光层一般由真空蒸发至具有30纳米(nm)至60纳米(nm)厚度的三(8-羟基喹啉酸)铝(Alq3)形成。并且使用MQD(N-甲基喹吖啶酮)作掺杂剂(或杂质)。
(5)在有机发光层上依次形成电子传输层(ETL)和电子注入层(EIL),或在有机发光层上形成电子注入/传输层。在绿色发光的情况中,步骤(4)的Alq3具有优异的电子传输能力。因此,并非必需地需要电子注入和传输层。
(6)最后涂布阴极层,在整个结构上涂布保护层。
依照在上述结构中形成发光层的方法,决定了分别发出(或显示)蓝、绿和红颜色的发光器件。作为发光材料,由从每个电极注入的电子和空穴的重组而形成激子。单线态激子发射荧光,三线态激子发射磷光。发射荧光的单线态激子具有25%的形成可能性,而发射磷光的三线态激子具有75%的形成可能性。因此,与单线态激子相比,三线态激子提供更大的发光效率。在这样的磷光材料中,红色磷光材料比荧光材料可以具有更大的发光效率。因此,作为提高有机电致发光器件的效率的重要因素,正在广泛研究红色磷光材料。
当使用这样的磷光材料时,需要高发光效率、高色纯度和延长的耐久性。最特别地,当使用红色磷光材料时,随色纯度增加(即CIE色度坐标的X值变得更大),可见度降低,从而导致难以提供高发光效率。因此,需要开发能提供优异的色度坐标(X的CIE色纯度=0.65以上)、提高的发光效率和延长的耐久性的红色磷光材料。
发明内容
用以解决所述问题的本发明的目的在于,提供红色磷光化合物和使用所述红色磷光化合物的有机电致发光器件,其基本消除了由于相关技术的限制和缺点而导致的一个或多个问题。
用以解决所述问题的本发明的另一目的在于,通过将式1所示的化合物结合入有机电致发光器件的发光层中作为掺杂剂,从而提供具有高色纯度、高亮度和长耐久性的有机电致发光器件。
通过提供下式1所示的红色磷光化合物可以达到本发明的目的。
式1
这里R1、R2、R3和R4各自独立地可以是取代或未取代的C1~C6烷基中的一个。C1~C6烷基中的每个可以选自甲基、乙基、正丙基、异丙基、正丁基、异丁基和叔丁基。
另外, 可以包括2,4-戊二酮 2,2,6,6-四甲基-3,5-庚二酮( )、1,3-丙二酮( )、1,3-丁二酮( )、3,5-庚二酮( )、1,1,1-三氟-2,4-戊二酮( )、1,1,1,5,5,5-六氟-2,4-戊二酮( )和2,2-二甲基-3,5-己二酮( )。
而且, 可以是下列化学式中的任一个:
并且,式1可以是下列化学式中的任一个:
在本发明的另一方面中,提供包括彼此顺次沉积的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极的有机电致发光器件,其中该有机电致发光器件可以使用上述式中的任一个作为发光层的掺杂剂。
这里,可以使用Al和Zn金属络合物和咔唑衍生物中的任一种作为发光层的主体材料,掺杂剂的使用量可以在0.1重量%~50重量%范围内。当使用的掺杂剂的量在上述范围内时,可以提供本发明的效率。并且,每种Al和Zn金属络合物的配体可以包括喹啉基、联苯基、异喹啉基、苯基、甲基喹啉基、二甲基喹啉基、二甲基异喹啉基,其中咔唑衍生物可以包括CBP。
附图说明
所包括的附图用以提供对本发明的进一步理解,附图例示了本发明的实施方案,与说明书一起起解释本发明原理的作用。
在附图中,
图1说明表示随有机电致发光器件的色纯度增加(即随色度坐标的X值变得更大)可见度降低的图。
图2说明在本发明实施方案中使用的化合物NPB、铜(II)酞菁(CuPc)、(bpt)2Ir(acac)、Alq3、BAlq和CBP的结构式。
具体实施方式
下文详细地参照本发明的优选实施方案,附图中解释了它们的例子。
下文描述形成根据本发明的红色磷光化合物的方法。在根据本发明的有机电致发光器件中使用红色磷光化合物中A-2所示的铱(III)(2-(3-甲基苯基)-7-甲基-喹啉并-N,C2)(2,4-戊二酮-O,O)化合物。
形成例
1.2-(3-甲基苯基)-6-甲基喹啉的形成
将3-甲基苯基硼酸(1.3mmol)、2-氯-6-甲基喹啉(1mmol)、四(三苯基膦)钯(0)(0.05mmol)和碳酸钾(3mmol)溶解在含有THF(30ml)和H2O(10ml)的两颈圆底烧瓶中。然后在100℃的浴池中搅拌该混合物24小时。随后,当不再发生反应时,废弃THF和甲苯。使用二氯甲烷和水萃取该混合物,然后用真空蒸馏处理。然后,在用 硅胶柱过滤该混合物之后,用真空蒸馏处理溶剂。此后,使用二氯甲烷和石油醚重结晶并过滤该混合物,从而生成固体2-(3-甲基苯基)-6-甲基喹啉。
2.氯交联的二聚体络合物的形成
将氯化铱(1mmol)和2-(3-甲基苯基)-6-甲基喹啉(2.5mmol)混合在2-乙氧基乙醇与蒸馏水的3∶1液体混合物(30ml)中。然后将该混合物回流24小时。此后,加入水从而将产生的固体形式进行过滤。随后,使用甲醇和石油醚洗涤该固体形式,从而生成氯交联的二聚体络合物。
3.铱(III)(2-(3-甲基苯基)-6-甲基-喹啉并-N,C2)(2,4-戊二酮-O,O)的形成
将氯交联的二聚体络合物(1mmol)、2,4-戊二酮(3mmol)和Na2CO3(6mmol)混合到2-乙氧基乙醇(30ml)中,回流24小时。然后在室温下将回流的混合物冷却。此后,将蒸馏水加到冷却的混合物中,过滤从而得到固体形式。随后,将固体形式溶解在二氯甲烷中,然后使用硅胶过滤。此后,用真空抽吸处理二氯甲烷,使用甲醇和石 油醚洗涤固体形式,以得到化合物。
此后给出优选实施方案的例子以描述本发明。显然应理解的是,本发明不仅仅局限于所提出的实施方案。
实施方案
1.第一实施方案
使ITO玻璃基板图案化以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。随后将该基板安放于真空室。标准压力设定为1×10-6托。此后,在ITO基板上以CuPc(200)、NPB(400 )、BAlq+A-2(7%)(200)、Alq3(300)、LiF(5)和Al(1000 )的顺序形成有机物质的层。
在0.9mA下,亮度等于1066cd/m2(6.5V)。此时,CIE x=0.646,y=0.351。并且,在2000cd/m2下,耐久性(初始亮度的一半)持续5500小时。
2.第二实施方案
使ITO玻璃基板图案化以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。随后将该基板安放于真空室。标准压力设定为1×10-6托。此后,在ITO基板上以CuPC(200)、NPB(400 )、BAlq+A-7(7%)(200)、Alq3(300)、LiF(5)和Al(1000 )的顺序形成有机物质的层。
在0.9mA下,亮度等于1102cd/m2(6.1V)。此时,CIEx=0.645,y=0.352。并且,在2000cd/m2下,耐久性(初始亮度的一半)持续5800小时。
3.第三实施方案
使ITO玻璃基板图案化以具有3mm×3mm的发光区域。然后, 洗涤图案化的ITO玻璃基板。随后将该基板安放于真空室。标准压力设定为1×10-6托。此后,在ITO基板上以CuPC(200)、NPB(400 )、BAlq+A-9(7%)(200)、Alq3(300)、LiF(5)和Al(1000 )的顺序形成有机物质的层。
在0.9mA下,亮度等于949cd/m2(5.3V)。此时,CIE x=0.658,y=0.339。并且,在2000cd/m2下,耐久性(初始亮度的一半)持续5000小时。
4.第四实施方案
使ITO玻璃基板图案化以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。随后将该基板安放于真空室。标准压力设定为1×10-6托。此后,在ITO基板上以CuPC(200)、NPB(400 )、CBP+A-2(7%)(200)、Alq3(300)、LiF(5)和Al(1000 )的顺序形成有机物质的层。
当使用BAlq形成空穴负载层时,在0.9mA下,亮度等于986cd/m2 (6.7V)。此时,CIE x=O.641,y=0.357。并且,在2000cd/m2下,耐久性(初始亮度的一半)持续4500小时。
对比例
使ITO玻璃基板图案化以具有3mm×3mm的发光区域。然后,洗涤图案化的ITO玻璃基板。随后将该基板安放于真空室。标准压力设定为1×10-6托。此后,在ITO基板上以CuPC(200)、NPB(400 )、BAlq+(btp)2Ir(acac)(7%)(200)、Alq3(300)、LiF(5)和Al(1000)的顺序形成有机物质的层。
在0.9mA下,亮度等于780cd/m2(7.5V)。此时,CIE x=0.659,y=0.329。并且,在2000cd/m2下,耐久性(初始亮度的一半)持续2500小时。
依据上述实施方案和对比例,效率、色度坐标、亮度和耐久性的特性显示在下表1中。
表1
器件 | 电压 (V) | 电流 (mA) | 亮度 (cd/m2) | 电流效率 (cd/A) | 功率效率 (1m/W) | CIE (X) | CIE (Y) | 耐久性(h) 初始亮度的 1/2 |
第一 实施方案 | 6.5 | 0.9 | 1066 | 10.66 | 5.2 | 0.65 | 0.34 | 5500 |
第二 实施方案 | 6.1 | 0.9 | 1102 | 11.02 | 5.7 | 0.65 | 0.35 | 5800 |
第三 实施方案 | 5.3 | 0.9 | 949 | 9.49 | 5.6 | 0.66 | 0.34 | 5000 |
第四 实施方案 | 6.7 | 0.9 | 986 | 9.86 | 4.6 | 0.64 | 0.36 | 4500 |
对比例 | 7.5 | 0.9 | 780 | 7.8 | 3.3 | 0.66 | 0.33 | 2500 |
如表1所示,当色纯度高(CIE(X)≥0.65)时,该器件在低电压下高效率地运行。并且,与对比例相比,第二实施方案的电流效率增加70%以上。另外,第二实施方案的耐久性增加到对比例的2倍。
下表2显示出根据本发明第二实施方案的有机电致发光器件中,随电压和电流的增加,效率、色度坐标和亮度的特性。
表2
电压 (V) | 电流(A(mA/cm2)) | 亮度(cd/m2) | 电流效率(cd/A) | 功率效率(1m/W) | CIE(X) | CIE(Y) |
4.58 | 1.111 | 131.8 | 11.86 | 8.14 | 0.65 | 0.35 |
5.10 | 3.333 | 458.2 | 13.75 | 8.47 | 0.65 | 0.35 |
5.49 | 6.666 | 958.6 | 14.38 | 8.22 | 0.65 | 0.35 |
6.07 | 16.666 | 2336 | 14.02 | 7.26 | 0.65 | 0.35 |
6.52 | 33.333 | 4424 | 13.27 | 6.39 | 0.65 | 0.35 |
7.01 | 88.888 | 10160 | 11.43 | 5.12 | 0.64 | 0.35 |
如表2所示,第二实施方案提供优异的效率,依据驱动电压的色度坐标也维持高的色纯度。
本领域的技术人员将明显看到,在不脱离本发明的精神和范围下本发明可以有许多修改和变化。因此可以预期,本发明覆盖在附带权利要求的范围及其相当范围内提供的本发明的修改和变化。
工业应用性
通过使用式1所示的化合物作为有机电致发光器件的发光层,本发明提供具有优异的色纯度和亮度以及延长的耐久性的有机电致发光器件。
Claims (7)
2.如权利要求1所述的红色磷光化合物,其中C1~C6烷基中的每个选自:甲基、乙基、正丙基、异丙基、正丁基、异丁基和叔丁基。
6.如权利要求5所述的有机电致发光器件,其中使用Al和Zn金属络合物和咔唑衍生物中的任一种作为发光层的主体材料。
7.如权利要求6所述的有机电致发光器件,其中每种Al和Zn金属络合物的配体选自喹啉基、联苯基、异喹啉基、苯基、甲基喹啉基、二甲基喹啉基、二甲基异喹啉基,且其中咔唑衍生物是CBP。
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Families Citing this family (95)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100803125B1 (ko) * | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
US8778508B2 (en) * | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
US8519130B2 (en) * | 2006-12-08 | 2013-08-27 | Universal Display Corporation | Method for synthesis of iriduim (III) complexes with sterically demanding ligands |
KR101634508B1 (ko) * | 2007-03-08 | 2016-06-28 | 유니버셜 디스플레이 코포레이션 | 인광성 물질 |
US9130177B2 (en) | 2011-01-13 | 2015-09-08 | Universal Display Corporation | 5-substituted 2 phenylquinoline complexes materials for light emitting diode |
KR101442826B1 (ko) * | 2007-03-30 | 2014-09-30 | 동우 화인켐 주식회사 | Kl 호스트 재료를 사용한 새로운 유기전계발광소자 및이를 구비한 표시장치 |
KR20090032250A (ko) * | 2007-09-27 | 2009-04-01 | 엘지디스플레이 주식회사 | 적색 인광 화합물 및 이를 이용한 유기 전계 발광 소자 |
US8956737B2 (en) | 2007-09-27 | 2015-02-17 | Lg Display Co., Ltd. | Red phosphorescent compound and organic electroluminescent device using the same |
KR101493218B1 (ko) * | 2007-10-23 | 2015-02-16 | 엘지디스플레이 주식회사 | 적색 인광 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR100923566B1 (ko) * | 2007-10-25 | 2009-10-27 | (주)그라쎌 | 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자 |
KR100933229B1 (ko) * | 2007-11-12 | 2009-12-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자 |
TWI482756B (zh) * | 2008-09-16 | 2015-05-01 | Universal Display Corp | 磷光物質 |
CN102203975B (zh) * | 2008-10-23 | 2014-04-30 | 通用显示公司 | 有机发光器件和用于其中的材料 |
KR101348698B1 (ko) * | 2008-10-29 | 2014-01-09 | 엘지디스플레이 주식회사 | 적색 인광 물질 및 이를 이용한 유기전계발광소자 |
JP5666111B2 (ja) * | 2009-08-31 | 2015-02-12 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子 |
US8941099B2 (en) | 2010-07-07 | 2015-01-27 | Universal Display Corporation | Organic light emitting device and materials for use in same |
US10008677B2 (en) | 2011-01-13 | 2018-06-26 | Universal Display Corporation | Materials for organic light emitting diode |
JP6014053B2 (ja) | 2011-02-11 | 2016-10-25 | ユニバーサル ディスプレイ コーポレイション | 有機発光素子及び該有機発光素子に使用されるための材料 |
WO2012108877A1 (en) | 2011-02-11 | 2012-08-16 | University Display Corporation | Organic light emitting device and materials for use in same |
JP2014511563A (ja) | 2011-02-11 | 2014-05-15 | ユニバーサル ディスプレイ コーポレイション | 有機発光素子及び該有機発光素子に使用されるための材料 |
KR20140043043A (ko) | 2011-02-11 | 2014-04-08 | 유니버셜 디스플레이 코포레이션 | 유기 발광 디바이스 및 이것에 사용되는 재료 |
US10199581B2 (en) | 2013-07-01 | 2019-02-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10749118B2 (en) | 2014-06-26 | 2020-08-18 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10361381B2 (en) | 2015-09-03 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180370999A1 (en) | 2017-06-23 | 2018-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20190161504A1 (en) | 2017-11-28 | 2019-05-30 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492480B1 (en) | 2017-11-29 | 2021-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3604321B1 (en) | 2018-07-31 | 2022-02-09 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound |
CN109053813A (zh) * | 2018-08-03 | 2018-12-21 | 瑞声科技(南京)有限公司 | 一种红光金属配合物、其制备方法及应用 |
US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
US20200251664A1 (en) | 2019-02-01 | 2020-08-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2020158491A (ja) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
US20210032278A1 (en) | 2019-07-30 | 2021-02-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN110590851A (zh) * | 2019-08-29 | 2019-12-20 | 浙江华显光电科技有限公司 | 红色磷光化合物和使用该化合物的有机电致发光器件 |
CN110746464A (zh) * | 2019-09-09 | 2020-02-04 | 浙江华显光电科技有限公司 | 红色磷光化合物和使用该化合物的有机电致发光器件 |
US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210217969A1 (en) | 2020-01-06 | 2021-07-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
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US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
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US6821645B2 (en) * | 1999-12-27 | 2004-11-23 | Fuji Photo Film Co., Ltd. | Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex |
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