CN103664746B - 蒽化合物以及包含该蒽化合物的有机发光二极管 - Google Patents

蒽化合物以及包含该蒽化合物的有机发光二极管 Download PDF

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CN103664746B
CN103664746B CN201210596401.9A CN201210596401A CN103664746B CN 103664746 B CN103664746 B CN 103664746B CN 201210596401 A CN201210596401 A CN 201210596401A CN 103664746 B CN103664746 B CN 103664746B
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金孝锡
徐正大
全银珠
金信韩
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LG Display Co Ltd
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Abstract

本发明公开了一种蒽化合物和包含该蒽化合物的有机发光二极管。有机发光二极管包括至少两个在第一电极和第二电极之间形成的叠层，以及在该叠层之间形成的包括N‑型CGL和P‑型CGL的电荷产生层(CGL)，其中N‑型CGL由蒽化合物形成。

Description

蒽化合物以及包含该蒽化合物的有机发光二极管
本申请要求于2012年9月3日提交的韩国专利申请10-2012-0097356号的权益，其在此引入作为参考用于所有目的，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(OLED)，更具体地，涉及一种包含蒽化合物的有机发光二极管(OLED)。
背景技术
最近，平板显示器(FPD)的重要性随着多媒体的发展而不断增加。因此，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(OLED)得以商业化。
特别是，OLED具有不超过1ms的高响应速度、消耗少量的能量、并且是自发光的。另外，因为对于视角不存在问题，OLED作为电影显示介质不论设备大小均具有优势。另外，因为OLED可以在低温下制造，并基于常规的半导体工艺技术具有简单的制造工艺，因此OLED作为下一代FPD而受到重视。
OLED包括阳极电极和阴极电极之间的发光层，使得由阳极电极提供的空穴和由阴极电极提供的电子在发光层中彼此结合形成激子，即空穴和电子的配对。通过激子回到基态产生能量发射出光。
OLED发展出了多种结构。其中，开发出了多个发光层层叠的串联型OLED。串联型OLED具有以下结构：在阳极电极和阴极电极之间层叠由多个各自由空穴注入层(HIL)/空穴传输层(HTL)/发光层/电子传输层(ETL)/电子注入层(EIL)形成的叠层。特别是，将由N-型CGL和P-型CGL形成的电荷产生层(CGL)设置在叠层之间从而产生电荷或将电荷注入到发光层中。
然而，在CGL中，由于N-型CGL和P-型CGL间存在能级差，将通过电荷产生在P-型CGL和邻近空穴注入层之间的界面上产生的电子注入到N-型CGL的特性是 不足的。另外，当常规的N-型CGL掺杂有碱金属时，碱金属会扩散到P-型CGL中导致OLED的寿命减少。
发明内容
本发明致力于提供一种蒽化合物以及包含该蒽化合物的有机发光二极管(OLED)，其中提供了一种新型N-型CGL从而降低了OLED的驱动电压，提高了OLED的发光效率，并且延长了OLED的寿命。
一方面，存在式1所示的蒽化合物，
[式1]
其中R1到R8各自为选自由具有1至20个碳原子的含氢烷基或杂烷基基团、具有5至20个碳原子的芳基基团、具有4至20个碳原子的含氮、硫、或氧的杂芳基基团组成的组中的一种，其中X9和X10各自为选自由具有4至20个碳原子的含氮、硫、或氧的杂芳基基团和具有6至20碳原子的芳基基团组成的组中的一种。
另一方面，有机发光二极管(OLED)包括至少两个在第一电极和第二电极间形成的叠层，以及在该叠层之间形成的包括N-型CGL和P-型CGL的电荷产生层(CGL)，其中N-型CGL由所述蒽化合物形成。
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是说明根据本发明实施方式的有机发光二极管(OLED)的图；
图2是说明根据本发明实施方式制造的OLED的电流密度随驱动电压的变化的 曲线图；以及
图3是说明根据本发明实施方式制造的OLED的寿命降低率随时间的变化的曲线图。
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，然而，本发明并不限于此。
参照图1，根据本发明实施方式的OLED100可以是包括黄光和蓝光的白色OLED。具体地，OLED100包括位于基底110上的第一电极120、位于第一电极120上并包括第一发光层133的第一叠层130、位于第一叠层130上的电荷产生层(CGL)140、位于CGL140上并包括第二发光层153的第二叠层150、和位于第二叠层150上的第二电极160。
基底110可以由透明玻璃、塑料或导电材料形成。作为用于注入空穴的阳极电极的第一电极120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)中的一种形成。可以在基底110和第一电极120之间进一步提供反射层115。在第一电极120下的用于向上反光的反射层115可以由Al、Ag和Ni中的一种形成。
位于第一电极120上的第一叠层130可以包括发蓝光的第一发光层133。在第一叠层130中，由于仅包含蓝光发射层作为第一发光层133，因此只有蓝光发出，可以改善蓝光的稳定性。在用于发射蓝光的第一发光层133中，可以将蓝色荧光掺杂剂与一种基质(host)混合。例如，在第一发光层133中，蓝色荧光掺杂剂如1，6-双(二苯胺)芘或TBPe(四(叔丁基)二萘嵌苯)可以与基质材料如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。此外，蓝色荧光掺杂剂可以是深蓝色掺杂剂或天蓝色掺杂剂。深蓝色掺杂剂可以是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。天蓝色掺杂剂可以是对-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131和第一空穴传输层132，和在第一发光层133和CGL140之间形成的第一电子传输层134。
用于从第一电极120向第一发光层133平稳注入空穴的空穴注入层131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形成，但是本发明不限于此。
用于平稳传输空穴的第一空穴传输层132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形成，但是本发明不限于此。
用于平稳传输电子的第一电子传输层134可以由选自由Alq3(三(8-羟基喹啉并)铝)、PDB、TAZ、螺-PBD、BAlq和SAlq组成的组的至少一种形成，但是本发明不限于此。
另一方面，位于第一叠层130上的CGL140为PN结CGL，其中N-型CGL141和P-型CGL142彼此相连。PN结CGL140产生电荷或将电荷分成空穴和电子，以将电荷注入到发光层。即，N-型CGL141将电子供应到与第一电极相邻的第一发光层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OLED的发光效率，并且可以降低OLED的驱动电压。
N-型CGL141由蒽化合物形成，将在之后详细介绍。P-型CGL142可以由掺杂有金属或P型掺杂剂的有机材料形成。这里，金属可以由选自Al、Cu、Fe、Pb、Zn、Au、Pt、W、In、Mo、Ni和Ti组成的组的一种或至少两种的合金形成。此外，用于掺杂有P型掺杂剂的有机材料的P型掺杂剂和基质可以由常规使用的材料形成。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。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。
另一方面，位于CGL140上的第二叠层150可以包括用于发射黄光的第二发光层153。在第二发光层153中，在基质中可以包含黄色掺杂剂或者在一种基质中可以 包含红色和绿色掺杂剂。
例如，当第二发光层153的基质中包含黄色掺杂剂时，与第一发光层133的前述基质相同的材料可以用作基质和蓝色掺杂剂且Irpq2acac(二(苯基喹啉)乙酰丙酮化铱)可以用作黄色磷光体掺杂剂。当第二发光层153的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)可以用作包含在基质中的红色磷光体掺杂剂，以及Irppy3(三(苯基吡啶)铱)可以用作绿色磷光体掺杂剂。
第二叠层150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152，以及形成于第二发光层153和第二电极160间的第二电子传输层154和电子注入层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相同，这里省略其说明。
用于稳定注入电子的电子注入层155可以由选自由Alq3(三(8-羟基喹啉并)铝)、PBD、TAZ、螺-PBD、BAlq或SAlq构成的组的至少一种形成，但是本发明不限于以上所述。此外，电子注入层155可以是金属卤化物，例如，选自由MgF2、LiF、NaF、KF、RbF、CsF、FrF和CaF2组成的组的至少一种，但是本发明不限于以上所述。
第二电极(阴极)160可以由透明材料形成，使得从发光层133和153发出的光可以发射到整个表面。例如，第二电极160可以是ITO、IZO和ZnO中的一种。
根据本发明的N-型CGL141由如式1所示的蒽化合物形成。
[式1]
在式1中，R1至R8各自为选自由具有1至20个碳原子的含氢烷基或杂烷基基团、具有5至20个碳原子的芳基基团、和具有4至20个碳原子的含氮、硫或氧的杂芳基基团组成的组中的一种，其中X9和X10各自为选自由具有4至20个碳原子的 含氮、硫或氧的杂芳基基团和具有6至20碳原子的芳基基团组成的组中的一种。
是选自由 组成的组中的一种。R6为选自由氢、组成的组中的一种。
例如，式1表示的蒽化合物可以通过与R6如表1所示的各种组合由以下化合物NC01至NC20形成：
[表1]
根据本发明的蒽化合物可以掺杂有碱金属。因此，如式2所示，由于蒽化合物的SP2-氮是具有相对丰富的电子的反应位点，SP2-氮与Li键合形成能隙状态。通过形成的能隙状态，电子可以容易地从P-型CGL传输到N-型CGL。
[式2]
因此，掺杂在传统N-型CGL上的碱金属会扩散到P-型CGL中以防止寿命减少并且容易传输电子。
下文中，将参考下述合成例和实施方式对用于本发明的N-型CGL的蒽化合物的合成例和包含该化合物的OLED进行详细描述。下述实施方式仅作为实施方式，本发明不限于以下实施方式。
合成例
1)2，6-二溴-9，10-二苯基蒽的合成
其中diethyl ether为二乙醚，acetic acid为乙酸。
在搅拌通过将2，6-二溴蒽醌(3g，8.2mmol)溶于乙醚(Et2O)得到的溶液的同时，缓慢滴加通过将苯基锂(2g，23.8mmol)溶于乙醚(Et2O)得到的溶液。此时，反应在干冰浴中进行。然后，当温度升至室温时，得到中间体。将通过过滤中间体得到的固体溶于60mL乙酸中。然后，将KI和NaH2PO2倒入通过将中间体溶解在乙酸中得到的溶液中。然后将溶液在130℃回流24小时。当反应完成时，加入水并进行过滤。然后将产生的固体物质用二氯甲烷和甲醇重结晶得到2，6-二溴-9，10-二苯基蒽(2.7g，5.5mmol，67％)。
2)NC05的制备
将吡啶硼酸(2.5g，20.3mmol)和60ml无水四氢呋喃倒入合成的2，6-二溴-9，10-二苯基蒽(3g，6.1mmol)中，将所得的溶液搅拌。加入四(三苯基膦)钯(1.4g，1.2mmol)、碳酸钾(K2CO3，6.3g，24.6mmol)以及60ml蒸馏水，将所得溶液在100℃回流24小时。反应完成时，移除四氢呋喃后，过滤所产生的固体物质。用二氯甲烷和甲醇重结晶该固体物质得到2，6-二吡啶-9，10-二苯基蒽，(NC05)(2.0g，4.1mmol，67％)。
3)NC10的制备
将喹啉硼酸(3.5g，20.2mmol)和60ml无水四氢呋喃倒入合成的2，6-二溴-9，10-二苯基蒽(3g，6.1mmol)中，将所得的溶液搅拌。加入四(三苯基膦)钯(1.4g，1.2mmol)、碳酸钾(K2CO3，6.3g，24.6mmol)以及60ml蒸馏水，将所得溶液在100℃回流24小时。反应完成时，移除四氢呋喃后，过滤所产生的固体物质。用二氯甲烷和甲醇重结晶该固体物质得到2，6-二喹啉-9，10-二苯基蒽，(NC010)(2.0g，4.3mmol，69％)。
在下文中，公开了其中使用前述合成例中制备的NC05和NC10所代表的蒽化合物作为N-型CGL来制备OLED的实施方式。
实施例1
将ITO玻璃图案化使得ITO玻璃的发射区域为2mm×2mm，然后清洗ITO玻璃。将基底置于真空室中后，使底压为1×10-6torr。然后将作为空穴注入层的NAT-CN沉积在作为阳极的ITO上，厚度为然后将10％以内的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(DNTPD)掺杂到4，4’-双[N-(1-萘基)-N-苯基氨基]-联苯基(NPD)作为空穴传输层，沉积厚度为然后，继续沉积TCTA至厚度为然后形成其中在ADN基体中包含叔丁基二萘嵌苯掺杂剂的发光层至的厚度。然后，形成作为电子传输层的Alq3至的厚度。然后，将碱金属Li掺杂在NC05所表示的材料上，使得形成的厚度的N-型CGL。形成作为P-型CGL的HAT-CN至的厚度。形成作为阳极的Al至约的厚度，从而制备出OLED。
<HAT-CN>
实施例2
在与上述实施例1相同的条件下，使用NC10所表示的化合物作为N-型CGL材料制造OLED。
对比实施例
在与上述实施例1相同的条件下，使用如下的Bphen材料作为N-型CGL材料制造OLED。
测量根据上述实施例1和2以及对比实施例制造的OLED的驱动电压、电流效率、量子效率、色坐标以及寿命以如下表2所示。另外，测量电流密度随驱动电压的变化以如图2所示，测量亮度减小率随时间的变化以如图3所示。
表2
如表1所示，可以看到根据本发明实施例1和2制造的OLED相比对比例具有更高的色坐标，而OLED的驱动电压、电流效率和量子效率具有明显的改进。尤其是参见图2，电流密度随驱动电压的变化得到改善，并且参见图3，寿命显著提高。
所以，本发明实施例的蒽化合物和含有该化合物的OLED相比于普通的OLED，在驱动电压、电流效率、量子效率、色坐标和寿命上都有改善。
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的精神和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 (7)

1.一种如式1所示的蒽化合物，
[式1]
其中R1、R3-R5、R7-R8各自为具有1至20个碳原子的含氢烷基；
其中R6为选自由
组成的组中的一种；
其中为选自由 组成的组中的一种；并且
其中X9和X10各自为具有6至20碳原子的芳基基团。
2.一种蒽化合物，其具有由如下的化学式表示的结构：
3.一种OLED，包括：
至少两个在第一电极和第二电极之间形成的叠层，以及
在该叠层之间形成的包括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或2所述的蒽化合物形成。
4.如权利要求3所述的OLED，其中每个叠层包括形成在所穿插的发光层一侧的空穴注入层和空穴传输层以及形成在另一侧的电子传输层。
5.如权利要求4所述的OLED，其中所述叠层中与第二电极相邻的叠层进一步包括电子注入层。
6.如权利要求4所述的OLED，其中所述叠层的发光层发出不同颜色的光成分。
7.如权利要求3所述的OLED，其中所述N-型电荷产生层掺杂有碱金属。
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Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015012044A (ja) * 2013-06-26 2015-01-19 株式会社東芝 半導体発光素子
KR102192001B1 (ko) 2014-03-31 2020-12-16 엘지디스플레이 주식회사 카바졸 화합물 및 이를 포함하는 유기발광소자
KR102302850B1 (ko) * 2014-10-22 2021-09-23 삼성디스플레이 주식회사 발광 소자
KR102253290B1 (ko) * 2014-11-07 2021-05-18 엘지디스플레이 주식회사 증착 감지 센서 및 그를 이용한 증착 속도 측정 장치와 박막 증착 장비
CN104466023B (zh) * 2014-12-24 2017-10-17 京东方科技集团股份有限公司 层叠式有机发光二极体及其制备方法和显示装置
KR102574052B1 (ko) 2015-11-19 2023-09-04 엘지디스플레이 주식회사 유기발광 표시장치
CN106784343B (zh) * 2015-11-19 2018-10-09 乐金显示有限公司 有机发光显示装置
KR102642369B1 (ko) * 2016-03-25 2024-03-05 삼성디스플레이 주식회사 유기 발광 표시 장치 및 유기 발광 표시 장치의 제조 방법
CN116583131A (zh) 2017-04-26 2023-08-11 Oti照明公司 用于图案化表面上覆层的方法和包括图案化覆层的装置
DE102017111137A1 (de) * 2017-05-22 2018-11-22 Novaled Gmbh Organische elektrolumineszente Vorrichtung
CN107394049A (zh) * 2017-07-06 2017-11-24 深圳市华星光电技术有限公司 一种白光oled器件
KR102027516B1 (ko) * 2017-12-22 2019-10-01 엘지디스플레이 주식회사 유기발광다이오드 및 이를 포함하는 유기발광 표시장치
US11751415B2 (en) 2018-02-02 2023-09-05 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
KR20200103235A (ko) * 2019-02-22 2020-09-02 삼성디스플레이 주식회사 유기 발광 소자
US11730012B2 (en) 2019-03-07 2023-08-15 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007130263A1 (en) * 2006-04-27 2007-11-15 Eastman Kodak Company Electroluminescent device including an anthracene derivative
CN101395105A (zh) * 2006-03-06 2009-03-25 Lg化学株式会社 新的蒽衍生物以及使用该衍生物的有机电子器件

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI314947B (en) * 2002-04-24 2009-09-21 Eastman Kodak Compan Organic light emitting diode devices with improved operational stability
US20070046189A1 (en) * 2005-08-31 2007-03-01 Eastman Kodak Company Intermediate connector for a tandem OLED device
US20070126347A1 (en) * 2005-12-01 2007-06-07 Eastman Kodak Company OLEDS with improved efficiency
US7638207B2 (en) * 2006-03-30 2009-12-29 Eastman Kodak Company OLED device with improved efficiency and lifetime
KR100903203B1 (ko) * 2006-11-30 2009-06-18 에스에프씨 주식회사 안트라센 유도체 및 이를 채용한 유기전계발광소자
KR100961781B1 (ko) * 2007-09-17 2010-06-07 에스에프씨 주식회사 ｎ형 유기반도체 화합물 및 이를 이용한 유기전계발광소자
US8367220B2 (en) * 2007-10-30 2013-02-05 Samsung Electronics Co., Ltd. Anthracene-based compound and organic light emitting device employing the same
JP2009123976A (ja) * 2007-11-16 2009-06-04 Toyo Ink Mfg Co Ltd 有機エレクトロルミネッセンス素子用材料および有機エレクトロルミネッセンス素子。
KR101068224B1 (ko) * 2008-02-05 2011-09-28 에스에프씨 주식회사 안트라센 유도체 및 이를 포함하는 유기전계발광소자

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101395105A (zh) * 2006-03-06 2009-03-25 Lg化学株式会社 新的蒽衍生物以及使用该衍生物的有机电子器件
WO2007130263A1 (en) * 2006-04-27 2007-11-15 Eastman Kodak Company Electroluminescent device including an anthracene derivative

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Pushing Fullerene Absorption into the Near-IR Region by Conjugately Fusing Oligothiophenes;Zuo Xiao，等;《Angewandte Chemie, International Edition》;20120809;第51卷(第36期);第9038-9041页 *

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