CN106716665B - 有机电致发光器件 - Google Patents

有机电致发光器件 Download PDF

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CN106716665B
CN106716665B CN201580051461.4A CN201580051461A CN106716665B CN 106716665 B CN106716665 B CN 106716665B CN 201580051461 A CN201580051461 A CN 201580051461A CN 106716665 B CN106716665 B CN 106716665B
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electron transport
transport material
electroluminescence device
organic
organic electroluminescence
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CN106716665B9 (zh
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张焚在
张俊起
金性昭
李东勋
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LG Corp
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Abstract

本说明书的一个示例性实施方案提供了一种有机电致发光器件,其包括:阳极、阴极、设置在所述阳极和所述阴极之间的发光层,以及设置在所述阴极和所述发光层之间的电子传输层,其中所述电子传输层包含第一电子传输材料和第二电子传输材料,所述第一电子传输材料为包含单环或多环的有机材料,所述单环或多环包含含N六元环,所述第二电子传输材料为包含五元杂环或氰基的有机材料,所述五元杂环包含N、O和S中的至少一个杂原子,并且所述第二电子传输材料的偶极矩大于所述第一电子传输材料的偶极矩。

Description

有机电致发光器件
技术领域
本说明书要求于2014年10月27日在韩国知识产权局提交的韩国专利申请No.10-2014-0146402的优先权和权益,其全部内容通过引用并入本文。
本说明书涉及有机电致发光元件。
背景技术
有机电致发光器件是通过施加的电压经由电流发光的电子元件。Tang等在论文[Applied Physics Letters 51,p.913,1987]中报道了一种具有良好特性的有机电致发光器件。此外,还开发了使用聚合物材料,同时使用在该论文中公开的有机电致发光器件的结构的有机电致发光器件。
如上所述的相关技术的关键点是使不同的有机材料层分担用于进行有机电致发光器件发光的过程,即电荷注入、电荷传输、光激子形成和光产生的作用。因此,近年来,已经使用了具有细分为更多层的结构的有机电致发光器件。
同时,多种元件制造结构用于电子注入和传输层中,以便使电子从第二电极平稳地移动到发光层。
例如,属于碱金属族的金属化合物如LiF、NaF和LiQ经常用作用于电子注入层的材料,并且当电子移动时基本上具有稳定结构的有机材料经常用于电子传输层。为了实现更好的元件效率,作为用于电子传输层的材料,具有比发光层的激子能量更大的带隙和深HOMO能级以阻挡空穴从发光层溢出的材料经常用作用于电子传输层的材料。
为了改善电子传输层的电子注入特点,属于碱金属族的金属和金属化合物如Li、Ca、LiF和LiQ也可与用于电子传输层的材料一起使用以形成层。
吡啶、嘧啶或三嗪的有机材料。
根据本说明书的又一示例性实施方案,所述第二电子传输材料为包含五元杂环或氰基的有机材料,所述五元杂环包含N、O和S中的至少一个杂原子。所述第二电子传输材料不包含六元杂环。
根据本说明书的另一示例性实施方案,所述第二电子传输材料为包含咪唑、唑或噻唑的有机材料。
根据本说明书的又一示例性实施方案,所述第二电子传输材料为包含苯并咪唑、苯并唑或苯并噻唑的有机材料。
根据本说明书的另一示例性实施方案,所述第一电子传输材料和所述第二电子传输材料不包含金属单质。
根据本说明书的又一示例性实施方案,所述第一电子传输材料和所述第二电子传输材料为有机材料。所述第一电子传输材料和所述第二电子传输材料不包含金属络合物。
根据本说明书的另一示例性实施方案,所述第一电子传输材料和所述第二电子传输材料的分子量各自为400Da至900Da。
根据本说明书的又一示例性实施方案,所述电子传输层与所述阴极之间还包括电子传输层。
有益效果
根据本说明书中描述的示例性实施例,可提供具有高效率和/或长使用寿命特性的有机电致发光器件以及简单制造方法。
具体实施方式
下文中,将详细描述本说明书。
本说明书提供了一种有机电致发光器件,其包括:阳极、阴极、设置在所述阳极和所述阴极之间的发光层,以及设置在所述阴极和所述发光层之间的电子传输层,其中所述电子传输层包含第一电子传输材料和第二电子传输材料,所述第一电子传输材料为包含单环或多环的有机材料,所述单环或多环包含含N六元环,所述第二电子传输材料为包含五元杂环或氰基的有机材料,所述五元杂环包含N、O和S中的至少一个杂原子,并且所述第二电子传输材料的偶极矩大于所述第一电子传输材料的偶极矩。
在本说明书中当一个部件“包括”一个构成元件时,除非另有具体描述,否则这并不意味着排除另一个构成元件,而是指还可以包括另一个构成元件。
在根据本说明书的一个示例性实施方案的有机电致发光器件中,通过在阴极与发光层之间形成包含两种电子传输材料(其由第一电子传输材料和第二电子传输材料构成)的电子传输层的简单制造方法,可以提供具有长使用寿命与改善的使用寿命特性的元件。
根据本说明书的一个示例性实施方案,第一电子传输材料和第二电子传输材料是有机材料。具体地,所述第一电子传输材料为包含单环或多环的有机材料,所述单环或多环包含含N六元环,并且所述第二电子传输材料为包含五元杂环或氰基的有机材料,所述五元杂环包含N、O和S中的至少一个杂原子。
在本说明书的一个示例性实施方案中,第一电子传输材料和第二电子传输材料基本上不包含金属单质或金属络合物。因此,可以防止金属单质或金属络合物缩短元件的使用寿命的问题。
根据一个示例性实施方案,在电子传输层中可以以1:99至99:1的体积比使用第一电子传输材料和第二电子传输材料。
根据一个示例性实施方案,在电子传输层中可以以1:9至9:1的体积比使用第一电子传输材料和第二电子传输材料。例如,在电子传输层中可以以1:9、2:8、3:7、4:6、5:5、6:4、7:3、8:2或9:1的体积比使用第一电子传输材料和第二电子传输材料。
根据一个示例性实施方案,在电子传输层中可以以1:9至5:5的体积比使用第一电子传输材料和第二电子传输材料。
根据本说明书的一个示例性实施方案的第二电子传输材料在电子注入和/或电子传输特性方面比第一电子输送材料相对更好。然而,即使电子注入和电子传输特性是优异的,但是当达到空穴与电子之间的平衡,即电子和空穴之比接近1时,可以增加激子的产生,从而最大化元件的效率特性。
因此,为了使激子的产生最大化,需要调节传输到发光层的电子的量,并且所述电子的量可以通过调节上述第一电子传输材料与第二电子传输材料之比来调节。因此,当获得根据本说明书的一个示例性实施方案的第一电子传输材料与第二电子传输材料的体积比时,可以通过适当地调节从电子传输层转移到发光层的电子的量来期望元件的高发光效率。
根据本说明书的另一示例性实施方案,有机电致发光器件还包括设置在电子传输层和阴极之间的电子注入层。
本说明书的有机电致发光器件还可以在阳极和发光层之间包括一个或更多个有机材料层。
本说明书的有机电致发光器件还可以在发光层和电子传输层和/或电子传输层和阴极之间包括一个或更多个有机材料层。
例如,本说明书的有机电致发光器件可以具有包括作为有机材料层的空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等的结构。然而,有机电致发光器件的结构不限于此,并且可以包括更少数量的有机层。
在另一个示例性实施方案中,有机电致发光器件可以是具有常规型结构的有机电致发光器件,其中阳极、有机材料层和阴极按顺序堆叠在基底。

Claims (10)

1.一种有机电致发光器件,包括:
阳极;
阴极;
设置在所述阳极和所述阴极之间的发光层;以及
设置在所述阴极和所述发光层之间的电子传输层,
其中所述电子传输层包含第一电子传输材料和第二电子传输材料,
所述第一电子传输材料为包含单环或多环的有机材料,所述单环或多环包含含N六元环,
所述第二电子传输材料为包含五元杂环或氰基的有机材料,所述五元杂环包含N、O和S中的至少一个杂原子,并且
所述第二电子传输材料的偶极矩大于所述第一电子传输材料的偶极矩,
其中所述第一电子传输材料和所述第二电子传输材料不包含金属单质或金属络合物,
其中所述第一电子传输材料的偶极矩为0德拜至3德拜,并且所述第二电子传输材料的偶极矩为1德拜至7德拜。
2.根据权利要求1所述的有机电致发光器件,其中所述第一电子传输材料包含由下式1表示的结构:
[式1]
在所述式1中,
X1至X6中的一个至三个为N,
其他为CR1,且R1为一价有机基团,并且
相邻的一价有机基团任选地彼此结合形成经取代或未经取代的脂肪族环或者经取代或未经取代的芳香族环。
3.根据权利要求1所述的有机电致发光器件,其中所述第一电子传输材料为包含吡啶、嘧啶或三嗪的有机材料。
4.根据权利要求1所述的有机电致发光器件,其中所述第二电子传输材料包含由下式5表示的结构:
[式5]
在所述式5中,
Y1为NR21、O或S,
Y2至Y5彼此相同或不同,且各自为N或CR22
R21和R22彼此相同或不同,且各自为一价有机基团,并且
相邻的一价有机基团任选地彼此结合形成经取代或未经取代的脂肪族环或者经取代或未经取代的芳香族环。
5.根据权利要求1所述的有机电致发光器件,其中所述第二电子传输材料为包含咪唑、唑或噻唑的有机材料。
6.根据权利要求1所述的有机电致发光器件,其中所述第二电子传输材料为包含苯并咪唑、苯并唑或苯并噻唑的有机材料。
7.根据权利要求1所述的有机电致发光器件,其中所述第二电子传输材料包含由下式14表示的结构:
[式14]
CN-(L31)t-R31
在式14中,
L31为二价有机基团,且t为0至4的整数,且当t为2或更大时,L31彼此相同或不同,并且
R31为一价有机基团。
8.根据权利要求1所述的有机电致发光器件,其中所述第一电子传输材料和所述第二电子传输材料的分子量各自为400Da至900Da。
9.根据权利要求1所述的有机电致发光器件,其中包含所述第一电子传输材料和所述第二电子传输材料的所述电子传输层包含体积比为1:99至99:1的所述第一电子传输材料和所述第二电子传输材料。
10.根据权利要求1所述的有机电致发光器件,还包括:
设置在所述电子传输层和所述阴极之间的电子注入层。
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Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8803420B2 (en) 2010-01-15 2014-08-12 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
EP2545964A1 (en) 2011-07-13 2013-01-16 Phenex Pharmaceuticals AG Novel FXR (NR1H4) binding and activity modulating compounds
KR101560102B1 (ko) * 2014-11-20 2015-10-13 주식회사 엘지화학 유기 발광 소자
KR101924108B1 (ko) 2015-12-23 2018-11-30 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자
CN105399696B (zh) * 2015-12-25 2019-12-24 上海天马有机发光显示技术有限公司 有机电致发光化合物及其有机光电装置
JP6659067B2 (ja) * 2016-02-18 2020-03-04 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器
CA2968836A1 (en) 2016-06-13 2017-12-13 Gilead Sciences, Inc. Fxr (nr1h4) modulating compounds
EP3730487B1 (en) 2016-06-13 2022-04-27 Gilead Sciences, Inc. Azetidine derivatives as fxr (nr1h4) modulators
WO2018070840A1 (ko) * 2016-10-14 2018-04-19 주식회사 엘지화학 유기전계 발광 소자
KR102044427B1 (ko) * 2016-12-14 2019-11-14 주식회사 엘지화학 유기 발광 소자
CN108218802B (zh) * 2016-12-14 2021-08-10 株式会社Lg化学 有机发光元件
KR102145024B1 (ko) * 2016-12-20 2020-08-14 주식회사 엘지화학 유기 발광 소자
EP3343203B1 (en) 2016-12-28 2019-11-13 Vito NV Optical methods for phase change materials
KR102454951B1 (ko) * 2017-01-16 2022-10-17 삼성전자주식회사 유기 발광 소자
WO2018139662A1 (ja) * 2017-01-30 2018-08-02 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器
KR20190126920A (ko) 2017-03-28 2019-11-12 길리애드 사이언시즈, 인코포레이티드 간 질환을 치료하기 위한 치료 조합물
JP6794607B2 (ja) 2017-03-30 2020-12-02 エルジー・ケム・リミテッド 有機発光素子
CN107805248A (zh) * 2017-11-01 2018-03-16 长春海谱润斯科技有限公司 一种含有苯并咪唑结构的衍生物及其制备方法和有机电致发光器件
KR102478677B1 (ko) * 2017-12-29 2022-12-16 엘지디스플레이 주식회사 유기 발광 소자 및 이를 이용한 유기 발광 표시 장치
CN111247650B (zh) * 2018-02-02 2023-11-07 株式会社Lg化学 有机发光二极管
CN111712938A (zh) * 2018-02-20 2020-09-25 出光兴产株式会社 有机电致发光元件和电子设备
KR101966306B1 (ko) * 2018-06-18 2019-04-05 주식회사 엘지화학 유기 발광 소자
CN108963098B (zh) * 2018-08-03 2020-04-28 京东方科技集团股份有限公司 一种qled显示面板及其制备方法、显示装置
KR102216771B1 (ko) * 2018-09-03 2021-02-17 주식회사 엘지화학 유기 발광 소자
CN112236879A (zh) * 2018-09-03 2021-01-15 株式会社Lg化学 有机发光器件
JP2022017601A (ja) * 2018-09-07 2022-01-26 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器
KR102225970B1 (ko) * 2018-09-17 2021-03-10 주식회사 엘지화학 유기 발광 소자
EA202191566A1 (ru) 2019-01-15 2021-11-01 Джилид Сайенсиз, Инк. Соединения, модулирующие fxr (nr1h4)
KR20200093442A (ko) 2019-01-28 2020-08-05 주식회사 엘지화학 유기 발광 소자
CA3129949C (en) 2019-02-19 2024-04-30 Gilead Sciences, Inc. Solid forms of fxr agonists
KR102349278B1 (ko) 2019-09-03 2022-01-11 삼성디스플레이 주식회사 유기 발광 소자
CN112225706B (zh) * 2019-12-31 2022-05-03 陕西莱特光电材料股份有限公司 有机化合物、使用其的电子器件及电子装置
EP3923363A1 (en) * 2020-06-12 2021-12-15 Novaled GmbH Organic light emitting diode and device comprising the same
KR20220134125A (ko) * 2021-03-26 2022-10-05 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101101975A (zh) * 2006-07-04 2008-01-09 株式会社半导体能源研究所 发光元件、发光装置和电子装置

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2004057926A1 (ja) 2002-12-19 2006-04-27 株式会社半導体エネルギー研究所 有機発光素子、有機発光素子を用いた発光装置、及び前記発光装置を用いた電気器具
CN101812021B (zh) * 2003-03-13 2012-12-26 出光兴产株式会社 含氮杂环衍生物及使用该衍生物的有机电致发光元件
US7517595B2 (en) 2005-03-10 2009-04-14 Eastman Kodak Company Electroluminescent devices with mixed electron transport materials
US20060246315A1 (en) * 2005-04-27 2006-11-02 Begley William J Phosphorescent oled with mixed electron transport materials
WO2010076878A1 (ja) * 2009-01-05 2010-07-08 出光興産株式会社 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
JP5438757B2 (ja) * 2009-04-01 2014-03-12 出光興産株式会社 有機エレクトロルミネッセンス素子
JP5109054B2 (ja) * 2009-04-17 2012-12-26 株式会社デンソー 有機電界発光素子
JP5586254B2 (ja) * 2009-09-01 2014-09-10 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、有機電界発光素子の製造方法、表示装置及び照明装置
WO2011122132A1 (ja) * 2010-03-31 2011-10-06 出光興産株式会社 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
WO2011148909A1 (ja) * 2010-05-24 2011-12-01 出光興産株式会社 有機エレクトロルミネッセンス素子
EP2602839A1 (en) 2010-08-05 2013-06-12 Idemitsu Kosan Co., Ltd. Organic electroluminescent element
TW201232864A (en) * 2010-11-22 2012-08-01 Idemitsu Kosan Co Organic electroluminescence device
JP5938175B2 (ja) * 2011-07-15 2016-06-22 出光興産株式会社 含窒素芳香族複素環誘導体およびそれを用いた有機エレクトロルミネッセンス素子
US9735385B2 (en) * 2011-08-22 2017-08-15 Merck Patent Gmbh Organic electroluminescence device
KR101720395B1 (ko) * 2011-09-15 2017-03-27 이데미쓰 고산 가부시키가이샤 방향족 아민 유도체 및 그것을 이용한 유기 전기발광 소자
KR101290015B1 (ko) * 2011-11-30 2013-07-30 주식회사 두산 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
WO2014009716A1 (en) 2012-07-10 2014-01-16 Cambridge Display Technology Limited Light-emitting compound
KR102017745B1 (ko) * 2012-10-12 2019-09-04 삼성디스플레이 주식회사 유기 발광 소자, 이의 제조 방법 및 이를 포함하는 유기 발광 표시 장치
JP6335428B2 (ja) * 2012-12-21 2018-05-30 出光興産株式会社 有機エレクトロルミネッセンス素子および電子機器
KR102149450B1 (ko) 2013-02-15 2020-09-01 에스에프씨주식회사 중수소화된 유기발광 화합물 및 이를 포함하는 유기 발광 소자
KR20140125576A (ko) 2013-04-19 2014-10-29 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
CN104538554B (zh) 2015-01-13 2017-01-25 北京科技大学 具有双组分混合电子传输/空穴阻挡层有机发光二极管
EP3208861A1 (en) * 2016-02-19 2017-08-23 Novaled GmbH Electron transport layer comprising a matrix compound mixture for an organic light-emitting diode (oled)
EP3312899B1 (en) * 2016-10-24 2021-04-07 Novaled GmbH Electron transport layer stack for an organic light-emitting diode

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101101975A (zh) * 2006-07-04 2008-01-09 株式会社半导体能源研究所 发光元件、发光装置和电子装置

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