WO2023170880A1 - Composé dicarbazolyl-benzène et dispositif électroluminescent organique - Google Patents
Composé dicarbazolyl-benzène et dispositif électroluminescent organique Download PDFInfo
- Publication number
- WO2023170880A1 WO2023170880A1 PCT/JP2022/010682 JP2022010682W WO2023170880A1 WO 2023170880 A1 WO2023170880 A1 WO 2023170880A1 JP 2022010682 W JP2022010682 W JP 2022010682W WO 2023170880 A1 WO2023170880 A1 WO 2023170880A1
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- WO
- WIPO (PCT)
- Prior art keywords
- group
- dicarbazolyl
- substituted
- groups
- dicarbazolylbenzene
- Prior art date
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- -1 Dicarbazolyl benzene compound Chemical class 0.000 title claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
- 125000000524 functional group Chemical group 0.000 claims abstract description 17
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 14
- BODVWELZYMTBLU-UHFFFAOYSA-N 1-[2-(9h-carbazol-1-yl)phenyl]-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 BODVWELZYMTBLU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 18
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 description 56
- 239000010410 layer Substances 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 30
- 239000000463 material Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 235000013619 trace mineral Nutrition 0.000 description 11
- 239000011573 trace mineral Substances 0.000 description 11
- 239000005416 organic matter Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 8
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 5
- 150000001499 aryl bromides Chemical class 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- ZKGHGKNHPPZALY-UHFFFAOYSA-N 9-(3-bromophenyl)carbazole Chemical compound BrC1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 ZKGHGKNHPPZALY-UHFFFAOYSA-N 0.000 description 2
- NSXJEEMTGWMJPY-UHFFFAOYSA-N 9-[3-(3-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 NSXJEEMTGWMJPY-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- VBQIVFTUXFKGKW-UHFFFAOYSA-N n-[4-(4-bromophenyl)phenyl]-4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 VBQIVFTUXFKGKW-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- LPLLWKZDMKTEMV-UHFFFAOYSA-N 1-bromo-3-(3-bromophenyl)benzene Chemical group BrC1=CC=CC(C=2C=C(Br)C=CC=2)=C1 LPLLWKZDMKTEMV-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- YXHXRBIAIVNCPG-UHFFFAOYSA-N 9-(3,5-dibromophenyl)carbazole Chemical compound BrC1=CC(Br)=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 YXHXRBIAIVNCPG-UHFFFAOYSA-N 0.000 description 1
- SJOKONNBSXFPSN-UHFFFAOYSA-N 9-(3-bromo-5-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC(Br)=C1 SJOKONNBSXFPSN-UHFFFAOYSA-N 0.000 description 1
- YJEUUQOJSFGEQT-UHFFFAOYSA-N 9-(3-bromophenyl)-3,6-diphenylcarbazole Chemical compound BrC1=CC=CC(N2C3=CC=C(C=C3C3=CC(=CC=C32)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YJEUUQOJSFGEQT-UHFFFAOYSA-N 0.000 description 1
- WOOAKXXQTAVKGL-UHFFFAOYSA-N 9-(4-bromophenyl)-3,6-diphenylcarbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=C(C=3C=CC=CC=3)C=C2C2=CC(C=3C=CC=CC=3)=CC=C21 WOOAKXXQTAVKGL-UHFFFAOYSA-N 0.000 description 1
- CLGDYJYGBMTANB-UHFFFAOYSA-N 9-[4-(4-bromophenyl)phenyl]-3,6-diphenylcarbazole Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)C1=CC=CC=C1)C1=CC=CC=C1 CLGDYJYGBMTANB-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BTFIECQCKYNJTN-UHFFFAOYSA-N n-(4-bromophenyl)-4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 BTFIECQCKYNJTN-UHFFFAOYSA-N 0.000 description 1
- VKUGPCCUCHYUFE-UHFFFAOYSA-N n-(4-bromophenyl)-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC(Br)=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=CC=C2)C2=C1 VKUGPCCUCHYUFE-UHFFFAOYSA-N 0.000 description 1
- XUTVUTNJPNJUIK-UHFFFAOYSA-N n-[4-(4-bromophenyl)phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=C3C=CC=CC3=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 XUTVUTNJPNJUIK-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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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
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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
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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
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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
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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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
- H10K85/633—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
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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
- H10K85/657—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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- Chemical & Material Sciences (AREA)
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- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Indole Compounds (AREA)
Abstract
Ce composé dicarbazolyl-benzène comprend au moins un groupe dicarbazolyle dans lequel deux groupes carbazolyle sont liés l'un à l'autre ou au moins un groupe dicarbazolyle substituant auquel au moins un groupe fonctionnel est lié. Le composé dicarbazolyl-benzène comprend, en tant que squelette de base de celui-ci, un dicarbazolyl-benzène dans lequel le groupes dicarbazolyle et/ou ledit au moins un groupe dicarbazolyle substituant est lié à un cycle benzène. Le composé dicarbazolyl-benzène présente la structure représentée par la formule développée (1).
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2022/010682 WO2023170880A1 (fr) | 2022-03-10 | 2022-03-10 | Composé dicarbazolyl-benzène et dispositif électroluminescent organique |
JP2023562803A JP7445249B2 (ja) | 2022-03-10 | 2023-03-09 | ジカルバゾリル類化合物及び有機エレクトロルミネッセンス素子 |
PCT/JP2023/009107 WO2023171761A1 (fr) | 2022-03-10 | 2023-03-09 | Composé dicarbazolyle et élément électroluminescent organique |
KR1020247002001A KR20240023619A (ko) | 2022-03-10 | 2023-03-09 | 디카르바졸릴류 화합물 및 유기전계발광소자 |
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PCT/JP2022/010682 WO2023170880A1 (fr) | 2022-03-10 | 2022-03-10 | Composé dicarbazolyl-benzène et dispositif électroluminescent organique |
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Publication Number | Publication Date |
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WO2023170880A1 true WO2023170880A1 (fr) | 2023-09-14 |
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PCT/JP2022/010682 WO2023170880A1 (fr) | 2022-03-10 | 2022-03-10 | Composé dicarbazolyl-benzène et dispositif électroluminescent organique |
PCT/JP2023/009107 WO2023171761A1 (fr) | 2022-03-10 | 2023-03-09 | Composé dicarbazolyle et élément électroluminescent organique |
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PCT/JP2023/009107 WO2023171761A1 (fr) | 2022-03-10 | 2023-03-09 | Composé dicarbazolyle et élément électroluminescent organique |
Country Status (3)
Country | Link |
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JP (1) | JP7445249B2 (fr) |
KR (1) | KR20240023619A (fr) |
WO (2) | WO2023170880A1 (fr) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2011049325A2 (fr) * | 2009-10-21 | 2011-04-28 | Cheil Industries Inc. | Nouveau composé pour dispositif photoélectrique organique et dispositif photoélectrique organique le comprenant |
WO2011081061A1 (fr) * | 2009-12-28 | 2011-07-07 | 新日鐵化学株式会社 | Elément électroluminescent organique |
WO2013161437A1 (fr) * | 2012-04-25 | 2013-10-31 | 国立大学法人九州大学 | Matériau électroluminescent et élément électroluminescent organique |
KR20140141337A (ko) * | 2013-05-31 | 2014-12-10 | 제일모직주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
KR20180062208A (ko) * | 2016-11-30 | 2018-06-08 | 희성소재 (주) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
KR20200078253A (ko) * | 2018-12-21 | 2020-07-01 | 솔브레인 주식회사 | 헤테로고리 화합물 및 이를 포함한 유기 발광 소자 |
KR20200122252A (ko) * | 2019-04-17 | 2020-10-27 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
US20210210700A1 (en) * | 2018-11-28 | 2021-07-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
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DE102010012738A1 (de) * | 2010-03-25 | 2011-09-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
KR101512059B1 (ko) * | 2014-10-06 | 2015-04-14 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR102591635B1 (ko) * | 2015-10-27 | 2023-10-20 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
CN110452153A (zh) * | 2018-05-08 | 2019-11-15 | 北京鼎材科技有限公司 | 有机电致发光材料与器件 |
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US20220177492A1 (en) * | 2019-10-25 | 2022-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20220054483A (ko) * | 2020-10-23 | 2022-05-03 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN114621237B (zh) * | 2020-12-14 | 2023-12-05 | 广州华睿光电材料有限公司 | 有机化合物、混合物、组合物及有机电子器件 |
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- 2022-03-10 WO PCT/JP2022/010682 patent/WO2023170880A1/fr unknown
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- 2023-03-09 WO PCT/JP2023/009107 patent/WO2023171761A1/fr active Application Filing
- 2023-03-09 KR KR1020247002001A patent/KR20240023619A/ko active Search and Examination
- 2023-03-09 JP JP2023562803A patent/JP7445249B2/ja active Active
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WO2011081061A1 (fr) * | 2009-12-28 | 2011-07-07 | 新日鐵化学株式会社 | Elément électroluminescent organique |
WO2013161437A1 (fr) * | 2012-04-25 | 2013-10-31 | 国立大学法人九州大学 | Matériau électroluminescent et élément électroluminescent organique |
KR20140141337A (ko) * | 2013-05-31 | 2014-12-10 | 제일모직주식회사 | 유기 화합물, 유기 광전자 소자 및 표시 장치 |
KR20180062208A (ko) * | 2016-11-30 | 2018-06-08 | 희성소재 (주) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
US20210210700A1 (en) * | 2018-11-28 | 2021-07-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20200078253A (ko) * | 2018-12-21 | 2020-07-01 | 솔브레인 주식회사 | 헤테로고리 화합물 및 이를 포함한 유기 발광 소자 |
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KR20240023619A (ko) | 2024-02-22 |
JP7445249B2 (ja) | 2024-03-07 |
WO2023171761A1 (fr) | 2023-09-14 |
JPWO2023171761A1 (fr) | 2023-09-14 |
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