KR20180067641A - 헤테로 고리 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 - Google Patents
헤테로 고리 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 Download PDFInfo
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- KR20180067641A KR20180067641A KR1020187013529A KR20187013529A KR20180067641A KR 20180067641 A KR20180067641 A KR 20180067641A KR 1020187013529 A KR1020187013529 A KR 1020187013529A KR 20187013529 A KR20187013529 A KR 20187013529A KR 20180067641 A KR20180067641 A KR 20180067641A
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- KR
- South Korea
- Prior art keywords
- light emitting
- general formula
- group
- heterocyclic compound
- carbon atoms
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 245
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 143
- -1 dibenzofuranyl group Chemical group 0.000 claims abstract description 123
- 125000000732 arylene group Chemical group 0.000 claims abstract description 73
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 53
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims abstract description 40
- 125000001424 substituent group Chemical group 0.000 claims abstract description 38
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims description 231
- 150000001875 compounds Chemical class 0.000 claims description 133
- 239000000758 substrate Substances 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 58
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 31
- 239000001301 oxygen Substances 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 239000011593 sulfur Substances 0.000 claims description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 29
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical group C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 claims description 22
- 230000005525 hole transport Effects 0.000 claims description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- 125000006836 terphenylene group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract description 17
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- 238000000862 absorption spectrum Methods 0.000 description 38
- 238000005259 measurement Methods 0.000 description 38
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- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 34
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- 239000011159 matrix material Substances 0.000 description 20
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 15
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 15
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- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 13
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
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- 230000005281 excited state Effects 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 125000005595 acetylacetonate group Chemical group 0.000 description 11
- 238000004040 coloring Methods 0.000 description 11
- 238000000605 extraction Methods 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
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- 238000002189 fluorescence spectrum Methods 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000003086 colorant Substances 0.000 description 9
- 229910003437 indium oxide Inorganic materials 0.000 description 9
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 9
- 239000011787 zinc oxide Substances 0.000 description 9
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 8
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 238000005092 sublimation method Methods 0.000 description 8
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 7
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 5
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 5
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- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
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- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 3
- XUKACIDLJPTDTL-UHFFFAOYSA-N (4-dibenzothiophen-4-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=C1SC1=CC=CC=C12 XUKACIDLJPTDTL-UHFFFAOYSA-N 0.000 description 3
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- 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
- C07D403/10—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 linked by a carbon chain containing aromatic rings
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- C07D405/10—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 two hetero rings linked by a carbon chain containing aromatic rings
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- Microelectronics & Electronic Packaging (AREA)
- Electroluminescent Light Sources (AREA)
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| PCT/IB2016/056067 WO2017068457A1 (en) | 2015-10-23 | 2016-10-11 | Heterocyclic compound, light-emitting element, light-emitting device, electronic device, and lighting device |
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| JP6640034B2 (ja) * | 2016-06-17 | 2020-02-05 | 株式会社ジャパンディスプレイ | 有機el表示装置の製造方法 |
| CN108681619B (zh) * | 2018-04-03 | 2022-03-04 | 哈尔滨工业大学 | 方形软包锂离子电池热物性参数辨识方法 |
| US12501828B2 (en) | 2018-12-28 | 2025-12-16 | Samsung Electronics Co., Ltd. | Organic light-emitting device and apparatus including the same |
| EP3674295A1 (en) | 2018-12-28 | 2020-07-01 | Samsung Electronics Co., Ltd. | Heterocyclic compound, composition including heterocyclic compound, and organic light-emitting device including heterocyclic compound |
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| ES2303329T3 (es) | 2005-02-16 | 2008-08-01 | Dielectric Laboratories, Inc. | Resonador discreto sintonizable en tension, fabricado de material dielectrico. |
| JP5631559B2 (ja) | 2008-05-16 | 2014-11-26 | 株式会社半導体エネルギー研究所 | 芳香族アミン化合物および発光素子 |
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| JP6253971B2 (ja) | 2012-12-28 | 2017-12-27 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、及び照明装置 |
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| KR102307287B1 (ko) | 2013-08-30 | 2021-09-29 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
| WO2015105313A1 (ko) * | 2014-01-10 | 2015-07-16 | 삼성에스디아이 주식회사 | 축합환 화합물, 및 이를 포함한 유기 발광 소자 |
| KR101846436B1 (ko) | 2014-01-29 | 2018-04-06 | 제일모직 주식회사 | 전자수송보조층용 조성물, 전자수송보조층을 포함하는 유기 광전자 소자 및 표시 장치 |
| JP6530227B2 (ja) * | 2014-04-25 | 2019-06-12 | 株式会社半導体エネルギー研究所 | 化合物、発光素子、発光装置、電子機器、及び照明装置 |
| JP2015227328A (ja) | 2014-05-02 | 2015-12-17 | 株式会社半導体エネルギー研究所 | 化合物、発光素子、発光装置、電子機器、及び照明装置 |
| JP6780925B2 (ja) * | 2014-07-25 | 2020-11-04 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器及び照明装置 |
| KR101842584B1 (ko) * | 2015-02-13 | 2018-03-27 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치 |
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2016
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- 2016-10-11 CN CN201680061311.6A patent/CN108137565B/zh active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2007189001A (ja) | 2006-01-12 | 2007-07-26 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
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| KR20240094035A (ko) | 2024-06-24 |
| JP6817023B2 (ja) | 2021-01-20 |
| US11522138B2 (en) | 2022-12-06 |
| TWI762453B (zh) | 2022-05-01 |
| WO2017068457A1 (en) | 2017-04-27 |
| JP2017081909A (ja) | 2017-05-18 |
| CN108137565B (zh) | 2022-03-08 |
| JP2021073683A (ja) | 2021-05-13 |
| CN114436940B (zh) | 2025-03-28 |
| JP2022088388A (ja) | 2022-06-14 |
| JP7274632B2 (ja) | 2023-05-16 |
| TW201728580A (zh) | 2017-08-16 |
| US20170117487A1 (en) | 2017-04-27 |
| CN108137565A (zh) | 2018-06-08 |
| JP7035159B2 (ja) | 2022-03-14 |
| CN114436940A (zh) | 2022-05-06 |
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