WO2020153653A1 - 화합물 및 이를 포함하는 유기발광소자 - Google Patents

화합물 및 이를 포함하는 유기발광소자 Download PDF

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Publication number
WO2020153653A1
WO2020153653A1 PCT/KR2020/000736 KR2020000736W WO2020153653A1 WO 2020153653 A1 WO2020153653 A1 WO 2020153653A1 KR 2020000736 W KR2020000736 W KR 2020000736W WO 2020153653 A1 WO2020153653 A1 WO 2020153653A1
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Prior art keywords
group
substituted
unsubstituted
light emitting
formula
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PCT/KR2020/000736
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English (en)
French (fr)
Korean (ko)
Inventor
서상덕
김민준
김동희
김서연
이다정
최승원
이동훈
Original Assignee
주식회사 엘지화학
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Priority to CN202080002724.3A priority Critical patent/CN112204030B/zh
Priority to CN202310478696.8A priority patent/CN116621842A/zh
Publication of WO2020153653A1 publication Critical patent/WO2020153653A1/ko

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic 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
    • C07D405/14—Heterocyclic 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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the benzoindolocarbazole unit contains a naphthalene ring, which lowers the triplet energy, and consequently, the singlet energy and triplet energy are both small, which is advantageous for energy transfer to the red dopant, so as a host of the red light emitting layer. It is appropriate to use.
  • B11 is a substituted or unsubstituted phenyl group.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, or may combine with an adjacent group to form a substituted or unsubstituted ring.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or combined with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms. .
  • R2 and R3 are hydrogen; heavy hydrogen; Or a phenyl group, a plurality of R2 or a plurality of R3 are bonded to each other and a benzene ring; Benzofuran ring; Benzothiophene ring; Alternatively, an indene ring substituted with a methyl group is formed.
  • heterocyclic group can be applied to the heterocycle except that it is divalent.
  • r1 is an integer of 0 to 1.
  • R2 and R3 are hydrogen; heavy hydrogen; Or a phenyl group, In multiple R2 or In a plurality of R3 are combined with each other to form any one of the following structures.
  • the organic light emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer 3.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • Alq3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole compounds Benzoxazole, benzthiazole and benzimidazole compounds
  • Poly(p-phenylenevinylene) (PPV) polymers Spiro compounds
  • Polyfluorene, rubrene, and the like but are not limited to these.
  • R c and R d are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Amino group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms containing any one or more selected from the group consisting of N, O and S.
  • C12 and C13 are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
  • the formula 8 may be represented by any one of the following compounds.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/KR2020/000736 2019-01-25 2020-01-15 화합물 및 이를 포함하는 유기발광소자 WO2020153653A1 (ko)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202080002724.3A CN112204030B (zh) 2019-01-25 2020-01-15 化合物及包含其的有机发光器件
CN202310478696.8A CN116621842A (zh) 2019-01-25 2020-01-15 化合物及包含其的有机发光器件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2019-0009968 2019-01-25
KR20190009968 2019-01-25

Publications (1)

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WO2020153653A1 true WO2020153653A1 (ko) 2020-07-30

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KR (1) KR102338205B1 (zh)
CN (2) CN112204030B (zh)
WO (1) WO2020153653A1 (zh)

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CN117343061A (zh) * 2022-06-24 2024-01-05 陕西莱特光电材料股份有限公司 含氮化合物及有机电致发光器件和电子装置

Citations (5)

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KR20150108330A (ko) * 2014-03-17 2015-09-25 롬엔드하스전자재료코리아유한회사 전자 버퍼 재료 및 이를 포함하는 유기 전계 발광 소자
KR20170010715A (ko) * 2015-07-20 2017-02-01 롬엔드하스전자재료코리아유한회사 지연 형광용 발광 재료 및 이를 포함하는 유기 전계 발광 소자
KR20170119291A (ko) * 2016-04-18 2017-10-26 롬엔드하스전자재료코리아유한회사 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
KR20170133281A (ko) * 2016-05-25 2017-12-05 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 디바이스
WO2018021737A1 (ko) * 2016-07-29 2018-02-01 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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KR102152194B1 (ko) * 2016-08-18 2020-09-04 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
US10944060B2 (en) * 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
KR20200046339A (ko) * 2018-10-24 2020-05-07 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20200049635A (ko) * 2018-10-31 2020-05-08 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
CN110862381B (zh) 2019-12-04 2021-03-19 宁波卢米蓝新材料有限公司 一种有机电致发光化合物及其制备方法和应用

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Publication number Priority date Publication date Assignee Title
KR20150108330A (ko) * 2014-03-17 2015-09-25 롬엔드하스전자재료코리아유한회사 전자 버퍼 재료 및 이를 포함하는 유기 전계 발광 소자
KR20170010715A (ko) * 2015-07-20 2017-02-01 롬엔드하스전자재료코리아유한회사 지연 형광용 발광 재료 및 이를 포함하는 유기 전계 발광 소자
KR20170119291A (ko) * 2016-04-18 2017-10-26 롬엔드하스전자재료코리아유한회사 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
KR20170133281A (ko) * 2016-05-25 2017-12-05 유니버셜 디스플레이 코포레이션 유기 전계발광 물질 및 디바이스
WO2018021737A1 (ko) * 2016-07-29 2018-02-01 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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KR20200092874A (ko) 2020-08-04
KR102338205B1 (ko) 2021-12-10
CN112204030A (zh) 2021-01-08
CN112204030B (zh) 2023-09-01
CN116621842A (zh) 2023-08-22

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