CN102099365A - 磷光金属配合化合物、其制备方法和发出辐射的构件 - Google Patents
磷光金属配合化合物、其制备方法和发出辐射的构件 Download PDFInfo
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- CN102099365A CN102099365A CN2009801280967A CN200980128096A CN102099365A CN 102099365 A CN102099365 A CN 102099365A CN 2009801280967 A CN2009801280967 A CN 2009801280967A CN 200980128096 A CN200980128096 A CN 200980128096A CN 102099365 A CN102099365 A CN 102099365A
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- triazole
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- -1 metal complex compound Chemical class 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 150000003852 triazoles Chemical class 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 125000001425 triazolyl group Chemical class 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 150000002390 heteroarenes Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 229910052737 gold Inorganic materials 0.000 claims description 5
- 229910052753 mercury Inorganic materials 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 125000002577 pseudohalo group Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 150000002503 iridium Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229910052738 indium Inorganic materials 0.000 description 9
- 150000000177 1,2,3-triazoles Chemical class 0.000 description 8
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 241000894007 species Species 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000006352 cycloaddition reaction Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 238000006254 arylation reaction Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002739 metals Chemical group 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000005053 phenanthridines Chemical class 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- 150000004941 2-phenylimidazoles Chemical class 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000738322 Homo sapiens Prothymosin alpha Proteins 0.000 description 1
- 241000884009 Hyporhamphus unifasciatus Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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- NNHHYPXRPKNSHG-UHFFFAOYSA-N [In].N1=CC=C(C=C1)C=1N=NN(C1)C1=CC=CC=C1 Chemical compound [In].N1=CC=C(C=C1)C=1N=NN(C1)C1=CC=CC=C1 NNHHYPXRPKNSHG-UHFFFAOYSA-N 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 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
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/90—Assemblies of multiple devices comprising at least one organic light-emitting element
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- H—ELECTRICITY
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- 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
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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
- H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
Claims (17)
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DE102008033929.6 | 2008-07-18 | ||
DE200810033929 DE102008033929A1 (de) | 2008-07-18 | 2008-07-18 | Phosphoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement |
PCT/EP2009/059092 WO2010007107A1 (de) | 2008-07-18 | 2009-07-15 | Phosphoreszente metallkomplexverbindung, verfahren zur herstellung dazu und strahlungsemittierendes bauelement |
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EP (1) | EP2307430B1 (zh) |
JP (1) | JP5653352B2 (zh) |
KR (1) | KR20110040941A (zh) |
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CN105073763A (zh) * | 2013-04-29 | 2015-11-18 | 巴斯夫欧洲公司 | 具有碳烯配体的过渡金属配合物及其在oled中的用途 |
US9200022B2 (en) | 2011-04-15 | 2015-12-01 | Semiconductor Energy Laboratory Co., Ltd. | Organic light-emitting element, organometallic complex, light-emitting device, electronic appliance, and lighting device |
US9768396B2 (en) | 2011-12-23 | 2017-09-19 | Semiconductor Energy Laboratory Co., Ltd. | Iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device |
CN108671961A (zh) * | 2018-05-10 | 2018-10-19 | 三峡大学 | 一种钌配合物光催化剂,制备方法及其应用 |
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JP2013522816A (ja) * | 2010-03-11 | 2013-06-13 | メルク パテント ゲーエムベーハー | 発光ファイバー |
US9005773B2 (en) | 2010-03-15 | 2015-04-14 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, display device, electronic device, and lighting device |
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DE102011104169A1 (de) * | 2011-06-14 | 2012-12-20 | Osram Ag | Strahlungsemittierendes Bauelement und Verfahren zur Herstellung eines strahlungsemittierenden Bauelements |
JP6166557B2 (ja) | 2012-04-20 | 2017-07-19 | 株式会社半導体エネルギー研究所 | 燐光性有機金属イリジウム錯体、発光素子、発光装置、電子機器、および照明装置 |
JP6117618B2 (ja) | 2012-06-01 | 2017-04-19 | 株式会社半導体エネルギー研究所 | 有機金属錯体、発光素子、発光装置、電子機器、及び照明装置 |
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JP7016496B2 (ja) * | 2017-10-03 | 2022-02-07 | 学校法人神奈川大学 | パラジウム錯体固体、錯体触媒、及びそれらの製造方法 |
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US9200022B2 (en) | 2011-04-15 | 2015-12-01 | Semiconductor Energy Laboratory Co., Ltd. | Organic light-emitting element, organometallic complex, light-emitting device, electronic appliance, and lighting device |
US9768396B2 (en) | 2011-12-23 | 2017-09-19 | Semiconductor Energy Laboratory Co., Ltd. | Iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device |
CN105073763A (zh) * | 2013-04-29 | 2015-11-18 | 巴斯夫欧洲公司 | 具有碳烯配体的过渡金属配合物及其在oled中的用途 |
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CN105073763B (zh) * | 2013-04-29 | 2019-03-01 | Udc 爱尔兰有限责任公司 | 具有碳烯配体的过渡金属配合物及其在oled中的用途 |
CN108671961A (zh) * | 2018-05-10 | 2018-10-19 | 三峡大学 | 一种钌配合物光催化剂,制备方法及其应用 |
CN108671961B (zh) * | 2018-05-10 | 2021-01-26 | 三峡大学 | 一种钌配合物光催化剂,制备方法及其应用 |
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EP2307430B1 (de) | 2014-08-27 |
DE102008033929A1 (de) | 2010-01-21 |
JP5653352B2 (ja) | 2015-01-14 |
EP2307430A1 (de) | 2011-04-13 |
KR20110040941A (ko) | 2011-04-20 |
CN102099365B (zh) | 2015-05-13 |
JP2011528328A (ja) | 2011-11-17 |
WO2010007107A1 (de) | 2010-01-21 |
US20110187265A1 (en) | 2011-08-04 |
US9012038B2 (en) | 2015-04-21 |
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