JPH0375635A - Optical recording medium - Google Patents
Optical recording mediumInfo
- Publication number
- JPH0375635A JPH0375635A JP1211879A JP21187989A JPH0375635A JP H0375635 A JPH0375635 A JP H0375635A JP 1211879 A JP1211879 A JP 1211879A JP 21187989 A JP21187989 A JP 21187989A JP H0375635 A JPH0375635 A JP H0375635A
- Authority
- JP
- Japan
- Prior art keywords
- group
- optionally substituted
- recording medium
- ring
- atom
- 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
- 230000003287 optical effect Effects 0.000 title claims description 45
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical group C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims abstract description 8
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 4
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 4
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical group 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 238000007363 ring formation reaction Methods 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000010410 layer Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- -1 cyanomethyl Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000004040 coloring Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 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
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- KYPOHTVBFVELTG-UHFFFAOYSA-N but-2-enedinitrile Chemical group N#CC=CC#N KYPOHTVBFVELTG-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- BLZKSRBAQDZAIX-UHFFFAOYSA-N 2-methyl-1-benzothiophene Chemical compound C1=CC=C2SC(C)=CC2=C1 BLZKSRBAQDZAIX-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000007606 doctor blade method Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- 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
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-NMQOAUCRSA-N 1,2-dideuteriooxyethane Chemical compound [2H]OCCO[2H] LYCAIKOWRPUZTN-NMQOAUCRSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 229940125904 compound 1 Drugs 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
- 230000001066 destructive effect Effects 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Abstract
Description
【発明の詳細な説明】
[a業上の利用分野]
本発明は光学記録媒体に係り、詳しくは1位及び2位に
光照射によって環化し、シクロヘキサジエン環を形成し
てその光学的性質を変化せしめるような非対称の複素環
を有するエチレン誘導体を使用した光学記録媒体に関す
るものである。Detailed Description of the Invention [Field of Application in Industry A] The present invention relates to an optical recording medium, and more specifically, the present invention relates to an optical recording medium, and more specifically, the 1st and 2nd positions are cyclized by light irradiation to form a cyclohexadiene ring to improve its optical properties. The present invention relates to an optical recording medium using an ethylene derivative having an asymmetric heterocycle that causes a change in the number of rings.
[従来の技術]
近年、フォトクロミック化合物を光学記録材料として用
いようとする研究が盛んに行なわれている。フォトクロ
くツク化合物を光学記録材料として用いるには、次の条
件が満足されることが必要とされる。[Prior Art] In recent years, much research has been conducted on the use of photochromic compounds as optical recording materials. In order to use a photoclock compound as an optical recording material, it is necessary that the following conditions be satisfied.
■ 半導体レーザー感受性を備えること。即ち、発色種
(閉環体)の吸収波長が650nm以上にあること。■ Must be semiconductor laser sensitive. That is, the absorption wavelength of the colored species (closed ring) is 650 nm or more.
■ 非破壊読み出し機能を有すること。■ Have a non-destructive read function.
■ 記録が熱的に安定であること。■ Records must be thermally stable.
■ 繰り返し耐久性に優れること。■ Excellent repeated durability.
■ 高い感度を有すること。■ High sensitivity.
先に、本発明者は上記問題点のうち上記■の半導体レー
ザー感受性及び■の繰り返し耐久性を改良したフォトク
ロミック化合物として、下記ビスインドール系化合物を
提案した。Previously, the present inventor proposed the following bisindole-based compound as a photochromic compound that improves the semiconductor laser sensitivity (1) and the repeated durability (2) among the above problems.
しn3 1.++13発色種(閉環体
)
その他のフォトクロミック化合物として、下記ジベンゾ
チオフェン系化合物も提案されてい発色種
(閉環体)
[発明が解決しようとする課題]
上記フォトクロミック化合物のうち、[A]のビスイン
ドール系化合物は記録材料で特に重要な■の記録の熱安
定性が劣るという問題点があった。Shinn3 1. ++13 Color-forming species (closed ring) As other photochromic compounds, the following dibenzothiophene compounds have also been proposed.Color-forming species (closed ring) [Problem to be solved by the invention] Among the above photochromic compounds, bisindole [A] Compounds have a problem in that they have poor thermal stability for recording, which is particularly important in recording materials.
−4、[B]のジベンゾチオフェン系化合物は、■の記
録の熱安定性は優れるが、発色種(閉環体)の吸収波長
は短かく■の半導体レーザー感受性に問題があった。-4, the dibenzothiophene-based compound [B] has excellent thermal stability for recording (2), but the absorption wavelength of the colored species (closed ring) is short, and there is a problem with the semiconductor laser sensitivity (2).
本発明は上記従来の問題点を解決し、光学記録材料に特
に重要な要求特性を満足するフォトクロミック化合物を
用いた高特性光学記録媒体を提供することを目的とする
。It is an object of the present invention to solve the above-mentioned conventional problems and to provide a high-performance optical recording medium using a photochromic compound that satisfies particularly important required properties for optical recording materials.
[課題を解決するための手段及び作用]請求項(1)の
光学記録媒体は、光照射によりその光学的性質を変化さ
せて光学的情報を記録する記録層を有する光学記録媒体
において、該記録層が1位及び2位に光照射によって環
化しシクロヘキサジエン環を形成してその光学的性質を
変化せしめるような非対称の複素環を有する下記一般で
示されるエチレン誘導体を含有することを特徴とする
請求項(2)の光学記録媒体は、請求項(1)の光学記
録媒体において、エチレン誘導体が下記一般式[II
]
一般式
[II! ]
で示されることを特徴とする
請求項(3)の光学記録媒体は、請求項(1)の光学記
録媒体において、エチレン誘導体が下記で示されること
を特徴とする
請求項(4)の光学記録媒体は、請求項(1)の光学記
録媒体において、エチレン誘導体が下記J
Cu2
■
■
即ち、上記構造式■、■で表わされる中間体を合成した
後、化合物■と■を縮合をすることにより本発明に係る
ジシアノエチレン誘導体[III A ]を得ることが
できる。更に、このジシアノエチレン誘導体[III
A ]を加水分解、酸無水物化することにより、本発明
の無水マレイン酸誘導体[III B ]を製造するこ
とができる。[Means and effects for solving the problem] The optical recording medium of claim (1) is an optical recording medium having a recording layer that records optical information by changing its optical properties by irradiation with light. The layer is characterized by containing an ethylene derivative represented by the general formula below, which has an asymmetric heterocycle in the 1st and 2nd positions that is cyclized by light irradiation to form a cyclohexadiene ring and change its optical properties. The optical recording medium according to claim (2) is the optical recording medium according to claim (1), wherein the ethylene derivative has the following general formula [II
] General formula [II! ] The optical recording medium of claim (3) is characterized in that the optical recording medium of claim (1) is characterized in that the ethylene derivative is represented by the following. The recording medium is an optical recording medium according to claim (1), in which the ethylene derivative is the following J Cu2 ■ ■ In other words, after synthesizing an intermediate represented by the above structural formulas ■ and ■, condensing the compounds ■ and ■ Accordingly, the dicyanoethylene derivative [III A ] according to the present invention can be obtained. Furthermore, this dicyanoethylene derivative [III
The maleic anhydride derivative [III B ] of the present invention can be produced by hydrolyzing and converting A ] into an acid anhydride.
化合物■と■との縮合反応は、これらシアノメチル誘導
体を水−有機溶媒中、相関移動触媒の存在下、アルカリ
性中で縮合反応させることにより行なうことができ、ジ
シアノエチレン誘導体[mA]が製造される。The condensation reaction between compounds (1) and (2) can be carried out by subjecting these cyanomethyl derivatives to a condensation reaction in an alkaline environment in the presence of a phase transfer catalyst in a water-organic solvent to produce a dicyanoethylene derivative [mA]. .
化合物■と■との縮合反応に使用される有機溶媒として
はジクロロメタン、クロロホルム、四塩化炭素、テトラ
クロロエタン等のようなハロゲン系溶媒が好ましい。相
関移動触媒としてはテトラブチルアンモニウムブロマイ
ド、テトラブチルアンモニウムアイオダイド、トリエチ
ルベンジルアンモニウムクロライド等が挙げられる。ま
た、使用されるアルカル剤としては水酸化ナトリウム、
水酸化カリウム等が挙げられる。縮合の反応温度は室温
から100℃までが好ましく、特に40〜50℃が好ま
しい。The organic solvent used in the condensation reaction of compounds (1) and (2) is preferably a halogen solvent such as dichloromethane, chloroform, carbon tetrachloride, tetrachloroethane, or the like. Examples of the phase transfer catalyst include tetrabutylammonium bromide, tetrabutylammonium iodide, triethylbenzylammonium chloride, and the like. In addition, the alkaline agents used include sodium hydroxide,
Examples include potassium hydroxide. The reaction temperature for condensation is preferably from room temperature to 100°C, particularly preferably from 40 to 50°C.
次いで、上記ジシアノエチレン誘導体[III A ]
を加水分解、酸無水物化するが、この加水分解、酸無水
物化反応は水又はメタノール、エタノール、エチレング
リコール、エチレングリコールモノメチルエーテル、エ
チレングリコールモノエチルエーテル、ジエチレングリ
コールモノエチルエーテル、N−メチルピロリドン、N
、N−ジメチルホルムアミド、1.3−ジメチル−2−
イミダゾリジノン等の極性溶媒中、水酸化ナトリウム、
水酸化カリウム等のアルカリ剤の存在下、室温からその
溶媒の沸点までの温度に加熱することにより行なうこと
ができる。反応後、酸で中和して生成物を固体として取
り出し、必要に応じてカラムクロマトグラフィー、再結
晶、溶媒懸洗等によって精製することにより、無水マレ
イン酸誘導体[III B ]が得られる。Then, the above dicyanoethylene derivative [III A ]
This hydrolysis and acid anhydride reaction can be carried out using water or methanol, ethanol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, N-methylpyrrolidone, N
, N-dimethylformamide, 1,3-dimethyl-2-
In a polar solvent such as imidazolidinone, sodium hydroxide,
This can be carried out by heating from room temperature to the boiling point of the solvent in the presence of an alkaline agent such as potassium hydroxide. After the reaction, the product is neutralized with an acid and taken out as a solid, and if necessary, purified by column chromatography, recrystallization, solvent suspension washing, etc., to obtain the maleic anhydride derivative [III B ].
本発明に係るエチレン誘導体は、光照射すると下記式に
示すように、複素環Wと複素環W′が環化して、シクロ
ヘキサジエン環を形成し、式[IA]から[IA’]に
示すような構造変化を起こして色変化を起こす。また、
この着色状態は光反応により可逆的に元に戻すことがで
きる。When the ethylene derivative according to the present invention is irradiated with light, the heterocycle W and the heterocycle W' cyclize to form a cyclohexadiene ring as shown in the following formula, and as shown in the formulas [IA] to [IA']. This causes a structural change that causes a color change. Also,
This colored state can be reversibly restored by photoreaction.
[A] [IA’](エチレン誘
導体) (シクロヘキサジエン環を形成)
具体的には、例えば下記式[III B ]で示される
インドリルベンゾチエニルマレイン酸無水物誘導体は、
例えば、488nmのアルゴンイオンレーザ−光を照射
すると、下記に示すような構造変化を起こして、式[1
118’lで示す構造となり、黄色から紫色に変化する
。また、この紫色の着色状態は吸収波長が半導体レーザ
ー域までのびているので、例えば、670nmの半導体
レーザー光を照射することにより下記式のように可逆的
に元の状態に戻すことができる。[A] [IA'] (ethylene derivative) (forms a cyclohexadiene ring) Specifically, for example, an indolylbenzothienyl maleic anhydride derivative represented by the following formula [III B ],
For example, when irradiated with 488 nm argon ion laser light, a structural change occurs as shown below, and the formula [1
The structure becomes 118'l, and the color changes from yellow to purple. Furthermore, since the absorption wavelength of this purple colored state extends to the semiconductor laser range, it can be reversibly returned to its original state as shown in the following formula by irradiating it with, for example, 670 nm semiconductor laser light.
[111B’]
特に、本発明社係るエチレン誘導体は開環状態[IA]
及び着色状態(閉環状態)CIA’]のいずれもが熱的
C安定であり、高温で長時間加熱してもサーモクロくツ
ク反応(熱着色反応)を示さず、また、着色状態も安定
であり、退色反応を示さず、両状態は良好(保持される
。[111B'] In particular, the ethylene derivative according to the present invention is in the open ring state [IA]
and the colored state (ring-closed state) CIA'] are thermally stable, and do not show a thermochromic reaction (thermal coloring reaction) even when heated at high temperatures for a long time, and the colored state is also stable. , shows no fading reaction, and both conditions are good (maintained).
さらに、インドール環をエチレン結合の炭素の片方に持
つ場合には上記開環−閉環による発色−消色の繰り返し
耐久性も良好であり、可逆的な光学記録材料として非常
に有用である。Further, when an indole ring is present on one side of the carbon of the ethylene bond, the durability against repeated coloring and decoloring due to ring opening and closing is good, and the material is very useful as a reversible optical recording material.
次に、このような本発明に係る新規エチレン誘導体を含
有する記録層を有する本発明の光学記録媒体について説
明する。Next, the optical recording medium of the present invention having a recording layer containing the novel ethylene derivative according to the present invention will be described.
本発明の光学記録媒体は、基本的には基板と記録層とか
ら構成されるものであるが、更に必要に応じて基板上に
下引き層を、あるいは、記録層上に保護層を設けること
ができる。The optical recording medium of the present invention basically consists of a substrate and a recording layer, but if necessary, an undercoat layer may be provided on the substrate or a protective layer may be provided on the recording layer. I can do it.
本発明で用いる基板は、使用する光に対して透明又は不
透明のいずれでも良い。基板材料の材質としては、ガラ
ス、プラスチック、紙、板状又は箔状の金属等の、一般
的な記録媒体の支持体が挙げられるが、これらのうち、
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、アクリル樹脂、メタアクリル樹脂、酢酸ビニ
ル樹脂、塩化ビニル樹脂、ニトロセルロース、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
、ポリイミド樹脂、ポリサルホン樹脂等が挙げられる。The substrate used in the present invention may be transparent or opaque to the light used. Examples of the substrate material include supports for general recording media such as glass, plastic, paper, plate-shaped or foil-shaped metals, and among these,
Plastic is preferred from various points of view. Examples of the plastic include acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin, polycarbonate resin, polyimide resin, polysulfone resin, and the like.
本発明の光学記録媒体における情報記録層の膜厚は10
0λ〜100μm1好ましくは1000λ〜10μmと
するのが好適である。The thickness of the information recording layer in the optical recording medium of the present invention is 10
A suitable range is 0λ to 100 μm, preferably 1000λ to 10 μm.
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、キャスト法、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採用することができ
る。As a film forming method, commonly used thin film forming methods such as a vacuum evaporation method, a sputtering method, a doctor blade method, a casting method, a spinner method, and a dipping method can be employed.
本発明の光学記録媒体は、例えば、本発明に係るエチレ
ン誘導体を、必要に応じてポリエステル樹脂、ポリスチ
レン樹脂、ポリビニルブチラール樹脂、ポリ塩化ビニリ
デン、ポリ塩化ビニル、ポリメタクリル酸メチル、ポリ
メタクリル酸ブチル、ポリ酢酸ビニル、酢酸セルロース
、エポキシ樹脂、フェノール樹脂等のバインダーと共に
、四塩化炭素、ベンゼン、シクロヘキサン、メチルエチ
ルケトン、テトラクロロエタン等の溶媒に分散又は溶解
させて、適当な基板上に塗布して記録層を形成すること
によって、或いは、本発明の化合物を公知の蒸着法又は
他の化合物との共蒸着法によって適当な基板上に蒸着し
て記録層を形成することによって、或いは、本発明の化
合物を上述の様な溶媒に溶解し、ガラスセル等に封入す
ること等によって、容易に得ることができる。The optical recording medium of the present invention may contain, for example, the ethylene derivative according to the present invention, if necessary, polyester resin, polystyrene resin, polyvinyl butyral resin, polyvinylidene chloride, polyvinyl chloride, polymethyl methacrylate, polybutyl methacrylate, etc. A recording layer is formed by dispersing or dissolving a binder such as polyvinyl acetate, cellulose acetate, epoxy resin, or phenol resin in a solvent such as carbon tetrachloride, benzene, cyclohexane, methyl ethyl ketone, or tetrachloroethane, and coating it on a suitable substrate. or by depositing the compound of the present invention on a suitable substrate by known vapor deposition methods or co-deposition methods with other compounds to form a recording layer; It can be easily obtained by dissolving it in a solvent such as and sealing it in a glass cell or the like.
なお、スピナー法による成膜の場合、回転数は500〜
50 Q Or p mが好ましく、スヒ)’コートの
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。In addition, in the case of film formation by the spinner method, the rotation speed is 500~
50 Q Or p m is preferable, and after coating, a treatment such as heating or exposure to solvent vapor may be performed depending on the case.
ドクターブレード法、キャスト法、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、ブロモホルム、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
クロヘキサノン等の沸点120〜160℃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 cast method, a spinner method, or a dipping method, especially a spinner method, coating solvents such as bromoform, dibromoethane, ethyl cellosolve, xylene, chlorobenzene, cyclohexanone, etc. with a boiling point of 120 are used. ~160°C is preferably used.
また、記録層の安定性や耐光性向上のために、−・重積
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、アセチルアセトナートキレート、ビスフエニルジチ
オール、サリチルアルデヒドオキシム、ビスジチオ−α
−ジケトン等)又は3級アくン化合物を含有していても
よい。In addition, to improve the stability and light resistance of the recording layer, transition metal chelate compounds (e.g., acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-α) are used as stacked oxygen quenchers.
-diketone, etc.) or a tertiary amine compound.
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.
上記の様にして得られた光学記録媒体への記録は、基板
の両面又は片面に設けた記録層に1〜10μm程度に集
束した光、好ましくは、レーザー晃をあてることにより
行なう。レーザー光等が照射された部分は、光量子効果
により色変化が起こる。記録された情報の再生は、色変
化が起きている部分と起きていない部分の反射率或いは
吸光度の差を読み取ることにより行なうことができる。Recording on the optical recording medium obtained as described above is carried out by irradiating the recording layer provided on both sides or one side of the substrate with light focused to about 1 to 10 μm, preferably laser light. The area irradiated with laser light or the like undergoes a color change due to photon effects. Recorded information can be reproduced by reading the difference in reflectance or absorbance between areas where a color change has occurred and areas where no color change has occurred.
本発明の光学記録媒体について使用される光源としては
水銀ランプ、キセノンランプの他、レーザー光(N2
、He−Cd、アルゴンイオン、He−Ne、ルビー、
半導体、色素レーザー〉等が挙げられる。Light sources used for the optical recording medium of the present invention include mercury lamps, xenon lamps, and laser light (N2
, He-Cd, argon ion, He-Ne, ruby,
Semiconductors, dye lasers, etc.
[実施例]
以下、実施例を挙げて本発明をより具体的に説明するが
、本発明はその要旨を超えない限り、以下の実施例に限
定されるものではない。[Examples] Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples unless it exceeds the gist thereof.
実施例1 (1) 企−羞 以下の反応式に従って合成を行なった。Example 1 (1) Planning - shame Synthesis was carried out according to the following reaction formula.
■
■
し113
藺
■
20mAのDMSO(ジメチルスルホキサイド)を水冷
し、60重量%NaH1,6gをこの氷冷したDMSO
中に入れ30℃まで加熱し、水素の発泡がなくなるまで
1晩攪拌した。次に、2−メチルインドール2.62g
(o、02モル)を氷冷したこの温合液中に加え、3
0℃まで加熱し、2−メチルインドールを完全に溶かし
た。その後、水浴で冷やしながらヨウ化メチル11.6
gをゆっくり滴下し、約1時間攪拌を続けた。このもの
を160mj!の水に注ぎ、良く攪拌したところ、淡黄
色固体が生成した。これをベンゼンで抽出し、乾燥して
淡黄色固体の化合物量を得た。(収率:90%、b、p
、:76〜79℃72 m m Hg )
23
36mj!の25重量%ジメチルアミン水溶液と40m
1の氷酢酸との混合液を水浴で5℃まで冷やした。これ
に15mj!の46重量%ホルムアルデヒド水溶液を加
え、同様に5℃まで冷やした。■■ Shi113 藺■ 20 mA of DMSO (dimethyl sulfoxide) is water-cooled, and 1.6 g of 60 wt% NaH is added to this ice-cooled DMSO.
The mixture was heated to 30° C. and stirred overnight until hydrogen bubbles ceased. Next, 2.62 g of 2-methylindole
(o, 02 mol) was added to this ice-cooled warm mixture, and 3
It was heated to 0°C to completely dissolve the 2-methylindole. Then, while cooling in a water bath, methyl iodide 11.6
g was slowly added dropwise, and stirring was continued for about 1 hour. This thing is 160mj! When the mixture was poured into water and stirred well, a pale yellow solid was produced. This was extracted with benzene and dried to obtain the compound amount as a pale yellow solid. (Yield: 90%, b, p
,: 76-79℃ 72 mm Hg) 23 36mj! 25% by weight dimethylamine aqueous solution and 40m
A mixture of 1 and glacial acetic acid was cooled to 5°C in a water bath. 15mj for this! A 46% by weight formaldehyde aqueous solution was added thereto, and the mixture was similarly cooled to 5°C.
冷却後、化合物lを26.2g滴下した。滴下ごとに白
色固体が生成した。混合液は均一になるまでゆっくりと
攪拌した。室温にて一晩放置した。After cooling, 26.2 g of Compound 1 was added dropwise. A white solid formed with each drop. The mixture was slowly stirred until homogeneous. It was left at room temperature overnight.
その後、40g水酸化ナトリウム/ 400 m 41
の水の中に注ぎ、エーテルで抽出後、水洗して乾燥した
。溶媒を留去してから蒸留を行ない、化合物lを得た。Then 40g sodium hydroxide / 400 m 41
The mixture was poured into water, extracted with ether, washed with water, and dried. After removing the solvent, distillation was performed to obtain Compound 1.
(b、p、:105℃/ 2 m m Hg )i−■
、■09.1gの化合
物立を40m1の無水エタノールに溶解した。この混合
液を冷やしながら7,8gのヨウ化メチルを滴下した。(b, p,: 105°C/2 mm Hg) i-■
, 09.1 g of the compound was dissolved in 40 ml of absolute ethanol. While cooling the mixture, 7.8 g of methyl iodide was added dropwise.
室温で1時間放置し、結晶を生成させた。その後、0℃
で1晩放置することにより、反応は完結した。生成した
固体を集め、無水エタノールで2回洗い、その後無水エ
ーテルで3回洗い、白色固体の化合物4を得た。(収率
:90%)
i″′″■ 。■。The mixture was left at room temperature for 1 hour to form crystals. Then 0℃
The reaction was completed by standing overnight at . The generated solid was collected and washed twice with absolute ethanol and then three times with anhydrous ether to obtain Compound 4 as a white solid. (Yield: 90%) i″′″■. ■.
± ■10gNaC
N/100mj2水の中に17.2gの化合物Aを加え
、2時間加熱還流すると油層が分離した。この混合物を
冷却し、エーテルで抽出、水で洗浄、乾燥、溶媒留去し
た。生成物をカラム処理した後、得られた固体をエーテ
ル−n−ヘキサン混合液(エーテル二〇−ヘキサン=1
:1)で再結晶し、化合物■を得た。(収率:40〜7
0%)
6
ベンゾチオフェン33g (o、25モル)を乾燥テト
ラヒドロフラン(THF)150mJLに溶かした。こ
れを−30℃に冷却した後、n−ブチルリチウム(ヘキ
サン溶液)0.37mj2を滴下し、1時間攪拌した。± ■10gNaC
17.2 g of Compound A was added to N/100 mj2 water and heated under reflux for 2 hours to separate an oil layer. The mixture was cooled, extracted with ether, washed with water, dried and evaporated. After column treatment of the product, the obtained solid was treated with an ether-n-hexane mixture (ether 20-hexane=1
: Recrystallization with 1) yielded Compound (2). (Yield: 40-7
0%) 6 33 g (o, 25 mol) of benzothiophene were dissolved in 150 mJL of dry tetrahydrofuran (THF). After cooling this to -30°C, 0.37 mj2 of n-butyllithium (hexane solution) was added dropwise, and the mixture was stirred for 1 hour.
室温に約1時間放置した後、−10〜o℃に再び冷却し
、乾燥T)IF100mJ2にヨウ化メチル53g (
0,37モル)を溶かしkものを滴下した。−1ONo
℃で約1時間攪拌後、室温で一晩放置した。その後、水
を加えた後、生成物をエーテル抽出し、乾燥後エタノー
ル−水で再結晶し、化合物6(2−メチルベンゾチオフ
ェン)を得た。(収率:8o%)7
2gの2−メチルベンゾフェン6を260mj2の1.
2−ジクロロエタン中じ溶かし、これにクロロメチルエ
ーテル33gを加え、触媒として、塩化亜鉛50mgを
添加した。30分〜2時間反応させた後、水−クロロホ
ルムで抽出操作を行ない、有機層を留去し2.4gの化
合物工を得た。After leaving it at room temperature for about 1 hour, it was cooled again to -10~oC, and 53 g of methyl iodide (
0.37 mol) was dissolved and added dropwise. -1ON No.
After stirring at °C for about 1 hour, it was left at room temperature overnight. Thereafter, after adding water, the product was extracted with ether, dried, and recrystallized from ethanol-water to obtain Compound 6 (2-methylbenzothiophene). (Yield: 8o%) 7 2g of 2-methylbenzophene 6 was added to 260mj2 of 1.
The mixture was dissolved in 2-dichloroethane, 33 g of chloromethyl ether was added thereto, and 50 mg of zinc chloride was added as a catalyst. After reacting for 30 minutes to 2 hours, extraction was performed with water-chloroform, and the organic layer was distilled off to obtain 2.4 g of a compound.
(収率:90%)
工 ■
クロロメチル体7 1.42gを10mj!のベンゼン
に溶かし、これに30mgのテトラ−n−プチルアンモ
ニウムブロミドと2.5gのシアン化ナトリウムを溶か
した10mJ!の水溶液を加え、2〜3時間、60℃に
加熱しながら激しく攪拌した。(Yield: 90%) Engineering ■ Chloromethyl form 7 1.42g to 10mj! of benzene, and 30 mg of tetra-n-butylammonium bromide and 2.5 g of sodium cyanide were dissolved in this to 10 mJ! An aqueous solution of was added thereto, and the mixture was vigorously stirred while heating at 60° C. for 2 to 3 hours.
反応終了後、ベンゼンで抽出し、有機層を乾燥後、シリ
カゲルクロマトグラフィーで精製し、1.07gのシア
ノメチル体■を得た。(収率:74%)
■
−[III A ]
化合物01.012g (0,0055モル)と化合物
01.028g (o、0055モル)を四塩化炭素1
.58muとベンゼン1.58m1に溶かしてこれに、
テトラブチルアンモニウムブロマイド0.14gを加え
、40℃に熱した。更に、NaOH水t’gt&(50
重量%)2.18mILを30分で滴下した。生成物を
水に注ぎ、クロロホルムで抽出、乾燥、溶媒留去した後
、ベンゼンカラムクロマト処理後、液体クロマトグラフ
ィーにて分取して下記(2)の物性の[rn A ]の
化合物を得た。(収率:10%)
(2) 批立A
マススペクトル:367(M”)
開環体のλ□、:420nm
閉環体のλ、x:554nm
(3) 及主星旦
上記(1)で合成した化合物[IHA ]をベベンジに
10−4モル/℃になるように溶解して得た黄色溶液を
1cmX1cmX4cmのガラスセルに封入し、これに
435nmの単色光を5分間照射したところ、第1図に
示すように554nmに極大吸収を有する着色fit
(閉環体)[mA’]に変化した。After the reaction was completed, the mixture was extracted with benzene, and the organic layer was dried and purified by silica gel chromatography to obtain 1.07 g of cyanomethyl compound (2). (Yield: 74%) - [III A] Compound 01.012g (0,0055 mol) and compound 01.028g (o, 0055 mol) were mixed with carbon tetrachloride 1
.. Dissolve 58 mu and benzene in 1.58 ml and add to this.
0.14 g of tetrabutylammonium bromide was added and heated to 40°C. Furthermore, NaOH water t'gt&(50
% by weight) was added dropwise over 30 minutes. The product was poured into water, extracted with chloroform, dried, the solvent was distilled off, treated with benzene column chromatography, and fractionated using liquid chromatography to obtain the compound [rn A ] with the physical properties shown in (2) below. . (Yield: 10%) (2) Hitachi A Mass spectrum: 367 (M”) λ□ of the open ring form: 420 nm λ of the closed ring form, x: 554 nm (3) Synthesized using the above (1) A yellow solution obtained by dissolving the compound [IHA] in bebenzi at a concentration of 10-4 mol/°C was sealed in a 1 cm x 1 cm x 4 cm glass cell, and when the cell was irradiated with 435 nm monochromatic light for 5 minutes, the results were shown in Figure 1. Colored fit with maximum absorption at 554 nm as shown in
(Closed ring) [mA'].
C)13
[III A ]
で表わされる化合物2.0gの代りに、下記構造式
%式%
この着色状態は熱的に非常に安定であり、80℃で12
時間以上加熱しても第2図に示すように、全く着色状態
の吸収の減少は認められなかった。C) In place of 2.0 g of the compound represented by 13 [III A ], the following structural formula % Formula % This colored state is very thermally stable, with
As shown in FIG. 2, no decrease in the absorption of the colored state was observed even after heating for more than an hour.
次に、着色状態の前記ガラスセル水銀ランプとフィルタ
ーを組合せ578nmの単色光を5分間照射したところ
、ただちに消色し、元の黄色の状態に変化した。この変
化は100回以上繰り返し行なうことができた。Next, when the glass cell mercury lamp in the colored state was combined with a filter and monochromatic light of 578 nm was irradiated for 5 minutes, the color immediately disappeared and changed to the original yellow state. This change could be repeated over 100 times.
実施例2
(1) 生−羞
実施例1における下記構造式
で表わされる化合物1.8gを用い、他は実施例1と同
様にして、下記(2)の物性の化合物[II A ]を
得た。Example 2 (1) Using 1.8 g of the compound represented by the following structural formula in Example 1, a compound [II A ] having the physical properties shown in (2) below was obtained in the same manner as in Example 1. Ta.
[II A ]
(2) 物」L値
マススペクトル:345(M”)
開環体のλ□ウ :412nm
閉環体のλwax:549nm
(3) 及ヱ旦旦
実施例1と同様にして上記(1)で合成した化合物[1
1A]のベンゼン溶液を封入したガラスセルに435n
mの単色光を5分間光照射したところ、第3図に示すよ
うに549nmに極大吸収を有する着色体(閉環体)へ
変化した。この着色状態は熱的に非常に安定であり、8
0℃で12時間以上放置しても全く着色状態の変化は認
められなかった。[II A] (2) "L value mass spectrum of substance": 345 (M") λ□U of ring-opened form: 412 nm λwax of closed ring form: 549 nm (3) And the above ( The compound synthesized in 1) [1
1A] in a glass cell sealed with a benzene solution of 435n
When irradiated with monochromatic light of m for 5 minutes, it changed into a colored body (closed ring body) having maximum absorption at 549 nm, as shown in FIG. This colored state is very thermally stable and 8
Even after being left at 0° C. for 12 hours or more, no change in the coloring state was observed.
次に、水銀ランプとフィルターを組み合せ578、On
mの単色光を5分間照射したところ、ただちに消色し、
元の状態に変化した。この変化は100回以上繰り返し
行なうことができた。Next, combine the mercury lamp and filter 578, and turn it on.
When irradiated with m monochromatic light for 5 minutes, the color disappeared immediately.
changed to its original state. This change could be repeated over 100 times.
実施例3
(1) i−亙
水5mA及び水酸化カリウム2.4g (0,04モル
)を攪拌し、水酸化カリウムを溶解した。次いで、エチ
レングリコールモノエチルエーテル5mu及び下記構造
式[II A ]
で表わされるジシアノエチレン系化合物2g(0,00
6モル〉を加え、攪拌、還流下30時間反応させた。反
応終了後、室温まで冷却し、50mj!の水の中へ注い
だ。固形物を濾過し、濾液を希塩酸で中性から弱酸性に
した。析出した黄色固体をエーテル100mJiLで3
回抽出し、無水硫酸ナトリウムで乾燥した。エーテルを
留去し、得られたオイル状生成物をシリカゲルカラムク
ロマトグラフィー(ベンゼン:ヘキサン=1 : 1)
で精製し、エーテル−石油エーテルで結晶化した。Example 3 (1) 5 mA of i-water and 2.4 g (0.04 mol) of potassium hydroxide were stirred to dissolve the potassium hydroxide. Next, 5 mu of ethylene glycol monoethyl ether and 2 g of a dicyanoethylene compound represented by the following structural formula [II A ] (0,00
6 mol> was added thereto, and the mixture was reacted for 30 hours under stirring and reflux. After the reaction was completed, it was cooled to room temperature and heated to 50mj! poured into the water. The solids were filtered and the filtrate was made neutral to slightly acidic with dilute hydrochloric acid. The precipitated yellow solid was diluted with 100 mJiL of ether for 3
The extract was extracted twice and dried over anhydrous sodium sulfate. The ether was distilled off, and the resulting oily product was subjected to silica gel column chromatography (benzene:hexane=1:1).
and crystallized from ether-petroleum ether.
その結果、下記(2)の物性の化合物[II B ]の
黄黄色束を得た。(収率:20%)
[II B ]
(2) 1立E
マススペクトル:385(M”)
開環体のλ+max:452nm
実施例1と同様に上記(1)で合成した化合物19・[
11B]のベンゼン溶液を封入したガラスセルに、アル
ゴンイオンレーザ−からの488nmの光を2分間照射
したところ、第4図に示すように595nmに吸収極大
を有する着色体(閉環体)に変化した。この着色状態は
熱的に非常に安定であり、80℃において12時間以上
放置しても全く着色状態に変化は認められなかった。As a result, a yellow-yellow bundle of compound [II B ] having the physical properties shown in (2) below was obtained. (Yield: 20%) [II B ] (2) 1 E mass spectrum: 385 (M”) λ+max of ring-opened product: 452 nm Compound 19.[
When a glass cell containing a benzene solution of [11B] was irradiated with 488 nm light from an argon ion laser for 2 minutes, it changed to a colored body (closed ring body) with an absorption maximum at 595 nm, as shown in Figure 4. . This colored state was very stable thermally, and no change was observed in the colored state even after being left at 80° C. for 12 hours or more.
次に、He−Naレーザー光(633nm)を2分間照
射したところ、直ちに消色し、元の状態に変化した。こ
の変化は100回以上繰り返し行なうことができた。な
お、この吸収スベ多トル変化は670nmの半導体レー
ザーを用いても同様におこさせることができた。Next, when irradiated with He-Na laser light (633 nm) for 2 minutes, the color immediately disappeared and changed to the original state. This change could be repeated over 100 times. Note that this absorption smoothness change could be similarly caused using a 670 nm semiconductor laser.
実施例4
上記実施例3の(1)で合成した化合物200mgとポ
リスチレン(分子量16万)20gとをトルエン400
爪j2に:溶解し、その溶液をガラス基板上に塗布後、
乾燥して記録層を作製した。Example 4 200 mg of the compound synthesized in Example 3 (1) above and 20 g of polystyrene (molecular weight 160,000) were mixed in 400 g of toluene.
For nail j2: After dissolving and applying the solution on the glass substrate,
A recording layer was prepared by drying.
この記録層へ488nmのアルゴンイオンレーザ−光を
2分間照射し、全面を着色状態にした。This recording layer was irradiated with 488 nm argon ion laser light for 2 minutes to make the entire surface colored.
この着色状態は熱的に非常に安定であり、80℃におい
て通2時間以上放置しても退色は認められなかった。This colored state was very stable thermally, and no fading was observed even after being left at 80° C. for more than 2 hours.
次にHe−N6レーザー(10mW;633nm)によ
り書き込みを試みたところ、30秒間の照射で着色は直
ちに退色した。この着色、退色のサイクルは100回以
上繰り返して行なうことが可能であった。Next, when writing was attempted using a He-N6 laser (10 mW; 633 nm), the coloring immediately faded after irradiation for 30 seconds. This cycle of coloring and fading could be repeated over 100 times.
実施例5
実施例1に準じた方法により、下記第1表に示される化
合物を合成した。各々の化合物をベンゼン溶液中で紫外
線照射したところ、各々第1表に示す色調に発色した。Example 5 Compounds shown in Table 1 below were synthesized by a method similar to Example 1. When each compound was irradiated with ultraviolet rays in a benzene solution, each compound developed a color shown in Table 1.
封S
1
表
(その1)
第
表
(その3)
第
表
(その2)
(その5)
(その2)
実施例6
実施例3に準じた方法により、下記第2表に示される化
合物を合成した。各々の化合物をベンゼン溶液中で紫外
線照射したところ、各々第1表に示す色調に発色した。Sealing S 1 Table (Part 1) Table (Part 3) Table (Part 2) (Part 5) (Part 2) Example 6 Compounds shown in Table 2 below were synthesized by a method similar to Example 3. did. When each compound was irradiated with ultraviolet rays in a benzene solution, each compound developed a color shown in Table 1.
第 2 表 (その1)
第
表
(その3)
第
2
表
(その4)
なお、実施例5,6のいずれのものについても、着色状
態は熱的に非常に安定であり、着色−消色の変化は10
0回以上繰り返し行なうことができた。Table 2 (Part 1) Table (Part 3) Table 2 (Part 4) In both Examples 5 and 6, the colored state was very stable thermally, and the coloring - decoloring The change in is 10
I was able to repeat this more than 0 times.
[発明の効果コ
以上詳述した通り、本発明の光学記録媒体は熱的に安定
であり、サーモクロよズムを示さず、光照射により色変
化がおき、この状態は熱的に極めて安定である。そして
、別の波長の光を照射すると元の状態にもどり、この変
化は繰り返し行なうことができる。[Effects of the Invention] As detailed above, the optical recording medium of the present invention is thermally stable, does not exhibit thermochromism, changes color when irradiated with light, and this state is extremely stable thermally. . Then, when light of a different wavelength is irradiated, it returns to its original state, and this change can be repeated.
従って、本発明の光学記録媒体によれば、フォトンモー
ドで記録可能な高特性可逆的記録媒体が提供される。Therefore, according to the optical recording medium of the present invention, a high-quality reversible recording medium capable of recording in photon mode is provided.
第1図は、実施例1で作成した光学記録材料における化
合物[III A ]の吸収スペクトルの光変化を示す
図である。第2図は、実施例1の(3)で作成した光学
記録材料における本発明化合物の435nm光照射後の
着色状態の80℃における熱安定性を示す図である。第
3図は実施例2の(3)で作成した光学記録材料におけ
る本発明化合物[n A ]の吸収スペクトルの光変化
を示す図である。第4図は実施例3の(3)で作成した
光学記録材料における本発明化合物[II B ]の吸
収スペクトルの光変化を示す図である。FIG. 1 is a diagram showing optical changes in the absorption spectrum of compound [III A ] in the optical recording material prepared in Example 1. FIG. 2 is a diagram showing the thermal stability at 80° C. of the colored state of the compound of the present invention in the optical recording material prepared in Example 1 (3) after irradiation with 435 nm light. FIG. 3 is a diagram showing optical changes in the absorption spectrum of the compound of the present invention [n A ] in the optical recording material prepared in Example 2 (3). FIG. 4 is a diagram showing optical changes in the absorption spectrum of the compound [II B ] of the present invention in the optical recording material prepared in Example 3 (3).
Claims (5)
情報を記録する記録層を有する光学記録媒体において、
該記録層が1位及び2位に光照射によって環化しシクロ
ヘキサジエン環を形成してその光学的性質を変化せしめ
るような非対称の複素環を有する下記一般式[ I ] ▲数式、化学式、表等があります▼・・・[ I ] 〔式中、 A、Bは共に−CN基であるか又は互いに連結して−C
O−Z−CO−で表わされる基であり、ここにZは酸素
又は置換されていてもよい窒素原子を表わす。 R^1はアルキル基、ハロゲン原子又はトリフルオロメ
チル基を表わす。 R^2は置換されていてもよいアルキル基、置換されて
いてもよいアリール基又は置換されていてもよいシクロ
アルキル基を表わす。 環Yは置換されていてもよい炭素環又は複素環を表わす
。 Xは置換されていてもよいチオフェン環、ベンゾチオフ
ェン環、チアゾール環又はオキサゾール環を表わす。〕 で示されるエチレン誘導体を含有することを特徴とする
光学記録媒体。(1) In an optical recording medium having a recording layer that records optical information by changing its optical properties by light irradiation,
The following general formula [I] in which the recording layer has an asymmetric heterocycle at the 1st and 2nd positions that is cyclized by light irradiation to form a cyclohexadiene ring and change its optical properties: ▲Mathematical formula, chemical formula, table, etc. There is a
A group represented by O-Z-CO-, where Z represents oxygen or an optionally substituted nitrogen atom. R^1 represents an alkyl group, a halogen atom, or a trifluoromethyl group. R^2 represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted cycloalkyl group. Ring Y represents an optionally substituted carbocycle or heterocycle. X represents an optionally substituted thiophene ring, benzothiophene ring, thiazole ring or oxazole ring. ] An optical recording medium characterized by containing an ethylene derivative represented by the following.
O−Z−CO−で表わされる基であり、ここにZは酸素
又は置換されていてもよい窒素原子を表わす。 R^1、R^5はアルキル基、ハロゲン原子又はトリフ
ルオロメチル基を表わす。 R^2は置換されていてもよいアルキル基、置換されて
いてもよいアリール基又は置換されていてもよいシクロ
アルキル基を表わす。 R^3、R^4、R^6、R^7はそれぞれ水素原子、
ハロゲン原子、ヒドロキシ基、置換されていてもよいア
ルキル基、置換されていてもよいアルコキシ基、シアノ
基、ニトロ基、置換されていてもよいアルコキシカルボ
ニル基、トリフルオロメチル基、置換されていてもよい
アリール基、置換されていてもよいシクロアルキル基、
置換されていてもよいアリールオキシカルボニル基、置
換されていてもよいモノ又はジアルキルアミノカルボニ
ル基、置換されていてもよいアルキルカルボニルオキシ
基、置換されていてもよいアリールカルボニルオキシ基
、置換されていてもよいアリールオキシ基、置換されて
いてもよいアルコキシカルボニルオキシ基及び置換され
ていてもよいアリールオキシカルボニルオキシ基よりな
る群から選ばれる原子又は基を表わす。〕 で示されることを特徴とする特許請求の範囲第1項に記
載の光学記録媒体。(2) The ethylene derivative has the following general formula [II] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ... [II] [In the formula, A and B are both -CN groups or are connected to each other to form -C
A group represented by O-Z-CO-, where Z represents oxygen or an optionally substituted nitrogen atom. R^1 and R^5 represent an alkyl group, a halogen atom or a trifluoromethyl group. R^2 represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted cycloalkyl group. R^3, R^4, R^6, R^7 are each hydrogen atoms,
Halogen atom, hydroxy group, optionally substituted alkyl group, optionally substituted alkoxy group, cyano group, nitro group, optionally substituted alkoxycarbonyl group, trifluoromethyl group, optionally substituted Good aryl group, optionally substituted cycloalkyl group,
Optionally substituted aryloxycarbonyl group, optionally substituted mono- or dialkylaminocarbonyl group, optionally substituted alkylcarbonyloxy group, optionally substituted arylcarbonyloxy group, represents an atom or group selected from the group consisting of an optionally substituted aryloxy group, an optionally substituted alkoxycarbonyloxy group, and an optionally substituted aryloxycarbonyloxy group. ] The optical recording medium according to claim 1, characterized by:
O−Z−CO−で表わされる基であり、ここにZは酸素
又は置換されていてもよい窒素原子を表わす。 R^1、R^5はアルキル基、ハロゲン原子又はトリフ
ルオロメチル基を表わす。 R^2は置換されていてもよいアルキル基、置換されて
いてもよいアリール基又は置換されていてもよいシクロ
アルキル基を表わす。 R^3、R^4、R^6、R^7はそれぞれ水素原子、
ハロゲン原子、ヒドロキシ基、置換されていてもよいア
ルキル基、置換されていてもよいアルコキシ基、シアノ
基、ニトロ基、置換されていてもよいアルコキシカルボ
ニル基、トリフルオロメチル基、置換されていてもよい
アリール基、置換されていてもよいシクロアルキル基、
置換されていてもよいアリールオキシカルボニル基、置
換されていてもよいモノ又はジアルキルアミノカルボニ
ル基、置換されていてもよいアルキルカルボニルオキシ
基、置換されていてもよいアリールカルボニルオキシ基
、置換されていてもよいアリールオキシ基、置換されて
いてもよいアルコキシカルボニルオキシ基及び置換され
ていてもよいアリールオキシカルボニルオキシ基よりな
る群から選ばれる原子又は基を表わす。〕 で示されることを特徴とする特許請求の範囲第1項に記
載の光学記録媒体。(3) The ethylene derivative has the following general formula [III] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ... [III] [In the formula, A and B are both -CN groups or are connected to each other to form -C
A group represented by O-Z-CO-, where Z represents oxygen or an optionally substituted nitrogen atom. R^1 and R^5 represent an alkyl group, a halogen atom or a trifluoromethyl group. R^2 represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted cycloalkyl group. R^3, R^4, R^6, R^7 are each hydrogen atoms,
Halogen atom, hydroxy group, optionally substituted alkyl group, optionally substituted alkoxy group, cyano group, nitro group, optionally substituted alkoxycarbonyl group, trifluoromethyl group, optionally substituted Good aryl group, optionally substituted cycloalkyl group,
Optionally substituted aryloxycarbonyl group, optionally substituted mono- or dialkylaminocarbonyl group, optionally substituted alkylcarbonyloxy group, optionally substituted arylcarbonyloxy group, represents an atom or group selected from the group consisting of an optionally substituted aryloxy group, an optionally substituted alkoxycarbonyloxy group, and an optionally substituted aryloxycarbonyloxy group. ] The optical recording medium according to claim 1, characterized by:
O−Z−CO−で表わされる基であり、ここにZは酸素
又は置換されていてもよい窒素原子を表わす。 R^1、R^5はアルキル基、ハロゲン原子又はトリフ
ルオロメチル基を表わす。 R^2は置換されていてもよいアルキル基、置換されて
いてもよいアリール基又は置換されていてもよいシクロ
アルキル基を表わす。 R^3、R^4、R^6はそれぞれ水素原子、ハロゲン
原子、ヒドロキシ基、置換されていてもよいアルキル基
、置換されていてもよいアルコキシ基、シアノ基、ニト
ロ基、置換されていてもよいアルコキシカルボニル基、
トリフルオロメチル基、置換されていてもよいアリール
基、置換されていてもよいシクロアルキル基、置換され
ていてもよいアリールオキシカルボニル基、置換されて
いてもよいモノ又はジアルキルアミノカルボニル基、置
換されていてもよいアルキルカルボニルオキシ基、置換
されていてもよいアリールカルボニルオキシ基、置換さ
れていてもよいアリールオキシ基、置換されていてもよ
いアルコキシカルボニルオキシ基及び置換されていても
よいアリールオキシカルボニルオキシ基よりなる群から
選ばれる原子又は基を表わす。〕 で示されることを特徴とする特許請求の範囲第1項に記
載の光学記録媒体。(4) The ethylene derivative has the following general formula [IV] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ... [IV] [In the formula, A and B are both -CN groups or are connected to each other to form -C
A group represented by O-Z-CO-, where Z represents oxygen or an optionally substituted nitrogen atom. R^1 and R^5 represent an alkyl group, a halogen atom or a trifluoromethyl group. R^2 represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted cycloalkyl group. R^3, R^4, and R^6 are each a hydrogen atom, a halogen atom, a hydroxy group, an optionally substituted alkyl group, an optionally substituted alkoxy group, a cyano group, a nitro group, or a substituted good alkoxycarbonyl group,
Trifluoromethyl group, optionally substituted aryl group, optionally substituted cycloalkyl group, optionally substituted aryloxycarbonyl group, optionally substituted mono- or dialkylaminocarbonyl group, substituted an optionally substituted alkylcarbonyloxy group, an optionally substituted arylcarbonyloxy group, an optionally substituted aryloxy group, an optionally substituted alkoxycarbonyloxy group, and an optionally substituted aryloxycarbonyl group Represents an atom or group selected from the group consisting of oxy groups. ] The optical recording medium according to claim 1, characterized by:
O−Z−CO−で表わされる基であり、ここにZは酸素
又は置換されていてもよい窒素原子を表わす。 R^1、R^5はアルキル基、ハロゲン原子又はトリフ
ルオロメチル基を表わす。 R^2は置換されていてもよいアルキル基、置換されて
いてもよいアリール基又は置換されていてもよいシクロ
アルキル基を表わす。 R^3、R^4、R^6はそれぞれ水素原子、ハロゲン
原子、ヒドロキシ基、置換されていてもよいアルキル基
、置換されていてもよいアルコキシ基、シアノ基、ニト
ロ基、置換されていてもよいアルコキシカルボニル基、
トリフルオロメチル基、置換されていてもよいアリール
基、置換されていてもよいシクロアルキル基、置換され
ていてもよいアリールオキシカルボニル基、置換されて
いてもよいモノ又はジアルキルアミノカルボニル基、置
換されていてもよいアルキルカルボニルオキシ基、置換
されていてもよいアリールカルボニルオキシ基、置換さ
れていてもよいアリールオキシ基、置換されていてもよ
いアルコキシカルボニルオキシ基及び置換されていても
よいアリールオキシカルボニルオキシ基よりなる群から
選ばれる原子又は基を表わす。〕 で示されることを特徴とする特許請求の範囲第1項に記
載の光学記録媒体。(5) The ethylene derivative has the following general formula [V] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ... [V] [In the formula, A and B are both -CN groups or are connected to each other to form -C
A group represented by O-Z-CO-, where Z represents oxygen or an optionally substituted nitrogen atom. R^1 and R^5 represent an alkyl group, a halogen atom or a trifluoromethyl group. R^2 represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted cycloalkyl group. R^3, R^4, and R^6 are each a hydrogen atom, a halogen atom, a hydroxy group, an optionally substituted alkyl group, an optionally substituted alkoxy group, a cyano group, a nitro group, or a substituted good alkoxycarbonyl group,
Trifluoromethyl group, optionally substituted aryl group, optionally substituted cycloalkyl group, optionally substituted aryloxycarbonyl group, optionally substituted mono- or dialkylaminocarbonyl group, substituted an optionally substituted alkylcarbonyloxy group, an optionally substituted arylcarbonyloxy group, an optionally substituted aryloxy group, an optionally substituted alkoxycarbonyloxy group, and an optionally substituted aryloxycarbonyl group Represents an atom or group selected from the group consisting of oxy groups. ] The optical recording medium according to claim 1, characterized by:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1211879A JP2844704B2 (en) | 1989-08-17 | 1989-08-17 | Optical recording medium |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1211879A JP2844704B2 (en) | 1989-08-17 | 1989-08-17 | Optical recording medium |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH0375635A true JPH0375635A (en) | 1991-03-29 |
JP2844704B2 JP2844704B2 (en) | 1999-01-06 |
Family
ID=16613136
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1211879A Expired - Lifetime JP2844704B2 (en) | 1989-08-17 | 1989-08-17 | Optical recording medium |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2844704B2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5605779A (en) * | 1992-02-27 | 1997-02-25 | Sharp Kabushiki Kaisha | Optical memory medium |
WO2014090398A1 (en) * | 2012-12-10 | 2014-06-19 | Centogene Ag | Use of maleimide derivatives for preventing and treating leukemia |
-
1989
- 1989-08-17 JP JP1211879A patent/JP2844704B2/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5605779A (en) * | 1992-02-27 | 1997-02-25 | Sharp Kabushiki Kaisha | Optical memory medium |
WO2014090398A1 (en) * | 2012-12-10 | 2014-06-19 | Centogene Ag | Use of maleimide derivatives for preventing and treating leukemia |
US9724331B2 (en) | 2012-12-10 | 2017-08-08 | Centogene Ag | Use of maleimide derivatives for preventing and treating leukemia |
Also Published As
Publication number | Publication date |
---|---|
JP2844704B2 (en) | 1999-01-06 |
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