JPWO2012039347A1 - 金属錯体、発光素子、表示装置 - Google Patents
金属錯体、発光素子、表示装置 Download PDFInfo
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- JPWO2012039347A1 JPWO2012039347A1 JP2012535017A JP2012535017A JPWO2012039347A1 JP WO2012039347 A1 JPWO2012039347 A1 JP WO2012039347A1 JP 2012535017 A JP2012535017 A JP 2012535017A JP 2012535017 A JP2012535017 A JP 2012535017A JP WO2012039347 A1 JPWO2012039347 A1 JP WO2012039347A1
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 189
- 150000001768 cations Chemical class 0.000 claims abstract description 25
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 71
- HKOAFLAGUQUJQG-UHFFFAOYSA-N 2-pyrimidin-2-ylpyrimidine Chemical compound N1=CC=CN=C1C1=NC=CC=N1 HKOAFLAGUQUJQG-UHFFFAOYSA-N 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000001450 anions Chemical class 0.000 claims description 27
- -1 hydrogen ions Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910017489 Cu I Inorganic materials 0.000 claims description 8
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical compound CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 claims description 7
- YIDCITOHTLPMMZ-UHFFFAOYSA-N 5-tert-butyl-1h-pyrazole Chemical compound CC(C)(C)C1=CC=NN1 YIDCITOHTLPMMZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- PTRATZCAGVBFIQ-UHFFFAOYSA-N Abametapir Chemical compound N1=CC(C)=CC=C1C1=CC=C(C)C=N1 PTRATZCAGVBFIQ-UHFFFAOYSA-N 0.000 claims description 3
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052745 lead Inorganic materials 0.000 claims description 3
- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 claims description 3
- GFJCGXFXOXSUJX-UHFFFAOYSA-N 5-butyl-1h-pyrazole Chemical compound CCCCC1=CC=NN1 GFJCGXFXOXSUJX-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 22
- 239000003446 ligand Substances 0.000 abstract description 16
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 183
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 165
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- 239000007787 solid Substances 0.000 description 102
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 48
- 238000000295 emission spectrum Methods 0.000 description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 41
- 125000004429 atom Chemical group 0.000 description 41
- 239000010410 layer Substances 0.000 description 41
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 238000000034 method Methods 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 238000002329 infrared spectrum Methods 0.000 description 35
- 238000005259 measurement Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 24
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 24
- 238000000862 absorption spectrum Methods 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000006862 quantum yield reaction Methods 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
- 238000004949 mass spectrometry Methods 0.000 description 14
- 229910052697 platinum Inorganic materials 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 238000002347 injection Methods 0.000 description 11
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- 239000003795 chemical substances by application Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 150000007960 acetonitrile Chemical class 0.000 description 6
- 239000013522 chelant Substances 0.000 description 6
- 238000010494 dissociation reaction Methods 0.000 description 6
- 230000005593 dissociations Effects 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 5
- 238000002447 crystallographic data Methods 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000012916 structural analysis Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 235000013405 beer Nutrition 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Chemical class O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound 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 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910003771 Gold(I) chloride Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000891 luminescent agent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- XHYNDAIIQREKSY-UHFFFAOYSA-N 3-tert-butylpyrazole-3-carboxylic acid Chemical class CC(C)(C)C1(C(O)=O)C=CN=N1 XHYNDAIIQREKSY-UHFFFAOYSA-N 0.000 description 1
- TZLCPYJWWDXRMH-UHFFFAOYSA-N 4-pyrimidin-4-ylpyrimidine Chemical compound C1=NC=CC(C=2N=CN=CC=2)=N1 TZLCPYJWWDXRMH-UHFFFAOYSA-N 0.000 description 1
- RXIDPALOABYPJL-UHFFFAOYSA-N 5-methyl-2-(5-methylpyrimidin-2-yl)pyrimidine Chemical compound N1=CC(C)=CN=C1C1=NC=C(C)C=N1 RXIDPALOABYPJL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing 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
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005101 luminescent paint Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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
- H10K85/30—Coordination compounds
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/10—Silver compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
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Abstract
Description
[(MII)2(MI)2(LC)2(LB)4]2+ (C1)
[式(C1)中、MIIは、PtIIまたはPdIIを示す。
MIは、H+、AuI、AgI、CuI、HgI、TlIまたはPbIを示す。
LCは、式(LC−1)〜式(LC−5)のいずれかで表される化合物を示す。
LBは、式(LB−1)で表される1価のアニオンを示す。
式(LB−1)中、X1は、置換基を有していてもよいアルキル基を示す。
X2およびX3は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有していてもよいアルキル基、または置換基を有していてもよいアリール基を示す。}]
[2] 式(C2)で表される上記[1]に記載の金属錯体。
[(MII)2(MI)2(LC)2(LB)4](PF6)2 (C2)
[式(C2)中、MII、MI、LCおよびLBは、前記と同義である。]
[3] MIIはPtIIであり、MIはH+、AuI、AgIまたはCuIであり、LCは2,2’−ビピリミジンまたは2,2’−ビピリジン(好ましくは2,2’−ビピリジン)であり、LBは3−t−ブチルピラゾールから水素イオンが解離して得られる1価のアニオンである、上記[1]または[2]に記載の金属錯体。
[4] MIIはPtIIであり、MIはH+またはAgIであり、LCは4,4’−ジメチル−2,2’−ビピリジンまたは5,5’−ジメチル−2,2’−ビピリジン(好ましくは4,4’−ジメチル−2,2’−ビピリジン)であり、LBは3−t−ブチルピラゾールから水素イオンが解離して得られる1価のアニオンである、上記[1]または[2]に記載の金属錯体。
[5] 上記[1]〜[4]のいずれか一つに記載の金属錯体を含む発光層を有する発光素子。
[6] 上記[5]に記載の発光素子を備えてなる表示装置。
[(MII)2(MI)2(LC)2(LB)4]2+ (C1)
即ち、本発明の金属錯体は、MIIおよびMIの2種のカチオン(金属イオンまたはH+)、キレート配位子LC、および架橋配位子LBを用いて構成される多核金属錯体である。
MIは、H+、AuI、AgI、CuI、HgI、TlIまたはPbIを示し、好ましくはH+、AuI、AgIまたはCuIであり、より好ましくはAgIである。
[(MII)2(MI)2(LC)2(LB)4](PF6)2 (C2)
[式(C2)中、MII、MI、LCおよびLBは、前記と同義である。]
本発明の金属錯体の一種である[Pt2(bpym)2(3-tBupz)2(3-tBupzH)2](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをH+、LCをbpym、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。二つのH+と二つの3-tBupzとが結合して、二つの3-tBupzHを形成している。なお、3-tBupzは、3−t−ブチルピラゾール(3-tBupzH)のN原子から水素イオンが解離して得られる1価のアニオンを表す。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3638(w), 3364(w), 3096(w), 2968(m), 1588(s), 1558(m), 1490(m), 1412(s), 1372(w), 1303(w), 1265(w), 1211(w), 1133(m), 1070(w), 1035(w), 846(s), 745(m), 678(w), 558(s)
また、1H NMRスペクトルの同定結果は、下記表1の通りである。ここで、表1中の各項目は、左から、δがピークの化学シフト(ppm)を示し、Shapeがピークの形状を示し、Jが結合定数(Hz)を示し、Int.がピーク強度(相対値)を示し、Assign.がピークの帰属を示す。
FAB-MS:m/z=746.6 [M-PF6]+
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3082(s), 2957(s), 2864(m), 1636(w), 1584(s), 1550(m), 1493(s), 1474(m), 1459(m), 1415(s), 1362(m), 1336(m), 1236(s), 1208(m), 1121(w), 1049(s), 991(w), 836(s), 760(m), 746(s), 726(w), 673(m), 559(s), 491(w)
また、1H NMRスペクトルの同定結果は、下記表2の通りである。表2中の各項目は、表1と同様である。
FAB-MS:m/z=1345.3 [M-PF6]+
本発明の金属錯体の一種である[Pt2Ag2(bpym)2(3-tBupz)4](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをAgI、LCをbpym、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3108(w), 2954(m), 2922(m), 2860(w), 1584(s), 1552(m), 1495(m), 1458(w), 1409(s), 1360(w), 1333(m), 1247(m), 1207(w), 1178(w), 1143(w), 1081(m), 1033(w), 845(s), 810(m), 778(w), 761(m), 748(s), 697(w), 675(w), 652(w), 558(s), 502(w)
また、1H NMRスペクトルの同定結果は、下記表4の通りである。表4中の各項目は、表1と同様である。
本発明の金属錯体の一種である[Pt2Au2(bpym)2(3-tBupz)4](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをAuI、LCをbpym、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。
収量は114mg(収率71%)であった。この反応は、下記の化学反応式で表すことができる。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3120(w), 2953(m), 2866(w), 1585(s), 1552(m), 1486(m), 1458(w), 1409(s), 1359(w), 1333(m), 1251(m), 1209(w), 1182(w), 1149(w), 1101(w), 1034(w), 1017(w), 962(w), 844(s), 810(m), 782(w), 766(m), 748(m), 717(w), 698(w), 676(w), 654(w), 558(s), 515(w)8(w), 761(m), 748(s), 697(w), 675(w), 652(w), 558(s), 502(w)
また、1H NMRスペクトルの同定結果は、下記表7の通りである。表7中の各項目は、表1と同様である。
FAB-MS:m/z=1737.3 [M-PF6]+
本発明の金属錯体の一種である[Pt2Cu2(bpym)2(3-tBupz)4](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをCuI、LCをbpym、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。
IR(KBr):3107(w), 2955(m), 2876(w), 1585(s), 1552(m), 1496(m), 1459(m), 1410(s), 1362(w), 1331(m), 1248(m), 1209(w), 1180(w), 1142(w), 1082(m), 1033(w), 1017(w), 845(s), 810(m), 777(m), 765(m), 748(s), 722(w), 697(w), 676(m), 652(w), 558(s), 504(w)
本発明の金属錯体の一種である[Pt2(bpy)2(3-tBupz)2(3-tBupzH)2](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをH+、LCをbpy、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。二つのH+と二つの3-tBupzとが結合して、二つの3-tBupzHを形成している。なお、bpyは2,2’−ビピリジンを表す。
IR(KBr):3356 (m), 3057 (w), 2967 (m), 2839 (m), 2366 (m), 1612 (s), 1567 (s), 1454 (s), 1368 (s), 1297 (s), 1246 (s), 1213 (s), 1134 (s), 1075 (s), 996 (s), 848 (m), 558 (s)
FAB-MS : m/z=744.3 [M-PF6]+
IRスペクトルの同定結果は、次の通りである。
IR(KBr):2957 (s), 2361 (s), 1633 (m), 1451 (s), 1236 (m), 1047(m), 834 (s), 762(m), 559 (s), 279 (s)
また、1H NMRスペクトルの同定結果は、下記表10の通りである。表10中の各項目は、表1と同様である。
FAB-MS:m/z=1341.6 [M-PF6]+
本発明の金属錯体の一種である[Pt2Ag2(bpy)2(3-tBupz)4](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをAgI、LCをbpy、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3439 (w), 3125 (m), 2950 (m), 2360 (m), 1610 (s), 1482 (m), 1455 (s), 1361 (m), 1328 (s), 1177 (s), 1136 (s), 1075 (m), 844 (m), 772 (s), 558 (s), 503 (m), 421 (m)
また、1H NMRスペクトルの同定結果は、下記表11の通りである。表11中の各項目は、表1と同様である。
FAB-MS:m/z=1555.3 [M-PF6]+
本発明の金属錯体の一種である[Pt2Au2(bpy)2(3-tBupz)4](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをAuI、LCをbpy、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3420 (w), 2956 (m), 2676 (m), 2606 (m), 2498 (s), 2360 (s), 1610 (s), 1475 (s), 1454 (s), 1397 (s), 1251 (m), 1210 (m), 1174 (m), 11036 (m), 843 (m), 771 (s), 723 (s), 558 (s), 279 (s)
また、1H NMRスペクトルの同定結果は、下記表14の通りである。表14中の各項目は、表1と同様である。
FAB-MS:m/z=1536 [M-PF6]+
本発明の金属錯体の一種である[Pt2Cu2(bpy)2(3-tBupz)4](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをCuI、LCをbpy、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3125 (w), 2948 (m), 2360 (s), 2342 (m), 1610 (s), 1485 (s), 1455 (s), 1428 (m), 1395 (s), 1360 (m), 1324 (s), 1249 (s), 1179 (m), 1084 (s), 844 (m), 774 (s), 726 (s), 655 (w), 558 (s), 279 (s)
また、1H NMRスペクトルの同定結果は、下記表16の通りである。表16中の各項目は、表1と同様である。
FAB-MS:m/z=1466 [M-PF6]+
本発明の金属錯体の一種である[Pt2Ag2(bpy)2(3-tBupz)4](BF4)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをAg+、LCをbpy、LBを3-tBupzとし、カウンターアニオンがBF4 -である構成である。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3054 (m), 2965 (m), 2360 (w), 2342 (w), 1608 (w), 1578 (w), 1476 (s), 1453 (m), 1370 (s), 1264 (s), 1245 (s), 1249 (s), 1130 (m), 733 (s), 705 (s)
また、1H NMRスペクトルの同定結果は、下記表17の通りである。表17中の各項目は、表1と同様である。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3452 (w), 2957 (m), 2360 (m), 1610 (s), 1492 (m), 1473 (s), 1361 (m), 1328 (s), 1163(s), 1136 (s), 1075 (m), 844 (m), 772 (s), 558 (s), 503 (m), 421 (m)
また、1H NMRスペクトルの同定結果は、下記表18の通りである。表18中の各項目は、表1と同様である。
FAB-MS:m/z=1497.3 [M-BF4]+
本発明の金属錯体の一種である[Pt2(5,5'-dmbpy)2(3-tBupz)2(3-tBupzH)2](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをH+、LCをdmbpy、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。二つのH+と二つの3-tBupzとが結合して、二つの3-tBupzHを形成している。なお、5,5'-dmbpyは5,5’−ジメチル−2,2’−ビピリジンを表す。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3427 (m), 3125 (m), 3021 (m), 2965 (s), 2913 (m), 2828 (s), 2359 (m), 1609 (m), 1569 (s), 1486 (s), 1393 (s), 1294 (s), 1133 (s), 1069 (s), 990 (s), 841 (s), 558 (s)
ESI-MS:m/z=626 [M-PF6]+
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3391 (w), 2958 (s), 2360 (m), 2139 (m), 1484 (s), 1387 (m), 1360 (w), 1237 (s), 1045(m), 840 (s), 754 (m), 503(w)
また、1H NMRスペクトルの同定結果は、下記表19の通りである。表19中の各項目は、表1と同様である。
FAB-MS:m/z=1251.6 [M-PF6]+
本発明の金属錯体の一種である[Pt2Ag2(5,5'-dmbpy)2(3-tBupz)4](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをAgI、LCを5,5'-dmbpy、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3658 (w), 3436 (w), 2960 (s), 2360 (w), 1609 (s), 1485 (s), 1391 (s), 1329 (s), 1146(s), 1092 (s), 1018 (s), 839(s), 770(m), 558(s)
また、1H NMRスペクトルの同定結果は、下記表20の通りである。表20中の各項目は、表1と同様である。
本発明の金属錯体の一種である[Pt2(4,4'-dmbpy)2(3-tBupz)2(3-tBupzH)2](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをH+、LCを4,4'-dmbpy、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。二つのH+と二つの3-tBupzとが結合して、二つの3-tBupzHを形成している。なお、4,4'-dmbpyは4,4’−ジメチル−2,2’−ビピリジンを表す。
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3132 (m), 3021 (m), 2966 (s), 2360 (s), 2337 (s), 1621 (s), 1489 (s), 1370 (s), 1132 (s), 991 (s), 848 (s), 558 (s)
FAB-MS:m/z=626.3 [M-PF6]+
IRスペクトルの同定結果は、次の通りである。
IR(KBr):3347 (w), 2958 (s), 2360 (m), 2342 (m), 1624 (s), 1491 (m), 1418 (w), 1236 (s), 833(s), 560 (s)
また、1H NMRスペクトルの同定結果は、下記表21の通りである。表21中の各項目は、表1と同様である。
FAB-MS:m/z=1251.6 [M-PF6]+
本発明の金属錯体の一種である[Pt2Ag2(4,4'-dmbpy)2(3-tBupz)4](PF6)2を合成した。この金属錯体は、上記式(C1)において、MIIをPtII、MIをAgI、LCを4,4'-dmbpy、LBを3-tBupzとし、カウンターアニオンがPF6 -である構成である。
IR(KBr):3471 (w), 2953 (s), 2359 (w), 2341 (w), 1620 (s), 1491 (s), 1329 (s), 1248 (s), 1081(s), 840 (s), 770 (m), 521(s), 501(m)
ESI-MS:1611.6 [M-PF6]+
2 陽極
3 正孔注入層
4 正孔輸送層
5 発光層
6 電子輸送層
7 電子注入層
8 陰極
Claims (6)
- 式(C1)で表されるカチオンを含む金属錯体。
[(MII)2(MI)2(LC)2(LB)4]2+ (C1)
[式(C1)中、MIIは、PtIIまたはPdIIを示す。
MIは、H+、AuI、AgI、CuI、HgI、TlIまたはPbIを示す。
LCは、式(LC−1)〜式(LC−5)のいずれかで表される化合物を示す。
LBは、式(LB−1)で表される1価のアニオンを示す。
{式(LC−1)〜式(LC−5)中、R1〜R34は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有していてもよいアルキル基、または置換基を有していてもよいアリール基を示すか、或いはR1〜R34のうち、隣り合う基の1組または複数の組が、置換基を有していてもよい炭化水素環、または置換基を有していてもよい複素環を形成している。
式(LB−1)中、X1は、置換基を有していてもよいアルキル基を示す。
X2およびX3は、それぞれ独立に、水素原子、ハロゲン原子、置換基を有していてもよいアルキル基、または置換基を有していてもよいアリール基を示す。}] - 式(C2)で表される請求項1に記載の金属錯体。
[(MII)2(MI)2(LC)2(LB)4](PF6)2 (C2)
[式(C2)中、MII、MI、LCおよびLBは、前記と同義である。] - MIIはPtIIであり、MIはH+、AuI、AgIまたはCuIであり、LCは2,2’−ビピリミジンまたは2,2’−ビピリジンであり、LBは3−t−ブチルピラゾールから水素イオンが解離して得られる1価のアニオンである、請求項1または2に記載の金属錯体。
- MIIはPtIIであり、MIはH+またはAgIであり、LCは4,4’−ジメチル−2,2’−ビピリジンまたは5,5’−ジメチル−2,2’−ビピリジンであり、LBは3−t−ブチルピラゾールから水素イオンが解離して得られる1価のアニオンである、請求項1または2に記載の金属錯体。
- 請求項1〜4のいずれか一項に記載の金属錯体を含む発光層を有する発光素子。
- 請求項5に記載の発光素子を備えてなる表示装置。
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