CN101073116A - 光学数据记录用光学层中使用的吡啶n－氧化物系偶氮染料及其金属络合物 - Google Patents
光学数据记录用光学层中使用的吡啶n－氧化物系偶氮染料及其金属络合物 Download PDFInfo
- Publication number
- CN101073116A CN101073116A CNA2005800406368A CN200580040636A CN101073116A CN 101073116 A CN101073116 A CN 101073116A CN A2005800406368 A CNA2005800406368 A CN A2005800406368A CN 200580040636 A CN200580040636 A CN 200580040636A CN 101073116 A CN101073116 A CN 101073116A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- replace
- aryl
- hydrogen
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 86
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 title abstract description 18
- 239000000987 azo dye Substances 0.000 title abstract description 17
- 229910052751 metal Inorganic materials 0.000 title abstract description 8
- 239000002184 metal Substances 0.000 title abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 64
- 150000002431 hydrogen Chemical class 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 22
- 239000010949 copper Substances 0.000 claims description 21
- -1 Sulfuryl Chemical group 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052802 copper Inorganic materials 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 239000011701 zinc Substances 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 8
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 239000011669 selenium Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- KUGBQWBWWNPMIT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoropentan-1-ol Chemical compound CC(F)(F)C(F)(F)C(F)(F)C(O)(F)F KUGBQWBWWNPMIT-UHFFFAOYSA-N 0.000 claims description 4
- BNDRWEVUODOUDW-UHFFFAOYSA-N 3-Hydroxy-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)O BNDRWEVUODOUDW-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910004013 NO 2 Inorganic materials 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- YIHRGKXNJGKSOT-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorobutan-1-ol Chemical class CC(F)(F)C(F)(F)C(O)(F)F YIHRGKXNJGKSOT-UHFFFAOYSA-N 0.000 claims description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 claims description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- 229940113088 dimethylacetamide Drugs 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 abstract description 13
- 230000005855 radiation Effects 0.000 abstract description 8
- 239000000975 dye Substances 0.000 description 69
- 150000001875 compounds Chemical class 0.000 description 25
- 238000000354 decomposition reaction Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 239000003381 stabilizer Substances 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 10
- 238000004528 spin coating Methods 0.000 description 10
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004040 coloring Methods 0.000 description 7
- 239000012954 diazonium Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000011651 chromium Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 241000931526 Acer campestre Species 0.000 description 3
- KXXGXRWKXNWOIM-UHFFFAOYSA-N Cl.CCOC1=CC=C[N+]([O-])=C1N Chemical compound Cl.CCOC1=CC=C[N+]([O-])=C1N KXXGXRWKXNWOIM-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 238000010422 painting Methods 0.000 description 3
- 238000002310 reflectometry Methods 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 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 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- NLMHBICZOKERBX-UHFFFAOYSA-N 2-(1-ethyl-6-hydroxypyridin-2-ylidene)propanedinitrile Chemical compound CCN1C(O)=CC=CC1=C(C#N)C#N NLMHBICZOKERBX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003989 dielectric material Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- ZXKXJHAOUFHNAS-FVGYRXGTSA-N (S)-fenfluramine hydrochloride Chemical compound [Cl-].CC[NH2+][C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 ZXKXJHAOUFHNAS-FVGYRXGTSA-N 0.000 description 1
- CSUFEOXMCRPQBB-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropan-1-ol Chemical compound CC(F)(F)C(O)(F)F CSUFEOXMCRPQBB-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- ZTWMBHJPUJJJME-UHFFFAOYSA-N 3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)NC1=O ZTWMBHJPUJJJME-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- KDPMIBMNNGCWTF-UHFFFAOYSA-N C(CCC)O.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical class C(CCC)O.CC1(CC(C(=O)O)=CC=C1)C(=O)O KDPMIBMNNGCWTF-UHFFFAOYSA-N 0.000 description 1
- FXXMNCZOYVUJEE-UHFFFAOYSA-N C1(=CC=CC=C1)N1N=CCC1=O.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical compound C1(=CC=CC=C1)N1N=CCC1=O.CC1(CC(C(=O)O)=CC=C1)C(=O)O FXXMNCZOYVUJEE-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- OYWWKXHGXSQJGW-UHFFFAOYSA-N Cl.CCOC1=CC(Br)=C[N+]([O-])=C1N Chemical compound Cl.CCOC1=CC(Br)=C[N+]([O-])=C1N OYWWKXHGXSQJGW-UHFFFAOYSA-N 0.000 description 1
- GZENQWSEJOBOAF-UHFFFAOYSA-N Cl.NC1=CC=CC=[N+]1[O-] Chemical compound Cl.NC1=CC=CC=[N+]1[O-] GZENQWSEJOBOAF-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229920013685 Estron Polymers 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- FUSUXVPRJOJIGI-UHFFFAOYSA-N NC1=CC=C(Br)C=[N+]1[O-] Chemical compound NC1=CC=C(Br)C=[N+]1[O-] FUSUXVPRJOJIGI-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- QFKZKLVFOGGPJK-UHFFFAOYSA-N ON1NC=CC(=N1)C1=CC=CC=C1 Chemical compound ON1NC=CC(=N1)C1=CC=CC=C1 QFKZKLVFOGGPJK-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical class OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000000680 avirulence Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- CMKIPUDSZBGVQI-UHFFFAOYSA-N chembl2147998 Chemical compound OC1=CC=CC=C1C1=CNN=N1 CMKIPUDSZBGVQI-UHFFFAOYSA-N 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001870 copolymer plastic Polymers 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 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 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 150000005837 radical ions Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/34—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/2467—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes azo-dyes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
- G11B7/2492—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds neutral compounds
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B2007/24612—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes two or more dyes in one layer
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/257—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
- G11B2007/25705—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
- G11B2007/25708—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing group 13 elements (B, Al, Ga)
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/257—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
- G11B2007/25705—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
- G11B2007/2571—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing group 14 elements except carbon (Si, Ge, Sn, Pb)
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/257—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
- G11B2007/25705—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
- G11B2007/25713—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing nitrogen
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/257—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
- G11B2007/25705—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
- G11B2007/25715—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing oxygen
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/257—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
- G11B2007/25705—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials
- G11B2007/25716—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of inorganic materials containing sulfur
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2531—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising glass
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2534—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polycarbonates [PC]
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
- G11B7/2535—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins polyesters, e.g. PET, PETG or PEN
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/254—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers
- G11B7/2542—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of protective topcoat layers consisting essentially of organic resins
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/257—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers
- G11B7/2572—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of organic materials
- G11B7/2575—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of layers having properties involved in recording or reproduction, e.g. optical interference layers or sensitising layers or dielectric layers, which are protecting the recording layers consisting essentially of organic materials resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
本发明涉及吡啶N－氧化物系偶氮染料及其金属络合物在光学数据记录用光学层中的用途。较好用于采用波长可高达450nm的蓝色激光或波长可高达650nm的红色激光的光学数据记录。本发明进一步涉及一种能以蓝色或红色激光的辐射记录和再现信息之一次写入多次读出(WORM)型光学记录媒体，该媒体在光学层内使用吡啶N－氧化物系偶氮染料或其各自的金属络合物。
Description
本发明涉及吡啶N-氧化物系偶氮染料及其金属络合物在光学数据记录用光学层中的用途，较佳用于用波长可高达450nm蓝色激光及波长可高达650nm的红色激光的光学数据记录。
本发明进一步涉及一种能用蓝色或红色激光的辐射记录和再现信息之一次写入多次读出(WORM)型光学记录媒体，该媒体在光学层中使用吡啶N-氧化物系偶氮染料或其各自的金属络合物。
近来，有机染料在二极管激光光学存储领域备受瞩目。市售可记录紧密光碟(CD-R)与可记录数码通用光碟(DVD-R)可含有以酞菁、半花青、花青及金属化偶氮结构为基础的多种杂料作为记录层。这些染料依照激光波长基准适用于其各自领域。其它对染料媒体的总体要求为强吸收、高反射度、高记录灵敏性、低热导率以及光与热稳定性，耐存储或无毒性。
对于工业应用，这些染料必须适用于制备薄膜的旋涂方法，即其必须充分溶解于一般应用于旋涂方法中的有机溶剂中。
WORM(一次写入多次读出)型与可擦型光学记录媒体藉由检测记录层记录前后的物理变形，光学特征变化以及相与磁性质的变化而引起的反射率变化来重现信息。
可记录紧密光碟(CD-R)作为一种WORM型光学记录媒体普遍已知。最近，信息存储能力增加至4.7G字节之数码通用光碟(DVD-R)已经商业化。
DVD-R技术采用波长为630-670nm之红色二极管激光作为光源。因此记录纹宽及轨间距可减小，从而其信息存储能力比CD-R提高多达6-8倍。
Blu-ray光碟(Blu-ray光碟系由日立公司，LG电子公司，松下电器工业公司，先锋公司，皇家菲利浦电子公司，三星电子公司，夏普公司，索尼公司，Thomson Multimedia发展的一种标准)将成为光学记录技术的下一个里程碑。其新规格将直径12cm光碟的每个记录层的数据存储量提高至27G字节。藉由采用波长405nm的蓝色二极管激光(GaN或SHG激光二极管)，记录纹宽及轨间距可进一步减小，从而再次将存储能力提高一个数量级。
光学数据记录媒体的构造是业内已知的。光学数据记录媒体一般包含基板与记录层即光学层。通常使用有机聚合材料光碟或波盘(wavers)作为基板。较佳基板为聚碳酸酯(PC)或聚甲基丙烯酸甲酯(PMMA)。基板必须提供具有高光学品质之平坦且均匀的表面。光学层以具有高光学品质与界定厚度之均匀薄膜的形式沉积于基板上。最后，反射层(如铝、金或铜)沉积于光学层上。
高级光学数据记录媒体可包含进一步的层，如保护层、粘合剂层或额外光学层。
为提供光学层之均匀薄膜，通常藉由旋涂法、真空蒸发法、喷涂法、滚涂法或浸渍法来沉积材料。在工业中，较佳方法为形成厚度大约70nm至250nm的光学层的旋涂法。为了在旋涂法中的应用，光学层材料必须在有机溶剂中高度可溶。
吡啶N-氧化物系偶氮染料已知多年。例如，已有人公开如下结构之染料对乙酸纤维素纤维具有很好的亲合力(US 3,249,597)。
这样的吡啶N-氧化物系偶氮染料也已经有人公开用于染发组合物(例如参见US 3,955,918)。
金属络合物，尤其吡啶N-氧化物系偶氮化合物的铜(II)、镍(II)、钴(II)、铁(III)及锰(II)络合物在以下出版物中得到描述：a)Renko，D.；Koprivanac，N.；Jovanovic-Kolar，J.；Osterman，D.Kemija uIndustriji(1979)，28(2)，53-58.；b)Koprivanac，N；Jovanovic-Kolar，J.；Kramer，V.International Journal of Mass Spectrometry与Ion Physics(1983)47，531-534。这样的金属络合物的生成用于铁、铜、钪及锆的分光光度测定。关于铁与铜，参见：Beaupre，P.W.；Holland，W.J.Mikrochimica Acta(1983)3(1-2)71-75。关于钪，参见：Beaupre，P.W.；Holland，W.J.Mikrochimica Acta(1982)2(5-6)419-422。关于锆，参见：Beaupre，P.W.；Holland，W.J.Mikrochimica Acta(1980)2(1-2)53-57。
现已令人惊奇地发现，如下所述之特定吡啶N-氧化物系偶氮染料及其金属络合物可用来作为光学数据记录媒体用光学层中的染料化合物。
因此本发明涉及吡啶N-氧化物系偶氮染料及其金属络合物在以下所述光学层中的用途，且涉及该光学层用于光学数据记录媒体的用途。
更具体地说，本发明涉及一种能用较佳405-410nm的蓝色激光的辐射或用较佳635-640nm的红色激光的辐射记录与重现信息的一次写入多次读出(WORM)型光学数据记录媒体，该媒体在光学层中使用吡啶N-氧化物系偶氮染料或其各自的金属络合物。
本发明涉及式(I)或(II)的染料化合物在光学数据记录媒体用光学层中的用途：
其中
R1至R4彼此独立地表示氢、氰基(-CN)、卤素(F、Cl、Br、I)、硝基(NO2)、羟基(-OH)；
C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烯基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立为氢、C1-8烷基或C6-12芳基；
C1-8烷氧基(-OR)，其中烷基(R)可以是无取代或有C1-8烷基、C1-8烯基、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基、C1-8烯基或C6-12芳基；
-CX3，其中X可为氯、氟、溴；
-NR5R6，其中R5与R6独立地为氢、C1-8烷基、C1-8烯基或C6-12芳基；
C1-8烷硫基(-SR)，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8亚砜基(-S(O)R)，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8砜基(-SO2R)，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-2芳基；
C1-8氨磺酰(-SO2NR5R6)，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8碳酰胺基(-CO2NR5R6)，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8磷酰胺基(-P(O)(NR5R6)2)，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8磷酸酯基(-P(O)(OR)2)，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
X1表示氧、硫、硒，
-NR，其中R表示氢、氰基、C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-NSO2R，其中R表示C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基，C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-NP(O)(OR)2，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
B表示无取代或有取代的芳香族环；或
以下结构的五员或六员杂环：
其中
R7至R9彼此独立表示氢、卤素、氰基，
C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-SO2R，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-2芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
X2至X3表示氧、硫、硒，
-NR，其中R表示氢、氰基、C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基，卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-NSO2R，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-NP(O)(OR)2，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基，卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
X4表示表示氧、硫、硒，
＝NR，其中R表示氢、氰基、C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；或＝C(CN)2；
M表示金属原子，包括Al、In、Sn、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Zr、Ru、Rh、Pd、Cd、Hf、Re、Os、Ir、Pt、Hg。
在一个较佳方面，本发明涉及式(II)的染料化合物，其中式(II)的染料化合物有更特定的式(III)：
M选自Ni、Cu、Co、Zn、Al、Fe、Ru、Pd、Pt、Cr、Mn组成的一组；
R1选自H、Cl、CH3、C2H5、C3H7或无取代苯基，
R2选自H、Br、Cl、F、NR2，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR7R8取代，其中R7与R8独立地为氢、C1-8烷基或C6-12芳基；NO2、CH3、C2H5，
R3选自H、Cl、CH3、C2H5，
R4是氢、CH3、C2H5、OR，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR7R8取代，其中R7与R8独立地为氢、C1-8烷基或C6-12芳基；
R7至R8彼此独立地表示氢、C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
X2至X3选自O、S、NR，其中R表示氢、氰基、C1-8烷基。
在一个更佳方面，本发明涉及式(III)的染料化合物，其中
M选自Ni、Cu、Co、Zn、Al、Fe、Cr、Mn组成的一组；
R1选自H、CH3，
R2选自H、Br、Cl、NO2、CH3，
R3是氢，
R4选自H、Cl、CH3、OC2H5、OH，
R7到R8彼此独立地选自CH3、C2H5、C3H7(正丙基或异丙基)、C4H9(正丁基，仲丁基或叔丁基)，
X2选自O、S，
X3是O。
在一种最佳实施方案中，本发明涉及式(III)的染料化合物，其中M选自镍、铜或锌、R1是H，R2是Br，R3是氢，R4是OC2H5，R7与R8是C2H5，且X2是S，X3是O。
本发明进一步涉及一种光学层，包含如上所述的式(I)或(II)的染料化合物，并涉及所述光学层用于光学数据记录媒体的用途。按照本发明的光学层也可以包含两种或更多种(较佳两种)如上界定的式(I)和/或(II)的染料化合物的混合物。
式(I)或(II)的吡啶N-氧化物系偶氮染料化合物当用于按照本发明的光学数据记录媒体用光学层中时提供特别好的性能。
此外，本发明涉及一种光学层制造方法，包含以下步骤：
(a)提供基板，
(b)将式(I)或(II)的染料化合物或染料化合物的混合物溶解于有机溶剂中以形成溶液，
(c)将溶液(b)涂覆于基板(a)上，
(d)蒸发溶剂以形成染料层。
较佳基板为聚碳酸酯(PC)或聚甲基丙烯酸甲酯(PMMA)。
有机溶剂选自C1-8醇、有卤素取代的C1-8醇、C1-8酮、C1-8醚、有卤素取代的C1-4烷烃、或酰胺。
较佳的C1-8醇或有卤素取代的C1-8醇是例如甲醇、乙醇、异丙醇、双丙酮醇(DAA)、2，2，3，3-四氟丙醇、三氯乙醇、2-氯乙醇、八氟戊醇或六氟丁醇。
较佳C1-8酮是例如丙酮、甲基异丁基酮、甲基乙基酮，或3-羟基-3甲基-2-丁酮。
较佳有卤素取代的C1-4烷烃是例如氯仿、二氯甲烷或1-氯丁烷。
较佳酰胺是例如二甲基甲酰胺或二甲基乙酰胺。
所得之光学层(染料层)厚度较佳为70至250nm。
在一个较佳方面，本发明提供一种适合于例如WORM光碟格式的高密度记录材料用光学层，所用激光波长在350-450nm范围内，较好在405nm左右。本发明也提供一种适合于例如WORM光碟格式的高密度记录材料用光学层，所用激光波长在630-650nm范围内，较好在635nm左右。该光学层对于蓝色激光应用较佳。
式(I)与(II)的染料化合物具有所需要的光学特征(例如高吸收性，高记录灵敏性)，在有机溶剂中优异的溶解性，优异的光稳定性及250-350℃的分解温度。
单偶氮染料(I)的制备
偶合反应可以在水性或非水性溶剂中进行。非水性溶剂是醇类如甲醇、乙醇、丙醇、丁醇、戊醇等，偶极无质子溶剂如DMF、DMSO、NMP及和水不混溶溶剂如甲苯或氯苯。
偶合较好以偶合组分与重氮组分的化学计量比进行。偶合通常在-30℃至100℃之间的温度进行，较好温度为-10℃至30℃，且特别好温度为-5℃至10℃。
偶合可在酸性及碱性介质中进行。pH＜10较佳，pH＜7.0尤佳，pH＜5.0甚佳。
金属络合物(II)的制备
络合物较佳藉由一当量金属盐溶液与两当量相应染料在选自以下所列极性溶剂中的沸腾溶液反应来制备。沉淀物按照标准方法分离。
该过程中使用的溶剂较佳选自C1-8醇、烷基腈、芳香族烃、二甲基甲酰胺、N-二甲基吡咯烷酮或这些溶剂之一与水的混合物或水本身组成的一组。该过程中使用之最佳溶剂为C1-8醇。
光学层的制备
按照本发明的光学层包含式(I)或(II)的吡啶N-氧化物偶氮系染料或式(I)和/或(II)的金属络合物的混合物。
按照本发明的光学层的制造方法包含以下步骤：
(a)提供基板，
(b)将染料化合物(I)或(II)或式(I)和/或(II)的染料化合物的混合物溶解于有机溶剂中形成溶液，
(c)将溶液(b)涂覆于基板(a)上，
(d)蒸发溶剂以形成染料层。
高密度光学记录媒体的制备
包含按照本发明的光学层的光学记录媒体的制造方法还包含以下步骤：
(e)将金属层喷镀到该染料层上，
(f)施加第二个聚合物系层以完成光碟。
因此按照本发明的高密度数据存储媒体较佳为可记录光碟，包含：第一基板，即一种有槽纹的透明基板；记录层(光学层)，是采用式(I)或(II)的染料化合物在第一基板表面上形成的；形成于该记录层上的反射层；第二基板，即一种有槽纹并经附着层连接至反射层的透明基板。
固体膜状的式(I)或(II)的染料化合物在吸收谱带的较长波长区具有高折射率，它较佳在蓝色激光用途的350至500nm范围内或在红色激光用途的500-630nm范围内达到2.0至3.0之峰值。式(I)或(II)的染料化合物可以提供在所希望的光谱范围内有高反射率以及高灵敏性和良好重放特征的媒体。
(a)基板
基板(充当施加于其上之各层的载体)有利为半透明(T＞10％)的或较佳为透明(T＞90％)的。该载体可以有0.01至10mm较好0.1至5mm的厚度。适用的基板是例如玻璃、矿物质、陶瓷及热固性或热塑性塑料。较佳的载体是玻璃及均聚物或共聚物塑料。适用的塑料是例如热塑性聚碳酸酯、聚酰胺、聚酯、聚丙烯酸酯及聚甲基丙烯酸酯、聚氨酯、聚烯烃、聚氯乙烯、聚偏二氟乙烯、聚酰亚胺、热固性聚酯及环氧树脂。
最佳的基板是聚碳酸酯(PC)或聚甲基丙烯酸甲酯(PMMA)。
基板可以呈纯粹形式，也可以包含惯常添加剂，例如UV吸收剂或染料(如JP 04/167239所提出的)作为记录层的光稳定剂。在后一种情况下，对于加入该载体基板中的染料可能有利的是其吸收最大值相对于记录层的染料而言蓝移至少10nm，较佳至少20nm。
该基板有利地在350至700nm范围内至少一部分是透明的，使得它可透过写入或读出波长的入射光的至少90％。
(b)有机溶剂
有机溶剂选自C1-8醇、有卤素取代的C1-8醇、C1-8酮、C1-8醚、有卤素取代的C1-4烷烃或酰胺。
较佳的C1-8醇或有卤素取代的C1-8醇是例如甲醇、乙醇、异丙醇、双丙酮醇(DAA)、2，2，3，3-四氟丙醇、三氯乙醇、2-氯乙醇、八氟戊醇或六氟丁醇。
较佳的C1-8酮是例如丙酮、甲基异丁基酮、甲基乙基酮、或3-羟基-3-甲基-2-丁酮。
较佳的有卤素取代的C1-4烷烃是例如氯仿、二氯甲烷或1-氯丁烷。
较佳的酰胺是例如二甲基甲酰胺或二甲基乙酰胺。
(c)记录层
记录层(光学层)较佳配置于透明基板与反射层之间。记录层的厚度为10至1000nm，较好30至300nm，尤其为80nm，例如60至120nm。
式(I)或(II)的染料化合物的使用有利地导致有高折射率的均匀、无定形且低散射的记录层。吸收边沿甚至在固相中也令人惊讶地陡峭。进一步的优点是在日光中及低功率密度激光辐射下的高光稳定性，且同时具有在高能量密度激光辐射下的高灵敏性、均匀的指令码宽度、高对比度、以及良好的热稳定性和存储稳定性。
按照本发明，不包含式(I)或(II)的单一化合物的记录层也可以包含这样的化合物的混合物。藉由使用混合物，例如异构体或同系物的混合物以及不同结构的混合物，通常可以增加溶解度和/或可以提高非晶态含量。
当希望时也可以添加惯常量的已知稳定剂以进一步增加稳定性，例如添加作为光稳定剂的二硫酚镍(如JP 04/025493中所述)。
记录层较佳包含充足量的式(I)或(II)的化合物或这些化合物的混合物以对折射率产生实质性影响，该数量例如为至少30重量％，更佳至少60％重量，最佳至少80重量％。
进一步的惯常组分例如其它发色团(例如WO-01/75873中揭示的发色团，或其它在300至1000nm有吸收最大值的发色团)、稳定剂、102-猝灭剂、三重态猝灭剂或发光猝灭剂、熔点降低剂、分解加速剂或任何其它已描述的光学记录媒体中的添加剂。较佳若希望时可加入稳定剂或萤光猝灭剂。
当记录层包含进一步的发色团时，它们原则上可以是任何可以在记录期间因激光辐射而分解或改性的染料，或者它们可以是对激光辐射惰性的。当进一步的发色团因激光辐射而分解或改性时，这可能通过激光辐射的吸收而直接发生或间接地由按照本发明的式(I)或(II)的化合物的分解(例如热分解)而诱发。
当然进一步的发色团或着色稳定剂可能影响记录层之光学性质。因此较好使用光学性质尽可能与式(I)或(II)的化合物的光学性质相一致或尽可能与之不同的进一步发色团或着色稳定剂，或保持进一步发色团的小用量。
当使用具有尽可能与式(I)或(II)的化合物相一致之光学性质的进一步发色团时，较好这应当是在最长波长吸收区范围内的情况。进一步发色团及式(I)或(II)的化合物的转化点的波长较好相距最大20nm，尤其相距最大10nm。在这种情况下，进一步发色团与式(I)或(II)的化合物对于激光辐射应当显示出类似行为，因而可以使用其作用受到式(I)或(II)的化合物协同增强的已知记录剂作为进一步的发色团。
当使用具有尽可能与式(I)或(II)的化合物不同的光学性质的进一步发色团或着色稳定剂时，有利地具有相对于式(I)或(II)的金属络合物而言蓝移或红移的吸收最大值。在这种情况下，吸收最大值相距较佳至少50nm，尤其至少100nm。
其实例是相对于式(I)或(II)的染料而言蓝移的UV吸收剂，或相对于式(I)或(II)的染料而言红移且其吸收最大值例如处于NIR或IR范围内的着色稳定剂。
也可以加入其它染料，用于色标识别、色彩掩蔽(″diamond染料″)或增加记录层美观之目的。在所有这些情况下，进一步的发色团或着色稳定剂较好都应当对光及激光辐射显示尽可能惰性的行为。
当加入另一种染料以期修饰式(I)或(II)的化合物的光学性质时，其数量取决于要达到的光学性质。业内技术人员将不难改变额外染料与式(I)或(II)的化合物的比率直至获得其所希望的结果。
当发色团或着色稳定剂用于其它目的时，其数量较好应如此小，以使得其对记录层在350至700nm范围内的总吸收的贡献最大为20％，较佳最大为10％。在这样的情况下，额外染料或稳定剂的数量有利地是以记录层为基准最多50重量％，较佳最多10重量％。
然而，最好不添加额外发色团，除非它是着色稳定剂。
稳定剂、102-猝灭剂、三重态猝灭剂或发光猝灭剂是例如含有N-或S-之烯醇盐、酚盐、双酚盐、硫醇盐或双硫醇盐之金属络合物，或偶氮、偶氮甲碱或甲
染料的金属络合物，如双(4-二甲胺基二硫代偶苯酰)镍[CASN°38465-55.3]。受阻酚及其衍生物如邻羟基苯基-三唑或邻羟基苯基-三嗪，或其它UV吸收剂如受阻胺(TEMPO或HALS，以及氮氧化物或NOR-HALS)，而且也作为阳离子的二亚铵(diimmonium)、ParaquatTM或Orthoquat盐，如Kayasorb IRG 022、Kayasorb IRG 040，任选地也作为自由基离子，如N，N，N’，N’-四(4-二丁胺基苯基)-对-亚苯基胺-铵六氟磷酸盐、六氟锑酸盐或高氯酸盐。后者可购自Organica(Wolfen/DE)公司；Kayasorb品牌可购自NipponKayaku Co.Ltd。
业内技术人员将从其它光学信息媒体得知或将容易地识别何种添加剂以何浓度最适于何种目的。适当的添加剂浓度是例如0.001至1000重量％，较佳为1至50重量％。
(d)反射层
适用于反射层的反射材料尤其包括能提供用于记录与重放的激光辐射的良好反射的金属，例如化学元素周期表第III、IV与V主族及副族的金属。Al、In、Sn、Pb、Sb、Bi、Cu、Ag、Au、Zn、Cd、Hg、Sc、Y、La、Ti、Zr、Hf、V、Nb、Ta、Cr、Mo、W、Fe、Co、Ni、Ru、Rh、Pd、Os、Ir、Pt、Ce、Pr、Nd、Pm、Sm、Eu、Gd、Tb、Dy、Ho、Er、Tm、Yb与Lu及其合金尤其适用。由于高反射率与制造简便，给予特别优选的是铝、银、铜、金或其合金之反射层。
(e)覆盖层/保护层
适于覆盖层/保护层的材料包括塑料，是以薄层形式直接或藉助粘合剂层施用于载体或最顶层的。有利的是选择机械稳定且热稳定并具有良好表面性质、可进一步改性的塑料。
该塑料可以是热固性塑料与热塑性塑料。给予优先的是辐射固化(例如采用UV辐射)的保护层，其制造特别是简易且经济。已知有种类繁多的可辐射固化材料。可辐射固化单体及低聚物的实例是二元醇、三元醇及四元醇的丙烯酸酯与甲基丙烯酸酯、芳族四羧酸与氨基的至少两个邻位上有C1-C4烷基的芳族二胺的聚酰亚胺、及带有二烷基马来酰亚胺基团例如二甲基马来酰亚胺基团的低聚物。
按照本发明的记录媒体也可以有额外层，例如干扰层。也可以构建有多个(例如两个)记录层的记录媒体。这样的材料的结构与用途是业内技术人员已知的。干扰层(若存在)较佳配置于记录层与反射层之间和/或记录层与基板之间，且由介电材料组成，例如EP 0353393所述之TiO2、Si3N4、ZnS或聚硅氧烷树脂的介电材料。
按照本发明的记录媒体可以用业内已知的方法制造。
涂覆方法
适用的涂覆方法是例如浸涂、浇涂、刷涂、刮涂与旋涂以及在高真空下进行的蒸气沉积法。当采用浇涂方法时，通常使用有机溶剂中的溶液。当采用溶剂时，应注意所用的载体对各该溶剂不敏感。适用的涂覆方法及溶剂在(例如)EP-A-401 791中有描述。
记录层较好由染料溶液旋涂法施用，已证明令人满意的溶剂较好是醇类，例如2-甲氧基乙醇、正丙醇、异丙醇、异丁醇、正丁醇、戊醇或3-甲基-1-丁醇或较好是有氟化的醇，例如2，2，2三氟乙醇或2，2，3，3-四氟-1-丙醇、八氟戊醇及其混合物。要理解是也可以采用其它溶剂或溶剂混合物，例如EP-A-511 598与EP-A-833 316中所述的那些溶剂混合物。亦可采用醚(二丁基醚)、酮(2，6-二甲基-4-庚酮、5-甲基-2-己酮)或饱和或不饱和烃(甲苯、二甲苯)，例如呈混合物(例如二丁基醚/2，6-二甲基-4-庚酮)或混合组分的形式。
旋涂业内技术人员一般会按常规对他所熟悉的所有溶剂，及其二元与三元混合物进行试验，以期发现能导致高品质且同时成本有效的记录层(含有他选择的固体组分)的溶剂或溶剂混合物。在这样的优化程序中也可以采用已知的工艺技术方法，从而使要进行的实验次数保持最少。
因此，本发明也涉及一种光学记录媒体制造方法，其中将式(I)或(II)的化合物在有机溶剂中的溶液施用到有槽纹的基板上。该施用较好由旋涂法进行。
金属反射层的施用较佳藉由喷镀法、真空蒸气沉积法或化学蒸气沉积法(CVD)进行。由于对载体的高粘合力，因此喷镀技术对于施用金属反射层尤其佳。此类技术是已知的且在专业文献中有所描述(例如J.L.Vossen与W.Kern，″Thin Film Processes″，Academic Press，1978年)。
读出方法
按照本发明的记录媒体的结构主要由读出方法决定；已知功能原理包括测量透射率变化，或较佳测量反射率变化，但测量例如萤光性而非透射率或反射率也是已知的。当按照反射率变化构造记录材料时，可采用以下结构：透明载体/记录层(任选地有多层)/反射层及(当合适时)保护层(不一定透明)；或载体(不一定透明)/反射层/记录层及(当合适时)透明保护层。在第一种情况下，光从载体侧入射，而在后一种情况下辐射从记录层侧入射，或从保护层(若存在)侧入射。在这两种情况下，光检测器皆位于与光同源同侧。最初提到的要按照本发明使用的记录材料的结构通常较佳。
当按照光透射率变化构造记录材料时，可考虑以下不同结构：透明载体/记录层(任选地有多层)及(当合适时)透明保护层。用于记录与用于读出的光可要么从载体侧可么从记录层侧入射，或从保护层(若存在)侧入射，在这种情况下光检测器总是位于相反侧。
当记录层由所述在大约350-450nm吸收的这一类染料制成时，适用的激光器为具有350-500nm波长的激光器，例如有405至415nm波长的市售激光器，尤其半导体激光器。当记录层由所述在大约550nm-650nm吸收的这一类染料制成时，适用的激光器为具有630-650nm波长的激光器，例如有635至640nm波长的市售激光器，尤其半导体激光器。例如，记录是通过按照标记长度调制激光并将其辐射聚焦至记录层上来精确地完成的。从专业文献中得知目前正在研发其它亦可适用之方法。
按照本发明的方法能以高可靠性与稳定性进行信息存储，其特征在于非常好的机械与热稳定性，高的光稳定性及边界鲜明的槽纹带。特别的优点包括高对比度，低颤动性及令人惊讶的高信/噪比，因而达到卓越的读出效果。
信息的读出是按照业内已知之方法，由采用激光辐射暂存吸收或反射之变化来执行，例如在″CD-Player and R-DAT Recorder″(ClausBiesch-Wiepke，Vogel Buchverlag，Wurzburg 1992)所述。
按照本发明的光学记录媒体较佳为WORM型可记录光碟，例如作为DVD-R媒体。它也可以用来作为例如可播放的HD-DVD(高密度数码通用光碟)或Blu-ray光碟，作为电脑存储媒体或作为身份识别与安全卡或用于制造衍射光学元件(例如全息图)。
因此本发明也涉及一种信息的光学记录、存储及重放方法，其中采用按照本发明的记录媒体。记录及重放有利地在350至500nm或600-650nm的波长范围内进行，这取决于染料的吸收最大值。
已发现，按照本发明之式(I)或(II)的新颖吡啶N-氧化物系偶氮染料，与业内已知的染料相比，增强了光敏性及对光与热的稳定性。按照本发明的式(I)或(II)的新颖吡啶N-氧化物系偶氮染料有250-350℃分解温度。此外，这些化合物显示出在有机溶剂中极佳的溶解性，这对于制造光学层的旋涂方法是理想的。
因此，在高密度可记录光碟的记录层中使用这些新化合物是极其有利的。
实施例
实施例1：配位体合成
单偶氮染料(1)：将6.74g 2-氨基-6-甲基吡啶N-氧化物盐酸盐、17ml水及17.5g浓盐酸(34％)的混合物逐渐与9ml 33％w/v亚硝酸钠溶液在0℃混合；在0℃反应1小时后，将过量亚硝酸以氨基磺酸中和。将该重氮化溶液滴加到6.31g N，N’-二甲基巴比妥酸在水(20ml)及乙酸(10ml)中的溶液中，同时以氢氧化钠溶液(30％)将pH值维持在4.2-4.8。将该物料搅拌3小时然后抽吸过滤。将沉淀物用水洗涤并干燥。由滤饼得到10.7g下式(1)的染料配位体。
产率：79％，λmax(CH2Cl2)＝411nm。
实施例2：金属偶氮络合物合成
将3.36g实施例1中所述单偶氮染料(1)与1.36g三水合乙酸钠一起悬浮于70ml乙醇中。加热至回流后，加入1.00g一水合乙酸铜。将染料悬浮液冷却至室温并将所得到的沉淀物搅拌1小时，过滤并用去离子水将残余物洗至不含盐并干燥。得到3.64g下式的化合物(2)。
产率99％，λmax(CH2Cl2)＝417nm，ε(417nm)＝56l/g.cm.DSC：286℃(分解)。TFP中的溶解度可高达20g/l。
实施例3
按实施例2制备染料(3)，而以Ni替代Cu。
产率＝99％，λmax(CH2Cl2)＝433nm，ε(433nm)＝67l/g.cm.DSC：334℃(分解)。TFP中的溶解度可高达20g/l。
实施例4
按照实施例1，采用2-氨基-3-乙氧基吡啶N-氧化物盐酸作为重氮前体来制备单偶氮染料(产率74％，λmax(CH2Cl2)＝404nm)。然后按照实施例2进行金属化，并以Ni替代Cu。获得染料(4)。
产率：92％，λmax(CH2Cl2)＝435nm，ε(435nm)＝68l/g.cm.DSC：308℃(30W/g)(分解)。TFP中的溶解度可高达20g/l。
实施例5
按照实施例1，采用2-氨基-5-溴-3-乙氧基吡啶N-氧化物盐酸盐作为重氮前体来制备单偶氮染料(产率80％)。
然后按照实施例2进行金属化，并以Ni替代Cu。获得染料(5)。
产率56％，λmax(CH2Cl2)＝441nm，ε(441nm)＝60l/g.cm.DSC：271℃(17W/g)(分解)。TFP中的溶解度可高达20g/l。
实施例6
按照实施例1，采用2-氨基-5-溴吡啶N-氧化物作为重氮前体来制备单偶氮染料(产率32％)。
然后按照实施例2进行金属化，并以Ni替代Cu。获得染料(6)。产率：82％.λmax(CH2Cl2)＝438nm，ε(438nm)＝63l/g.cm.TFP中的溶解度可高达20g/l。
实施例7
按照实施例1，采用1-丁基-3-氰基-4-甲基-2-氧代-6-吡啶酚作为偶合组分来制备单偶氮染料(产率84％，λmax(CH2Cl2)＝448nm)。
然后按照实施例2进行金属化。获得染料(7)。
产率：78％，λmax(CH2Cl2)＝463nm，ε(463nm)＝86l/g.cm.DSC：283℃(65W/g)(分解)。TFP中的溶解度可高达20g/l。
实施例8
按照实施例1，采用2-氨基吡啶N-氧化物盐酸盐作为重氮前体且采用3-甲基-1-苯基-2-吡唑啉-5-酮作为偶合组分来制备单偶氮染料(产率：86％)。
然后按照实施例2进行金属化。获得染料(8)。
产率：83％，λmax(CH2Cl2)＝425nm，ε(425nm)＝64l/g.cm.DSC：300℃(60W/g)(分解)。
实施例9
按照实施例1，采用2-氨基-3-乙氧基吡啶N-氧化物盐酸盐作为重氮前体且采用1，3-二乙基-2-硫代巴比妥酸作为偶合组分来制备单偶氮染料(产率：85％)。
然后按照实施例2进行金属化，并以Ni替代Cu。获得染料(9)。产率81％，λmax(CH2Cl2)＝463nm，ε(463nm)＝76l/g.cm.TFP中的溶解度可高达20g/l。
实施例10
按照实施例(9)并以Cu替代Ni制备染料(10)。
产率：80％，λmax(CH2Cl2)＝452nm，ε(452nm)＝65l/g cm.DSC：240℃(24W/g)(分解)。TFP中的溶解度可高达20g/l。
实施例11
按照实施例1，采用2-氨基-3-乙氧基吡啶N-氧化物盐酸盐作为重氮前体且采用1-乙基-6(二氰基亚甲基)-2-吡啶酚作为偶合组分来制备单偶氮染料(产率：43％)。
然后按照实施例2进行金属化，并以Ni替代Cu。获得染料(11)。产率：85％，λmax(CH2Cl2)＝560nm，ε(560nm)＝132l/g.cm.DSC：308℃(7W/g)(分解)。
实施例12
按照实施例1，采用2-氨基-3-羟基吡啶N-氧化物作为重氮前体且采用1-乙基-6-(二氰基亚甲基)-2-吡啶酚作为偶合组分来制备单偶氮染料12(产率：66％)。
λmax(CH2Cl2)＝602nm，ε(at 602nm)＝105l/g.cm.DSC：260℃(60W/g)(分解)。
表1：总结
| 用于蓝色激光记录的染料 | ||||
| 化合物 | λmax(nm) | λmax的ε(l/g.cm) | 分解Pt(℃) | 溶解度(g/l) |
| (2) | 417 | 56 | 286 | ＞20 |
| (3) | 433 | 67 | 334 | ＞20 |
| (4) | 435 | 68 | 308 | ＞20 |
| (5) | 441 | 60 | 271 | ＞20 |
| (6) | 438 | 63 | - | ＞20 |
| (7) | 480 | 107 | 314 | ＞20 |
| (8) | 425 | 64 | 300 | - |
| (9) | 463 | 76 | - | ＞20 |
| (10) | 452 | 65 | 240 | ＞20 |
| 用于红色激光记录的染料 | ||||
| 化合物 | λmax(nm) | λmax的ε(l/g.cm) | 分解Pt(℃) | 溶解度(g/l) |
| (11) | 560 | 132 | 308 | - |
| (12) | 602 | 105 | 260 | - |
*溶解度是在四氟丙醇中评估的
应用实施例
对吡啶N-氧化物系偶氮染料化合物的光学与热学性质进行研究。这些染料显示出在所希望波长处的高吸收性。此外，吸收光谱的形状(这对于光碟反射率及清晰标记边缘的形成仍然至关重要)包含一个包含在350至700nm范围内的主要波长带。
更精确言之，折射率的n值估算在1.0与2.7之间(见实施例1)。已发现其光稳定性与通常以用于光学数据记录的猝灭剂稳定的市售染料相当。
在所需温度范围内的热分解的狭窄阈限值表征了新的吡啶N-氧化物系偶氮染料，这对于在光学数据记录用光学层中的应用是理想的。
总之，该吡啶N-氧化物系偶氮染料化合物符合主要由染料应用产业所要求的技术标准，该染料系用于光学数据记录，尤其用于蓝色或红色激光范围内的下一代光学数据记录媒体中。
Claims (10)
1.一种式(I)或(II)的染料化合物用于光学数据记录用光学层的用途，
其中
R1至R4彼此独立地表示氢、氰基(-CN)、卤素(F、Cl、Br、I)、硝基(NO2)、羟基(-OH)；
C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烯基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8烷氧基(-OR)，其中烷基(R)可以是无取代或有C1-8烷基、C1-8烯基、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基、C1-8烯基或C6-12芳基；
-CX3，其中X可为氯、氟、溴；
-NR5R6，其中R5与R6独立地为氢、C1-8烷基、C1-8烯基或C6-12芳基；
C1-8烷硫基(-SR)，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8亚砜基(-S(O)R)，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8砜基(-SO2R)，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8氨磺酰(-SO2NR5R6)，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8碳酰胺基(-CO2NR5R6)，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8磷酰胺基(-P(O)(NR5R6)2)，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
C1-8磷酸酯基(-P(O)(OR)2)，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
X1表示氧、硫、硒，
-NR，其中R表示氢、氰基、C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-NSO2R，其中R表示C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基，C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-NP(O)(OR)2，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
B表示无取代或有取代的芳香族环；或
以下结构的五员或六员杂环：
其中
R7至R9彼此独立表示氢、卤素、氰基，
C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-SO2R，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
X2至X3表示氧、硫、硒，
-NP，其中R表示氢、氰基、C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基，卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-NSO2R，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
-NP(O)(OR)2，其中R表示C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基，卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
X4表示表示氧、硫、硒，
＝NR，其中R表示氢、氰基、C1-8烷基、烯基或炔基、C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；或＝C(CN)2；
M表示金属原子，包括Al、In、Sn、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Zr、Ru、Rh、Pd、Cd、Hf、Re、Os、Ir、Pt、Hg。
2.按照权利要求1的用途，其中该染料化合物是式(II)的染料化合物，其中该式(II)的染料化合物更具体地是式(III)的染料化合物
M选自Ni、Cu、Co、Zn、Al、Fe、Ru、Pd、Pt、Cr、Mn组成的一组；
R1选自H、Cl、CH3、C2H5、C3H7或无取代苯基，
R2选自H、Br、Cl、F、NR2，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR7R8取代，其中R7与R8独立地为氢、C1-8烷基或C6-12芳基；NO2、CH3、C2H5，
R3选自H、Cl、CH3、C2H5，
R4是氢、CH3、C2H5、OR，其中烷基(R)可以是无取代或有C1-8烷基、羟基(-OH)取代，有C6-12芳基取代或有-NR7R8取代，其中R7与R8独立地为氢、C1-8烷基或C6-12芳基；
R7至R8彼此独立地表示氢、C1-8烷基、烯基或炔基，C3-10环烷基或环烯基，其中烷基可以是无取代或有C1-8烷基、C1-8烷氧基、卤素、羟基(-OH)取代，有C6-12芳基取代或有-NR5R6取代，其中R5与R6独立地为氢、C1-8烷基或C6-12芳基；
X2至X3选自O、S、NR，其中R表示氢、氰基、C1-8烷基。
3.按照权利要求2的用途，其中
M选自Ni、Cu、Co、Zn、Al、Fe、Cr、Mn组成的一组；
R1选自H、CH3，
R2选自H、Br、Cl、NO2、CH3，
R3是氢，
R4选自H、Cl、CH3、OC2H5、OH，
R7到R8彼此独立地选自CH3、C2H5、C3H7(正丙基或异丙基)、C4H9(正丁基，仲丁基或叔丁基)，
X2选自O、S，
X3是O。
4.按照权利要求3的用途，其中
M选自镍、铜或锌，
R1是H，
R2是Br，
R3是氢，
R4是OC2H5，
R7与R8是C2H5，且
X2是S，
X3是O。
5.一种光学层，包含至少一种按照权利要求1至4定义的式(I)或(II)的染料化合物，或至少两种按照权利要求1至4定义的式(I)或(II)的染料化合物的混合物。
6.一种按照权利要求5的光学层的制造方法，包含以下步骤：
(a)提供一基板；
(b)将按照权利要求1至4定义的式(I)或(II)的染料化合物或该染料化合物的混合物溶解于有机溶剂中以形成溶液；
(c)将该溶液(b)涂覆于该基板(a)上；
(d)蒸发该溶剂以形成一染料层。
7.按照权利要求6的方法，其中该基板是聚碳酸酯(PC)或聚甲基丙烯酸甲酯(PMMA)。
8.按照权利要求6的方法，其中该有机溶剂选自C1-8醇、有卤素取代的C1-8醇、C1-8酮、C1-8醚、有卤素取代的C1-4烷烃或酰胺。
9.按照权利要求6的方法，其中该C1-8醇或有卤素取代的C1-8醇选自甲醇、乙醇、异丙醇、双丙酮醇(DAA)、2，2，3，3-四氟丙醇、三氯乙醇、2-氯乙醇、八氟戊醇或六氟丁醇；
该C1-8酮选自丙酮、甲基异丁基酮、甲基乙基酮或3-羟基-3甲基-2-丁酮；
该有卤素取代的C1-4烷烃选自氯仿、二氯甲烷或1-氯丁烷；且
该酰胺选自二甲基甲酰胺或二甲基乙酰胺。
10.一种包含按照权利要求5的光学层的光学记录媒体。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04029031.4 | 2004-12-08 | ||
| EP04029031 | 2004-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101073116A true CN101073116A (zh) | 2007-11-14 |
Family
ID=34927685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2005800406368A Pending CN101073116A (zh) | 2004-12-08 | 2005-12-07 | 光学数据记录用光学层中使用的吡啶n－氧化物系偶氮染料及其金属络合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20080142759A1 (zh) |
| EP (1) | EP1825467A2 (zh) |
| JP (1) | JP2008522868A (zh) |
| KR (1) | KR20070085846A (zh) |
| CN (1) | CN101073116A (zh) |
| AU (1) | AU2005313331A1 (zh) |
| BR (1) | BRPI0518890A2 (zh) |
| MX (1) | MX2007006586A (zh) |
| TW (1) | TW200634099A (zh) |
| WO (1) | WO2006061398A2 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102134262A (zh) * | 2009-12-25 | 2011-07-27 | 住友化学株式会社 | 吡啶酮络合物 |
| CN102134217A (zh) * | 2009-12-25 | 2011-07-27 | 住友化学株式会社 | 吡啶酮络合物 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4417869B2 (ja) * | 2005-03-15 | 2010-02-17 | 株式会社東芝 | 情報記憶媒体、再生方法及び記録方法 |
| WO2007007748A1 (ja) * | 2005-07-14 | 2007-01-18 | Mitsubishi Kagaku Media Co., Ltd. | 光学記録媒体、光記録材料および金属錯体化合物 |
| TW200817477A (en) | 2006-09-28 | 2008-04-16 | Fujifilm Corp | Optical information recording medium and azo-metal complx dye |
| EP1921115B1 (en) | 2006-11-10 | 2010-02-24 | Clariant Finance (BVI) Limited | Use of 3-hydroxy-cyclohex-2-enone azo based dyes in optical layers |
| EP1925642A1 (en) * | 2006-11-27 | 2008-05-28 | Clariant International Ltd. | 3-hydroxy-cyclohex-2-enone based azo dyes, and their use with anionic azo metal complex dyes |
| JP2009114345A (ja) * | 2007-11-07 | 2009-05-28 | Yamada Chem Co Ltd | 金属錯体化合物、光学記録媒体、光記録材料及び色素 |
| JP5352986B2 (ja) * | 2007-11-07 | 2013-11-27 | 山田化学工業株式会社 | 金属錯体化合物、光学記録媒体及び光記録材料 |
| JP4427582B2 (ja) * | 2008-01-31 | 2010-03-10 | 株式会社東芝 | 追記型情報記録媒体及びディスク装置 |
| CN102516795B (zh) * | 2011-12-09 | 2014-04-02 | 青岛双桃精细化工（集团）有限公司 | 一种蓝色染料的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3100766A (en) * | 1961-05-19 | 1963-08-13 | American Cyanamid Co | Metallized azo dyes from 2-aminopyridine-1-oxide |
| US4153065A (en) * | 1972-06-19 | 1979-05-08 | L'oreal | Azo derivatives of pyridine n-oxide for use in hair dye compositions |
| JPS5856239A (ja) * | 1981-09-28 | 1983-04-02 | Tdk Corp | 光記録媒体 |
| DE69109513T2 (de) * | 1990-02-13 | 1996-01-18 | Nippon Telegraph & Telephone | Herstellungsverfahren von dielektrischen Vielschichtenfiltern. |
| WO1991018950A1 (fr) * | 1990-05-25 | 1991-12-12 | Mitsubishi Kasei Corporation | Composition colorante et support d'enregistrement optique |
| KR20010021827A (ko) * | 1997-07-14 | 2001-03-15 | 마츠시타 덴끼 산교 가부시키가이샤 | 광기록 매체 및 그 제조방법 |
| CN100480054C (zh) * | 2000-04-17 | 2009-04-22 | 三菱化学株式会社 | 光学记录介质 |
| TWI295681B (zh) * | 2001-12-19 | 2008-04-11 | Ritek Corp | |
| GB0307695D0 (en) * | 2003-04-02 | 2003-05-07 | Avecia Ltd | Compounds,compositions and processes |
-
2005
- 2005-12-06 TW TW094142997A patent/TW200634099A/zh unknown
- 2005-12-07 US US11/792,867 patent/US20080142759A1/en not_active Abandoned
- 2005-12-07 WO PCT/EP2005/056559 patent/WO2006061398A2/en not_active Application Discontinuation
- 2005-12-07 CN CNA2005800406368A patent/CN101073116A/zh active Pending
- 2005-12-07 JP JP2007544908A patent/JP2008522868A/ja not_active Withdrawn
- 2005-12-07 KR KR1020077012818A patent/KR20070085846A/ko not_active Application Discontinuation
- 2005-12-07 EP EP05819027A patent/EP1825467A2/en not_active Withdrawn
- 2005-12-07 BR BRPI0518890-3A patent/BRPI0518890A2/pt not_active Application Discontinuation
- 2005-12-07 AU AU2005313331A patent/AU2005313331A1/en not_active Abandoned
- 2005-12-07 MX MX2007006586A patent/MX2007006586A/es unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102134262A (zh) * | 2009-12-25 | 2011-07-27 | 住友化学株式会社 | 吡啶酮络合物 |
| CN102134217A (zh) * | 2009-12-25 | 2011-07-27 | 住友化学株式会社 | 吡啶酮络合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006061398A2 (en) | 2006-06-15 |
| TW200634099A (en) | 2006-10-01 |
| EP1825467A2 (en) | 2007-08-29 |
| JP2008522868A (ja) | 2008-07-03 |
| WO2006061398A3 (en) | 2006-08-03 |
| BRPI0518890A2 (pt) | 2008-12-16 |
| MX2007006586A (es) | 2007-07-25 |
| US20080142759A1 (en) | 2008-06-19 |
| AU2005313331A1 (en) | 2006-06-15 |
| KR20070085846A (ko) | 2007-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101073116A (zh) | 光学数据记录用光学层中使用的吡啶n－氧化物系偶氮染料及其金属络合物 | |
| US5962657A (en) | Complex polymethine dyes and their use | |
| US20100093983A1 (en) | Use of indolimium diazamethine cations for optical data recording | |
| CN101023139A (zh) | 噻唑基－吡啶鎓染料用于光学数据记录的用途 | |
| CN101073115A (zh) | 单取代的方形酸金属络合物染料以及其在用于光学数据记录的光学层中的应用 | |
| CN100519530C (zh) | 高储存密度光学记录材料 | |
| CN101632124A (zh) | 二氢吲哚二氮杂次甲基阳离子用于光学数据记录的用途 | |
| WO2007048710A1 (en) | Anionic alkylthiobarbituric acid based azo metal complex dyes and their use in optical layers for optical data recording | |
| CN101001922A (zh) | 用作光学记录介质的氨基安替比林基偶氮配体及其金属络合物 | |
| EP1925642A1 (en) | 3-hydroxy-cyclohex-2-enone based azo dyes, and their use with anionic azo metal complex dyes | |
| JP2007522973A (ja) | 青色レーザーを使用して書き込みが可能な光学記録材料 | |
| WO2007118784A2 (en) | Uses of phthalimide based azo metal complex dyes in optical layers for optical data recording | |
| US20070218408A1 (en) | Antipyrine Based Azo Metal Complex Dyes and Their Use in Optical Layers for Optical Data Recording | |
| TWI261605B (en) | Dye compositon of the optical recording medium | |
| WO2007042409A1 (en) | Barbituric acid based azo metal complex dyes and their use in optical layers for optical data recording | |
| AU2006210275A1 (en) | Cationic antipyrine based azo metal complex dyes for use in optical layers for optical data recording | |
| CN100584892C (zh) | 基于安替比林的偶氮金属络合物染料及其在光数据记录用光层中的用途 | |
| KR20080003790A (ko) | 광정보 기록매체 | |
| EP1921115B1 (en) | Use of 3-hydroxy-cyclohex-2-enone azo based dyes in optical layers | |
| WO2007090797A2 (en) | Indandione based azo metal complex dyes and their use in optical layers for optical data recording | |
| WO2006136493A1 (en) | Antipyrine-indandione based azo metal complex dyes and their use in optical layers for optical data recording | |
| JP2008105392A (ja) | 光情報記録媒体 | |
| WO2007020191A1 (en) | Thiobarbituric acid based azo metal complex dyes and their use in optical layers for optical data recording | |
| WO2007093506A2 (en) | O,p-dialkoxy-phenyl-azometal complex dyes and their use in optical layers for optical data recording | |
| EP1998328A1 (en) | Use of indolinium diazamethine cations for optical data recording |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |