WO2014196685A1 - Composé pour élément opto-électronique organique, élément électroluminescent organique comprenant ce composé, et dispositif d'affichage comprenant ledit élément électroluminescent organique - Google Patents

Composé pour élément opto-électronique organique, élément électroluminescent organique comprenant ce composé, et dispositif d'affichage comprenant ledit élément électroluminescent organique Download PDF

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Publication number
WO2014196685A1
WO2014196685A1 PCT/KR2013/006588 KR2013006588W WO2014196685A1 WO 2014196685 A1 WO2014196685 A1 WO 2014196685A1 KR 2013006588 W KR2013006588 W KR 2013006588W WO 2014196685 A1 WO2014196685 A1 WO 2014196685A1
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Prior art keywords
formula
group
substituted
unsubstituted
compound
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Ceased
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PCT/KR2013/006588
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English (en)
Korean (ko)
Inventor
김현정
채미영
김욱
이남헌
허달호
김윤환
김준석
이상일
이현규
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Cheil Industries Inc
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Cheil Industries Inc
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Publication of WO2014196685A1 publication Critical patent/WO2014196685A1/fr
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Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least any one of the organic thin film layer is an organic according to an embodiment of the present invention It provides an organic light emitting device comprising a compound for optoelectronic devices.
  • hetero includes one to three heteroatoms selected from the group consisting of ⁇ , ⁇ , S, and ⁇ , and the remainder being carbon.
  • Aryl group means a substituent in which all elements of a cyclic substituent have a p-orbital, and these P-orbitals form a conjugate, and are monocyclic or fused ring polycyclic (i.e., And ring) functional groups that divide adjacent pairs of carbon atoms.
  • an electronic characteristic means the characteristic which has electroconductive characteristic along LUMO level, and facilitates the injection of the electron formed in the cathode into the light emitting layer, and the movement in the light emitting layer. More specifically, it may be similar to the property of attracting electrons.
  • X 1 to X 3 and X 8 to X 10 are independently from each other, N, CR 'or NR', wherein R 'is hydrogen, deuterium, halogen, cyano, substituted or An unsubstituted CI to CIO alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 17 R 18 R 19 , wherein R 17 to R 19 are independently of each other a C1 to C6 alkyl group : X 4 to X 7 And X 1 1 to X 14 are each independently ⁇ , or CR ′′, wherein R ′′ is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 To C20 aryl group, ⁇ is Ir, Os, Pt, Pb, Re, Ru, or Pd, L
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may have excellent heat resistance stability and lifespan characteristics and high luminous efficiency even at a low driving voltage. More specifically, the organic light emitting compound according to an embodiment of the present invention can reduce the triplet-triple extinction phenomenon that is most problematic in OLEDs by introducing a large substituent (TMS or t-butyl) to the ligand.
  • TMS triplet-triple extinction phenomenon
  • luminous efficiency and luminance characteristics can be improved as compared with the case of using a conventional phenylpyridine-based iridium compound. Can be.
  • R 19 is independently of each other a C1 to C6 alkyl group, at least one of the R 1 and R 2 may be -SiR 17 R 18 R 19 . However, it is not limited thereto.
  • the organic optoelectronic device may be an organic light emitting device, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photosensitive drum, or an organic memory device.
  • a material having a large work function is preferable to facilitate hole injection into the organic thin film layer.
  • Specific examples of the positive electrodelization include nickel, platinum, vanadium, chromium, copper, zinc, metals such as gold or alloys thereof, zinc oxide, indium oxide,
  • Fk6 iridium (ni) bis (4,6-difluorophenylpyridinato) tetrakis (l-pyrazolyl) borate
  • Fir6 represented by the formula Z-3 phosphorescent dopant for blue (blue), as Preparation Example 1 using the compound D-1 prepared by excluding a point 10 weight 0/0 doped and Comparative Example 1 An organic light emitting device was manufactured in the same manner.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 2 instead of the dopant according to Preparation Example 1.
  • Example 3
  • Example 5 An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant according to Preparation Example 5.

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

Abstract

L'invention concerne un composé pour élément opto-électronique organique, un élément électroluminescent organique comprenant ce composé, et un dispositif d'affichage comprenant cet élément électroluminescent organique. Le composé pour élément optoélectronique organique selon l'invention est représenté par la formule (1).
PCT/KR2013/006588 2013-06-03 2013-07-23 Composé pour élément opto-électronique organique, élément électroluminescent organique comprenant ce composé, et dispositif d'affichage comprenant ledit élément électroluminescent organique Ceased WO2014196685A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2013-0063499 2013-06-03
KR1020130063499A KR20140142000A (ko) 2013-06-03 2013-06-03 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치

Publications (1)

Publication Number Publication Date
WO2014196685A1 true WO2014196685A1 (fr) 2014-12-11

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PCT/KR2013/006588 Ceased WO2014196685A1 (fr) 2013-06-03 2013-07-23 Composé pour élément opto-électronique organique, élément électroluminescent organique comprenant ce composé, et dispositif d'affichage comprenant ledit élément électroluminescent organique

Country Status (2)

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KR (1) KR20140142000A (fr)
WO (1) WO2014196685A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017170916A1 (fr) * 2016-03-31 2017-10-05 住友化学株式会社 Complexe métallique, composition et élément électroluminescent
US10854827B2 (en) * 2014-12-17 2020-12-01 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102613048B1 (ko) * 2015-08-18 2023-12-15 삼성전자주식회사 유기금속 화합물 및 이를 포함한 유기 발광 소자
EP3133078B1 (fr) 2015-08-18 2019-01-30 Samsung Electronics Co., Ltd. Composé organométallique et dispositif électroluminescent organique l'incluant

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009076826A (ja) * 2007-09-25 2009-04-09 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2012164731A (ja) * 2011-02-04 2012-08-30 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス材料、有機エレクトロルミネッセンス素子、表示装置および照明装置
US20120292601A1 (en) * 2011-05-19 2012-11-22 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology
WO2012170571A1 (fr) * 2011-06-08 2012-12-13 Universal Display Corporation Complexes hétéroleptiques de carbènes d'iridium et dispositif électroluminescent utilisant ceux-ci

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009076826A (ja) * 2007-09-25 2009-04-09 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2012164731A (ja) * 2011-02-04 2012-08-30 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス材料、有機エレクトロルミネッセンス素子、表示装置および照明装置
US20120292601A1 (en) * 2011-05-19 2012-11-22 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology
WO2012170571A1 (fr) * 2011-06-08 2012-12-13 Universal Display Corporation Complexes hétéroleptiques de carbènes d'iridium et dispositif électroluminescent utilisant ceux-ci

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10854827B2 (en) * 2014-12-17 2020-12-01 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
US11991921B2 (en) 2014-12-17 2024-05-21 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
WO2017170916A1 (fr) * 2016-03-31 2017-10-05 住友化学株式会社 Complexe métallique, composition et élément électroluminescent
JPWO2017170916A1 (ja) * 2016-03-31 2018-05-31 住友化学株式会社 金属錯体、組成物及び発光素子
CN108884118A (zh) * 2016-03-31 2018-11-23 住友化学株式会社 金属络合物、组合物及发光元件

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