WO2010036765A1 - Organoselenium materials and their uses in organic light emitting devices - Google Patents
Organoselenium materials and their uses in organic light emitting devices Download PDFInfo
- Publication number
- WO2010036765A1 WO2010036765A1 PCT/US2009/058162 US2009058162W WO2010036765A1 WO 2010036765 A1 WO2010036765 A1 WO 2010036765A1 US 2009058162 W US2009058162 W US 2009058162W WO 2010036765 A1 WO2010036765 A1 WO 2010036765A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- light emitting
- layer
- organic light
- emitting device
- organoselenium
- Prior art date
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- 0 *1C(N(c2ccccc2)c(cc2)ccc2-c(cc2)ccc2N(c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)c2cccc(-c3cccc(N(c4ccccc4)c(cc4)ccc4N(c(cc4)ccc4N(c4ccccc4)c4ccccc4)c4ccc5[s]c6ccccc6c5c4)c3)c2)c(cc2)ccc2-c2cccc3c2[s]c2ccccc32)=CC=CC=C1 Chemical compound *1C(N(c2ccccc2)c(cc2)ccc2-c(cc2)ccc2N(c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)c2cccc(-c3cccc(N(c4ccccc4)c(cc4)ccc4N(c(cc4)ccc4N(c4ccccc4)c4ccccc4)c4ccc5[s]c6ccccc6c5c4)c3)c2)c(cc2)ccc2-c2cccc3c2[s]c2ccccc32)=CC=CC=C1 0.000 description 19
- NYNNTEUNPFBRCR-UHFFFAOYSA-N C(C1)C=CCc2c1c1ccccc1c1ccccc21 Chemical compound C(C1)C=CCc2c1c1ccccc1c1ccccc21 NYNNTEUNPFBRCR-UHFFFAOYSA-N 0.000 description 1
- OOOWNSOBBPAWLL-UHFFFAOYSA-N C(C1)C=Cc(c2ccccc22)c1[n]2-c(cc1c2c3)ccc1[s]c2ccc3-[n]1c(ccc(-c(cc2)c(c(cccc3)c3[s]3)c3c2-c(cccc2)c2-c(cccc2)c2-c2c3[s]c(cccc4)c4c3ccc2)c2)c2c2c1cccc2 Chemical compound C(C1)C=Cc(c2ccccc22)c1[n]2-c(cc1c2c3)ccc1[s]c2ccc3-[n]1c(ccc(-c(cc2)c(c(cccc3)c3[s]3)c3c2-c(cccc2)c2-c(cccc2)c2-c2c3[s]c(cccc4)c4c3ccc2)c2)c2c2c1cccc2 OOOWNSOBBPAWLL-UHFFFAOYSA-N 0.000 description 1
- LZNYPBPKMSGZDO-UHFFFAOYSA-N C(C1)C=Cc2c1cccc2N(c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1cccc(-c2cccc(-c(cc3)ccc3N(c(cc3)ccc3-c3ccccc3)c(cc3)ccc3-c(cc3)ccc3N(c(cc3)ccc3-c(cc3)cc4c3[s]c3ccccc43)c3cccc4c3cccc4)c2)c1)c(cc1)ccc1-c1c2[s]c3ccccc3c2ccc1 Chemical compound C(C1)C=Cc2c1cccc2N(c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1cccc(-c2cccc(-c(cc3)ccc3N(c(cc3)ccc3-c3ccccc3)c(cc3)ccc3-c(cc3)ccc3N(c(cc3)ccc3-c(cc3)cc4c3[s]c3ccccc43)c3cccc4c3cccc4)c2)c1)c(cc1)ccc1-c1c2[s]c3ccccc3c2ccc1 LZNYPBPKMSGZDO-UHFFFAOYSA-N 0.000 description 1
- VKIJMMQJFZICTH-UHFFFAOYSA-N C(C12)=CC=CC1Sc(cc1)c2cc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccccc1)c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccccc1 Chemical compound C(C12)=CC=CC1Sc(cc1)c2cc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccccc1)c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c1ccccc1 VKIJMMQJFZICTH-UHFFFAOYSA-N 0.000 description 1
- ACJWOTBRGHXPCJ-UHFFFAOYSA-N C(c(cc1)ccc1C(C=C1)=CCC=C1N(c1ccccc1)c(cc1)ccc1-c1c2[s]c3ccccc3c2ccc1)N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1cccc(C(C=CC2)=CC2c(cc2)ccc2N(c(cc2)ccc2-c2ccccc2)c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)c(cc2)ccc2-c2ccc3[s]c(cccc4)c4c3c2)c1 Chemical compound C(c(cc1)ccc1C(C=C1)=CCC=C1N(c1ccccc1)c(cc1)ccc1-c1c2[s]c3ccccc3c2ccc1)N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c1cccc(C(C=CC2)=CC2c(cc2)ccc2N(c(cc2)ccc2-c2ccccc2)c(cc2)ccc2-c(cc2)ccc2N(c2ccccc2)c(cc2)ccc2-c2ccc3[s]c(cccc4)c4c3c2)c1 ACJWOTBRGHXPCJ-UHFFFAOYSA-N 0.000 description 1
- POAINWPGJWNQGY-JXSKNCHLSA-N C/C=C\C(\C)=C(/C)\c1ccccc1C Chemical compound C/C=C\C(\C)=C(/C)\c1ccccc1C POAINWPGJWNQGY-JXSKNCHLSA-N 0.000 description 1
- PYVMYNDKYYLPND-FNNBZGKSSA-N C/C=C\C=C(/C=C)\c1ccccc1 Chemical compound C/C=C\C=C(/C=C)\c1ccccc1 PYVMYNDKYYLPND-FNNBZGKSSA-N 0.000 description 1
- PZPJOKDKBAMWEV-ALCCZGGFSA-N C/C=C\c1c(C=C)c(C)c(C)[s]1 Chemical compound C/C=C\c1c(C=C)c(C)c(C)[s]1 PZPJOKDKBAMWEV-ALCCZGGFSA-N 0.000 description 1
- ZGXAEIBBQYBPRU-RRIGCHOWSA-N C/N=C\C=C(/C=C)\C1=C[IH]NC=C1 Chemical compound C/N=C\C=C(/C=C)\C1=C[IH]NC=C1 ZGXAEIBBQYBPRU-RRIGCHOWSA-N 0.000 description 1
- LOIIPAPIFHZBBZ-UHFFFAOYSA-N C1C=CC(N(c(cc2)ccc2-c2ccc(c(cccc3N(c(cc4)ccc4N(c4ccccc4)c4ccccc4)c(cc4)ccc4N(c4ccccc4)c4ccccc4)c3[s]3)c3c2)c(cc2)ccc2N(c(cc2)ccc2-c(cc2)cc3c2[s]c2ccccc32)c(cc2)ccc2N(c2ccccc2)c2ccccc2)=CC1 Chemical compound C1C=CC(N(c(cc2)ccc2-c2ccc(c(cccc3N(c(cc4)ccc4N(c4ccccc4)c4ccccc4)c(cc4)ccc4N(c4ccccc4)c4ccccc4)c3[s]3)c3c2)c(cc2)ccc2N(c(cc2)ccc2-c(cc2)cc3c2[s]c2ccccc32)c(cc2)ccc2N(c2ccccc2)c2ccccc2)=CC1 LOIIPAPIFHZBBZ-UHFFFAOYSA-N 0.000 description 1
- ZDDRYLRMFWMUHD-UHFFFAOYSA-N CC(C1C=CC=CC2C1)=C(C=C)C1=C2C=CCC1 Chemical compound CC(C1C=CC=CC2C1)=C(C=C)C1=C2C=CCC1 ZDDRYLRMFWMUHD-UHFFFAOYSA-N 0.000 description 1
- LZAVFBNHZVPSFI-UHFFFAOYSA-N CC1=C(c2c(C=C=C)c(cccc3)c3[s]2)SC2C=CC=CC12 Chemical compound CC1=C(c2c(C=C=C)c(cccc3)c3[s]2)SC2C=CC=CC12 LZAVFBNHZVPSFI-UHFFFAOYSA-N 0.000 description 1
- PSXSMTQPENMNKW-YWEYNIOJSA-N Cc1c(/C=C\C=C)[s]c2ccccc12 Chemical compound Cc1c(/C=C\C=C)[s]c2ccccc12 PSXSMTQPENMNKW-YWEYNIOJSA-N 0.000 description 1
- PHLOGDWRTZJILM-UHFFFAOYSA-N Cc1ccccc1C1=C(C)C[I]=CC=C1 Chemical compound Cc1ccccc1C1=C(C)C[I]=CC=C1 PHLOGDWRTZJILM-UHFFFAOYSA-N 0.000 description 1
- VDRONIBNVZLDJL-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c1c2[s]c(c(-[n]3c4ccccc4c4ccccc34)ccc3)c3c2ccc1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c1c2[s]c(c(-[n]3c4ccccc4c4ccccc34)ccc3)c3c2ccc1 VDRONIBNVZLDJL-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N c(cc1)cc2c1[s]c1ccccc21 Chemical compound c(cc1)cc2c1[s]c1ccccc21 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- DEWJHKRWEDNBJZ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)cc2c1[s]c1ccccc21)c1cccc2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)cc2c1[s]c1ccccc21)c1cccc2c1cccc2 DEWJHKRWEDNBJZ-UHFFFAOYSA-N 0.000 description 1
- FKFGCHWZQYMRGP-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c(cc1)ccc1-c1cccc2c1[s]c1ccccc21)c(cc1)ccc1N(c1ccccc1)c1ccccc1 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1N(c(cc1)ccc1-c1cccc2c1[s]c1ccccc21)c(cc1)ccc1N(c1ccccc1)c1ccccc1 FKFGCHWZQYMRGP-UHFFFAOYSA-N 0.000 description 1
- BRSOTWFOYHMQHJ-UHFFFAOYSA-N c(cc1c2c3)ccc1[s]c2cc1c3c2ccccc2[s]1 Chemical compound c(cc1c2c3)ccc1[s]c2cc1c3c2ccccc2[s]1 BRSOTWFOYHMQHJ-UHFFFAOYSA-N 0.000 description 1
- LICHBBHMSNSIRT-UHFFFAOYSA-N c1c(-c2cc(-c3ccc(c4ccccc4c4ccccc44)c4c3)ccc2)[s]c2ccccc12 Chemical compound c1c(-c2cc(-c3ccc(c4ccccc4c4ccccc44)c4c3)ccc2)[s]c2ccccc12 LICHBBHMSNSIRT-UHFFFAOYSA-N 0.000 description 1
- SPHALALIDKGHLT-UHFFFAOYSA-N c1ccc2[s]c(c(-c3cccc(-c4c5[s]c6ccccc6c5ccc4)c3)ccc3)c3c2c1 Chemical compound c1ccc2[s]c(c(-c3cccc(-c4c5[s]c6ccccc6c5ccc4)c3)ccc3)c3c2c1 SPHALALIDKGHLT-UHFFFAOYSA-N 0.000 description 1
Classifications
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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, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing three or more hetero rings
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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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
- H10K85/30—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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/348—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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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
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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
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- 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
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- 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
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- 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
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09792929.3A EP2329540B1 (en) | 2008-09-25 | 2009-09-24 | Organoselenium materials and their uses in organic light emitting devices |
CN200980136720.8A CN102160206B (en) | 2008-09-25 | 2009-09-24 | Organoselenium materials and application thereof in organic light emitting devices |
KR1020117005445A KR101678235B1 (en) | 2008-09-25 | 2009-09-24 | Organoselenium materials and their uses in organic light emitting devices |
EP17150393.1A EP3185333B1 (en) | 2008-09-25 | 2009-09-24 | Organoselenium materials and their uses in organic light emitting devices |
JP2011529209A JP5676454B2 (en) | 2008-09-25 | 2009-09-24 | Organic selenium materials and their use in organic light emitting devices |
KR1020167017199A KR101804084B1 (en) | 2008-09-25 | 2009-09-24 | Organoselenium materials and their uses in organic light emitting devices |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10022908P | 2008-09-25 | 2008-09-25 | |
US61/100,229 | 2008-09-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010036765A1 true WO2010036765A1 (en) | 2010-04-01 |
Family
ID=41401827
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2009/058162 WO2010036765A1 (en) | 2008-09-25 | 2009-09-24 | Organoselenium materials and their uses in organic light emitting devices |
Country Status (7)
Country | Link |
---|---|
US (3) | US8426035B2 (en) |
EP (2) | EP3185333B1 (en) |
JP (3) | JP5676454B2 (en) |
KR (2) | KR101804084B1 (en) |
CN (2) | CN102160206B (en) |
TW (3) | TWI541237B (en) |
WO (1) | WO2010036765A1 (en) |
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CN102558168A (en) * | 2010-12-23 | 2012-07-11 | 海洋王照明科技股份有限公司 | Organic semiconductor material and preparation method and application thereof |
WO2013125599A1 (en) | 2012-02-22 | 2013-08-29 | Jnc株式会社 | Novel chalcogen-containing organic compound and use thereof |
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JP2015042632A (en) * | 2013-07-22 | 2015-03-05 | 日本曹達株式会社 | Ruthenium complex |
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JP5815341B2 (en) | 2010-09-09 | 2015-11-17 | 株式会社半導体エネルギー研究所 | Heterocyclic compounds |
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JP5959171B2 (en) * | 2011-09-08 | 2016-08-02 | 国立大学法人名古屋大学 | PI-conjugated organoboron compound and method for producing the same |
US9859517B2 (en) | 2012-09-07 | 2018-01-02 | Nitto Denko Corporation | White organic light-emitting diode |
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US9944846B2 (en) | 2014-08-28 | 2018-04-17 | E I Du Pont De Nemours And Company | Compositions for electronic applications |
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CN104926785B (en) * | 2015-07-06 | 2018-10-09 | 盐城工学院 | A kind of selenium heteroaromatic ring derivative and preparation method thereof |
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Also Published As
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US8426035B2 (en) | 2013-04-23 |
US20130168660A1 (en) | 2013-07-04 |
TW201522324A (en) | 2015-06-16 |
JP6506243B2 (en) | 2019-04-24 |
EP2329540A1 (en) | 2011-06-08 |
JP6067668B2 (en) | 2017-01-25 |
US9455411B2 (en) | 2016-09-27 |
JP2017098556A (en) | 2017-06-01 |
US8945727B2 (en) | 2015-02-03 |
EP3185333A2 (en) | 2017-06-28 |
EP3185333B1 (en) | 2023-09-06 |
KR20160078526A (en) | 2016-07-04 |
CN102160206B (en) | 2014-06-11 |
JP5676454B2 (en) | 2015-02-25 |
CN103094490B (en) | 2016-03-09 |
TW201538493A (en) | 2015-10-16 |
JP2015119186A (en) | 2015-06-25 |
KR101678235B1 (en) | 2016-11-21 |
EP2329540B1 (en) | 2017-01-11 |
CN102160206A (en) | 2011-08-17 |
US20150155499A1 (en) | 2015-06-04 |
KR20110071061A (en) | 2011-06-28 |
TWI628173B (en) | 2018-07-01 |
EP3185333A3 (en) | 2017-10-04 |
JP2012503889A (en) | 2012-02-09 |
CN103094490A (en) | 2013-05-08 |
TWI504596B (en) | 2015-10-21 |
TW201022224A (en) | 2010-06-16 |
KR101804084B1 (en) | 2017-12-01 |
US20100072887A1 (en) | 2010-03-25 |
TWI541237B (en) | 2016-07-11 |
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