JP5631008B2 - 透明着色剤及び着色剤組成物、及びそれらの使用 - Google Patents
透明着色剤及び着色剤組成物、及びそれらの使用 Download PDFInfo
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- JP5631008B2 JP5631008B2 JP2009550690A JP2009550690A JP5631008B2 JP 5631008 B2 JP5631008 B2 JP 5631008B2 JP 2009550690 A JP2009550690 A JP 2009550690A JP 2009550690 A JP2009550690 A JP 2009550690A JP 5631008 B2 JP5631008 B2 JP 5631008B2
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- Prior art keywords
- meth
- alkyl
- acrylate
- formula
- phenyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 239000003086 colorant Substances 0.000 title abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 239000000049 pigment Substances 0.000 claims abstract description 48
- 239000002245 particle Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 229920002120 photoresistant polymer Polymers 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 13
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 239000011368 organic material Substances 0.000 claims description 6
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 claims description 2
- -1 2-phenylthio-substituted anthraquinone Chemical class 0.000 description 93
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 36
- 229920001577 copolymer Polymers 0.000 description 32
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 29
- 238000000034 method Methods 0.000 description 27
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 26
- 239000010410 layer Substances 0.000 description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 24
- 239000011230 binding agent Substances 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 16
- 229910052736 halogen Inorganic materials 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000000976 ink Substances 0.000 description 11
- 238000007639 printing Methods 0.000 description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000001624 naphthyl group Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 229910004013 NO 2 Inorganic materials 0.000 description 7
- 150000004056 anthraquinones Chemical class 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 6
- 239000001000 anthraquinone dye Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000002491 polymer binding agent Substances 0.000 description 5
- 230000007261 regionalization Effects 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Chemical class 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 229940063557 methacrylate Drugs 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
- FPRGJFFNVANESG-UHFFFAOYSA-N 1-phenylsulfanylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1SC1=CC=CC=C1 FPRGJFFNVANESG-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- QIUYUDPFQAVSOB-UHFFFAOYSA-N 3-phenyl-10-sulfanylideneanthracen-9-one Chemical compound C=1C=C2C(=O)C3=CC=CC=C3C(=S)C2=CC=1C1=CC=CC=C1 QIUYUDPFQAVSOB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
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- 239000001056 green pigment Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229920005596 polymer binder Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
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- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 2
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
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- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
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- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
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- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- DRHLRMQUFBARRH-UHFFFAOYSA-N n-(2-methylprop-2-enoyl)benzamide Chemical compound CC(=C)C(=O)NC(=O)C1=CC=CC=C1 DRHLRMQUFBARRH-UHFFFAOYSA-N 0.000 description 1
- GRKWKHMVNVMROH-UHFFFAOYSA-N n-(2-methylprop-2-enoyl)butanamide Chemical compound CCCC(=O)NC(=O)C(C)=C GRKWKHMVNVMROH-UHFFFAOYSA-N 0.000 description 1
- ZGUZDOKYZZUQAI-UHFFFAOYSA-N n-(2-methylprop-2-enoyl)decanamide Chemical compound CCCCCCCCCC(=O)NC(=O)C(C)=C ZGUZDOKYZZUQAI-UHFFFAOYSA-N 0.000 description 1
- FIQHOLCVUUGNRZ-UHFFFAOYSA-N n-(2-methylprop-2-enoyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NC(=O)C(C)=C FIQHOLCVUUGNRZ-UHFFFAOYSA-N 0.000 description 1
- ZPIDGYYDWGHQIS-UHFFFAOYSA-N n-(2-methylprop-2-enoyl)naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)NC(=O)C(=C)C)=CC=CC2=C1 ZPIDGYYDWGHQIS-UHFFFAOYSA-N 0.000 description 1
- PFWHXKZZOQAFQC-UHFFFAOYSA-N n-(2-methylprop-2-enoyl)pentanamide Chemical compound CCCCC(=O)NC(=O)C(C)=C PFWHXKZZOQAFQC-UHFFFAOYSA-N 0.000 description 1
- OJBZOTFHZFZOIJ-UHFFFAOYSA-N n-acetyl-2-methylprop-2-enamide Chemical compound CC(=O)NC(=O)C(C)=C OJBZOTFHZFZOIJ-UHFFFAOYSA-N 0.000 description 1
- XOYONZYDWNTDAL-UHFFFAOYSA-N n-butoxyprop-2-enamide Chemical class CCCCONC(=O)C=C XOYONZYDWNTDAL-UHFFFAOYSA-N 0.000 description 1
- DUCHAQXTTBLNJC-UHFFFAOYSA-N n-ethoxy-n-methylprop-2-en-1-amine Chemical compound CCON(C)CC=C DUCHAQXTTBLNJC-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000005482 norpinyl group Chemical group 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000914 phenoxymethylpenicillanyl group Chemical group CC1(S[C@H]2N([C@H]1C(=O)*)C([C@H]2NC(COC2=CC=CC=C2)=O)=O)C 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001596 poly (chlorostyrenes) Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Chemical class 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- GVVKBARIYRBZHC-UHFFFAOYSA-N prop-2-enyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC=C GVVKBARIYRBZHC-UHFFFAOYSA-N 0.000 description 1
- CYFIHPJVHCCGTF-UHFFFAOYSA-N prop-2-enyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCC=C CYFIHPJVHCCGTF-UHFFFAOYSA-N 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- HPCIWDZYMSZAEZ-UHFFFAOYSA-N prop-2-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC=C HPCIWDZYMSZAEZ-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005627 triarylcarbonium group Chemical group 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/585—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aryl radicals
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Optical Filters (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Materials For Photolithography (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Cosmetics (AREA)
Description
又はR1、R2、R3、R4及びR5のいずれかは、それぞれ他の全てと無関係に、OH、OR10、SR10、SOR10、SO2R10、又はNR11R12であり;
又はR4はR3と一緒に又はR5と一緒に、1,3−プロピレン、1,3−プロペニレン、1,4−ブチレン、1,4−ブテン(1)イレン又は1,4−ブテン(2)イレン(それぞれ非置換であるか又はCl、F、OH、OR10、SR10、SOR10、SO2R10、NR11R12、CN、COR10、COOR10又はCONR11R12によって1回又は複数回置換される)、又は1,4−ブタジエニレン(非置換であるか又はSO3R10、SO2NR11R12、NO2、Br、Cl、F、OH、OR10、SR10、SOR10、SO2R10、NR11R12、CN、COR10、COOR10又はCONR11R12によって1回又は複数回置換される)であり;
又はR6は式
又はR7はアントラキノン下位構造の1位又は2位のCからR1への直接結合であり;
R10は、[C2−C6アルキレン−O]nC1−C12アルキル、[C2−C6アルキレン−NH]nC1−C12アルキル、C1−C12アルキル、C3−C12シクロアルキル、C2−C12アルケニル、C3−C12シクロアルケニル又はC2−C12アルキニル(それぞれ非置換であるか又はCl、F、OR21、NR22R23、CN、COR21、COOR21又はCONR22R23によって1回又は複数回置換される);C7−C12アラルキル又はC6−C12アリール(それぞれ非置換であるか又はNO2、SOR21、SO2R21、SO3R21、SO2NR22R23、Br、Cl、F、OR21、SR21、NR22R23、CN、COR21、COOR21又はCONR22R23によって1回又は複数回置換される)であり;
R11及びR12は、互いに無関係に、H、[C2−C6アルキレン−O]nC1−C12アルキル、[C2−C6アルキレン−NH]nC1−C12アルキル、C1−C12アルキル、C3−C12シクロアルキル、C2−C12アルケニル、C3−C12シクロアルケニル又はC2−C12アルキニル(それぞれ非置換であるか又はCl、F、OR21、NR22R23、CN、COR21、COOR21又はCONR22R23によって1回又は複数回置換される);C7−C12アラルキル又はC6−C12アリール(それぞれ非置換であるか又はNO2、SOR21、SO2R21、SO3R21、SO2NR22R23、Br、Cl、F、OR21、SR21、NR22R23、CN、COR21、COOR21又はCONR22R23によって1回又は複数回置換される)であり;又は
NR11R12はC、N、O及び/又はS原子を含む、5−、6−又は7−員環の、飽和の、不飽和の又は芳香族の、複素環式のN−基であり、この複素環式のN−基は場合によりシクロヘキサン、シクロヘキセン又はベンゼン環と縮合環化され且つ非置換であるか又はオキソ、ヒドロキシ、C1−C12アルコキシ、チオノ及び/又はR10によって1回又は複数回置換されており、2つ以上のR10は互いに同一又は異なり、そしてこの縮合環化されたベンゼン環は非置換であるか又はNO2、SOR21、SO2R21、SO3R21、SO2NR22R23、Br、Cl、F、OR21、NR22R23、CN、COR21、COOR21又はCONR22R23によって置換されており;
R13、R14及びR15はR7、R8及びR9とは無関係にR7、R8及びR9と同じ定義を有し、有利にはR13、R14及びR15はそれぞれR7、R8及びR9と同一であるか;又はR13はアントラキノン下位構造の1位又は2位のCからR16への直接結合であり;
R16、R17、R18、R19及びR20はR1、R2、R3、R4及びR5とは無関係にR1、R2、R3、R4及びR5と同じ定義を有し、有利にはR16、R17、R18、R19及びR20はそれぞれR1、R2、R3、R4及びR5と同一であり;
R21、R22及びR23は互いに無関係にH;[C2−C6アルキレン−O]nC1−C12アルキル、[C2−C6アルキレン−NH]nC1−C12アルキル又はC1−C12アルキル(非置換であるか又はF、オキソ、OH、OC1−C6アルキル、NH2、NHC1−C6アルキル、N(C1−C6アルキル)2、COOH、COOC1−C6アルキル、CONHC1−C6アルキル、CON(C1−C6アルキル)2又はCNによって1回又は複数回置換される)であり;
且つnは整数1、2、3、4又は5である)の化合物を含む着色剤組成物に関する。
又は式(II)で示され、その式中、R1、R2及びR3のうち少なくとも1つがSOR10、SO2R10、SO3R10、SO2NR11R12、CN、COR10、COOR10又はCONR11R12であるか、又はR6、R7、R8及びR9のうち少なくとも1つがSO2NR11R12である化合物(但し、該化合物は式
・塗布中の直接的なパターン形成
・着色剤を塗布した後のパターン形成
CH2=CHA1−Y1−A2−SO2−NH−A3 (a)
CH2=CHA4−Y2−A5−NH−SO2−A6 (b)
(式中、Y1及びY2はそれぞれ−COO−、−CONA7−、又は単結合を表し;A1及びA4はそれぞれH又はCH3を表し;A2及びA5はそれぞれC1−C12アルキレン(場合により置換基を有する)、シクロアルキレン、アリーレン、又はアラルキレン、又はC2−C12アルキレン(該基中にエーテル基及びチオエーテル基が挿入される)、シクロアルキレン、アリーレン、又はアラルキレンを表し;A3及びA6はそれぞれH、C1−C12アルキル(場合により置換基を有する)、シクロアルキル基、アリール基、又はアラルキル基を表し;そしてA7はH、C1−C12アルキル(場合により置換基を有する)、シクロアルキル基、アリール基、又はアラルキル基を表す)
によって表される化合物が挙げられる。
のベンゾフェノン類である。
G5はO、S、又はNR46であり;R43、R44及びR45は互いに無関係に水素、ハロゲン、C2−C12アルケニル、C1−C12アルコキシ、1〜4個の酸素原子によって中断されたC2−C12−アルコキシ、シクロヘキシルオキシ、シクロペンチルオキシ、フェノキシ、ベンジルオキシ、非置換のフェニルもしくはビフェニル又はC1−C4−アルコキシ、ハロゲン、フェニルチオもしくはC1−C4−アルキルチオによって置換されたフェニルもしくはビフェニルであるが、但しR43及びR45は共に水素ではなく、残基
R48、R49、R50、R51及びR52は互いに無関係に水素、非置換のC1−C12−アルキル又はOH、C1−C4−アルコキシ、フェニル、ナフチル、ハロゲン又はCNによって置換されたC1−C12−アルキルであり;その際、アルキル鎖は場合により1つ以上の酸素原子によって中断されており;又はR48、R49、R50、R51及びR52は互いに無関係にC1−C4−アルコキシ、C1−C4−アルキルチオ又はNR37R38であり;R37及びR38は互いに無関係に水素、非置換のC1−C12−アルキル又はOHもしくはSHによって置換されたC1−C12−アルキルであり、その際、アルキル鎖は場合により1〜4個の酸素原子によって中断されており;又はR37及びR38は互いに無関係にC2−C12−アルケニル、シクロペンチル、シクロヘキシル、ベンジル又はフェニルであり;且つY1は場合により1つ以上の酸素原子によって中断されたC1−C12−アルキレンである)のグリオキサル酸フェニルである。それらの特殊な例はオキソ−フェニル−酢酸2−[2−(2−オキソ−2−フェニル−アセトキシ)−エトキシ]−エチルエステルである。
HPLC(CH3CN):300nm及び426nm(PVC:432nm)でのλmaxにおいて純度94%;
ESI−LC−MS:M=316g/モル及び424g/モル(陰性イオン化による(微量のビス−フェニルスルファニル−アントラキノン));
HPLC(THF):306nm及び422nmでのλmaxにおいて純度94.5%;
融点:186℃(DSCにより、10℃/分で30〜300℃);
ESI−LC−MS:M=439g/モル(陰性イオン化による);
示差走査熱量測定(10℃/分で30〜300℃):158℃(吸熱)、161℃(発熱)及び186℃(吸熱)。
ESI−LC−MS:M=483g/モル(陰性イオン化による)。
DSC(10℃/分で30〜300℃):188℃(吸熱)、しかし既に観察された鋭い変曲点158℃(吸熱)及び161℃(発熱)はこのスペクトル中に存在していない。
融点:153℃(示差走査熱量測定、10℃/分で30〜300.0℃);
ESI−LC−MS:M=483g/モル(陰性イオン化による);
融点:177℃(示差走査熱量測定、10℃/分で30〜300℃);
(5)のESI−LC−MS:M=469g/モル(陰性イオン化による);
ESI−LC−MS:M=511g/モル(陰性イオン化による);
示差走査熱量測定(10℃/分で30〜300.0℃):101℃(吸熱)、106℃(発熱)及び193℃(吸熱);
1.92部のDisperbyk(登録商標)161(カチオン性ポリウレタン、分散剤)
9部のアクリル酸/アクリレート樹脂バインダー
12.5部のN−メチルピロリドン(NMP)
2.3部のSartomer(登録商標)399(ジペンタエリトリトールペンタアクリラート)
0.08部の2,4−ビス(トリクロロメチル)−6−(4−メトキシフェニル)−1,3,5−トリアジン
Claims (9)
- 透明基材及び1つの層又は複数の層をその上に含むカラーフィルターであって、少なくとも1つの層がパターン形成された層であり、該パターン形成された層は式
R6、R7、R8、及びR9はHであり;及びR11又はR12はヒドロキシ基を含み、;
R 11 及びR12は、互いに無関係に、H、[C2−C6アルキレン−O]nC1−C12アルキル、[C2−C6アルキレン−NH]nC1−C12アルキル、C1−C12アルキル、C3−C12シクロアルキル、C2−C12アルケニル、C3−C12シクロアルケニル又はC2−C12アルキニル(それぞれ非置換であるか又はOR21によって1回又は複数回置換される);
R21はH;且つnは整数1、2、3、4又は5である)の化合物を含むカラーフィルター。 - 前記パターン形成された層が、式(I)の化合物及び10から200nmまでの平均粒度の顔料を含む、請求項1に記載のカラーフィルター。
- 前記顔料がカラーインデックスピグメントレッド2、4、5、23、48:1、48:2、48:3、48:4、52:2、53:1、57、57:1、88、89、101、104、112、122、144、146、149、166、168、177、178、179、181、184、190、192、194、202、204、206、207、209、214、216、220、221、222、224、226、254、255、262、264、270、272、282、283、ピグメントグリーン7、17、36、37、50、又はそれらの混合物である、請求項2記載のカラーフィルター。
- 前記顔料及び前記式(I)の化合物が、一緒に同じパターン形成された層に含まれる、請求項2又は3に記載のカラーフィルター。
- 前記顔料及び前記式(I)の化合物が、同じパターンを示す2つの異なる層に存在し、
それらの着色された領域が同じピクセルで、一致するように重ね合わされる、請求項2又は3に記載のカラーフィルター。 - 以下の、式(I)
R 6 、R 7 、R 8 、及びR 9 はHであり;及びR 11 又はR 12 はヒドロキシ基を含み、;
R 11 及びR 12 は、互いに無関係に、H、[C 2 −C 6 アルキレン−O] n C 1 −C 12 アルキル、[C 2 −C 6 アルキレン−NH] n C 1 −C 12 アルキル、C 1 −C 12 アルキル、C 3 −C 12 シクロアルキル、C 2 −C 12 アルケニル、C 3 −C 12 シクロアルケニル又はC 2 −C 12 アルキニル(それぞれ非置換であるか又はOR 21 によって1回又は複数回置換される);
R 21 はH;且つnは整数1、2、3、4又は5である)で示される化合物。 - パターン形成されたカラーフィルターを製造するための、フォトレジストにおける、請求項6に記載の化合物の使用。
- 請求項6記載の化合物を含むフォトレジスト組成物。
- 前記層が、該層の全質量を基準として、1〜75質量%の、高分子量の有機材料中に分散された式(I)で示される化合物を含む、請求項1に記載のカラーフィルター。
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PCT/EP2008/051699 WO2008101841A1 (en) | 2007-02-23 | 2008-02-13 | Transparent colourants and colourant compositions, and their use |
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KR101732197B1 (ko) | 2009-01-19 | 2017-05-02 | 바스프 에스이 | 컬러 필터를 위한 블랙 매트릭스 |
CN103328589B (zh) * | 2011-01-31 | 2015-07-29 | 惠普发展公司,有限责任合伙企业 | 喷墨油墨组 |
JP5932435B2 (ja) * | 2012-03-29 | 2016-06-08 | サカタインクス株式会社 | カラーフィルター用青色顔料分散組成物及びそれを含有するカラーフィルター用青色顔料分散レジスト組成物 |
KR102116438B1 (ko) * | 2012-05-21 | 2020-05-29 | 토요잉크Sc홀딩스주식회사 | 컬러 필터용 착색 조성물 및 컬러 필터 |
WO2013179237A1 (en) | 2012-06-01 | 2013-12-05 | Basf Se | Black colorant mixture |
JP5568805B2 (ja) * | 2012-10-31 | 2014-08-13 | 東洋インキScホールディングス株式会社 | 有機el表示装置用赤色着色組成物、カラーフィルタ、および有機el表示装置 |
CN106909027B (zh) * | 2015-12-23 | 2021-07-16 | 东友精细化工有限公司 | 着色感光性树脂组合物、滤色器及其制法、图像显示装置 |
KR101840984B1 (ko) * | 2017-11-10 | 2018-03-21 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 사용하여 제조된 블랙 매트릭스, 컬럼 스페이서 또는 블랙 컬럼 스페이서를 포함하는 컬러필터, 및 상기 컬러필터를 포함하는 표시장치 |
WO2019121602A1 (en) | 2017-12-19 | 2019-06-27 | Basf Se | Cyanoaryl substituted benz(othi)oxanthene compounds |
KR101873000B1 (ko) * | 2018-03-05 | 2018-08-02 | (주)옵토레인 | 광각 이미션 필터, 이를 갖는 광학센서 어셈블리, 이를 포함하는 피씨알 시스템, 및 그 제조방법 |
WO2019243286A1 (en) | 2018-06-22 | 2019-12-26 | Basf Se | Photostable cyano-substituted boron-dipyrromethene dye as green emitter for display and illumination applications |
JP7526104B2 (ja) | 2018-06-25 | 2024-07-31 | サン・ケミカル・ベスローテン・ヴェンノーツハップ | カラーフィルター用赤色顔料組成物 |
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JP7496467B1 (ja) | 2023-10-26 | 2024-06-06 | 大日精化工業株式会社 | 着色樹脂成型品、着色フィルム、着色インキおよび印刷フィルム |
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WO2008101841A1 (en) | 2008-08-28 |
US8399161B2 (en) | 2013-03-19 |
DE602008004743D1 (de) | 2011-03-10 |
CN101636453B (zh) | 2014-03-26 |
JP2010520929A (ja) | 2010-06-17 |
TW200900471A (en) | 2009-01-01 |
CN101636453A (zh) | 2010-01-27 |
KR101524320B1 (ko) | 2015-06-02 |
KR20100014529A (ko) | 2010-02-10 |
ATE496972T1 (de) | 2011-02-15 |
US20100021831A1 (en) | 2010-01-28 |
TWI428400B (zh) | 2014-03-01 |
EP2125960B1 (en) | 2011-01-26 |
EP2125960A1 (en) | 2009-12-02 |
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