WO2011105700A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant - Google Patents

Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant Download PDF

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WO2011105700A1
WO2011105700A1 PCT/KR2011/000404 KR2011000404W WO2011105700A1 WO 2011105700 A1 WO2011105700 A1 WO 2011105700A1 KR 2011000404 W KR2011000404 W KR 2011000404W WO 2011105700 A1 WO2011105700 A1 WO 2011105700A1
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organic electroluminescent
alkyl
aryl
arylsilyl
tri
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Sung Jin Eum
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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    • HELECTRICITY
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    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K11/00Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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    • C07ORGANIC CHEMISTRY
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    • C07D209/56Ring systems containing three or more rings
    • C07D209/80[b, c]- or [b, d]-condensed
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    • C07D209/80[b, c]- or [b, d]-condensed
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    • C07D223/14Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/18Dibenzazepines; Hydrogenated dibenzazepines
    • C07D223/22Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
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    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
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    • C07D279/101,4-Thiazines; Hydrogenated 1,4-thiazines
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    • C07D279/18[b, e]-condensed with two six-membered rings
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    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/10Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D417/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D421/10Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05BELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00Electroluminescent light sources
    • H05B33/12Light sources with substantially two-dimensional [2D] radiating surfaces
    • H05B33/14Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025Heterocyclic compounds characterised by ligands
    • C09K2211/1029Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Definitions

  • the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high fluorescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • R 13 through R 19 independently represent hydrogen, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl, (C2-60)heteroaryl containing one or more heteroatom(s) selected from N, O, S, Si and Se, (C1-60)alkoxy, (C1-C60)alkylthio, (C6-60)aryloxy, (C6-C60)arylthio, mono- or di(C1-60)alkylamino, mono- or di(C6-60)arylamino, (C6-30)aryl(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl, or R 13 and R 14 , R 16 and R 17 , and R 18 and R 19 are linked via (C3-C60)alkylene
  • a, b and c independently represent an integer from 1 to 4;
  • d represents an integer from 1 to 3;
  • the substituents comprising "(C3-C60)cycloalkyl” moiety may contain 3 to 60 carbon atoms, 3 to 20 carbon atoms, or 3 to 7 carbon atoms.
  • the substituents comprising "(C2-C60)alkenyl or alkynyl” moiety may contain 2 to 60 carbon atoms, 2 to 20 carbon atoms, or 2 to 10 carbon atoms.
  • the Y is a divalent group selected from following structures.
  • the electroluminescent layer means the layer where electroluminescence occurs, and it may be a single layer or a multi-layer that two or more layers are laminated.
  • a mixture of host-dopant is used according to the constitution of the present invention, noticeable improvement in luminous efficiency by the electroluminescent host may be confirmed.
  • R 91 through R 93 independently represent hydrogen, (C1-C60)alkyl or (C6-C60)aryl;
  • the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • N , N '-bis( ⁇ -naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in a blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention porte sur de nouveaux composés électroluminescents organiques, et sur des dispositifs électroluminescents organiques les comprenant. Comme les composés électroluminescents organiques présentent un rendement lumineux élevé dans la couleur bleue, et une excellente propriété de durée de vie du matériau, ils peuvent être utilisés pour fabriquer des diodes électroluminescentes organiques ayant une très bonne durée de vie de fonctionnement.
PCT/KR2011/000404 2010-02-26 2011-01-20 Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant Ceased WO2011105700A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020100017846A KR20110098293A (ko) 2010-02-26 2010-02-26 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자
KR10-2010-0017846 2010-02-26

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WO2011105700A1 true WO2011105700A1 (fr) 2011-09-01

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TW (1) TW201204807A (fr)
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103881065A (zh) * 2012-12-24 2014-06-25 海洋王照明科技股份有限公司 一种双极性共聚物蓝光主体材料及其制备方法与有机电致发光器件
WO2015047018A1 (fr) * 2013-09-30 2015-04-02 주식회사 두산 Composé organique et élément électroluminescent organique comprenant ce composé
US20150108448A1 (en) * 2012-05-30 2015-04-23 Guangdong Aglaia Optoelectronic Materials Co., Ltd Organic electronic material
US20150144898A1 (en) * 2012-05-30 2015-05-28 Guangdong Aglaia Optoelectronic Materials Co., Ltd Organic electroluminescent device
WO2015176981A1 (fr) * 2014-05-19 2015-11-26 Basf Se Éléments d'émission de lumière organique fluorescente ayant une efficacité élevée
US9871206B2 (en) 2012-09-12 2018-01-16 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescence device material, organic electroluminescence device and electronic device
US12622170B2 (en) 2014-05-19 2026-05-05 UDC Ireland Fluorescent organic light emitting elements having high efficiency

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KR101603384B1 (ko) * 2013-10-10 2016-03-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101603383B1 (ko) * 2013-09-30 2016-03-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20150103968A (ko) * 2014-03-04 2015-09-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102307342B1 (ko) * 2014-12-19 2021-10-01 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
WO2016105165A2 (fr) * 2014-12-26 2016-06-30 주식회사 두산 Composé électroluminescent organique et dispositif électroluminescent organique l'utilisant
KR20160091734A (ko) * 2015-01-26 2016-08-03 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
CN112876486B (zh) * 2021-01-25 2023-04-25 陕西莱特迈思光电材料有限公司 一种有机化合物及包含其的电子元件和电子装置

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9905774B2 (en) * 2012-05-30 2018-02-27 Guangdong Aglaia Optoelectronic Materials Co., Ltd Organic electronic material
TWI570984B (zh) * 2012-05-30 2017-02-11 Guangdong Aglaia Optoectronic Materials Co Ltd Organic electronic materials
US20150108448A1 (en) * 2012-05-30 2015-04-23 Guangdong Aglaia Optoelectronic Materials Co., Ltd Organic electronic material
US20150144898A1 (en) * 2012-05-30 2015-05-28 Guangdong Aglaia Optoelectronic Materials Co., Ltd Organic electroluminescent device
TWI495625B (zh) * 2012-05-30 2015-08-11 Guangdong Aglaia Optoectronic Materials Co Ltd Organic electroluminescent devices
US9871202B2 (en) * 2012-05-30 2018-01-16 Guangdong Aglaia Optoelectronic Materials Co., Ltd Organic electroluminescent device
US10510964B2 (en) 2012-09-12 2019-12-17 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescence device material, organic electroluminescence device and electronic device
US9871206B2 (en) 2012-09-12 2018-01-16 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescence device material, organic electroluminescence device and electronic device
CN103881065B (zh) * 2012-12-24 2016-06-22 海洋王照明科技股份有限公司 一种双极性共聚物蓝光主体材料及其制备方法与有机电致发光器件
CN103881065A (zh) * 2012-12-24 2014-06-25 海洋王照明科技股份有限公司 一种双极性共聚物蓝光主体材料及其制备方法与有机电致发光器件
WO2015047018A1 (fr) * 2013-09-30 2015-04-02 주식회사 두산 Composé organique et élément électroluminescent organique comprenant ce composé
JP2017518288A (ja) * 2014-05-19 2017-07-06 ユー・ディー・シー アイルランド リミテッド 高い効率を有する蛍光有機発光素子
WO2015176981A1 (fr) * 2014-05-19 2015-11-26 Basf Se Éléments d'émission de lumière organique fluorescente ayant une efficacité élevée
CN106414447A (zh) * 2014-05-19 2017-02-15 Udc 爱尔兰有限责任公司 具高效率的荧光有机发光元件
US10586930B2 (en) 2014-05-19 2020-03-10 Udc Ireland Limited Fluorescent organic light emitting elements having high efficiency
CN112778329A (zh) * 2014-05-19 2021-05-11 Udc 爱尔兰有限责任公司 具高效率的荧光有机发光元件
US11706978B2 (en) 2014-05-19 2023-07-18 Udc Ireland Limited Fluorescent organic light emitting elements having high efficiency
US12622170B2 (en) 2014-05-19 2026-05-05 UDC Ireland Fluorescent organic light emitting elements having high efficiency

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