CN1585976A - 含有至少一种氧杂菁染料和至少一种金属配合物的组合物 - Google Patents
含有至少一种氧杂菁染料和至少一种金属配合物的组合物 Download PDFInfo
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- CN1585976A CN1585976A CNA028223918A CN02822391A CN1585976A CN 1585976 A CN1585976 A CN 1585976A CN A028223918 A CNA028223918 A CN A028223918A CN 02822391 A CN02822391 A CN 02822391A CN 1585976 A CN1585976 A CN 1585976A
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- Prior art keywords
- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 29
- 239000000975 dye Substances 0.000 claims abstract description 86
- 230000003287 optical effect Effects 0.000 claims abstract description 28
- 238000010521 absorption reaction Methods 0.000 claims abstract description 23
- -1 phosphonate ester Chemical class 0.000 claims description 132
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 150000003254 radicals Chemical class 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 20
- 150000002500 ions Chemical class 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 17
- 229910019142 PO4 Inorganic materials 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 17
- 239000010452 phosphate Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000004185 ester group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 238000003860 storage Methods 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 6
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 3
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000001261 hydroxy acids Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 239000005077 polysulfide Substances 0.000 claims description 2
- 229920001021 polysulfide Polymers 0.000 claims description 2
- 150000008117 polysulfides Polymers 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 239000000976 ink Substances 0.000 abstract description 9
- 229910052751 metal Inorganic materials 0.000 abstract description 8
- 239000002184 metal Substances 0.000 abstract description 8
- 238000007639 printing Methods 0.000 abstract description 6
- 238000002310 reflectometry Methods 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 6
- 230000003595 spectral effect Effects 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 86
- 150000001875 compounds Chemical class 0.000 description 45
- 229910052799 carbon Inorganic materials 0.000 description 32
- 150000001412 amines Chemical class 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 16
- 150000002367 halogens Chemical class 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 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 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 230000001681 protective effect Effects 0.000 description 10
- 239000003381 stabilizer Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- AAIUWVOMXTVLRG-UHFFFAOYSA-N 8,8-dimethylnonan-1-amine Chemical compound CC(C)(C)CCCCCCCN AAIUWVOMXTVLRG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- BWRHOYDPVJPXMF-UHFFFAOYSA-N carane Chemical compound C1C(C)CCC2C(C)(C)C12 BWRHOYDPVJPXMF-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 4
- WPHGSKGZRAQSGP-UHFFFAOYSA-N norcarane Chemical compound C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229930006728 pinane Natural products 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 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 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 150000002240 furans Chemical class 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 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 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 3
- 125000001786 isothiazolyl group Chemical group 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
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Classifications
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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Abstract
本发明涉及包括至少一种氧杂菁染料和至少一种通式(I-1)或(I-2)的金属配合物的组合物,包括该组合物的记录介质和该组合物在生产光记录介质、滤色器和印刷油墨中的用途。其中各取代基如说明书中所定义。通式(I)的金属配合物的应用令人惊奇地导致了氧杂菁染料以固态聚集的倾向性比较弱,使得即使在固态下也保持有利的窄吸收曲线,结果,可以获得具有高反射性以及在所需光谱区的高灵敏度和良好重放特性的记录介质。
Description
本发明涉及含有至少一种氧杂菁(oxonol)染料和至少一种通式(I-1)或(I-2)的金属配合物的组合物,含有该组合物的记录介质以及这些组合物在生产光记录介质、滤色器和印刷油墨中的用途。通式(I)的金属配合物的应用令人惊奇地导致了氧杂菁染料以固态聚集的倾向性比较弱,使得即使在固态下也保持有利的窄吸收曲线,结果,可以获得具有高反射性以及在所需光谱区的高灵敏度和良好重放特性的记录介质。
本发明的领域是采用一次写入式存储介质进行信息的光存储,信息标记(信息凹点)采用着色剂在已写位置和未写位置的不同光学性能来区分。该技术通常被称为“WORM”(例如,“CD-R”或“DVD-R”)。
可在770-830nm的波长下书写的压缩光盘可从“Optical DataStorage 1989”,Technical Digest Series,Vol.1,45(1988)中得知。它们以减低的读出性能被阅读。根据the Orange BookStandard,介质必须在记录波长下具有65%或65%以上的基本反射率。作为记录介质,例如可以使用花青染料(JP-58/125246),酞菁染料(EP-A-676 751,EP-A-712 904),偶氮染料(US-A-5 441 844),复盐(US-A-4 626 496),偶氮金属配合物(US-A-5 272 047,US-A-5 294 471,EP-A-649 133,EP-A-649 880)或它们的混合物(EP-A-649884)或氧杂菁染料(US-B-6 225 024,EP-A-0 833 314,US-A-4 968593)。除了这些染料以外,记录层可以包括稳定剂如单态氧猝灭剂,荧光猝灭剂和自由基捕获剂。
JP 60-0044390A因此涉及包括基材和记录介质的光记录介质,记录层包括花青染料,或花青染料和粘结剂,另外还有至少一种以下通式的化合物:
其中R301,R302,R303和R304各自是氢原子或单价基团,或成对的R301和R302,R302和R303,以及R303和R304可以彼此连接成六元环,R305和R308各自是氢原子或取代或未取代烷基或芳基,R306是氢原子,羟基或取代或未取代烷基或芳基,R307是取代或未取代烷基或芳基,Z′是形成5或6元环所必需的非金属原子,以及M′是过渡金属原子。
JP 09-164767A此外描述了包括含有酞菁化合物和以下通式的稳定剂的记录层的记录材料:
其中A′是被磺酸基团取代的苯基或萘环,和M″是过渡金属原子。
本发明的目的是获取其中记录层具有高存储容量与突出的其它性能的光记录介质。该记录介质应该可以在600-700nm(优选630-690nm),或低于450nm的相同波长下进行高速写入和读取,具有尽可能少的错误。
现已出人意料地发现,通过将氧杂菁染料与特定金属配合物结合获得了以下优点:
-染料的解聚作用,获得了理想的吸收曲线,而单独使用从EP-A-833 314中得知的染料时的情况却不是这样;
-光稳定性的改进,和
-这些组合物在极性溶剂中的改进溶解性。
本发明因此涉及含有至少一种氧杂菁染料和至少一种,即1-5种,优选1-3种以下通式的金属配合物的组合物:
其中Me是7、8、9、10、11或12,优选9、10或11副族的过渡金属,
D1和D2彼此独立是碳环或杂环或碳环体系或杂环体系,它们可以是未取代的或被一个或多个基团R5和R6取代,
R5和R6是卤素原子,如氟,氯或溴,氨基,烷基氨基,二烷基氨基,硝基,氰基,羟基,未取代或取代烷基,未取代或取代羟烷基,未取代或取代烷氧基,插入一个或多个-O-或-S-和可以是未取代或取代的烷基,酰基,苯基,酯基,如膦酸酯,磷酸酯或羧酸酯基,羧酰胺基,磺酰胺基,铵基,羧酸基,磺酸基,膦酸基或磷酸基或它们的盐,
R1和R4彼此独立是氢原子,或未取代的或取代烷基,芳基或芳烷基,
R2,R2′,R3和R3′彼此独立是氢原子,氰基,未取代或取代烷基,烷氧基,芳基或芳烷基,酯基,羧酰胺基,磺酰胺基,三烷基铵基,羧酸基、磺酸基、膦酸基或磷酸基或它们的盐,或
R2和R3一起,或R2′和R3′一起形成双键,环烷基环或杂环,或
R2、R2′、R3和R3′一起形成芳族碳环或杂环,
R2和R2′一起,和/或R3和R3′一起各对彼此独立形成羰基或硫代羰基,
R7,R7′,R8和R8′彼此独立是氢原子或未取代或取代烷基,芳基或芳烷基,或
R7和R7′一起,和/或R8和R8′一起各对彼此独立形成羰基或硫代羰基,
本发明涉及含有基材和至少一个记录层的光记录介质,其中记录层包括上述组合物,以及上述组合物在生产光记录介质,滤色器(滤光器)和印刷油墨中的用途。
通式(I)的金属配合物与氧杂菁染料的结合应用令人惊奇地导致了氧杂菁染料以固态聚集的倾向性比较弱,使得即使在固态下也保持有利的窄吸收曲线,结果,可以获得具有高反射性以及在所需光谱区的高灵敏度和良好重放特性的记录介质。
所用的金属配合物具有以下通式:
其中Me是7、8、9、10、11或12,优选9、10或11副族的过渡金属,
D1和D2彼此独立是碳环或杂环或碳环体系或杂环体系,它们可以是未取代的或被一个或多个基团R5和R6取代,
R5和R6是卤素原子,如氟,氯或溴,氨基,烷基氨基,二烷基氨基,硝基,氰基,羟基,未取代或取代烷基,未取代或取代羟烷基,未取代或取代烷氧基,插入一个或多个-O-或-S-和可以是未取代或取代的烷基,酰基,苯基,酯基,如膦酸酯,磷酸酯或羧酸酯基,羧酰胺基,磺酰胺基,铵基,羧酸基,磺酸基,膦酸基或磷酸基或它们的盐,
R1和R4彼此独立是氢原子,或未取代或取代烷基,芳基或芳烷基,
R2,R2′,R3和R3′彼此独立是氢原子,氰基,未取代或取代烷基,烷氧基,芳基或芳烷基,酯基,羧酰胺基,磺酰胺基,三烷基铵基,羧酸基、磺酸基、膦酸基或磷酸基或它们的盐,或
R2和R3一起,或R2′和R3′一起形成双键,环烷基环或杂环,或
R2、R2′、R3和R3′一起形成芳族碳环或杂环,
R2和R2′一起,和/或R3和R3′一起各对彼此独立形成羰基或硫代羰基,
R7,R7′,R8和R8′彼此独立是氢原子或未取代或取代烷基,芳基或芳烷基,或
R7和R7′一起,和/或R8和R8′一起各对彼此独立形成羰基或硫代羰基。
与羧酸、磺酸、膦酸或磷酸基形成盐的阳离子的实例是金属阳离子如钠,钾,锂,钙,铁和铜离子,金属配合物阳离子或铵阳离子。
根据本发明,烷基被认为是直链或支化C1-24烷基,优选C1-8烷基,它们可以是未取代或取代的,例如甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,环丁基,正戊基,2-戊基,3-戊基,2,2-二甲基丙基,己基,庚基,2,4,4-三甲基戊基,2-乙基己基或辛基,乙氧基羰基乙基,氰基乙基,二乙基氨基乙基,氯乙基,乙酰氧基乙基和三氟甲基。
根据本发明,烷氧基被认为是直链或支化C1-24烷氧基,即O-C1-24烷基,优选C1-8烷氧基,优选O-C1-8烷基,例如,甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,仲丁氧基,异丁氧基,叔丁氧基,正戊氧基,2-戊氧基,3-戊氧基,2,2-二甲基丙氧基,正己氧基,正庚氧基,正辛氧基,1,1,3,3-四甲基丁氧基或2-乙基己氧基。
根据本发明,酰基或烷基羰基被认为是C1-24烷基羰基,优选C1-8烷基羰基,它们可以是未取代或取代的,例如乙酰基,丙酰基,丁酰基或氯乙酰基。
根据本发明,芳族碳环或芳基被认为是C6-24芳基,优选C6-12芳基,它们可以是未取代或取代的,例如苯基,4-甲基苯基,4-甲氧基苯基,萘基,联苯基,2-芴基,菲基,蒽基或三联苯基。
根据本发明,芳烷基被认为是C7-24芳烷基,优选C7-12芳烷基,它们可以是未取代或取代的,例如,苄基,2-苄基-2-丙基,β-苯乙基,9-芴基,α,α-二甲基苄基,ω-苯基-丁基,ω-苯基-辛基,ω-苯基-十二烷基,或3-甲基-5-(1′,1′,3′,3′-四甲基-丁基)-苄基。
根据本发明,插入一个或多个-O-或-S-的烷基被认为是直链或支化C2-C24烷基,优选C2-C8-烷基,它们可以插入一个或多个-O-或-S-,例如插入1个、2个或3个-O-和/或-S-,获得例如以下结构单元:-(CH2)2OCH3,-(CH2CH2O)CH2CH3,-CH2-O-CH3,-CH2CH2-O-CH2CH3,-CH2CH2CH2-O-CH(CH3)2,-[CH2CH2O]Y1-CH3,其中Y1=1-3,-CH2-CH(CH3)-O-CH2-CH2CH3和-CH2-CH(CH3)-O-CH2-CH3。
根据本发明,表述“酯基”包括羧酸酯-C(O)OR101,膦酸酯-P(O)OR102OR103,和磷酸酯-OP(O)OR102OR103,其中R101是未取代或取代烷基,芳基或芳烷基,或是插入一个或多个-O-或-S-和未取代或被羟基取代的烷基,R102和R103是氢原子,未取代或取代烷基,芳基或芳烷基,或是插入一个或多个-O-或-S-和未取代或被羟基取代的烷基,例如-C(O)OCH2CH2OCH2CH2OCH(CH3)2和-C(O)OCH2CH2OCH2CH2OH。
表述“磺酰胺基”表示基团-SO2NR102R103,其中R102和R103如以上所定义。
氨基,烷基氨基或二烷基氨基被认为是基团-NR104R105,其中R104和R105彼此独立是氢原子,C1-24烷基,C1-24烷基羰基或被卤素取代的C1-24烷基羰基,C1-24烷氧基羰基,C6-24芳基,C7-24芳烷基,或C6-24芳基羰基或C7-24芳烷基羰基,或R104和R105一起形成5-7元杂环。实例是氨基,甲基氨基,乙基氨基,二甲基氨基,二乙基氨基,苯基氨基,甲氧基羰基氨基,乙酰基氨基,乙基羰基氨基,环己基羰基氨基,苯甲酰基氨基或氯乙酰基氨基,吗啉基,哌啶子基或吡咯烷基。
C1-24烷氧基羰基被认为是直链或支化C(O)O-C1-24烷基,优选C(O)O-C1-8烷基,例如甲氧基羰基,乙氧基羰基,正丙氧基羰基,异丙氧基羰基,正丁氧基羰基,仲丁氧基羰基,异丁氧基羰基或叔丁氧基羰基。
C6-24芳基-羰基或C7-24芳烷基-羰基的实例分别是苯基羰基和苄基羰基。
根据本发明,“铵基”被认为是基团-NR106R107R108,其中R106,R107和R108是氢原子或未取代或取代烷基,芳基或芳烷基。
(芳族)杂环(或环体系)的实例是具有3-12个碳原子的杂环,例如2-噻吩基,2-呋喃基,1-吡唑基,2-吡啶基,2-噻唑基,2-噁唑基,2-咪唑基,异噻唑基,三唑基,或由未取代或被1-6个乙基、甲基、亚乙基和/或亚甲基取代基取代的噻吩、呋喃、吡唑、噻唑、噁唑、咪唑、异噻唑、噻二唑、三唑、吡啶或苯环组成的任何其它环体系。
饱和杂环的实例是具有选自氮、氧和硫中的一个或两个杂原子的具有4-6个碳原子的杂环烷烃,例如四氢呋喃,四氢吡喃,1,4-二噁烷,硫杂环戊烷,哌啶,γ-丁内酯,5-氨基戊内酰胺或吡咯烷。
碳环或环体系的实例是具有5-12个碳原子的环烷基,例如环戊烷,环己烷或环庚烷,或具有6-24个碳原子的芳族环,如苯基或萘基。
除非另有规定,以上对于通式(I-1)和(I-2)中的基团给出的定义适用于整个发明。
Me优选是9、10或11副族的过渡金属,尤其是Cu,镍或钴。
R1和R4优选是氢或C1-4烷基,尤其是甲基或乙基。
R2,R2′,R3和R3′彼此独立是氢原子,未取代或被磷酸酯基,例如(PhO)(HO)P(O)O-取代的C1-24烷基;磷酸基团或磷酸酯基;或未取代或被磺酸基团取代的苯基,或者R2和R3一起,或R2′和R3′一起优选形成双键,或环烷基环或杂环:
或
或R2、R2′、R3和R3′一起优选形成以下芳族杂环之一:
(N和Me是为了增加透明度;所形成的环用黑体突出显示)。
R7,R7′,R8和R8′优选是氢原子或未取代或取代C1-8烷基,苯基或苄基,或R7和R7′一起,和/或R8和R8′一起形成羰基或硫代羰基。
优选的基团D1和D2具有以下结构式:
R51、R52、R53、R54=H,
R51、R53、R54=H,R52=CH3,OH,C18H37O,Br,Cl,2,4,4-三甲基苯基-1-氧甲基或SO3H,
R51、R52、R54=H,R53=CH3,OH,C4H9O,C8H17O,C12H25O,3,5,5-三甲基己氧基,2-辛基十二烷氧基,RxO-[CH2CH2-O-]x,其中Rx是甲基和x是1,或Rx是乙基和x是2,或Rx是丁基和x是2,或Rx是甲基和x是3,(CH3CH2O)2P(=O)O-或H2NC(=O)CH2O-,
R51、R52、R53=H,R54=OCH3,CH3或OH,
R51、R54=H和R52=SO3H,R53=CH3,
R51、R53=H和R52、R54=Cl,CH3,OH或Br,
R51、R53=H和R52=t-Bu,R54=CH3,
R51、R53=H和R52=Cl,R54=SO3H,
R51、R53=H和R52=Br,R54=SO3H,
R51、R53=H和R52=Cl,R54=OCH3,或
R51、R53=H和R52=SO3H,R54=OCH3或CH3,R51、R52、R53和R54的优选含义是相同的;
其中
R55=H,R56=H,CO2H,CO2CH3或C(=O)NHPh;R55=Br,R56=CO2H;或R55=SO3H,R56=H。
此外优选R2和R3一起,或R2′和R3′一起形成双键,以及R2′和R3′,或R2和R3视情况而定是氰基。通式(I)的这些化合物是有色的,并且有利于折光指数。本发明因此还涉及其中Me,D1和D2,R5和R6,R1和R4如上文所定义,R2和R3形成双键以及R2′和R3′是氰基的通式(I-1)的金属配合物在信息的光存储中的用途,
该金属配合物优选是以下通式的化合物:
或
其中Me是Cu,Ni,Co或Zn,尤其Cu,
R51、R52、R53、R54、R61、R62、R63和R64是氢原子,卤素原子,如氟,氯或溴,氨基,烷基氨基,二烷基氨基,硝基,氰基,羟基,烷基,羟烷基,烷氧基,插入一个或多个-O-或-S-的烷基,酰基,苯基,酯基,如膦酸酯基、磷酸酯基或羧酸酯基,羧酰胺基,磺酰胺基,二或三烷基铵基,羧酸或磺酸或磷酸基或它们的盐,或
R51和R52一起,和/或R61和R62一起形成未取代或取代苯环,
R1和R4彼此独立是氢原子或未取代或取代烷基,芳基或芳烷基,
R2,R2′,R3和R3′是氢原子,氰基或C1-8烷基;或者R2和R3一起,和/或R2′和R3′一起形成双键,含有5-7个碳原子的未取代或取代环烷基环,或含有5-7个碳原子的未取代或取代芳族环,尤其苯环,
R7,R7′,R8和R8′彼此独立是氢原子或未取代或取代C1-8烷基,苯基或苄基,或
R7和R7′一起,和/或R8和R8′一起彼此独立形成羰基或硫代羰基。
该金属配合物尤其是以下通式的化合物:
其中
Me是Cu,Ni或Co;R51、R52、R53、R54、R61、R62、R63和R64是氢原子,氯原子,溴原子,羟基,可以是未取代或被二或三烷基铵基取代的C1-8烷基,可以未取代或被二或三烷基铵基取代的C1-16烷氧基,可以插入一个或多个-O-或-S-和可以未取代或被二或三烷基铵基取代的C1-8烷基;酯基,如羧酸酯-C(O)OR101,膦酸酯-P(O)OR102OR103,或磷酸酯-OP(O)OR102OR103,其中R101是未取代或取代C1-12烷基,C6-12芳基或C7-12芳烷基,或是插入一个或多个-O-或-S-和未取代或被羟基取代的C1-12烷基,例如-C(O)OCH2CH2OCH2CH2OCH(CH3)2或-C(O)OCH2CH2OCH2CH2OH,R102和R103是氢原子,未取代或取代C1-12烷基,C6-12芳基或C7-12芳烷基,或是插入一个或多个-O-或-S-和未取代或被羟基取代的C1-12烷基,例如-C(O)OCH2CH2OCH2CH2OCH(CH3)2和-C(O)OCH2CH2OCH2CH2OH;羧酰胺基,磺酰胺基或二或三烷基铵基;R1和R4彼此独立是氢原子或烷基;R2,R2′,R3和R3′是氢原子,氰基或C1-8烷基,或者成对的基团R2和R2′一起,以及R3和R3′一起形成双键或环己烷环,基团R51、R52、R53、R54、R61、R62、R63和R64中的至少一个是二或三烷基铵基或被二或三烷基铵基取代;
R7,R7′,R8和R8′彼此独立是氢原子或未取代或取代C1-8烷基,苯基或苄基,或
R7和R7′一起,和/或R8和R8′一起各对彼此独立形成羰基或硫代羰基,使得它们能够起根据本发明的氧杂菁染料的阳离子的作用。
这种离子对的实例是以下所示的组合物M-11:
在铵基不起根据本发明的氧杂菁的阳离子的作用的情况下,阴离子的实例是无机或有机阴离子,如羧酸根,磺酸根,酚根,膦酸根,Cl-,Br-,I-和ClO4 -。
特别优选的是通式(I-5)和(I-6)的化合物,其中:
Me是Cu,Ni或Co;R51、R52、R53、R54、R61、R62、R63和R64是氢原子,氯原子或溴原子,氨基,C1-4烷基氨基,二(C1-4烷基)氨基,氰基,羟基,C1-4烷基,可以是未取代或被三(C1-4烷基)铵基取代的C1-16烷氧基;基团R110O-[CH2CH2-O-]x1,其中R110是C1-4烷基和x是1-4的数值;羧酸酯基,磷酸酯基,羧酰胺基,磺酰胺基,三(C1-4烷基)氨基,羧酸或磺酸或磷酸基或它们的盐,或者R51和R52一起,和/或R61和R62一起形成未取代或取代苯环;R1和R4彼此独立是氢原子或C1-4烷基;R2和R3彼此独立是氢原子或C1-4烷基或一起形成双键或环己烷环,尤其其中取代基如以下表1中所定义的通式(I-5)的化合物:
表1
Ex. | Cpd. | R51 | R52 | R53 | R54 | R61 | R62 | R63 | R64 | R1 | R4 | R2 | R3 | R2′ | R3′ | Me |
29 | M-1Y- | H | H | H | H | H | H | +N(CH3)3Y- | H | CH3 | H | H | CH3 | H | CH3 | Cu |
30 | M-22Y- | H | H | +N(CH3)3Y- | H | H | H | +N(CH3)3Y- | H | H | H | H | H | H | H | Cu |
31 | M-32Y- | H | H | +N(CH3)3Y- | H | H | H | +N(CH3)3Y- | H | H | H | 1) | 1) | H | H | Cu |
32 | M-42Y- | H | H | OCH2CH2-+N(CH3)3Y- | H | H | H | OCH2CH2-+N(CH3)3Y- | H | H | H | H | H | H | H | Cu |
28 | M-5 | H | H | H | H | H | H | H | H | H | H | H | H | H | H | Cu |
33 | M-6 | H | H | H | CH3 | H | H | H | CH3 | H | H | H | H | H | H | Cu |
34 | M-7 | H | H | H | OCH3 | H | H | H | OCH3 | H | H | H | H | H | H | Cu |
35 | M-8 | H | H | OC12H25 | H | H | H | OC12H25 | H | H | H | H | H | H | H | Cu |
36 | M-9 | H | H | OC2H4OCH3 | H | H | H | OC2H4OCH3 | H | H | H | H | H | H | H | Cu |
37 | M-10 | H | H | OC2H4OC2H4OC2H5 | H | H | H | OC2H4OC2H4OC2H5 | H | H | H | H | H | H | H | Cu |
38 | M-11 | H | H | O-tert-C4H9 | H | H | H | O-tert-C4H9 | H | H | H | H | H | H | H | Cu |
39 | M-12 | H | H | H | H | H | H | H | H | C2H5 | C2H5 | H | H | H | H | Cu |
40 | M-13 | CH3 | H | H | CH3 | CH3 | H | H | CH3 | H | H | H | H | H | H | Cu |
41 | M-14 | H | H | H | H | H | H | H | H | H | H | 1) | 1) | H | H | Cu |
42 | M-15 | H | H | H | H | H | H | H | H | H | H | 1) | 1) | H | H | Co |
43 | M-16 | H | 叔-C4H9 | H | tert-C4H9 | H | tert-C4H9 | H | tert-C4H9 | H | H | 1) | 1) | H | H | Ni |
44 | M-17 | H | H | H | H | H | H | H | H | H | H | 1) | 1) | H | H | Ni |
45 | M-18 | H | H | N(CH3)2 | H | H | H | N(CH3)2 | H | H | H | 1) | 1) | H | H | Ni |
46 | M-19 | H | H | OP(O)(OC2H5)2 | H | H | H | OP(O)(OC2H5)2 | H | H | H | H | H | H | H | Cu |
47 | M-20 | H | SO3 -Y1+ | H | H | H | SO3 -Y1+ | H | H | H | H | H | H | H | H | Cu |
48 | M-21 | H | H | O-tert-C4H9 | H | H | H | O-叔-C4H9 | H | H | H | 2) | 2) | CN | CN | Ni |
49 | M-22 | H | H | H | H | H | H | H | H | H | H | 3) | 3) | 3) | 3) | Ni |
50 | M-23 | 4) | 4) | H | 5) | 4) | 4) | H | 5) | H | H | 2) | 2) | CN | CN | Ni |
1)R2和R3一起形成环己烷环;2)R2和R3一起形成双键;3)R2,R2,R3和R3一起形成苯环;4)R51和R52一起,和/或R61和R62一起形成苯环;5)-C(O)OCH2CH2OCH2CH2OH.
上文所述的通式(I)的金属配合物能够根据在EP-A-200 843,EP-A-162 811,EP-A-362 139和EP-A-436 470中所述的方法或按照与之类似的方法来制备。
根据本发明,氧杂菁染料被认为是以下通式的化合物:
和
其中X1是=O,=NR9,或=C(CN)2,R9是取代基;X2是-O,-NR9或-C(CN)2,R9是取代基;E和G在各种情况下是形成具有共轭双键的链所必需的原子组,x和y是0或1,Mk+是有机或无机阳离子,k是1-10的整数,和m是0、1、2、3或4,这意味着,除了真正的氧杂菁染料(X1,X2=0)以外,还包括了氧杂菁染料的衍生物(X1和/或X2≠0)。
更具体地说,氧杂菁染料是以下通式的化合物:
或
其中A1、A2、B1和B2在各种情况下是取代基;Y1和Z1在各种情况下是形成碳环或杂环所必需的原子组;E和G在各种情况下是形成具有共轭双键的链所必需的原子组;X1是=O,=NR9,或=C(CN)2,R9是取代基;X2是-O,-NR9或-C(CN)2,R9是取代基;L是次甲基,它可以是取代的,或利用它可以完成聚甲炔的基团,可以将3、5或7个次甲基连接,以便形成具有共轭双键的链,该链可以是取代的;Mk+是有机或无机阳离子,通式(I-1)或(I-2)的金属配合物还有可能是该阳离子,前提是它携带一个或多个正电荷;x和y是0或1,k是1-10的整数,其中通式(II-2)的氧杂菁染料比通式(II-1)的那些优选。
用基团A1、A2、B1和B2表示的取代基的实例是:
直链或支化C1-24烷基,优选C1-8烷基,它们可以是未取代或取代的,例如甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,环丁基,正戊基,2-戊基,3-戊基,2,2-二甲基丙基,己基,庚基,2,4,4-三甲基戊基,2-乙基己基或辛基,乙氧基羰基乙基,氰基乙基,二乙基氨基乙基,氯乙基,乙酰氧基乙基和三氟甲基,
直链或支化C2-24链烯基,优选C2-8链烯基,它们可以是未取代或取代的,例如乙烯基,烯丙基,2-丙烯-2-基,2-丁烯-1-基,3-丁烯-1-基,1,3-丁二烯-2-基,2-戊烯-1-基,3-戊烯-2-基,2-甲基-1-丁烯-3-基,2-甲基-3-丁烯-2-基,3-甲基-2-丁烯-1-基,1,4-戊二烯-3-基,或己烯基、辛烯基、壬烯基、癸烯基、十二碳烯基、十四碳烯基、十六碳烯基、十八碳烯基、二十碳烯基、二十一碳烯基、二十二碳烯基、二十四碳烯、己二烯基、辛二烯基、壬二烯基、癸二烯基、十二碳二烯基、十四碳二烯基、十六碳二烯基、十八碳二烯基或二十碳二烯基的任何异构体,
直链或支化C1-24烷氧基,即O-C1-24烷基,例如甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,仲丁氧基,异丁氧基,叔丁氧基,正戊氧基,2-戊氧基,3-戊氧基,2,2-二甲基丙氧基,正己氧基,正庚氧基,正辛氧基,1,1,3,3-四甲基丁氧基或2-乙基己氧基,
直链或支化C1-24烷硫基,即S-C1-24烷基,C1-24烷硫基的实例是对于C1-24烷氧基所述的例子,其中醚键的氧原子被硫原子置换,
C6-24芳氧基,即O-C6-24芳基,例如苯氧基或4-甲氧基苯基,
C6-24芳硫基,即S-C6-24芳基,例如苯硫基或4-甲氧基苯硫基,
直链或支化C2-24炔基,优选C2-8炔基,它们可以是未取代的或取代的,例如乙炔基,1-丙炔-3-基,1-丁炔-4-基,1-戊炔-5-基,2-甲基-3-丁炔-2-基,1,4-戊二炔-3-基,1,3-戊二炔-5-基,1-己炔-6-基,顺-3-甲基-2-戊烯-4-炔-1-基,反-3-甲基-2-戊烯-4-炔-1-基,1,3-己二炔-5-基,1-辛炔-8-基,1-壬炔-9-基,1-癸炔-10-基或1-二十四炔-24-基,
C2-18酰基,优选C2-8酰基,它是未取代或取代的,例如乙酰基,丙酰基,丁酰基或氯乙酰基,
C1-24烷基磺酰基,优选C1-8烷基磺酰基,或C6-24芳基磺酰基,优选C6-8芳基磺酰基,它们可以是取代的,例如对甲苯磺酰基,
C3-24环烷基,例如环丙基,环丙基-甲基,环丁基,环戊基,环己基,环己基-甲基,三甲基环己基,苧基,降冰片基,冰片基,降蒈基,蒈基,基,降蒎基,蒎基,1-金刚烷基,2-金刚烷基,5α-gonyl,5ξ-pregnyl,
C6-24芳基,优选C6-10芳基,例如苯基,4-甲基苯基,4-甲氧基苯基,萘基,联苯基,2-芴基,菲基,蒽基,或三联苯基,
C7-24芳烷基,优选C7-12芳烷基,它们可以是取代的,例如苄基,2-苄基-2-丙基,β-苯乙基,9-芴基,α,α-二甲基苄基,ω-苯基-丁基,ω-苯基-辛基,ω-苯基-十二烷基或3-甲基-5-(1′,1′,3′,3′-四甲基-丁基)-苄基,
直链或支化C1-24烷氧基羰基,即C(O)O-C1-24烷基,优选C(O)O-C1-8烷基,例如甲氧基羰基,乙氧基羰基,正丙氧基羰基,异丙氧基羰基,正丁氧基羰基,仲丁氧基羰基,异丁氧基羰基,或叔丁氧基羰基,
C6-24芳氧基羰基,即C(O)O-C7-24芳基,优选C(O)O-C7-12芳基,例如苯氧基羰基,4-甲基苯氧基羰基或4-甲氧基苯氧基羰基,
C2-18酰氧基,优选C2-8酰氧基,它们可以是未取代或取代的,例如乙酰氧基,乙基羰氧基,环己基羰氧基,苯甲酰基氧基,或氯乙酰氧基,
C1-18氨基甲酰基,优选C1-8氨基甲酰基,它们可以是未取代或取代的,例如,氨基甲酰基,甲基氨基甲酰基,乙基氨基甲酰基,正丁基氨基甲酰基,叔丁基氨基甲酰基,二甲基氨基甲酰氧基,吗啉基氨基甲酰基或吡咯烷基氨基甲酰基,
C2-18氨基甲酰氧基,优选C2-8氨基甲酰氧基,它们可以是未取代或取代的,例如甲基氨基甲酰氧基或二乙基氨基甲酰氧基,
具有0-18,优选0-8个碳原子的氨磺酰基,它们可以是未取代或取代的,例如氨磺酰基,甲基氨磺酰基或苯基氨磺酰基,
具有3-12个碳原子的杂环,例如2-噻吩基,2-呋喃基,1-吡唑基,2-吡啶基,2-噻唑基,2-噁唑基,2-咪唑基,异噻唑基,三唑基和未取代或被1-6个乙基、甲基、亚乙基和/或亚甲基取代基取代的由噻吩、呋喃、吡唑、噻唑、噁唑、咪唑、异噻唑、噻二唑、三唑、吡啶或苯环组成的任何其它环体系,
卤素原子,如氟,氯或溴,
羟基,硝基,氰基或羧基,或氨基-NR106R107,其中R106和R107彼此独立是氢原子,C1-24烷基,C1-24烷基羰基,C1-24烷氧基羰基,C6-24芳基,C7-24芳烷基,C6-24芳基羰基,C6-24芳氧基羰基,C6-24芳硫基羰基,例如氨基,甲基氨基,乙基氨基,二甲基氨基,二乙基氨基,苯基氨基,甲氧基羰基氨基,乙酰基氨基,乙基羰基氨基,环己基羰基氨基,苯甲酰基氨基或氯乙酰基氨基,或R106和R107一起形成5-7元杂环,如吗啉基,哌啶子基或吡咯烷基。
当基团可以是未取代或取代的时,取代基的实例是上述可以用基团A1、A2、B1和B2表示的那些取代基。X1是=O,=NR9,或=C(CN)2,优选=O,X2是-O,-NR9或-C(CN)2,优选-O,取代基R9的实例是以上对于A1、A2、B1和B2给出的例子。基团=L-一般能够用以下通式表示:
其中R30、R31、R32、R33、R34、R35和R36彼此独立是氢原子,卤素原子,如氟,氯或溴,未取代或取代C1-8烷基,例如C1-8全氟烷基如三氟甲基,未取代或取代C6-10芳基,如苯基,未取代或取代C7-10芳烷基,如苄基或对甲氧基苄基,或具有2-10个碳原子的杂环,未取代或取代C1-4烷氧基,如甲氧基,环烷氧基,如环己氧基,氨基-NR106R107,其中R106和R107如以上所定义,烷基羰氧基,如乙酰氧基,烷硫基,氰基,或硝基,或
位于相对于彼此的1,3-位置的R30、R31、R32、R33、R34、R35和R36中的两个取代基一起形成具有5或6个碳原子的未取代或取代碳环,如环己烯基或环戊烯基,它们可以是未取代或被一个或多个C1-4烷基和/或C1-4烷氧基取代,
p,q和r是0或1。
L优先选自以下基团:
和
其中p和q彼此独立是0或1,Y是氢原子,未取代或取代C1-4烷基,如甲基或三氟甲基,未取代或取代C7-12芳烷基,如苄基或对甲氧基苄基,未取代或取代C6-12芳基,如苯基,间氯苯基或萘基,未取代或取代C1-4烷氧基,如甲氧基,C5-7环烷氧基,如环己氧基,二取代氨基-NR106R107,R106和R107如以上所定义(氢原子除外),如二甲基,二苯基或甲基苯基,吗啉基,咪唑啉基或乙氧基羰基-哌啶子基,烷基羰氧基,如乙酰氧基,烷硫基,如甲硫基,芳硫基,如苯硫基,氰基,硝基,或卤素原子,如氟,氯或溴原子。特别优选Y是氢原子,氯原子或对甲基苯基和L是基团L-2或L-4。
碳环或杂环的实例如下所示:
(A-47),其中Ra,Rb和Rc可以彼此独立如以上对于A1、A2、B1和B2所定义。
在通式II-2中包括Y1,(E)x和X1,以及Z1,(G)y和X2的环可以是相同或不同的。例如,当合成由两个不同取代基团(A-9)和(A-9’)起始时,一般能够形成三种化合物,即具有两个(A-9)基团或两个(A-9’)基团的化合物和具有(A-9)和(A-9’)基团的化合物。该类混合物也可以用作根据本发明的氧杂菁染料。表述“至少一种氧杂菁染料”可以包括任意数目的氧杂菁染料,但一般是1-5种,优选1、2或3种氧杂菁染料。
在上述基团(A-1)到(A-47)中,优选的是基团(A-5),(A-6),(A-7),(A-11)和(A-14),以及特别优选(A-9)。
Mk+是有机或无机阳离子。用Mk+表示的阳离子的实例是氢阳离子,金属阳离子,如钠,钾,锂,钙,铁和铜离子,金属配合物阳离子,铵阳离子,包括阳离子染料和吡啶鎓阳离子,氧鎓,锍,鏻,硒鎓和碘鎓离子。根据本发明,阳离子一般选自铵阳离子,阳离子染料和被阳离子基团取代的通式(I-1),(I-2),(I-3),(I-4),(I-5)和(I-6)的金属配合物。
原则上,可以使用任何阳离子染料。对于DVD,在550-620nm范围具有最大吸收的阳离子染料是优选的,而对于DVR,在低于450nm下具有最大吸收的阳离子染料是优选的。这些阳离子染料的实例是次甲基染料,尤其花青染料,如零-、一-、二-、三-和五-次甲基花青染料以及高级插烯花青染料(例如,参看Ullmanns Enzyklopdie derTechnischen Chemie,第四版(1978),第16卷,650-656页;第五版,卷A16,509-517),三芳基-和二芳基-甲烷染料,如二苯基-和三苯基-甲烷染料和呫吨染料(例如,参看Ullmanns EnzyklopdiederTechnischen Chemie,第四版(1978),第23卷,387-388,389-405和408-415页;第五版,卷A27,186-188,189-204和209-218页)和吖嗪染料,如吩嗪染料,噁嗪染料和噻嗪染料(例如,UllmannsEnzyklopadie der Technischen Chemie,第五版(1985),卷A3,216-223,224-229和229-235页)。
根据本发明,优选的是在WO 98/28737中描述的以下通式的聚甲炔染料:
其中A1和A2彼此独立是C(CH3)2,O,S,Se或未取代或C1-5烷基或苄基取代的CH=CH;
Q是CR85,CR85-CR86=CR87和CR85-CR86=CR87-CR88=CR89;
R71和R72彼此独立是各自未取代的或被卤素、羟基、C1-12烷氧基或被氰基取代一次或多次的C1-12烷基或C2-12链烯基,或者各自未取代或被基团R77或被两个基团R77和R78取代的C6-12芳基或C7-12芳烷基;
R73、R74、R75和R76彼此独立是氢,卤素,硝基,氰基,羟基,氨基,NHR79,NR79R80,CONH2,CONHR79,CONR79R80,SO2C1-C12烷基,SO2NH2,SO2NHR79,SO2NR79R80,COOH,COOR81,NHCOR82,NR81COR82,NHCOOR82,NR81COOR82,或未取代或单或多卤素,单或多羟基或单或多氰基取代的C1-12烷基,C1-12烷硫基或C1-12烷氧基;或
成对的R73和R74一起,和/或R75和R76一起是未取代或被基团R83取代或被两个基团R83和R84取代的1,4-亚丁-1,3-二烯基,使得与该共用苯基一起形成了萘基。
R85、R86、R87、R88和R89彼此独立是氢,卤素,C1-12烷氧基,未取代或被单或多卤素,单或多羟基,或单或多氰基取代的C1-12烷基、C6-12芳基、C7-12芳烷基或NR79R80;或
成对的R85和R87一起,R86和R88一起,或R87和R89一起是各自未取代或被基团R83取代或被两个基团R83和R84取代的亚乙基、乙叉基、亚丙基、丙叉基、邻亚苯基、α,2-苄叉基或1,8-萘叉基;
R77和R78彼此独立是氢,卤素,硝基,氰基,羟基,氨基,NHR79,NR79R80,CONH2,CONHR79,CONR79R80,SO2C1-12烷基,SO2NH2,SO2NHR79,SO2NR79R80,COOH,COOR81,NHCOR82,NR81COR82,NHCOOR82,NR81COOR82,或各自未取代或被卤素、羟基或氰基取代一次或多次的C1-12烷基、C1- 12烷硫基或C1-12烷氧基;
R79和R80彼此独立是各自未取代的或被卤素、羟基、C1-12烷氧基取代一次或多次的C1-12烷基或C2-12链烯基,或者各自未取代或被基团R83或被两个基团R83和R84取代的C6-12芳基或C7-12芳烷基;或
R79和R80与共用的N一起形成各自未取代或被C1-4烷基取代1-4次的吡咯烷,哌啶,哌嗪或吗啉,或各自未取代或被基团R83或被两个基团R83和R84取代的咔唑、吩噁嗪或吩噻嗪;
R81和R82彼此独立是各自未取代的或被卤素、羟基、C1-12烷氧基取代一次或多次的C1-12烷基或C2-12链烯基,或者各自未取代或被基团R83或被两个基团R83和R84取代的C6-12芳基或C7-12芳烷基;
R83和R84彼此独立是卤素,硝基,氰基,羟基,NR90R91,CONH2,CONHR90,CONR90R91,SO2C1-12烷基,SO2NR90R91,COOH,COOR92,NHCOR93,NHCOOR93,NR92COR93,NR92COOR93,或各自未取代或被卤素取代一次或多次的C1-12烷基或C1-12烷氧基;
R90和R91彼此独立是氢,C6-12芳基,C7-12芳烷基;或各自未取代或被卤素、羟基或C1-12烷氧基取代一次或多次的C1-12烷基或C2-12链烯基;或
R90和R91与共用N一起形成各自未取代或被C1-4烷基取代1-4次的吡咯烷,哌啶,哌嗪或吗啉;或咔唑,吩噁嗪或吩噻嗪;和
R92和R93彼此独立是C6-12芳基,C7-12芳烷基,或被卤素、羟基或C1-12烷氧基取代一次或多次的C1-12烷基或C2-12链烯基。优选的是在WO98/28737的实施例A1-A24中所述的化合物CY-1到CY-24。
其中阳离子是花青染料的优选组合物的实例是在实施例25和26中所述的组合物D-50和D-51:
通常,被一个或多个阳离子基团,尤其铵基取代的通式(I-1)或(I-2)的那些金属配合物适合作为阳离子Mk+。
Mk+还可以是通式+NR11R12R13R14的铵阳离子,其中R11,R12,R13和R14是氢原子,直链或支化C1-36烷基,优选C1-16烷基,它们可以是未取代或取代的,例如甲基,乙基,正丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,环丁基,正戊基,2-戊基,3-戊基,2,2-二甲基丙基,己基,庚基,2,4,4-三甲基戊基,2-乙基己基或辛基,乙氧基羰基乙基,氰基乙基,二乙基氨基乙基,氯乙基,乙酰氧基乙基和三氟甲基,
直链或支化C2-36链烯基,优选C2-16链烯基,它们可以是未取代或取代的,例如乙烯基,烯丙基,2-丙烯-2-基,2-丁烯-1-基,3-丁烯-1-基,1,3-丁二烯-2-基,2-戊烯-1-基,3-戊烯-2-基,2-甲基-1-丁烯-3-基,2-甲基-3-丁烯-2-基,3-甲基-2-丁烯-1-基,1,4-戊二烯-3-基,或己烯基、辛烯基、壬烯基、癸烯基、十二碳烯基、十四碳烯基、十六碳烯基、十八碳烯基、二十碳烯基、二十一碳烯基、二十二碳烯基、二十四碳烯、己二烯基、辛二烯基、壬二烯基、癸二烯基、十二碳二烯基、十四碳二烯基、十六碳二烯基、十八碳二烯基或二十碳二烯基的任何异构体,
C2-36酰基,优选C2-16酰基,它们可以是未取代或取代的,例如乙酰基,丙酰基,丁酰基或氯乙酰基,
C1-24烷基磺酰基,优选C1-16烷基磺酰基,或C6-24芳基磺酰基,优选C6-8芳基磺酰基,它们可以是取代的,例如对甲苯磺酰基,
C3-24环烷基,它们可以是取代的,例如环丙基,环丙基-甲基,环丁基,环戊基,环己基,环己基-甲基,三甲基环己基,苧基,降冰片基,冰片基,降蒈基,蒈基,基,降蒎基,蒎基,1-金刚烷基,2-金刚烷基,5α-gonyl或5ξ-pregnyl,
C6-24芳基,优选C6-10芳基,它们可以是取代的,例如苯基,4-甲基苯基,4-甲氧基苯基,萘基,联苯基,2-芴基,菲基,蒽基,或三联苯基,
C7-24芳烷基,优选C7-12芳烷基,它们可以是取代的,例如苄基,2-苄基-2-丙基,β-苯乙基,9-芴基,α,α-二甲基苄基,ω-苯基-丁基,ω-苯基-辛基,ω-苯基-十二烷基或3-甲基-5-(1′,1′,3′,3′-四甲基-丁基)-苄基,
直链或支化C1-24烷氧基羰基,即C(O)O-C1-24烷基,优选C(O)O-C1-8烷基,例如甲氧基羰基,乙氧基羰基,正丙氧基羰基,异丙氧基羰基,正丁氧基羰基,仲丁氧基羰基,异丁氧基羰基,或叔丁氧基羰基,
具有3-12个碳原子的杂环,例如2-噻吩基,2-呋喃基,1-吡唑基,2-吡啶基,2-噻唑基,2-噁唑基,2-咪唑基,异噻唑基,三唑基,或未取代或被1-6个乙基、甲基、亚乙基和/或亚甲基取代基取代的由噻吩、呋喃、吡唑、噻唑、噁唑、咪唑、异噻唑、噻二唑、三唑、吡啶或苯环组成的任何其它环体系。
伯、仲、叔和季铵阳离子是适合的。
该四价氮还可以是5或6元环的环原子。这些体系还可以含有另外的杂原子,例如S,N和O。这些体系的实例是由1,5-二氮杂双环[4.3.0]壬-5-烯(DBN)和1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)衍生的铵阳离子。
还适合的是具有1-10,尤其2-4个铵阳离子的多铵盐,在这种情况下,以上对于“单”化合物所述的取代基可以存在于氮上和该四价氮还可以是5或6元环的环原子(例如参看下文给出的通式VI-3到VI-8)。
例如,在US-B1-6 225 024中所述的化合物B1到B180是季铵阳离子的实例。
优选的是以下铵阳离子:
其中R10、R10′和R10″彼此独立是氢原子,未取代或例如被1-3个C1-4烷基取代的C3-24环烷基,例如环己基或3,3,5-三甲基环己基,或松香胺D,或直链或支化C1-24烷基,R11、R12、R13和R14是氢原子,直链或支化C1-36烷基,优选C1-16烷基,它们可以是未取代或取代,在R11、R12、R13和R14中的碳原子的总数为4-36,优选8-22,由于其空间屏蔽作用,特别优选的是由2,6-二叔丁基吡啶鎓或其中胺氮键接于叔碳原子的具有高度支化烷基链的伯脂族胺,如PRIMENE 81-R(Rohm & HaasCompany;具有12-14个碳原子的胺异构体的混合物)或PRIMENEJM-T(Rohm & Haas Company;具有16-22个碳原子的胺异构体的混合物)或乙基二异丙基胺(Hünig碱)衍生的铵阳离子,或是直链或支化羟基-C1-36烷基,尤其羟基-C1-8烷基,C6-24芳基,尤其C6-10芳基,或C7-24芳烷基,尤其C7-12芳烷基,或基团R11、R12、R13和R14中的两个与它们所键接的氮原子一起形成5或6元杂环,如吡咯烷基,哌啶子基或吗啉基;或
优选
其中R67和R68彼此独立是取代基,R65和R66彼此独立是取代或未取代的烷基,取代或未取代的链烯基,取代或未取代炔基,取代或未取代芳烷基,取代或未取代芳基,或者取代或未取代杂环基,成对的R67和R68,R67和R65,R68和R66,以及R65和R66可以连接成环,以及s和t彼此独立是0或1-4的整数,前提是当s和t具有2或2以上的值时,基团R67和R68可以是相同或不同的(US-B1-6 225 024);
或通式:
其中R69是直链或支化C1-8烷基,尤其甲基,乙基,丙基,丁基,或叔丁基,它们可以是未取代或取代的,例如被氰基,卤素原子或被C1-4烷氧基取代;
其中R201、R202和R203彼此独立是氢原子,直链或支化C1-36烷基,优选C1-16烷基,它们可以是未取代或取代的,羟基-C1-36烷基,优选羟基-C1-8烷基,它们可以是未取代或被一个或多个C1-4烷基和/或C1-4烷氧基取代,C3-24环烷基,尤其C5-7环烷基,C6-24芳基,尤其C6-10芳基,或C7-24芳烷基,尤其C7-12芳烷基,或者基团R201、R202和R203中的两个与它们所键接的氮一起形成5或6元杂环,R204是氢原子,C1-4烷基或C1-4烷氧基,u和v是1-3的整数,u和v的和是3、4或5,和
X是二价连接基团,例如未取代或被一个或多个C1-4烷基和/或C1- 4烷氧基取代的C1-8亚烷基,或基团:
其中R204如上文所定义,Ar是未取代或被一个或多个C1-4烷基和/或C1-4烷氧基取代的C6-10芳基,Cy是未取代或被一个或多个C1-4烷基和/或C1-4烷氧基取代的C5-7环烷基,和t是0-4的整数。
通式VI-7的二铵化合物尤其由以下的胺衍生而来:1,2-二氨基乙烷,1,2-二氨基-1-甲基乙烷,1,2-二氨基-1,2-二甲基乙烷,1,2-二氨基-1,1-二甲基乙烷,1,2-二氨基丙烷,1,3-二氨基丙烷,1,3-二氨基-2-羟基丙烷,N-甲基-1,2-二氨基乙烷,1,4-二氮杂环己烷,1,2-二氨基-1,1-二甲基乙烷,2,3-二氨基丁烷,1,4-二氨基丁烷,N-羟乙基-1,2-二氨基乙烷,1-乙基-1,3-二氨基丙烷,2,2-二甲基-1,3-二氨基丙烷,1,5-二氨基戊烷,2-甲基-1,5-二氨基戊烷,2,3-二氨基-2,3-二甲基丁烷,N-2-氨基乙基吗啉,1,6-二氨基己烷,1,6-二氨基-2,2,4-三甲基己烷,N,N-二羟乙基-1,2-二氨基乙烷,N,N-二甲基-1,2-二氨基乙烷,4,9-二氧杂-1,12-二氨基十二烷,1,2-二氨基环己烷,1,3-二氨基-4-甲基环己烷,1,2-二氨基环己烷,1-氨基-2-氨基甲基-2-甲基-4,4-二甲基环己烷,1,3-二氨基甲基环己烷,N-2-氨基乙基哌嗪,1,1-二(4-氨基环己基)甲烷,1,1-二(4-氨基苯基)甲烷,N,N’-二异丙基-对亚苯基二胺,N,N’-二仲丁基对亚苯基二胺,N,N’-双(1,4-二甲基-戊基)-对亚苯基二胺,N,N’-双(1-乙基-3-甲基-戊基)-对亚苯基二胺,N,N’-双(1-甲基-庚基)-对亚苯基二胺,N,N’-二环己基-对亚苯基二胺,N,N’-二苯基-对亚苯基二胺,N,N’-二(2-萘基)-对亚苯基二胺,N-异丙基-N’-苯基-对亚苯基二胺,N-(1,3-二甲基-丁基)-N’-苯基-对亚苯基二胺,N-(1-甲基-庚基)-N’-苯基-对亚苯基二胺,N-环己基-N’-苯基-对亚苯基二胺和N,N’-二甲基-N,N’-二仲丁基-对亚苯基二胺。
特别优选的是以下化合物:
适合的氧杂菁染料是以下通式的氧杂菁染料:
和
它们描述在EP-A-0 833 314中,
和其中A1,A2,B1,B2;E,G,Y1,Z1;X1,X2,Mk+,m,n,x,y和k如上文所定义和L1,L2,L3,L4和L5是次甲基,它们可以具有取代基。应该指出的是,与在EP-A-833314中所述的氧杂菁染料相反,在该文中Mk+是含有不键接氢原子的带正电荷鎓离子的鎓离子(季铵离子)(参照EP-A-833 314的对比实施例5,其中表明了使用叔铵阳离子没有获得充分的调制系数或光牢度性能),根据本发明,可以使用有机或无机阳离子作为Mk+,也就是说,例如,还可以使用伯、仲或叔铵阳离子。通式(II-4)的氧杂菁染料比通式(II-3)的那些更为优选。
进一步优选的是以下通式的氧杂菁染料:
和
其中Ra是CO2C1-4烷基,氰基,CF3,C(O)NHC1-4烷基,C(O)NH苯基,苯基,OH,C1-4烷基,C1-4烷氧基,NHC(O)C1-4烷基,NHC(O)苯基,C(O)NHC1-4烷基,C(O)NH苯基,NHC(O)OC1-4烷基,NHC(O)O苯基或NH2,
或是
或
Rb是H,C1-4烷基,苯基,羟烷基,C(O)NHC1-4烷基,C(O)NH苯基,邻甲基苯基,苄基或2,4,6-三氯苯基,和
Y是H,C1-4烷基,苯基,苄基,C(O)NH2或卤素,如氯或溴,
Ra是H,苯基或C1-4烷基,
Rb是H,C1-4烷基,苯基,羟基-C1-4烷基,邻甲基苯基或苄基,和Y是H,C1-4烷基,苯基,苄基,C(O)NH2或卤素,如氯或溴,
X,k和Mk+如上文所定义。
还适合的是在US-B1-6 225 024中所述的以下通式的氧杂菁染料:
其中R21,R22,R23和R24彼此独立是氢原子,取代或未取代烷基,取代或未取代芳基,取代或未取代芳烷基或取代或未取代杂环基团,L21,L22和L23彼此独立是可以具有取代基的次甲基,m是整数0、1、2或3,Mk+是有机或无机阳离子,和k是1-10,优选1-4的整数,前提是当m是2或3时,基团L22和L23可以是相同或不同的。
特别优选的是以下通式的化合物:
其中R21,R22,R23和R24彼此独立是氢原子,C1-8烷基,C1-8全氟烷基,如三氟甲基,C1-8链烯基,C1-4烷氧基-C1-4烷基,羟基-C1-4烷基,R104R105N-C1-4烷基,R104和R105如上文所定义,C6-10芳基,如苯基,C7-10芳烷基,如苄基,或具有2-10个碳原子的杂环,或
R21和R22一起,和/或R23和R24一起形成未取代或取代碳环,优选具有3-10个碳原子,如环丙基,环丁基,环戊基,环己基,2-甲基环己基,环庚基或环辛基,或未取代或取代杂环,优选具有2-10个碳原子,如哌啶基,苯并二氢吡喃基或吗啉基(morpholyl),该环可以是未取代的或被一个或多个C1-4烷基和/或C1-4烷氧基取代,
R30、R31、R32、R33、R34、R35和R36彼此独立是氢原子,卤素原子,如氯或溴,C1-8烷基,C1-8全氟烷基,如三氟甲基,C6-10芳基,如苯基,C7-10芳烷基,如苄基,或具有2-10个碳原子的杂环,或
位于相对于彼此的1,3-位置的R30、R31、R32、R33、R34、R35和R36中的两个取代基一起形成具有5或6个碳原子的未取代或取代碳环,如环己烯基或环戊烯基,它们可以是未取代的或被一个或多个C1-4烷基和/或C1-4烷氧基取代,
p,q和r是0或1和Mk+是有机或无机阳离子和k是1-10,优选1-4的整数。
应该指出的是,根据US-B1-6 225 024,与在US-B1-6 225 024中所述的氧杂菁染料相反,在EP-A-833 314中所述的氧杂菁染料当用于DVD记录介质时,没有形成充分的记录和阅读性能,因为其具有低反射性和低调制度,并且没有满足就光牢度而言的要求,因为在长期照射的情况下发生了错误,具有减低的读出性能。
以下通式的氧杂菁染料是优选的:
其中R30、R31、R32、R33、R34、R35和R36,p,q和r,Mk+和k如以上所定义,R41和R41′彼此独立是氢原子,未取代或取代C1-12烷基,C5-7环烷基,C6-12芳基,C7-12芳烷基或杂环基团,
R42和R42′彼此独立是氢原子,氰基,基团C(O)OR46,CONR46R47,或C(O)R47,未取代或取代C1-12烷基,C5-7环烷基,C6-12芳基,C7-12芳烷基或杂环基团,R46和R47是未取代或取代的C1-12烷基,C5-7环烷基,C6-12芳基,C7-12芳烷基或杂环基团,或R46和R47与它们所键接的氮原子一起形成5或6元环,和
R43和R43′彼此独立是氢原子,羧酸基团或烷基。
特别优选的以下通式的氧杂菁染料:
其中Mk+是铵阳离子,如K-1,K-2,K-3,K-4,M-1,M-2,M-3或M-4,k是1-4,尤其1或2的整数,
R41和R41′彼此独立是氢原子,C1-4烷基,如甲基或乙基,或全氟-C1-4烷基,如三氟甲基,羟基-C1-4烷基,或插入一个或多个-O-的C1-8烷基,如CH2CH2CH2-O-CH(CH3)2,C6-10芳基,如苯基,或C7-12芳烷基,如苄基,
R42和R42′彼此独立是氢原子,氰基或羧酰胺基,
R43和R43′彼此独立是氢原子,羧酸基团或其盐或C1-4烷基,
R44和R44′彼此独立是氢原子,C1-4烷基,C6-12芳基或C7-12芳烷基,或
R44和R44′一起形成5元或6元环,如环己烯基或环戊烯基环,和
R45是氢原子,卤素原子,尤其氯原子,未取代或C1-4烷基或C1-4烷氧基取代的C6-12芳基,如苯基或对甲基苯基,或C7-12芳烷基,如苄基。
此外,以下通式的氧杂菁染料是优选的:
其中Ra、Rb、Ra′和Rb′彼此独立是氢原子,C1-8烷基,尤其C1-4烷基,羟基-C1-8烷基,C1-8链烯基,如-CH2-CH=CH2,未取代或C1-4烷基或C1-4烷氧基取代的C6-12芳基,如苯基,或C7-12芳烷基,如苄基。
R44和R44′彼此独立是氢原子,C1-4烷基,C6-12芳基或C7-12芳烷基,或
R44和R44′一起形成5元或6元环,如环己烯基或环戊烯基环,和
R45是氢原子,卤素原子,尤其氯原子,未取代或C1-4烷基或C1-4烷氧基取代的C6-12芳基,如苯基或对甲基苯基,或C7-12芳烷基,如苄基,
X,k和Mk+如前面所定义。
特别优选的是以下的化合物和组合物:
化合物 | R41 | R42 | R43 | (1/k)MK+ | 实施例 |
D-1 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | K-1 | 1 |
D-2 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | K-2 | 2 |
D-3 | H | CN | CH3 | K-1 | 3 |
D-4 | CH3 | CN | CH3 | K-1 | 4 |
D-5 | CH3 | CN | CH3 | K-2 | 5 |
D-6 | C2H5 | CN | CH3 | K-1 | 6 |
D-7 | C2H5 | CN | CH3 | K-2 | 7 |
D-8 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | M-1 | 8 |
D-9 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | M-2 | 9 |
D-10 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | M-3 | 10 |
D-11 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | M-4 | 11 |
D-12 | 苯基 | CN | CH3 | K-2 | 12 |
D-13 | C2H5 | C(O)NH2 | CH3 | K-2 | 13 |
D-14 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | K-3 | 14 |
D-15 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | K-2 | 15 |
D-16 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | K-1 | 16 |
D-17 | CH2CH2CH2-O-CH(CH3)2 | CN | CH3 | K-4 | 17 |
D-48 | H | CN | CH3 | K-3 | 48 |
D-49 | C2H5 | CN | CH3 | K-3 | 49 |
D-52 | C2H5 | H | CH3 | K-2 | 52 |
D-53 | H | H | COO- | K-2 | 53 |
D-54 | C2H5 | C(O)NH2 | CH3 | K-2 | 54 |
化合物 | R41 | R41′ | (1/k)MK+ | 实施例 |
D-20 | CH3 | C2H5 | K-2 | 18 |
D-7 | C2H5 | C2H5 | K-2 | 18 |
D-5 | CH3 | CH3 | K-2 | 18 |
D-21 | 苯基 | C2H5 | K-2 | 19 |
D-7 | C2H5 | C2H5 | K-2 | 19 |
D-12 | 苯基 | 苯基 | K-2 | 19 |
D-22 | 苯基 | CH2CH2CH2-O-CH(CH3)2 | K-2 | 20 |
D-15 | CH2CH2CH2-O-CH(CH3)2 | CH2CH2CH2-O-CH(CH3)2 | K-2 | 20 |
D-12 | 苯基 | 苯基 | K-2 | 20 |
D-23 | C2H5 | CH2CH2CH2-O-CH(CH3)2 | K-2 | 21 |
D-15 | CH2CH2CH2-O-CH(CH3)2 | CH2CH2CH2-O-CH(CH3)2 | K-2 | 21 |
D-7 | C2H5 | C2H5 | K-2 | 21 |
化合物 | Ra | Ra′ | Rb | Rb′ | (1/k)MK+ | λmax | ε |
D-54 | Ph | Ph | Ph | Ph | K-8 | 597.2 | 175936 |
D-55 | CH3 | CH3 | CH3 | CH3 | K-8 | 594.4 | 62550 |
D-56 | CH3 | CH3 | CH3 | CH3 | K-3 | 594.7 | 148970 |
D-57 | tBu | tBu | C2H5 | C2H5 | K-9 | - | - |
D-58 | CH3 | CH3 | CH3 | CH3 | K-9 | - | - |
D-59 | tBu | tBu | C2H5 | C2H5 | K-8 | 597.2 | 95732 |
D-60 | H | H | Ph | Ph | K-8 | 602.9 | 148327 |
D-61 | 1) | 1) | tBu | tBu | K-8 | - | - |
D-62 | 1) | 1) | 1) | 1) | K-8 | - | - |
D-63 | Ph | Ph | Ph | Ph | K-9 | 597.1 | - |
D-64 | 1) | 1) | H | H | K-8 | 593.4 | - |
D-65 | Ph | Ph | H | H | K-9 | 594.4 | 133022 |
D-66 | Ph | Ph | H | H | K-2 | 594.2 | 142542 |
D-67 | 1) | 1) | 1) | 1) | K-9 | - | - |
D-68 | Ph | n-Bu | n-Bu | Ph | K-8 | - | - |
D-69 | Ph | n-Bu | n-Bu | Ph | K-9 | - | - |
1)-CH2-CH=CH2.
上述氧杂菁能够根据在DE-A-2 012 050,DE-A-2 835 074,US-A-3681 345,US-A-4 968 593,US-A-6 225 024和EP-A-0 833 314中所述的方法或与之类似的方法制备。
代替单一的通式(II)的化合物,记录层还可以包括这些化合物例如与根据本发明的2、3、4、或5种氧杂菁染料的混合物。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常常能够导致溶解性增加和/或聚集的倾向性降低。在适当的场合,离子对化合物的混合物可以具有不同阴离子,不同的阳离子或不同的阴离子和不同的阳离子。
根据本发明使用的氧杂菁染料与通式(I)的金属配合物的结合具有其最大值位于540-640nm或低于450nm的窄吸收带。通式(I)的金属配合物的使用令人惊奇地导致了氧杂菁染料以固态聚集的倾向性相对弱,使得即使在固态下也保持有利的窄吸收曲线。
当用于光存储介质时,在吸收带的较长波长侧,固体薄膜形式的根据本发明使用的组合物具有在600-700nm范围达到2.0-3.0和在390-400nm范围超过1.9的峰值的高折光指数,使得能够获得具有高反射性以及在所需光谱区的高灵敏度和良好重放特性的介质。
用作施涂层的载体的基材有利地是半透明的(T≥10%),或优选透明的(T≥90%)。该载体一般具有0.01-10mm,优选0.1-5mm的厚度。
该记录层优选位于透明基材和反射层之间。记录层的厚度是10-1000nm,优选30-300nm,尤其60-120nm。记录层的吸收谱的最大吸收一般为0.1-1.0。层厚度更尤其根据在阅读波长下的未写状态和已写状态的各自折光指数来选择,从而使得在未写状态下获得相加干涉而在已写状态下获得相消干涉,或反之亦然。
反射层(其厚度可以是10-150nm)优选具有高反射率(R≥45%,尤其R≥60%)与低透明性(T≤10%)。在另一实施方案中,例如在具有多个记录层的介质中,反射层同样可以是半透明的,即可以具有比较高的透明性(例如T≥50%)和低反射性(例如R≤45%)。
取决于层结构,最上层,例如反射层或记录层有利地另外提供了具有一般0.1-1000μm,优选0.1-50μm和尤其0.5-15μm的厚度的保护层。如果需要,这种保护层能够还起施加于其上的第二基材层的粘合促进剂的作用,该第二基材层优选为0.1-5mm厚并由与载体基材同样的材料组成。
整个记录介质的反射率优选为至少15%,尤其至少40%(例如对于DVD-R的45%)。
根据本发明的记录层的主要特征是在激光二极管的所述波长范围的非常高的初始反射率,该反射率能够在特别高的灵敏度下进行调节;高折光指数;固态下的窄吸收带;在不同脉冲持续时间下写入宽度(script width)的良好均匀性;良好的光稳定性;和在非卤化溶剂,尤其醇中的良好溶解性。
应用根据本发明的组合物有利地获得了具有高折光指数的均匀、无定形和低散射记录层,以及吸收边缘即使在固态下也令人惊奇地特别陡峭。其它优点是在日光中和在低功率密度的激光辐射下的高光稳定性,同时在高功率密度的激光辐射下的高灵敏度,均匀的写入宽度,高对比度,以及良好的热稳定性和贮存稳定性。
在相对高的记录速度下,所得结果令人惊奇地优于早先已知的记录介质。相对于周围介质,标记被更准确地限定,没有发生热诱发的变形。在正常和非常高的记录速度下,误码率(BLER或PI Sim8)和标记长度(抖动性)的统计偏差都比较低,使得能够在大的速度范围内获得无误差记录和重放。这些优点能够在600-700nm(优选630-690nm)的整个范围内获得,但在640-680nm,尤其在650-670nm,更尤其在658±5nm下尤其显著。
适合的基材例如是玻璃,矿物,陶瓷,以及热固性或热塑性塑料。优选的载体是玻璃和均聚物或共聚物塑料。适合的塑料例如是热塑性聚碳酸酯,聚酰胺,聚酯,聚丙烯酸酯和聚甲基丙烯酸酯,聚氨酯,聚烯烃,聚氯乙烯,聚偏二氟乙烯,聚酰亚胺,热固性聚酯和环氧树脂。基材能够为纯形式,或还可以含有普通添加剂,例如作为记录层的光稳定剂的如在JP04/167239中所建议的UV吸收剂或染料。在后一种情况下,可以有利的是,加到载体基材中的染料具有相对于记录层的染料向短波移至少10nm,优选至少20nm的最大吸收。
基材有利地在600-700nm范围内的至少一部分是透明的,使得它可以透过写入或读出波长的入射光的至少90%。基材优选在涂层面具有凹槽深度为50-500nm,凹槽宽度为0.2-0.8μm和两匝之间的轨道间距为0.4-1.6μm,尤其凹槽深度为100-200nm,凹槽宽度为0.3μm和两匝之间的间距为0.6-0.8μm的螺旋导向槽。根据本发明的组合物因此特别有利地适用于具有目前常用的0.4μm的凹点宽度和0.74μm的轨道间距的DVD介质。
为了进一步增加稳定性,如果需要,还可以添加常用量的已知稳定剂,例如在JP04/025 493中作为光稳定剂描述的二硫醇镍。
记录层包括通式(II)的化合物或这些化合物的混合物,有利地其量足以对折光指数具有显著影响。这种量一般是至少30wt%,优选至少60wt%,尤其至少80wt%。
通式(I)的金属配合物的适合浓度一般为1-1000wt%,优选30-60wt%,基于通式(II)的氧杂菁化合物。
该记录介质可以包括常用添加剂,例如成膜剂,其它常用成分,例如其它发色团(例如在300-1000nm具有最大吸收的那些),UV吸收剂和/或其它稳定剂,猝灭剂,例如荧光猝灭剂,熔点减低剂和分解促进剂。
当该记录层包括其它发色团时,这些发色团一般可以是能够通过在记录过程中的激光辐射来分解或改性的任何染料,或者它们可以对激光辐射呈惰性。当其它发色团通过激光辐射来分解或改性时,这能够通过激光辐射的吸收来直接进行,或能够通过根据本发明的通式(I)或(II)的化合物的分解来间接诱发。
当使用光学性能尽可能符合氧杂菁染料光学性能的其它发色团时,在最长波长吸收侧范围的情况下应该优选如此。优选,其它发色团和氧杂菁染料的波长转化点相隔最多20nm,尤其最多10nm。在该情况下,其它发色团和氧杂菁染料应该在激光辐射方面表现相似的特性,以使其可以用作其它发色团已知记录剂,其作用被通式(I)或(II)的化合物协同增强。
当使用光学性能尽可能不同于通式(I)或(II)化合物的光学性能的其它发色团或着色稳定剂时,它们有利地具有相对于通式(I)或(II)的染料的向紫移或向红移的最大吸收。在该情况下,最大吸收相隔优选至少50nm,尤其至少100nm。它们的实例是相对于通式(I)或(II)的染料向紫移的UV吸收剂,或相对于通式(I)或(II)的染料向红移和具有例如位于NIR或IR范围的最大吸收的有色稳定剂。还可以添加其它染料用于彩色标记识别,彩色掩膜(“金刚石染料”)或增强记录层的美观。在这些情况下,其它发色团或有色稳定剂应该表现对光和激光辐射优选尽可能惰性的特性。
当发色团或有色稳定剂用于其它目的时,它们的量应该优选低,使得它们对在600-700nm范围的记录层的总吸收的贡献为至多20%,优选至多10%。在这种情况下,其它染料或稳定剂的量有利地至多50wt%,优选至多10wt%,基于记录层。
除了氧杂菁以外的能够在记录层中使用的其它发色团例如是花青和花青金属配合物盐(US-A-5 958 650),苯乙烯基化合物(US-A-6103 331),偶氮染料和偶氮金属配合物(JP-A-11/028865),酞菁染料(EP-A-232 427,EP-A-337 209,EP-A-373 643,EP-A-463 550,EP-A-492 508,EP-A-492 508,EP-A-509 423,EP-A-511 590,EP-A-513370,EP-A-514 799,EP-A-518 213,EP-A-519 419,EP-A-519 423,EP-A-575 816,EP-A-600 427,EP-A-676 751,EP-A-712 904,WO-98/14520,WO-00/09522,CH-693/01),卟啉类或氮杂卟啉类(EP-A-822 546,US-A-5 998 093),二吡咯亚甲基类(dipyrromethene)染料及其金属螯合物(EP-A-822 544,EP-A-903 733),呫吨类染料及其金属配合物盐(US-A-5 851 621)或四元酸(quadratic acid)化合物(EP-A-568 877),以及噁嗪类,二噁嗪类,二氮杂苯乙烯基类,甲类,蒽醌类或吩噻嗪类。
除了通式I的金属配合物以外,可以使用其它稳定剂或荧光猝灭剂,例如含氮或含硫的烯醇、酚、双酚、硫醇、双硫醇,或偶氮、偶氮次甲基或甲染料,例如Irgalan Bordeaux EL(CibaSpezialitatenchemie AG)或类似化合物,位阻酚类及其衍生物(在适当的场合也作为阴离子X-),例如Cibafast AO(CibaSpezialitatenchemie AG),羟苯基-三唑类,羟苯基三嗪类或其它UV吸收剂,例如Cibafast W或Cibafast P(CibaSpezialitatenchemie AG)或位阻胺类(TEMPO或HALS,还可以硝基氧的形式,或NOR-HALS,在适当的场合,也作为阴离子X-)的金属配合物。
许多这些结构例如可以从US-A-5 219 707,JP-A-06/199045,JP-A-07/76169或JP-A-07/262604中获知,它们的一些也与光记录介质有关。
除了包括通式(I)或(II)的化合物以外,本发明的记录介质可以另外包括盐,例如氯化铵,氯化十五烷基铵,氯化钠,硫酸钠,甲基磺酸钠或甲基硫酸钠,它们的离子例如可以来源于所用组分。如果存在的话,这些其它盐可以优选以至多20wt%的量存在,基于记录层的总重量。
适于反射层的反射材料尤其包括金属,它提供了用于记录和重放的激光辐射的良好反射,例如元素周期表的III、IV和V主族以及副族的金属。Al,In,Sn,Pb,Sb,Bi,Cu,Ag,Au,Zn,Cd,Hg,Sc,Y,La,Ti,Zr,Hf,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和Lu,以及它们的合金是特别适合的。特别优选的是铝、银、铜、金或它们的合金的反射层,这是因为它们的高反射性和易生产性。
适于保护层的材料主要地包括塑料,它们以薄层施加于载体上或直接或借助粘合层施加于最上层。有利地选择具有良好表面性能(可以进一步改性,例如进行书写)的机械和热稳定的塑料。该塑料可以是热固性塑料或热塑性塑料。优选的是生产特别简单和经济的辐射固化性(例如用UV辐射)保护层。已知有多种多样的辐射固化性材料。辐射固化性单体和低聚物的实例是二醇、三醇和四醇的丙烯酸酯和甲基丙烯酸酯,芳族四羧酸和在氨基的至少两个邻位具有C1-C4烷基的芳族二胺的聚酰亚胺,以及具有二烷基马来酰亚胺基,例如二甲基马来酰亚胺基的低聚物。
根据本发明的记录介质可以具有其它层,例如干涉层。还可以制造具有多个(例如两个)记录层的记录介质。这些材料的结构和用途对于本领域的技术人员来说是已知的。优选的是干涉层布置在记录层和反射层之间和/或在记录层和基材之间,并且如在EP-A-353 393中所述由TiO2,Si3N4,ZnS或硅酮树脂的介电材料组成。
根据本发明的记录介质能够通过本身已知的方法来生产,根据所用材料和它们的功用,可以使用各种涂布方法。
适合的涂布方法例如是浸渍,浇注,刷涂,刮涂和转涂,以及在高度真空下进行的蒸气沉积方法。例如当使用浇注方法时,一般使用在有机溶剂中的溶液。例如在EP-A-401 791中描述了适合的涂布方法和溶剂。
记录层优选通过用染料溶液的转涂法来施涂,已证明令人满意的溶剂尤其是醇,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-丁醇和它们的混合物。还能够使用醚类(二丁基醚),酮类(2,6-二甲基-4-庚酮,5-甲基-2-己酮)或饱和或不饱和烃类(甲苯,二甲苯),例如以混合物(例如二丁基醚/2,6-二甲基-4-庚酮)或混合组分的形式使用。
本发明因此还涉及生产光记录介质的方法,其中将通式(I)的化合物在非卤化有机溶剂中的溶液施涂于具有凹坑的基材上。该施涂优选通过转涂法进行。
金属反射层的施涂优选通过溅射法,真空蒸气沉积法或化学蒸气沉积法(CVD)来进行。溅射技术特别优选用于施涂金属反射层,这是因为对载体的高粘合力。这种技术是已知的,并描述在专题文献中(例如J.L.Vos sen和W.Kern,“Thin Film Processes”,AcademicaPress,1978)中。
根据本发明的记录介质的结构主要通过读出方法来控制;已知的操作原理包括测量透射,或优选反射的变化,但还已知测量荧光代替透射或反射。
当记录介质根据反射的变化来操作时,记录介质例如可以配置如下:透明载体/记录层(任选多层)/反射层和视需要而定的保护层(不必是透明的);或载体(不必是透明的)/反射层/记录层和视需要而定的透明保护层。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,或在适当的场合,从保护层侧入射。在两种情况下,光检波器位于光源的同侧。首先提及的记录介质的结构一般优选用于DVD-R,后来所述的结构(反结构)尤其理想地用于蓝-紫范围的记录系统(DVR;EP-A-822 546和EP-A-1 103 962)。
当记录介质根据光透射的改变的原理来操作时,例如可以考虑以下结构:透明载体/记录层(任选多层)和视需要而定的透明保护层。用于记录和读出的光能够从载体侧入射或从记录层侧入射,或在适当的场合,从保护层侧入射,光检波器在这种情况下总是位于反侧。
适合的激光器是具有600-700nm的波长的那些,例如具有602、612、633、635、647、650、670或680nm的波长的商购激光器,尤其半导体激光器,如具有尤其大约635、650或658nm的波长,具有用于蓝-紫范围的380-420nm,尤其405±5nm的波长的GaAsAl,InGaAIP或GaAs激光二极管。记录一般精确地通过根据标记长度调制激光器和将其辐射集中于记录层上来进行。
根据本发明的方法使得可以极大的可靠性和稳定性存储信息,以非常良好的机械和热稳定性,高光稳定性以及分明的凹点边界区为特征。特殊优点包括高对比度,低抖动性和令人惊奇的高信号/噪音比率,使得获得了无问题读出。
如在“CD-Player und R-DAT Recorder”(Claus Biaesch-Wiepke,Vogel Buchverlag,Wurzburg 1992)中所述,信息的读出根据本身已知的方法通过记录使用激光辐射的吸收或反射的变化来进行。
根据本发明的含信息的介质尤其是WORM类的光信息材料。它例如能够用作可播放DVD(数字化通用光盘),用作计算机的存储材料,或用作标识和安全卡,或用于生产衍射光学元件,例如全息照片。
本发明因此还涉及信息的光记录、存储和重放的方法,其中使用根据本发明的记录介质。该记录和重放有利地在600-700nm,或低于450nm的波长范围进行。
根据本发明的组合物适合于生产对于各种应用如凹版/橡胶版轮转印刷,平张纸胶印和金属片印刷具有优异应用性能的印刷油墨,以及用于生产具有有利的窄吸收曲线的滤色器。本发明因此还涉及包括根据本发明的组合物的印刷油墨或滤色器(滤光器),其中氧杂菁是特别优选的,其中Mk+是氢阳离子。本发明尤其涉及包括载体层和滤光层的滤光器,其中滤光层包括根据本发明的组合物。滤光器本身例如能够用于电光系统如TV屏幕,液晶显示器,电荷耦合设备,等离子体显示器或电致发光显示器等。
滤光层含有1-75wt%,优选5-50wt%,最优选25-40wt%的分散于高分子量有机材料中的根据本发明的组合物,基于滤光层的总重量。
载体层优选基本无色(T≥95%,在400-700nm的整个可见区范围内)。关于生产滤色器和在生产滤色器中使用的高分子量材料的进一步细节例如描述在High-Technology Applications of OrganicColorants,Peter Gregory,Plenum Press,New York and London1991,p.15-25,WO 01/04215和WO 02/10288中。具有在560-620nm范围的最大吸收的滤光器例如适合作为用于等离子体显示器的极窄带滤光器(例如参看EP-A-1 124 144)。
本发明的印刷油墨适当地含有0.01-40wt%,优选1-25wt%,特别优选5-10wt%的浓度的本发明的组合物,基于印刷油墨的总重量,例如可用于在纸张、板、金属、木材、皮革、塑料或纺织品上的照相凹版印刷,橡胶版轮转印刷,丝网印刷,胶版印刷,或连续或滴状喷墨式印刷,或者按照属于常识的配方用于专业应用,例如出版、包装或货运,后勤,广告,保密印刷,或用于圆珠笔,毡尖笔,纤维尖笔,打印台,墨带或喷墨印刷机墨盒的办公领域。
以下的实施例举例说明本发明。除非另有规定,百分数和份数分别是重量百分数和重量份。除非另有规定,λmax和ε在DMF(二甲基甲酰胺)中测定。
在下文的实施例中,Primene 81R的铵盐(Rohm & Haas Company,C12-14胺异构体的混合物)以理想化形式示出:
实施例1:
在惰性气体气氛下,将100份的N-(3-异丙氧基-丙基)-3-氰基-4-甲基-6-羟基-2-吡啶酮与3 3份的1,1,3,3-四甲氧基-丙烷在120份的吡啶中在110℃下搅拌2小时。在冷却到室温之后,反应产物沉淀出来,再利用吸滤分离出固体材料,依次用25份吡啶和200份水洗涤。将以下示出的结构式的目标化合物在90℃和真空(120毫巴)下干燥(收率:63%)。在70℃下,将53份粗产物在300份甲醇中搅拌10分钟。在冷却之后,利用吸滤分离残留物,用100份的甲醇洗涤和在90℃和真空下干燥(收率:66%)。
λmax=603nm(ε:148 469),在DMF中测定
实施例2:
在室温下将在实施例1中获得的57份的产物在300份甲醇中搅拌,再加入11份的Primene 81R(Rohm & Haas Company,C12-14胺异构体的混合物)。该溶液用活性炭处理,浓缩滤液。残留物在90℃下干燥,获得了以下所示结构式的蓝色产物(收率:56%)。
λmax=603.5nm(ε:199 536),在DMF中测定
以与实施例1和2所述的方法类似的方法可获得以下所示的化合物D-3到D-17:
实施例 | 化合物 | R41 | R42 | R43 | (1/k)MK+ | λmax | ε |
3 | D-3 | H | CN | CH3 | K-1 | 603.5 | 198 600 |
4 | D-4 | CH3 | CN | CH3 | K-1 | 601.5 | 116 500 |
5 | D-5 | CH3 | CN | CH3 | K-2 | 601.8 | 200 300 |
6 | D-6 | C2H5 | CN | CH3 | K-1 | 602.6 | 187 500 |
7 | D-7 | C2H5 | CN | CH3 | K-2 | 603 | 194 300 |
8 | D-8 | 1) | CN | CH3 | M-1 | ||
9 | D-9 | 1) | CN | CH3 | M-2 | ||
10 | D-10 | 1) | CN | CH3 | M-3 | ||
11 | D-11 | 1) | CN | CH3 | M-4 | ||
12 | D-122) | 苯基 | CN | CH3 | K-2 | 605.2 | 138 200 |
13 | D-13 | C2H5 | C(O)NH2 | CH3 | K-2 | 589 | |
14 | D-142) | 1) | CN | CH3 | K-3 | 602.9 | 176 000 |
15 | D-15 | 1) | CN | CH3 | K-2 | 603.5 | 199 500 |
16 | D-16 | 1) | CN | CH3 | K-1 | ||
17 | D-17 | 1) | CN | CH3 | K-4 | ||
48 | D-482) | H | CN | CH3 | K-3 | 603.3 | 214 200 |
49 | D-492) | C2H5 | CN | CH3 | K-3 | 602.7 | 217 600 |
52 | D-523) | C2H5 | H | CH3 | K-2 | ||
53 | D-533) | H | H | COO- | K-2 | ||
54 | D-543) | C2H5 | C(O)NH2 | CH3 | K-2 |
1)CH2CH2CH2-O-CH(CH3)2
2)这些化合物根据在实施例12中所述的方法,或与之类似的方法获得。
3)这些化合物根据在实施例53中所述的方法,或与之类似的方法获得。
实施例12:
将22.62g(0.1mol)的N-苯基-3-氰基-4-甲基-6-羟基-2-吡啶酮与8.21g(0.05mol)的四甲氧基丙烷,9.27g(0.05mol)的Primene81R一起在200ml正丁醇中在回流下煮沸18小时。趁热过滤该悬浮液,然后冷却。用抽吸过滤出沉淀出来的蓝色产物,用乙醇洗涤以及在80℃和真空(120毫巴)下干燥。
与在实施例1、2和12中所述方法类似地获得了化合物D-20到D-31,其中使用比率为50∶50的两种不同起始原料的混合物代替单一的N-(3-异丙氧基-丙基)-3-氰基-4-甲基-6-羟基-2-吡啶酮起始原料:
实施例 | 化合物 | R41 | R41′ | (1/k)MK+ |
18 | D-20 | CH3 | C2H5 | K-21) |
18 | D-7 | C2H5 | C2H5 | K-21) |
18 | D-5 | CH3 | CH3 | K-21) |
19 | D-21 | 苯基 | C2H5 | K-22) |
19 | D-7 | C2H5 | C2H5 | K-22) |
19 | D-12 | 苯基 | 苯基 | K-22) |
20 | D-22 | 苯基 | CH2CH2CH2-O-CH(CH3)2 | K-23) |
20 | D-15 | CH2CH2CH2-O-CH(CH3)2 | CH2CH2CH2-O-CH(CH3)2 | K-23) |
20 | D-12 | 苯基 | 苯基 | K-23) |
21 | D-23 | C2H5 | CH2CH2CH2-O-CH(CH3)2 | K-24) |
21 | D-15 | CH2CH2CH2-O-CH(CH3)2 | CH2CH2CH2-O-CH(CH3)2 | K-24) |
21 | D-7 | C2H5 | C2H5 | K-24) |
1)在实施例18中获得的D20∶D7∶D5的混合物表现了601.9的λmax。
2)在实施例19中获得的D21∶D7∶D12的混合物表现了603.3的λmax。
3)在实施例20中获得的D22∶D15∶D12的混合物表现了603.9的λmax。
4)在实施例21中获得的D23∶D15∶D7的混合物表现了602.8的λmax。
实施例22:
D-40(λmax=492.6nm;ε:151 500)
实施例23:
D-41(λmax=610nm(乙腈))
实施例24:
D-42(λmax=610nm(乙腈))
实施例25:
在室温下,将246mg以下所示的氧杂菁染料的吡啶鎓盐(
D-16)溶解在40ml的丙酮中。将256mg的以下所示花青染料的高氯酸盐溶解在25ml丙酮中,再滴加到氧杂菁染料的溶液中。将该溶液在室温下搅拌半小时,过滤和通过蒸发来浓缩。将残留物溶解在18ml的二氯甲烷中,用15ml的水洗涤三次,再通过蒸发来浓缩,获得了466.1mg的以下所示的离子对。
D-50(λmax=596nm;ε:236 200(乙醇))
实施例26:
D-51
实施例27:
在室温下将100mg的在实施例25中获得的D-50溶解在25ml的甲醇中。在45-50℃下将30.6mg的M-5溶解在80ml的甲醇中,再加入到D-50的溶液中。将该溶液在室温下搅拌半小时,过滤,再通过蒸发来浓缩。将残留物溶解在4ml去离子水中,用超声处理半小时,过滤,再干燥。获得了130.1mg的D-50和M-5的混合物。
在30-40℃下,将61.5mg以下所示的氧杂菁染料的吡啶鎓盐(
D-16)溶解在25ml的乙醇中。将58mg的以下所示花青染料的碘盐溶解在20ml的乙醇中,再滴加到氧杂菁染料的溶液中。将该溶液在室温下搅拌半小时,过滤和通过蒸发来浓缩。将残留物溶解在4ml去离子水中,用超声处理半小时,过滤,再干燥。获得了102.1mg的以下所示的离子对。
实施例28:
将3份乙二胺在20份乙醇中的溶液加入到12份水杨醛在100份乙醇中的溶液中,加热所得混合物,直到获得溶液为止。添加9份的在水中的乙酸铜,获得了灰色沉淀。冷却该混合物,过滤,获得了下式的绿色固体:
实施例53
将15.4g(0.1mol)柠嗪酸与8.16g(0.05mol)四甲氧基丙烷和15ml盐酸(浓)一起悬浮在100ml 2-乙氧基乙醇中,再在回流下煮沸17小时。在冷却之后,在抽吸下过滤出沉淀,用甲醇洗涤,再于80℃和真空(120毫巴)下干燥。获得了7.37g的蓝色产物,使用Primene81R将它转化为D-53。
与实施例28中所述的方法类似地可获得以下在表2中所示的配合物。
表2
实施例 | 化合物 | R51 | R52 | R53 | R54 | R61 | R62 | R63 | R64 | R1 | R4 | R2 | R3 | R2 | R3 | Me |
29 | M-1Y- | H | H | H | H | H | H | +N(CH3)3Y- | H | CH3 | H | H | CH3 | H | CH3 | Cu |
30 | M-22Y- | H | H | +N(CH3)3Y- | H | H | H | +N(CH3)3Y- | H | H | H | H | H | H | H | Cu |
31 | M-32Y- | H | H | +N(CH3)3Y- | H | H | H | +N(CH3)3Y- | H | H | H | 1) | 1) | H | H | Cu |
32 | M-42Y- | H | H | OCH2CH2-+N(CH3)3Y- | H | H | H | OCH2CH2-+N(CH3)3Y- | H | H | H | H | H | H | H | Cu |
28 | M-5 | H | H | H | H | H | H | H | H | H | H | H | H | H | H | Cu |
33 | M-6 | H | H | H | CH3 | H | H | H | CH3 | H | H | H | H | H | H | Cu |
34 | M-7 | H | H | H | OCH3 | H | H | H | OCH3 | H | H | H | H | H | H | Cu |
35 | M-8 | H | H | OC12H25 | H | H | H | OC12H25 | H | H | H | H | H | H | H | Cu |
36 | M-9 | H | H | OC2H4OCH3 | H | H | H | OC2H4OCH3 | H | H | H | H | H | H | H | Cu |
37 | M-10 | H | H | OC2H4OC2H4OC2H5 | H | H | H | OC2H4OC2H4OC2H5 | H | H | H | H | H | H | H | Cu |
38 | M-11 | H | H | O-叔-C4H9 | H | H | H | O-叔-C4H9 | H | H | H | H | H | H | H | Cu |
39 | M-12 | H | H | H | H | H | H | H | H | C2H5 | C2H5 | H | H | H | H | Cu |
40 | M-13 | CH3 | H | H | CH3 | CH3 | H | H | CH3 | H | H | H | H | H | H | Cu |
41 | M-14 | H | H | H | H | H | H | H | H | H | H | 1) | 1) | H | H | Cu |
42 | M-15 | H | H | H | H | H | H | H | H | H | H | 1) | 1) | H | H | Co |
43 | M-16 | H | t-C4H9 | H | tert-C4H9 | H | tert-C4H9 | H | tert-C4H9 | H | H | 1) | 1) | H | H | Ni |
44 | M-17 | H | H | H | H | H | H | H | H | H | H | 1) | 1) | H | H | Ni |
45 | M-18 | H | H | N(CH3)2 | H | H | H | N(CH3)2 | H | H | H | 1) | 1) | H | H | Ni |
46 | M-19 | H | H | OP(O)(OC2H5)2 | H | H | H | OP(O)(OC2H5)2 | H | H | H | H | H | H | H | Cu |
47 | M-20 | H | SO3 -Y1+ | H | H | H | SO3 -Y1+ | H | H | H | H | H | H | H | H | Cu |
48 | M-21 | H | H | O-叔-C4H9 | H | H | H | O-叔-C4H9 | H | H | H | 2) | 2) | CN | CN | Ni |
49 | M-22 | H | H | H | H | H | H | H | H | H | H | 3) | 3) | 3) | 3) | Ni |
50 | M-23 | 4) | 4) | H | 5) | 4) | 4) | H | 5) | H | H | 2) | 2) | CN | CN | Ni |
1)R2和R3一起形成环己烷环;2)R2和R3一起形成双键;3)R2,R2,R3和R3′一起形成苯环;4)R51和R52一起,和/或R61和R62一起形成苯环;5)-C(O)OCH2CH2OCH2CH2OH.
实施例54
将2.80g N,N-二苯基巴比土酸和1.43g N-[5-(苯基氨基)-2,4-戊二烯叉基]苯胺的单盐酸盐溶解在40ml丙酮中,在冰浴中冷却到5℃。然后,添加3ml的三乙胺,再将混合物搅拌3小时。通过蒸发浓缩该紫色溶液,残留物用二乙醚和水洗涤,再于45℃下干燥。获得了3.14g的以下所示的离子对D-54。
与实施例54中所述的方法类似地可获得以下所示的化合物D-55到D-70:
D-70(λmax=552nm)
实施例 | 化合物 | Ra | Ra | Rb | Rb′ | (1/k)Mk+ | λmax | ε |
54 | D-54 | Ph | Ph | Ph | Ph | K-8 | 597.2 | 175936 |
55 | D-55 | CH3 | CH3 | CH3 | CH3 | K-8 | 594.4 | 62550 |
56 | D-56 | CH3 | CH3 | CH3 | CH3 | K-3 | 594.7 | 148970 |
57 | D-57 | tBu | tBu | C2H5 | C2H5 | K-9 | - | - |
58 | D-58 | CH3 | CH3 | CH3 | CH3 | K-9 | - | - |
59 | D-59 | tBu | tBu | C2H5 | C2H5 | K-8 | 597.2 | 95732 |
60 | D-60 | H | H | Ph | Ph | K-8 | 602.9 | 148327 |
61 | D-61 | 11 | 1) | tBu | tBu | K-8 | - | - |
62 | D-62 | 1) | 1) | 1) | 1) | K-8 | - | - |
63 | D-63 | Ph | Ph | Ph | Ph | K-9 | 597.1 | - |
64 | D-64 | 1) | 1) | H | H | K-8 | 593.4 | - |
65 | D-65 | Ph | Ph | H | H | K-9 | 594.4 | 133022 |
66 | D-66 | Ph | Ph | H | H | K-2 | 594.2 | 142542 |
67 | D-67 | 1) | 1) | 1) | 1) | K-9 | - | - |
68 | D-68 | Ph | n-Bu | n-Bu | Ph | K-8 | - | - |
69 | D-69 | Ph | n-Bu | n-Bu | Ph | K-9 | - | - |
1)-CH2-CH=CH2.
应用实施例1
将1.5wt%的M-5和根据实施例D-2的等摩尔混合物溶解在1-丙醇中,该溶液用具有0.2μm的孔径的Teflon过滤器过滤,再通过转涂法以1000rev/min施涂于0.6mm厚、直径120mm的有槽聚碳酸酯光盘(沟槽深度170nm,沟槽宽度350nm,轨道间距0.74μm)的表面上。通过增加转速甩出过量溶液。在蒸发溶剂之后,染料以均匀、无定形固体层的形式保留下来。在70℃的循环空气烘箱内干燥(10分钟)之后,固体层显示了在623nm下0.50的吸收率。在真空涂布装置(TwisterTM,Balzers Unaxis)中,然后通过雾化法将70nm厚银涂层施涂于该记录层上。然后,利用转涂法在其上施涂6μm厚UV固化性光敏聚合物(650-020,DSM)的保护层。该记录载体显示了在658nm下的48%的反射率。
使用工业试验装置(DVDT-RTM,Expert Magnetics),用波长658nm的激光二极管以3.5mm/sec的速度和9.5mW的激光功率将标记写入到活性层上。然后使用相同的试验装置测定动态参数,其中获得了良好的测量值:DTC抖动性=9.0%;R14H=4 7%;114/14H=0.6。
应用实施例2
将0.2wt%的根据实施例7的化合物D-7溶解在增塑剂中,在一种情况下添加等摩尔的实施例28的化合物M-5,在另一种情况下不添加等摩尔的实施例28的化合物M-5,然后在160℃下引入到PVC膜上。使用商购UV/VIS分光光度计(Carey)测量两种薄膜的吸收谱。在包括聚集形式的滤波器的情况下(没有添加),在580nm下测定的半值宽度为65nm,在非聚集形式的情况下,在613nm下的半值宽度为24.5nm。
应用实施例3
在100ml玻璃容器内,在23℃下,用Dispermat将83.3g锆石瓷珠,2.8g的M-5和D-2的等摩尔混合物,0.28g的Solsperse5000,4.10g的Disperbyk161(分散剂/BYK Chemie:携带具有颜料亲合力的基团的高分子量嵌段共聚物在1∶6乙酸正丁酯/乙酸1-甲氧基-2-丙酯中的30%溶液)和14.62g丙二醇单甲醚乙酸酯(MPA,CAS Reg.No.108-65-6)在1000rpm下搅拌10分钟,在3000rpm下搅拌180分钟。在室温下添加4.01g的丙烯酸系聚合物粘结剂(在MPA中的35%),之后,继续在3000rpm下搅拌30分钟。在分离出珠粒之后,分散体用等量的MPA稀释。玻璃基材(Corning Type 1737-F)在漆料旋涂装置中用该分散体涂敷,再在1000rpm下旋转30秒钟。涂层的干燥在电热板上在100℃下进行2分钟和在200℃下进行5分钟。所得明亮的紫/蓝色薄膜的涂层厚度是0.4μm。
应用实施例4
将0.01mol的氧杂菁D-71溶解在50ml三氟乙酸(TFA)中。将0.01mol M-5也溶解在TFA中。用猛烈搅拌混合该两种溶液。过滤出所得暗紫色沉淀,用水洗涤至中性,干燥,再筛分。
在23℃下,在含有83.3g的锆石陶瓷珠粒,2.8g的以上产物(D-71/M-5),0.28g的Solsperse5000,4.10g的Disperbyk161(分散剂/BYK Chemie:携带具有颜料亲合力的基团的高分子量嵌段共聚物在1∶6乙酸正丁酯/乙酸1-甲氧基-2-丙酯中的30%溶液)和14.62g丙二醇单甲醚乙酸酯(MPA,CAS Reg.No.108-65-6)的100ml玻璃容器中,用Dispermat在1000rpm下搅拌10分钟,在3000rpm下搅拌180分钟。在室温下添加4.01g的丙烯酸系聚合物粘结剂(在MPA中的35%),之后,继续在3000rpm下搅拌30分钟。在分离出珠粒之后,分散体用等量的MPA稀释。玻璃基材(Corning Type 1737-F)在漆料旋涂装置中用该分散体涂敷,再在1000rpm下旋转30秒钟。涂层的干燥在电热板上在100℃下进行2分钟和在200℃下进行5分钟。所得涂层厚度是0.4μm。获得了明亮的紫/蓝色薄膜。
如果使用0.8-2.0gε-CuPc(Atlantic Blue)和0.8-2.0g的产物(D-71/M-5)代替2.8g的产物(D-71/M-5),获得了明亮的蓝色薄膜。用更多的氧杂菁,颜色会变得更紫。
如果使用氧杂菁D-72或D-73代替氧杂菁D-71,获得了类似的结果。
Claims (15)
1、含有至少一种氧杂菁染料和至少一种以下通式的金属配合物的组合物:
其中Me是7、8、9、10、11或12,优选9、10或11副族的过渡金属,
D1和D2彼此独立是碳环或杂环或碳环体系或杂环体系,它们可以是未取代的或被一个或多个基团R5和R6取代,
R5和R6是卤素原子,如氟,氯或溴,氨基,烷基氨基,二烷基氨基,硝基,氰基,羟基,未取代或取代烷基,未取代或取代羟烷基,未取代或取代烷氧基,插入一个或多个-O-或-S-和可以未取代或取代的烷基,酰基,苯基,酯基,如膦酸酯,磷酸酯或羧酸酯基,羧酰胺基,磺酰胺基,铵基,羧酸基,磺酸基,膦酸基或磷酸基或它们的盐,
R1和R4彼此独立是氢原子,或未取代或取代烷基,芳基或芳烷基,
R2,R2′,R3和R3′彼此独立是氢原子,氰基,未取代或取代烷基,烷氧基,芳基或芳烷基,酯基,羧酰胺基,磺酰胺基,三烷基铵基,羧酸基、磺酸基、膦酸基或磷酸基或它们的盐,或
R2和R3一起,或R2′和R3′一起形成双键,环烷基环或杂环,或
R2、R2′、R3和3′一起形成芳族碳环或杂环,
R2和R2′一起,和/或R3和R3′一起各对彼此独立形成羰基或硫代羰基,
R7,R7′,R8和R8′彼此独立是氢原子或未取代或取代烷基,芳基或芳烷基,或
R7和R7′一起,和/或R8和R8′一起各对彼此独立形成羰基或硫代羰基。
2、根据权利要求1的组合物,其中氧杂菁染料是以下通式的染料:
或
其中A1、A2、B1和B2在各种情况下是取代基;Y1和Z1在各种情况下是形成碳环或杂环所必需的原子组;E和G在各种情况下是形成具有共轭双键的链所必需的原子组;X1是=O,=NR9,或=C(CN)2,R9是取代基;X2是-O,-NR9或-C(CN)2,R9是取代基;L是次甲基,它可以是取代的,或利用它可以完成聚甲炔的基团,可以将3、5或7个次甲基连接,以便形成具有共轭双键的链,该链可以是取代的;Mk+是有机或无机阳离子,通式(I-1)或(I-2)的金属配合物还可以是该阳离子,前提是它携带一个或多个正电荷;x和y是0或1,k是1-10的整数。
3、根据权利要求1或权利要求2的组合物,其中Mk+是铵阳离子或阳离子染料。
4、根据权利要求3的组合物,其中阳离子染料在550-620nm和/或低于450nm的范围内具有最大吸收。
5、根据权利要求1-3的任一项的组合物,其中氧杂菁染料具有以下通式:
其中Mk+是铵阳离子, k是1-4,尤其1或2的整数,
Ra、Rb、Ra′和Rb′彼此独立是氢原子,C1-8烷基,尤其C1-4烷基,羟基-C1-8烷基,C1-8链烯基,如-CH2-CH=CH2,未取代或C1-4烷基或C1-4烷氧基取代的C6-12芳基,如苯基,或C7-12芳烷基,如苄基,
R41和R41′彼此独立是氢原子,C1-4烷基,如甲基或乙基,或全氟-C1-4烷基,如三氟甲基,羟基-C1-4烷基,或插入一个或多个-O-的C1-8烷基,如CH2CH2CH2-O-CH(CH3)2,C6-10芳基,如苯基,或C7-12芳烷基,如苄基,
R42和R42′彼此独立是氢原子,氰基或羧酰胺基,
R43和R43′彼此独立是氢原子,羧酸基团或其盐或C1-4烷基,
R44和R44′彼此独立是氢原子,C1-4烷基,C6-12芳基或C7-12芳烷基,或
R44和R44′一起形成5元或6元环,如环己烯基或环戊烯基环,和
R45是氢原子,卤素原子,尤其氯原子,未取代或C1-4烷基或C1-4烷氧基取代的C6-12芳基,如苯基或对甲基苯基,或C7-12芳烷基,如苄基。
6、根据权利要求5的组合物,其中Mk+选自以下阳离子:
其中R10、R10′和R10′′彼此独立是氢原子,未取代或例如被1-3个C1-4烷基取代的C3-24环烷基,例如环己基或3,3,5-三甲基环己基,或松香胺D,或直链或支化C1-24烷基,R11、R12、R13和R14是氢原子,直链或支化C1-36烷基,优选C1-16烷基,它们可以是未取代或取代的,直链或支化羟基-C1-36烷基,尤其羟基-C1-8烷基,C6-24芳基,尤其C6-10芳基,或C7-24芳烷基,尤其C7-12芳烷基,或基团R11、R12、R13和R14中的两个与它们所键接的氮原子一起形成5或6元杂环,如吡咯烷基,哌啶子基或吗啉基;或
其中R67和R68彼此独立是取代基,R65和R66彼此独立是取代或未取代的烷基,取代或未取代的链烯基,取代或未取代炔基,取代或未取代芳烷基,取代或未取代芳基,或者取代或未取代杂环基,成对的R67和R68,R67和R65,R68和R66,以及R65和R66可以连接成环,以及s和t彼此独立是0或1-4的整数,前提是当s和t具有2或2以上的值时,基团R67和R68可以是相同或不同的;
或通式:
其中R69是直链或支化C1-8烷基,尤其甲基,乙基,丙基,丁基,或叔丁基,它们可以是未取代或取代的,例如被氰基,卤素原子或被C1-4烷氧基取代;
其中R201、R202和R203彼此独立是氢原子,直链或支化C1-36烷基,优选C1-16烷基,它们可以是未取代或取代的,羟基-C1-36烷基,尤其羟基-C1-8烷基,它们可以是未取代的或被一个或多个C1-4烷基和/或C1-4烷氧基取代,C3-24环烷基,尤其C5-7环烷基,C6-24芳基,尤其C6-10芳基,或C7-24芳烷基,尤其C7-12芳烷基,或者基团R201、R202和R203中的两个与它们所键接的氮一起形成5或6元杂环,R204是氢原子,C1-4烷基或C1-4烷氧基,u和v是1-3的整数,u和v的和是3、4或5,和
X是二价连接基团,例如未取代或被一个或多个C1-4烷基和/或C1-4烷氧基取代的C1-8亚烷基,或基团:
或
其中R204如上文所定义,Ar是未取代或被一个或多个C1-4烷基和/或C1-4烷氧基取代的C6-10芳基,Cy是未取代或被一个或多个C1-4烷基和/或C1-4烷氧基取代的C5-7环烷基,和t是0-4的整数;
或以下通式的金属配合物:
其中
Me是Cu,Ni或Co;
R51、R52、R53、R54、R61、R62、R63和R64是氢原子,氯原子,溴原子,羟基,可以是未取代或被二或三烷基铵基取代的C1-8烷基,可以是未取代或被二或三烷基铵基取代的C1-16烷氧基,可以插入一个或多个-O-或-S-和可以是未取代或被二或三烷基铵基取代的C1-8烷基;酯基,如膦酸酯、磷酸酯和羧酸酯基,羧酰胺基,磺酰胺基或二或三烷基铵基;
R1和R4彼此独立是氢原子或C1-8烷基;R2,R2′,R3和R3′是氢原子,氰基或C1-8烷基,或者成对的基团R2和R2′一起,以及R3和R3′一起形成环己烷环,基团R51、R52、R53、R54、R61、R62、R63和R64的至少一个是二或三烷基铵基或被二或三烷基铵基取代;
R7,R7′,R8和R8′彼此独立是氢原子或未取代或取代C1-8烷基,苯基或苄基,或
R7和R7′一起,和/或R8和R8′一起各对彼此独立形成羰基或硫代羰基。
7、一种包括基材和至少一个记录层的光记录介质,其中该记录层包括根据权利要求1-6的任一项的组合物。
8、根据权利要求1-6的任一项的组合物用于生产光记录介质、滤色器(滤光器)和印刷油墨的用途。
9、一种生产光记录介质的方法,其中将根据权利要求1-6的任一项的组合物在非卤化溶剂中的溶液施涂于具有凹坑的基材上。
10、根据权利要求2的通式(II-1)或(II-2)的氧杂菁染料,其中Mk+是阳离子染料。
11、根据权利要求9的方法,其中有机溶剂是醇。
12、根据权利要求10的氧杂菁染料在光信息存储中的用途。
13、通式(I-1)的金属配合物在光信息存储中的用途,其中Me,D1和D2,R5和R6,R1和R4如权利要求1所定义,R2和R3形成双键,以及R2′和R3′是氰基。
14、一种包括载体层和滤光层的滤光器,其中滤光层包括根据权利要求1-6的任一项的本发明的组合物。
15、一种包括根据权利要求1-6的任一项的本发明的组合物的印刷油墨。
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CN109643081A (zh) * | 2016-06-03 | 2019-04-16 | 史丹斯伯格公司 | 金属化包括表面起伏结构的光学元件的方法 |
CN107168012A (zh) * | 2017-07-11 | 2017-09-15 | 深圳市华星光电技术有限公司 | 一种彩色光刻胶及其制备方法 |
CN107759491A (zh) * | 2017-11-02 | 2018-03-06 | 云南大学 | 席夫碱铜(ii)抗癌配合物及其制备方法和应用 |
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DE60204981T2 (de) | 2006-04-20 |
US20050003135A1 (en) | 2005-01-06 |
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AU2002351829A2 (en) | 2003-05-26 |
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