WO2012036482A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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Publication number
WO2012036482A1
WO2012036482A1 PCT/KR2011/006810 KR2011006810W WO2012036482A1 WO 2012036482 A1 WO2012036482 A1 WO 2012036482A1 KR 2011006810 W KR2011006810 W KR 2011006810W WO 2012036482 A1 WO2012036482 A1 WO 2012036482A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
alkyl
aryl
organic electroluminescent
Prior art date
Application number
PCT/KR2011/006810
Other languages
English (en)
French (fr)
Inventor
Hyo Nim Shin
Soo-Jin Hwang
Hee Sook Kim
Seok Keun Yoon
Mi Ja Lee
Nam Kyun Kim
Young Jun Cho
Hyuck Joo Kwon
Kyung Joo Lee
Bong Ok Kim
Original Assignee
Rohm And Haas Electronic Materials Korea 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 Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to JP2013529060A priority Critical patent/JP2013539750A/ja
Priority to CN2011800555279A priority patent/CN103221406A/zh
Priority to CN201810756909.8A priority patent/CN109020960B/zh
Priority to EP11825442.4A priority patent/EP2616462A4/en
Publication of WO2012036482A1 publication Critical patent/WO2012036482A1/en

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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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • 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
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • 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
    • 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
    • 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
    • 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
    • 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
    • C09K2211/1018—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
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • 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

  • h represents an integer of 1 to 5, and when h is an integer of 2 or greater, each R 8 may be identical or different from each other;
  • R 204 through R 219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF 5 , substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl,
  • Compound 16 (7.6g, 11.0mmol, 61%) was prepared from Compound 2-4 (9.8g, 18.05mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (5.7g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 25 was used as the host material in the electroluminescent layer.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Laminated Bodies (AREA)
PCT/KR2011/006810 2010-09-17 2011-09-16 Novel organic electroluminescent compounds and organic electroluminescent device using the same WO2012036482A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2013529060A JP2013539750A (ja) 2010-09-17 2011-09-16 新規有機電界発光化合物およびこれを使用する有機電界発光素子
CN2011800555279A CN103221406A (zh) 2010-09-17 2011-09-16 新有机电致发光化合物和使用该化合物的有机电致发光器件
CN201810756909.8A CN109020960B (zh) 2010-09-17 2011-09-16 新有机电致发光化合物和使用该化合物的有机电致发光器件
EP11825442.4A EP2616462A4 (en) 2010-09-17 2011-09-16 NEW ORGANIC ELECTROLUMINESCENSE COMPOUNDS AND ORGANIC ELECTROLUMINESCENCE DEVICE THEREWITH

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20100091545 2010-09-17
KR10-2010-0091545 2010-09-17
KR10-2011-0092422 2011-09-14
KR1020110092422A KR101477614B1 (ko) 2010-09-17 2011-09-14 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자

Publications (1)

Publication Number Publication Date
WO2012036482A1 true WO2012036482A1 (en) 2012-03-22

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2011/006810 WO2012036482A1 (en) 2010-09-17 2011-09-16 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Country Status (6)

Country Link
EP (1) EP2616462A4 (ja)
JP (3) JP2013539750A (ja)
KR (1) KR101477614B1 (ja)
CN (2) CN109020960B (ja)
TW (1) TWI560258B (ja)
WO (1) WO2012036482A1 (ja)

Cited By (42)

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JP2012087114A (ja) * 2010-09-21 2012-05-10 Semiconductor Energy Lab Co Ltd カルバゾール誘導体、発光素子用材料及び有機半導体材料
WO2012121561A1 (en) * 2011-03-08 2012-09-13 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2012134124A1 (en) * 2011-03-25 2012-10-04 Rohm And Haas Electronic Materials Korea Ltd. Novel compounds for organic electronic material and organic electroluminescent device using the same
WO2012141499A1 (en) * 2011-04-12 2012-10-18 Rohm And Haas Electronic Materials Korea Ltd. Novel compounds for organic electronic material and organic electroluminescent device using the same
WO2012150826A1 (en) * 2011-05-03 2012-11-08 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and an organic electroluminescent device using the same
WO2012165844A1 (en) * 2011-05-30 2012-12-06 Rohm And Haas Electronic Materials Korea Ltd. Novel compounds for organic electronic material and organic electroluminescent device using the same
WO2013012298A1 (en) * 2011-07-21 2013-01-24 Rohm And Haas Electronic Materials Korea Ltd. 9h-carbazole compounds and electroluminescent devices involving them
WO2013032278A1 (en) * 2011-09-01 2013-03-07 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2013162284A1 (en) * 2012-04-27 2013-10-31 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device comprising the same
WO2014051004A1 (ja) * 2012-09-28 2014-04-03 出光興産株式会社 有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子
CN103764786A (zh) * 2011-05-03 2014-04-30 罗门哈斯电子材料韩国有限公司 新型有机电致发光化合物以及使用该化合物的有机电致发光器件
WO2014088290A1 (en) * 2012-12-04 2014-06-12 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compounds and organic electroluminescent device comprising the same
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JP2016526030A (ja) * 2013-05-13 2016-09-01 チェイル インダストリーズ インコーポレイテッド 有機光電子素子用化合物、これを含む有機発光素子および前記有機発光素子を含む表示装置
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KR20120030009A (ko) 2012-03-27
EP2616462A1 (en) 2013-07-24
EP2616462A4 (en) 2014-02-19
JP6672416B2 (ja) 2020-03-25
CN103221406A (zh) 2013-07-24
TWI560258B (en) 2016-12-01
JP2019050382A (ja) 2019-03-28
CN109020960B (zh) 2022-05-10
JP2017031167A (ja) 2017-02-09
CN109020960A (zh) 2018-12-18
TW201224110A (en) 2012-06-16
KR101477614B1 (ko) 2014-12-31

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