JP5294397B2 - 金属錯体化合物 - Google Patents
金属錯体化合物 Download PDFInfo
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- JP5294397B2 JP5294397B2 JP2008227072A JP2008227072A JP5294397B2 JP 5294397 B2 JP5294397 B2 JP 5294397B2 JP 2008227072 A JP2008227072 A JP 2008227072A JP 2008227072 A JP2008227072 A JP 2008227072A JP 5294397 B2 JP5294397 B2 JP 5294397B2
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- Japan
- Prior art keywords
- formula
- compound
- complex compound
- transition metal
- hydroxy
- Prior art date
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- -1 Metal complex compound Chemical class 0.000 title claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 15
- 150000003623 transition metal compounds Chemical class 0.000 claims description 13
- FYLYHNXYIWQPDE-UHFFFAOYSA-N 2,6-dihydroxynaphthalene-1,5-dicarbaldehyde Chemical compound O=CC1=C(O)C=CC2=C(C=O)C(O)=CC=C21 FYLYHNXYIWQPDE-UHFFFAOYSA-N 0.000 claims description 12
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 11
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims description 9
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 7
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 claims description 4
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical class C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000003446 ligand Substances 0.000 abstract description 31
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000012776 electronic material Substances 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical group [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 description 6
- 238000001663 electronic absorption spectrum Methods 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- HXFYGSOGECBSOY-UHFFFAOYSA-N 2-[[2-[(2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NC1=CC=CC=C1N=CC1=CC=CC=C1O HXFYGSOGECBSOY-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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 3
- 239000011701 zinc Substances 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- 0 *c(c(*)c1)cc(*2=Cc(c(cccc3)c3cc3)c3O*22*3)c1*2=Cc1*3ccc2c1cccc2 Chemical compound *c(c(*)c1)cc(*2=Cc(c(cccc3)c3cc3)c3O*22*3)c1*2=Cc1*3ccc2c1cccc2 0.000 description 2
- WRBJZNAPDVBCQM-UHFFFAOYSA-N 2,6-dihydroxynaphthalene-1-carbaldehyde Chemical compound O=CC1=C(O)C=CC2=CC(O)=CC=C21 WRBJZNAPDVBCQM-UHFFFAOYSA-N 0.000 description 2
- BJFZNFCWBRTCCI-UHFFFAOYSA-N 4,5-didecoxybenzene-1,2-diamine Chemical compound CCCCCCCCCCOC1=CC(N)=C(N)C=C1OCCCCCCCCCC BJFZNFCWBRTCCI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 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
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 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 2
- 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 2
- 150000002466 imines Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 2
- 239000004246 zinc acetate Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- UGNSMKDDFAUGFT-UHFFFAOYSA-N 4,4-dimethyl-2-phenyl-5h-1,3-oxazole Chemical compound CC1(C)COC(C=2C=CC=CC=2)=N1 UGNSMKDDFAUGFT-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 description 1
- XMOKRCSXICGIDD-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O XMOKRCSXICGIDD-UHFFFAOYSA-N 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- 229910021446 cobalt carbonate Inorganic materials 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 description 1
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- BKFAZDGHFACXKY-UHFFFAOYSA-N cobalt(II) bis(acetylacetonate) Chemical compound [Co+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O BKFAZDGHFACXKY-UHFFFAOYSA-N 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- UFKUWSBTKLUIIZ-UHFFFAOYSA-N copper;pentane-2,4-dione Chemical compound [Cu+2].CC(=O)CC(C)=O UFKUWSBTKLUIIZ-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000012789 electroconductive film Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- ZRSDQBKGDNPFLT-UHFFFAOYSA-N ethanol;oxolane Chemical compound CCO.C1CCOC1 ZRSDQBKGDNPFLT-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 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
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- 239000011656 manganese carbonate Substances 0.000 description 1
- 235000006748 manganese carbonate Nutrition 0.000 description 1
- 229940093474 manganese carbonate Drugs 0.000 description 1
- ZQZQURFYFJBOCE-FDGPNNRMSA-L manganese(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Mn+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O ZQZQURFYFJBOCE-FDGPNNRMSA-L 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- SZINCDDYCOIOJQ-UHFFFAOYSA-L manganese(2+);octadecanoate Chemical compound [Mn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SZINCDDYCOIOJQ-UHFFFAOYSA-L 0.000 description 1
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 description 1
- FLESAADTDNKLFJ-UHFFFAOYSA-N nickel;pentane-2,4-dione Chemical compound [Ni].CC(=O)CC(C)=O FLESAADTDNKLFJ-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000913 palmityl 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])C([H])([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
- 125000002958 pentadecyl 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])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
- WATYAKBWIQTPDE-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O WATYAKBWIQTPDE-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum 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
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011576 zinc lactate Substances 0.000 description 1
- 235000000193 zinc lactate Nutrition 0.000 description 1
- 229940050168 zinc lactate Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- BEAZKUGSCHFXIQ-UHFFFAOYSA-L zinc;diacetate;dihydrate Chemical compound O.O.[Zn+2].CC([O-])=O.CC([O-])=O BEAZKUGSCHFXIQ-UHFFFAOYSA-L 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(式中、Rは、互いに独立して、水素、C1−C18アルキル基またはアリール基であり、R′は、互いに独立して、水素、水酸基、C1−C8アルキル基、C1−C8アルコキシル基またはアリール基であり、そしてMは、2価もしくは3価の遷移金属カチオンである)で表される単核錯体化合物。
(式中、Rは、互いに独立して、水素、C1−C18アルキル基またはアリール基であり、R′は、互いに独立して、水素、水酸基、C1−C8アルキル基、C1−C8アルコキシル基またはアリール基であり、そしてMは、2価もしくは3価の遷移金属カチオンである)
で表される二核錯体化合物。
(式中、R、R′およびMは、上記に定義したとおりである)で表される単核錯体化合物の製造方法であって、式IV:
(式中、RおよびR′は、上記に定義したとおりである)で表されるN−(2−ヒドロキシ−1−ナフタリデン)−o−フェニレンジアミン化合物と、式V:
(式中、R′は、上記に定義したとおりである)で表される2−ヒドロキシ−1−ナフトアルデヒド化合物との混合物を、遷移金属化合物と反応させることを特徴とする、方法。
(式中、R、R′およびMは、上記に定義したとおりである)で表される二核錯体化合物の製造方法であって、式IV:
(式中、RおよびR′は、上記に定義したとおりである)で表されるN−(2−ヒドロキシ−1−ナフタリデン)−o−フェニレンジアミン化合物と、式VI:
の2,6−ジヒドロキシ−1,5−ナフタレンジカルバルデヒドとの混合物を、遷移金属化合物と反応させることを特徴とする、方法。
−電子吸収スペクトル
測定機器:JASCO V-630 spectrophotometer
測定試料:各実施例化合物の1×10−4Mピリジン(分析用グレード)溶液
−NMRスペクトル
測定機器:JEOL JNM-AL400(400 MHz for 1H)
−IRスペクトル
測定機器:Shimadzu FTIR-8700
−MSスペクトル
測定機器:JEOL JMS-600H
−元素分析
測定機器:FUSION INSTRUMENTS EA1108
2,6−ジヒドロキシナフトアルデヒド(207mg, 1.1mmol;C. Schieleら, Tetrahedron 24 (1968) p2293-2296 に従って合成した)を、THF(4mL)に溶解し、これを4,5−ビス(デシルオキシ)−1,2−フェニレンジアミン(239mg, 0.5mmol;D. T. Rosaら, Inorg. Synth. 33 (2002) p112-119 に従って合成した)のTHF/メタノール(v/v=1/1,5mL)溶液に、室温で加えた。12時間撹拌した後、反応混合物にメタノールを加え、沈殿を促した。析出した沈殿物をろ取し、赤紫色の結晶性固体として目的化合物139mg(収率34%)を得た。
IR (KBr) 3365 (νO-H), 1611 (νC=N) cm-1;
FAB(+) MS m/z 817.8 (817.5 calcd. for M+H+);
Elemental Analysis Calcd. for C52H68N2O6: C, 76.44; H, 8.39; N, 3.43. Found: C, 76.15; H, 8.40; N, 3.41.;
1H NMR (DMSO-d6) δ 0.85 (t (7.3 Hz), CH3, 6H), 1.20-1.40 (m, -CH2-, 32H), 1.42-1.51 (m, -CH2-, 4H), 1.73-1.80 (m, -CH2-, 4H), 4.15 (t (5.9 Hz), -CH2O-, 4H), 7.01 (d (9.2 Hz), ArH, 2H), 7.10-7.12 (m, ArH, 4H), 7.38 (s, ArH, 2H), 7.76 (d (9.3 Hz), ArH, 2H), 8.39 (d (9.7 Hz), ArH, 2H), 9.54 (br, ArOH, 2H), 9.56 (s, -CH=N-, 2H), 15.05 (br, ArOH, 2H).
2,6−ジヒドロキシナフトアルデヒド(753mg, 4.0mmol)を、THF−エタノール(v/v=1/4,25mL)に溶解し、これを4,5−ビス(デシルオキシ)−1,2−フェニレンジアミン(954mg, 2.0mmol)のTHF/エタノール(v/v=1/1,35mL)溶液に、室温で加えた。12時間撹拌した後、反応混合物を真空エバポレータで濃縮し、次いでメタノール30mLを加え、さらなる沈殿を促した。析出した沈殿物をろ取し、橙色の結晶性固体として目的化合物946mg(収率73%)を得た。
IR (KBr) 3192 (νO-H), 1607 (νC=N) cm-1;
FAB(+) MS m/z 647.5 (647.5 calcd. for M+H+);
Elemental Analysis Calcd. for C41H62N2O4・0.5H2O: C, 75.07; H, 9.68; N, 4.27. Found: C, 74.84; H, 9.71; N, 4.30.;
1H NMR (DMSO-d6) δ 0.85 (t (6.6 Hz), CH3, 6H), 1.19-1.38 (m, -CH2-, 32H), 1.40-1.48 (m, -CH2-, 4H), 1.64-1.74 (m, -CH2-, 4H), 3.90 (t (6.3 Hz), -CH2O-, 2H), 3.95 (t (6.4 Hz), -CH2O-, 2H), 4.76 (s, ArNH2, 2H), 6.50 (s, ArH, 1H), 7.04 (d (9.1 Hz), ArH, 1H), 7.10-7.13 (m, ArH, 2H), 7.22 (s, ArH, 1H), 7.72 (d (9.1 Hz), ArH, 1H), 8.41 (d (8.8 Hz), ArH, 1H), 9.49 (s, -CH=N-, 1H), 15.43 (s, ArOH, 1H).
実施例1で得られたリガンド(40.9mg, 0.05mmol)を、THF(5mL)に溶解し、それに酢酸亜鉛(II)・二水和物(12.1mg, 0.055mmol)のメタノール(1mL)溶液を、室温で滴下した。18時間撹拌した後、メタノール(6mL)を加え、次いで混合物を真空エバポレータで、固体が析出するまで濃縮した。析出した沈殿物をろ取し、赤紫色の結晶性固体として目的化合物38mg(収率86%)を得た。
FAB(+) MS m/z 879.6 (879.4 calcd. for M+H+);
Elemental Analysis Calcd. for C52H66N2O6Zn・2H2O: C, 68.15; H, 7.70; N, 3.06. Found: C, 68.18; H, 7.44; N, 3.00.;
1H NMR (DMSO-d6) δ 0.85 (t (6.5 Hz), CH3, 6H), 1.20-1.42 (m, -CH2-, 32H), 1.48-1.56 (m, -CH2-, 4H), 1.75-1.83 (m, -CH2-, 4H), 4.20 (t (6.0 Hz), -CH2O-, 4H), 6.92 (d (9.1 Hz), ArH, 2H), 6.99 (s, ArH, 2H), 7.03 (d (8.9 Hz), ArH, 2H), 7.56 (s, ArH, 2H), 7.59 (d 9.3 Hz), ArH, 2H), 8.29 (d (9.3 Hz), ArH, 2H), 9.23 (s, -CH=N-, 2H), 9.58 (s, ArOH, 2H).
実施例1で得られたリガンド(40.9mg, 0.05mmol)を、THF(2mL)に溶解し、それに酢酸銅(II)・無水物(10.0mg, 0.055mmol)のメタノール(2mL)溶液を、室温で滴下した。さらにメタノール(1mL)を加え、16時間撹拌すると、沈殿物が得られた。それをろ取し、暗紫色の結晶性固体として目的化合物45mg(収率100%)を得た。
FAB(+) MS m/z 878.5 (878.4 calcd. for M+H+), 900.7 (900.4 calcd. for M+Na+); Elemental Analysis Calcd. for C52H66CuN2O6・H2O: C, 69.65; H, 7.64; N, 3.12. Found: C, 69.38; H, 7.64; N, 3.15.
実施例1で得られたリガンド(40.9mg, 0.05mmol)を、THF(5mL)に溶解し、それに酢酸ニッケル(II)・四水和物(13.7mg, 0.055mmol)のメタノール(1mL)溶液を、室温で滴下した。混合物は速やか沈殿を形成した。これをろ取し、暗紫色の結晶性固体として目的化合物41mg(収率94%)を得た。
FAB(+) MS m/z 873.7 (873.4 calcd. for M+H+), 895.7 (895.4 calcd. for M+Na+);
Elemental Analysis Calcd. for C52H66N2NiO6・H2O: C, 70.03; H, 7.69; N, 3.14. Found: C, 69.85; H, 7.54; N, 3.16.;
1H NMR (DMSO-d6) δ 0.84 (t (6.3 Hz), CH3, 6H), 1.20-1.40 (m, -CH2-, 32H), 1.45-1.54 (m, -CH2-, 4H), 1.73-1.80 (m, -CH2-, 4H), 4.18 (t (6.8 Hz), -CH2O-, 4H), 7.04 (d (9.1 Hz), ArH, 2H), 7.08 (s, ArH, 2H), 7.10 (d (8.9 Hz), ArH, 2H), 7.64 (d 9.2 Hz), ArH, 2H), 7.80 (s, ArH, 2H), 8.38 (d (8.5 Hz), ArH, 2H), 9.06 (s, -CH=N-, 2H), 9.44 (s, ArOH, 2H).
実施例1で得られたリガンド(40.9mg, 0.05mmol)を、THF(2mL)に溶解し、それに塩化鉄(III)・六水和物(14.9mg, 0.055mmol)のメタノール(1mL)溶液を、室温で滴下した。トリエチルアミン(5μL)を加え、混合物を18時間放置した。メタノール(6mL)を加えた後、真空エバポレータで濃縮すると、沈殿が得られた。それをろ取し、暗褐色の結晶性固体として目的化合物29mg(収率64%)を得た。
FAB(+) MS m/z 870.6 (870.4 calcd. for M-Cl-), 905.6 (905.4 calcd. for M+);
Elemental Analysis Calcd. for C52H66ClFeN2O6・H2O: C, 67.56; H, 7.41; N, 3.03. Found: C, 67.44; H, 6.83; N, 2.80.
実施例2で得られたハーフリガンド(129.4mg, 0.2mmol)を、THF(5mL)に溶解し、それに2,6−ジヒドロキシ−1,5−ナフタレンジカルバルデヒド(21.6mg,0.1mmol;A. P. Kuriakose et al., Jour. Indian Chem. Soc., Vol. 43, No. 6, 1966 に記載の方法に従って合成した)のTHF(5mL)溶液を加えた。混合物が赤褐色の溶液に変化した後、酢酸亜鉛(II)・二水和物(48.3mg, 0.22mmol)のメタノール(3mL)溶液を、室温で滴下した。4時間撹拌した後、沈殿物が得られた。沈殿物をろ取し、メタノールで洗浄し、赤紫色の結晶性固体として目的化合物127.6mg(収率80%)を得た。
FAB(+) MS m/z 1599.7 (1597.8 calcd. for M+H+);
Elemental Analysis Calcd. for C94H124N4O10Zn2・4H2O: C, 67.49; H, 7.95; N, 3.35. Found: C, 67.38; H, 7.46; N, 3.48.;
1H NMR (pyridine-d5) δ 0.89 (t (6.6 Hz), CH3, 12H), 1.20-1.39 (m, -CH2-, 72H), 1.48-1.58 (m, -CH2-, 8H), 1.77-1.87 (m, -CH2-, 8H), 4.18 (t (6.4 Hz), -CH2O-, 4H), 4.22 (t (6.3 Hz), -CH2O-, 4H), 7.48 (d (9.3 Hz), ArH, 2H), 7.51 (d (9.2 Hz), ArH, 2H), 7.56 (s, ArH, 2H), 7.77 (d (9.5 Hz), ArH, 2H), 7.85 (s, ArH, 2H), 7.92 (s, ArH, 2H), 8.65 (d (9.3 Hz), ArH, 2H), 8.74 (d, ArH, 2H), 8.83 (d (9.3 Hz), ArH, 2H), 10.16 (s, -CH=N-, 2H), 10.20 (s, -CH=N-, 2H), 11.44 (s, ArOH, 2H).
実施例2で得られたハーフリガンド(129.4mg, 0.2mmol)を、THF(5mL)に溶解し、それに2,6−ジヒドロキシ−1,5−ナフタレンジカルバルデヒド(21.6mg,0.1mmol)のTHF(5mL)溶液を加えた。混合物が赤褐色の溶液に変化した後、酢酸銅(II)・無水物(40.0mg, 0.22mmol)のメタノール/THF(v/v=1/3,8mL)溶液を、室温で滴下した。11時間撹拌した後、沈殿物が得られた。沈殿物をろ取し、メタノールで洗浄し、暗紫色の結晶性固体として目的化合物137.5mg(収率86%)を得た。
FAB(+) MS m/z 1596.9 (1594.8 calcd. for M+H+);
Elemental Analysis Calcd. for C94H124Cu2N4O10・2H2O: C, 69.13; H, 7.90; N, 3.43. Found: C, 68.92; H, 7.81; N, 3.35.
実施例2で得られたハーフリガンド(129.4mg, 0.2mmol)を、THF(5mL)に溶解し、それに2,6−ジヒドロキシ−1,5−ナフタレンジカルバルデヒド(21.6mg,0.1mmol)のTHF(5mL)溶液を加えた。混合物が赤褐色の溶液に変化した後、酢酸ニッケル(II)・四水和物(54.7mg, 0.22mmol)のメタノール/THF(v/v=1/3,8mL)溶液を、室温で滴下した。12時間撹拌した後、沈殿物が得られた。沈殿物をろ取し、メタノールで洗浄し、赤紫色の結晶性固体として目的化合物132.2mg(収率83%)を得た。
FAB(+) MS m/z 1585.4 (1585.8 calcd. for M+H+);
Elemental Analysis Calcd. for C94H124N4Ni2O10・3H2O: C, 68.78; H, 7.98; N, 3.41. Found: C, 69.15; H, 7.79; N, 3.41.
実施例2で得られたハーフリガンド(64.7mg, 0.1mmol)を、THF(3mL)に溶解し、それに2,6−ジヒドロキシ−1,5−ナフタレンジカルバルデヒド(10.8mg,0.05mmol)のTHF(4mL)溶液を加えた。混合物が赤褐色の溶液に変化した後、塩化鉄(III)・六水和物(29.7mg, 0.11mmol)のメタノール(2mL)溶液を、室温で滴下した。トリエチルアミン(10μL)を加え、混合物を16時間放置した。沈殿物が得られ、それをろ取し、メタノールで洗浄し、黒色の結晶性固体として目的化合物33.0mg(収率40%)を得た。
FAB(+) MS m/z 1580.7 (1580.8 calcd. for M+-2Cl-);
Elemental Analysis Calcd. for C94H124Cl2Fe2N4O10・2H2O: C, 66.86; H, 7.64; N, 3.32. Found: C, 66.70; H, 7.09; N, 3.45.
実施例3〜10で得られた単核および二核錯体化合物の電子吸収スペクトルを、紫外可視分光光度計(JASCO V-630 spectrophotometer)にて測定した。試料は、実施例3〜10の化合物をピリジン(分析用グレード)に溶解し、1×10−4M溶液としたものを使用した。結果を図1〜4に示す。この電子吸収スペクトルから明らかなように、本発明の錯体化合物は、添付の図面に示すように、600nmを超える長波長領域に吸収を示すことから、半導体特性、導電性又は発光性などの特性を発揮することが期待される。
Claims (8)
- 遷移金属カチオンが、周期表第4周期の遷移金属から選択されるものである、請求項1または2に記載の錯体化合物。
- 遷移金属カチオンが、亜鉛(II)、銅(II)、ニッケル(II)、コバルト(II)、マンガン(II)または鉄(III)である、請求項3に記載の錯体化合物。
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