CN103664748B - 芘化合物以及包含该化合物的有机发光二极管设备 - Google Patents

芘化合物以及包含该化合物的有机发光二极管设备 Download PDF

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CN103664748B
CN103664748B CN201210595827.2A CN201210595827A CN103664748B CN 103664748 B CN103664748 B CN 103664748B CN 201210595827 A CN201210595827 A CN 201210595827A CN 103664748 B CN103664748 B CN 103664748B
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金信韩
徐正大
金孝锡
丁荣观
全银珠
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Abstract

本发明公开了一种芘化合物以及包含该化合物的有机发光二极管设备。有机发光二极管设备包括至少两个在第一电极和第二电极之间设置的叠层，以及在该叠层之间设置的包括N型电荷产生层和P型电荷产生层的电荷产生层，其中N型电荷产生层由所述芘化合物制成。

Description

芘化合物以及包含该化合物的有机发光二极管设备
本申请要求2012年9月3日提出的韩国专利申请10-2012-0097357的权益，其用于所有目的在此引入作为参考，如同在此完全阐明一样。
技术领域
本申请涉及一种有机发光二极管设备，更具体地，涉及一种包含芘化合物的有机发光二极管设备。
背景技术
近几年，随着多媒体的发展，平板显示器(FPD)的重要性不断增加。为了满足需求，各种显示器例如液晶显示器(LCD)、等离子体显示板(PDP)、场发射显示器(FED)、和有机发光二极管设备已经得到实际应用。
特别是，有机发光二极管设备是自发射设备，其表现出1ms或更少的高响应速度和低能量消耗。另外，因为有机发光二极管设备具有优良的视角，所以有机发光二极管设备作为电影画面显示介质不论设备的大小均具有优势。另外，因为有机发光二极管设备可以在低温下制造并且基于现有的半导体工艺技术其制造工艺简单，因此有机发光二极管设备作为下一代平板显示器引起广泛重视。
有机发光二极管设备包括阴极、阳极以及介于阴极和阳极之间的有机发光层。由阴极提供的电子和由阳极提供的空穴在发光层结合从而形成激子。通过激子从激发态过渡到基态，从而发射出光。
有机发光二极管设备已经开发出了多种结构。其中，已经开发出通过层叠多个发光层制成的串联型有机发光二极管设备。该有机发光二极管设备具有包括空穴注入层/空穴传输层/发光层/电子传输层/电子注入层的多个叠层结构。特别是，在叠层中形成包含N型和P型电荷产生层的电荷产生层，从而产生电荷或将电荷注入到各个发光层中。
然而，在电荷产生层中，由于在N型电荷产生层中的N型电荷产生层和P型电荷产生层之间的能级差，通过在邻近P型电荷产生层的空穴注入层的界面上的电荷产生而产生的电子的注入特性是不足的。当现有技术的N型电荷产生层掺杂有碱金属时，碱金属易扩散到P型电荷产生层中从而导致设备的使用寿命减少。
发明内容
本发明致力于提供一种芘化合物，其通过一种新型N型电荷产生层能够改进善量子效率和使用寿命，和提供包括该芘化合物的有机发光二极管设备。
一方面，存在下述化学式1所示的芘化合物：
[化学式1]
在化学式1中，A是选自C、N、S和O中的一种，B和R1是选自包含或不包含邻近的A的具有6至24个碳原子的杂芳基、具有取代基或不具有取代基的芳族芳基胺基团、或具有取代基或不具有取代基的杂芳族芳基胺基团中的一种基团，n为1至4的整数。另一方面，有机发光二极管设备包括至少两个在第一电极和第二电极之间设置的叠层，以及在所述叠层之间设置的包括N型电荷产生层和P型电荷产生层的电荷产生层，其中N型电荷产生层由芘化合物制成。
附图说明
包含附图以为本发明提供进一步的理解，引入附图并构成说明书的一部分，该附图说明了本发明的实施方式，并且与说明书一起用来解释本发明的原理。图中：
图1是说明根据本发明示例性实施方式的有机发光二极管设备的图；
图2是说明电流密度随根据本发明示例性实施方式制造的有机发光二极管设备的驱动电压变化的曲线图；以及
图3是显示使用寿命劣化率随根据本发明示例性实施方式制造的有机发光二极管设备的使用时间变化的曲线图。
具体实施方式
现在详细参考本发明的实施方式，其中的实例在下列附图中描述。只要可能，对于相同或相似部分在所有图中使用同样的附图标记。值得注意的是，如果已知技术确定不会误导本发明的实施方式，则已知技术的详细描述会被省略。
图1是说明根据本发明示例性实施方式的有机发光二极管设备的图。在下文中，以其中层叠两个叠层的有机发光二极管设备作为实例进行描述，然而，本发明并不限于此。
参考图1，根据本发明示例性实施方式的有机发光二极管设备100可以是具有黄光和蓝光的白色有机发光二极管设备。具体地，有机发光二极管设备100包括基底110上的第一电极120，布置在第一电极120上并包括第一发光层133的第一叠层130，布置在第一叠层130上的电荷产生层140，布置在电荷产生层140上并包括第二发光层153的第二叠层150，和布置在第二叠层150上的第二电极160。
基底110可以由透明玻璃和塑料材料、或导电材料制成。第一电极120是注射空穴的阳极电极并且可以是透射光的透明电极。第一电极120由铟锡氧化物(ITO)、铟锌氧化物(IZO)和氧化锌(ZnO)中的一种构成。有机发光二极管设备100可以在基底100和第一电极120之间包括的保护层115。保护层115向上反射光，并且可以在第一电极120的下部由铝(Al)、银(Ag)和镍(Ni)中的一种制成。
布置在第一电极120上的第一叠层130可以包括发射蓝光的第一发光层133。第一叠层130可以只包含蓝光发射层作为第一发光层133，并且发出蓝光以提升蓝光的色稳定性。第一发光层133是发射蓝光的发光层，并且可以将蓝色荧光掺杂剂与一种基质(host)混合。例如，通过将作为蓝色荧光掺杂剂的1，6-双(二苯胺)芘或TBPe(四(叔丁基)二萘嵌苯)与基质(host)材料例如AND(9，10-二(2-萘基)蒽)或DPVBi(4，4′-双(2，2-二苯基乙烯基-1-基)-联苯)混合可以形成第一发光层130。蓝色荧光掺杂剂可以是深蓝色掺杂剂或天蓝色掺杂剂。例如，深蓝色掺杂剂可以包括4′-N，N-二苯基氨基苯乙烯基-三联苯(DPA-TP)、2，5，2′，5′-四苯乙烯基-联苯(TSB)、或蒽的衍生物。
例如，天蓝色掺杂剂可以包括对-双(对-N，N-二苯基-氨基苯乙烯基)苯或苯基环戊二烯。
第一叠层130可以进一步包括在第一电极120和第一发光层133之间形成的第一空穴注入层(HIL)131，和在第一发光层133和电荷产生层140之间形成的第一电子传输层(ETL)134。
第一HIL131可以容易地将空穴从第一电极120注入到第一发光层133。第一HIL131可以由选自由酞菁铜(CuPc)、聚(3，4)-亚乙基二氧基噻吩(PEDOT)、聚苯胺(PANI)和N，N’-二萘基-N，N’-二苯基联苯胺(NPD)组成的组的至少一种制成，但是本发明并不限于此。
第一HTL132能容易地传输空穴。第一HTL132可以由选自由N，N’-二萘基-N，N’-二苯基联苯胺(NPD)、N，N’-双-(3-甲基苯基)-N，N’-双-(苯基)-联苯胺(TPD)、s-TAD、和4，4’，4”-三(N-3-甲基苯基-N-苯基-氨基)-三苯基胺(MTDATA)组成的组的至少一种制成，但是本发明不限于此。
第一电子传输层(ETL)能容易地传输电子。第一ETL134可以由选自由三(8-羟基喹啉并)铝(Alq3)、PBD、TAZ、螺-PBD、BAlq和SAlq组成的组的至少一种制成，但是本发明不限于此。
同时，布置在第一叠层130上的电荷产生层(CGL)140为PN结电荷产生层，其中在N型电荷产生层141和P型电荷产生层142之间形成结。PN结CGL140产生并将电荷注入到各发光层，或分别将空穴和电子注入到各发光层。即，N型CGL141将电子供应到与第一电极120相邻的第一发光层133，而P型CGL142将空穴供应到与第二电极160相邻的第二发光层153，从而可以提高包含多个发光层的有机发光二极管设备的发光效率，并且可以降低驱动电压。
N型CGL141由芘化合物制成，之后将对其进行详细说明。P型CGL142可以由金属或掺杂有P型掺杂剂的有机材料形成。这里，金属可以包括选自由Al、Cu、Fe、Pb、Zn、Au、Pt、W、In、Mo、Ni和Ti及其合金组成的组中的金属。用于掺杂有P型掺杂剂的有机材料的P型掺杂剂和基质材料可以使用通常使用的材料。例如，P-型掺杂剂可以是选自由2，3，5，6-四氟-7，7，8，8-四氰基对苯二醌二甲烷(F4-TCNQ)、四氰基对苯二醌二甲烷的衍生物、碘、FeCl3、FeF3和SbCl5构成的组中的一种材料。进一步，基质可以是选自由N，N’-二(萘-1-基)-N，N-二苯基-联苯胺(NPB)、N，N’-二苯基-N，N’-二(3-甲基苯基)-1，1-联苯基-4，4’-二胺(TPD)和N，N’，N’-四萘基-联苯胺(TNB)构成的组中的一种材料。
布置在CGL140上的第二叠层150可以包括发射黄光的第二发光层153。第二发光层153可以在基质中包含黄色掺杂剂，或在一种基质中包含红色和绿色掺杂剂。
例如，当第二发光层153在基质中包含黄色掺杂剂时，第二发光层153可以使用蓝色掺杂剂和与第一发光层133的基质同样的材料作为基质，并且可以使用Irpq2acac(二(苯基喹啉)乙酰丙酮化铱)。进一步地，当第二发光层153在一种基质中包含红色和绿色掺杂剂时，Ir(piq)2acac(二(苯基异喹啉)乙酰丙酮化铱)可以用在前述基质中作为红色磷光掺杂剂。Irppy3(三(苯基吡啶)铱)可以用作红色磷光掺杂剂。
第二叠层150可以进一步包括形成于CGL140和第二发光层153之间的第二空穴注入层151和第二空穴传输层153，以及第二电子传输层154和第二电子注入层(EIL)155。第二空穴注入层151、第二空穴传输层152和第二电子传输层154与前述的第一空穴注入层131、第一空穴传输层132和第一电子传输层134具有相同的功能，因此省略其说明。
EIL155能容易地注入电子，可以使用Alq3(三(8-羟基喹啉并)铝)、PBD、TAZ、螺-PBD、BAlq或SAlq，但是本发明不限于此。此外，EIL155可以由金属卤化物制成。例如，金属卤化物可以是选自由MgF2、LiF、NaF、KF、RbF、CsF、FrF和CaF2组成的组中的一种，但是本发明不限于此。
第二电极(阴极)160可以由透明材料制成，使得从发光层133和135发出的光可以输出到正面。例如，第二电极160可以由铟锡氧化物(ITO)、铟锌氧化物(IZO)和氧化锌(ZnO)中的一种制成。
本发明的N型CGL141可以由如以下化学式1所示的芘化合物制成。
[化学式1]
在化学式1中，A是选自C、N、S和O中的一种，B和R1是选自包含或不包含邻近的A的具有6至24个碳原子的杂芳基；具有取代基或不具有取代基的芳族芳基胺基团；或具有取代基或不具有取代基的杂芳族芳基胺基团中的一种基团，n为1至4的整数。
邻近B的含A的R1形成或不形成稠环。
化学式1为如下化学式2-8所示。
[化学式2]
[化学式3]
[化学式4]
[化学式5]
[化学式6]
[化学式7]
[化学式8]
在化学式2至8中，各取代基可以与邻近的取代基形成稠环。
化学式1表示的化合物以下述P1至P26的化合物表示。
化学式1中的至少一个取代基在芘的1、3、6和8位取代。
由于化学式1中芘的2位和6位容易取代，并且在从取代位的beta位存在π相互作用碳，与碳的π相互作用相关的轨道可用于与过渡金属相互作用。
具体地，参考如下化学式9，当锂(Li)掺杂有N型掺杂剂时，具有富电子的位点位于位置B，使得掺杂有N型掺杂剂的锂(Li)容易与成为具有相对缺电子的系统的锂相互作用，这能够产生更强的相互作用，同时形成化学上最稳定的六元环形状。这种情况下，位置A直接给电子或作为给予的连接体。
[化学式9]
在下文中，用于本发明的N型CGL的芘化合物的合成实施例以及包含该化合物的有机发光二极管设备将参考如下的合成实施例和实施方式进行描述。但是，下述实施方式仅作为实例说明，本发明不限于以下实施方式。
合成实施例
1)2，6-二溴-9-苯基-9H-咔唑(B)的合成
[反应式1]
R.T：室温
制备实施例：二溴芘的合成
将包含16g溴和100ml氯仿的第一溶液滴加到通过将10.0g(49.4mmol)芘溶解到250ml氯仿中获得的第二溶液中，同时在23℃的温度搅拌第二溶液7小时。在额外搅拌第二溶液一小时后，将得到的反应液体(包括结晶物)过滤从而得到结晶物。通过洗涤结晶物得到11.3g二溴芘，然后在减压下干燥经洗涤的结晶物(产率63％)气相色谱-质谱(GC-Mass)(理论值：283.16g/mol，测量值282g/mol)。
2)化合物A的制备：1，6-二(喹啉-3-基)芘(A)的合成
[反应式2]
将喹啉-3-硼酸(2.2g，12.2mmol)、三辛基甲基氯化铵(商品名：Aliquat366(下文中称作“Aliquat366”)，Aldrich公司制备，0.74g)、醋酸钯(1.3mg)、三(邻甲氧基苯基)膦(13.3mg)、甲苯(58ml)、以及碳酸钠水溶液(17.8mmol)加入到在制备实施例中合成的二溴芘(2.0g，5.6mmol)中，并且将他们在100℃的温度搅拌4小时。通过在室温下冷却所得反应液体并过滤冷却的反应液体(包括结晶物)得到结晶物。通过依次用甲苯、水和甲醇洗涤结晶物，并且减压干燥经洗涤的结晶物，得到1.2g化合物A(产率46％)。
GC-Mass(理论值：456.16g/mol，测量值：456g/mol)，1H-NMR(THF-d8，500MHz)(ppm)7.58(m，2H)，7.68～7.74(m，8H)，8.04～8.06(m，4H)，8.22(m，2H)，9.03(m，2H)
3)化合物B的制备：1，6-二(喹啉-8-基)芘(B)的合成
将喹啉-8-硼酸(2.2g，12.2mmol)、三辛基甲基氯化铵(商品名：Aliquat366(下文中称作“Aliquat366”)，Aldrich公司制备，0.74g)、醋酸钯(1.3mg)、三(邻甲氧基苯基)膦(13.3mg)、甲苯(58ml)、以及碳酸钠水溶液(17.8mmol)加入到在制备实施例中合成的二溴芘(2.0g，5.6mmol)中，并且将他们在100℃的温度搅拌4小时。通过在室温下冷却所得反应液体并过滤冷却的反应液体(包括结晶物)得到结晶物。通过依次用甲苯、水和甲醇洗涤结晶物，并且减压干燥经洗涤的结晶物，得到1.8g化合物B(产率48％)。
GC-Mass(理论值：456.16g/mol，测量值：456g/mol)，1H-NMR(THF-d8，500MHz)(ppm)7.49～7.71(m，10H)，7.83(m，2H)，8.00～8.06(m，6H)，8.81(m，2H)
4)化合物C的制备：1，6-二(1，10-邻二氮杂菲-5-基)芘(C)的合成
将1，10-菲-5-硼酸(2.2g，12.2mmol)、三辛基甲基氯化铵(商品名：Aliquat366(下文中称作“Aliquat366”)，Aldrich公司制备，0.74g)、醋酸钯(1.3mg)、三(邻甲氧基苯基)膦(13.3mg)、甲苯(58ml)、以及碳酸钠水溶液(17.8mmol)加入到在制备实施例中合成的二溴芘(2.0g，5.6mmol)中，并且将他们在100℃的温度搅拌4小时。通过在室温下冷却所得反应液体并过滤冷却的反应液体(包括结晶物)得到结晶物。通过依次用甲苯、水和甲醇洗涤结晶物，并且减压干燥经洗涤的结晶物，得到2.4g化合物C(产率77％)。
GC-Mass(理论值：558.63g/mol，测量值：558g/mol)，1H-NMR(THF-d8，500MHz)(ppm)7.26(m，2H)，7.55(m，2H)，7.71～7.77(m，6H)，8.00～8.06(m，8H)，8.80(m，4H)
对比例
在下文中，公开了使用前述合成实施例中制备的芘化合物作为N型CGL制造有机发光二极管设备的实施方式。
实施方式的层结构与下述对比例相同。区别在于N型CGL的基质材料是化合物A、B、C和B-phen(4，7-二苯基-1，10-邻二氮杂菲)。首先，以铟锡氧化物(ITO)为阳极材料，在透明基底上形成第一电极。在第一电极上形成具有10nm厚度的N，N’-二苯基-N，N’-双-[4-(苯基-间-甲苯基氨基)-苯基]-联苯基-4，4’-二胺以形成空穴注入层。在空穴注入层上沉积具有100nm厚度的NPD(4，4’-双[N-(1-萘基)-N-苯基氨基]-联苯基)(N，N’-二苯基N-萘基-N’-联苯基-1，1’-联苯基-4，4”-二胺)形成空穴传输层。在空穴传输层上形成具有厚度的发光层，其在以如下示例性分子1表示的荧光基质材料中包括蓝色荧光掺杂剂。通过沉积厚度为的Alq3在发光层上形成电子传输层，并且在电子传输层上形成CGL。这种情况下，CGL分成N型层和P型层两层。N型层通过以如下示例性分子2表示的B-phen(4，7-二苯基-1，10-邻二氮杂菲)与体积比为1％到50％的金属掺杂剂锂共沉积形成。P型层通过沉积厚度为的以如下示例性分子3表示的HAT-CN(二吡嗪并[2，3-f：2’，3’-h]喹喔啉-2，3，6，7，10，11-六甲腈)而形成。最后，通过使用保护金属例如Al在CGL上形成作为阴极的第二电极。
[示例性分子1]
[示例性分子2]
[示例性分子3]
实施例1
在与对比例相同的处理条件下，使用前述制备的化合物A替代示例性分子2表示的B-phen(4，7-二苯基-1，10-邻二氮杂菲)，形成N型CGL。
实施例2
在与对比例相同的处理条件下，使用前述制备的化合物B替代示例性分子2表示的B-phen(4，7-二苯基-1，10-邻二氮杂菲)，形成N型CGL。
实施例3
在与对比例相同的处理条件下，使用前述制备的化合物C替代示例性分子2表示的B-phen(4，7-二苯基-1，10-邻二氮杂菲)，形成N型CGL。
测量根据第一到第三实施方式以及对比例的有机发光二极管设备的驱动电压、电流效率、量子效率、色坐标以及使用寿命并列于下表1中。另外，测量电流密度随驱动电压的变化并如图2所示，测量亮度劣化率随时间的变化并如图3所示。
[表1]
如表1所列，可以看到根据本发明第一到第三实施方式制造的有机发光二极管设备能够显著提高量子效率，同时显示与对比例相同的色坐标。尤其是参见图2，电流密度随驱动电压而增加，并且由图3所示，使用寿命特性显著提高。
所以，本发明实施方式的芘化合物和含有该化合物的有机发光二极管设备相比于现有技术的有机发光二极管设备，可以改善量子效率和使用寿命特性。
虽然参考许多说明性实施方式对实施方式进行了说明，可以理解的是本领域技术人员可以提出落入本文原理范围内的许多其他修改和实施方式。尤其是，在本文、附图和附上的权利要求范围内，主题联合布置的部件和/或布置的各种的变化和修改是可能的。除部件和/或布置的变化和修改外，可选的用途对于本领域技术人员同样是明显的。

Claims (6)

1.一种芘化合物，所述芘化合物如下述P18、P20和P21的化合物所示，
2.一种有机发光二极管设备，包括：
至少两个在第一电极和第二电极之间设置的叠层；以及
在所述叠层之间设置的包括N型电荷产生层和P型电荷产生层的电荷产生层，
其中所述N型电荷产生层由根据权利要求1所述的芘化合物制成。
3.如权利要求2所述的有机发光二极管设备，其中每个叠层包括在叠层的一面形成的空穴注入层和空穴传输层和在叠层的另一面形成的电子传输层，同时将发光层穿插于其间。
4.如权利要求2所述的有机发光二极管设备，其中所述叠层中与第二电极相邻的叠层中进一步包括电子注入层。
5.如权利要求2所述的有机发光二极管设备，其中所述叠层的发光层各自发出不同颜色的光。
6.如权利要求2所述的有机发光二极管设备，其中N型电荷产生层掺杂有碱金属。
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EP2983221B1 (en) * 2014-08-07 2020-10-07 OLEDWorks GmbH Light emitting device
KR20160029962A (ko) * 2014-09-05 2016-03-16 에스케이케미칼주식회사 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자
JPWO2016047661A1 (ja) * 2014-09-26 2017-07-27 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子
KR102291896B1 (ko) * 2014-10-13 2021-08-20 엘지디스플레이 주식회사 전하생성 화합물 및 이를 포함하는 유기전계발광소자
CN104393185B (zh) * 2014-11-25 2017-05-24 京东方科技集团股份有限公司 一种叠层有机电致发光器件及其制作方法
KR102354847B1 (ko) * 2014-12-16 2022-01-24 엘지디스플레이 주식회사 유기발광 표시장치
KR102242795B1 (ko) * 2014-12-26 2021-04-21 엘지디스플레이 주식회사 유기 발광 소자와 그 제조 방법 및 그를 이용한 유기 발광 디스플레이 장치
CN104795432A (zh) * 2015-05-04 2015-07-22 京东方科技集团股份有限公司 一种有机发光二极管器件及显示装置
CN104966789A (zh) * 2015-06-30 2015-10-07 深圳市华星光电技术有限公司 一种电荷连接层及其制造方法、叠层oled器件
KR102323243B1 (ko) * 2015-07-22 2021-11-08 삼성디스플레이 주식회사 유기 발광 소자 및 이를 포함하는 유기 발광 표시 장치
KR102388253B1 (ko) * 2015-11-06 2022-04-20 삼성디스플레이 주식회사 유기 발광 소자
CN105355798A (zh) * 2015-11-25 2016-02-24 京东方科技集团股份有限公司 有机电致发光器件及其制作方法、显示装置
KR102469217B1 (ko) * 2015-11-27 2022-11-21 엘지디스플레이 주식회사 유기전계발광소자
CN105679955A (zh) 2016-01-25 2016-06-15 深圳市华星光电技术有限公司 量子点发光器件及其制备方法及液晶显示装置
CN105679956A (zh) * 2016-04-05 2016-06-15 深圳市华星光电技术有限公司 有机电致发光器件及显示装置
KR102616579B1 (ko) * 2016-04-08 2023-12-22 삼성디스플레이 주식회사 유기 발광 소자
CN106058066B (zh) * 2016-08-12 2018-09-07 京东方科技集团股份有限公司 有机电致发光器件及其制备方法、显示装置
KR101926768B1 (ko) 2016-12-08 2018-12-07 주식회사 진웅산업 벤조나프티리딘 화합물 및 이를 포함하는 유기발광소자
KR101954364B1 (ko) 2016-12-08 2019-03-05 주식회사 진웅산업 카바졸 화합물 및 이를 포함하는 유기발광소자
KR102157756B1 (ko) * 2016-12-12 2020-09-18 엘지디스플레이 주식회사 유기 화합물과 이를 포함하는 유기발광다이오드 및 유기발광 표시장치
KR101954365B1 (ko) 2016-12-14 2019-03-05 주식회사 진웅산업 인다졸 화합물 및 이를 포함하는 유기발광소자
KR101954366B1 (ko) 2016-12-23 2019-03-05 주식회사 진웅산업 피리미딘 화합물 및 이를 포함하는 유기발광소자
CN107068883A (zh) * 2017-03-27 2017-08-18 深圳市华星光电技术有限公司 一种oled显示器件及其制备方法
KR102126552B1 (ko) 2017-12-19 2020-06-24 엘지디스플레이 주식회사 표시 장치
KR102027512B1 (ko) * 2017-12-22 2019-10-01 엘지디스플레이 주식회사 유기발광다이오드 및 이를 포함하는 유기발광 표시장치
CN108461638B (zh) * 2018-02-27 2020-06-23 上海天马有机发光显示技术有限公司 一种有机电致发光器件、其制备方法及显示装置
KR20200064423A (ko) 2018-11-29 2020-06-08 주식회사 진웅산업 파이렌 화합물 및 이를 포함하는 유기발광소자
KR101990049B1 (ko) 2018-12-06 2019-06-18 주식회사 진웅산업 페난스롤린 화합물 및 이를 포함하는 유기발광소자
CN109585668B (zh) * 2019-01-10 2021-01-29 京东方科技集团股份有限公司 Oled显示器件、显示面板、oled显示器件的制备方法
KR20210008979A (ko) * 2019-07-15 2021-01-26 삼성디스플레이 주식회사 화합물 및 이를 포함하는 유기 발광 소자
JP2019216290A (ja) * 2019-10-01 2019-12-19 パイオニア株式会社 発光装置
CN112993199B (zh) * 2021-02-25 2023-03-07 上海弗屈尔光电科技有限公司 一种三元组合物及含有该组合物的有机发光元件与应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101003508A (zh) * 2006-01-16 2007-07-25 Lg电子株式会社 电子传输化合物和包含该化合物的有机发光器件
CN101258221A (zh) * 2005-09-08 2008-09-03 东丽株式会社 发光元件材料和发光元件
US20080269491A1 (en) * 2007-02-13 2008-10-30 Arizona Board Of Regents For And On Behalf Of Arizona State University Organometallic Materials for Optical Emission, Optical Absorption, and Devices Including Organometallic Materials
CN101550234A (zh) * 2009-05-13 2009-10-07 中国科学院上海微系统与信息技术研究所 对苯胺类化合物有传感功能的荧光传感材料、方法及应用
CN103178212A (zh) * 2011-12-26 2013-06-26 三星显示有限公司 具有提高的使用寿命的有机发光装置

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0750331B2 (ja) * 1989-01-20 1995-05-31 キヤノン株式会社 電子写真感光体
US7651788B2 (en) * 2003-03-05 2010-01-26 Lg Display Co., Ltd. Organic electroluminescent device
KR101192519B1 (ko) * 2004-05-12 2012-10-17 이데미쓰 고산 가부시키가이샤 방향족 아민 유도체, 이를 이용한 유기 전기 발광 소자 및방향족 아민 유도체의 제조방법
JP2006176491A (ja) * 2004-11-25 2006-07-06 Kyoto Univ ピレン系化合物及びこれを用いた発光トランジスタ素子
JP2006176494A (ja) * 2004-11-25 2006-07-06 Kyoto Univ ピレン系化合物及びこれを用いた発光トランジスタ素子及びエレクトロルミネッセンス素子
JP2007131723A (ja) * 2005-11-10 2007-05-31 Toray Ind Inc 発光素子材料および発光素子
US7811681B2 (en) * 2006-01-16 2010-10-12 Lg Display Co., Ltd. Electron transport compound and organic light emitting device comprising the same
JP2010123917A (ja) * 2008-10-22 2010-06-03 Canon Inc 有機発光素子
KR20100070979A (ko) * 2008-12-18 2010-06-28 동우 화인켐 주식회사 비대칭 구조의 유기전기발광소자용 아릴아민유도체, 그 제조방법, 이를 포함하는 유기전기발광소자용 유기박막재료 및 이를 이용한 유기 전기발광소자
KR101616691B1 (ko) * 2009-09-09 2016-05-02 에스에프씨 주식회사 유기전계발광소자
KR101160670B1 (ko) * 2009-12-07 2012-06-28 (주)씨에스엘쏠라 유기발광화합물 및 이를 구비한 유기발광소자
KR101365824B1 (ko) * 2010-10-22 2014-02-20 엘지디스플레이 주식회사 유기전계발광소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101258221A (zh) * 2005-09-08 2008-09-03 东丽株式会社 发光元件材料和发光元件
CN101003508A (zh) * 2006-01-16 2007-07-25 Lg电子株式会社 电子传输化合物和包含该化合物的有机发光器件
US20080269491A1 (en) * 2007-02-13 2008-10-30 Arizona Board Of Regents For And On Behalf Of Arizona State University Organometallic Materials for Optical Emission, Optical Absorption, and Devices Including Organometallic Materials
CN101550234A (zh) * 2009-05-13 2009-10-07 中国科学院上海微系统与信息技术研究所 对苯胺类化合物有传感功能的荧光传感材料、方法及应用
CN103178212A (zh) * 2011-12-26 2013-06-26 三星显示有限公司 具有提高的使用寿命的有机发光装置

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Cyclometalated Complexes of Ru(II) with 2-Aryl Derivatives of Quinoline and 1,10-Phenanthroline;Celine Bonnefous等;《Inorg. Chem.》;20011006;第40卷(第23期);第5851页右栏、第5852页左栏 *
Excited State Processes in Ruthenium(II)/Pyrenyl Complexes Displaying Extended Lifetimes;Daniel S. Tyson等;《J. Phys. Chem. A》;20010802;第105卷(第35期);第8154页右栏第2段第3-4行 *

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