JPS63209995A - Optical data recording medium - Google Patents
Optical data recording mediumInfo
- Publication number
- JPS63209995A JPS63209995A JP62044870A JP4487087A JPS63209995A JP S63209995 A JPS63209995 A JP S63209995A JP 62044870 A JP62044870 A JP 62044870A JP 4487087 A JP4487087 A JP 4487087A JP S63209995 A JPS63209995 A JP S63209995A
- Authority
- JP
- Japan
- Prior art keywords
- group
- groups
- general formula
- recording medium
- recording
- 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.)
- Pending
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 15
- 239000000758 substrate Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 25
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000004033 plastic Substances 0.000 abstract description 6
- 229920003023 plastic Polymers 0.000 abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract description 4
- 239000011521 glass Substances 0.000 abstract description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract description 2
- 230000008929 regeneration Effects 0.000 abstract description 2
- 238000011069 regeneration method Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- -1 O13 Inorganic materials 0.000 description 38
- 239000010410 layer Substances 0.000 description 33
- 239000000975 dye Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000013522 chelant Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052686 Californium Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 101100208039 Rattus norvegicus Trpv5 gene Proteins 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- TXOZSRCVHASUCW-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropan-1-ol Chemical compound OC(F)CC(F)(F)F TXOZSRCVHASUCW-UHFFFAOYSA-N 0.000 description 1
- VVSHLNMRFJNXRQ-UHFFFAOYSA-N 1-dodecyl-1-ethylpyrazolidin-1-ium Chemical group CCCCCCCCCCCC[N+]1(CC)CCCN1 VVSHLNMRFJNXRQ-UHFFFAOYSA-N 0.000 description 1
- FFYRIXSGFSWFAQ-UHFFFAOYSA-N 1-dodecylpyridin-1-ium Chemical group CCCCCCCCCCCC[N+]1=CC=CC=C1 FFYRIXSGFSWFAQ-UHFFFAOYSA-N 0.000 description 1
- KFOJDQXHEJWCNA-UHFFFAOYSA-N 1-ethyl-1-hexadecylpiperidin-1-ium Chemical group CCCCCCCCCCCCCCCC[N+]1(CC)CCCCC1 KFOJDQXHEJWCNA-UHFFFAOYSA-N 0.000 description 1
- ORIHZIZPTZTNCU-VMPITWQZSA-N 2-[(E)-hydroxyiminomethyl]phenol Chemical compound O\N=C\C1=CC=CC=C1O ORIHZIZPTZTNCU-VMPITWQZSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- XOGKALCNLBMSGI-UHFFFAOYSA-N 2-sulfanylidene-3h-dithiole Chemical compound S=S1CC=CS1 XOGKALCNLBMSGI-UHFFFAOYSA-N 0.000 description 1
- JMTFLSQHQSFNTE-UHFFFAOYSA-O 3-dodecyl-1h-imidazol-3-ium Chemical group CCCCCCCCCCCCN1C=C[NH+]=C1 JMTFLSQHQSFNTE-UHFFFAOYSA-O 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VFUFXTUSTQVXEA-UHFFFAOYSA-N B.CNC.[Na] Chemical class B.CNC.[Na] VFUFXTUSTQVXEA-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 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
- 239000004642 Polyimide Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical group CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IZLAVFWQHMDDGK-UHFFFAOYSA-N gold(1+);cyanide Chemical compound [Au+].N#[C-] IZLAVFWQHMDDGK-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 229910052945 inorganic sulfide Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- HKSGQTYSSZOJOA-UHFFFAOYSA-N potassium argentocyanide Chemical compound [K+].[Ag+].N#[C-].N#[C-] HKSGQTYSSZOJOA-UHFFFAOYSA-N 0.000 description 1
- XTFKWYDMKGAZKK-UHFFFAOYSA-N potassium;gold(1+);dicyanide Chemical compound [K+].[Au+].N#[C-].N#[C-] XTFKWYDMKGAZKK-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
- 229940098221 silver cyanide Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 125000005323 thioketone group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
- G11B7/2478—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes oxonol
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2531—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising glass
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、有機色素薄膜を有し、高密度エネルギービー
ムによって状態変化を生せしめることにより記録及び再
生を行なうヒートモードの光学的情報記録媒体に関する
。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a heat mode optical information recording medium that has an organic dye thin film and performs recording and reproduction by causing a state change with a high-density energy beam. Regarding.
従来、回転している円盤状の情報記録媒体にレーザービ
ームを照射して情報の記録及び再生を行なう情報記録媒
体が知られている。このような記録媒体の記録層として
は低融点金属または低融点金属と誘電体を用いるものな
どが提案されている。2. Description of the Related Art Conventionally, information recording media have been known in which information is recorded and reproduced by irradiating a rotating disc-shaped information recording medium with a laser beam. As the recording layer of such a recording medium, one using a low melting point metal or a low melting point metal and a dielectric material has been proposed.
しかしこれらは保存性が悪い、分離能が低い、記録密度
が低い、製造コストが高いなどの欠点があった。近年、
比較的長波長の光で物性変化し得る色素薄膜を記録層に
用いることが提案され、また実施されてはいるが、一般
に長波長に吸収帯を有する色素は熱および光に対する安
定性が低いなどの問題点があり、必ずしも長期にわたっ
て安定して満足すべき記録特性を有する記録層が開発さ
れていないのが現状である。However, these have drawbacks such as poor storage stability, low separation ability, low recording density, and high manufacturing cost. recent years,
Although it has been proposed and implemented to use a dye thin film whose physical properties can be changed by relatively long wavelength light in the recording layer, dyes that have absorption bands at long wavelengths generally have low stability against heat and light. Due to these problems, the current situation is that a recording layer that has stable and satisfactory recording characteristics over a long period of time has not been developed.
したがって本発明の目的は、十分な記録特性を長期にわ
たって維持し得るような安定性に優れた色素記録層を有
する光学的情報記録媒体を提供することである。Therefore, an object of the present invention is to provide an optical information recording medium having a highly stable dye recording layer that can maintain sufficient recording characteristics over a long period of time.
本発明の目的は、レーザー光線によって記録、再生、消
去を行なうための光学的情報記録媒体であって、基板上
に、オキソノール色素を担持せしめたことを特徴とする
光学的情報記録媒体により達成された。The object of the present invention is achieved by an optical information recording medium for recording, reproducing, and erasing using a laser beam, characterized in that an oxonol dye is supported on a substrate. .
本発明に用いられるオキソノール色素は、カルボニル基
とヒドロキシ基が互いに、置換されていてもよいポリメ
チン鎖で連結された化合物であって可視光ないし近赤外
光を吸収し得る化合物である。これらのオキソノール色
素の例は従来知られているものも多く、例えば、特公昭
４３−１３１６８号、同５１−４４１９号、同５３−２
８０８５号、同５５−１００６０号、同５５−１００６
１号、同５５−１０１８７号、同５５−１０８９９号、
特開昭５０−１４５１２５号、同５５−３３１０４号、
米国特許第３．６４９．４６５号、または英国特許第１
．３３８．７９９号などに記載されている。The oxonol dye used in the present invention is a compound in which a carbonyl group and a hydroxyl group are connected to each other by an optionally substituted polymethine chain, and is a compound capable of absorbing visible light to near-infrared light. Many examples of these oxonol dyes are conventionally known, such as those disclosed in Japanese Patent Publications Nos. 43-13168, 51-4419, and 53-2.
No. 8085, No. 55-10060, No. 55-1006
No. 1, No. 55-10187, No. 55-10899,
JP-A-50-145125, JP-A No. 55-33104,
U.S. Patent No. 3.649.465 or British Patent No. 1
．． 338.799, etc.
本発明で用いられるオキソノール色素のうち特に好まし
いものは下記一般式（１）で示されるものである。Among the oxonol dyes used in the present invention, particularly preferred ones are those represented by the following general formula (1).
一般式（Ｉ）
〔式中、ＹＳＺは炭素環もしくは複素環を形成するのに
必要な原子団を表わし、Ｌは置換されていてもよいメチ
ン基、または共役二重結合で連結された置換されていて
もよいポリメチン鎖を完成する原子団を表わし、Ａ、、
Ｑは共役二重結合鎖を完成する原子団を表わし、ｍ、ｎ
はそれぞれ独立に０または１を表わす。〕
ＹまたはＺで完成される環は好ましくは４．５．６．７
員環であり、さらに他の４．５．６．７員環と縮合環を
形成していてもよ（、置換基を有していてもよい。General formula (I) [In the formula, YSZ represents an atomic group necessary to form a carbocycle or a heterocycle, and L is an optionally substituted methine group, or a substituted group connected with a conjugated double bond. A represents an atomic group that completes a polymethine chain, which may be
Q represents an atomic group that completes a conjugated double bond chain, m, n
each independently represents 0 or 1. ] The ring completed by Y or Z is preferably 4.5.6.7
It is a membered ring, and may form a condensed ring with another 4-, 5-, 6-, or 7-membered ring (and may have a substituent).
ＹまたはＺで完成される複素環を形成するヘテロ原子と
して好ましいものは、Ｂ、Ｎ、０１Ｓ１ＳｅＳＴｅであ
る。Preferred heteroatoms forming a heterocycle completed by Y or Z are B, N, and 01S1SeSTe.
ＹもしくはＺで表わされる原子団のうち、炭素環を形成
するものとしては例えば以下のものが挙１ｆられる。Among the atomic groups represented by Y or Z, examples of those forming a carbon ring include the following 1f.
＋Ｃ）Ｉｚ）ｉ ÷ＣＨ，）−、、−ＣＨ＝ＣＨ−、
−ＣＨ＝Ｃ１ｌ−ＣＨ＝［”Ｈ−１ＹもしくはＺで表わ
される原子団のうち複素環を形成するものとしては、例
えば以下のものが挙げられる。+C)Iz)i ÷CH,)-, -CH=CH-,
-CH=C11-CH=["H-1 Among the atomic groups represented by Y or Z, examples of those forming a heterocycle include the following.
１＜ ＲＲは、置換
されていてもよいアルキル基（ベンジル基も含む）また
は置換されていてもよいアリール基を表わす。1<RR represents an optionally substituted alkyl group (including a benzyl group) or an optionally substituted aryl group.
ＹもしくはＺで表わされる原子団のうち特に好ましいも
のは５員もしくは６員の複素環を完成し得るものであり
、Ｂ、Ｎ、Ｏ１３，Ｓｅ、 Ｔｅのうちから選ばれる少
なくとも１種のへテロ原子を含むものである。Among the atomic groups represented by Y or Z, particularly preferable ones are those capable of completing a 5- or 6-membered heterocycle, and include at least one hetero group selected from B, N, O13, Se, and Te. It contains atoms.
して表わされる連結基としては、特に一般式（ａ）ない
しく社）で表わされるものが好ましい。As the linking group represented by, those represented by the general formula (a) or (a) are particularly preferred.
一般式（ａ）
札Ｈ−ＣＨ岸ＣＨ−（ｉ ＝Ｃ）Ｉ ｆｃＨ＝ＣＨ）−
ｉ−一般式ら）
＝ＣＨ−ＣＨ＝Ｃ−Ｃ８−Ｃ１ｌ −
一般式（Ｃ）
一般式（ｅ）
■
一般式（ｆ）
一般式（（イ）
一般式婦）
一般式（ａ）ないしく社）においてＹは水素原子または
、１価の基を表わし、ｐおよびｑは独立に０もしくは１
を表わす。この場合、１価の基としては、メチル基など
の低級アルキル基、メトキシ基などの低級アルコキシ基
、ジメチルアミン基、ジフェニルアミノ基、メチルフェ
ニルアミノ基、モルフォリノ基、イミダゾリジノ基、エ
トキシ力ルポニルビベラジノ基などのジ置換アミ７基、
アセトキシ基などのアルキルカルボニルオキシ基、メチ
ルチオ基などのアルキルチオ基、シアノ基、ニトロ基、
Ｆ、、Ｃｆ、Ｂｒなどのハロゲン原子などが好ましい。General formula (a) Tag H-CH Kishi CH-(i=C)I fcH=CH)-
i-General formula, etc.) =CH-CH=C-C8-C1l - General formula (C) General formula (e) ■ General formula (f) General formula ((A) General formula) General formula (a) or Inc.), Y represents a hydrogen atom or a monovalent group, and p and q are independently 0 or 1.
represents. In this case, monovalent groups include lower alkyl groups such as methyl groups, lower alkoxy groups such as methoxy groups, dimethylamine groups, diphenylamino groups, methylphenylamino groups, morpholino groups, imidazolidino groups, and ethoxy groups. di-substituted amine 7 groups such as dino group,
Alkylcarbonyloxy groups such as acetoxy groups, alkylthio groups such as methylthio groups, cyano groups, nitro groups,
Preferred are halogen atoms such as F, Cf, and Br.
なおして表わされる連結基のうち特に好ましいものは一
般式（ａ）もしくはい）で表わされるものであり、とく
にＹが水素原子を表わし、ｐもしくはｑのうち少なくと
も一方が０を表わすものである。Among the linking groups represented above, particularly preferred are those represented by the general formula (a) or (i), particularly those in which Y represents a hydrogen atom and at least one of p or q represents 0.
一般式（Ｉ）におけるり、Ｙ、またはＺ上の置換基とし
て好ましいものは、炭素原子数３０以下のものであって
、以下に挙げる基の中から選ばれ、これらの基はさらに
置換基を有していてもよい。Preferred substituents on R, Y, or Z in general formula (I) have 30 or less carbon atoms and are selected from the groups listed below, and these groups may further have a substituent. may have.
すなわち、アルキル基、アラルキル基、アリール基、ヒ
ドロキシ基、Ｆ、Ｃｆ、Ｂｒ、Ｉ、シアノ基、ニトロ基
、アルコキシ基、アラルキルオキシ基、アリールオキシ
基、アシル基、アシロキシ基、アシルアミノ基、スルホ
ンアミド基、アリールオキシカルボニル基、アラルキル
オキシカルボニル基、アルコキシカルボニル基、カルバ
モイル基、スルファモイル基、カルボキシ基もしくはカ
ルボキシラド基、スルホン酸基もしくはスルホナト基、
カルバモイルアミノ基、スルファモイルアミノ基、アル
キルスルホニル基、アラルキルスルホニル基、アルキル
スルホニル基、アルキルスルフィニル基、アラルキルス
ルフィニル基、アリールスルフィニル基、アルキルチオ
基、アラルキルチオ基、またはアリールチオ基である。That is, alkyl groups, aralkyl groups, aryl groups, hydroxy groups, F, Cf, Br, I, cyano groups, nitro groups, alkoxy groups, aralkyloxy groups, aryloxy groups, acyl groups, acyloxy groups, acylamino groups, sulfonamides. group, aryloxycarbonyl group, aralkyloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, sulfamoyl group, carboxyl group or carboxylad group, sulfonic acid group or sulfonato group,
A carbamoylamino group, a sulfamoylamino group, an alkylsulfonyl group, an aralkylsulfonyl group, an alkylsulfonyl group, an alkylsulfinyl group, an aralkylsulfinyl group, an arylsulfinyl group, an alkylthio group, an aralkylthio group, or an arylthio group.
以下に本発明で用いられるオキソノール色素の具体例を
挙げるが、本発明の範囲はこれらのみに限定されるもの
ではない。Specific examples of oxonol dyes used in the present invention are listed below, but the scope of the present invention is not limited only to these.
１゜
ｌ０１
Ｕ Ｕｉｌ
ｌ。1゜l01 U Uil
l.
１２゜
１３゜
１４゜
１５゜
１６゜
１７゜
１８゜
Ｈｉ
１９゜
２０゜
２１゜
２２゜
２３゜
２５゜
２６．
２７゜
［：Ｊｓ シＪｓ
２８゜
３０゜
３１゜
３２゜
３３゜
３４゜
３５゜
本発明において用いられるオキソノール色素は一般に活
性メチレン化合物をオルトエステルや反応させて、メチ
レン鎖で連結することにより合成できる。より具体的に
は、特公昭３９−２２０６９号、同４３−３５０４号、
同５２−３８０５６号、同５４−３８１２９号、同５５
−１００５９号、特開昭４９−９９６２０号、同５９−
１６８３４号、あるいは米国特許第４．１８１．２２５
号などに記載されている方法を利用して合成することが
できる。12゜13゜14゜15゜16゜17゜18゜Hi 19゜20゜21゜22゜23゜25゜26. 27゜[:Js しJs
28° 30° 31° 32° 33° 34° 35° The oxonol dye used in the present invention can generally be synthesized by reacting an active methylene compound with an orthoester and linking the resultant with a methylene chain. More specifically, Japanese Patent Publication No. 39-22069, No. 43-3504,
No. 52-38056, No. 54-38129, No. 55
-10059, JP-A No. 49-99620, JP-A No. 59-
16834 or U.S. Patent No. 4.181.225
It can be synthesized using the method described in No.
以下に、合成した代表的な化合物の融点を示す。The melting points of typical synthesized compounds are shown below.
表
本発明の光記録媒体において用いられるオキソノール色
素は単独で用いても、２種以上併用してもよく、あるい
は本発明のオキソノール色素以外の色素と併用して用い
てもよい。また読取り耐久性向上のため種々の酸化防止
剤や一重項酸素クエンチャ−を併用することも有効であ
る。また、種々の樹脂を併用してもよい。Table The oxonol dyes used in the optical recording medium of the invention may be used alone, in combination of two or more, or in combination with dyes other than the oxonol dye of the invention. It is also effective to use various antioxidants and singlet oxygen quenchers in combination to improve reading durability. Moreover, various resins may be used in combination.
あるいは遷移金属イオンを添加してキレートを形成させ
て用いることにより耐久性を増すこともできる。Alternatively, durability can be increased by adding transition metal ions to form a chelate.
本発明の光記録媒体に使用されるクエンチャ−としては
、種々のものを用いることができる。このようなりエン
チャーとしては、再生劣化を低下させ、色素との相溶性
が良好な遷移金属錯体が好ましい。この場合、中心金属
として好ましいものは、Ｎｉ、 Ｃｏ、Ｃｕ、 Ｐｄ、
Ｐｔなどである。Various quenchers can be used in the optical recording medium of the present invention. As such an encher, a transition metal complex is preferable because it reduces regeneration deterioration and has good compatibility with the dye. In this case, preferable central metals are Ni, Co, Cu, Pd,
Such as Pt.
新規なりエンチャーの例としては次の一般式（ＩＩ）ま
たは（ＩＩＩ）で示されるものがあげられる。Examples of novel enchers include those represented by the following general formula (II) or (III).
（式中、ｃｃａｔ＋”＋およびＣＣａｔｚ：］は錯体を
中性ならしめるために必要な陽イオンを示し、Ｍｌおよ
びＭ２はニッケル、銅、コバルト、パラジウムまたは白
金を示す。ｎは１または２を示す。）前記一般式（ｎ）
または〔■〕で表わされる化合物において、（Ｃａｔ、
］または（Ｃａｔ２〕で表わされる陽イオンのうち無機
陽イオンとしては、アルカリ金属（たとえば、Ｌｉ、
ＮａＪＫなど）、アルカリ土類金属（Ｍｇ、 （：ａ、
Ｂａなど）もしくはＮＨ４−をあげることができる。(In the formula, ccat+"+ and CCatz:] represent a cation necessary to neutralize the complex, Ml and M2 represent nickel, copper, cobalt, palladium, or platinum. n represents 1 or 2. .) The above general formula (n)
Or in the compound represented by [■], (Cat,
] or (Cat2), the inorganic cations include alkali metals (for example, Li,
NaJK, etc.), alkaline earth metals (Mg, (:a,
(Ba, etc.) or NH4-.
また有機陽イオンとしては、第四級アンモニウムイオン
または第四級ホスホニウムイオンをあげることができる
。Examples of the organic cation include quaternary ammonium ions and quaternary phosphonium ions.
上記の陽イオンｃｃａｔ＋〕および（Ｃａｔ、）の中で
好ましいのは下記の一般式（ＩＶ−ａ）、（ＴＶ−ｂ）
（ｒＶ−ｃ）、（ＩＶ−ｄ）もしくは（ｒＶ−ｅ）で表
わされるものである。Among the above cations ccat+] and (Cat, ), the following general formulas (IV-a) and (TV-b) are preferred.
(rV-c), (IV-d) or (rV-e).
式中、Ｒ′１、Ｒ１２、Ｒｌ ３、Ｒ目、Ｒ”％ Ｒ１
６、Ｒ”、Ｒ１８、ＲＩ９、Ｒ”、Ｒ”およびＲ２２は
それぞれ炭素数１ないし２０の置換もしくは無置換のア
ルキル基、または炭素数６ないし１４の置換もしくは無
置換のアリール基を表わし、ＺｌおよびＺ２は各式中の
窒素またはリン原子と結合して５員または６員環を形成
する非金属原子群を表わす。In the formula, R′1, R12, Rl 3, Rth, R”% R1
6, R'', R18, RI9, R'', R'' and R22 each represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, and Zl and Z2 represents a group of nonmetallic atoms that combine with the nitrogen or phosphorus atom in each formula to form a 5- or 6-membered ring.
この炭素数１ないし２０の置換もしくは無置換のアルキ
ル基として、たとえばメチル基、エチル基、ｎ−ブチル
基、１ｓｏ−アミル基、ｎ−ドデシル基、ｎ−オクタデ
シル基などをあげることができる。炭素数６ないし１４
のアリール基としては、たとえばフェニル基、トリル基
、α−ナフチル基などをあげることができる。Examples of the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, n-butyl group, 1so-amyl group, n-dodecyl group, and n-octadecyl group. Carbon number 6 to 14
Examples of the aryl group include phenyl group, tolyl group, and α-naphthyl group.
これらのアルキル基またはアリール基はシアノ基、水酸
基、炭素数１ないし２０のアルキル基〈たとえばメチル
基、エチル基、ｎ−ブチル基、ｎ−オクチル基など）、
炭素数６ないし１４のアリール基（たとえば、フェニル
基、トリル基、α−ナフチル基など）、炭素数２ないし
２０のアシルオキシ基（たとえばアセトキシ基、ベンゾ
イルオキシ基またはｐ−メトキシベンゾイルオキシ基な
ど）、炭素数１ないし６のアルコキシ基（たとえばメト
キシ基、エトキシ基、プロポキシ基、ブトキシ基など）
、アリーロキシ基（たとえば、フェノキシ基、トリロキ
シ基など）、アラルキル基（たとえば、ベンジル基、フ
ェネチル基またはアニシル基など）、アルコキシカルボ
ニル基（タトえば、メトキシカルボニル基、エトキシカ
ルボニル基、ｎ−ブトキシカルボニル基など）、アリー
ロキシカルボニル基（たとえば、フェノキシカルボニル
基、トリロキシカルボニル基など）、アシル基（たとえ
ば、アセチル基、ベンゾイル基など）、アシルアミノ基
（たとえば、アセチルアミノ基、ベンゾイルアミノ基な
ど）、カルバモイル基（りとえば、Ｎ−エチルカルバモ
イルＬ Ｎ−フェニルカルバモイル基すど）、アルキル
スルホニルアミノ基（たとえば、メチルスルホニルアミ
ノ基、フェニルスルホニルアミノ基ナト）、スルファモ
イル基（たとえば、Ｎ−エチルスルファモイル基、Ｎ−
フェニルスルファモイル基など）、スルホニル基（たと
えば、メシル基、トシル基など）などで置換されていて
もよい。These alkyl groups or aryl groups include cyano groups, hydroxyl groups, alkyl groups having 1 to 20 carbon atoms (for example, methyl groups, ethyl groups, n-butyl groups, n-octyl groups, etc.),
Aryl groups having 6 to 14 carbon atoms (for example, phenyl group, tolyl group, α-naphthyl group, etc.), acyloxy groups having 2 to 20 carbon atoms (for example, acetoxy group, benzoyloxy group, p-methoxybenzoyloxy group, etc.), Alkoxy group having 1 to 6 carbon atoms (for example, methoxy group, ethoxy group, propoxy group, butoxy group, etc.)
, aryloxy group (for example, phenoxy group, triloxy group, etc.), aralkyl group (for example, benzyl group, phenethyl group, or anisyl group, etc.), alkoxycarbonyl group (for example, methoxycarbonyl group, ethoxycarbonyl group, n-butoxycarbonyl group) ), aryloxycarbonyl group (e.g., phenoxycarbonyl group, triloxycarbonyl group, etc.), acyl group (e.g., acetyl group, benzoyl group, etc.), acylamino group (e.g., acetylamino group, benzoylamino group, etc.), carbamoyl group groups (for example, N-ethylcarbamoyl, N-phenylcarbamoyl, etc.), alkylsulfonylamino groups (for example, methylsulfonylamino, phenylsulfonylamino), sulfamoyl groups (for example, N-ethylsulfamoyl) group, N-
phenylsulfamoyl group, etc.), sulfonyl group (eg, mesyl group, tosyl group, etc.).
またｚｌおよびＺ２は前記のように５員環または６員環
を形成するのに必要な非金属原子群を表わす。これらの
５員環もしくは６員環としては、ピリジン環、イミダゾ
ール環、ビロール環、２−ピロリン環、ピロリジン環、
ピペリジン環、ピラゾール環、ピラゾリン環、イミダシ
リン環などをあげることができる。一般式（ＩＶ−ｂ）
で表わされるカチオンとしては、たとえばドデシルピリ
ジニウム基、ヘキサデシルピリジニウム基、ドデシルイ
ミダゾリウム基などをあげることができる。Further, zl and Z2 represent a group of nonmetallic atoms necessary to form a 5-membered ring or a 6-membered ring as described above. These 5-membered rings or 6-membered rings include a pyridine ring, an imidazole ring, a virol ring, a 2-pyrroline ring, a pyrrolidine ring,
Examples include a piperidine ring, a pyrazole ring, a pyrazoline ring, and an imidacilline ring. General formula (IV-b)
Examples of the cation represented by the formula include dodecylpyridinium group, hexadecylpyridinium group, and dodecylimidazolium group.
一般式（ＩＶ−ｃ）で表わされるカチオンとしては、た
とえば、Ｎ−エチル−Ｎ−ヘキサデシルピペリジニウム
基、Ｎ−エチル−Ｎ−ドデシルピラゾリジニウム基など
をあげることができる。Examples of the cation represented by general formula (IV-c) include N-ethyl-N-hexadecylpiperidinium group and N-ethyl-N-dodecylpyrazolidinium group.
上記の一般式（ＩＶ−ａ）、（ｒＶ−ｂ）、（ｒＶ−Ｃ
）、（Ｉ’Ｖ−ｄ）および（ＩＶ−ｅ）で表わされる陽
イオンの中で、本発明に特に好ましく用いられるものは
、製造原料の人手し易さ、製造コストの点で、（ＩＶ−
ａ）、（ｒＶ−ｂ）、（ＩＶ−ｄ）右よび（ＩＶ−ｅ）
である。The above general formulas (IV-a), (rV-b), (rV-C
), (I'V-d) and (IV-e), those particularly preferably used in the present invention are (IV −
a), (rV-b), (IV-d) right and (IV-e)
It is.
この陽イオン（Ｃａｔ、）および［Ｃａｔ２’］の種類
は、前記一般式〔■〕またはＣＩ［Ｉ］で表わされる化
合物の有機溶媒に対する溶解性に影響を及ぼす。The types of the cations (Cat, ) and [Cat2'] affect the solubility of the compound represented by the general formula [■] or CI[I] in organic solvents.
一般：：、第四級へテロ原子に結合する置換基がアルキ
ル基のとき、その鎖長が長くなるほど溶解度が高くなり
、特にテトラアルキル置換アンモニウムもしくはホスホ
ニウムの場合この傾向が著しく、アンモニウムカチオン
の場合は炭素数の合計が１７以上のカチオンが、またホ
スホニウムカチオンの場合は炭素数の合計が４以上のカ
チオンが高い溶解性を与える。General:: When the substituent bonded to a quaternary heteroatom is an alkyl group, the longer the chain length, the higher the solubility.This tendency is particularly remarkable in the case of tetraalkyl-substituted ammonium or phosphonium, and in the case of ammonium cations. In the case of phosphonium cations, cations having a total number of carbon atoms of 17 or more provide high solubility, and in the case of phosphonium cations, cations having a total number of carbon atoms of 4 or more provide high solubility.
前記一般式〔■〕または〔■〕で表わされる化合物にお
いてＭｌまたはＭｌを好ましい順に挙げルトニッケル、
コバルト、銅、パラジウム、白金の順である。In the compound represented by the general formula [■] or [■], Ml or Ml are listed in the order of preference, rutnickel,
The order is cobalt, copper, palladium, and platinum.
一般式〔■〕または〔■〕の金属錯体は平面四配位の立
体構造を有する。なお一般式ＣＩＩＩ）の化合物ではチ
オケトン基が中心金属に関して対称又は非対称にあるか
は一義的に決らないが、この明細書では便宜的に一般式
〔ＩＩＩ）のように表わす。The metal complex of the general formula [■] or [■] has a three-dimensional structure with four-planar coordination. In the compound of general formula CIII), it is not unambiguously determined whether the thioketone group is symmetrical or asymmetrical with respect to the central metal, but it is expressed as general formula [III) for convenience in this specification.
前記一般式［ＩＩＥまたは〔Ｉ］で表わされる化合物は
次のようにして合成することができる。The compound represented by the general formula [IIE or [I] can be synthesized as follows.
一般式［ｎ）（ｎ＝２）の化合物は二硫化炭素とナトリ
ウムを反応させて得られるジンディラム−１，３−ジチ
オール−２−チオン−４，５−ジチオレートを先ず、亜
鉛錯体とし、これに塩化ベンゾイルを反応させ、ビスベ
ンゾイルチオ体トスる。これをアルカリで分解した後、
金属塩を反応させて得られる。The compound of the general formula [n) (n=2) is obtained by first converting jindiram-1,3-dithiol-2-thione-4,5-dithiolate obtained by reacting carbon disulfide and sodium into a zinc complex. React benzoyl chloride and toss bisbenzoylthio form. After decomposing this with alkali,
Obtained by reacting metal salts.
又、一般式ＣＩ［）（ｎ＝１）の化合物は、上で得られ
た錯体（ｎ＝２）を適当な酸化剤で酸化して得られる。Further, the compound of the general formula CI[) (n=1) can be obtained by oxidizing the complex (n=2) obtained above with a suitable oxidizing agent.
一般式（ＩＩＩＩ （ｎ＝２）の化合物は、先ず、二
硫化炭素とナトリウムを反応させて得られるジンディラ
ム−１，３−ジチオール−２−チオン−４゜５−ジチオ
レートを、約１３０℃に加熱してジンディラム−１，２
−ジチオール−３−チオン−４゜５−ジチオレートに異
性化させる。これを亜鉛錯体とし、これに塩化ベンゾイ
ルを反応させ、ビスベンゾイルチオ体とする。これをア
ルカリで分解した後、金属塩を反応させて得られる。The compound of general formula (III (n=2) is prepared by first heating zindiram-1,3-dithiol-2-thione-4°5-dithiolate obtained by reacting carbon disulfide and sodium to about 130°C. jindiram-1,2
-dithiol-3-thione-4°5-dithiolate is isomerized. This is made into a zinc complex, and this is reacted with benzoyl chloride to form a bisbenzoylthio compound. It is obtained by decomposing this with an alkali and then reacting it with a metal salt.
又、一般式（ＩＩＩＩ （ｎ＝１）は上で得られた錯
体（ｎ＝２）を適当な酸化剤で酸化して得られる。Further, general formula (III (n=1)) can be obtained by oxidizing the complex (n=2) obtained above with a suitable oxidizing agent.
一般式〔■〕または〔■〕の化合物を得るための中間体
である１、３−ジチオール−２−チオン−４，５−ジチ
オレートアニオンは、上記の如く〜ａによる還元法の他
に電気化学的な還元によっても得られる。The 1,3-dithiol-2-thione-4,5-dithiolate anion, which is an intermediate for obtaining the compound of the general formula [■] or [■], can be produced by electrolysis in addition to the reduction method according to ~a as described above. It can also be obtained by chemical reduction.
前記一般式〔■〕で表わされる化合物のうち好ましいも
のを例示すれば次の通りである。Preferred examples of the compounds represented by the general formula [■] are as follows.
Ｍ ／””’ｌ
Ｍ
Ｍ−ロ ＃ミ
一般式（ＩＩ）で表わされる化合物の合成例を以下に示
す。M/””'l
M
A synthesis example of the compound represented by the general formula (II) is shown below.
合成例１〈例示化合物（ＩＩ−４）の合成〉（１−１）
ビス（テトラエチルアンモニウム）−ビス（１，３−ジ
チオール−２−チオン−４゜５−ジチオラト）亜鉛錯体
の合成。Synthesis Example 1 <Synthesis of Exemplary Compound (II-4)> (1-1)
Synthesis of bis(tetraethylammonium)-bis(1,3-dithiol-2-thione-4°5-dithiolato)zinc complex.
反応操作はすべてアルゴン雰囲気下で行った。All reaction operations were performed under an argon atmosphere.
ナトリウム２３ｇを小片に切り、二硫化炭素１８０ｍ１
中に分散した後、これに撹拌しつつジメチルホルムアミ
ド２００ｍｆをゆっくり滴下した。この時激しく発熱し
ないように注意する。ジメチルホルムアミドを滴下終了
後、注意しながら、おだやかに加熱して２４時間還流し
た。反応終了後未反応のナトリウムをろ別した。次いで
ろ液にエタノール５０ｍ１を加え、室温で２時間撹拌し
た。この溶液から二硫化炭素を室温で減圧留去する。次
いで水３００ｍ１をゆっくり滴下して加えた後得られた
溶液をろ過した。Cut 23g of sodium into small pieces and add 180ml of carbon disulfide.
After being dispersed in the solution, 200 mf of dimethylformamide was slowly added dropwise to the solution while stirring. Be careful not to generate too much heat at this time. After dropping dimethylformamide, the mixture was carefully heated and refluxed for 24 hours. After the reaction was completed, unreacted sodium was filtered off. Next, 50 ml of ethanol was added to the filtrate, and the mixture was stirred at room temperature for 2 hours. Carbon disulfide is distilled off from this solution under reduced pressure at room temperature. Then, 300 ml of water was slowly added dropwise and the resulting solution was filtered.
次いで、あらかじめ塩化亜鉛２０ｇをメタノール５００
＋＋１ｊ２に溶かし、これに濃アンモニウム水５００ｍ
１を加えた溶液を調製しておき、これを上記の反応溶液
に加え（室温）５分間撹拌した後、テトラエチルアンモ
ニウムプロミド５３ｇを水２５０ｍβに溶かした水溶液
を加えると、直ちに赤色の沈殿が析出してくる。これを
ろ過し、風乾して亜鉛錯体を得た。Next, add 20 g of zinc chloride to 500 g of methanol in advance.
++1j2 and add 500ml of concentrated ammonium water to this.
1 was added, and this was added to the above reaction solution and stirred for 5 minutes (at room temperature). When an aqueous solution of 53 g of tetraethylammonium bromide dissolved in 250 mβ of water was added, a red precipitate immediately precipitated. I'll come. This was filtered and air-dried to obtain a zinc complex.
（１−２＞４．５−ビス（ベンゾイルチオ）−１，３−
ジチオール−２−チオンの合成。(1-2>4.5-bis(benzoylthio)-1,3-
Synthesis of dithiol-2-thione.
（１−１）で得た亜鉛錯体２２ｇをアセトン５００ｍｊ
！に溶かしろ過する。ろ液を撹拌しつつ、これに塩化ベ
ンゾイル１５０ｍｆを加える。直ちに黄色の沈殿が析出
する。ろ過、水洗機風乾して標記化合物１６ｇを得た。22g of the zinc complex obtained in (1-1) was added to 500mj of acetone.
! Dissolve and filter. While stirring the filtrate, add 150 mf of benzoyl chloride. A yellow precipitate immediately separates out. After filtration and air drying in a water washer, 16 g of the title compound was obtained.
（１−３）例示化合物（ＩＩ−４）の合成（１−２）で
得たビス（ベンゾイルチオ）体９．２ｇをメタノール５
０＋ｎｊ！に溶かす。これにナトリウムメトキサイドの
２８％メタノール溶液６．３ｇを加えて、１０分間撹拌
する。この溶液に塩化ニッケル（六水和物）２．４ｇを
メタノール５０ｍ１に溶かした溶液を加え、室温で３０
分間撹拌する。この溶液にテトラブチルホスホニウムプ
ロミド８．５ｇをメタノール１００ｍβに溶かした溶液
を加えると、直ちに黒色の沈殿が析出する。(1-3) Synthesis of Exemplified Compound (II-4) 9.2 g of the bis(benzoylthio) compound obtained in (1-2) was added to
0+nj! dissolve in To this was added 6.3 g of a 28% methanol solution of sodium methoxide, and the mixture was stirred for 10 minutes. A solution of 2.4 g of nickel chloride (hexahydrate) dissolved in 50 ml of methanol was added to this solution, and the solution was heated to 30 mL at room temperature.
Stir for a minute. When a solution of 8.5 g of tetrabutylphosphonium bromide dissolved in 100 mβ of methanol is added to this solution, a black precipitate is immediately deposited.
さらに２０分間撹拌してろ過し、アセトンで洗って風乾
し、アセトン−イソプロピルアルコールから再結晶させ
て標記化合物を得た。収量３．８ｇ合成例２く例示化合
物（ｎ−２）の合成〉（１−３）で得られたニッケル錯
体１ｇをアセトン６０ｍｆに溶かし、これに酢酸３０ｍ
ｆを加え、３時間撹拌し溶媒を留去したところ黒色の結
晶が析出した。これをアセトン−メタノールから再結晶
させて、目的の例示化合物（ＩＩ−２）を得た。収量０
．４ ｇ、 ｍ、ｐ、 １８５℃ λｗａｘ ： １
１２５ｎｍ。Stir for an additional 20 minutes, filter, wash with acetone, air dry, and recrystallize from acetone-isopropyl alcohol to give the title compound. Yield: 3.8 g Synthesis Example 2 Synthesis of Exemplified Compound (n-2) 1 g of the nickel complex obtained in (1-3) was dissolved in 60 mf of acetone, and 30 mf of acetic acid was added to this.
f was added, stirred for 3 hours, and the solvent was distilled off to precipitate black crystals. This was recrystallized from acetone-methanol to obtain the target exemplary compound (II-2). Yield 0
．． 4 g, m, p, 185℃ λwax: 1
125nm.
ε□、：２．５ＬｘｌＯ’ （ＣＨｚＣｊｉｚ中）ま
た既知のクエンチャ−としては、特開昭５９−１７８２
９５号に記載されている。次の化合物が挙げられる。ε□, :2.5LxlO' (in CHzCjiz) Also, known quenchers include JP-A-59-1782
It is described in No. 95. The following compounds may be mentioned.
（ｉ）ビスジチオ−α−ジケトン系
Ｒ’−Ｒ’はアルキル基またはアリール基を表わし、Ｍ
は２価の遷移金属原子を表わす。(i) Bisdithio-α-diketone system R'-R' represents an alkyl group or an aryl group, and M
represents a divalent transition metal atom.
（ｉｉ ）ビスフェニルジチオール系
Ｒ５ＳＲ＠はアルキル基またはハロゲン原子を表わし、
Ｍは２価の遷移金属子を表わす。(ii) Bisphenyldithiol system R5SR@ represents an alkyl group or a halogen atom,
M represents a divalent transition metal.
（ｉｉｉ ）アセチルアセトナートキレート系（ｉｖ）
ジチオカルバミン酸キレート系（ｖ）ビスフェニルチオ
ール系
（ｖｉ）チオカテコールキレート系
（ｖｊ）サリチルアルデヒドオキシム系（ｖｉｉＩ）チ
オビスフェルレートキレート系（ｉｘ）亜ホスホン酸キ
レート系
（ｘ）ベンゾエート系
（×１）ヒンダードアミン系
（Ｘ ｉ ｉ）遷移金属塩
この数次式で表わされるアミニウム系もしくはジイモニ
ウム系化合物が挙げられ、具体例としては日本化薬株式
会社製ｒＲＧ−００２、ＩＲＧ−〇〇３、ＩＲＧ−０２
２、ＩＲＧ−０３３が挙げられる。(iii) Acetylacetonate chelate system (iv)
Dithiocarbamate chelate system (v) Bisphenylthiol system (vi) Thiocatechol chelate system (vj) Salicylaldehyde oxime system (viiI) Thiobisferrate chelate system (ix) Phosphonous acid chelate system (x) Benzoate system (x1 ) Hindered amine type (X i i) Transition metal salt Examples include aminium type or diimonium type compounds represented by this mathematical formula, and specific examples include rRG-002, IRG-〇〇3, and IRG- manufactured by Nippon Kayaku Co., Ltd. 02
2, IRG-033.
○ ＮＲ。○ N.R.
（式中Ｒはアルキル基又はアリール基を表わす。）本発
明において、前記色素のカチオンと、クエンチャ−のア
ニオンとの結合体を使用することもできる。(In the formula, R represents an alkyl group or an aryl group.) In the present invention, a combination of a cation of the dye and an anion of a quencher can also be used.
クエンチャ−は前記色素１モルあたり、一般に０．０５
〜１２モノへ好ましくは０．１〜１．２モル使用される
。The quencher is generally 0.05% per mole of the dye.
to 12 monomers, preferably 0.1 to 1.2 moles are used.
クエンチャ−は色素薄膜記録層に含有させることが好ま
しいが、記録層とは別の層に含有させてもよい。本発明
の光記録媒体には、必要により、さらに基板上に下引き
層を、また記録層上に保護層を、また基板上もしくは記
録層上に反射層を設けることができる。The quencher is preferably contained in the dye thin film recording layer, but may be contained in a layer separate from the recording layer. The optical recording medium of the present invention may further be provided with a subbing layer on the substrate, a protective layer on the recording layer, and a reflective layer on the substrate or the recording layer, if necessary.
基板としては既知のものを任意に使用することができる
。その代表的な例にはガラスまたはプラスチックがあり
、プラスチックとしてはアクリノベポリカーボネート、
ポリスルホン、ポリイミド、非晶質ポリオレフィン、エ
ポキシ樹脂、ポリエステルなどが用いられる。その形状
はディスク状、カード状、シート状、ロールフィルム状
など種々のものが可能である。Any known substrate can be used as the substrate. Typical examples include glass or plastic; plastics include acrinove polycarbonate,
Polysulfone, polyimide, amorphous polyolefin, epoxy resin, polyester, etc. are used. Its shape can be various, such as a disk, card, sheet, or roll film.
ガラスまたはプラスチック基板には記録時のトラッキン
グを容易にするために案内溝を形成させてもよい。また
ガラスまたはプラスチック基板にはプラスチックバイン
ダーまたは無機酸化物、無機硫化物などの下引き層を設
けてもよい。基板よりも熱伝導率の低い下引き層が好ま
しい。また記録層同士を内側にして２枚の記録媒体を対
向させたいわゆるエアーサンドイッチ構造にすることも
可能である。A guide groove may be formed on the glass or plastic substrate to facilitate tracking during recording. Furthermore, a subbing layer such as a plastic binder, an inorganic oxide, an inorganic sulfide, etc. may be provided on the glass or plastic substrate. An undercoat layer having a lower thermal conductivity than the substrate is preferred. It is also possible to form a so-called air sandwich structure in which two recording media are placed facing each other with their recording layers facing each other.
本発明における記録層の形成は、例えば、一般式（Ｉ）
で表わされる色素およびクエンチャ−を有機溶剤（例え
ばメタノール、エタノール、イソプロピルアルコール、
２． ２． ３． ３−テトラフルオロプロパツールな
どのフッ素化アルコール類、ジクロロメタン、ジクロロ
エタン、アセトンなど）に溶解し、必要に応じて適当な
バインダー（例えばＰＶＡ、、ＰＶＰ、ポリビニルブチ
ラール、ポリカーボネート、ニトロセルロース、ポリビ
ニルホルマール、メチルビニルエーテル、塩素化パラフ
ィン、無水マレイン酸共重合体、スチレン−ブタジェン
共重合体、キシレン系樹脂）を加え、この溶液を塗布（
例えばスピンコード）することによって行なえるし、又
は色素とクエンチャ−を共蒸着するかあるいは一般式（
ｉ）で表わされる色素を真空蒸着したのち、クエンチャ
−を塗布することによって行なえる。バインダーを使用
する場合には、バインダーの重量は色素重量の０．０１
〜２倍が好ましい。また一般式（Ｉ）の色素をいわゆる
ラングミュア−プロジェット法により薄膜として用いる
こともできる。The formation of the recording layer in the present invention can be carried out, for example, by formula (I)
The dye and quencher represented by
2. 2. 3. fluorinated alcohols such as 3-tetrafluoropropanol, dichloromethane, dichloroethane, acetone, etc.), and optionally a suitable binder (e.g., PVA, PVP, polyvinyl butyral, polycarbonate, nitrocellulose, polyvinyl formal, methyl vinyl ether, chlorinated paraffin, maleic anhydride copolymer, styrene-butadiene copolymer, xylene resin) and apply this solution (
For example, it can be done by spin-coding), or by co-depositing the dye and quencher, or by using the general formula (
This can be done by vacuum depositing the dye represented by i) and then applying a quencher. If a binder is used, the weight of the binder is 0.01 of the weight of the dye.
~2 times is preferred. The dye of general formula (I) can also be used in the form of a thin film by the so-called Langmuir-Prodgett method.
本発明における記録層は１層又は２Ｎ以上設ける。The recording layer in the present invention is one layer or 2N or more.
記録層内又はこれに隣接する層内には、色素の劣化を防
ぐため、酸化防止剤もしくは褪色防止剤を存在させても
よい。An antioxidant or anti-fading agent may be present in the recording layer or in a layer adjacent thereto to prevent deterioration of the dye.
記録層の膜厚は、通常０．０１μｍ〜２μｍ、好ましく
は０．０２〜０，８μｍの範囲である。反射読出しの場
合は特に好ましくは読出しに使用するレーザ波長の％の
奇数倍である。The thickness of the recording layer is usually in the range of 0.01 μm to 2 μm, preferably 0.02 to 0.8 μm. In the case of reflective readout, it is particularly preferably an odd multiple of % of the laser wavelength used for readout.
半導体レーデまたはＨｅ−Ｎｅレーザなどの反射層を設
ける場合は、基板に反射層を設は次にこの反射層の上に
前述したような方式によって記録層を設けることによる
か、あるいは基板に記録層を設け、次いでこの上に反射
層を設けるかのいずれかの方法がある。When a reflective layer is provided for a semiconductor laser or a He-Ne laser, the reflective layer is provided on the substrate and then a recording layer is provided on the reflective layer using the method described above, or the recording layer is placed on the substrate. There is a method of providing a reflective layer and then providing a reflective layer thereon.
反射層は蒸着法、スパッタリング法、イオンブレーティ
ング法などの他、次のような方法によって作ることがで
きる。The reflective layer can be made by the following methods, in addition to vapor deposition, sputtering, and ion blating.
例えば水溶性樹脂（ＰＶＰＳＰＶＡなど）に金属塩また
は、金属錯塩を溶解させ、さらに、還元剤を加えた溶液
を基板に塗布し、５０℃〜１５０℃好ましくは６０℃〜
１００℃で加熱乾燥させることによって形成される。For example, a solution containing a metal salt or a metal complex salt dissolved in a water-soluble resin (PVPSPVA, etc.) and a reducing agent added thereto is applied to the substrate, and the solution is applied at 50°C to 150°C, preferably from 60°C to
It is formed by heating and drying at 100°C.
樹脂に対する金属塩または金属錯塩の量は重量比で０．
１〜１０好ましくはＯ１５〜１．５である。この際、記
録層の膜厚は金属粒子反射層が０，０１〜０．１μｍで
ありそして光吸収層が０．０１〜１μｍの範囲が適当で
ある。The weight ratio of the metal salt or metal complex salt to the resin is 0.
1 to 10, preferably O15 to 1.5. In this case, the appropriate thickness of the recording layer is 0.01 to 0.1 .mu.m for the metal particle reflective layer and 0.01 to 1 .mu.m for the light absorption layer.
金属塩または金属錯塩としては、硝酸銀、シアン化銀カ
リウム、シアン化金カリウム、銀アンミン錯体、銀シア
ン錯体、金塩または金シアン錯体などを使用できる。還
元剤としてはホルマリン、酒石酸、酒石酸塩、還元剤、
次亜燐酸塩、水素化ｌｊ票ナナトリウムジメチルアミン
ボランなどを使用できる。還元剤は金属塩または金属錯
塩１モルに対し０．２〜１０モル好ましくは０．５〜４
モルの範囲で使用できる。As the metal salt or metal complex salt, silver nitrate, potassium silver cyanide, potassium gold cyanide, silver ammine complex, silver cyanide complex, gold salt, or gold cyanide complex can be used. As a reducing agent, formalin, tartaric acid, tartrate, reducing agent,
Hypophosphite, hydrogenated sodium dimethylamine borane, etc. can be used. The reducing agent is used in an amount of 0.2 to 10 mol, preferably 0.5 to 4 mol, per 1 mol of metal salt or metal complex salt.
Can be used in a molar range.
本発明の光記録媒体において、情報の記録はレーザ（例
えば半導体レーザ、Ｈｅ−Ｎｅレーザなど）などのスポ
ット状の高エネルギービームを基板を通しであるいは基
板と反対側より記録層に照射することにより行われ、記
録層に吸収された光が熱に変換され、記録層にピット（
穴）が形成される。In the optical recording medium of the present invention, information is recorded by irradiating the recording layer with a spot-like high-energy beam of a laser (e.g., semiconductor laser, He-Ne laser, etc.) through the substrate or from the opposite side of the substrate. The light absorbed by the recording layer is converted into heat, and pits (
hole) is formed.
また情報の読み出しはレーザビームを記録の闇値エネル
ギー以下の低出力で照射し、ピット部とピットが形成さ
れていない部分の反射光量もしくは透過光量の変化を検
出することにより行われる。Information is read out by irradiating a laser beam with a low output power below the recording darkness value and detecting changes in the amount of reflected light or transmitted light in the pit portion and the portion where no pits are formed.
以下、実施例により本発明を更に詳細に説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
表１に示す色素、クエンチャ−１及び成る場合にはバイ
ンダをメタノール−メチルエチルケトン−ジクロロエタ
ンからなる適当な比率の混合溶媒に溶解し、表面硬化し
たグループ付く１．６μピツチ、深さ７５０人）ポリカ
ーボネート基板に厚さ０．１μｍとなるようにスピンナ
ーで塗布し、乾燥した。なお色素とクエンチャ−との重
量比は３：１、バインダを用いる場合には、バインダの
重量は色素の１７５とした。Example 1 The dye shown in Table 1, Quencher 1, and binder, if present, were dissolved in a mixed solvent of methanol, methyl ethyl ketone, and dichloroethane in an appropriate ratio, and prepared in a 1.6μ pitch with surface-hardened groups, at a depth of 750 people. ) It was coated on a polycarbonate substrate with a spinner to a thickness of 0.1 μm and dried. The weight ratio of the dye to the quencher was 3:1, and when a binder was used, the weight of the binder was 175% of the weight of the dye.
評価条件は下記のとおりであった。The evaluation conditions were as follows.
（記録及び再生）
レーザ ：半導体レーザ（ＧａＡ Ｉ Ａｓ）
レーザの波長 ニア８０ｎｍ
レーザのビーム径：１．６μｍ
線速 ：５ｍ／ｓ
記録パワー ：３ｍｌ！
記録周波数 ＋ ２．５ ＭＨｚ
記録デユーティ−＝５０％
再生パワー ：０．４ｎ＋Ｗ
く再生劣化の評価）
再生パワー ：１．ＯｍＷ
再生回数 ：１０５回
（保存時劣化の評価）
保存温湿度 ＝６０℃ ９０％ＲＨ保存時間
二３０日間
結果を表１に示す。(Recording and playback) Laser: Semiconductor laser (GaA I As)
Laser wavelength: Near 80nm Laser beam diameter: 1.6μm Linear velocity: 5m/s Recording power: 3ml! Recording frequency + 2.5 MHz Recording duty -=50% Reproduction power: 0.4n+W Evaluation of reproduction deterioration) Reproduction power: 1. OmW Number of plays: 105 times (evaluation of deterioration during storage) Storage temperature and humidity = 60℃ 90%RH Storage time
The results for 230 days are shown in Table 1.
比較化合物Ａ
〔発明の効果〕
表１の結果から、本発明の光学的情報記録媒体はＣ／
Ｎの高い十分な記録特性を有し、長期の保存あるいは長
時間の読み取りに対して高い安定性を有することが明ら
かである。Comparative Compound A [Effect of the Invention] From the results in Table 1, the optical information recording medium of the present invention is C/
It is clear that it has sufficient recording properties with high N and high stability for long-term storage or long-term reading.
Claims (1)
ための光学的情報記録媒体であって、基板上に、オキソ
ノール色素を担持せしめたことを特徴とする光学的情報
記録媒体。（２）オキソノール色素が下記一般式（ I
）で表わされる色素であることを特徴とする特許請求の
範囲第（１）項記載の光学的情報記録媒体。 一般式（ I ） ▲数式、化学式、表等があります▼ 〔式中、Ｙ、Ｚは炭素環もしくは複素環を形成するのに
必要な原子団を表わし、Ｌは置換されていてもよいメチ
ン基、または共役二重結合で連結された置換されていて
もよいポリメチン鎮を完成する原子団を表わし、Ａ、Ｑ
は共役二重結合鎖を完成する原子団を表わし、ｍ、ｎは
それぞれ独立に０もしくは１を表わす。〕 （３）基板上に、オキソノール色素とさらに一重項酸素
クェンチャーを担持せしめたことを特徴とする特許請求
の範囲第（１）項または第（２）項記載の光学的情報記
録媒体。[Scope of Claims] (1) An optical information recording medium for recording, reproducing, and erasing using a laser beam, characterized in that an oxonol dye is supported on a substrate. (2) The oxonol dye has the following general formula (I
) The optical information recording medium according to claim 1, wherein the optical information recording medium is a dye represented by: General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. , or represents an atomic group that completes an optionally substituted polymethine compound connected with a conjugated double bond, A, Q
represents an atomic group that completes a conjugated double bond chain, and m and n each independently represent 0 or 1. (3) The optical information recording medium according to claim (1) or (2), characterized in that an oxonol dye and a singlet oxygen quencher are supported on the substrate.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62044870A JPS63209995A (en) | 1987-02-27 | 1987-02-27 | Optical data recording medium |
| US07/161,474 US4968593A (en) | 1987-02-27 | 1988-02-26 | Optical information recording medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62044870A JPS63209995A (en) | 1987-02-27 | 1987-02-27 | Optical data recording medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63209995A true JPS63209995A (en) | 1988-08-31 |
Family
ID=12703531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62044870A Pending JPS63209995A (en) | 1987-02-27 | 1987-02-27 | Optical data recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63209995A (en) |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0962923A1 (en) | 1998-06-04 | 1999-12-08 | Fuji Photo Film Co., Ltd. | Information recording medium and novel oxonol compound |
| US6670475B2 (en) | 1996-09-30 | 2003-12-30 | Fuji Photo Film Co., Ltd. | Information recording medium |
| US6713147B2 (en) | 2001-02-21 | 2004-03-30 | Fuji Photo Film Co., Ltd. | Optical information-recording medium and optical information-recording method |
| JP2006001875A (en) * | 2004-06-17 | 2006-01-05 | Fuji Photo Film Co Ltd | Method for producing oxonol compound |
| EP1701347A2 (en) | 2002-11-29 | 2006-09-13 | Fuji Photo Film Co., Ltd. | Optical information-recording Medium, novel oxonol compound and method of recording information |
| WO2006101177A1 (en) * | 2005-03-24 | 2006-09-28 | Fujifilm Corporation | Optical information recording medium |
| WO2007055273A1 (en) | 2005-11-11 | 2007-05-18 | Fujifilm Corporation | Cation compound, dye compound and use thereof, and optical information recording medium |
| WO2007119672A1 (en) | 2006-04-10 | 2007-10-25 | Fujifilm Corporation | Optical recording medium, visible information recording method and use of dye compound |
| US7348125B2 (en) | 2001-08-01 | 2008-03-25 | Fujifilm Corporation | Optical information recording medium and novel immonium compound |
| WO2008108406A1 (en) | 2007-03-05 | 2008-09-12 | Fujifilm Corporation | Compound for photoresist, photoresist solution, and etching method using the photoresist solution |
| WO2008123010A1 (en) | 2007-03-05 | 2008-10-16 | Fujifilm Corporation | Light emitting element, method for manufacturing the light emitting element, optical element and method for manufacturing the optical element |
| EP1998329A2 (en) | 2007-06-01 | 2008-12-03 | Fujifilm Corporation | Optical information recording medium and method of recording information |
| WO2009022442A1 (en) | 2007-08-16 | 2009-02-19 | Fujifilm Corporation | Method for producing medium on which information is recorded by pit pattern |
| WO2009050858A1 (en) | 2007-10-15 | 2009-04-23 | Fujifilm Corporation | Method for cleaning heat mode type recording medium layer, method for manufacturing product having recess and projection, method for manufacturing light emitting element and method for manufacturing optical element |
| WO2009110046A1 (en) | 2008-03-05 | 2009-09-11 | 富士フイルム株式会社 | Method for processing work having photoresist layer |
| WO2009113272A1 (en) | 2008-03-10 | 2009-09-17 | 富士フイルム株式会社 | Mold processing method and mold manufacturing method |
| EP2110814A1 (en) | 2008-04-18 | 2009-10-21 | Fujifilm Corporation | Manufacturing method for a stamper and manufacturing method for an optical information recording medium using the stamper |
| WO2009130846A1 (en) | 2008-04-22 | 2009-10-29 | 富士フイルム株式会社 | Laser exposure method, photoresist layer working method, and pattern molding manufacturing method |
| WO2009136624A1 (en) | 2008-05-09 | 2009-11-12 | 富士フイルム株式会社 | Ultraviolet absorbent composition |
| WO2010023790A1 (en) | 2008-08-29 | 2010-03-04 | 富士フイルム株式会社 | Manufacturing method for pattern-forming body and electromagnetic beam processing apparatus |
| WO2010023789A1 (en) | 2008-08-29 | 2010-03-04 | 富士フイルム株式会社 | Pattern-forming member and method of manufacturing the same |
| WO2010035483A1 (en) | 2008-09-25 | 2010-04-01 | 富士フイルム株式会社 | Optical information recording medium, method for information recording, and azo metal complex dye |
| WO2010041470A1 (en) | 2008-10-10 | 2010-04-15 | 富士フイルム株式会社 | Optical information recording medium, information recording method and photosensitizer |
| EP2216680A2 (en) | 2009-02-04 | 2010-08-11 | FUJIFILM Corporation | Fine particles and method for producing the same |
| EP2219053A1 (en) | 2009-02-04 | 2010-08-18 | FUJIFILM Corporation | Heat-ray reflective film, heat-ray reflective structure, and production method thereof |
| WO2010093062A1 (en) | 2009-02-13 | 2010-08-19 | Fujifilm Corporation | Organic electroluminescence device, and method for producing the same |
-
1987
- 1987-02-27 JP JP62044870A patent/JPS63209995A/en active Pending
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6670475B2 (en) | 1996-09-30 | 2003-12-30 | Fuji Photo Film Co., Ltd. | Information recording medium |
| US6849316B2 (en) | 1996-09-30 | 2005-02-01 | Fuji Photo Film Co., Ltd. | Information recording medium |
| EP0962923A1 (en) | 1998-06-04 | 1999-12-08 | Fuji Photo Film Co., Ltd. | Information recording medium and novel oxonol compound |
| US6713147B2 (en) | 2001-02-21 | 2004-03-30 | Fuji Photo Film Co., Ltd. | Optical information-recording medium and optical information-recording method |
| US7348125B2 (en) | 2001-08-01 | 2008-03-25 | Fujifilm Corporation | Optical information recording medium and novel immonium compound |
| EP1701347A2 (en) | 2002-11-29 | 2006-09-13 | Fuji Photo Film Co., Ltd. | Optical information-recording Medium, novel oxonol compound and method of recording information |
| JP2006001875A (en) * | 2004-06-17 | 2006-01-05 | Fuji Photo Film Co Ltd | Method for producing oxonol compound |
| WO2006101177A1 (en) * | 2005-03-24 | 2006-09-28 | Fujifilm Corporation | Optical information recording medium |
| WO2007055273A1 (en) | 2005-11-11 | 2007-05-18 | Fujifilm Corporation | Cation compound, dye compound and use thereof, and optical information recording medium |
| US8039630B2 (en) | 2005-11-11 | 2011-10-18 | Fujifilm Corporation | Cationic compound, dye compound and method of using the same, and optical information recording medium |
| WO2007119672A1 (en) | 2006-04-10 | 2007-10-25 | Fujifilm Corporation | Optical recording medium, visible information recording method and use of dye compound |
| WO2008108406A1 (en) | 2007-03-05 | 2008-09-12 | Fujifilm Corporation | Compound for photoresist, photoresist solution, and etching method using the photoresist solution |
| WO2008123010A1 (en) | 2007-03-05 | 2008-10-16 | Fujifilm Corporation | Light emitting element, method for manufacturing the light emitting element, optical element and method for manufacturing the optical element |
| EP1998329A2 (en) | 2007-06-01 | 2008-12-03 | Fujifilm Corporation | Optical information recording medium and method of recording information |
| WO2009022442A1 (en) | 2007-08-16 | 2009-02-19 | Fujifilm Corporation | Method for producing medium on which information is recorded by pit pattern |
| WO2009050858A1 (en) | 2007-10-15 | 2009-04-23 | Fujifilm Corporation | Method for cleaning heat mode type recording medium layer, method for manufacturing product having recess and projection, method for manufacturing light emitting element and method for manufacturing optical element |
| WO2009110046A1 (en) | 2008-03-05 | 2009-09-11 | 富士フイルム株式会社 | Method for processing work having photoresist layer |
| WO2009113272A1 (en) | 2008-03-10 | 2009-09-17 | 富士フイルム株式会社 | Mold processing method and mold manufacturing method |
| EP2110814A1 (en) | 2008-04-18 | 2009-10-21 | Fujifilm Corporation | Manufacturing method for a stamper and manufacturing method for an optical information recording medium using the stamper |
| WO2009130846A1 (en) | 2008-04-22 | 2009-10-29 | 富士フイルム株式会社 | Laser exposure method, photoresist layer working method, and pattern molding manufacturing method |
| WO2009136624A1 (en) | 2008-05-09 | 2009-11-12 | 富士フイルム株式会社 | Ultraviolet absorbent composition |
| WO2010023790A1 (en) | 2008-08-29 | 2010-03-04 | 富士フイルム株式会社 | Manufacturing method for pattern-forming body and electromagnetic beam processing apparatus |
| WO2010023789A1 (en) | 2008-08-29 | 2010-03-04 | 富士フイルム株式会社 | Pattern-forming member and method of manufacturing the same |
| WO2010035483A1 (en) | 2008-09-25 | 2010-04-01 | 富士フイルム株式会社 | Optical information recording medium, method for information recording, and azo metal complex dye |
| WO2010041470A1 (en) | 2008-10-10 | 2010-04-15 | 富士フイルム株式会社 | Optical information recording medium, information recording method and photosensitizer |
| EP2216680A2 (en) | 2009-02-04 | 2010-08-11 | FUJIFILM Corporation | Fine particles and method for producing the same |
| EP2219053A1 (en) | 2009-02-04 | 2010-08-18 | FUJIFILM Corporation | Heat-ray reflective film, heat-ray reflective structure, and production method thereof |
| WO2010093062A1 (en) | 2009-02-13 | 2010-08-19 | Fujifilm Corporation | Organic electroluminescence device, and method for producing the same |
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