WO2008149968A1 - Aromatic amine derivative and organic electroluminescent device - Google Patents

Aromatic amine derivative and organic electroluminescent device Download PDF

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Publication number
WO2008149968A1
WO2008149968A1 PCT/JP2008/060425 JP2008060425W WO2008149968A1 WO 2008149968 A1 WO2008149968 A1 WO 2008149968A1 JP 2008060425 W JP2008060425 W JP 2008060425W WO 2008149968 A1 WO2008149968 A1 WO 2008149968A1
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WO
WIPO (PCT)
Prior art keywords
unsubstituted
substituted
electroluminescent device
organic electroluminescent
aromatic amine
Prior art date
Application number
PCT/JP2008/060425
Other languages
French (fr)
Japanese (ja)
Inventor
Masakazu Funahashi
Original Assignee
Idemitsu Kosan Co., Ltd.
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 Idemitsu Kosan Co., Ltd. filed Critical Idemitsu Kosan Co., Ltd.
Publication of WO2008149968A1 publication Critical patent/WO2008149968A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • 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, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional 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
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

An organic electroluminescent device having a long life and a high luminescent efficiency and being capable of emitting blue light of a high color purity; and an aromatic amine derivative represented by the following general formula (I) whereby the organic electroluminescent device is enabled. The organic electroluminescent device as described above has one or more organic thin film layers wherein a luminescent layer is located between an anode and a cathode and at least one of the organic thin film layers contains the aromatic amine derivative as described above. (I) wherein R1 represents a monovalent group derived form substituted or unsubstituted chrysene; R2 represents a single bond, a substituted or unsubstituted C6-50 arylene group, or a substituted or unsubstituted C3-50 heterocyclic group; and A and B independently represent each a substituted or unsubstituted C6-50 aryl group or a substituted or unsubstituted C3-50 heterocyclic group; provided that in the case where R2 is a single bond and -NAB attaches to the 1- or 6-position of the chrysene structure, the chrysene structure has at least one substituent other than -NAB.
PCT/JP2008/060425 2007-06-07 2008-06-06 Aromatic amine derivative and organic electroluminescent device WO2008149968A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-151549 2007-06-07
JP2007151549 2007-06-07

Publications (1)

Publication Number Publication Date
WO2008149968A1 true WO2008149968A1 (en) 2008-12-11

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Family Applications (1)

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PCT/JP2008/060425 WO2008149968A1 (en) 2007-06-07 2008-06-06 Aromatic amine derivative and organic electroluminescent device

Country Status (2)

Country Link
TW (1) TW200916434A (en)
WO (1) WO2008149968A1 (en)

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110037381A1 (en) * 2009-08-13 2011-02-17 E. I. Du Pont De Nemours And Company Chrysene derivative materials
US20110147718A1 (en) * 2009-12-21 2011-06-23 E.I. Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition
WO2011132683A1 (en) * 2010-04-20 2011-10-27 出光興産株式会社 Bis-carbazole derivative, material for organic electroluminescent element and organic electroluminescent element using same
US8115378B2 (en) 2006-12-28 2012-02-14 E. I. Du Pont De Nemours And Company Tetra-substituted chrysenes for luminescent applications
US8158831B2 (en) 2007-06-01 2012-04-17 E I Du Pont De Nemours And Company Chrysene compounds for deep blue luminescent applications
US8192848B2 (en) 2008-01-11 2012-06-05 E I Du Pont De Nemours And Company Substituted pyrenes and associated production methods for luminescent applications
US8257836B2 (en) 2006-12-29 2012-09-04 E I Du Pont De Nemours And Company Di-substituted pyrenes for luminescent applications
US8263973B2 (en) 2008-12-19 2012-09-11 E I Du Pont De Nemours And Company Anthracene compounds for luminescent applications
US8273468B2 (en) 2007-06-01 2012-09-25 E I Du Pont De Nemours And Company Green luminescent materials
US8431245B2 (en) 2009-09-29 2013-04-30 E. I. Du Pont De Nemours And Company Deuterated compounds for luminescent applications
US8497495B2 (en) 2009-04-03 2013-07-30 E I Du Pont De Nemours And Company Electroactive materials
US8531100B2 (en) 2008-12-22 2013-09-10 E I Du Pont De Nemours And Company Deuterated compounds for luminescent applications
US8592239B2 (en) 2009-07-27 2013-11-26 E I Du Pont De Nemours And Company Process and materials for making contained layers and devices made with same
US8648333B2 (en) 2009-10-19 2014-02-11 E I Du Pont De Nemours And Company Triarylamine compounds for use in organic light-emitting diodes
US8759818B2 (en) 2009-02-27 2014-06-24 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
US8932733B2 (en) 2008-12-19 2015-01-13 E I Du Pont De Nemours And Company Chrysene derivative host materials
US8937300B2 (en) 2009-10-19 2015-01-20 E I Du Pont De Nemours And Company Triarylamine compounds for use in organic light-emitting diodes
US9133095B2 (en) 2009-07-01 2015-09-15 E I Du Pont De Nemours And Company Chrysene compounds for luminescent applications
JP2015529632A (en) * 2012-06-06 2015-10-08 メルク パテント ゲーエムベーハー Phenanthrene compounds for organic electronic devices
US9260657B2 (en) 2009-05-19 2016-02-16 E I Du Pont De Nemours And Company Chrysene compounds for luminescent applications
US9293716B2 (en) 2010-12-20 2016-03-22 Ei Du Pont De Nemours And Company Compositions for electronic applications
US9496506B2 (en) 2009-10-29 2016-11-15 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
CN108059582A (en) * 2018-01-19 2018-05-22 李现伟 A kind of biphenyl compound and its application in 1,3,6,8- tetrabromo pyrenes are prepared
CN108059583A (en) * 2018-01-19 2018-05-22 李现伟 A kind of biphenyl compound and its application in 1- bromine pyrenes are prepared
CN108250034A (en) * 2018-01-19 2018-07-06 李现伟 A kind of biphenyl compound and its application in 1,3,6- tribromo pyrenes are prepared
CN114478154A (en) * 2022-02-25 2022-05-13 西安欧得光电材料有限公司 Industrial synthesis method of picene

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WO2005061656A1 (en) * 2003-12-19 2005-07-07 Idemitsu Kosan Co., Ltd. Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
WO2005115950A1 (en) * 2004-05-27 2005-12-08 Idemitsu Kosan Co., Ltd. Asymmetric pyrene derivative and organic electroluminescent device using same

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JPH03223764A (en) * 1989-06-14 1991-10-02 Ricoh Co Ltd Electrophotographic sensitive body
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WO2005115950A1 (en) * 2004-05-27 2005-12-08 Idemitsu Kosan Co., Ltd. Asymmetric pyrene derivative and organic electroluminescent device using same

Cited By (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8115378B2 (en) 2006-12-28 2012-02-14 E. I. Du Pont De Nemours And Company Tetra-substituted chrysenes for luminescent applications
US8257836B2 (en) 2006-12-29 2012-09-04 E I Du Pont De Nemours And Company Di-substituted pyrenes for luminescent applications
US8604247B2 (en) 2007-06-01 2013-12-10 E I Du Pont De Nemours And Company Chrysenes for deep blue luminescent applications
US8273468B2 (en) 2007-06-01 2012-09-25 E I Du Pont De Nemours And Company Green luminescent materials
US8158831B2 (en) 2007-06-01 2012-04-17 E I Du Pont De Nemours And Company Chrysene compounds for deep blue luminescent applications
US8383251B2 (en) 2008-01-11 2013-02-26 E I Du Pont De Nemours And Company Substituted pyrenes and associated production methods for luminescent applications
US8192848B2 (en) 2008-01-11 2012-06-05 E I Du Pont De Nemours And Company Substituted pyrenes and associated production methods for luminescent applications
US8263973B2 (en) 2008-12-19 2012-09-11 E I Du Pont De Nemours And Company Anthracene compounds for luminescent applications
US8932733B2 (en) 2008-12-19 2015-01-13 E I Du Pont De Nemours And Company Chrysene derivative host materials
US8531100B2 (en) 2008-12-22 2013-09-10 E I Du Pont De Nemours And Company Deuterated compounds for luminescent applications
US8759818B2 (en) 2009-02-27 2014-06-24 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
US8890131B2 (en) 2009-02-27 2014-11-18 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
US8497495B2 (en) 2009-04-03 2013-07-30 E I Du Pont De Nemours And Company Electroactive materials
US9260657B2 (en) 2009-05-19 2016-02-16 E I Du Pont De Nemours And Company Chrysene compounds for luminescent applications
US9133095B2 (en) 2009-07-01 2015-09-15 E I Du Pont De Nemours And Company Chrysene compounds for luminescent applications
US8592239B2 (en) 2009-07-27 2013-11-26 E I Du Pont De Nemours And Company Process and materials for making contained layers and devices made with same
JP2013501783A (en) * 2009-08-13 2013-01-17 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Chrysene derivative material
WO2011019360A1 (en) 2009-08-13 2011-02-17 E. I. Du Pont De Nemours And Company Chrysene derivative materials
CN102834483A (en) * 2009-08-13 2012-12-19 E.I.内穆尔杜邦公司 Chrysene derivative materials
US20130187140A1 (en) * 2009-08-13 2013-07-25 E I Du Pont De Nemours And Company Chrysene derivative materials
EP2464709A1 (en) * 2009-08-13 2012-06-20 E. I. du Pont de Nemours and Company Chrysene derivative materials
KR101811507B1 (en) * 2009-08-13 2017-12-21 이 아이 듀폰 디 네모아 앤드 캄파니 Chrysene derivative materials
US20110037381A1 (en) * 2009-08-13 2011-02-17 E. I. Du Pont De Nemours And Company Chrysene derivative materials
KR101545774B1 (en) 2009-08-13 2015-08-19 이 아이 듀폰 디 네모아 앤드 캄파니 Chrysene derivative materials
US8968883B2 (en) * 2009-08-13 2015-03-03 E I Du Pont De Nemours And Company Chrysene derivative materials
EP2464709A4 (en) * 2009-08-13 2013-02-20 Du Pont Chrysene derivative materials
US8431245B2 (en) 2009-09-29 2013-04-30 E. I. Du Pont De Nemours And Company Deuterated compounds for luminescent applications
US8937300B2 (en) 2009-10-19 2015-01-20 E I Du Pont De Nemours And Company Triarylamine compounds for use in organic light-emitting diodes
US8648333B2 (en) 2009-10-19 2014-02-11 E I Du Pont De Nemours And Company Triarylamine compounds for use in organic light-emitting diodes
US9496506B2 (en) 2009-10-29 2016-11-15 E I Du Pont De Nemours And Company Deuterated compounds for electronic applications
US20110147718A1 (en) * 2009-12-21 2011-06-23 E.I. Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition
US8617720B2 (en) * 2009-12-21 2013-12-31 E I Du Pont De Nemours And Company Electroactive composition and electronic device made with the composition
WO2011132683A1 (en) * 2010-04-20 2011-10-27 出光興産株式会社 Bis-carbazole derivative, material for organic electroluminescent element and organic electroluminescent element using same
US8877352B2 (en) 2010-04-20 2014-11-04 Idemitsu Kosan Co., Ltd. Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same
US8652654B2 (en) 2010-04-20 2014-02-18 Idemitsu Kosan Co., Ltd. Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same
JP5562970B2 (en) * 2010-04-20 2014-07-30 出光興産株式会社 Biscarbazole derivative, material for organic electroluminescence device, and organic electroluminescence device using the same
US8940414B2 (en) 2010-04-20 2015-01-27 Idemitsu Kosan Co., Ltd. Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same
US8865323B2 (en) 2010-04-20 2014-10-21 Idemitsu Kosan Co., Ltd. Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same
US10193077B2 (en) 2010-04-20 2019-01-29 Idemitsu Kosan Co., Ltd. Biscarbazole derivative, material for organic electroluminescence device and organic electroluminescence device using the same
US9293716B2 (en) 2010-12-20 2016-03-22 Ei Du Pont De Nemours And Company Compositions for electronic applications
US10446759B2 (en) 2012-06-06 2019-10-15 Merck Patent Gmbh Phenanthrene compounds for organic electronic devices
US9799833B2 (en) 2012-06-06 2017-10-24 Merck Patent Gmbh Phenanthrene compounds for organic electronic devices
JP2015529632A (en) * 2012-06-06 2015-10-08 メルク パテント ゲーエムベーハー Phenanthrene compounds for organic electronic devices
US11424411B2 (en) 2012-06-06 2022-08-23 Merck Patent Gmbh Phenanthrene compounds for organic electronic devices
CN108059582A (en) * 2018-01-19 2018-05-22 李现伟 A kind of biphenyl compound and its application in 1,3,6,8- tetrabromo pyrenes are prepared
CN108059583A (en) * 2018-01-19 2018-05-22 李现伟 A kind of biphenyl compound and its application in 1- bromine pyrenes are prepared
CN108250034A (en) * 2018-01-19 2018-07-06 李现伟 A kind of biphenyl compound and its application in 1,3,6- tribromo pyrenes are prepared
CN114478154A (en) * 2022-02-25 2022-05-13 西安欧得光电材料有限公司 Industrial synthesis method of picene
CN114478154B (en) * 2022-02-25 2023-11-21 西安欧得光电材料有限公司 Industrial synthesis method of picene

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