JPH04141493A - Metal chelate compound and optical recording medium using the same compound - Google Patents
Metal chelate compound and optical recording medium using the same compoundInfo
- Publication number
- JPH04141493A JPH04141493A JP2265906A JP26590690A JPH04141493A JP H04141493 A JPH04141493 A JP H04141493A JP 2265906 A JP2265906 A JP 2265906A JP 26590690 A JP26590690 A JP 26590690A JP H04141493 A JPH04141493 A JP H04141493A
- Authority
- JP
- Japan
- Prior art keywords
- group
- metal chelate
- chelate compound
- substitutional
- recording medium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 36
- 239000002184 metal Substances 0.000 title claims abstract description 36
- 239000013522 chelant Substances 0.000 title claims abstract description 34
- 230000003287 optical effect Effects 0.000 title claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004429 atom Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 150000001450 anions Chemical class 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 150000004820 halides Chemical class 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Chemical group 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Chemical group 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Chemical group 0.000 claims description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005154 alkyl sulfonyl amino alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 238000000576 coating method Methods 0.000 abstract description 14
- 238000010521 absorption reaction Methods 0.000 abstract description 12
- 239000011248 coating agent Substances 0.000 abstract description 12
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 13
- 239000000975 dye Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000010408 film Substances 0.000 description 8
- 239000004431 polycarbonate resin Substances 0.000 description 5
- 229920005668 polycarbonate resin Polymers 0.000 description 5
- 229910052724 xenon Inorganic materials 0.000 description 5
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- -1 polypropylene Polymers 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910020808 NaBF Inorganic materials 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001007 phthalocyanine dye Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- CSUFEOXMCRPQBB-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropan-1-ol Chemical compound CC(F)(F)C(O)(F)F CSUFEOXMCRPQBB-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000007606 doctor blade method Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- KUGBQWBWWNPMIT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoropentan-1-ol Chemical compound CC(F)(F)C(F)(F)C(F)(F)C(O)(F)F KUGBQWBWWNPMIT-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 229910002065 alloy metal Inorganic materials 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Optical Record Carriers And Manufacture Thereof (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野１
本発明は金属キレート化合物および該化合物を用いた光
学記録媒体に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application 1] The present invention relates to a metal chelate compound and an optical recording medium using the compound.
［従来の技術ル
−ザーを用いた光学記録は、高密度の情報記録保存およ
び再生を可能とするため、近年、特にその開発が取り進
められている。[Conventional Technology Optical recording using a loser has been particularly developed in recent years because it enables high-density information recording storage and reproduction.
光学記録の一例としては、光ディスクを挙げることがで
きる。An example of optical recording is an optical disc.
一般に、光ディスクは、円形の基体に設けられた薄い記
録層に、１μｍ程度に集束したレーザー光を照射し、高
密度の情報記録を行なうものである。In general, optical discs record high-density information by irradiating a thin recording layer provided on a circular base with laser light focused to about 1 μm.
その記録は、照射されたレーザー光エネルギーの吸収に
よって、その箇所の記録層に、分解、蒸発、溶解等の熱
的変形を生成させることにより行われる。また、記録さ
れた情報の再生は、レーザー光により変形が起きている
部分と起きていない部分の反射率の差を読み取ることに
より行なわれる。The recording is performed by causing thermal deformation such as decomposition, evaporation, and melting in the recording layer at that location by absorption of irradiated laser light energy. Further, recorded information is reproduced by reading the difference in reflectance between a portion where deformation has occurred and a portion where no deformation has occurred by laser light.
したがって、光学記録媒体としては、レーザー光のエネ
ルギーを効率よく吸収する必要があるため、記録に使用
する特定の波長のレーザー光に対する吸収が大きいこと
、情報の再生を正確に行なうため、再生に使用する特定
波長のレーザー光に対する反射率が高いことが必要とな
る。Therefore, as an optical recording medium, it is necessary to efficiently absorb the energy of laser light, so the absorption of laser light of a specific wavelength used for recording is large, and in order to accurately reproduce information, it is necessary to efficiently absorb the energy of laser light. It is necessary that the reflectance for laser light of a specific wavelength is high.
この種の光学記録媒体としては、種々の構成のものが知
られている。Various configurations of this type of optical recording medium are known.
例えば、特開昭５５−９７０３３号公報には、基板上に
フタロシアニン系色素の単層を設けたものが開示されて
いる。しかしながらフタロシアニン系色素は感度が低く
、また分解点が高く蒸着しにくい等の問題点を有し、さ
らに有機溶媒に対する溶解性が著しく低く、塗布による
コーティングに使用することができないという問題点を
有している。For example, JP-A-55-97033 discloses a method in which a single layer of a phthalocyanine dye is provided on a substrate. However, phthalocyanine dyes have problems such as low sensitivity, high decomposition point, and difficulty in vapor deposition.Additionally, phthalocyanine dyes have extremely low solubility in organic solvents, making them unsuitable for use in coatings. ing.
また、特開昭５８−８３３４４号公報にはフェナレン系
色素を、特開昭５８−２２４７９８号公報にはナフトキ
ノン系色素を記録層に設けたものが開示されている。し
かし、このような色素は蒸着しゃずいといる利点の反面
、反射率が低いという問題点を有している。反射率が低
いとレーザー光により記！？れた部分と未記録部分との
反射率に関係するコントラストが低くなり、記録された
情報の再生が困難となる。Further, JP-A-58-83344 discloses a recording layer in which a phenalene dye is provided, and JP-A-58-224798 discloses a recording layer in which a naphthoquinone dye is provided. However, although such dyes have the advantage of being easy to deposit by vapor deposition, they have the problem of low reflectance. If the reflectance is low, it will be marked with a laser beam! ? The contrast related to the reflectance between the recorded portion and the unrecorded portion becomes low, making it difficult to reproduce the recorded information.
更に、一般に有機系色素は保存安定性が劣るという問題
点を有している。Furthermore, organic dyes generally have a problem of poor storage stability.
［発明が解決しようとする課題］
本発明は、有機溶媒に対する溶解性が高く、塗布による
コーティングが可能で、しかも耐光性に優れレーザー光
線によって状態変化を生せしめることによって記録再生
を行なうための光学記録媒体の色素として適した金属キ
レート化合物および該化合物を用いた光学記録媒体を提
供することを目的とするものである。[Problems to be Solved by the Invention] The present invention provides an optical recording device that has high solubility in organic solvents, can be coated by coating, has excellent light resistance, and is capable of recording and reproducing by causing a state change with a laser beam. The object of the present invention is to provide a metal chelate compound suitable as a dye for a medium and an optical recording medium using the compound.
［課題を解決するための手段ｊ
即ち、本発明は、−能代（Ｉ）
（式中、Ｍは■族、Ｉｂ族、Ｉｌｂ族、ＩＩＩ ａ族、
ＩＶａ族、Ｖａ族、ＶＩａ族、■ａ族の金属原子、また
はその酸化物もしくはハロゲン化物を表わし、環Ａは置
換基を有していてもよい。Ｒ１およびＲ２はそれぞれ独
立して水素原子、炭素数１〜２０の置換もしくは非置換
のアルキル基、置換もしくは非置換のアリール基、置換
もしくは非置換のアルケニル基または置換もしくは非置
換のシクロアルキル基を表わし、Ｑは陰イオンを表わす
。ｎは２または３である。）で示されることを特徴とす
る金属キレート化合物および該化合物を用いた光学記録
媒体に存する。[Means for Solving the Problems j] That is, the present invention provides - Noshiro (I) (wherein M is group II, group Ib, group Ilb, group IIIa,
It represents a metal atom of the IVa group, Va group, VIa group, or ■a group, or its oxide or halide, and ring A may have a substituent. R1 and R2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted cycloalkyl group. where Q represents an anion. n is 2 or 3. ) and an optical recording medium using the compound.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
一般式（Ｉ）中、Ｍは鉄、コバルト、ニッケル、ルテニ
ウム、ロジウム等の■族原子、銅、銀、金のＩｂ族原子
、亜鉛、カドミウム、水銀のＩＩｂＩｂ族原子カンジウ
ム、イットリウへ等のＩＩＩａ族原゛子、チタン、ジル
コニウム、ハフニウムのＩＶ ａ族原子、バナジウム、
ネオジウム、タンタルのＶａ族原子、クロム、モリブデ
ン、タングステンの■ａａ族原子マンガン、テクネチウ
ム、レニウムの■ａａ族原子またはこれらの酸化物もし
くはフッ化物、塩化物、臭化物、ヨウ化物等のハロゲン
化物を表わす。In the general formula (I), M is a group I atom such as iron, cobalt, nickel, ruthenium, rhodium, etc., a group Ib atom of copper, silver, gold, a group IIb atom of zinc, cadmium, mercury, a group Ib atom such as candium, yttrium, etc. Group IV a atoms of titanium, zirconium, hafnium, vanadium,
Represents Va group atoms of neodymium and tantalum; ■aa group atoms of chromium, molybdenum, and tungsten; ■aa group atoms of manganese, technetium, and rhenium, or their oxides or halides such as fluorides, chlorides, bromides, and iodides. .
環Ａはアルキル基、アルコキシ基、ハロゲン原子、ニト
ロ基、シアノ基、アルキルスルホニル基、アルコキシカ
ルボニル基等から選ばれる１以上の置換基を有していて
もよい。Ring A may have one or more substituents selected from an alkyl group, an alkoxy group, a halogen atom, a nitro group, a cyano group, an alkylsulfonyl group, an alkoxycarbonyl group, and the like.
Ｒ１およびＲ２で示されるアルキル基、アリール基、ア
ルケニル基またはシクロアルキル基の置換基としては、
例えば、アルコキシ基、アルコキシアルコキシ基、アル
コキシアルコキシアルキル基、アリルオキシ基、アリー
ル基、アリールオキシ基、シアノ基、ヒドロキシ基、テ
トラヒドロフリル基、アルキルスルホニルアミノ基等が
挙げられる。Substituents for the alkyl group, aryl group, alkenyl group or cycloalkyl group represented by R1 and R2 include:
Examples include an alkoxy group, an alkoxyalkoxy group, an alkoxyalkoxyalkyl group, an allyloxy group, an aryl group, an aryloxy group, a cyano group, a hydroxy group, a tetrahydrofuryl group, an alkylsulfonylamino group, and the like.
一般式（Ｉ）で示される金属キレート化合物のうち、好
ましいものとしては、
一般式（ＩＩ）
（式中、Ｍはニッケル、銅、コバルト、亜鉛、鉄、パラ
ジウムまたは白金原子を表わし、Ｒ３およびＲ４はそれ
ぞれ独立して炭素数１〜８のアルキル基、アルコキシア
ルキル基、アルコキシアルコキシアルキル基、アルコキ
シアルコキシアルコキシアルキル基、アリルオキシアル
キル基、アリールアルキル基、アリールオキシアルキル
基、シアノアルキル基、ヒドロキシアルキル基、テトラ
ヒドロフリルアルキル基、アルキルスルホニルアミノア
ルキル基、アシルオキシアルキル基、アルケニル基を表
わし、Ｑは陰イオンを表わす。ｎは２または３である。Among the metal chelate compounds represented by the general formula (I), preferred are the metal chelate compounds represented by the general formula (II) (wherein M represents a nickel, copper, cobalt, zinc, iron, palladium or platinum atom, R3 and R4 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxyalkyl group, an alkoxyalkoxyalkyl group, an alkoxyalkoxyalkoxyalkyl group, an allyloxyalkyl group, an arylalkyl group, an aryloxyalkyl group, a cyanoalkyl group, or a hydroxyalkyl group. , a tetrahydrofuryl alkyl group, an alkylsulfonylaminoalkyl group, an acyloxyalkyl group, an alkenyl group, Q represents an anion, and n is 2 or 3.
）で示される金属キレート化合物が挙げられ、特に好ま
しいものとしては、−能代［１１］で示される金属キレ
ート化合物において、Ｒ３およびＲ４が炭素数１〜６の
アルキル基であるものが挙げられる。), and particularly preferred are metal chelate compounds represented by -Noshiro [11] in which R3 and R4 are alkyl groups having 1 to 6 carbon atoms.
−能代（Ｉ）および（１■）において、Ｑで表わされる
陰イオンとしては、例えばｌ−１Ｂｒ−１Ｃ１−１Ｆ−
１Ｃ１０４−ＰＦ６二５ｂＦ６−１ＢＦ４−、５ＣＮ−
１ＣＨｎ今５Ｏ３−１（δヒ５Ｏ３−ＣＨ３ＣＯＯ−１
ＴｉＦｅ−１好ましくは、■−１Ｂｒ”、Ｃ１−１ＣＩ
Ｏ４−１ＰＦ６−１ＳｂＦａ−１ＢＦ４−１の陰イオン
である。- In Noshiro (I) and (1■), the anion represented by Q is, for example, l-1Br-1C1-1F-
1C104-PF625bF6-1BF4-, 5CN-
1CHnnow5O3-1(δhi5O3-CH3COO-1
TiFe-1 preferably ■-1Br”, C1-1CI
It is an anion of O4-1PF6-1SbFa-1BF4-1.
前記−能代（Ｉ）で示される金属キレート化合物は、６
００〜８００ｎｍの波長帯域で吸収を有し、しかも分子
吸収係数が１０’ｃｍ７’以上の高い値を有し、光学記
録媒体として優れた適性を有している。The metal chelate compound represented by -Noshiro (I) is 6
It has absorption in the wavelength band of 00 to 800 nm, and has a high molecular absorption coefficient of 10'cm7' or more, making it excellently suited as an optical recording medium.
−能代（Ｉ）で示される金属キレート化合物の一般的合
成は、たとえば、下記構造式
で示される８−ヒドロキシキノリンと、下記−能代（Ｉ
ＩＩ ）
（式中、Ａ、 Ｒ１およびＲ２は前記定義に同じ。）で
示される化合物とを酸化的縮合し、続いて分子内閉環に
よって、下記−能代（ＩＶ）
（式中、Ａ、 Ｒ１およびＲ２は前記定義に同じ。）で
示されるインドアニリン誘導体を得、次いで下記−能代
ＥＶ）
ＭＱ ・・・（Ｖ）（式中、
ＭおよびＱは前記定義に同じ。）で示される金属塩とを
反応させることにより得れることができる。The general synthesis of the metal chelate compound represented by -Noshiro (I) includes, for example, 8-hydroxyquinoline shown by the following structural formula and -Noshiro (I) shown below.
II) (In the formula, A, R1 and R2 are the same as defined above) by oxidative condensation, followed by intramolecular ring closure to form the following Noshiro (IV) (wherein A, R1 and R2 are the same as defined above). R2 is the same as defined above.) to obtain an indoaniline derivative represented by the following - Noshiro EV) MQ ... (V) (in the formula,
M and Q are the same as defined above. ) can be obtained by reacting with a metal salt represented by:
本発明の光学記録媒体は、基本的には基板と金属キレー
ト化合物を含む記録層とから構成されるものであるが、
さらに必要に応じて基板上に下引き層を、また記録層上
に保護層を設けることがで１〇−
きる。The optical recording medium of the present invention is basically composed of a substrate and a recording layer containing a metal chelate compound.
Furthermore, if necessary, an undercoat layer can be provided on the substrate and a protective layer can be provided on the recording layer.
本発明における基板としては、使用するレザー光に対し
て透明なものが好ましく、例えばガラス、プラスチック
等の一般の記録材料・の支持体が挙げられるが、プラス
チックが種々の点から好適である。プラスチックとして
は、アクリル（’ＡＪ脂、メタクリル樹脂、酢酸ビニル
（ｈ］脂、塩化ビニル樹脂、二Ｉ・ロセルロース、ポリ
エチレン樹脂、ポリプロピレン樹脂、ポリカーボネート
樹脂、ボッイミド樹脂、エボギシ樹脂、ポリザルポン樹
脂等が挙げられる。The substrate in the present invention is preferably one that is transparent to the laser light used, and examples include supports of general recording materials such as glass and plastic, with plastic being preferred from various points of view. Examples of plastics include acrylic ('AJ resin, methacrylic resin, vinyl acetate (h) resin, vinyl chloride resin, di-I-cellulose, polyethylene resin, polypropylene resin, polycarbonate resin, Voimide resin, Evogishi resin, polyzarpone resin, etc.) It will be done.
本発明の光学記録媒体における記録層として金属キレー
ト化合物を含有する際、記録層の膜厚は１００人〜５ｐ
ｍ、好ましくは１０００八〜３１１ｍである。成膜法と
しては真空蒸着法、スパッタリング法、ドクターブレー
ド法、ギヤスト法、スピナー法、浸漬法など一般に行な
われている薄膜形成法を挙げることができる。また、必
要に応じてバインダーを使用することもできる。バイン
ダーとしては、ポリビニルアルコール１、ポリビニルピ
ロリドン、ニトロセルロース、酢酸セルロース、ポリビ
ニルブチラール、ポリカーボネ−１・などの既知のもの
が用いられ、金属キレート化合物に列するバインダーの
量は５０重量％以下であることが好ましい。When the recording layer of the optical recording medium of the present invention contains a metal chelate compound, the thickness of the recording layer is 100 to 5p.
m, preferably 10008 to 311 m. Examples of the film forming method include commonly used thin film forming methods such as a vacuum evaporation method, a sputtering method, a doctor blade method, a gear strike method, a spinner method, and a dipping method. Moreover, a binder can also be used if necessary. Known binders such as polyvinyl alcohol 1, polyvinylpyrrolidone, nitrocellulose, cellulose acetate, polyvinyl butyral, and polycarbonate 1 are used as the binder, and the amount of the binder in the metal chelate compound range is 50% by weight or less. is preferred.
また、記録体の安定性や両光性向上のために、−重項酸
素クエンチャーとして遷移金属キレート化合物（例えば
、アセチルアセ）・ナートキレート、ビスフエニルジチ
オール、ザリチル７′ルデヒドオギシム、ビスジチオ−
α−ジケトン等）を含有していてもよい。更に、必要に
応じて他の色素を併用することができる。他の色素とし
ては別の種類の同系統の化合物でもよいし、トリアリー
ルメタン系色素、アゾ染料、ジアニン系色素、スクワリ
リウム系色素など他系統の色素でもよい。In addition, in order to improve the stability and ambidextrous properties of the recording medium, transition metal chelate compounds (e.g. acetylacetate), natochelates, bisphenyldithiol, salityl 7'rudehyde oxime, bisdithio-
α-diketone, etc.) may be contained. Furthermore, other dyes can be used in combination as necessary. The other dyes may be other types of compounds of the same type, or may be dyes of other types such as triarylmethane dyes, azo dyes, dianine dyes, and squarylium dyes.
ドクターブレード法、ギヤスト法、スピナー法、浸漬法
、特に、スピナー法等の塗布方法により記録層を形成す
る場合の塗布溶媒としては、テトラクロロエタン、フロ
モポルム、ジブロモエタン、エチルセロソルブ、キシレ
ン、クロロベンゼン、シクロへギザノン等の沸点１．２
０〜１６０°Ｃのものが好適に使用される。When forming a recording layer by a coating method such as a doctor blade method, a gearst method, a spinner method, or a dipping method, in particular, a spinner method, the coating solvent may include tetrachloroethane, flomoporum, dibromoethane, ethyl cellosolve, xylene, chlorobenzene, cyclo Boiling point of hegizanone etc. 1.2
A temperature range of 0 to 160°C is preferably used.
この中でも、高生産性・コスト・耐吸湿性に優れる射出
成型ポリカーボネート樹脂基板に列して（」、該基板を
おかずことなく、好適に使用できる溶媒として特に、ジ
アセトンアルコール、３−ヒドロキシ−３−メチル−２
−ブタノン等のケトンアルコール系溶媒；メチルセロソ
ルブ、エチルセロソルブ等のセロソルブ系溶媒；テトラ
フルオロプロパツール、（オクタフルオロペンタノール
等のパーフルオロアルキルアルコール系溶媒；乳酸メチ
ル、イソ醋酸メチル等のヒドロギシエステル系溶媒液；
が挙げられる。また、スピナー法により成膜の場合、回
転数は５００〜５０００ ｒｐｍが好ましく、スピンコ
ードの後、場合によっては、加熱あるいは溶媒蒸気にあ
てる等の処理を行なってもよい。Among these, diacetone alcohol, 3-hydroxy-3, -methyl-2
- Ketone alcohol solvents such as butanone; cellosolve solvents such as methyl cellosolve and ethyl cellosolve; perfluoroalkyl alcohol solvents such as tetrafluoropropanol and (octafluoropentanol); hydroxyesters such as methyl lactate and methyl isoacetate System solvent liquid;
can be mentioned. Further, in the case of film formation by a spinner method, the rotation speed is preferably 500 to 5000 rpm, and after the spin code, treatment such as heating or exposure to solvent vapor may be performed as the case requires.
本発明の光学記録媒体の記録層は基板の両面に設けても
よいし、片面だけに設けてもよい。The recording layer of the optical recording medium of the present invention may be provided on both sides of the substrate or only on one side.
」二足のようにして得られた光学記録媒体への記録は、
基体の両面または、片面に設けた記録層に］ｐｍ程度に
集束したレーザー光、好ましくは、半導体レーザーの光
をあてることにより行なう。レーザー光の照射された部
分には、レーザーエネルギーの吸収による、分解、蒸発
、溶融等の記録層の熱的変形が起こる。” The recording on the optical recording medium obtained like two feet is
This is carried out by irradiating the recording layer provided on both sides or one side of the substrate with a laser beam, preferably a semiconductor laser beam, focused to about 1 pm. In the portion irradiated with the laser beam, thermal deformation of the recording layer such as decomposition, evaporation, and melting occurs due to absorption of laser energy.
記録された情報の再生は、レーザー光により、熱的変形
が起きている部分と起きていない部分（７）反射率の差
を読み取ることにより行なう。The recorded information is reproduced by using a laser beam to read the difference in reflectance between a portion where thermal deformation has occurred and a portion where no thermal deformation has occurred (7).
本発明の光学記録媒体について使用されるレーザー光は
Ｎ２、Ｈｅ−Ｃｄ、 Ａｒ、 Ｈｅ−Ｎｅ、ルビー、半
導体、色素レーザーなどが挙げられるが、特に、軽量性
、取扱いの容易さ、コンパクト性などの点から半導体レ
ーザーが好適である。Laser beams used for the optical recording medium of the present invention include N2, He-Cd, Ar, He-Ne, ruby, semiconductor, dye lasers, etc., but in particular lightness, ease of handling, compactness, etc. From this point of view, semiconductor lasers are preferred.
［実施例１
以下、実施例により本発明を具体的に説明するが、本発
明はその要旨を越えない限り実施例により限定されるも
のではない。[Example 1] Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited by the Examples unless the gist thereof is exceeded.
実施例１
（ａ）化合物製造例
下記構造式
で示される８−アミノキノリン０．５ｇ及び下記構造式
で示されるアニリン誘導体１．．９０ｇを、水酸化す１
−リウム０．４２ｇを含む水５０ｍ１に加え、超音波処
理を１−ｉっな。この溶液にフェリシアン化カリウムＫ
ｚＦｅ（ＣＮ）６２．２７１ｇを含む水８．３ｍｌを室
；話にて滴−「シた後、１０分間同じ温度にて撹拌した
。次いで亜鉛粉末０．２２４ｇ、塩化亜鉛０．４７ｇ及
び水酸化カリウム１３ｇを含む沸騰水１６７ｍ１をゆっ
くり加えた。その後１ｏ分間撹拌した後、熱濾過し、下
記構造式
で示される紫色粉末の閉環タイプのインドアニリン誘導
体］、、２２ｇを得た。Example 1 (a) Compound Preparation Example 0.5 g of 8-aminoquinoline represented by the following structural formula and aniline derivative represented by the following structural formula 1. ．． 90g, hydroxylated 1
- Add to 50 ml of water containing 0.42 g of lithium and apply ultrasonic treatment for 1-i. Potassium ferricyanide K is added to this solution.
After dropping 8.3 ml of water containing 62.271 g of zFe(CN) into the chamber, the mixture was stirred at the same temperature for 10 minutes. Then, 0.224 g of zinc powder, 0.47 g of zinc chloride and hydroxide 167 ml of boiling water containing 13 g of potassium was slowly added. After stirring for 10 minutes, the mixture was hot-filtered to obtain 22 g of a purple powder ring-closed type indoaniline derivative represented by the following structural formula.
本化合物をアセトンに溶解すると赤紫色の蛍光色を示し
た。When this compound was dissolved in acetone, it exhibited a reddish-purple fluorescent color.
上記化合物１．０９ｇをテトラヒトフラン７５ｍ１に溶
解させた後、室温にて塩化ニッケルＮｉＣｌ□１．０５
ｇを加え、濾過し、炉液をＮａＢＦ４７５ｇを含む水１
．５０ｍ１に加えて、沈殿を得た。濾過、水洗して下記
構造式で示される金属キレート化合物（閉環タイプの合
金属インドアニリン化合物）０．８４ｇを得た。After dissolving 1.09 g of the above compound in 75 ml of tetrahydrofuran, 1.05 g of nickel chloride NiCl□ was added at room temperature.
1 g of water containing 475 g of NaBF.
．． In addition to 50 ml, a precipitate was obtained. After filtration and washing with water, 0.84 g of a metal chelate compound (ring-closed type alloy metal indoaniline compound) represented by the following structural formula was obtained.
得られた金属キレート化合物の可視部の吸収スペクトル
はλｒｎａｘ ６５０ｎｍ （クロロホルム中）であっ
た。The absorption spectrum in the visible region of the obtained metal chelate compound was λrnax 650 nm (in chloroform).
（ｂ）光学記録媒体製造例−１
前記化合物製造例（ａ）で得た金属キレート化合物０．
１ｇをテトラクロロエタン１０ｇに溶解し、０．２２ｐ
ｍのフィルターで濾過し、溶解液を得た。この溶液】。(b) Optical recording medium production example-1 The metal chelate compound obtained in the above compound production example (a).
Dissolve 1g in 10g of tetrachloroethane, 0.22p
The solution was filtered through a filter of 1.0 m to obtain a solution. this solution].
ｍｌをポリメチルメタクリレ−１−（ＰＭＭＡ）１δ］
脂基板（直径５２ ｍｍ ）の上に滴下し、スピナー法
により８００ｒｐｍの回転数で塗布した。塗布後、６０
０Ｃで１０分間乾燥した。塗布膜の最大吸収波長は６７
０ｎｍであり、６ス
ベクトル
（ｃ）光学記録例−１
この塗布膜に、中心波長６３３ ｎ．ｍ ｔ７）Ｈｅ
− Ｎｅレザー光を出力６ｍＷで照射したところ、輪郭
の極めて明瞭なピットが形成された。ml of polymethyl methacrylate-1-(PMMA) 1δ]
The mixture was dropped onto a resin substrate (diameter 52 mm) and coated using a spinner at a rotation speed of 800 rpm. After application, 60
Dry for 10 minutes at 0C. The maximum absorption wavelength of the coating film is 67
0 nm, and the center wavelength of 633 nm was applied to this coating film. m t7) He
- When Ne laser light was irradiated with an output of 6 mW, pits with extremely clear outlines were formed.
また、得られた光学記録媒体のキセノンランプによる耐
光性促進テストは、極めて良好であった。Further, the light fastness acceleration test of the obtained optical recording medium using a xenon lamp was extremely good.
（ｄ）光学記録媒体製造例−２
前記化合物製造例（ａ）で得た金属キレート化合物０、
２ｇをテトラフルオロプロパツール１０ｇに溶解し、０
、２２ｐｍのフィルターで濾過し、溶解液を得た。この
溶液５ｍｌを直径５インチ板厚１．２ｍｍの１．６μｍ
ピッチの溝（グループ）つきポリカーボネート樹脂基板
（躬”出成型品）」−に滴下し、スピナー法により８０
０ｒｐｍの回転数で塗布した。塗布後、６０°Ｃで１０
分間乾燥した。塗布膜の最大吸収波長は６７０ｎｍであ
り、スペクトルの形状はｔ４−ｒ広かった。(d) Optical recording medium production example-2 Metal chelate compound 0 obtained in the above compound production example (a),
Dissolve 2g in 10g of tetrafluoropropanol,
, 22 pm filter to obtain a solution. Add 5 ml of this solution to a 1.6 μm plate with a diameter of 5 inches and a thickness of 1.2 mm.
It was dropped onto a polycarbonate resin substrate with pitch grooves (groups) (a molded product) and was
Coating was performed at a rotation speed of 0 rpm. After application, heat at 60°C for 10
Dry for a minute. The maximum absorption wavelength of the coating film was 670 nm, and the shape of the spectrum was t4-r wide.
（ｅ）光学記録例−２
上記記録層を成膜したポリカーボネート樹脂基板を線速
４ｍ／ｓで回転さぜながら、中心波長６３３ｎ．ｍのＨ
ｅ−Ｎｅレーザー光でパルス幅５００ ｎｓｅｃで照射
したところ、高いＣ／Ｎ比を得た。(e) Optical Recording Example-2 While rotating the polycarbonate resin substrate on which the recording layer was formed at a linear velocity of 4 m/s, the center wavelength was 633 nm. H of m
When irradiated with e-Ne laser light with a pulse width of 500 nsec, a high C/N ratio was obtained.
また、得られた光学記録媒体のキセノンランプによる耐
光性促進テストは、極めて良好であった。Further, the light fastness acceleration test of the obtained optical recording medium using a xenon lamp was extremely good.
参考例 実施例１の化合物製造例（ａ）で使用した下記構造式 で示されるアニリン誘導体は次のようにして合成した。Reference example The following structural formula used in compound production example (a) of Example 1 The aniline derivative represented by was synthesized as follows.
塩化亜鉛６．８１ｇを水１．５０ｍｌに溶解させた。こ
れに下記構造式
で示される４−ジエチルアミノアニリン８．２ｇを室温
にて加えるとピンク色の溶液が得られ／．：。ＴＩＡＣ
酸アル酸二ルミニウムＡ１２４）３ ・１６Ｈ２０ ７
７ｇを水］．５０ｍｌに溶解させ、前記溶液に加えた。6.81 g of zinc chloride was dissolved in 1.50 ml of water. When 8.2 g of 4-diethylaminoaniline represented by the following structural formula is added to this at room temperature, a pink solution is obtained. :. TIAC
Acid diluminium alkate A124)3 ・16H20 7
7g water]. It was dissolved in 50 ml and added to the above solution.
チオ硫酸ナトリウムＮａ２Ｓ２Ｏ３・５Ｈ２０５２ｇを
水１００ｍ１に溶解させ、室温にてさらに前記溶液に加
えると薄い線色に変化した。最後にに２Ｃｒ２Ｃ）ｙ
５．０４ｇの濃溶液１００ｍ１を加え、室温にて４時間
撹拌したところ、徐々に灰色の沈殿が生成した。この沈
殿を濾過した後、水洗し、次いでベンゼン；エーテルで
洗浄した。さらに、室温で過剰の炭酸ナトリウム水溶液
に溶解した後、酢酸で中和して再沈殿を行ない、下記構
造式
で示される灰色の細かい結晶５．８６ｇ （収率４２％
）を得た。When 2052 g of sodium thiosulfate Na2S2O3.5H was dissolved in 100 ml of water and further added to the solution at room temperature, the color changed to a light line. Finally, 2Cr2C)y
When 100 ml of a concentrated solution of 5.04 g was added and stirred at room temperature for 4 hours, a gray precipitate gradually formed. After filtering this precipitate, it was washed with water and then with benzene and ether. Furthermore, after dissolving in excess sodium carbonate aqueous solution at room temperature, it was neutralized with acetic acid and reprecipitated, resulting in 5.86 g of fine gray crystals shown by the following structural formula (yield: 42%).
) was obtained.
実施例２
（ａ）化合物製造例
実施例１において下記構造式
で表わされる化合物１．０９ｇの代りに、下記構造式
で表される化合物１．００ｇを用いたこと以外は実施例
１と同様に行ない、下記構造式で表わされる金属キレー
ト化合物を得た。Example 2 (a) Compound Production Example Same as Example 1 except that 1.00 g of the compound represented by the following structural formula was used instead of 1.09 g of the compound represented by the following structural formula in Example 1. A metal chelate compound represented by the following structural formula was obtained.
得られた金属キレート化合物の可視部の吸収スペクトル
（クロロホルム中）は、λｍａｘ ６２０ ｎｍであっ
た。The visible absorption spectrum (in chloroform) of the obtained metal chelate compound was λmax 620 nm.
（ｂ）光学記録媒体製造例
前記化合物製造例（ａ）で得た金属キレート化合物を実
施例１に記載の方法に準じて、グループっきＰＭＭＡ樹
脂基板上にスピナー法による塗布を行なった。塗布膜の
最大吸収波長は６４０ ｎｍであり、スペクトルの形状
は巾広かった。(b) Optical Recording Medium Production Example The metal chelate compound obtained in Compound Production Example (a) was applied onto a group-plated PMMA resin substrate using a spinner method in accordance with the method described in Example 1. The maximum absorption wavelength of the coating film was 640 nm, and the shape of the spectrum was wide.
（ｃ）光学記録例
上記記録層を成膜したＰＭＭＡ樹脂基板を線速４ｍ／ｓ
で回転させながら、中心波長６３３ ｎｍのＨｅ −Ｎ
ｅレーザー光で、パルス幅５００ ｎ５ｅｃで照射した
ところ、高いＣ／Ｎ比を得た。得られた光学記録媒体の
キセノンランプによる耐光性促進テストも良好であった
。(c) Optical recording example A PMMA resin substrate on which the above recording layer was formed was processed at a linear speed of 4 m/s.
He-N with a center wavelength of 633 nm while rotating at
When irradiated with e-laser light with a pulse width of 500 n5ec, a high C/N ratio was obtained. The obtained optical recording medium also performed well in an accelerated light fastness test using a xenon lamp.
実施例３
（ａ）化合物製造例
実施例１において、ＮａＢＦ４７５ｇの代りにＮａＢＦ
４７５ｇを用いたこと以外は、実施例１と同様に行ない
、下記構造式で表される金属キレート化合物を得た。Example 3 (a) Compound production example In Example 1, NaBF was used instead of 475 g of NaBF.
A metal chelate compound represented by the following structural formula was obtained in the same manner as in Example 1 except that 475 g was used.
得らえた金属キレート化合物の可視部の吸収スピクトル
（クロロポルム中）はλｍａｘ ６５１ ｎｍであった
。The visible region absorption spectrum (in chloroporm) of the obtained metal chelate compound was λmax 651 nm.
（ｂ）光学記録媒体製造例
前記化合物製造例（ａ）で得た金属キレート化合物を実
施例１に記載の方法に準じて、直径５インチのグループ
つきポリカーボネート樹脂基板（射出成型品）上に滴下
し、スピナー法により６００ｒｐｍの回転数で塗布した
。塗布後、８０°Ｃで１０分間乾燥した。(b) Optical recording medium production example The metal chelate compound obtained in the above compound production example (a) was dropped onto a polycarbonate resin substrate (injection molded product) with groups of 5 inches in diameter according to the method described in Example 1. The coating was applied using a spinner method at a rotation speed of 600 rpm. After coating, it was dried at 80°C for 10 minutes.
塗布膜の最大吸収波長は６７１ ｎｍであり、スペクト
ルの形状は巾広かった。The maximum absorption wavelength of the coating film was 671 nm, and the shape of the spectrum was wide.
次に、この記録層の上にスパッタリング法により、膜厚
２０００人の金の膜を成膜して反対側を形成した。さら
に、この反射層の上に紫外線硬化性樹脂をスピンコード
した後、紫外線を照射して硬化させ、厚み１０ｐｍの保
護層を形成して光学記録媒体を得た。Next, a gold film having a thickness of 2000 was formed on the recording layer by sputtering to form the opposite side. Further, an ultraviolet curable resin was spin-coded on the reflective layer, and then cured by irradiation with ultraviolet rays to form a protective layer with a thickness of 10 pm to obtain an optical recording medium.
（ｅ）光学記録例
上記記録層を成膜したポリカーボネート樹脂基板を線速
１．４ｍ／ｓで回転させながら、波長７８５ ｎｍの半
導体レーザー光を用いてＥＦＭ変調信号を記録した後再
生し、その再生波形から反射率およびＬＩＴ変調度を測
定したところ、それぞれ７４％、７２％であった。(e) Optical recording example While rotating the polycarbonate resin substrate on which the recording layer was formed at a linear velocity of 1.4 m/s, an EFM modulated signal was recorded using a semiconductor laser beam with a wavelength of 785 nm, and then reproduced. When the reflectance and LIT modulation degree were measured from the reproduced waveform, they were 74% and 72%, respectively.
ここで１１Ｔ変調度とは、最長記録ピットの信号振幅を
反射率で割った値を百分率で表わしたものである。Here, the 11T modulation degree is the value obtained by dividing the signal amplitude of the longest recording pit by the reflectance, expressed as a percentage.
得られた光学記録媒体のキセノンランプによる耐光性促
進テストは極めて良好であった。The optical recording medium thus obtained was extremely good in a light fastness acceleration test using a xenon lamp.
実施例４
実施例１において用いた金属キレート化合物の代わりに
第１表に示した化合物を使用して記録層を成膜したとこ
ろ、第１表に示す最大吸収波長をもつ光学記録媒体を得
た。このようにして得られた薄膜に光源としてＨｅ−Ｎ
ｅレーザーを用いて書き込みを行なったところ、均一か
つ明瞭な形状のピットが得られた。Ｃ／Ｎ比も良好であ
り、キセノンランプによる耐光性促進テストも良好であ
った。Example 4 When a recording layer was formed using the compounds shown in Table 1 instead of the metal chelate compound used in Example 1, an optical recording medium having the maximum absorption wavelength shown in Table 1 was obtained. . The thin film thus obtained was coated with He-N as a light source.
When writing was performed using an e-laser, pits with a uniform and clear shape were obtained. The C/N ratio was also good, and the accelerated light resistance test using a xenon lamp was also good.
第１表
一２５＝
第２表
第３表
［発明の効果］
本発明の金属キレート化合物は、有機溶媒に対する溶化
性が高く、塗布によるコーティングが可能であり、ｌ−
かも配光性に優れているので、該金属キレート化合物を
用いた光学記録媒体は一土業的に極めて有用なものであ
る。Table 1-25 = Table 2 Table 3 [Effects of the Invention] The metal chelate compound of the present invention has high solubility in organic solvents, can be coated by coating, and has l-
Furthermore, since the metal chelate compound has excellent light distribution, optical recording media using the metal chelate compound are extremely useful in the industry.
Claims (4)
族、Ｖａ族、VIａ族、VIIａ族の金属原子、またはその
酸化物もしくはハロゲン化物を表わし、環Ａは置換基を
有していてもよい。Ｒ＾１およびＲ＾２はそれぞれ独立
して水素原子、炭素数１〜２０の置換もしくは非置換の
アルキル基、置換もしくは非置換のアリール基、置換も
しくは非置換のアルケニル基または置換もしくは非置換
のシクロアルキル基を表わし、Ｑは陰イオンを表わす。 ｎは２または３である。）で示されることを特徴とする
金属キレート化合物。(1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, M is group VIII, group Ib, group IIb, group IIIa, IVa
represents a metal atom of Group Va, Group VIa, or Group VIIa, or an oxide or halide thereof, and ring A may have a substituent. R^1 and R^2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted alkenyl group. It represents a cycloalkyl group, and Q represents an anion. n is 2 or 3. ) A metal chelate compound characterized by the following.
ジウムまたは白金原子を表わし、Ｒ＾３、Ｒ＾４はそれ
ぞれ独立して炭素数１〜８のアルキル基、アルコキシア
ルキル基、アルコキシアルコキシアルキル基、アルコキ
シアルコキシアルコキシアルキル基、アリルオキシアル
キル基、アリールアルキル基、アリールオキシアルキル
基、シアノアルキル基、ヒドロキシアルキル基、テトラ
ヒドロフリルアルキル基、アルキルスルホニルアミノア
ルキル基、アシルオキシアルキル基、アルケニル基を表
わし、Ｑは陰イオンを表わす。ｎは２または３である。 ）で示されるものである特許請求の範囲第１項記載の金
属キレート化合物。(2) General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [II] (In the formula, M represents nickel, copper, cobalt, zinc, iron, palladium or platinum atom, and R^3 , R^4 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxyalkyl group, an alkoxyalkoxyalkyl group, an alkoxyalkoxyalkoxyalkyl group, an allyloxyalkyl group, an arylalkyl group, an aryloxyalkyl group, a cyanoalkyl group , hydroxyalkyl group, tetrahydrofuryl alkyl group, alkylsulfonylaminoalkyl group, acyloxyalkyl group, alkenyl group, Q represents an anion, n is 2 or 3). A metal chelate compound according to scope 1.
おいて、Ｒ＾３およびＲ＾４が炭素数１〜６のアルキル
基を表わすものである特許請求の範囲第２項記載の金属
キレート化合物。(3) The metal chelate compound according to claim 2, wherein R^3 and R^4 represent an alkyl group having 1 to 6 carbon atoms in the metal chelate compound represented by the general formula [II].
記録媒体であり、色素に熱的変化を与える集束レーザー
光を照射して記録層に部分的な変化を生ぜしめて記録を
行ない、次いで該変化部分の選択によって再生を行なう
記録媒体であって、色素が特許請求の範囲第１項ないし
第３項のいずれか１項に記載の金属キレート化合物であ
ることを特徴とする光学記録媒体。(4) A recording medium in which a recording layer containing a dye is supported on a substrate, and recording is performed by irradiating a focused laser beam that thermally changes the dye to cause a partial change in the recording layer. , an optical recording medium that is then reproduced by selecting the changed portion, wherein the dye is a metal chelate compound according to any one of claims 1 to 3. Medium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2265906A JP3064373B2 (en) | 1990-10-03 | 1990-10-03 | Metal chelate compound and optical recording medium using the compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2265906A JP3064373B2 (en) | 1990-10-03 | 1990-10-03 | Metal chelate compound and optical recording medium using the compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04141493A true JPH04141493A (en) | 1992-05-14 |
| JP3064373B2 JP3064373B2 (en) | 2000-07-12 |
Family
ID=17423745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2265906A Expired - Lifetime JP3064373B2 (en) | 1990-10-03 | 1990-10-03 | Metal chelate compound and optical recording medium using the compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3064373B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218072B1 (en) | 1997-11-20 | 2001-04-17 | Taiyo Yuden Co., Ltd. | Optical information recording medium |
-
1990
- 1990-10-03 JP JP2265906A patent/JP3064373B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218072B1 (en) | 1997-11-20 | 2001-04-17 | Taiyo Yuden Co., Ltd. | Optical information recording medium |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3064373B2 (en) | 2000-07-12 |
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