JP3604432B2 - Phthalocyanine compound and optical recording medium containing the same - Google Patents
Phthalocyanine compound and optical recording medium containing the same Download PDFInfo
- Publication number
- JP3604432B2 JP3604432B2 JP31165294A JP31165294A JP3604432B2 JP 3604432 B2 JP3604432 B2 JP 3604432B2 JP 31165294 A JP31165294 A JP 31165294A JP 31165294 A JP31165294 A JP 31165294A JP 3604432 B2 JP3604432 B2 JP 3604432B2
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- Prior art keywords
- group
- formula
- phthalocyanine compound
- optical recording
- medium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 Phthalocyanine compound Chemical class 0.000 title claims description 63
- 230000003287 optical effect Effects 0.000 title claims description 32
- 239000010410 layer Substances 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 239000011241 protective layer Substances 0.000 claims description 7
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052737 gold Inorganic materials 0.000 claims description 6
- 239000010931 gold Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 0 *C1(*)Oc(c(C#N)c(cc2)C#N)c2C=C1 Chemical compound *C1(*)Oc(c(C#N)c(cc2)C#N)c2C=C1 0.000 description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920006026 co-polymeric resin Polymers 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- 229940045803 cuprous chloride Drugs 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 239000001007 phthalocyanine dye Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- 229910052740 iodine Inorganic materials 0.000 description 3
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- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- LTFTWJYRQNTCHI-UHFFFAOYSA-N hex-1-yn-3-ol Chemical compound CCCC(O)C#C LTFTWJYRQNTCHI-UHFFFAOYSA-N 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- SKDFWEPBABSFMG-UHFFFAOYSA-N 1,2-dichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)CCl SKDFWEPBABSFMG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- VHCAZBIUJQZQCZ-UHFFFAOYSA-N 3,4,4-trimethylpent-1-en-3-ol Chemical compound CC(C)(C)C(C)(O)C=C VHCAZBIUJQZQCZ-UHFFFAOYSA-N 0.000 description 1
- DZNLEQBXXLGELU-UHFFFAOYSA-N 3,4-dimethylpent-1-yn-3-ol Chemical compound CC(C)C(C)(O)C#C DZNLEQBXXLGELU-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- FMLRBVOUYLRDRV-UHFFFAOYSA-N 3-ethyl-5-methylhept-1-yn-3-ol Chemical compound CCC(C)CC(O)(CC)C#C FMLRBVOUYLRDRV-UHFFFAOYSA-N 0.000 description 1
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- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- UZJZIZFCQFZDHP-UHFFFAOYSA-N 3-nitrobenzene-1,2-dicarbonitrile Chemical compound [O-][N+](=O)C1=CC=CC(C#N)=C1C#N UZJZIZFCQFZDHP-UHFFFAOYSA-N 0.000 description 1
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- CUUQUEAUUPYEKK-UHFFFAOYSA-N 4-ethyloct-1-yn-3-ol Chemical compound CCCCC(CC)C(O)C#C CUUQUEAUUPYEKK-UHFFFAOYSA-N 0.000 description 1
- NTNUBJHPRAMQPC-UHFFFAOYSA-N 5-methylhex-1-yn-3-ol Chemical compound CC(C)CC(O)C#C NTNUBJHPRAMQPC-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
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- 229930192627 Naphthoquinone Natural products 0.000 description 1
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- 229910008449 SnF 2 Inorganic materials 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/063—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having oxygen or sulfur atom(s) linked directly to the skeleton
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Description
【０００１】
【産業上の利用分野】
本発明は、新規な光ディスク用記録材料、情報記録、表示センサー、保護眼鏡等のオプトエレクトロニクス関連に重要な役割を果たす近赤外線吸収剤として有用な化合物と、それを記録層に含有して形成される光ディスク及び光カード等の光記録媒体に関する。
【０００２】
【従来の技術】
光ディスク、光カ−ド装置等における書き込み及び読み取りのためにレーザー光が利用されている。特にこれらの装置で用いられる光記録媒体の記録方式は、実用レベルとしては通常、光・熱変換を経たヒートモード記録（熱記録）が採用されており、そのために記録層としては低融点金属、有機高分子、さらには融解、蒸発、分解、あるいは昇華等の物理変化または化学変化を起こす有機色素が種々提案されている。なかでも融解、分解等の温度が低い有機色素系は記録感度上好ましいことから、シアニン系色素、フタロシアニン系色素、ナフタロシアニン系色素、アゾ系色素などを中心に記録層として開発されてきている。
【０００３】
例えば、特開平２−１４７２８６号公報において、記録層にシアニン系色素を含む光記録媒体が提案されている。しかしながら、この媒体系は長期保存性および耐光性に劣り、さらには記録特性も不十分であった。
【０００４】
アントラキノン色素（例えば、特開昭５８−２２４４４８号公報）、ナフトキノン色素（例えば、特開昭５８−２２４７９３号公報）を記録層に含む光記録媒体も提案されているが、いずれもシアニン系色素と同様に長期保存性および耐光性に劣り、さらには記録特性も不十分であった。
【０００５】
特開昭６１−２５８８６号公報、特開平２−４３２６９号公報（ＵＳＰ ４９６０５３８）、特開平２−２９６８８５号公報等においては、記録層にナフタロシアニン色素を含む光記録媒体が提案されている。この媒体系では、耐光性は優れるが、記録層の反射率が低く、記録特性も不十分であった。
【０００６】
また、光記録媒体の記録層に、フタロシアニン色素、特にアルコキシ置換フタロシアニンを利用する技術は、特開昭６１−１５４８８８号公報（ＥＰ １８６４０４）、同６１−１９７２８０号公報、同６１−２４６０９１号公報、同６２−３９２８６号公報（ＵＳＰ ４７６９３０７）、同６３−３７９９１号公報、同６３−３９３８８号公報、特表平２−５０２０９９号公報等により広く知られている。これらの特許に開示されているフタロシアニン色素を用いた光記録媒体においては、感度、記録特性において十分な性能を有しているとは言い難かった。それを改良したのが特開平３−６２８７８号公報（ＵＳＰ ５１２４０６７）であるが、その改良化合物においても、レーザー光による高速記録及び高密度記録時の誤差が大きく未だ実用上十分ではなかった。
【０００７】
特開平２−４３２６９号公報（ＵＳＰ ４９６０５３８）及び特開平２−２９６８８５号公報においてアルコキシ置換ナフタロシアニン、特開昭６３−３７９９１号公報において脂肪族炭化水素オキシ置換フタロシアニン、特開昭６３−３９３８８号公報においてはアルケニルチオ置換フタロシアニンの、光記録媒体への利用を提案しているが、感度、記録特性に効果があるということは記載されていない。
【０００８】
尚、その他の公知の色素を用いた光記録媒体の記録特性においても十分な性能を有しているものは見出されていない。
【０００９】
光記録媒体への書き込み及び読み出しは４００〜９００ｎｍのレーザー光を利用するので、記録材料の使用レーザー発振波長近傍における吸収係数、屈折率等の制御及び書き込み時における精度の良いピット形成が重要である。そのため、構造安定性が高く、レーザー発振波長近傍の光に対して屈折率が高く、分解特性が良好で、かつ感度の高い光記録媒体用色素の開発が必要となる。しかし、従来開発された光記録媒体用色素は、感度（Ｃ／Ｎ比、最適記録パワー）、記録特性（ジッター、デビエイション）について欠点を有するという問題があった。
【００１０】
【発明が解決しようとする課題】
本発明の目的は、上記欠点を改善し、感度が高く、記録特性並びに耐久性の良好な光記録媒体を提供しうる新規フタロシアニン色素を供給することである。
【００１１】
【課題を解決するための手段】
本発明者らは、前項の課題を解決すべく鋭意検討した結果、本発明を完成するに至った。即ち、本発明は、
▲１▼ 下記一般式（１）で表されるフタロシアニン化合物、
【００１２】
【化３】
【００１３】
【化４】
【００１４】
▲２▼ 一般式（１）において、Ｍで表される中心金属が、Ｐｄ，Ｃｕ，Ｒｕ，Ｐｔ，Ｎｉ，Ｃｏ，Ｒｈ，Ｚｎ，ＶＯ，ＴｉＯ，Ｓｉ（Ｙ）２，Ｓｎ（Ｙ）２，Ｇｅ（Ｙ）２（Ｙはハロゲン原子、アルコキシ基、アリールオキシ基、アシルオキシ基、ヒドロキシ基、アルキル基、アリール基、アルキルチオ基、アリールチオ基、トリアルキルシリルオキシ基、トリアルキルスズオキシ基、またはトリアルキルゲルマニウムオキシ基を表す。）であるフタロシアニン化合物。
【００１５】
▲３▼ 一般式（１）のフタロシアニン化合物を含有してなる光記録媒体。
▲４▼ 基板上に、一般式（１）のフタロシアニン化合物を含有する記録層、その上に金またはアルミニウムからなる反射層、さらにその上に保護層を積層した構成である光記録媒体に関するものである。
【００１６】
本発明のフタロシアニン化合物は、６５０〜９００ｎｍにシャープな吸収を有し、分子吸光係数も高く、長期安定性および耐久性にも優れるため、半導体レザー光を用いる光記録媒体（光ディスク、光カード等）の記録材料に適している。機構は未だ明らかでなく現在検討中であるが、特にフタロシアニン環に縮合したヘテロ環が記録時に感度の向上に寄与し、形成された信号の誤差の減少に効果を上げている。すなわち、光記録時に色素の溶融、分解を制御し、記録媒体の基板へのダメージの減少や、反射層を有する媒体の場合は反射層と記録層との密着性の改良である。
【００１７】
以下、本発明を詳細に説明する。
【００１８】
一般式（１）中、Ｒ１、Ｒ２及びＲ３で示される炭素数１〜１５のアルキル基の具体例としては、メチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｉｓｏ−ブチル基、ｓｅｃ−ブチル基、ｔ−ブチル基、ｎ−ペンチル基、ｉｓｏ−ペンチル基、ｎｅｏ−ペンチル基、２−メチルブチル基、ｎ−ヘキシル基、ｃｙｃｌｏ−ヘキシル基、２−エチルブチル基、２−メチルペンチル基、３−メチルペンチル基、４−メチルペンチル基、２，３−ジメチルブチル基、ｎ−ヘプチル基、２−メチルヘキシル基、３−メチルヘキシル基、４−メチルヘキシル基、５−メチルヘキシル基、２，４−ジメチルペンチル基、ｎ−オクチル基、２−エチルヘキシル基、２，５−ジメチルヘキシル基、２，５，５−トリメチルヘキシル基、２，４−ジメチルヘキシル基、２，２，４−トリメチルペンチル基、ｎ−ノニル基、ｎ−デシル基、４−エチルオクチル基、４−エチル−４，５−メチルヘキシル基、ｎ−ウンデシル基、ｎ−ドデシル基、１，３，５，７−テトラメチルオクチル基、４−ブチルオクチル基、６，６−ジエチルオクチル基、ｎ−トリデシル基、６−メチル−４−ブチルオクチル基、ｎ−テトラデシル基、ｎ−ペンタデシル基、３，５−ジメチルヘプチル基、２，６−ジメチルヘプチル基、２，４−ジメチルヘプチル基、２，２，５，５−テトラメチルヘキシル基、１−ｃｙｃｌｏ−ペンチル−２，２−ジメチルプロピル基、１−ｃｙｃｌｏ−ヘキシル−２，２−ジメチルプロピル基等が挙げられる。
【００１９】
また、式（１）中、Ｍで示される２価金属の例としては、Ｃｕ，Ｚｎ，Ｆｅ，Ｃｏ，Ｎｉ，Ｒｕ，Ｒｈ，Ｐｄ，Ｐｔ，Ｍｎ，Ｓｎ，Ｍｇ，Ｐｂ，Ｈｇ，Ｃｄ，Ｂａ，Ｔｉ，Ｂｅ，Ｃａ等が挙げられ、１置換の３価金属の例としては、Ａｌ−Ｆ，Ａｌ−Ｃｌ，Ａｌ−Ｂｒ，Ａｌ−Ｉ，Ｇａ−Ｆ，Ｇａ−Ｃｌ，Ｇａ−Ｂｒ，Ｇａ−Ｉ，Ｉｎ−Ｆ，Ｉｎ−Ｃｌ，Ｉｎ−Ｂｒ，Ｉｎ−Ｉ，Ｔｌ−Ｆ，Ｔｌ−Ｃｌ，Ｔｌ−Ｂｒ，Ｔｌ−Ｉ，Ａｌ−Ｃ６Ｈ５，Ａｌ−Ｃ６Ｈ４（ＣＨ３），Ｉｎ−Ｃ６Ｈ５，Ｉｎ−Ｃ６Ｈ４（ＣＨ３），Ｍｎ（ＯＨ），Ｍｎ（ＯＣ６Ｈ５），Ｍｎ〔ＯＳｉ（ＣＨ３）３〕，Ｆｅ−Ｃｌ，Ｒｕ−Ｃｌ等が挙げられ、２置換の４価金属の例としては、ＣｒＣｌ２，ＳｉＦ２，ＳｉＣｌ２，ＳｉＢｒ２，ＳｉＩ２，ＳｎＦ２，ＳｎＣｌ２，ＳｎＢｒ２，ＺｒＣｌ２，ＧｅＦ２，ＧｅＣｌ２，ＧｅＢｒ２，ＧｅＩ２，ＴｉＦ２，ＴｉＣｌ２，ＴｉＢｒ２，Ｓｉ（ＯＨ）２，Ｓｎ（ＯＨ）２，Ｇｅ（ＯＨ）２，Ｚｒ（ＯＨ）２，Ｍｎ（ＯＨ）２，ＴｉＡ２，ＣｒＡ２，ＳｉＡ２，ＳｎＡ２，ＧｅＡ２〔Ａはアルキル基、フェニル基、ナフチル基およびその誘導体を表す〕，Ｓｉ（ＯＡ’）２，Ｓｎ（ＯＡ’）２，Ｇｅ（ＯＡ’）２，Ｔｉ（ＯＡ’）２，Ｃｒ（ＯＡ’）２〔Ａ’はアルキル基、フェニル基、ナフチル基、トリアルキルシリル基、ジアルキルアルコキシシリル基およびその誘導体を表す〕，Ｓｉ（ＳＡ”）２，Ｓｎ（ＳＡ”）２，Ｇｅ（ＳＡ”）２〔Ａ”はアルキル基、フェニル基、ナフチル基およびその誘導体を表す〕等が挙げられ、オキシ金属の例としては、ＶＯ，ＭｎＯ，ＴｉＯ等が挙げられる。好ましくは、Ｐｄ、Ｃｕ，Ｒｕ，Ｐｔ，Ｎｉ，Ｃｏ，Ｒｈ，Ｚｎ，ＶＯ，ＴｉＯ，Ｓｉ（Ｙ）２，Ｓｎ（Ｙ）２，Ｇｅ（Ｙ）２（Ｙはハロゲン原子、アルコキシ基、アリールオキシ基、アシルオキシ基、ヒドロキシ基、アリキル基、アリール基、アルキルチオ基、アリールチオ基、トリアルキルシリルオキシ基、トリアルキルスズオキシ基またはトリアルキルゲルマニウムオキシ基を表す。）であり、特に好ましい例としては、Ｃｕ，Ｎｉ，Ｃｏ，Ｍｇ，Ｚｎ，Ｐｄ，Ｐｔ，ＶＯ等である。
【００２０】
一般式（１）で示されるフタロシアニン化合物の合成法としては、下式（２）または（３）、
【００２１】
【化５】
【００２２】
【化６】
また、一般式（２）または（３）で示される化合物は、以下に示した経路で製造することができる。
【００２３】
【化７】
市販されている３−ニトロフタロニトリル（Ａ）を、塩基の存在下、Ｒ４ＯＨ〔Ｒ４はアルキイル基を表す。〕で示されるアルコール誘導体と反応させてアルコキシフタロニトリル（Ｂ）を得る。更に（Ｂ）をジアルキルアニリン類やＤＭＩ等の高沸点溶剤中で反応することで目的とする一般式（２）または（３）で示される化合物の単品か或いはその混合物が製造され、混合物の場合は、カラムクロマト等の方法により分離し、目的とする一般式（２）または（３）で示される化合物の単品を得ることができる。
【００２５】
Ｒ４ＯＨで示されるアルコール誘導体の例としては、１−ブチン−３−オール、３−メチル−１−ブチン−３−オール、１−ペンチン−３−オール、１−ヘキシン−３−オール、３−メチル−１−ペンチン−３−オール、３，４−ジメチル−１−ペンチン−３−オール、１−ヘプチン−３−オール、３−エチル−１−ペンチン−３−オール、５−メチル−１−ヘキシン−３−オール、３−メチル−１−ヘキシン−３−オール、３−メチル−４−ヘキシン−３−オール、３，５−ジメチル−１−ヘキシン−３−オール、３，４，４−トリメチル−１−ペンテン−３−オール、４−エチル−１−ヘキシン−３−オール、１−エチニル−１−シクロヘキサノール、１−オクチン−３−オール、３，６−ジメチル−１−ヘプチン−３−オール、３−エチル−１−ヘプチン−３−オール、３−エチル−５−メチル−１−ヘプチン−３−オール、４−エチル−１−オクチン−３−オール、等が挙げられる。
【００２６】
本発明のフタロシアニン化合物を用いて光記録媒体を製造する方法には、透明基板上に本発明のフタロシアニン化合物を含む１〜３種の化合物を１層または２層に塗布、あるいは蒸着する方法があり、塗布法としては、バインダー樹脂２０重量％以下、好ましくは０％と、本発明のフタロシアニン化合物０．０５〜２０重量％、好ましくは０．５〜２０重量％となるように溶媒に溶解し、スピンコーターで塗布する方法等がある。また蒸着方法としては１０−５〜１０−７ｔｏｒｒ、１００〜３００℃にて基板上にフタロシアニン化合物を堆積させる方法等がある。
【００２７】
基板としては、光学的に透明な樹脂であればよい。例えば、アクリル樹脂、ポリエチレン樹脂、塩化ビニル樹脂、塩化ビニリデン樹脂、ポリカーボネート樹脂、ポリオレフィン共重合樹脂、塩化ビニル共重合樹脂、塩化ビニリデン共重合樹脂、スチレン共重合樹脂等が挙げられる。また基板は熱硬化性樹脂または紫外線硬化性樹脂により表面処理がなされていてもよい。
【００２８】
光記録媒体（光ディスク、光カード等）を作製する場合、コストの面、ユーザーの取り扱いの面より、基板はポリアクリレート基板またはポリカーボネート基板を用い、かつスピンコート法により塗布されるのが好ましい。
【００２９】
基板の耐溶剤性より、スピンコートに用いる溶剤は、ハロゲン化炭化水素（例えば、ジクロロメタン、クロロホルム、四塩化炭素、テトラクロロエチレン、ジクロロジフルオロエタン等）、エーテル類（例えば、テトラヒドロフラン、ジエチルエーテル、ジプロピルエーテル、ジブチルエーテル、ジオキサン等）、アルコール類（例えば、メタノール、エタノール、プロパノール等）、セロソルブ類（例えば、メチルセロソルブ、エチルセロソルブ等）、炭化水素類（例えば、ヘキサン、シクロヘキサン、エチルシクロヘキサン、シクロオクタン、ジメチルシクロヘキサン、オクタン、ベンゼン、トルエン、キシレン等）、あるいはこれらの混合溶媒が好適に用いられる。
【００３０】
記録媒体として加工するには、上記の様に基板で覆う、あるいは２枚の記録層を設けた基板に、エアーギャップを設けて対向させて張り合わせる、または、記録層上に反射層（アルミニウムまたは金）を設け、熱硬化性または光硬化性樹脂の保護層を積層する方法などがある。保護層として、Ａｌ２Ｏ３，ＳｉＯ２，ＳｉＯ，ＳｎＯ２等の無機化合物を利用してもよい。
【００３１】
【実施例】
以下、実施例により本発明を具体的に説明するが、本発明の実施の態様はこれにより限定されるものではない。
【００３２】
実施例１
下記構造式（３−１）
【００３３】
【化８】
可視吸光スペクトル及び元素分析の結果は以下の通りであった。
【００３４】
【化９】
上記フタロシアニン化合物のｎ−オクタン溶液（１０ｇ／ｌ）をスパイラルグルーブ（ピッチ１．６μｍ、溝幅０．６μｍ、溝深０．１８μｍ）付きの外形１２０ｍｍ、厚さ１．２ｍｍのＣＤ−Ｒ用ポリカーボネート基板上に５００〜１０００ｒｐｍでスピンコート成膜した。その上に３０ｎｍの金をスパッタ蒸着して反射層を形成し、続いて光硬化型ポリアクリル樹脂によりオーバーコート後光硬化させ保護層を形成してＣＤ−Ｒ媒体を作製した。この媒体の反射率は７１％（７７５〜７９０ｎｍ）であり、７８０ｎｍの半導体レーザーを用いて線速１．３ｍ／ｓｅｃでＥＦＭ信号を５．５ｍＷのパワーで書き込むことができ、その時のエラーレートは１０未満であった。
【００３７】
実施例２
前記構造式（３−１）で示されるフタロニトリル誘導体２２．４ｇ（０．１モル）、ＤＢＵ１５．２ｇ（０．１モル）及びｎ−アミルアルコール１２５ｇよりなる混合物を窒素雰囲気下で、１００℃まで昇温させた。次に、同温度で塩化パラジウム５．３ｇ（０．０３モル）を添加し、９５〜１００℃で３０時間反応させた。反応終了後、冷却し、不溶物を濾別した。濾液を減圧濃縮して溶媒を回収した後、カラム精製（シリカゲル５００ｇ、溶媒トルエン）し、下記構造式（１−２）で示されるフタロシアニン化合物１２．０ｇ（収率４８％）を得た。
可視吸光スペクトル及び元素分析の結果は以下の通りであった。
【００３８】
【化１０】
上記フタロシアニン化合物のｎ−オクタン溶液（１０ｇ／ｌ）をスパイラルグルーブ（ピッチ１．６μｍ、溝幅０．６μｍ、溝深０．１８μｍ）付きの外形１２０ｍｍ、厚さ１．２ｍｍのＣＤ−Ｒ用ポリカーボネート基板上に５００〜１０００ｒｐｍでスピンコート成膜した。その上に３０ｎｍの金をスパッタ蒸着して反射層を形成し、続いて光硬化型ポリアクリル樹脂によりオーバーコート後光硬化させ保護層を形成してＣＤ−Ｒ媒体を作製した。７８０ｎｍの半導体レーザーで記録したとき、７ｍＷのパワーで６０ｄＢのＣＮ比を得た。０．５ｍＷの再生光で１０５回再生しても変化は見られなかった。また、８０℃／８０％ＲＨの条件で１０００時間経過後も記録に変化はなかった。
【００４１】
実施例３
下記構造式（２−１）
【００４２】
【化１１】
可視吸光スペクトル及び元素分析の結果は以下の通りであった。
【００４３】
【化１２】
上記フタロシアニン化合物のｎ−オクタン溶液（１０ｇ／ｌ）をスパイラルグルーブ（ピッチ１．６μｍ、溝幅０．６μｍ、溝深０．１８μｍ）付きの外形１２０ｍｍ、厚さ１．２ｍｍのＣＤ−Ｒ用ポリカーボネート基板上に５００〜１０００ｒｐｍでスピンコート成膜した。その上に３０ｎｍの金をスパッタ蒸着して反射層を形成し、続いて光硬化型ポリアクリル樹脂によりオーバーコート後光硬化させ保護層を形成してＣＤ−Ｒ媒体を作製した。この媒体の反射率は７３％（７７５〜７９０ｎｍ）であり、７８０ｎｍの半導体レーザーを用いて線速１．３ｍ／ｓｅｃでＥＦＭ信号を６．０ｍＷのパワーで書き込むことができ、その時のエラーレートは１０未満であった。
【００４６】
実施例４
前記構造式（２−１）で示されるフタロニトリル誘導体２２．４ｇ（０．１モル）、ＤＢＵ１５．２ｇ（０．１モル）及びｎ−アミルアルコール１２５ｇよりなる混合物を窒素雰囲気下で、１００℃まで昇温させた。次に、同温度で塩化パラジウム５．３ｇ（０．０３モル）を添加し、９５〜１００℃で３５時間反応させた。反応終了後、冷却し、不溶物を濾別した。濾液を減圧濃縮して溶媒を回収した後、カラム精製（シリカゲル５００ｇ、溶媒トルエン）し、下記構造式（１−４）で示されるフタロシアニン化合物１４．６ｇ（収率６１％）を得た。
可視吸光スペクトル及び元素分析の結果は以下の通りであった。
【００４７】
【化１３】
上記フタロシアニン化合物を用いて実施例１と同様にしてＣＤ−Ｒ型媒体を作製した。この媒体に、波長７８０ｎｍのレーザーを用いて、線速１．３ｍ／ｓでＥＦＭ信号を６．０ｍＷのパワーで書き込んだときのエラーレートは、１０未満であった。
【００５０】
実施例５
下記構造式（３−２）
【００５１】
【化１４】
可視吸光スペクトル及び元素分析の結果は以下の通りであった。
【００５２】
【化１５】
上記フタロシアニン化合物を用いて実施例１と同様にしてＣＤ−Ｒ型媒体を作製した。この媒体に、波長７８０ｎｍのレーザーを用いて、線速１．３ｍ／ｓでＥＦＭ信号を６．０ｍＷのパワーで書き込んだときのエラーレートは、１０未満であった。
【００５５】
実施例６
下記構造式（２−２）
【００５６】
【化１６】
可視吸光スペクトル及び元素分析の結果は以下の通りであった。
【００５７】
【化１７】
上記フタロシアニン化合物を用いて実施例１と同様にしてＣＤ−Ｒ型媒体を作製した。この媒体に、波長７８０ｎｍのレーザーを用いて、線速１．３ｍ／ｓでＥＦＭ信号を６．０ｍＷのパワーで書き込んだときのエラーレートは、１０未満であった。
【００６０】
実施例７
前記構造式（２−２）で示されるフタロニトリル誘導体２６．６ｇ（０．１モル）、ＤＢＵ１５．２ｇ（０．１モル）及びｎ−アミルアルコール１２５ｇよりなる混合物を窒素雰囲気下で、１００℃まで昇温させた。次に、同温度で塩化パラジウム５．３ｇ（０．０３モル）を添加し、９５〜１００℃で３３時間反応させた。反応終了後、冷却し、不溶物を濾別した。濾液を減圧濃縮して溶媒を回収した後、カラム精製（シリカゲル５００ｇ、溶媒トルエン）し、下記構造式（１−７）で示されるフタロシアニン化合物１４．１ｇ（収率４８％）を得た。
可視吸光スペクトル及び元素分析の結果は以下の通りであった。
【００６１】
【化１８】
上記フタロシアニン化合物を用いて実施例１と同様にしてＣＤ−Ｒ型媒体を作製した。この媒体に、波長７８０ｎｍのレーザーを用いて、線速１．３ｍ／ｓでＥＦＭ信号を６．０ｍＷのパワーで書き込んだときのエラーレートは、１０未満であった。
【００６４】
実施例８
下記構造式（２−３）
【００６５】
【化１９】
可視吸光スペクトル及び元素分析の結果は以下の通りであった。
【００６６】
【化２０】
上記フタロシアニン化合物を用いて実施例１と同様にしてＣＤ−Ｒ型媒体を作製した。この媒体に、波長７８０ｎｍのレーザーを用いて、線速１．３ｍ／ｓでＥＦＭ信号を６．０ｍＷのパワーで書き込んだときのエラーレートは、１０未満であった。
【００６９】
比較例１
下記構造式（Ｃ）で示される特開平３−６２８７８号公報（ＵＳＰ５１２４０６７）の例示化合物を用いて実施例１と同様にして作製した媒体を評価した。
【００７０】
【化２１】
この媒体に７８０ｎｍの半導体レーザーを用いて、線速１．３ｍ／ｓでＥＦＭ信号を書き込むために１０ｍＷのパワーが必要であった。また、その時のエラーレートは１２であった。
【００７２】
実施例９〜２０
実施例１と同様にして下記第１表に示すフタロシアニン化合物を合成し、実施例１と同様にしてＣＤ−Ｒ媒体を作製し、７８０ｎｍの半導体レーザーを用いて、線速１．３ｍ／ｓでＥＦＭ信号を書き込むために必要なレーザーパワー（ｍｗ）を測定し、またその時のエラーレートを評価した。エラーレートの評価としては、○はエラーレートが１０未満、×はエラーレートが１０以上であることを示す。結果を第１表に示す。
【００７３】
【表１】
【発明の効果】
本発明のフタロシアニン化合物は、ヘテロ環がフタロシアニン環に縮合した新規なフタロシアニン化合物であり、また、このヘテロ環がフタロシアニン環と共役するために、吸収波長領域の制御がし易くなると共に、記録時に色素の分解・溶融が制御され精度の高いピット形成が行われたこと、分解発熱量の減少により記録媒体の樹脂基板へのダメージが減少したこと、反射層を有する記録媒体の場合は記録層と反射層である金属層との密着性が向上に寄与し、この化合物を用いた光記録媒体においては、光記録時の信号が正しく書き込めるようになり、感度、記録特性の向上に効果を上げた。[0001]
[Industrial applications]
The present invention relates to a novel recording material for optical disks, information recording, a display sensor, a compound useful as a near-infrared absorber that plays an important role in optoelectronics such as safety glasses, and a recording layer containing the compound. And optical recording media such as optical cards.
[0002]
[Prior art]
2. Description of the Related Art Laser light is used for writing and reading in optical disks, optical card devices, and the like. In particular, as a recording method of an optical recording medium used in these apparatuses, as a practical level, heat mode recording (thermal recording) through light-to-heat conversion is usually adopted. Various organic polymers and organic dyes that cause physical or chemical changes such as melting, evaporation, decomposition, or sublimation have been proposed. Among them, organic dyes having low melting and decomposition temperatures are preferable from the viewpoint of recording sensitivity. Therefore, cyanine dyes, phthalocyanine dyes, naphthalocyanine dyes, and azo dyes have been developed as recording layers.
[0003]
For example, JP-A-2-147286 proposes an optical recording medium containing a cyanine dye in a recording layer. However, this medium system was inferior in long-term storage properties and light fastness, and was also insufficient in recording characteristics.
[0004]
Optical recording media containing an anthraquinone dye (for example, JP-A-58-224448) and a naphthoquinone dye (for example, JP-A-58-224793) in the recording layer have been proposed. Similarly, it was inferior in long-term storage property and light fastness, and was also insufficient in recording characteristics.
[0005]
JP-A-61-25886, JP-A-2-43269 (USP 4,960,538), JP-A-2-296885, and the like propose optical recording media containing a naphthalocyanine dye in a recording layer. In this medium system, the light resistance was excellent, but the reflectance of the recording layer was low, and the recording characteristics were insufficient.
[0006]
Further, techniques for using a phthalocyanine dye, particularly an alkoxy-substituted phthalocyanine, in the recording layer of an optical recording medium are disclosed in JP-A-61-154888 (EP 186404), JP-A-61-197280, and JP-A-61-246091. It is widely known from JP-A-62-39286 (US Pat. No. 4,769,307), JP-A-63-37991, JP-A-63-39388, and JP-A-2-502099. The optical recording media using phthalocyanine dyes disclosed in these patents have not been said to have sufficient performance in sensitivity and recording characteristics. Japanese Patent Laid-Open Publication No. Hei 3-62878 (US Pat. No. 5,240,067) has improved this. However, even with the improved compound, errors at the time of high-speed recording and high-density recording with a laser beam are large and are not yet practically sufficient.
[0007]
JP-A-2-43269 (USP 4,960,538) and JP-A-2-296885, alkoxy-substituted naphthalocyanines, JP-A-63-37991, aliphatic hydrocarbon oxy-substituted phthalocyanines, JP-A-63-39388. Discloses the use of an alkenylthio-substituted phthalocyanine for an optical recording medium, but does not disclose that it has an effect on sensitivity and recording characteristics.
[0008]
It should be noted that none of the recording characteristics of optical recording media using other known dyes have been found to have sufficient performance.
[0009]
Since writing and reading to and from the optical recording medium uses a laser beam of 400 to 900 nm, it is important to control the absorption coefficient and refractive index of the recording material in the vicinity of the used laser oscillation wavelength and to form pits with high accuracy during writing. . Therefore, it is necessary to develop a dye for an optical recording medium having high structural stability, a high refractive index for light near the laser oscillation wavelength, good decomposition characteristics, and high sensitivity. However, conventionally developed dyes for optical recording media have the problem that they have drawbacks in sensitivity (C / N ratio, optimum recording power) and recording characteristics (jitter, deviation).
[0010]
[Problems to be solved by the invention]
SUMMARY OF THE INVENTION An object of the present invention is to provide a novel phthalocyanine dye capable of improving the above-mentioned drawbacks and providing an optical recording medium having high sensitivity, good recording characteristics and good durability.
[0011]
[Means for Solving the Problems]
The present inventors have conducted intensive studies in order to solve the above-mentioned problem, and as a result, completed the present invention. That is, the present invention
(1) a phthalocyanine compound represented by the following general formula (1),
[0012]
Embedded image
[0013]
Embedded image
[0014]
{Circle around (2)} In the general formula (1), the central metal represented by M is Pd, Cu, Ru, Pt, Ni, Co, Rh, Zn, VO, TiO, Si (Y) 2 , Sn (Y) 2 , Ge (Y) 2 (Y is a halogen atom, an alkoxy group, an aryloxy group, an acyloxy group, a hydroxy group, an alkyl group, an aryl group, an alkylthio group, an arylthio group, a trialkylsilyloxy group, a trialkyltinoxy group, or A phthalocyanine compound which is a trialkylgermanium oxy group).
[0015]
(3) An optical recording medium containing the phthalocyanine compound of the general formula (1).
(4) The present invention relates to an optical recording medium having a structure in which a recording layer containing a phthalocyanine compound represented by the general formula (1) is formed on a substrate, a reflective layer made of gold or aluminum is further formed thereon, and a protective layer is further formed thereon. is there.
[0016]
The phthalocyanine compound of the present invention has sharp absorption at 650 to 900 nm, has a high molecular extinction coefficient, and is excellent in long-term stability and durability. Therefore, an optical recording medium using semiconductor laser light (optical disk, optical card, etc.) Suitable for recording materials. The mechanism is not yet clear and is currently under study. In particular, a heterocyclic ring condensed with a phthalocyanine ring contributes to improvement in sensitivity during recording, and is effective in reducing errors in the formed signal. That is, melting and decomposition of the dye during optical recording are controlled to reduce damage to the substrate of the recording medium, and in the case of a medium having a reflective layer, to improve the adhesion between the reflective layer and the recording layer.
[0017]
Hereinafter, the present invention will be described in detail.
[0018]
In the general formula (1), specific examples of the alkyl group having 1 to 15 carbon atoms represented by R 1 , R 2 and R 3 include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group and an n- Butyl group, iso-butyl group, sec-butyl group, t-butyl group, n-pentyl group, iso-pentyl group, neo-pentyl group, 2-methylbutyl group, n-hexyl group, cyclo-hexyl group, 2- Ethylbutyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 2,3-dimethylbutyl group, n-heptyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl Group, 5-methylhexyl group, 2,4-dimethylpentyl group, n-octyl group, 2-ethylhexyl group, 2,5-dimethylhexyl group, 2,5,5-trimethylhexyl Group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, n-nonyl group, n-decyl group, 4-ethyloctyl group, 4-ethyl-4,5-methylhexyl group, n- Undecyl group, n-dodecyl group, 1,3,5,7-tetramethyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, n-tridecyl group, 6-methyl-4-butyloctyl group, n-tetradecyl group, n-pentadecyl group, 3,5-dimethylheptyl group, 2,6-dimethylheptyl group, 2,4-dimethylheptyl group, 2,2,5,5-tetramethylhexyl group, 1-cyclo -Pentyl-2,2-dimethylpropyl group, 1-cyclo-hexyl-2,2-dimethylpropyl group and the like.
[0019]
In the formula (1), examples of the divalent metal represented by M include Cu, Zn, Fe, Co, Ni, Ru, Rh, Pd, Pt, Mn, Sn, Mg, Pb, Hg, Cd, Ba, Ti, Be, Ca, etc. are mentioned, and examples of monosubstituted trivalent metals are Al-F, Al-Cl, Al-Br, Al-I, Ga-F, Ga-Cl, Ga-Br. , Ga-I, In-F , In-Cl, In-Br, In-I, Tl-F, Tl-Cl, Tl-Br, Tl-I, Al-C 6 H 5, Al-C 6 H 4 (CH 3), In-C 6 H 5, In-C 6 H 4 (CH 3), Mn (OH), Mn (OC 6 H 5), Mn [OSi (CH 3) 3], Fe-Cl, ru-Cl, and examples of the tetravalent metal 2-substituted, CrCl 2, SiF 2, SiCl 2, SiBr 2, iI 2, SnF 2, SnCl 2 , SnBr 2, ZrCl 2, GeF 2, GeCl 2, GeBr 2, GeI 2, TiF 2, TiCl 2, TiBr 2, Si (OH) 2, Sn (OH) 2, Ge ( OH) 2, Zr (OH) 2, Mn (OH) 2, TiA 2, CrA 2, SiA 2, SnA 2, GeA 2 [a represents an alkyl group, a phenyl group, a naphthyl group and a derivative thereof], Si ( OA ′) 2 , Sn (OA ′) 2 , Ge (OA ′) 2 , Ti (OA ′) 2 , Cr (OA ′) 2 [A ′ is an alkyl group, a phenyl group, a naphthyl group, a trialkylsilyl group, dialkylalkoxycarbonyl represents a silyl group and derivatives thereof], Si (SA ") 2, Sn (SA") 2, Ge (SA ") 2 [a" represents an alkyl group, a phenyl group, a naphthyl group Oyo As representative of the derivative], and examples of oxy metal, VO, MnO, TiO, and the like. Preferably, Pd, Cu, Ru, Pt, Ni, Co, Rh, Zn, VO, TiO, Si (Y) 2 , Sn (Y) 2 , Ge (Y) 2 (Y is a halogen atom, an alkoxy group, an aryl An oxy group, an acyloxy group, a hydroxy group, an aryl group, an aryl group, an alkylthio group, an arylthio group, a trialkylsilyloxy group, a trialkyltinoxy group or a trialkylgermaniumoxy group). , Cu, Ni, Co, Mg, Zn, Pd, Pt, VO and the like.
[0020]
As a method for synthesizing the phthalocyanine compound represented by the general formula (1), the following formula (2) or (3):
[0021]
Embedded image
[0022]
Embedded image
Further, the compound represented by the general formula (2) or (3) can be produced by the following route.
[0023]
Embedded image
Commercially available 3-nitrophthalonitrile (A) is converted to R 4 OH [R 4 represents an alkyl group in the presence of a base. To give alkoxyphthalonitrile (B). Further, (B) is reacted in a high-boiling solvent such as dialkylaniline or DMI to produce the target compound represented by the general formula (2) or (3) alone or a mixture thereof. Can be separated by a method such as column chromatography to obtain the target compound represented by the general formula (2) or (3) alone.
[0025]
Examples of the alcohol derivative represented by R 4 OH include 1-butyn-3-ol, 3-methyl-1-butyn-3-ol, 1-pentyn-3-ol, 1-hexyn-3-ol, -Methyl-1-pentyn-3-ol, 3,4-dimethyl-1-pentyn-3-ol, 1-heptin-3-ol, 3-ethyl-1-pentyn-3-ol, 5-methyl-1 -Hexyn-3-ol, 3-methyl-1-hexyn-3-ol, 3-methyl-4-hexyn-3-ol, 3,5-dimethyl-1-hexyn-3-ol, 3,4,4 -Trimethyl-1-penten-3-ol, 4-ethyl-1-hexyn-3-ol, 1-ethynyl-1-cyclohexanol, 1-octin-3-ol, 3,6-dimethyl-1-heptin- 3-ol, 3- Chill-1-heptyn-3-ol, 3-ethyl-5-methyl-1-heptyn-3-ol, 4-ethyl-1-octyn-3-ol, and the like.
[0026]
As a method for producing an optical recording medium using the phthalocyanine compound of the present invention, there is a method in which one or two layers of one to three kinds of compounds including the phthalocyanine compound of the present invention are coated or deposited on a transparent substrate. As a coating method, the binder resin is dissolved in a solvent so as to be 20% by weight or less, preferably 0%, and 0.05 to 20% by weight, preferably 0.5 to 20% by weight of the phthalocyanine compound of the present invention, There is a method of applying with a spin coater. As a vapor deposition method, there is a method of depositing a phthalocyanine compound on a substrate at 10-5 to 10-7 torr and 100 to 300 ° C.
[0027]
The substrate may be any optically transparent resin. For example, acrylic resin, polyethylene resin, vinyl chloride resin, vinylidene chloride resin, polycarbonate resin, polyolefin copolymer resin, vinyl chloride copolymer resin, vinylidene chloride copolymer resin, styrene copolymer resin and the like can be mentioned. The substrate may be subjected to a surface treatment with a thermosetting resin or an ultraviolet curable resin.
[0028]
When an optical recording medium (such as an optical disk or an optical card) is manufactured, it is preferable to use a polyacrylate substrate or a polycarbonate substrate and apply the substrate by a spin coating method in terms of cost and handling by a user.
[0029]
From the viewpoint of the solvent resistance of the substrate, solvents used for spin coating include halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, tetrachloroethylene, dichlorodifluoroethane, etc.) and ethers (eg, tetrahydrofuran, diethyl ether, dipropyl ether, Dibutyl ether, dioxane, etc.), alcohols (eg, methanol, ethanol, propanol, etc.), cellosolves (eg, methyl cellosolve, ethyl cellosolve, etc.), hydrocarbons (eg, hexane, cyclohexane, ethylcyclohexane, cyclooctane, dimethyl) Cyclohexane, octane, benzene, toluene, xylene, etc.) or a mixed solvent thereof is preferably used.
[0030]
To process as a recording medium, the substrate is covered with a substrate as described above, or bonded to a substrate provided with two recording layers with an air gap provided therebetween, or a reflective layer (aluminum or aluminum) is formed on the recording layer. Gold) and laminating a protective layer of a thermosetting or photocurable resin. As the protective layer, an inorganic compound such as Al 2 O 3 , SiO 2 , SiO, and SnO 2 may be used.
[0031]
【Example】
Hereinafter, the present invention will be described specifically with reference to examples, but embodiments of the present invention are not limited thereto.
[0032]
Example 1
The following structural formula (3-1)
[0033]
Embedded image
The results of the visible absorption spectrum and the elemental analysis were as follows.
[0034]
Embedded image
An n-octane solution (10 g / l) of the above phthalocyanine compound is coated with a spiral groove (pitch: 1.6 μm, groove width: 0.6 μm, groove depth: 0.18 μm) with an outer shape of 120 mm and a thickness of 1.2 mm for CD-R polycarbonate. Spin coating was performed on the substrate at 500 to 1000 rpm. A reflective layer was formed thereon by sputtering 30 nm of gold, followed by overcoating with a photocurable polyacrylic resin, followed by photocuring to form a protective layer, thereby producing a CD-R medium. The reflectivity of this medium is 71% (775 to 790 nm), and an EFM signal can be written at a linear velocity of 1.3 m / sec with a power of 5.5 mW using a 780 nm semiconductor laser. It was less than 10.
[0037]
Example 2
A mixture of 22.4 g (0.1 mol) of the phthalonitrile derivative represented by the structural formula (3-1), 15.2 g (0.1 mol) of DBU, and 125 g of n-amyl alcohol was heated at 100 ° C. under a nitrogen atmosphere. Temperature. Next, 5.3 g (0.03 mol) of palladium chloride was added at the same temperature, and reacted at 95 to 100 ° C. for 30 hours. After the completion of the reaction, the mixture was cooled and insolubles were removed by filtration. After the filtrate was concentrated under reduced pressure to recover the solvent, column purification was performed (silica gel 500 g, solvent toluene) to obtain 12.0 g (yield 48%) of a phthalocyanine compound represented by the following structural formula (1-2).
The results of the visible absorption spectrum and the elemental analysis were as follows.
[0038]
Embedded image
An n-octane solution (10 g / l) of the above phthalocyanine compound is coated with a spiral groove (pitch: 1.6 μm, groove width: 0.6 μm, groove depth: 0.18 μm) with an outer shape of 120 mm and a thickness of 1.2 mm for CD-R polycarbonate. Spin coating was performed on the substrate at 500 to 1000 rpm. A reflective layer was formed thereon by sputtering 30 nm of gold, followed by overcoating with a photocurable polyacrylic resin, followed by photocuring to form a protective layer, thereby producing a CD-R medium. When recording with a 780 nm semiconductor laser, a CN ratio of 60 dB was obtained with a power of 7 mW. Change even if the playback 10 5 times in the reproduction light of 0.5mW was not observed. Further, there was no change in the recording even after 1000 hours under the condition of 80 ° C./80% RH.
[0041]
Example 3
The following structural formula (2-1)
[0042]
Embedded image
The results of the visible absorption spectrum and the elemental analysis were as follows.
[0043]
Embedded image
An n-octane solution (10 g / l) of the above phthalocyanine compound is coated with a spiral groove (pitch: 1.6 μm, groove width: 0.6 μm, groove depth: 0.18 μm) with an outer shape of 120 mm and a thickness of 1.2 mm for CD-R polycarbonate. Spin coating was performed on the substrate at 500 to 1000 rpm. A reflective layer was formed thereon by sputtering 30 nm of gold, followed by overcoating with a photocurable polyacrylic resin, followed by photocuring to form a protective layer, thereby producing a CD-R medium. The reflectance of this medium is 73% (775 to 790 nm), and an EFM signal can be written at a linear velocity of 1.3 m / sec with a power of 6.0 mW using a 780 nm semiconductor laser. It was less than 10.
[0046]
Example 4
A mixture of 22.4 g (0.1 mol) of the phthalonitrile derivative represented by the structural formula (2-1), 15.2 g (0.1 mol) of DBU and 125 g of n-amyl alcohol was heated at 100 ° C. under a nitrogen atmosphere. Temperature. Next, 5.3 g (0.03 mol) of palladium chloride was added at the same temperature, and reacted at 95 to 100 ° C. for 35 hours. After the completion of the reaction, the mixture was cooled and insolubles were removed by filtration. After the filtrate was concentrated under reduced pressure to recover the solvent, column purification was performed (silica gel 500 g, solvent toluene) to obtain 14.6 g (yield 61%) of a phthalocyanine compound represented by the following structural formula (1-4).
The results of the visible absorption spectrum and the elemental analysis were as follows.
[0047]
Embedded image
A CD-R type medium was produced in the same manner as in Example 1 using the above phthalocyanine compound. The error rate when writing an EFM signal with a power of 6.0 mW at a linear velocity of 1.3 m / s using a laser having a wavelength of 780 nm on this medium was less than 10.
[0050]
Example 5
The following structural formula (3-2)
[0051]
Embedded image
The results of the visible absorption spectrum and the elemental analysis were as follows.
[0052]
Embedded image
A CD-R type medium was produced in the same manner as in Example 1 using the above phthalocyanine compound. The error rate when writing an EFM signal with a power of 6.0 mW at a linear velocity of 1.3 m / s using a laser having a wavelength of 780 nm on this medium was less than 10.
[0055]
Example 6
The following structural formula (2-2)
[0056]
Embedded image
The results of the visible absorption spectrum and the elemental analysis were as follows.
[0057]
Embedded image
A CD-R type medium was produced in the same manner as in Example 1 using the above phthalocyanine compound. The error rate when writing an EFM signal with a power of 6.0 mW at a linear velocity of 1.3 m / s using a laser having a wavelength of 780 nm on this medium was less than 10.
[0060]
Example 7
A mixture of 26.6 g (0.1 mol) of the phthalonitrile derivative represented by the structural formula (2-2), 15.2 g (0.1 mol) of DBU and 125 g of n-amyl alcohol was heated at 100 ° C. under a nitrogen atmosphere. Temperature. Next, 5.3 g (0.03 mol) of palladium chloride was added at the same temperature, and the mixture was reacted at 95 to 100 ° C. for 33 hours. After the completion of the reaction, the mixture was cooled and insolubles were removed by filtration. After the filtrate was concentrated under reduced pressure to recover the solvent, the residue was purified by column (500 g of silica gel, solvent of toluene) to obtain 14.1 g (yield: 48%) of a phthalocyanine compound represented by the following structural formula (1-7).
The results of the visible absorption spectrum and the elemental analysis were as follows.
[0061]
Embedded image
A CD-R type medium was produced in the same manner as in Example 1 using the above phthalocyanine compound. The error rate when writing an EFM signal with a power of 6.0 mW at a linear velocity of 1.3 m / s using a laser having a wavelength of 780 nm on this medium was less than 10.
[0064]
Example 8
The following structural formula (2-3)
[0065]
Embedded image
The results of the visible absorption spectrum and the elemental analysis were as follows.
[0066]
Embedded image
A CD-R type medium was produced in the same manner as in Example 1 using the above phthalocyanine compound. The error rate when writing an EFM signal with a power of 6.0 mW at a linear velocity of 1.3 m / s using a laser having a wavelength of 780 nm on this medium was less than 10.
[0069]
Comparative Example 1
A medium prepared in the same manner as in Example 1 using the exemplified compound of JP-A-3-62878 (US Pat. No. 5,240,067) represented by the following structural formula (C) was evaluated.
[0070]
Embedded image
Using a 780 nm semiconductor laser for this medium, a power of 10 mW was required to write an EFM signal at a linear velocity of 1.3 m / s. The error rate at that time was 12.
[0072]
Examples 9 to 20
The phthalocyanine compounds shown in the following Table 1 were synthesized in the same manner as in Example 1, and a CD-R medium was produced in the same manner as in Example 1 and at a linear velocity of 1.3 m / s using a 780 nm semiconductor laser. The laser power (mw) required to write the EFM signal was measured, and the error rate at that time was evaluated. Regarding the evaluation of the error rate, ○ indicates that the error rate is less than 10, and X indicates that the error rate is 10 or more. The results are shown in Table 1.
[0073]
[Table 1]
【The invention's effect】
The phthalocyanine compound of the present invention is a novel phthalocyanine compound in which a hetero ring is condensed with a phthalocyanine ring, and since this hetero ring is conjugated with a phthalocyanine ring, it is easy to control the absorption wavelength region, and at the time of recording, Pit formation with high precision by controlling the decomposition and melting of the resin, reduced damage to the resin substrate of the recording medium due to reduced heat generation, Adhesion with the metal layer, which is a layer, contributed to the improvement, and in an optical recording medium using this compound, a signal at the time of optical recording can be correctly written, and the effect of improving sensitivity and recording characteristics was improved.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31165294A JP3604432B2 (en) | 1994-12-15 | 1994-12-15 | Phthalocyanine compound and optical recording medium containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31165294A JP3604432B2 (en) | 1994-12-15 | 1994-12-15 | Phthalocyanine compound and optical recording medium containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08165439A JPH08165439A (en) | 1996-06-25 |
| JP3604432B2 true JP3604432B2 (en) | 2004-12-22 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31165294A Expired - Fee Related JP3604432B2 (en) | 1994-12-15 | 1994-12-15 | Phthalocyanine compound and optical recording medium containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3604432B2 (en) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197280A (en) * | 1985-02-27 | 1986-09-01 | Tdk Corp | Optical recording medium |
| JPS6337991A (en) * | 1986-08-01 | 1988-02-18 | Toyo Ink Mfg Co Ltd | Optical recording medium |
| JPS6339388A (en) * | 1986-08-05 | 1988-02-19 | Kao Corp | Optical information recording medium |
| EP0346354B1 (en) * | 1987-02-13 | 1992-08-19 | The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and | Substituted phthalocyanines |
| JPH0239160A (en) * | 1988-07-29 | 1990-02-08 | Canon Inc | Electrophotographic sensitive body |
| DE68928559T2 (en) * | 1988-12-15 | 1998-06-18 | Mitsui Toatsu Chemicals | Near infrared absorbent and display / recording materials made therefrom |
| JP2635840B2 (en) * | 1990-06-19 | 1997-07-30 | 三井東圧化学株式会社 | Optical card |
| JP3126411B2 (en) * | 1990-06-22 | 2001-01-22 | 三井化学株式会社 | Optical recording medium and recording method |
| JPH07292272A (en) * | 1994-04-28 | 1995-11-07 | Mitsui Toatsu Chem Inc | Phthalocyanine compound and optical recording medium containing the same |
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1994
- 1994-12-15 JP JP31165294A patent/JP3604432B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08165439A (en) | 1996-06-25 |
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