CN1169128A - 光记录材料和光记录介质 - Google Patents
光记录材料和光记录介质 Download PDFInfo
- Publication number
- CN1169128A CN1169128A CN96191531A CN96191531A CN1169128A CN 1169128 A CN1169128 A CN 1169128A CN 96191531 A CN96191531 A CN 96191531A CN 96191531 A CN96191531 A CN 96191531A CN 1169128 A CN1169128 A CN 1169128A
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- Prior art keywords
- group
- replacement
- formula
- alkyl
- aryl
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- 230000003287 optical effect Effects 0.000 title claims abstract description 27
- 239000000463 material Substances 0.000 title claims abstract description 26
- -1 azo compound Chemical class 0.000 claims abstract description 179
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052733 gallium Inorganic materials 0.000 claims abstract description 5
- 229910052718 tin Inorganic materials 0.000 claims abstract description 4
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 3
- 229910052738 indium Inorganic materials 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 3
- 125000001769 aryl amino group Chemical group 0.000 claims abstract 5
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 150000004696 coordination complex Chemical class 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 230000001681 protective effect Effects 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 150000003624 transition metals Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims 4
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 230000035945 sensitivity Effects 0.000 abstract description 15
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 239000000843 powder Substances 0.000 description 34
- 239000010408 film Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000975 dye Substances 0.000 description 18
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 16
- 238000000434 field desorption mass spectrometry Methods 0.000 description 14
- 238000003860 storage Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 230000002194 synthesizing effect Effects 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000013049 sediment Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000002562 thickening agent Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000009987 spinning Methods 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000000197 pyrolysis Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- XCQQWDCKLLORFE-UHFFFAOYSA-N [O].C1(=CC=CC=C1)PC1=CC=CC=C1 Chemical compound [O].C1(=CC=CC=C1)PC1=CC=CC=C1 XCQQWDCKLLORFE-UHFFFAOYSA-N 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- ZILCTNWIPQCEPU-UHFFFAOYSA-N cyclopenta-1,3-diene cyclopenta-2,4-diene-1-sulfonic acid iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.OS(=O)(=O)[c-]1cccc1 ZILCTNWIPQCEPU-UHFFFAOYSA-N 0.000 description 4
- JHKWXZZEBNEOAE-UHFFFAOYSA-N dihydroxysilicon Chemical compound O[Si]O JHKWXZZEBNEOAE-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000700 radioactive tracer Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000001007 phthalocyanine dye Substances 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 0 *=*c(cc1)cc(C(c2c3cccc2)=O)c1C3=O Chemical compound *=*c(cc1)cc(C(c2c3cccc2)=O)c1C3=O 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- AELZBYQHJCEGBO-UHFFFAOYSA-N CC(C)(C)C[O] Chemical compound CC(C)(C)C[O] AELZBYQHJCEGBO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 125000004986 diarylamino group Chemical group 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N 1-methyl-2,5-dihydropyrrole Chemical compound CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- GSMZLBOYBDRGBN-UHFFFAOYSA-N 2-fluoro-2-methylpropane Chemical compound CC(C)(C)F GSMZLBOYBDRGBN-UHFFFAOYSA-N 0.000 description 1
- QFQUCEPMKAJNJC-UHFFFAOYSA-N 3-[[4-(diethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound C1=CC(N(CC)CC)=CC=C1N=NC1=CC=CC(S(O)(=O)=O)=C1 QFQUCEPMKAJNJC-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 description 1
- UDFCHANCMRCOQT-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonyl chloride Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)Cl)=CC=C3C(=O)C2=C1 UDFCHANCMRCOQT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JZZUXZBIESALDD-UHFFFAOYSA-N C(C)(C)OCC(C(OOC(C)(C)C)(OCC(C)C)OCCCC)(C)C Chemical compound C(C)(C)OCC(C(OOC(C)(C)C)(OCC(C)C)OCCCC)(C)C JZZUXZBIESALDD-UHFFFAOYSA-N 0.000 description 1
- GXMNNKNWIAGVIO-UHFFFAOYSA-N CC1=C(C=CC(=C1)[N+](=O)[O-])OOC1=CC=CC=C1 Chemical compound CC1=C(C=CC(=C1)[N+](=O)[O-])OOC1=CC=CC=C1 GXMNNKNWIAGVIO-UHFFFAOYSA-N 0.000 description 1
- SBQGUXXGFKAZIZ-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCOCCCCCCCC.[O] Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCC.[O] SBQGUXXGFKAZIZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- YMOKYSFFKRRWKD-UHFFFAOYSA-N O[Ge]O Chemical compound O[Ge]O YMOKYSFFKRRWKD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
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- DLYLXYLRSRVMGE-UHFFFAOYSA-N [PH2](=O)O[Si]O Chemical compound [PH2](=O)O[Si]O DLYLXYLRSRVMGE-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
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- YCSBALJAGZKWFF-UHFFFAOYSA-N anthracen-2-amine Chemical compound C1=CC=CC2=CC3=CC(N)=CC=C3C=C21 YCSBALJAGZKWFF-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N beta-hydroxynaphthyl Natural products C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000013500 data storage Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- SLIKWWJXVUHCPJ-UHFFFAOYSA-N n-(dimethylazaniumyl)ethanimidate Chemical compound CN(C)NC(C)=O SLIKWWJXVUHCPJ-UHFFFAOYSA-N 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
一种下式(1)的光记录材料和具有优异记录灵敏度,耐光性和耐用性的光记录介质,所述介质含有含上述材料的记录层,式(1),其中各X1-X4为氢原子,烷基,芳基,脂环残基,芳烷基,杂环,烷氧基,芳氧基或烷基硫代基,各Y1-Y4为氢原子,卤原子,硝基,邻苯二甲酰亚胺甲基或砜酰胺基,各R1和R2为氢原子,卤原子,羟基,烷基,芳基,芳烷基,烷氧基,芳氧基,烷基硫代基,芳基硫代基,烷基氨基,二烷基氨基,芳基氨基或二芳基氨基,M为Al,Ga,In,Si,Ge或Sn,Z为偶氮化合物,蒽醌化合物或金属配位化合物,n1-n4为1-4的整数,m1-m4为0-4的整数,k为1或2,和1为0或1,但k+1为1或2。
Description
技术领域
本发明涉及用激光来读写数据的光记录介质。更具体地说,本发明涉及用于一次写入的激光磁盘(CD-R)(write-once compact disk)的光记录膜材料,记录膜组合物和介质构成。
技术背景
目前,作为具有编辑功能的一次写入的光盘,实际上使用由有机染料(如花青)制成的记录膜上覆以的金反射膜的CD-R,在波长为780nm时记录下CD格式或CD-ROM格式信号并用CD或CD-ROM再现器读出数据。然而,由于花青染料的光稳定性通常是差的,具有单一表面结构的CD或CD-ROM如直接暴露于阳光下使用其数据可靠性的危险有待研究。
因此,有人试图使用物理化学稳定的酞菁染料作为记录膜材料来代替花青染料。JP-B-4-53713,JP-A-4-214388和JP-A-5-1272提出使用酞菁化合物,其中一些实际上已被使用。使用上述酞菁材料的CR-R具有与那些使用花青染料的CD-R相同的特征,并根据“桔皮书”(“Orange Book”)作为介质进行工作,其中一些在耐光性上优于使用花青染料的介质。
近年来随着CD-ROM越来越广泛地使用,要求CD-R介质满足快速存取存储和快速存取读出,要求一种介质不仅适应随机存取存储,而且适应双倍速率和四倍速率的存储。由于与上述花青染料相比酞菁染料的记录灵敏度通常是差的,酞菁染料不能满足上述所有这些要求。因此,为了改进记录灵敏度,必需如JP-A-7-20550中所述引入可高度热解的取代基以改进染料结构,或必需如JP-A-59-92448中所述与热解促进添加剂结合使用。上述技术成功地获得了能满足快速存取存储的记录灵敏度,但它通常是以牺牲耐用性和耐光性达到的。但是,由于记录灵敏度的改进,存储特征的稳定性由于记录槽的不稳定形式而变得不足了,因而更难以获得与市场上买得到的所有CD唱机都能很好兼容的CD-R。因此,如JP-B-5-58915和JP-A-7-98887中所述,通过加入能改进记录膜表面层性能的试剂或能控制记录槽形式的试剂来稳定存储信号的特征,在这方面作了努力。然而,记录层构造复杂,并且与只使用染料的情况相比,产率低。另外,由于这些试剂本身耐光性差,因此还存在可靠性差的问题。
本发明的发明者为克服上述问题作了努力的研究,结果,他们发现的一种光记录介质是在记录层中加入特定结构的酞菁化合物作为有机染料,获得适合快速存取存储的记录灵敏度,改进了耐光性和耐用性上的可靠性并稳定了记录特征,从而完成了本发明。
本发明的描述
本发明1是一种光记录材料,它是具有式(1)特定结构的酞菁化合物,该化合物作为有机染料用于包括透明基材的四层组成的光记录介质中的记录层。记录层由有机染料,反射层和保护层组成,
其中各X1-X4独立地为氢原子,烷基,取代的烷基,芳基,取代的芳基,脂环残基,取代的脂环残基,芳烷基,取代的芳烷基,杂环,取代的杂环,烷氧基,取代的烷氧基,芳氧基,取代的芳氧基,烷基硫代基或取代的芳基硫代基,
各Y1-Y4独立地为氢原子,卤原子,硝基,邻苯二甲酰亚胺甲基(phthalimidemethyl group),取代的邻苯二甲酰亚胺甲基,砜酰胺基或取代的砜酰胺基,
各R1和R2独立地为氢原子,卤原子,羟基,烷基,取代的烷基,芳基,取代的芳基,芳烷基,取代的芳烷基,烷氧基,取代的烷氧基,芳氧基,取代的芳氧基,烷基硫代基,取代的烷基硫代基,芳基硫代基,取代的芳基硫代基,烷氨基,取代的烷氨基,二烷氨基,取代的二烷氨基,芳氨基,取代的芳氨基,二芳氨基或取代的二芳氨基,
M为Al,Ga,In,Si,Ge或Sn,
Z为下式(2)-(6)之一的偶氮化合物,蒽醌化合物或金属配位化合物,
n1-n4为取代基X1-X4的数目,它们分别独立地为1-4的整数,
m1-m4为取代基Y1-Y4的数目,它们分别独立地为0-4的整数,
k为轴向取代基-OSO2-Z的数目,它为1或2,和
l为轴向取代基-OP(=O)R1R2的数目,它为0或1,但k+l为1或2。
式(2),
其中各R3,R4和R5独立地为氢原子,卤原子,羟基,硝基,氰基,羧酸基,羧酸酯基,磺酸基,磺酸酯基,烷基,取代的烷基,芳基,取代的芳基,环烷基,取代的环烷基,芳烷基,取代的芳烷基,杂环,取代的杂环,烷氧基,取代的烷氧基,芳氧基,取代的芳氧基,烷基硫代基,取代的烷基硫代基,芳基硫代基,取代的芳基硫代基,氨基,烷氨基,取代的烷氨基,二烷氨基,取代的二烷氨基,芳氨基或取代的芳氨基,
n5为取代基R3的数目,它为0-4的整数,n6和n7为取代基R4和R5的数目,它们分别为0-5的整数。
其中R3-R6与式(2)中R3-R5的含义相同,n5-n8为取代基R3-R6的数目,它们分别为0-3的整数。式(5),
其中A1和A2为苯环或萘环,R3-R6与式(2)中R3-R5的含义相同,n5-n8为取代基R3-R6的数目,它们分别为0-3的整数,M1为过渡金属原子。
其中R3和R4与式(2)中R3-R5的含义相同,n5为取代基R3的数目,它为0-4的整数,n6为取代基R4的数目,它为0-5的整数,M2为过渡金属。
当酞菁化合物含有一含磺酸基的化合物作为轴向取代基时,磺酸即和中心金属相互离子键合在一起,在特征上,轴向取代基改进了耐光性和耐用性上的可靠性并提供稳定的记录特征。酞菁化合物最好具有不对称结构,在其中引入由含磷化合物形成的取代基和由含磺酸基的化合物形成的取代基作为相对于中心金属的轴向取代基,或者这些轴向取代基只由含磺酸基的化合物形成的取代基所形成。
本发明2是含记录层的光记录介质,所述记录层至少含一种上述特定结构的酞菁化合物。
本发明的发明者以前发现,具有相对于中心金属的特定的轴向取代基如磷酸酯基和膦酸酯基结构的酞菁化合物具有显著优异的耐光性(JP-A-4-214388,着色材料研究布告预印本,1994,11B-12)并成功地获得了耐光性优异的光记录介质。然而,上述酞菁化合物近年来在适应快速存取存储的记录灵敏度方面并不令人满意。
为改进记录灵敏度,如JP-A-7-20550中所述必需引入可高度热解的大体积取代基来改进染料结构以抑制酞菁分子的结合性并提高热解性,或者如JP-A-59-24228中所述必需结合使用能促进热解的添加剂。这些技术能获得能适应快速存取存储的记录灵敏度,但在通常情况下是以牺牲耐用性和耐光性为代价的。而且,由于记录灵敏度的改进,存储特征的稳定性由于数据存储槽的不稳定形式而变得不足了,因而更难以获得与市场上买得到的所有CD唱机都能很好兼容的CD-R。因此,如JP-B-5-58915和JP-A-7-98887中所述,加入能改进记录膜表面层性能的试剂或加入能控制数据存储槽形式的试剂可稳定存储信号的特征,他们在这方面作了努力。然而,记录层因而具有复杂的构造,且与只使用染料的情况相比,存在产率低的问题。
Sato等人提出一种光记录介质使用含特定结构轴向取代基的酞菁化合物,(JP-A-3-281386)。然而,不仅上述提出的化合物不能达到充分适应快速存取存储的记录灵敏度,而且由于一些化合物的耐光性差或由于一些化合物对记录特征具有相反的效应还存在记录特征稳定性问题。
JP-A-5-279580和JP-A-6-65514披露了使用偶氮化合物或其金属配位化合物作为光记录材料的实例,还披露了另一个将它与酞菁化合物结合起来使用以改进记录灵敏度的实例。然而,没有发现一个实例是象本发明那样将它键合到酞菁化合物的轴向取代基上来制备光记录材料以改进记录特征。
JP-A-7-98887披露了作为控制数据存储槽形式的试剂的许多金属配位化合物。然而,它们全部是用作改进光记录材料(如酞菁化合物)的记录特征的添加剂,它们中没有一个记录层所用的有机染料成为一体化结构。而且,业已表明由于上述金属配位化合物能控制记录时间内所产生的热量,已可有效地控制数据存储槽的形式,从而改进所记录的信号。然而,上述金属配位化合物本身的耐光性差是一个问题。例如,当将它们与酞菁化合物一起使用时,大部分情况下,酞菁化合物本身的耐光性不能保持。
本发明的发明者作了深入研究发现,具有特定结构的酞菁化合物,含有式(2)-(6)中任何一种偶氮化合物、蒽醌化合物或金属配位化合物通过磺酸基能克服上述所有三个问题,也就是说,它具有能适应快速存取存储的记录灵敏度,具有优异的耐光性和耐用性,并在记录时间内形成合适的数据存储槽,其记录特征是稳定的。本发明的发明者因而成功地获得了价廉并且高产率的光记录介质。
本发明各式化合物的结构及其取代基将在下面作详细说明。在式中,卤原子包括氟,氯,溴和碘。可以带取代基的烷基包括甲基,乙基,丙基,异丙基,丁基,异丁基,叔丁基,新戊基,正己基,正辛基,十八烷基,2-乙基己基,三氯甲基,三氟甲基,2,2,2-三氟乙基,2,2-二溴乙基,2,2,3,3-四氟丙基,2-乙氧基乙基,2-丁氧基乙基和2-硝基丙基。可以带取代基的芳基包括苯基,萘基,蒽基,对甲苯基,对硝基苯基,对甲氧基苯基,2,4-二氯苯基,五氟苯基,2-氨基苯基,2-甲基-4-氯苯基,4-羟基-1-萘基,6-甲基-2-萘基,4,5,8-三氯-2-萘基,蒽二酚基(anthraquinolyl)和2-氨基蒽二酚基。可以带取代基的脂环残基包括环戊基,2,5-二甲基环戊基,环己基,4-叔丁基环己基和金刚烷基。可以带取代基的芳烷基包括苄基,4-甲基苄基,4-叔丁基苄基,4-甲氧基苄基,4-硝基苄基和2,4-二氯苄基。可以带有取代基的杂环残基包括吡啶基,3-甲基吡啶基,吡嗪基,哌啶基,N-甲基哌啶基,吡喃基,morphonyl, N-甲基吡咯啉基和吖啶基。可以带取代基的烷氧基包括甲氧基,乙氧基,丙氧基,异丙氧基,正丁氧基,异丁氧基,叔丁氧基,新戊氧基,正己氧基,正辛氧基,十八烷氧基,2-乙基己氧基,三氯甲氧基,三氟甲氧基,2,2,2-三氟乙氧基,2,2,3,3-四氟丙氧基,2-乙氧基乙氧基,2-丁氧基乙氧基和2-硝基丙氧基。可以带取代基的芳氧基包括苯氧基,萘氧基,蒽氧基,对甲基苯氧基,对硝基苯氧基,对甲氧基苯氧基,2,4-二氯苯氧基,五氟苯氧基和2-甲基-4-氯苯氧基。可以带有取代基的烷氨基包括甲基氨基,乙基氨基,二甲基氨基,二乙基氨基,二异丙基氨基和环己基氨基。可以带取代基的芳氨基包括苯基氨基,对硝基苯基氨基,4-甲基苯基氨基,二苯基氨基和二(4-甲氧基苯基)氨基。上述化合物是例子,各基团并不局限于此。
结构上含有特定轴向取代基(由式(1)表示)的本发明酞菁化合物的典型例子包括下述酞菁化合物(a)-(n)。
酞菁化合物(e)
酞菁化合物(i)
酞菁化合物(j)
酞菁化合物(k)
酞菁化合物(l)
记录层可由干法和湿法中的任何一种方法来制造。干法包括真空沉积法和喷溅法。湿法包括纺涂法,浸涂法,喷雾法,辊涂法和LB(Langmuir-Blodgett)法。本发明的记录膜材料在常用的有机溶剂如含醇,含酮,含溶纤剂,含卤,含烃和含氯氟烃的溶剂中有高的溶解度,并且从记录膜的产率和均匀性来看最好用纺涂法制造记录层。在使用上述方法时,需要时可以加入聚合物粘合剂。
聚合物粘合剂包括环氧树脂,丙烯酸树脂,聚碳酸酯树脂,聚酯树脂,聚酰胺树脂,聚氯乙烯树脂,硝基纤维素树脂和酚醛树脂,尽管聚合物粘合剂并不局限于这些。对聚合物粘合剂的混和比并无特别限制,若以染料为计算基准聚合物粘合剂的量较好地为30%或更少。本发明中记录层的最佳膜厚视记录膜材料的种类和组合而定,因此并无特别限制,但以500-3,000埃较好,800-1,500埃更好。
本发明中反射层所用的材料包括金属如金,银,铜,铂,铝,钴和锡,及以这些金属为主要成分的合金,氧化物和氮化物,其中以金最为合适,因它具有高的绝对反射度且安全性非常好。在一些情况下可以使用有机化合物的高反射膜。作为制造反射膜的方法,干法如真空沉积法或喷溅法是最好的,但方法并不局限于此。对反射膜的最佳膜厚并无特别限制,但以400-1,600埃较好。
另外,在反射膜上形成保护膜以保护盘。作为保护膜材料,用可紫外线固化的树脂为宜,保护膜较好地经下述方法制造,即用纺涂法施涂可紫外线固化的树脂,而后用紫外线辐射进行固化,但材料和方法并不局限于此。保护层的膜厚宜为2-20μm,因较薄的膜效果差,而较厚的膜会导致机械性能差,如由于树脂固化时发生的收缩会引起盘的变形。
本发明所用的盘基材对读写信号的透光率至少为85%较好,并且具有较小的光学各向异性。盘基材的例子包括玻璃,热塑性树脂如丙烯酸树脂,聚碳酸酯树脂,聚酯树脂,聚酰胺树脂,聚苯乙烯树脂和聚烯烃树脂,以及热固性树脂如环氧树脂和丙烯酸树脂等。其中,由热塑性树脂制成的基材是较好的,因它易于模塑并易于提供ATIP波动信号和导槽。从光学特性,机械性能和费用来看,丙烯酸树脂或聚碳酸酯树脂制成的基材是特别好的。
对基材中的导槽的形状并无特别限制,可以是梯形,U字形或V字形。导槽尺寸的最佳值视记录膜材料的种类和组合而定。通常,平均槽宽(槽中高度为1/2槽深处的宽度)宜为0.4-0.6μm,槽深宜为1,000-2,000埃。要求本发明的盘在完成记录后能用作CD或CD-ROM,因此根据CD-ROM标准(红皮书(Red Book))和CD-R标准(桔皮书)较好。
本发明的式(1)酞菁化合物可单独使用或结合使用。为了平衡记录特征,可以加入其它酞菁化合物一起使用,要求这个“其它酞菁化合物”具有优异的耐光性和耐用性。较好的是如在JP-A-4-214388中所披露的具有优异耐光性的酞菁化合物,它具有磷酸酯和膦酸酯基键合到中心金属上的特定轴向取代基的结构。
式(1)酞菁化合物可以这样制备,在合适的溶剂中,将含中心金属,含羟基的酞菁化合物与作为轴向取代基引入的偶氮化合物,蒽醌化合物或金属配位化合物的磺酸或磺酰卤(反应试剂)反应。当酞菁化合物所含中心金属为三价时如Al或Ga酞菁化合物可与上述含磺酸基的化合物形成盐,即使酞菁化合物具有特定轴向取代基如磷酸酯基或膦酸酯基的结构时也是如此。在这种情况下,中心金属和磺酸基相互离子键合在一起。
本发明将参考下述实施例作详细说明。
合成实施例1
酞菁化合物(a)的合成
将3.0 g二羟基硅四〔2,2’-双(三氟甲基)丙氧基〕酞菁溶解在100ml N-甲基吡咯烷酮中,加入1.0g3-(2-氯-4-羟苯基偶氮)苯磺酸,将混合物在80℃下加热搅拌2小时。将反应混合物倒入2.0l冰水中,过滤回收沉淀的晶体,用水洗并干燥,获得蓝色粉末。将粉末溶解在200ml氯仿中,过滤除去不溶物。蒸馏除去滤液中的溶剂,获得1.6g蓝绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(a)。
合成实施例2
酞菁化合物(b)的合成
除了二羟基硅四〔2,2’-双(三氟甲基)丙氧基〕酞菁被羟基铝四溴四(2,2,3,3-四氟丙氧基)酞菁代替,以及3-(2-氯-4-羟苯基偶氮)苯磺酸被3-(4-二乙基氨基苯基偶氮)苯磺酸代替外,与合成实施例1相同的方式获得1.2g蓝绿色粉末。与FD-MS分析该粉末,表明它为酞菁化合物(b)。
合成实施例3
将3.2g羟基铝八氯四〔2,2’-双(三氟甲基)丙氧基〕酞菁溶解在80ml无水环丁砜(sulforan スルホラソ)中,加入1.0g偶氮染料(如下式)的磺酸,将混合物在100℃下加热搅拌2小时。将反应混合物倒入1.01冰水中,过滤回收所得的沉淀物,用水洗,获得蓝绿色糊料。将糊料溶解在600ml甲醇中,过滤除去不溶物。然后,在滤液中滴加入150ml水,将混合物搅拌3小时。过滤回收所得的沉淀物,用金属/水(4/1)的混和液体洗涤,干燥,获得0.6g蓝绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(c)。
合成实施例4
酞菁化合物(d)的合成
将2.8g羟基铝四溴四(新戊氧基)酞菁和0.5g吡啶加入150ml二噁烷中,然后,徐徐加入4.0g蒽醌-2-磺酰氯,在加热下使混合物回流2小时。冷却反应混合物,在减压下蒸馏除去溶剂。将剩余物溶解在400ml乙醇中,过滤除去不溶物。然后,在滤液中滴加100ml水,将混合物搅拌3小时。过滤回收所得的沉淀物,用金属/水(4/1)的混和液体洗涤,干燥,获得1.1g蓝绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(d)。
合成实施例5
酞菁化合物(e)的合成
将3.2g二羟基硅四〔2,2’-双(三氟甲基)丙氧基〕酞菁溶解在10ml二甲基氨基乙酰胺中,加入1.0g铜配位化合物(如下式)的磺酸,将混合物在90℃下加热搅拌4小时。将反应混合物倒入1.01冰水中,过滤回收所得的沉淀物,用水洗,获得绿色糊料。将糊料溶解在800ml甲苯中,过滤除去不溶物。用水洗剩余物,用硫酸镁干燥,蒸馏除去溶剂,获得1.6g绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(e)。
合成实施例6
酞菁化合物(f)的合成
将3.0g羟基铝四〔(2-甲基)丁氧基〕酞菁和1.0g正丁基二茂铁磺酸加入150ml甲苯中,在加热下使混合物回流3小时。过滤反应混合物,用50ml乙醇洗涤所得的产物,干燥,获得2.2g蓝绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(f)。
合成实施例7
酞菁化合物(g)的合成
将3.2g羟基铝八氯四〔2,2’-双(三氟甲基)丙氧基〕酞菁和1.5g二茂铁磺酰氯加入150ml苯中,再加入0.5g吡啶,在加热下使混合物回流3小时。冷却反应混合物,用350ml苯稀释,滴加300ml己烷。将混合物搅拌2小时。过滤回收沉淀的晶体,然后用苯/己烷(2/1)的混合溶剂洗涤,干燥,获得2.0g蓝绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(g)。
合成实施例8
酞菁化合物(h)的合成
将3.0g二羟基硅四〔2,2’-双(三甲基氟甲基)丙氧基〕酞菁溶解在100mlN-甲基吡咯烷酮中,加入2.0g3-(4-二乙基氨基苯基偶氮)苯磺酸,将混合物在80℃下加热搅拌2小时。将反应混合物倒入2.0l冰水中,过滤回收沉淀的晶体,用水洗并干燥,获得暗绿色粉末。将粉末溶解在200ml氯仿中,过滤除去不溶物,蒸馏除去滤液中的溶剂,获得1.6g暗绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(h)。
合成实施例9
酞菁化合物(i)的合成
将3.0g二苯基膦氧基(phosphinoyloxy)羟基硅四(2,5-二甲基-3-戊氧基)酞菁溶解在100ml环丁砜中,加入1.0g3-(2-羟基萘基偶氮)苯,将混合物在80℃下加热搅拌2小时。将反应混合物倒入2.0l冰水中,过滤回收沉淀的晶体,用水洗并干燥,获得暗绿色粉末。将粉末溶解在200ml氯仿中,过滤除去不溶物,蒸馏除去滤液中的溶剂,获得1.8g暗绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(i)。
合成实施例10
酞菁化合物(j)的合成
将3.2g二苯基膦氧基铝八氯-四〔2,2’-双(三氟甲基)丙氧基〕酞菁溶解在100mlN-甲基吡咯烷酮中,加入1.5g二茂铁磺酸,将混合物在25℃下搅拌2小时。将反应混合物倒入200ml冰水中,过滤回收所得的沉淀物,用水洗,获得绿色糊料。将糊料溶解在400ml丙酮中,过滤除去不溶物。然后,在滤液中滴加200ml辛烷,搅拌混合物3小时。过滤回收所得的沉淀物,用辛烷洗涤并干燥,获得0.9g绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(j)。测量该粉末溶于乙基溶纤剂溶液的电子吸收谱,表明原料二苯基膦氧基铝八氯-四〔2,2’-双(三氟甲基)丙氧基〕酞菁的最大吸收峰向较长波长的方向位移约10nm。由此发现,作为试剂的二茂铁磺酸和作为原料的酞菁的中心金属Al通过离子键相互作用。
合成实施例11
酞菁化合物(k)的合成
将2.8g羟基铝四(2,2,3,3-四氟丙氧基)酞菁溶解在100mlN-甲基吡咯烷酮中,加入3.0g二茂铁磺酸,将混合物在80℃下搅拌2小时。将反应混合物倒入200ml冰水中,过滤回收所得的沉淀物,用水洗,获得绿色糊料。将糊料溶解在400ml丙酮中,过滤除去不溶物。然后,滴加200ml辛烷,搅拌混合物3小时。过滤回收所得的沉淀物,用辛烷洗涤并干燥,获得1.3g绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(k)。
合成实施例12
酞菁化合物(l)的合成
将3.0g二羟基锗四溴-四叔丁基酞菁加入含100ml二甲苯和0.5g吡啶的溶液中,加入1.5g蒽醌-β-磺酰氯,在加热下使混合物回流3小时。冷却反应混合物,倒至300ml辛烷中,过滤回收所得的沉淀物,将之溶解在50ml丙酮中。过滤除去不溶物,加入50ml辛烷,形成绿色沉淀。过滤回收沉淀物,用辛烷洗涤并干燥,获得0.7g绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(l)。
合成实施例13
酞菁化合物(m)的合成
将3.0g羟基镓四(叔丁基)苯硫基酞菁和3.0g如下式结构的镍配位化合物磺酸化合物溶解在100mlN-甲基吡咯烷酮中,在90℃下加热搅拌混合物3小时。冷却反应混合物,倒至200ml乙醇中,过滤回收所得的沉淀物,用乙醇洗涤并干燥,获得3.1g绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(m)。
合成实施例14
酞菁化合物(n)的合成
将2.5g二苯基膦氧基铝四(新戊氧基)酞菁和1.0g丁基二茂铁磺酸加至50ml甲基溶纤剂中,在25℃时搅拌混合物4小时。过滤除去不溶物,在减压下蒸馏除去溶剂。加入50ml辛烷过滤剩余物,用100ml辛烷洗涤过滤获得的产物,干燥,获得2.8g绿色粉末。用FD-MS分析该粉末,表明它为酞菁化合物(n)。
实施例1和对比例1
将100mg酞菁化合物(a)-(n)中的一种或如下式的对比酞菁化合物(o)-(p)中的一种加至3ml乙基溶纤剂中,用超声清洁机溶解。使溶液通过0.2μ滤纸,用纺涂机在1,200rpm下,使用所得的溶液在已经减压热处理过的玻璃基材上形成染料膜。用分光光度计测量所形成的膜在最大吸收峰(λmax)处的吸收度(Abs.),将测量值取为100。然后,将在其上形成膜的玻璃基材经过耐光试验机,在50,000勒(lux)下辐照150小时,然后在λmax处作类似的吸收度测量,以测量值与初始值100之比为基准来评价膜。
酞菁化合物(o)
表1
酞菁化合物 | 耐光性试验前 | 耐光性试验后 |
(a)(b)(c)(d)(e)(f)(g)(h)(i)(j)(k)(l)(m)(n) | 100100100100100100100100100100100100100100 | 9491899395929692889790879295 |
(o)(p) | 100100 | 7481 |
表1表明,与使用对比酞菁化合物(o)和(p)的情况相比,式(1)酞菁化合物薄膜的吸收度较之于初始值的降低是非常小的,所有的降低范围都在15%之内。因此可以看出,酞菁化合物(a)-(n)的轴向取代基对改进耐光性是非常有效的。
实施例2
制备酞菁化合物(a)-(n)中一种的5%(重量)乙基溶纤剂溶液,用纺涂机在聚碳酸酯基材上形成厚为500埃的膜,所述基材含有深度为1,600埃,宽度为0.4μm和间距为1.6μm的导槽,并且其厚度为1.2mm,外径为200mm以及内径为30mm。然后,作为反射膜,所用的是将金喷溅在上述染料膜上形成的厚为800埃的膜。另外,用可紫外线固化的膜在其上形成保护膜,制得一CD-R盘。以1.2mm/sec的线速用半导体激光在该介质上记录EFM信号。所记录信号的特征按桔皮书评价。
然后,上述光盘在耐光试验机中在50,000勒下经150小时后取出。按上述相同的方式进行记录和评价所记录的信号特征。表2列出结果。
评价记录信号的特征是最佳记录功率(PO,最佳记录功率),槽列的最大反射值(Rtop,折射顶点),槽列中所发生的错误率(BLER,块错误率)和在最长槽列中反射的最大值和最小值之间的距离(LLT调节因子,IIT调节)。
表2表明使用酞菁化合物(a)-(n)作为光记录介质(CD-R)具有稳定的记录特征,如优异的记录灵敏度,小的错误率和高的调节度,尤其是,未进行耐光试验的介质和进行试验的介质之间在记录特征上并无大的差别,介质可以完全适应快速存取存储并具有高的可靠性。
表2
酞菁化合物 | POmw | Rtop% | BLERMax/10sec | IIT调节度 | |
(a)(a) | 初始 | 6.4 | 72 | 5> | 54 |
Alrt* | 68 | 12 | 51 | ||
(b)(b) | 初始 | 5.8 | 68 | 5> | 62 |
Alrt* | 64 | 14 | 58 | ||
(c)(c) | 初始 | 5.5 | 67 | 5> | 65 |
Alrt* | 66 | 10 | 61 | ||
(d)(d) | 初始 | 5.3 | 66 | 5> | 53 |
Alrt* | 62 | 21 | 50 | ||
(e)(e) | 初始 | 5.6 | 69 | 5> | 62 |
Alrt* | 69 | 5> | 59 | ||
(f)(f) | 初始 | 6.0 | 72 | 5> | 64 |
Alrt* | 72 | 5> | 63 | ||
(g)(g) | 初始 | 5.5 | 70 | 5> | 65 |
Alrt* | 70 | 5> | 63 | ||
(h)(h) | 初始 | 6.4 | 63 | 5> | 54 |
Alrt* | 58 | 17 | 50 | ||
(i)(i) | 初始 | 6.8 | 61 | 5> | 62 |
Alrt* | 57 | 14 | 58 | ||
(j)(j) | 初始 | 5.5 | 65 | 5> | 60 |
Alrt* | 63 | 8 | 60 | ||
(k)(k) | 初始 | 5.3 | 56 | 5> | 53 |
Alrt* | 55 | 18 | 50 | ||
(l)(l) | 初始 | 5.6 | 54 | 5> | 57 |
Alrt* | 51 | 26 | 55 | ||
(m)(m) | 初始 | 5.1 | 49 | 5> | 72 |
Alrt* | 49 | 28 | 68 | ||
(n)(n) | 初始 | 5.5 | 69 | 5> | 65 |
Alrt* | 67 | 5> | 62 |
Alrt*=耐光试验后
实施例3和对比例2
制备150mg酞菁化合物(j)溶于3ml乙基溶纤剂的溶液,用纺涂机在聚碳酸酯基材上形成厚为800埃的膜,所述基材含有深度为1,800埃,宽度为0.4μm和间距为1.6μm的导槽,其厚度为1.2 mm,外径为200mm内径为30mm。然后,作为反射膜,所用的是将金喷溅在染料膜上形成的厚为800埃的膜。另外,用可紫外线固化的膜在其上形成保护膜,制得一CD-R盘。以1.2mm/sec的线速用半导体激光在该介质上记录EFM信号。所记录信号的特征按桔皮书评价。
然后,将上述光盘在耐光试验机中在50,000勒下经过100小时后取出。按上述相同的方式进行记录和评价所记录信号的特征。表3列出了结果。
作为对比,以上述相同的方法使用如下式的酞菁化合物(q)的5%溶液制成CD-R盘。并按上述相同的方法评价记录的特征,并进行耐光试验。表3列出结果。
酞菁化合物(q)
表3
实施例 | 组成 | POmw | Rtop% | BLERMax/10sec | IIT调节 | |
实施例3 | (j) | 初始 | 5.6 | 69 | 5> | 65 |
Alrt* | 68 | 5> | 64 | |||
对比例2 | (q) | 初始 | 6.0 | 70 | 5> | 62 |
Alrt* | 60 | 210 | 55 |
Alrt*=耐光试验后
表3表明如下事实。与酞菁化合物(q)相比,酞菁化合物(j)在调节度和错误率等的记录特征上有改进,尤其是,未进行耐光试验的介质和进行试验的介质之间酞菁化合物(j)几乎没有差别。相反,耐光试验后,对酞菁化合物(q),则Rtop下降,调节度下降和错误率升高。从而看出含磺酸基的特定轴向取代基的效应,使酞菁化合物(j)在记录特征上显示出优于酞菁化合物(q)的改进并具有改进的耐光性。
工业应用
由于记录层含有带磺酸基的特定轴向取代基的酞菁化合物,可以获得记录灵敏度和记录特征都完全适应快速存取存储并具有优异耐光性的光记录介质。
Claims (4)
其中各X1-X4独立地为氢原子,烷基,取代的烷基,芳基,取代的芳基,脂环残基,取代的脂环残基,芳烷基,取代的芳烷基,杂环,取代的杂环,烷氧基,取代的烷氧基,芳氧基,取代的芳氧基,烷基硫代基或取代的芳基硫代基,
各Y1-Y4独立地为氢原子,卤原子,硝基,邻苯二甲酰亚胺甲基,取代的邻苯二甲酰亚胺甲基,砜酰胺基或取代的砜酰胺基,
各R1和R2独立地为氢原子,卤原子,羟基,烷基,取代的烷基,芳基,取代的芳基,芳烷基,取代的芳烷基,烷氧基,取代的烷氧基,芳氧基,取代的芳氧基,烷基硫代基,取代的烷基硫代基,芳基硫代基,取代的芳基硫代基,烷基氨基,取代的烷基氨基,二烷基氨基,取代的二烷基氨基,芳基氨基,取代的芳基氨基,二芳基氨基或取代的二芳基氨基,
M为Al,Ga,In,Si,Ge或Sn,
Z为下式(2)-(6)之一的偶氮化合物,蒽醌化合物或金属配位化合物,
n1-n4为取代基X1-X4的数目,它们分别独立地为1-4的整数,
m1-m4为取代基Y1-Y4的数目,它们分别独立地为0-4的整数,
k为轴向取代基-OSO2-Z的数目,它为1或2,和
1为轴向取代基-OP(=O)R1R2的数目,它为0或1,但k+l为1或2。
式(2),
其中各R3,R4和R5独立地为氢原子,卤原子,羟基,硝基,氰基,羧酸基,羧酸酯基,磺酸基,磺酸酯基,烷基,取代的烷基,芳基,取代的芳基,环烷基,取代的环烷基,芳烷基,取代的芳烷基,杂环,取代的杂环,烷氧基,取代的烷氧基,芳氧基,取代的芳氧基,烷基硫代基,取代的烷基硫代基,芳基硫代基,取代的芳基硫代基,氨基,烷基氨基,取代的烷基氨基,二烷基氨基,取代的二烷基氨基,芳基氨基或取代的芳基氨基,
n5为取代基R3的数目,它为0-4的整数,n6和n7为取代基R4和R5的数目,它们分别为0-5的整数,
其中R3-R6与式(2)中R3-R5的含义相同,n5为取代基R3的数目,它为0-4的整数,n6-n8为取代基R4-R6的数目,它们分别为0-3的整数,
其中R3-R6与式(2)中R3-R5的含义相同,n5-n8为取代基R3-R6的数目它们分别为0-3的整数,
式(5),
其中A1和A2为苯环或萘环,R3-R6与式(2)中R3-R5的含义相同,n5-n8为取代基R3-R6的数目,它们分别为0-3的整数,M1为过渡金属原子,和
其中R3和R4与式(2)中R3-R5的含义相同,n5为取代基R3的数目,它为0-4的整数,n6为取代基R4的数目,它为0-5的整数,M2为过渡金属。
2.如权利要求1所述的光记录材料,其特征在于,式(1)中k和l分别为1。
3.如权利要求1所述的光记录材料,其特征在于,式(1)中l为0。
4.一种光记录介质,它包含一透明基材,一记录层,一反射层和一保护层共四层,所述记录层包含如权利要求1所述的光记录材料。
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EP (1) | EP0811506B1 (zh) |
JP (1) | JP3377531B2 (zh) |
KR (1) | KR100288681B1 (zh) |
CN (1) | CN1070783C (zh) |
AU (1) | AU1172797A (zh) |
DE (1) | DE69612189T2 (zh) |
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WO2003030158A2 (en) * | 2001-10-04 | 2003-04-10 | Bayer Chemicals Ag | Optical data medium containing; in the information layer, a dye as a light-absorbing compound |
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DE10253610A1 (de) * | 2002-11-15 | 2004-05-27 | Bayer Ag | Optische Datenspeicher enthaltend ein Co-Phthalocyanin mit einem axialen Substituenten und einem axialen Liganden in der mit Licht beschreibbaren Informationsschicht |
WO2004053874A1 (en) | 2002-12-11 | 2004-06-24 | Lg Electronics Inc. | Method of managing overwrite and method of recording management information on an optical disc write once |
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-
1996
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- 1996-12-24 WO PCT/JP1996/003753 patent/WO1997023354A1/ja active IP Right Grant
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- 1996-12-24 CN CN96191531A patent/CN1070783C/zh not_active Expired - Fee Related
- 1996-12-24 AU AU11727/97A patent/AU1172797A/en not_active Abandoned
- 1996-12-24 EP EP96942619A patent/EP0811506B1/en not_active Expired - Lifetime
- 1996-12-24 DE DE69612189T patent/DE69612189T2/de not_active Expired - Fee Related
- 1996-12-24 US US08/860,593 patent/US5820962A/en not_active Expired - Fee Related
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CN1304486C (zh) * | 2002-02-15 | 2007-03-14 | 三井化学株式会社 | 酞菁化合物,制备该酞菁化合物的方法以及含有该酞菁化合物的光记录介质 |
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Publication number | Publication date |
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EP0811506A4 (en) | 1998-04-01 |
KR100288681B1 (ko) | 2001-05-02 |
TW334528B (en) | 1998-06-21 |
JP3377531B2 (ja) | 2003-02-17 |
EP0811506B1 (en) | 2001-03-21 |
WO1997023354A1 (fr) | 1997-07-03 |
DE69612189T2 (de) | 2001-07-19 |
KR19980702259A (ko) | 1998-07-15 |
EP0811506A1 (en) | 1997-12-10 |
US5820962A (en) | 1998-10-13 |
AU1172797A (en) | 1997-07-17 |
CN1070783C (zh) | 2001-09-12 |
DE69612189D1 (de) | 2001-04-26 |
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