WO2019022546A1 - 지연 형광 재료 및 이를 포함하는 유기 발광 소자 - Google Patents
지연 형광 재료 및 이를 포함하는 유기 발광 소자 Download PDFInfo
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- WO2019022546A1 WO2019022546A1 PCT/KR2018/008494 KR2018008494W WO2019022546A1 WO 2019022546 A1 WO2019022546 A1 WO 2019022546A1 KR 2018008494 W KR2018008494 W KR 2018008494W WO 2019022546 A1 WO2019022546 A1 WO 2019022546A1
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- NJVSFOMTEFOHMI-UHFFFAOYSA-N n,2-diphenylaniline Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1NC1=CC=CC=C1 NJVSFOMTEFOHMI-UHFFFAOYSA-N 0.000 description 1
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- HCISEFFYVMEPNF-UHFFFAOYSA-N n-phenyl-9h-fluoren-1-amine Chemical group C=12CC3=CC=CC=C3C2=CC=CC=1NC1=CC=CC=C1 HCISEFFYVMEPNF-UHFFFAOYSA-N 0.000 description 1
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- CSHWQDPOILHKBI-UHFFFAOYSA-N perylene Chemical compound C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
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- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
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- 230000008569 process Effects 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
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- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
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- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- 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
-
- 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
- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
Definitions
- An organic light emitting device using a retardation fluorescent material composed of a compound represented by Chemical Formula 1 according to one embodiment of the present invention can improve efficiency, improve driving voltage and / or lifetime characteristics.
- amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluor
- the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
- the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.
- R 1 through R 14 are the same as defined in Formula 1.
- the light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, At least one of the excitation light energy and the excitation triplet energy has a higher value than that of the light emitting material of the retardation fluorescent material and has a hole transporting ability and an electron transporting ability, Can be prevented, and an organic compound having a high glass transition temperature can be included as a host.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
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| CN201880026808.3A CN110621760B (zh) | 2017-07-27 | 2018-07-27 | 延迟荧光材料及包含其的有机发光材料 |
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| KR10-2017-0095434 | 2017-07-27 | ||
| KR20170095434 | 2017-07-27 |
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| WO2019022546A1 true WO2019022546A1 (ko) | 2019-01-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/KR2018/008494 WO2019022546A1 (ko) | 2017-07-27 | 2018-07-27 | 지연 형광 재료 및 이를 포함하는 유기 발광 소자 |
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| Country | Link |
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| KR (1) | KR102068415B1 (zh) |
| CN (1) | CN110621760B (zh) |
| WO (1) | WO2019022546A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2019078700A1 (ko) * | 2017-10-20 | 2019-04-25 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
| KR102534666B1 (ko) * | 2017-11-30 | 2023-05-18 | 엘지디스플레이 주식회사 | 유기 화합물과 이를 포함하는 유기발광다이오드 및 유기발광 표시장치 |
| KR20210046258A (ko) * | 2019-10-18 | 2021-04-28 | 엘지디스플레이 주식회사 | 유기발광다이오드 및 유기발광장치 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140001446A1 (en) * | 2011-12-05 | 2014-01-02 | Yumiko Mizuki | Material for organic electroluminescence device and organic electroluminescence device |
| KR20140003737A (ko) * | 2012-06-26 | 2014-01-10 | 롬엔드하스전자재료코리아유한회사 | 발광층 및 이를 포함하는 유기 전계 발광 소자 |
| US20140231769A1 (en) * | 2013-02-15 | 2014-08-21 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and electronic device |
| KR20150045295A (ko) * | 2013-10-18 | 2015-04-28 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
| KR20150116776A (ko) * | 2014-04-08 | 2015-10-16 | 롬엔드하스전자재료코리아유한회사 | 복수종의 호스트 재료와 이를 포함하는 유기 전계 발광 소자 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101547065B1 (ko) * | 2013-07-29 | 2015-08-25 | 주식회사 엘지화학 | 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자 |
| KR20150085772A (ko) * | 2014-01-16 | 2015-07-24 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
-
2018
- 2018-07-27 KR KR1020180087817A patent/KR102068415B1/ko active IP Right Grant
- 2018-07-27 WO PCT/KR2018/008494 patent/WO2019022546A1/ko active Application Filing
- 2018-07-27 CN CN201880026808.3A patent/CN110621760B/zh active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140001446A1 (en) * | 2011-12-05 | 2014-01-02 | Yumiko Mizuki | Material for organic electroluminescence device and organic electroluminescence device |
| KR20140003737A (ko) * | 2012-06-26 | 2014-01-10 | 롬엔드하스전자재료코리아유한회사 | 발광층 및 이를 포함하는 유기 전계 발광 소자 |
| US20140231769A1 (en) * | 2013-02-15 | 2014-08-21 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and electronic device |
| KR20150045295A (ko) * | 2013-10-18 | 2015-04-28 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
| KR20150116776A (ko) * | 2014-04-08 | 2015-10-16 | 롬엔드하스전자재료코리아유한회사 | 복수종의 호스트 재료와 이를 포함하는 유기 전계 발광 소자 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102068415B1 (ko) | 2020-01-20 |
| CN110621760B (zh) | 2023-04-04 |
| CN110621760A (zh) | 2019-12-27 |
| KR20190013603A (ko) | 2019-02-11 |
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