WO2009011447A3 - Iridium complex compounds, organic electroluminescent devices and uses thereof - Google Patents

Iridium complex compounds, organic electroluminescent devices and uses thereof Download PDF

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Publication number
WO2009011447A3
WO2009011447A3 PCT/JP2008/063219 JP2008063219W WO2009011447A3 WO 2009011447 A3 WO2009011447 A3 WO 2009011447A3 JP 2008063219 W JP2008063219 W JP 2008063219W WO 2009011447 A3 WO2009011447 A3 WO 2009011447A3
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WO
WIPO (PCT)
Prior art keywords
group
groups
organic
blue
electron
Prior art date
Application number
PCT/JP2008/063219
Other languages
French (fr)
Other versions
WO2009011447A2 (en
Inventor
Takeshi Igarashi
Isamu Taguchi
Original Assignee
Showa Denko Kk
Takeshi Igarashi
Isamu Taguchi
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Showa Denko Kk, Takeshi Igarashi, Isamu Taguchi filed Critical Showa Denko Kk
Publication of WO2009011447A2 publication Critical patent/WO2009011447A2/en
Publication of WO2009011447A3 publication Critical patent/WO2009011447A3/en

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    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium compounds

Abstract

Blue-emitting phosphorescent compounds show high solubility in solvents for coating solutions in the production of organic EL devices and have excellent thermal stability. Organic EL devices having the blue-emitting phosphorescent compounds have high luminous efficiency and long life. A blue-emitting phosphorescent compound is an iridium complex compound represented by Formula (1) below: wherein R1 is a C2-30 organic group; R2 to R4 are each independently a hydrogen atom or a C1-10 alkyl group; R5 to R8 are each independently an electron-withdrawing group selected from the group consisting of halogen atoms, C1-10 fluorine-substituted alkyl groups, C1-10 fluorine-substituted alkoxy groups, cyano group, aldehyde group, C2-10 acyl groups, C2-10 alkoxycarbonyl groups, C1-10 aminocarbonyl groups, thiocyanate group and C1-10 sulfonyl groups, a C1-10 organic group optionally having a heteroatom (except the electron-withdrawing groups) or a hydrogen atom; and at least one of R5 to R8 is the electron-withdrawing group.
PCT/JP2008/063219 2007-07-19 2008-07-16 Iridium complex compounds, organic electroluminescent devices and uses thereof WO2009011447A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-188259 2007-07-19
JP2007188259A JP2009023938A (en) 2007-07-19 2007-07-19 Iridium complex compound, organic electroluminescent device and use thereof

Publications (2)

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WO2009011447A2 WO2009011447A2 (en) 2009-01-22
WO2009011447A3 true WO2009011447A3 (en) 2009-03-26

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PCT/JP2008/063219 WO2009011447A2 (en) 2007-07-19 2008-07-16 Iridium complex compounds, organic electroluminescent devices and uses thereof

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JP (1) JP2009023938A (en)
TW (1) TW200922941A (en)
WO (1) WO2009011447A2 (en)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010209317A (en) * 2009-02-10 2010-09-24 Mitsubishi Chemicals Corp Metal complex, composition for organic electroluminescent element, and organic electroluminescent element
JP2011105676A (en) * 2009-11-19 2011-06-02 Mitsubishi Chemicals Corp Organometallic complex, luminescent material, material of organic electroluminescent element, composition for organic electroluminescent element, organic electroluminescent element, organic el display and organic el illumination
EP2508527B1 (en) * 2009-11-30 2015-01-07 Samsung Electronics Co., Ltd. Iridium complex compound, organic electroluminescence element, and uses thereof
JP5546238B2 (en) * 2009-12-28 2014-07-09 昭和電工株式会社 Iridium complex compound, organic electroluminescence device and use thereof
TWI402329B (en) * 2010-04-12 2013-07-21 Univ Nat Cheng Kung Green processes for preparing luminescent iridium complexes and precursors thereof
JP2011256129A (en) * 2010-06-08 2011-12-22 Mitsubishi Chemicals Corp Organometallic complex material, composition for organic electroluminescent element, organic electroluminescent element, organic el display device, and organic el light
TWI529238B (en) 2011-04-15 2016-04-11 半導體能源研究所股份有限公司 Organic light-emitting element, organometallic complex, light-emitting device, electronic appliance, and lighting device
JP2013028757A (en) * 2011-07-29 2013-02-07 Canon Inc Organometallic complex and organic light emitting device including the same
JP2013147490A (en) 2011-12-23 2013-08-01 Semiconductor Energy Lab Co Ltd Iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
CN102617652A (en) * 2012-03-07 2012-08-01 南京邮电大学 Binuclear phosphorescent iridium complex with two-photon absorption characteristics and application of binuclear phosphorescent iridium complex
JP6166557B2 (en) 2012-04-20 2017-07-19 株式会社半導体エネルギー研究所 Phosphorescent organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
EP2883880B1 (en) * 2012-08-08 2016-11-30 Mitsubishi Chemical Corporation Iridium complex compound, and composition, organic electroluminescent element, display device and lighting device each cotaining the compound
JP6847589B2 (en) 2015-05-20 2021-03-24 株式会社半導体エネルギー研究所 Organometallic complexes, light emitting elements, light emitting devices, electronic devices, and lighting devices
JP6935176B2 (en) 2015-08-31 2021-09-15 株式会社半導体エネルギー研究所 Organometallic complexes, light emitting elements, light emitting devices, electronic devices, and lighting devices
KR20180063152A (en) 2015-09-30 2018-06-11 가부시키가이샤 한도오따이 에네루기 켄큐쇼 Organic metal complexes, light-emitting devices, light-emitting devices, electronic devices, and lighting devices
US9843002B2 (en) 2015-10-29 2017-12-12 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
US9960371B2 (en) 2015-12-18 2018-05-01 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
JP6651168B2 (en) * 2016-01-14 2020-02-19 国立研究開発法人産業技術総合研究所 Method for producing cyclometallated iridium complex
JP6861551B2 (en) 2016-04-01 2021-04-21 株式会社半導体エネルギー研究所 Organometallic complexes, light emitting elements, light emitting devices, electronic devices, and lighting devices
KR102388993B1 (en) 2016-04-01 2022-04-22 가부시키가이샤 한도오따이 에네루기 켄큐쇼 Light-emitting element, light-emitting device, electronic device, and lighting device
WO2018109621A1 (en) 2016-12-16 2018-06-21 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
JP7275042B2 (en) 2017-11-17 2023-05-17 株式会社半導体エネルギー研究所 Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
WO2020136496A1 (en) 2018-12-28 2020-07-02 株式会社半導体エネルギー研究所 Organic compound, light-emitting device, light-emitting apparatus, electronic instrument, and illumination apparatus
WO2022053905A1 (en) 2020-09-11 2022-03-17 株式会社半導体エネルギー研究所 Organic metal complex, light-emitting device, light-emitting apparatus, electronic equipment, and lighting device
CN116615514A (en) 2020-12-25 2023-08-18 株式会社半导体能源研究所 Organometallic complex, light-emitting device, light-emitting apparatus, electronic device, and lighting apparatus
DE102023116570A1 (en) 2022-06-29 2024-01-04 Semiconductor Energy Laboratory Co., Ltd. Light emitting device, light emitting device, electronic device and lighting device

Citations (1)

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Publication number Priority date Publication date Assignee Title
EP1191613A2 (en) * 2000-09-26 2002-03-27 Canon Kabushiki Kaisha Luminescence device, display apparatus and metal coordination compound

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1191613A2 (en) * 2000-09-26 2002-03-27 Canon Kabushiki Kaisha Luminescence device, display apparatus and metal coordination compound

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LASKAR, INAMUR R. ET AL: "Syntheses, photoluminescence and electroluminescence of some new blue-emitting phosphorescent iridium(III)-based materials", POLYHEDRON , 24(2), 189-200 CODEN: PLYHDE; ISSN: 0277-5387, 2005, XP002498410 *

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Publication number Publication date
TW200922941A (en) 2009-06-01
WO2009011447A2 (en) 2009-01-22
JP2009023938A (en) 2009-02-05

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