JP7458483B2 - 金属錯体及びその用途 - Google Patents
金属錯体及びその用途 Download PDFInfo
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- JP7458483B2 JP7458483B2 JP2022531550A JP2022531550A JP7458483B2 JP 7458483 B2 JP7458483 B2 JP 7458483B2 JP 2022531550 A JP2022531550 A JP 2022531550A JP 2022531550 A JP2022531550 A JP 2022531550A JP 7458483 B2 JP7458483 B2 JP 7458483B2
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- carbon atoms
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- 229910052751 metal Inorganic materials 0.000 title description 9
- 239000002184 metal Substances 0.000 title description 9
- 239000010410 layer Substances 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 150000004696 coordination complex Chemical class 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000013086 organic photovoltaic Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 230000005693 optoelectronics Effects 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 238000007740 vapor deposition Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001308 synthesis method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000006862 quantum yield reaction Methods 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QOLHWXNSCZGWHK-BWBORTOCSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-(11-phenoxyundecylcarbamoyloxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@@H]([C@@H](OC(=O)NCCCCCCCCCCCOC=3C=CC=CC=3)C(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O)O)C1=CC=CC=C1 QOLHWXNSCZGWHK-BWBORTOCSA-N 0.000 description 2
- MOQCFMZWVKQBAP-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)benzoyl]-n-(4-chlorophenyl)piperidine-3-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2CC(CCC2)C(=O)NC=2C=CC(Cl)=CC=2)=C1 MOQCFMZWVKQBAP-UHFFFAOYSA-N 0.000 description 2
- AKBHYCHPWZPGAH-UHFFFAOYSA-N 2-[3-[(3-chloro-4-methylphenyl)methoxy]azetidine-1-carbonyl]-7-oxa-5-azaspiro[3.4]octan-6-one Chemical compound CC1=C(Cl)C=C(COC2CN(C2)C(=O)C2CC3(C2)COC(=O)N3)C=C1 AKBHYCHPWZPGAH-UHFFFAOYSA-N 0.000 description 2
- MVXAKOGJWVQPKC-UHFFFAOYSA-N 5-(3-ethynyl-5-fluorophenyl)-2-pyridin-2-yl-4,6,7,8-tetrahydro-[1,3]oxazolo[4,5-c]azepine Chemical compound FC1=CC(C#C)=CC(N2CC=3N=C(OC=3CCC2)C=2N=CC=CC=2)=C1 MVXAKOGJWVQPKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229940126559 Compound 4e Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 239000011365 complex material Substances 0.000 description 2
- 229940126115 compound 4f Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- YDMRDHQUQIVWBE-UHFFFAOYSA-N (2-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1O YDMRDHQUQIVWBE-UHFFFAOYSA-N 0.000 description 1
- PNHBRYIAJCYNDA-VQCQRNETSA-N (4r)-6-[2-[2-ethyl-4-(4-fluorophenyl)-6-phenylpyridin-3-yl]ethyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1CCC=1C(CC)=NC(C=2C=CC=CC=2)=CC=1C1=CC=C(F)C=C1 PNHBRYIAJCYNDA-VQCQRNETSA-N 0.000 description 1
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229940125907 SJ995973 Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125872 compound 4d Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XZMHJYWMCRQSSI-UHFFFAOYSA-N n-[5-[2-(3-acetylanilino)-1,3-thiazol-4-yl]-4-methyl-1,3-thiazol-2-yl]benzamide Chemical compound CC(=O)C1=CC=CC(NC=2SC=C(N=2)C2=C(N=C(NC(=O)C=3C=CC=CC=3)S2)C)=C1 XZMHJYWMCRQSSI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
Classifications
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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
- C07F15/0086—Platinum compounds
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/10—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 two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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]
- H10K50/11—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
- 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
- H10K85/30—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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Description
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12及びR13はそれぞれ、独立して、水素、重水素、ハロゲン、1~20個の炭素原子を有する置換又は非置換のアルキル基、置換又は非置換の3~20個の炭素原子を有するシクロアルキル基、置換又は非置換の1~20個の炭素原子を有するアルコキシ基、置換又は非置換の6~30個の炭素原子を有するアリール基、置換又は非置換の3~30個の炭素原子を有するヘテロアリール基、又はシアノ基から選択され、
Ar1は、少なくとも2個のN原子及び3~30個の炭素原子を含むヘテロ芳香族基であり、Ar2及びAr3はそれぞれ、独立して、3~30個の炭素原子の芳香族基又はヘテロ芳香族基から選択され、前記ヘテロ芳香族基におけるヘテロ原子は、N、S、O原子から選択され、
前記置換は、重水素、ハロゲン又は1~8個の炭素原子のアルキル基による置換である。
前記置換は、重水素又は1~4個の炭素原子のアルキル基による置換である。
以下の式の化合物の原料はすべて市販されている。
〈実施例1〉
化合物4a(3.5g、19.2mmol)、化合4b(4.6g、23.0mmol)、酢酸パラジウム(0.4g、0.2mmol)及びCsF(3.0g、20.0mmol)を、トリフルオロメタンスルホン酸(10mL)と水(30mL)の混合溶液に溶解し、60℃に加熱し、8時間反応させた。室温まで冷却した後、上記の反応液を水に入れ、ジクロロメタンで3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去し、残留物をカラムクロマトグラフィーにより分離して、白色固体を取得した(4.7g、収率71%)。ESI-MS(m/z):339.9(M+1)。備考:反応をスケールアップすると、反応収率が大幅に低下した。
窒素の保護下で、化合物4c(17.0g、50.0mmol)をテトラヒドロフラン(100mL)に溶解し、-78℃まで冷却し、n-ブチルリチウムBuLi(1.2eq)を滴下し、30分間撹拌した後、化合物4d(17.3g、50.0mmol)のテトラヒドロフラン溶液(30mL)を上記の溶液に滴下し、30分間撹拌した後、室温まで加熱し、1時間撹拌し続けた。上記の反応液を水に入れ、ジクロロメタンで3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去して、淡黄色固体を取得した。上記の固体を酢酸(50mL)に溶解し、濃硫酸(4mL)を添加し、窒素の保護下で、一晩還流した。室温まで冷却した後、上記の反応液を水に入れ、ジクロロメタンで3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去し、残留物をカラムクロマトグラフィーにより分離して、淡黄色固体を取得した(18.6g、収率63%)。ESI-MS(m/z):588.1(M+1)。
窒素の保護下で、化合物4e(5.9g、10.0mmol)、O-ヒドロキシフェニルボロン酸(1.6g、12.0mmol)、Pd(PPh3)4(0.6g、0.5mmol)、K2CO3(4.0g、30.0mmol)、テトラヒドロフラン(50mL)及び水(5mL)を順にシュレンクチューブに入れた。80℃に加熱し、24時間反応させた。室温まで冷却した後、上記の反応液を水に入れ、ジクロロメタンで3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去し、残留物をカラムクロマトグラフィーにより分離して、灰白色固体を取得した(4.9g、収率81%)。ESI-MS(m/z):600.2(M-1)。
窒素の保護下で、化合物4f(4.9g、8.1mmol)、ビス(ピナコラート)ジボロン(37mmolmmol、10.0mmol)、酢酸カリウム(2.5g、25.0mmol)、Pd(dppf)Cl2(0.3g、0.4mmol)をジオキサン(50mL)に溶解し、窒素で数回置換した後、一晩加熱還流し反応させた。室温まで冷却した後、上記の反応液を水に入れ、酢酸エチルで3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去し、残留物をカラムクロマトグラフィーにより分離して、灰白色固体を取得した(4.5g、収率85%)。ESI-MS(m/z):648.4(M-1)。
窒素の保護下で、化合物4g(4.2g、6.5mmol)、クロル-s-トリアジン(1.0g、8.5mmol)、Pd(PPh3)4(0.3g、0.3mmol)、K2CO3(1.3g、10.0mmol)、テトラヒドロフラン(30mL)及び水(5mL)を順にシュレンクチューブに入れた。80℃に加熱し、24時間反応させた。室温まで冷却した後、上記の反応液を水に入れ、ジクロロメタンで3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去し、残留物をカラムクロマトグラフィーにより分離して、淡黄色固体を取得した(2.4g、収率62%)。ESI-MS(m/z):601.3(M-1)。
化合物4h(2.0g、3.3mmol)、塩化白全酸カリウム(1.7g、4.0mmol)及び250mL酢酸をフラスコに入れ、窒素の保護下で、48時間還流撹拌した。室温まで冷却した後、上記の反応液を水に入れ、濾過して粗生成物を取得し、再結晶して赤色固体を取得した(2.4g、収率90%)。ESI-MS(m/z):796.3(M+1)。
〈実施例2〉
中間体クロル-s-トリアジンを中間体29aに置き換え、化合物4hの合成方法を参照して化合物29bを調製し、淡黄色固体を取得した(3.2g、収率70%)。ESI-MS(m/z):650.3(M-1)。
中間体4hを中間体29bに置き換え、錯体4の合成方法を参照して化合物錯体29を調製し、赤色固体を取得した(2.9g、収率85%)。ESI-MS(m/z):845.3(M+1)。
〈実施例3〉
中間体クロル-s-トリアジンを中間体32aに置き換え、化合物4hの合成方法を参照して化合物32bを調製し、淡黄色固体を取得した(2.1g、収率55%)。ESI-MS(m/z):639.3(M-1)。
中間体4hを中間体32bに置き換え、錯体4の合成方法を参照して化合物錯体32を調製し、赤色固体を取得した(2.3g、収率81%)。ESI-MS(m/z):834.3(M+1)。
〈実施例4〉
中間体クロル-s-トリアジンを中間体32aに置き換え、化合物4hの合成方法を参照して化合物32bを調製し、淡黄色固体を取得した(2.1g、収率55%)。ESI-MS(m/z):700.3(M-1)。
中間体4hを中間体36bに置き換え、錯体4の合成方法を参照して化合物錯体36を調製し、深赤色固体を取得した(1.9g、収率65%)。ESI-MS(m/z):895.5(M+1)。
〈実施例5〉
中間体クロル-s-トリアジンを中間体54aに置き換え、化合物4hの合成方法を参照して化合物54bを調製し、淡黄色固体を取得した(3.5g、収率69%)。ESI-MS(m/z):664.4(M-1)。
中間体4hを中間体54bに置き換え、錯体4の合成方法を参照して化合物錯体54を調製し、赤色固体を取得した(1.3g、収率81%)。ESI-MS(m/z):859.2(M+1)。
〈実施例6~10〉
〈比較例1〉
〈実施例11〉
Claims (10)
- 式(I)の構造を有する金属錯体であり、
式(I)中、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12及びR13はそれぞれ、独立して、水素、重水素、ハロゲン、1~20個の炭素原子を有する置換もしくは非置換のアルキル基、3~20個の炭素原子を有する置換もしくは非置換のシクロアルキル基、1~20個の炭素原子を有する置換もしくは非置換のアルコキシ基、6~30個の炭素原子を有する置換もしくは非置換のアリール基、及び3~30個の炭素原子を有する置換もしくは非置換のヘテロアリール基又はシアノ基から選択され、
Ar1は、以下に示すHA4、HA9、HA10、HA12及びHA18のうちから選択され、Ar2及びAr3はベンゼンであり、
前記置換は、重水素、ハロゲン又は1~8個の炭素原子のアルキル基による置換である、ことを特徴とする金属錯体。 - 前記式(I)中、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12及びR13はそれぞれ、水素、重水素、ハロゲン、1~6個の炭素原子を有する置換もしくは非置換のアルキル基、3~6個の炭素原子を有する置換もしくは非置換のシクロアルキル基、1~6個の炭素原子を有する置換もしくは非置換のアルコキシ基、6~12個の炭素原子を有する置換もしくは非置換のアリール基、3~12個の炭素原子を有する置換もしくは非置換のヘテロアリール基又はシアノ基から選択され、
前記置換は、重水素又は1~4個の炭素原子のアルキル基による置換である、ことを特徴とする請求項1に記載の金属錯体。 - 前記式(I)中、R2、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12及びR13はそれぞれ、水素、重水素、1~4個の炭素原子を有する置換もしくは非置換のアルキル基、又は3~6個の炭素原子を有する置換もしくは非置換のシクロアルキル基から選択される、ことを特徴とする請求項2に記載の金属錯体。
- R1、R2、R3、R4、R5、R6、R7、R8、R9及びR10は水素である、ことを特徴とする請求項3に記載の金属錯体。
- 以下のうちのいずれかの構造を有する、ことを特徴とする請求項1に記載の金属錯体。
- 以下の構造を有する、ことを特徴とする請求項1~5のいずれか一項に記載の金属錯体のリガンド。
- 有機光電子デバイスにおける請求項1~5のいずれか一項に記載の金属錯体の使用であって、前記有機光電子デバイスは、有機エレクトロルミネセンスデバイス、有機薄膜トランジスタ、有機光起電力デバイス、発光電気化学セル及び化学センサを含む、ことを特徴とする使用。
- 陰極、陽極及び有機層を含み、前記有機層は、正孔注入層、正孔輸送層、発光層、正孔阻止層、電子注入層及び電子輸送層のうちの1つ又は複数の層を有し、前記有機層は、請求項1~5のいずれか一項に記載の金属錯体を含む、ことを特徴とする有機エレクトロルミネセンスデバイス。
- 請求項1~5のいずれか一項に記載の金属錯体は、発光層又は電子輸送層に用いられる、ことを特徴とする請求項8に記載の有機エレクトロルミネセンスデバイス。
- 前記有機層の総厚さは1~1000nmであり、前記有機層は、蒸着又は溶液法によって薄膜に形成されたものである、ことを特徴とする請求項8に記載の有機エレクトロルミネセンスデバイス。
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JP2006093542A (ja) | 2004-09-27 | 2006-04-06 | Fuji Photo Film Co Ltd | 発光素子 |
JP2006232784A (ja) | 2005-02-28 | 2006-09-07 | Takasago Internatl Corp | 白金錯体及び発光素子 |
JP2013023500A (ja) | 2011-07-25 | 2013-02-04 | Universal Display Corp | 四座配位白金錯体 |
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