CN1462358A - 在用光可记录的信息层中含有Co-酞菁配合物的光学数据存储器 - Google Patents
在用光可记录的信息层中含有Co-酞菁配合物的光学数据存储器 Download PDFInfo
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- CN1462358A CN1462358A CN01816124.3A CN01816124A CN1462358A CN 1462358 A CN1462358 A CN 1462358A CN 01816124 A CN01816124 A CN 01816124A CN 1462358 A CN1462358 A CN 1462358A
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- Prior art keywords
- amino
- isonitrile
- propyl group
- amine
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- 230000003287 optical effect Effects 0.000 title claims abstract description 21
- 238000013500 data storage Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- -1 pyridine radicals Chemical class 0.000 claims description 247
- 150000001412 amines Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 150000002527 isonitriles Chemical class 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 230000001681 protective effect Effects 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 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 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical compound CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000005936 piperidyl group Chemical group 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002460 imidazoles Chemical class 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- DZHBWZZPLRJLPP-UHFFFAOYSA-N 1-isocyano-2-(2-methoxyethoxy)ethane Chemical compound COCCOCC[N+]#[C-] DZHBWZZPLRJLPP-UHFFFAOYSA-N 0.000 claims description 4
- QVUBMHTYZLUXSP-UHFFFAOYSA-N 1-isocyanopentane Chemical group CCCCC[N+]#[C-] QVUBMHTYZLUXSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- VBDBRROMHZXUIZ-UHFFFAOYSA-N 2-isocyanoethanamine Chemical compound NCC[N+]#[C-] VBDBRROMHZXUIZ-UHFFFAOYSA-N 0.000 claims description 4
- MJZUMMKYWBNKIP-UHFFFAOYSA-N 2-isocyanopropane Chemical compound CC(C)[N+]#[C-] MJZUMMKYWBNKIP-UHFFFAOYSA-N 0.000 claims description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 4
- QFYAJJSCAMUJCH-UHFFFAOYSA-N 3-isocyano-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCC[N+]#[C-] QFYAJJSCAMUJCH-UHFFFAOYSA-N 0.000 claims description 4
- NEXGYFPJGTWVIO-UHFFFAOYSA-N 3-isocyanopropan-1-amine Chemical compound NCCC[N+]#[C-] NEXGYFPJGTWVIO-UHFFFAOYSA-N 0.000 claims description 4
- IVLZMQZYYSFNMA-UHFFFAOYSA-N 4-(3-isocyanopropyl)morpholine Chemical compound [C-]#[N+]CCCN1CCOCC1 IVLZMQZYYSFNMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- 238000007046 ethoxylation reaction Methods 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000003053 piperidines Chemical class 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003233 pyrroles Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 3
- WJJFGJRYSSEGDE-UHFFFAOYSA-N (4-methoxyphenyl)-methylidyneazanium Chemical compound COC1=CC=C([N+]#C)C=C1 WJJFGJRYSSEGDE-UHFFFAOYSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
- WYTRWRQCMRUXCY-UHFFFAOYSA-N 1-butoxy-2-isocyanobenzene Chemical compound CCCCOC1=CC=CC=C1[N+]#[C-] WYTRWRQCMRUXCY-UHFFFAOYSA-N 0.000 claims description 2
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 claims description 2
- RXRQOZYTUCHGHK-UHFFFAOYSA-N 1-isocyano-2-methoxyethane Chemical compound COCC[N+]#[C-] RXRQOZYTUCHGHK-UHFFFAOYSA-N 0.000 claims description 2
- SSWVVEYZXQCZNK-UHFFFAOYSA-N 1-isocyano-2-methylpropane Chemical compound CC(C)C[N+]#[C-] SSWVVEYZXQCZNK-UHFFFAOYSA-N 0.000 claims description 2
- AHNXEGHFRCCMIF-UHFFFAOYSA-N 1-isocyano-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1[N+]#[C-] AHNXEGHFRCCMIF-UHFFFAOYSA-N 0.000 claims description 2
- FKDNUUPUBOAPAC-UHFFFAOYSA-N 1-tert-butyl-2-isocyanobenzene Chemical compound CC(C)(C)C1=CC=CC=C1[N+]#[C-] FKDNUUPUBOAPAC-UHFFFAOYSA-N 0.000 claims description 2
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
- MEGSDTQNBQUWJR-UHFFFAOYSA-N 2-isocyano-1,1-dimethoxyethane Chemical compound COC(OC)C[N+]#[C-] MEGSDTQNBQUWJR-UHFFFAOYSA-N 0.000 claims description 2
- BTGWKUYKNNCKEC-UHFFFAOYSA-N 2-isocyano-1,3-benzoxazole Chemical compound C1=CC=C2OC([N+]#[C-])=NC2=C1 BTGWKUYKNNCKEC-UHFFFAOYSA-N 0.000 claims description 2
- URPQVDCZOCYXNC-UHFFFAOYSA-N 2-isocyano-1,3-thiazole Chemical compound [C-]#[N+]C1=NC=CS1 URPQVDCZOCYXNC-UHFFFAOYSA-N 0.000 claims description 2
- IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 claims description 2
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 2
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 claims description 2
- PXNKOKIXUJWOMI-UHFFFAOYSA-N 2-propan-2-yloxypropan-2-amine Chemical compound CC(C)OC(C)(C)N PXNKOKIXUJWOMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- FLMYQHIFLGJJOP-UHFFFAOYSA-N 3-(isocyanomethyl)heptane Chemical compound CCCCC(CC)C[N+]#[C-] FLMYQHIFLGJJOP-UHFFFAOYSA-N 0.000 claims description 2
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 claims description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- LQXNJUFBNPQZEH-UHFFFAOYSA-N C(CC)C1(N(CCNC1)CCN)CCC Chemical compound C(CC)C1(N(CCNC1)CCN)CCC LQXNJUFBNPQZEH-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 241000370738 Chlorion Species 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- KPTLYMYGLOZVRF-UHFFFAOYSA-N NCC(CCCCC[N+]#[C-])C1=CC=CC=C1 Chemical compound NCC(CCCCC[N+]#[C-])C1=CC=CC=C1 KPTLYMYGLOZVRF-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- FXRLPHUXSPHTQX-UHFFFAOYSA-N [C-]#N.CCO Chemical compound [C-]#N.CCO FXRLPHUXSPHTQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 2
- 150000003927 aminopyridines Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 229940006460 bromide ion Drugs 0.000 claims description 2
- LGFPDDKHVBSPBT-UHFFFAOYSA-N butyl(methylidyne)azanium Chemical compound CCCC[N+]#C LGFPDDKHVBSPBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical compound [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
- CAUSNBQXNXNCJC-UHFFFAOYSA-N ethanol cyanide Chemical compound [C-]#N.CCO.CCO CAUSNBQXNXNCJC-UHFFFAOYSA-N 0.000 claims description 2
- LYSYFIWKZTZUAM-UHFFFAOYSA-N ethyl 4-isocyanobutanoate Chemical compound CCOC(=O)CCC[N+]#[C-] LYSYFIWKZTZUAM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- BPCWCZCOOFUXGQ-UHFFFAOYSA-N isocyanoethane Chemical compound CC[N+]#[C-] BPCWCZCOOFUXGQ-UHFFFAOYSA-N 0.000 claims description 2
- ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 claims description 2
- RIWNFZUWWRVGEU-UHFFFAOYSA-N isocyanomethylbenzene Chemical compound [C-]#[N+]CC1=CC=CC=C1 RIWNFZUWWRVGEU-UHFFFAOYSA-N 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 230000015654 memory Effects 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 2
- PWFUPIULWRJSFS-UHFFFAOYSA-N n,n-diethyl-2-isocyanoethanamine Chemical compound CCN(CC)CC[N+]#[C-] PWFUPIULWRJSFS-UHFFFAOYSA-N 0.000 claims description 2
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 claims description 2
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 2
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 claims description 2
- 239000001007 phthalocyanine dye Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 230000011514 reflex Effects 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 12
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000967 suction filtration Methods 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- TXOZSRCVHASUCW-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropan-1-ol Chemical compound OC(F)CC(F)(F)F TXOZSRCVHASUCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 238000013019 agitation Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 3
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical group [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
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- 238000010926 purge Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000012749 thinning agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 1,2-dihydrophenazine Chemical compound C1=CC=C2N=C(C=CCC3)C3=NC2=C1 ZIZMDHZLHJBNSQ-UHFFFAOYSA-N 0.000 description 1
- OSEKAOVKCSZPNM-UHFFFAOYSA-N 1,3-benzoxazole;1,3-oxazole Chemical compound C1=COC=N1.C1=CC=C2OC=NC2=C1 OSEKAOVKCSZPNM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
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- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- MDIFVPIITXYIGI-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzene-1,2-dicarbonitrile Chemical compound COCCOC1=CC=CC(C#N)=C1C#N MDIFVPIITXYIGI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JISVIRFOSOKJIU-UHFFFAOYSA-N hexylidene Chemical group [CH2+]CCCC[CH-] JISVIRFOSOKJIU-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- PNSKQSWNGULNLS-UHFFFAOYSA-N n-butoxyaniline Chemical compound CCCCONC1=CC=CC=C1 PNSKQSWNGULNLS-UHFFFAOYSA-N 0.000 description 1
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920003050 poly-cycloolefin Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
本发明涉及能够单次写入的光学数据载体,Co-酞菁配合物作为光吸收化合物在光学数据载体尤其是用于CD-R的光学可写式信息层中的用途,以及通过旋转涂布将上述化合物施涂于聚合物基材,尤其聚合物碳酸酯上的方法。
Description
本发明涉及Co-酞菁配合物作为光吸收化合物在单次可记录的光学数据介质的光可记录信息层中的用途,光学数据介质和它们的生产方法。
单次可记录式光盘(CD-R)最近在量上经历了巨大的增长。信息层的光吸收化合物表示了光学数据介质的主要组分,其中必须满足相应的高且不同的要求。相应地,这些化合物的制备相应是复杂的(参阅WO-A-00/09522)。
因此,本发明的目的是提供用作单次可记录式光学数据介质(尤其是CD-R)的信息层中的光吸收化合物的合成简单和满足高要求(如光稳定性,理想的信/噪比,高记录灵敏度,基材的无损应用等)的酞菁染料。
令人惊奇地发现,Co-酞菁配合物适合于所述目的。
本发明涉及含有透明基材的光学数据介质,在所述基材的表面上,施涂至少一可记录信息层,任选的反射层,任选的中间层和/或任选的保护层,特征在于可用光记录的信息层含有作为光吸收化合物的式I的至少一种Co-酞菁配合物:
其中
CoPc表示钴(III)酞菁,
L1和L2是钴中心原子的轴向配位键接的配位体,并且基团R3-R6对应于酞菁的取代基,其中
其中
R0、R1和R2各自独立表示氢,烷基,环烷基,烯基,芳基或杂芳基,或R0-R2的两个与它们所键接的N原子一起形成氢化、部分氢化、似芳族或芳族环,优选5-7元环,其任选含有其它杂原子,尤其N、O和/或S,
R表示烷基,环烷基,烯基,芳基或杂芳基,
R3、R4、R5和R6彼此独立表示卤素,氰基,烷基,芳基,烷基氨基,二烷基氨基,烷氧基,烷基硫基,芳氧基,芳基硫基,SO3H,SO2NR7R8,CO2R12,CONR7R8,NH-COR12或基团-(B)m-D,
B表示选自直接键、CH2、CO、CH(烷基)、C(烷基)2、NH、S、O或-CH=CH-中的桥节(Brückenglied),(B)m表示其中m=1-10,优选m=1、2、3或4的桥节B的化学上有意义的序列,
或表示金属茂基或金属茂基羰基,其中,钛、锰、铁、钌或锇适合作为金属中心,
X1和X2各自独立表示NR′R″,OR″或SR″,
Y1表示NR′,O或S,Y2表示NR′,
n表示1-10和
w、x、y和z彼此独立表示0-12和w+x+y+z≤12,
R7和R8彼此独立表示烷基氨基,羟基烷基氨基,二烷基氨基,双羟基烷基氨基,芳基氨基,或R7和R8与它们所键接的N原子一起形成杂环5-、6-或7-元环,任选还有其它杂原子,尤其是选自O、N和S,其中,NR7R8尤其表示吡咯烷基,哌啶基或吗啉代(Morpholino),
R12表示烷基,芳基,杂芳基或氢,
An-表示阴离子,尤其表示卤阴离子,C1-C20烷基COO-,甲酸根,草酸根,乳酸根,甘醇酸根,柠檬酸根,CH3OSO3 -,NH2SO3 -,CH3SO3 -,1/2SO4 2-或1/3PO4 3-。
其中
CoPc,L2,基团R3-R6和标记w、x、y和z具有与式I相同的含义,和
然而,为了简化起见,以下陈述全部基于式(I)的化合物。然而,它们当然还以相同方式适用于式(Ia)。
在L1和L2的含义中的优选杂环胺配位体是吗啉,哌啶,哌嗪,吡啶,2,2-双吡啶,4,4-双吡啶,哒嗪,嘧啶,吡嗪,咪唑,苯并咪唑,异噁唑,苯并异噁唑,噁唑,苯并噁唑,噻唑,苯并噻唑,喹啉,吡咯,吲哚和3,3-二甲基吲哚,它们在各种情况下在氮原子处与钴原子配位。
烷基、烷氧基、芳基和杂环基任选能够携带其它基团,如烷基,卤素,羟基,羟烷基,氨基,烷基氨基,二烷基氨基,硝基,氰基,CO-NH2,烷氧基,烷氧基羰基,吗啉基,哌啶基,吡咯烷基,吡咯烷酮基,三烷基甲硅烷基,三烷基甲硅烷氧基或苯基。烷基和烷氧基可以是饱和的、不饱和的、直链或支化的,烷基可以部分卤化或全部卤化,烷基和烷氧基可以乙氧基化或丙氧基化或甲硅烷基化。在芳基或杂环基上的相邻烷基和/或烷氧基可以一起形成三或四元桥。
式(I)的优选化合物是其中以下内容适用基团R0-R8,R,R′,R″和R12和配位体L1和L2的那些:
名称为“烷基”的取代基优选表示C1-C16烷基,尤其C1-C6烷基,其任选被卤素,如氯,溴,氟,羟基,氰基和/或C1-C6烷氧基取代;
名称为“烷氧基”的取代基优选表示C1-C16烷氧基,尤其C1-C6烷氧基,其任选被卤素,如氯,溴,氟,羟基,氰基和/或C1-C6烷基取代;
名称为“环烷基”的取代基优选表示C4-C8环烷基,尤其C5-C6环烷基,其任选被卤素,如氯,溴或氟,羟基,氰基和/或C1-C6烷基取代;
名称为“烯基”的取代基优选表示C6-C8烯基,其任选被卤素,如氯,溴或氟,羟基,氰基和/或C1-C6烷基取代,尤其烯基表示烯丙基;
意义为“杂芳基”的取代基优选表示具有5-7元环的杂环基团,其优选含有选自N、S和/或O中的杂原子,任选稠合于芳环或任选携带其它取代基,例如卤素,羟基,氰基和/或烷基,以下是特别优选的:吡啶基,呋喃基,噻吩基,噁唑基,噻唑基,咪唑基,喹啉基,苯并噁唑基,苯并噻唑基和苯并咪唑基,
名称为“芳基”的取代基优选表示C6-C10芳基,尤其苯基或萘基,其任选被卤素,如F,Cl,羟基,C1-C6烷基,C1-C6烷氧基,NO2和/或CN取代。
式(I)的优选的Co-酞菁配合物是其中各符号具有以下含义的那些:
L1和L2彼此独立表示氨,甲基胺,乙基胺,乙醇胺,丙基胺,异丙基胺,丁基胺,异丁基胺,叔丁基胺,戊基胺,叔戊基胺,苄基胺,甲基苯基己基胺,氨基丙基胺,氨基乙基胺,3-二甲基氨基丙基胺,3-二乙基氨基丙基胺,二乙基氨基乙基胺,二丁基氨基丙基胺,吗啉基丙基胺,哌啶基丙基胺,吡咯烷基丙基胺,吡咯烷酮基丙基胺,3-(甲基-羟乙基氨基)丙基胺,甲氧基乙基胺,乙氧基乙基胺,甲氧基丙基胺,乙氧基丙基胺,甲氧基乙氧基丙基胺,3-(2-乙基己氧基)丙基胺,异丙基氧基异丙基胺,二甲基胺,二乙基胺,二乙醇胺,二丙基胺,二异丙基胺,二丁基胺,二异丁基胺,二叔丁基胺,二戊基胺,二叔戊基胺,双(2-乙基己基)胺,双(氨基乙基)胺,双(氨基丙基)-胺,双(二甲基氨基丙基)胺,双(二乙基氨基丙基)胺,双(二乙基氨基乙基)胺,双(二丁基氨基丙基)胺,二(吗啉基丙基)胺,二(哌啶基丙基)胺,二(吡咯烷基丙基)胺,二(吡咯烷酮基丙基)胺,双(3-(甲基-羟乙基氨基)丙基)胺,二甲氧基乙基胺,二乙氧基乙基胺,二甲氧基丙基胺,二乙氧基丙基胺,二(甲氧基乙氧基乙基)胺,二(甲氧基乙氧基-丙基)胺,双(3-(2-乙基己氧基)丙基)胺,二(异丙氧基异丙基)-胺,三丙基胺,三(甲氧基乙氧基乙基)胺,三(甲氧基乙氧基丙基)胺,二乙基氨基乙基哌嗪,二丙基氨基乙基哌嗪,吗啉,哌啶,哌嗪,吡啶基胺,2-噻唑基胺,2-苯并噻唑基胺,2-苯并噁唑基胺,3-亚胺基异假吲哚基(isoindoleninyl)胺,吡啶,丙基吡啶,丁基吡啶,2,2-双吡啶,4,4-双吡啶,哒嗪,嘧啶,吡嗪,咪唑,苯并咪唑,异噁唑,苯并异噁唑,噁唑,苯并噁唑,噻唑,苯并噻唑,喹啉,吡咯,吲哚,3,3-二甲基吲哚,氨基吡啶,苯胺,对甲苯胺,对叔丁基苯胺,对茴香胺,异丙基苯胺,丁氧基苯胺或萘基胺,
或
L1和L2彼此独立地表示甲基异腈,乙基异腈,乙醇异腈,丙基异腈,异丙基异腈,丁基异腈,异丁基异腈,叔丁基异腈,戊基异腈,叔戊基异腈,苄基异腈,甲基苯基己基异腈,氨基丙基异腈,氨基乙基异腈,3-二甲基氨基丙基异腈,3-二乙基氨基丙基异腈,二乙基氨基乙基异腈,二丁基氨基丙基异腈,吗啉基丙基异腈,哌啶基丙基异腈,吡咯烷基丙基异腈,吡咯烷酮基丙基异腈,3-(甲基-羟乙基氨基)-丙基异腈,甲氧基乙基异腈,乙氧基乙基异腈,甲氧基-丙基异腈,乙氧基丙基异腈,甲氧基乙氧基丙基异腈,3-(2-乙基己氧基)丙基异腈,异丙基氧基异丙基异腈,二甲基异腈,二乙基异腈,二乙醇异腈,二丙基异腈,二异丙基异腈,二丁基异腈,二异丁基异腈,二叔丁基异腈,二戊基异腈,二叔戊基异腈,双(2-乙基己基)-异腈,双(氨基乙基)异腈,双(氨基丙基)异腈,双(二甲基氨基丙基)异腈,双(二乙基氨基丙基)异腈,双(二乙基氨基乙基)异腈,双(二丁基氨基丙基)异腈,二(吗啉基丙基)-异腈,二(哌啶基丙基)异腈,二(吡咯烷基丙基)异腈,二(吡咯烷酮基丙基)异腈,双(3-(甲基-羟乙基氨基)丙基)-异腈,二甲氧基乙基异腈,二乙氧基乙基异腈,二甲氧基丙基异腈,二乙氧基丙基异腈,二(甲氧基乙氧基乙基)异腈,二(甲氧基乙氧基丙基)异腈,双(3-(2-乙基己基氧基)丙基)异腈,二(异丙基氧基异丙基)异腈,三丙基异腈,三(甲氧基乙氧基乙基)异腈,三(甲氧基乙氧基丙基)异腈,吡啶基异腈,2-噻唑基异腈,2-苯并噻唑基异腈,2-苯并噁唑基异腈,3-亚胺基异假吲哚基异腈,苯基异腈,对叔丁基苯基异腈,对甲氧基苯基异腈,异丙基苯基异腈,丁氧基苯基异腈或萘基异腈,
R3、R4、R5和R6彼此独立地表示氯,氟,溴,碘,氰基,甲基,乙基,丙基,异丙基,丁基,异丁基,叔丁基,戊基,叔戊基,羟乙基,3-二甲基氨基丙基,3-二乙基氨基丙基,苯基,对叔丁基苯基,对甲氧基苯基,异丙基苯基,三氟甲基苯基,萘基,甲基氨基,乙基氨基,丙基氨基,异丙基氨基,丁基氨基,异丁基氨基,叔丁基氨基,戊基氨基,叔戊基氨基,苄基氨基,甲基苯基己基氨基,羟乙基氨基,氨基丙基氨基,氨基乙基氨基,3-二甲基氨基丙基氨基,3-二乙基氨基丙基氨基,二乙基氨基乙基氨基,二丁基氨基丙基氨基,吗啉基丙基氨基,哌啶基丙基氨基,吡咯烷基丙基氨基,吡咯烷酮基丙基氨基,3-(甲基-羟乙基氨基)-丙基氨基,甲氧基乙基氨基,乙氧基乙基氨基,甲氧基丙基氨基,乙氧基丙基氨基,甲氧基乙氧基丙基氨基,3-(2-乙基己氧基)-丙基氨基,异丙氧基丙基氨基,二甲基氨基,二乙基氨基,二乙醇氨基,二丙基氨基,二异丙基氨基,二丁基氨基,二异丁基氨基,二叔丁基氨基,二戊基氨基,二叔戊基氨基,双(2-乙基己基)氨基,双(氨基丙基)氨基,双(氨基乙基)氨基,双(3-二甲基氨基丙基)氨基,双(3-二乙基氨基丙基)氨基,双(二乙基氨基乙基)氨基,双(二丁基氨基丙基)氨基,二(吗啉基丙基)-氨基,二(哌啶基丙基)氨基,二(吡咯烷基丙基)氨基,二(吡咯烷酮基丙基)氨基,双(3-(甲基羟乙基氨基)丙基)氨基,二甲氧基乙基氨基,二乙氧基乙基氨基,二甲氧基丙基氨基,二乙氧基丙基氨基,二(甲氧基乙氧基乙基)氨基,二(甲氧基乙氧基丙基)氨基,双(3-(2-乙基己氧基)丙基)氨基,二(异丙氧基异丙基)-氨基,甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基,异丁氧基,叔丁氧基,戊氧基,叔戊氧基,甲氧基乙氧基,乙氧基乙氧基,甲氧基丙氧基,乙氧基丙氧基,甲氧基乙氧基丙氧基,3-(2-乙基己氧基)丙氧基,甲基硫基,乙基硫基,丙基硫基,异丙基硫基,丁基硫基,异丁基硫基,叔丁基硫基,戊基硫基,叔戊基硫基,苯基,甲氧基苯基,三氟甲基苯基,萘基,CO2R12,CONR7R8,NH-COR12,SO3H,SO2NR7R8或表示下式的基团:或
其中(B)m表示: 或
星号(*)表示连接5-元环的键,
M表示Mn或Fe阳离子,
w、x、y和z彼此独立表示0-8和w+x+y+z≤12,
An-表示氯离子,溴离子,氟离子,C1-C20烷基COO-,甲酸根,草酸根,乳酸根,甘醇酸根,柠檬酸根,CH3OSO3 -,NH2SO3 -,CH3SO3 -,1/2SO4 2-或1/3PO4 3-,
NR7R8表示氨基,甲基氨基,乙基氨基,丙基氨基,异丙基氨基,丁基氨基,异丁基氨基,叔丁基氨基,戊基氨基,叔戊基氨基,苄基氨基,甲基苯基己基氨基,2-乙基-1-己基氨基,羟乙基氨基,氨基丙基氨基,氨基乙基氨基,3-二甲基氨基丙基氨基,3-二乙基氨基丙基氨基,吗啉基丙基氨基,哌啶基丙基氨基,吡咯烷基丙基氨基,吡咯烷酮基丙基氨基,3-(甲基羟基乙基氨基)丙基氨基,甲氧基乙基氨基,乙氧基乙基氨基,甲氧基丙基氨基,乙氧基丙基氨基,甲氧基乙氧基丙基氨基,3-(2-乙基己氧基)丙基氨基,异丙氧基异丙基氨基,二甲基氨基,二乙基氨基,二丙基氨基,二异丙基氨基,二丁基氨基,二异丁基氨基,二叔丁基氨基,二戊基氨基,二叔戊基氨基,双(2-乙基己基)氨基,二羟乙基氨基,双(氨基丙基)氨基,双(氨基乙基)氨基,双(3-二甲基氨基丙基)氨基,双(3-二乙基氨基丙基)氨基,二(吗啉基丙基)氨基,二(哌啶基丙基)氨基,二(吡咯烷基丙基)氨基,二(吡咯烷酮基丙基)氨基,双(3-(甲基羟乙基氨基)丙基)氨基,二甲氧基乙基氨基,二乙氧基乙基氨基,二甲氧基丙基氨基,二乙氧基丙基氨基,二(甲氧基乙氧基丙基)氨基,双(3-(2-乙基己氧基)丙基)氨基,二(异丙氧基异丙基)氨基,苯胺基,对甲苯胺基,对叔丁基苯胺基,对茴香胺基,异丙基苯胺基或萘基氨基,或NR7R8表示吡咯烷基,哌啶基,哌嗪基或吗啉代。
R12表示氢,甲基,乙基,丙基,异丙基,丁基,异丁基,叔丁基,戊基,叔戊基,苯基,对叔丁基苯基,对甲氧基苯基,异丙基苯基,对三氟甲基苯基,氰基苯基,萘基,4-吡啶基,2-吡啶基,2-喹啉基,2-吡咯基或2-吲哚基,
其中
烷基、烷氧基、芳基和杂环基团任选可以携带其它基团,如烷基、卤素、羟基、羟基烷基、氨基、烷基氨基、二烷基氨基、硝基、氰基、CO-NH2、烷氧基、烷氧基羰基、吗啉代、哌啶基、吡咯烷基、吡咯烷酮基、三烷基甲硅烷基、三烷基甲硅烷氧基或苯基,烷基和/或烷氧基可以是饱和、不饱和、直链或支化的,烷基可以部分卤化或全卤化,烷基和/或烷氧基可以被乙氧基化或丙氧基化或甲硅烷基化,在芳基或杂环基团上的相邻烷基和/或烷氧基可以一起形成三或四元桥。
在本申请的上下文中,氧化还原体系尤其是指在Angew.Chem.1978,927页和Topics of Current Chemistry,Vol.92,1页(1980)中所述的氧化还原体系。
对亚苯基二胺,吩噻嗪,二氢吩嗪,双吡啶鎓盐(Viologene)和喹啉并二甲烷是优选的。
对应于式(Ib)的式I的那些Co配合物是特别优选的:(卤素)0-10 (烷氧基)0-4 An
(Ib),
其中
卤素表示氯,溴或氟,
烷氧基表示C1-C6烷氧基,
R7和R8彼此独立具有上述含义,
AnΘ,CoPc和R2同样具有上述含义。
本发明还涉及式Ic的化合物:(卤素)0-10 (烷氧基)0-4 An
(Ic),
其中
卤素表示氯,溴或氟,
烷氧基表示任选被取代的C1-C6烷氧基,
R7和R8各自独立地具有以上含义,
和其它取代基具有上述含义。
本发明还涉及制备式(Ic)的化合物的方法,其特征在于将被式SO2NR7R8的磺酰胺基取代和任选被卤素和/或烷氧基取代的Co-酞菁氧化,再与胺L1和L2反应,其中R7和R8具有上述含义。
制备优选由任选被卤素和/或烷氧基取代的Co-酞菁起始,通过用氯磺酸和亚硫酰氯在50-130℃下氯磺化和与相应的胺反应来进行,在室温到100℃下,在pH8-12下在水中获得了酰胺。随后的轴向胺取代基的引入优选以已知方式在氧化条件,例如氯或空气,优选空气下进行,在空气的情况下,存在过量胺(参阅实施例13)。在氯的情况下,首先进行氧化,然后添加胺。
除了式I的化合物以外,用光可记录的信息层尤其优选另外含有作为光吸收化合物的带有或没有中心原子的至少一种其它任选取代的酞菁。
适合的中心原子例如是选自Si、Zn、Al、Cu、Pd、Pt、Au和Ag中的一种,尤其是Cu和Pd。
例如,在DE-A 19 925 712中公开的磺酰胺基取代的Cu-酞菁是尤其优选的。式II的那些是尤其优选的:
其中
CuPc代表铜酞菁基团,
A表示任选取代的直链或支化的C2-C6亚烷基,例如亚乙基,亚丙基,亚丁基,亚戊基或亚己基,
R9和R10彼此独立地表示氢,或在各种情况下,是任选取代的直链或支化的C1-C6烷基,如甲基,乙基,丙基,丁基,戊基,己基,尤其是取代的C1-C6羟烷基和是未取代的C1-C6烷基,
或R1和R2与它们所键接的N原子一起形成杂环5-或6元环,其任选含有其它杂原子,例如S、N或O,
x表示2.0-4.0,
y表示0-1.5和
x+y的总和是2.0-4.0,优选2.5-4.0。
尤其优选的混合物的组分是对应于式(IIa)的式(II)的那些:
CuPc-[SO2NH-CH2CH2CH2N(CH2)3] (IIa)
其中
CuPc表示铜酞菁。
如在EP-A-519 395中公开的磺酰胺基或酰胺基取代的酞菁适合作为其它优选的光吸收化合物。
在不同光吸收化合物的混合物的情况下,式(I)的化合物的比例优选是它的10-90%。
重量比为10∶90-90∶10,优选20∶80-80∶20,尤其优选40∶60-60∶40的式(I)的混合物是特别优选的。
除了光吸收化合物以外,信息层还可以含有粘结剂,润湿剂,稳定剂,稀释剂和增感剂和其它组分。
基材可以由光学透明塑料生产,如果必要,该塑料进行表面处理。优选的塑料是聚碳酸酯和聚丙烯酸酯和聚环烯烃或聚烯烃。
反射层可以由通常用于可记录光学数据介质的任何金属或金属合金生产。适合的金属或金属合金可以通过蒸汽沉积和溅射来施涂,并含有例如金,银,铜,铝和它们彼此或与其它金属的合金。
在反射层上的可能的保护层可以由UV可固化的丙烯酸酯组成。
同样可以存在保护反射层,例如防止氧化的可能的中间层。
此外,本发明涉及生产根据本发明的光学数据介质的方法,该方法特征在于在透明基材上,通过用式I的至少一种Co-酞菁配合物,任选地结合适合的粘结剂、添加剂和溶剂涂布用光可记录的信息层,再任选进一步提供反射层,任选的其它中间层和任选的保护层。
基材用式I的光吸收化合物的涂布任选与其它染料、粘结剂和/或溶剂一起进行,优选通过旋转涂布。
为了涂布,优选将式I的光吸收化合物溶解在适合的溶剂或溶剂混合物中(用或不用添加剂),使得式I的化合物为100或100以下,例如10-20重量份/100重量份的溶剂。然后通过溅射或蒸汽沉积将可记录的信息层优选在减压下金属化(反射层),然后可能的话提供保护涂漆(保护层)或其它基材或覆盖层。具有半透明反射层的多层设置也是可行的。
一方面,根据它们对式I的光吸收化合物和其它添加剂的溶解性,另一方面根据对基材的影响最小来选择供涂布式I的光吸收化合物或它们与添加剂和/或粘结剂和其它光吸收化合物的混合物用的溶剂或溶剂混合物。对基材具有很小影响的适合溶剂例如是醇类,醚类,烃类,卤化烃类,烷氧基醇类,酮类。这些溶剂的实例是甲醇,乙醇,丙醇,2,2,3,3-四氟丙醇,丁醇,双丙酮醇,苄醇,四氯乙烷,二氯甲烷,乙醚,二丙醚,二丁基醚,甲基叔丁基醚,甲氧基乙醇,乙氧基乙醇,1-甲基-2-丙醇,甲基乙基酮,4-羟基-4-甲基-2-戊酮,己烷,环己烷,乙基环己烷,辛烷,苯,甲苯和二甲苯。优选溶剂是烃类和醇类,因为它们对基材具有最轻的影响。
用于可记录的信息层的适合添加剂是稳定剂,润湿剂,粘结剂,稀释剂和增感剂。
实施例:
以下制备实施例举例说明了根据本发明适用的染料的制备。
实施例1
在室温下将115gCo-酞菁引入到1L干燥氯苯中。引入16g的氯,再搅拌30分钟。在通过用氮吹扫除去过量氯之后,滴加90g的3-(甲基-羟乙基)丙基胺。在90℃下继续搅拌30分钟,在冷却到室温后用抽吸进行过滤。用1L氯苯和1L水进行冲洗,这样获得的染料在真空中干燥。
λmax670nm(NMP).
通过等摩尔量的其它胺或异腈替换3-(甲基羟乙基)丙基胺来类似地制备以下化合物。
实施例11
在室温下将80g的九溴-氯-Co-酞菁引入到1L的干燥氯苯中。通入5g氯,再搅拌30分钟。在通过用氮吹扫除去过量氯之后,滴加28g的3-(甲基-羟乙基)丙基胺。在90℃下继续搅拌30分钟,在冷却到室温后用抽吸进行过滤。用1L氯苯和1L水进行再冲洗,且染料在真空中干燥。
获得了88g的下式的染料:
λmax684nm(NMP).
类似地通过使用相应摩尔量的其它胺来制备以下化合物。
实施例 | L1和L2 | R3 | R4 | R5-R8 | λmaxnm(NMP) |
12 | 甲氧基-乙氧基-丙基胺 | Br9 | Cl | H | 685 |
13 | 3-二甲基-氨基丙基胺 | Br9 | Cl | H | 684 |
实施例14
氯磺化
在30分钟内将131g98.8%的钴-酞菁引入到394ml的98%氯磺酸中。在25分钟内将该批料加热到119℃,在119℃下搅拌4小时,再冷却到85℃,再在2小时内在85-88℃下滴加120ml的亚硫酰氯(至少98%);然后在20分钟内加热到90-92℃,在90-92℃下搅拌4小时,然后进行搅拌直到室温。
产量:802g的熔体
酰胺形成
将381g熔体排放到1700g冰中。温度=-5℃。立即用抽吸过滤出沉淀的磺酰氯,用1000ml冰水洗涤到中性,再彻底抽吸干燥。潮湿的磺酰氯立即进一步加工。最初引入750g冰和750ml冰水。在搅拌下,将磺酰氯快速引入到该混合物中。然后添加39g的3-二甲基氨基丙基胺。然后在60分钟内将混合物加热到80℃。用10%NaOH溶液将pH值保持在10.00,实验在80℃和pH10.0下搅拌另外45分钟。在冷却到室温后,用抽吸过滤,再用1000ml水分批洗涤。产物在真空干燥烘箱中干燥。产量:126.00g。
轴向配位体的引入
将354g的3-二甲基氨基丙基胺和14g NHCl4在90℃下加热1小时。在冷却到室温之后,添加247g的Co-酞菁-四磺基-3-二甲基氨基丙基酰胺和1g的CoCl2。然后通入空气10小时。将混合物加到5L水中并过滤。染料在真空中干燥。
实施例15
氯磺化
在30分钟内将131g98.8%的钴-酞菁引入到394ml的98%氯磺酸中。在25分钟内将该批料加热到119℃,在119℃下搅拌4小时,再冷却到85℃,并在2小时内在85-88℃下滴加120ml的亚硫酰氯(至少98%);然后在20分钟内加热到90-92℃,在90-92℃下搅拌4小时,然后搅拌直到RT。
产量:802g的熔体
酰胺形成
将381g熔体排放到1700g冰中。温度=-5℃。立即用抽吸过滤出沉淀的磺酰氯,用1000ml冰水洗涤到中性,再彻底抽吸干燥。潮湿的磺酰氯立即进一步加工。最初引入750g冰和750ml冰水。在搅拌下,将磺酰氯快速引入到该混合物中。然后添加54g的甲氧基乙氧基丙基胺。然后在60分钟内将混合物加热到80℃。用10%NaOH溶液将pH保持在10.00,再在80℃和pH10.0下继续搅拌45分钟。在冷却到室温后,用抽吸过滤,再用1000ml水分批洗涤。产物在真空中干燥。产量:112g。
轴向配位体的引入
将199g的Co-酞菁-四磺基甲氧基乙氧基丙基酰胺和280g的咪唑的混合物用DMF补充至大约1000ml,再在开口烧杯中搅拌24小时。将1500ml水滴加到该混合物中。过滤产物,然后用1000ml水洗涤。染料在真空中干燥。获得了下式的197g染料:
λmax670nm(NMP)
实施例16
氯磺化
在30分钟内将131g98.8%的钴-酞菁引入到288ml的98%氯磺酸中。将混合物加热到75℃,并在75℃下搅拌4小时。在加热到80℃之后,在2小时内滴加120ml的亚硫酰氯(至少98%)。混合物在80℃下搅拌4小时,然后搅拌到RT。
产量:712g的熔体
酰胺形成
将402g熔体排放到1700g冰中。立即用抽吸过滤出沉淀的磺酰氯,用1000ml冰水洗涤到中性,再彻底抽吸干燥。潮湿的磺酰氯立即进一步加工。最初引入750g冰和750ml冰水。在搅拌下,将磺酰氯快速引入到该混合物中。然后添加20g的二异丁基胺。然后在60分钟内将混合物加热到80℃。用10%NaOH溶液将pH值保持在10.00,然后在80℃和pH10.00下搅拌另外45分钟。在冷却到室温后,用抽吸过滤,并用1000ml软化水分批洗涤。产物在真空中干燥。产量:95g。
轴向配位体的引入
将354g的3-二甲基氨基丙基胺和14g NHCl4在90℃下加热1小时。在冷却到室温之后,添加219g的Co-酞菁-三磺基二异丁基酰胺和1g的CoCl2。然后通入空气10小时。将混合物加到5L水中并过滤。染料在真空中干燥。
获得了240g的下式染料:
λmax670nm(NMP)
类似地通过使用相应摩尔量的其它胺L1或L2来制备以下化合物:
实施例 | L1和L2 | R3 | R4 | R5 | R6 | R7 | R8 | λmax nm(NMP) |
17 | 3-二甲基氨基丙基胺 | SO3H | (SO2NH-R7)3 | H | H | 3-二甲基氨基丙基 | H | 671 |
18 | 甲氧基乙氧基丙基胺 | Br2 | Cl4 | SO3H | (SO2N-R8R7)3 | 异丁基 | 异丁基 | 679 |
19 | 3-二甲基氨基丙基胺 | (SO2NH-R7)3 | H | H | H | 3-二甲基氨基丙基 | H | 672 |
实施例20
将32g的3-(甲氧基乙氧基)邻苯二甲腈和385ml的1-丁醇加热到沸腾,再添加21g锂。将该混合物在120℃下加热1小时。在冷却之后,添加500ml水,并抽吸过滤。产量:15g染料。
金属的引入:
将15g的绿色染料加入到200ml DMF中,再添加2g CoCl2。将混合物回流2小时。在冷却后,添加200ml水,并抽吸过滤。产量:12g染料。
轴向配位体的引入:
λmax715nm(NMP)
类似地制备以下化合物:
实施例21
λmax718nm(NMP)
实施例22
在室温下制备等重量份的由实施例5获得的CoPc配合物和式IIa的化合物的染料混合物在2,2,3,3-四氟丙醇中的2%溶液。用旋转涂布法将该溶液施涂于预刻槽纹聚碳酸酯基材上。预刻槽纹聚碳酸酯用注塑法作为盘片生产。盘片和槽结构的尺寸对应于通常用于CD-R的那些。具有染料层作为信息载体的盘片用100nm的Ag通过蒸汽沉积来涂布。此后,用旋转涂布法施涂UV-可固化的丙烯酸酯涂层(Acryllack),再用UV灯固化。例如在12mW记录功率和在信息阅读过程中的单一记录速度(1.4m/s)下,通过用于CD-R的工业测试记录仪(PulstecOMT2000×4),获得了对于3T信号具有38%的调制高度(30%-70%是CD-R规格)和对于11T信号具有62%的调制高度(>60%是CD-R规格)。
实施例23
在室温下制备等重量份的由实施例4获得的CoPc配合物和式IIa的化合物的染料混合物在2,2,3,3-四氟丙醇中的2%溶液。该溶液用旋转涂布法施涂。例如在14mW记录功率和在信息阅读过程中的双记录速度(2.8m/s)下,通过用于CD-R的工业测试记录仪(PulstecOMT2000×4),获得了对于3T信号具有32%的调制高度(30%-70%是CD-R规格)和对于11T信号具有68%的调制高度(>60%是CD-R规格)。
实施例24
在室温下制备等重量份的由实施例4获得的Co-Pc配合物和式IIa的化合物在10%乙酸中的染料混合物的32%溶液。该原料溶液用双丙酮醇稀释至8%的染料含量。用类似于实施例22的旋转涂布法将该溶液施涂于基材上,再在基材上提供与实施例20类似的反射层和保护层。然而,在实施例20的变型中,仅50nm的Ag作为反射层施涂。例如在8mW记录功率和在信息阅读过程中的单一记录速度(1.4m/s)下,通过用于CD-R的工业测试记录仪(PulstecOMT2000×4),获得了对于3T信号具有32%的调制高度(30%-70%是CD-R规格)和对于11T信号具有67%的调制高度(>60%是CD-R规格)。
实施例25
在室温下制备由实施例1获得的Co-酞菁配合物在2,2,3,3-四氟丙醇中的2%溶液。用类似于实施例22的旋转涂布法将该溶液施涂于基材上,再在基材上提供与实施例20类似的反射层和保护层。然而,在实施例20的变型中,仅50nm的Ag作为反射层施涂。例如在12mW记录功率和在信息阅读过程中的单一记录速度(1.4m/s)下,通过用于CD-R的工业测试记录仪(Pulstec OMT2000×4),获得了对于3T信号具有34%的调制高度(30%-70%是CD-R规格)和对于11T信号具有62%的调制高度(>60%是CD-R规格)。
Claims (10)
其中
CoPc表示钴(III)酞菁,其中L1和L2是钴中心原子的轴向配位键接的配位体和基团R3-R6对应于酞菁的取代基,其中
L1和L2分别各自独立表示式NR0R1R2的胺或表示式
的异腈,其中
R0、R1和R2各自独立表示氢,烷基,环烷基,烯基,芳基或杂芳基,或R0-R2的两个与它们所键接的N原子一起形成氢化、部分氢化、似芳族或芳族环,优选5-7元环,其任选含有其它杂原子,尤其是N、O和/或S,
R表示烷基,环烷基,烯基,芳基或杂芳基,
R3、R4、R5和R6彼此独立表示卤素,氰基,烷基,芳基,烷基氨基,二烷基氨基,烷氧基,芳氧基,芳基硫基,烷基硫基,SO3H,SO2NR7R8,CO2R12,CONR7R8,NH-COR12或基团-(B)m-D,
B表示选自直接键、CH2、CO、CH(烷基)、C(烷基)2、NH、S、O或-CH=CH-中的桥节,其中,(B)m表示化学上有意义的桥节B的结合,并且m代表1-10,优选m=1,
或表示金属茂基或金属茂基羰基,其中,钛、锰、铁、钌或锇适合作为金属中心,
X1和X2各自独立表示NR′R″,OR″或SR″,
Y1表示NR′,O或S,
Y2表示NR′,
n表示1-10和
w、x、y和z彼此独立地表示0-12和w+x+y+z≤12,
R7和R8彼此独立地表示烷基氨基,羟基烷基氨基,二烷基氨基,双羟基烷基氨基,芳基氨基,或R7和R8与它们所键接的N原子一起形成杂环5-、6-或7-元环,任选还有其它杂原子,尤其是选自O、N和S,其中,NR7R8尤其表示吡咯烷基,哌啶基或吗啉代,
R12表示烷基,芳基,杂芳基或氢,
An-表示阴离子。
2、根据权利要求1的光学数据介质,其特征在于在用光可记录的信息层中含有至少一种式I的Co-酞菁配合物,其中以下内容适用基团R0-R8,R,R′,R″和R12和配位体L1和L2:
名称为“烷基”的取代基表示C1-C16烷基,尤其C1-C6烷基,其任选被卤素,如氯,溴,氟,羟基,氰基和/或C1-C6烷氧基取代;
名称为“烷氧基”的取代基表示C1-C16烷氧基,尤其C1-C6烷氧基,其任选被卤素,如氯,溴,氟,羟基,氰基和/或C1-C6烷基取代;
名称为“环烷基”的取代基优选表示C4-C8环烷基,尤其C5-C6环烷基,其任选被卤素,如氯,溴,氟,羟基,氰基和/或C1-C6烷基取代;
名称为“烯基”的取代基优选表示C6-C8烯基,其任选被卤素,如氯,溴,氟,羟基,氰基和/或C1-C6烷基取代,尤其烯基表示烯丙基;
名称为“杂芳基”的取代基优选表示具有5-7元环的杂环基团,其优选含有选自N、S和/或O中的杂原子,并任选稠合于芳环或任选携带其它取代基,例如卤素,羟基,氰基和/或烷基,其中,以下是特别优选的:吡啶基,呋喃基,噻吩基,噁唑基,噻唑基,咪唑基,喹啉基,苯并噁唑基,苯并噻唑基和苯并咪唑基,
名称为“芳基”的取代基优选表示C6-C10芳基,优选苯基或萘基,其任选被卤素,如F,Cl,羟基,C1-C6烷基,C1-C6烷氧基,NO2和/或CN取代。
3、根据权利要求1的光学数据介质,其特征在于式I的CoPc配合物对应于式Ib:(烷氧基)0-4 An(Ib),
其中取代基具有根据权利要求1的含义。
4、根据权利要求1的光学数据介质,其特征在于在用光可记录的信息层中含有至少一种式I的Co-酞菁配合物,其中:
L1和L2彼此独立地表示氨,甲基胺,乙基胺,乙醇胺,丙基胺,异丙基胺,丁基胺,异丁基胺,叔丁基胺,戊基胺,叔戊基胺,苄基胺,甲基苯基己基胺,氨基丙基胺,氨基乙基胺,3-二甲基氨基丙基胺,3-二乙基氨基丙基胺,二乙基氨基乙基胺,二丁基氨基丙基胺,吗啉基丙基胺,哌啶基丙基胺,吡咯烷基丙基胺,吡咯烷酮基丙基胺,3-(甲基-羟乙基氨基)丙基胺,甲氧基乙基胺,乙氧基乙基胺,甲氧基丙基胺,乙氧基丙基胺,甲氧基乙氧基丙基胺,3-(2-乙基己氧基)丙基胺,异丙基氧基异丙基胺,二甲基胺,二乙基胺,二丙基胺,二异丙基胺,二异丁基胺,二叔丁基胺,二戊基胺,二叔戊基胺,双(2-乙基己基)胺,双(氨基丙基)-胺,双(氨基乙基)胺,双(3-二甲基氨基丙基)胺,双(3-二乙基氨基丙基)胺,双(二乙基氨基乙基)胺,双(二丁基氨基丙基)胺,二(吗啉基丙基)胺,二(哌啶基丙基)胺,二(吡咯烷基丙基)胺,二(吡咯烷酮基丙基)胺,双(3-(甲基-羟乙基氨基)丙基)胺,二甲氧基乙基胺,二乙氧基乙基胺,二甲氧基丙基胺,二乙氧基丙基胺,二(甲氧基乙氧基乙基)胺,二(甲氧基乙氧基-丙基)胺,双(3-(2-乙基己氧基)丙基)胺,二(异丙氧基异丙基)-胺,三丙基胺,三(甲氧基乙氧基乙基)胺,三(甲氧基乙氧基丙基)胺,二乙基氨基乙基哌嗪,二丙基氨基乙基哌嗪,吗啉,哌啶,哌嗪,吡啶基胺,2-噻唑基胺,2-苯并噻唑基胺,2-苯并噁唑基胺,3-亚胺基异假吲哚基胺,吡啶,丙基吡啶,丁基吡啶,2,2-双吡啶,4,4-双吡啶,哒嗪,嘧啶,吡嗪,咪唑,苯并咪唑,异噁唑,苯并异噁唑,噁唑,苯并噁唑,噻唑,苯并噻唑,喹啉,吡咯,吲哚,3,3-二甲基吲哚,氨基吡啶基,苯胺基,对甲苯胺,对叔丁基苯胺基,对茴香胺,异丙基苯胺基,丁氧基苯胺基或萘氨基,
或
L1和L2彼此独立地表示甲基异腈,乙基异腈,乙醇异腈,丙基异腈,异丙基异腈,丁基异腈,异丁基异腈,叔丁基异腈,戊基异腈,叔戊基异腈,苄基异腈,甲基苯基己基异腈,氨基丙基异腈,氨基乙基异腈,3-二甲基氨基丙基异腈,3-二乙基氨基丙基异腈,二乙基氨基乙基异腈,二丁基氨基丙基异腈,吗啉基丙基异腈,哌啶基丙基异腈,吡咯烷基丙基异腈,吡咯烷酮基丙基异腈,3-(甲基-羟乙基氨基)-丙基异腈,甲氧基乙基异腈,乙氧基乙基异腈,甲氧基-丙基异腈,乙氧基丙基异腈,甲氧基乙氧基丙基异腈,3-(2-乙基己氧基)丙基异腈,异丙基氧基异丙基异腈,二甲基异腈,二乙基异腈,二乙醇异腈,二丙基异腈,二异丙基异腈,二丁基异腈,二异丁基异腈,二叔丁基异腈,二戊基异腈,二叔戊基异腈,双(2-乙基己基)-异腈,双(氨基乙基)异腈,双(氨基丙基)异腈,双(二甲基氨基丙基)异腈,双(二乙基氨基丙基)异腈,双(二乙基氨基乙基)异腈,双(二丁基氨基丙基)异腈,二(吗啉基丙基)-异腈,二(哌啶基丙基)异腈,二(吡咯烷基丙基)异腈,二(吡咯烷酮基丙基)异腈,双(3-(甲基-羟乙基氨基)丙基)-异腈,二甲氧基乙基异腈,二乙氧基乙基异腈,二甲氧基丙基异腈,二乙氧基丙基异腈,二(甲氧基乙氧基乙基)异腈,二(甲氧基乙氧基丙基)异腈,双(3-(2-乙基己基氧基)丙基)异腈,二(异丙基氧基异丙基)异腈,三丙基异腈,三(甲氧基乙氧基乙基)异腈,三(甲氧基乙氧基丙基)异腈,吡啶基异腈,2-噻唑基异腈,2-苯并噻唑基异腈,2-苯并噁唑基异腈,3-亚胺基异假吲哚基异腈,苯基异腈,对叔丁基苯基异腈,对甲氧基苯基异腈,异丙基苯基异腈,丁氧基苯基异腈或萘基异腈,
R3、R4、R5和R6彼此独立地表示氯,氟,溴,碘,氰基,甲基,乙基,丙基,异丙基,丁基,异丁基,叔丁基,戊基,叔戊基,羟乙基,3-二甲基氨基丙基,3-二乙基氨基丙基,苯基,对叔丁基苯基,对甲氧基苯基,异丙基苯基,三氟甲基苯基,萘基,甲基氨基,乙基氨基,丙基氨基,异丙基氨基,丁基氨基,异丁基氨基,叔丁基氨基,戊基氨基,叔戊基氨基,苄基氨基,甲基苯基己基氨基,羟乙基氨基,氨基丙基氨基,氨基乙基氨基,3-二甲基氨基丙基氨基,3-二乙基氨基丙基氨基,二乙基氨基乙基氨基,二丁基氨基丙基氨基,吗啉基丙基氨基,哌啶基丙基氨基,吡咯烷基丙基氨基,吡咯烷酮基丙基氨基,3-(甲基-羟乙基氨基)-丙基氨基,甲氧基乙基氨基,乙氧基乙基氨基,甲氧基丙基氨基,乙氧基丙基氨基,甲氧基乙氧基丙基氨基,3-(2-乙基己氧基)-丙基氨基,异丙氧基丙基氨基,二甲基氨基,二乙基氨基,二乙醇氨基,二丙基氨基,二异丙基氨基,二丁基氨基,二异丁基氨基,二叔丁基氨基,二戊基氨基,二叔戊基氨基,双(2-乙基己基)氨基,双(氨基丙基)氨基,双(氨基乙基)氨基,双(3-二甲基氨基丙基)氨基,双(3-二乙基氨基丙基)氨基,双(二乙基氨基乙基)氨基,双(二丁基氨基丙基)氨基,二(吗啉基丙基)-氨基,二(哌啶基丙基)氨基,二(吡咯烷基丙基)氨基,二(吡咯烷酮基丙基)氨基,双(3-(甲基羟乙基氨基)丙基)氨基,二甲氧基乙基氨基,二乙氧基乙基氨基,二甲氧基丙基氨基,二乙氧基丙基氨基,二(甲氧基乙氧基乙基)氨基,二(甲氧基乙氧基丙基)氨基,双(3-(2-乙基己氧基)丙基)氨基,二(异丙氧基异丙基)-氨基,甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基,异丁氧基,叔丁氧基,戊氧基,叔戊氧基,甲氧基乙氧基,乙氧基乙氧基,甲氧基丙氧基,乙氧基丙氧基,甲氧基乙氧基丙氧基,3-(2-乙基己氧基)丙氧基,苯基,甲基硫基,乙基硫基,丙基硫基,异丙基硫基,丁基硫基,异丁基硫基,叔丁基硫基,戊基硫基,叔戊基硫基,甲氧基苯基,三氟甲基苯基,萘基,CO2R12,CONR7R8,NH-COR12,SO3H,SO2NR7R8或表示下式的基团:或
其中(B)m表示:für
或
星号(*)表示连接5-元环的键,
w、x、y和z彼此独立表示0-8和w+x+y+z≤12,
An-表示氯离子,溴离子,氟离子,C1-C20烷基COO-,甲酸根,草酸根,乳酸根,甘醇酸根,柠檬酸根,CH3OSO3 -,NH2SO3 -,CH3SO3 -,1/2SO4 2-或1/3PO4 3-,
NR7R8表示氨基,甲基氨基,乙基氨基,丙基氨基,异丙基氨基,丁基氨基,异丁基氨基,叔丁基氨基,戊基氨基,叔戊基氨基,苄基氨基,甲基苯基己基氨基,2-乙基-1-己基氨基,羟乙基氨基,氨基丙基氨基,氨基乙基氨基,3-二甲基氨基丙基氨基,3-二乙基氨基丙基氨基,吗啉基丙基氨基,哌啶基丙基氨基,吡咯烷基丙基氨基,吡咯烷酮基丙基氨基,3-(甲基羟基乙基氨基)丙基氨基,甲氧基乙基氨基,乙氧基乙基氨基,甲氧基丙基氨基,乙氧基丙基氨基,甲氧基乙氧基丙基氨基,3-(2-乙基己氧基)丙基氨基,异丙氧基异丙基氨基,二甲基氨基,二乙基氨基,二丙基氨基,二异丙基氨基,二丁基氨基,二异丁基氨基,二叔丁基氨基,二戊基氨基,二叔戊基氨基,双(2-乙基己基)氨基,二羟乙基氨基,双(氨基丙基)氨基,双(氨基乙基)氨基,双(3-二甲基氨基丙基)氨基,双(3-二乙基氨基丙基)氨基,二(吗啉基丙基)氨基,二(哌啶基丙基)氨基,二(吡咯烷基丙基)氨基,二(吡咯烷酮基丙基)氨基,双(3-(甲基羟乙基氨基)丙基)氨基,二甲氧基乙基氨基,二乙氧基乙基氨基,二甲氧基丙基氨基,二乙氧基丙基氨基,二(甲氧基乙氧基丙基)氨基,双(3-(2-乙基己氧基)丙基)氨基,二(异丙氧基异丙基)氨基,苯胺基,对甲苯胺基,对叔丁基苯胺基,对茴香胺基,异丙基苯胺基或萘基氨基,或NR7R8尤其表示吡咯烷基,哌啶基,哌嗪基或吗啉代。
R12表示氢,甲基,乙基,丙基,异丙基,丁基,异丁基,叔丁基,戊基,叔戊基,苯基,对叔丁基苯基,对甲氧基苯基,异丙基苯基,对三氟甲基苯基,氰基苯基,萘基,4-吡啶基,2-吡啶基,2-喹啉基,2-吡咯基或2-吲哚基,
其中
烷基、烷氧基、芳基和杂环基团任选可以携带其它基团,如烷基、卤素、羟基、羟基烷基、氨基、烷基氨基、二烷基氨基、硝基、氰基、CO-NH2、烷氧基、烷氧基羰基、吗啉基、哌啶基、吡咯烷基、吡咯烷酮基、三烷基甲硅烷基、三烷基甲硅烷氧基或苯基,烷基和/或烷氧基可以是饱和、不饱和、直链或支化的,烷基可以部分卤化或全卤化,烷基和/或烷氧基可以被乙氧基化或丙氧基化或甲硅烷基化,在芳基或杂环基团上的相邻烷基和/或烷氧基可以一起形成三或四元桥。
5、根据权利要求1的光学数据介质,其特征在于用光可记录的信息层另外含有与(I)不同的含金属或无金属酞菁,其中,中心原子选自Si、Zn、Al、Cu、Pd、Pt、Au和Ag,尤其Cu或Pd。
6、通过用波长700-830nm的光在根据权利要求1的光学数据介质上记录而获得的具有可记录信息层的光学数据介质。
7、根据权利要求1的光学数据介质的生产方法,其特征在于在透明基材上通过用式I的Co-酞菁配合物,任选地结合粘结剂、添加剂和适合溶剂涂布用光可记录的信息层,并任选进一步提供反射层,任选的其它中间层和任选的保护层。
8、式(I)的Co-酞菁配合物作为光学数据存储器的用光可记录的信息层中的光吸收化合物的用途。
9、式Ic的化合物:(卤素)0-10 (烷氧基)0-4 An(Ic)
其中
卤素表示氯,溴或氟,
R7和R8各自独立地具有根据权利要求1中的R7和R8的含义,
烷氧基表示任选被取代的C1-C6烷氧基,
和CoPc,An,L1和L2具有在权利要求1中所述的含义。
10、制备根据权利要求9的化合物的方法,其特征在于将被式SO2NR7R8的磺酰胺基取代和任选被卤素和/或烷氧基取代的Co-酞菁氧化,并与胺L1和L2反应,其中R7和R8具有上述含义。
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DE10115227A DE10115227A1 (de) | 2001-03-28 | 2001-03-28 | Optischer Datenträger enthaltend in der Informationsschicht eine lichtabsorbierende Verbindung mit mehreren chromophoren Zentren |
DE10124585A DE10124585A1 (de) | 2000-09-21 | 2001-05-21 | Optische Datenspeicher enthaltend ein Co-Phthalocyanin-Komplex in der mit Licht beschreibbaren Informationsschicht |
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CN103570734A (zh) * | 2013-11-05 | 2014-02-12 | 福建华天裕科学技术发展有限公司 | 一种酞菁钴二胺化合物的合成方法 |
CN115151596A (zh) * | 2019-12-23 | 2022-10-04 | 三星Sdi株式会社 | 聚合物、包含其的光敏树脂组合物、使用其的光敏树脂膜、滤色器及显示装置 |
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MXPA04004578A (es) * | 2001-11-15 | 2004-08-13 | Ciba Sc Holding Ag | Medio de almacenamiento opticos, escribibles, de alta capacidad, que contienen complejos de metales. |
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 |
TW200504741A (en) * | 2003-06-27 | 2005-02-01 | Ciba Sc Holding Ag | Optical recording materials having high storage density |
WO2005119671A1 (en) * | 2004-06-03 | 2005-12-15 | Clariant International Ltd | Use of squaric acid dyes in optical layers for optical data recording |
KR100991553B1 (ko) | 2008-08-20 | 2010-11-04 | 나노씨엠에스(주) | 디-(4-비닐피리딘) 금속 프탈로시아닌 화합물, 이것을 포함하는 조성물 및 이것의 제조방법 |
CN103059065B (zh) * | 2011-10-20 | 2015-04-22 | 上海拓引数码技术有限公司 | 一种偶氮类金属络合物及其制备方法 |
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US2756119A (en) * | 1948-10-29 | 1956-07-24 | Bayer Ag | Vat dyestuff composition |
DE1569753C3 (de) | 1967-08-31 | 1974-02-14 | Bayer Ag, 5090 Leverkusen | Komplexverbindungen der Kobaltphthalocyaninreihe |
US5248538A (en) * | 1991-06-18 | 1993-09-28 | Eastman Kodak Company | Sulfonamido or amido substituted phthalocyanines for optical recording |
KR100288681B1 (ko) * | 1995-12-25 | 2001-05-02 | 나가시마 므쓰오 | 광 기록 재료 및 광 기록 매체 |
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AU5074200A (en) | 1999-06-07 | 2000-12-28 | Bayer Aktiengesellschaft | Use of cu-phthalocyanine sulfonamides as a dye for write-once optical data storage means |
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- 2001-09-10 AU AU2001285943A patent/AU2001285943A1/en not_active Abandoned
- 2001-09-10 EP EP01965272A patent/EP1322906A1/de not_active Withdrawn
- 2001-09-10 CZ CZ2003832A patent/CZ2003832A3/cs unknown
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CN103570734A (zh) * | 2013-11-05 | 2014-02-12 | 福建华天裕科学技术发展有限公司 | 一种酞菁钴二胺化合物的合成方法 |
CN103570734B (zh) * | 2013-11-05 | 2015-07-15 | 福建华天裕科学技术发展有限公司 | 一种酞菁钴二胺化合物的合成方法 |
CN115151596A (zh) * | 2019-12-23 | 2022-10-04 | 三星Sdi株式会社 | 聚合物、包含其的光敏树脂组合物、使用其的光敏树脂膜、滤色器及显示装置 |
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WO2002025205A1 (de) | 2002-03-28 |
TW556186B (en) | 2003-10-01 |
PL360939A1 (en) | 2004-09-20 |
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