WO2014126167A1 - 着色組成物 - Google Patents
着色組成物 Download PDFInfo
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- WO2014126167A1 WO2014126167A1 PCT/JP2014/053367 JP2014053367W WO2014126167A1 WO 2014126167 A1 WO2014126167 A1 WO 2014126167A1 JP 2014053367 W JP2014053367 W JP 2014053367W WO 2014126167 A1 WO2014126167 A1 WO 2014126167A1
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- carbon atoms
- general formula
- anion
- dye
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- 239000000203 mixture Substances 0.000 title claims abstract description 54
- -1 cationic rhodamine derivative Chemical class 0.000 claims abstract description 348
- 239000000178 monomer Substances 0.000 claims abstract description 171
- 229920000642 polymer Polymers 0.000 claims abstract description 152
- 150000001450 anions Chemical class 0.000 claims abstract description 68
- 125000001424 substituent group Chemical group 0.000 claims abstract description 50
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 185
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 40
- 238000004040 coloring Methods 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- DBDNZCBRIPTLJF-UHFFFAOYSA-N boron(1-) monohydride Chemical group [BH-] DBDNZCBRIPTLJF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000004964 sulfoalkyl group Chemical group 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 231
- 239000000126 substance Substances 0.000 description 60
- 230000015572 biosynthetic process Effects 0.000 description 55
- 238000003786 synthesis reaction Methods 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- 239000000049 pigment Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 23
- 238000011156 evaluation Methods 0.000 description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 21
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 20
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000010408 film Substances 0.000 description 15
- 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 14
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 12
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 12
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 12
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- 229940043267 rhodamine b Drugs 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- 239000003505 polymerization initiator Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000005342 ion exchange Methods 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 6
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005349 anion exchange Methods 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000007810 chemical reaction solvent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910003002 lithium salt Inorganic materials 0.000 description 6
- 159000000002 lithium salts Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- AEZJNQZYZFLLIY-UHFFFAOYSA-N 12-hydroxydodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCO AEZJNQZYZFLLIY-UHFFFAOYSA-N 0.000 description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000007877 V-601 Substances 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 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 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 5
- 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 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- GWSWKPOCFYOYFM-UHFFFAOYSA-N FC1=C(C(=C(C(=C1[B+3])F)F)F)F Chemical compound FC1=C(C(=C(C(=C1[B+3])F)F)F)F GWSWKPOCFYOYFM-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000005042 acyloxymethyl group Chemical group 0.000 description 4
- 125000004849 alkoxymethyl group Chemical group 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- 125000004212 difluorophenyl group Chemical group 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000006501 nitrophenyl group Chemical group 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000004360 trifluorophenyl group Chemical group 0.000 description 4
- ZOICEQJZAWJHSI-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)boron Chemical compound [B]C1=C(F)C(F)=C(F)C(F)=C1F ZOICEQJZAWJHSI-UHFFFAOYSA-N 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- ZUQABTLQDXJZFK-UHFFFAOYSA-N 10-hydroxydecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCO ZUQABTLQDXJZFK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- XFOFBPRPOAWWPA-UHFFFAOYSA-N 6-hydroxyhexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCO XFOFBPRPOAWWPA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UOQDFONSGGASLE-UHFFFAOYSA-N [Li+].FC1=C(C(=C(C(=C1[B+3])F)F)F)F Chemical compound [Li+].FC1=C(C(=C(C(=C1[B+3])F)F)F)F UOQDFONSGGASLE-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 125000002993 cycloalkylene group Chemical group 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
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- 125000001802 myricyl 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])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])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
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DFENKTCEEGOWLB-UHFFFAOYSA-N n,n-bis(methylamino)-2-methylidenepentanamide Chemical compound CCCC(=C)C(=O)N(NC)NC DFENKTCEEGOWLB-UHFFFAOYSA-N 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002465 nonacosyl 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])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])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
- 125000001196 nonadecyl 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])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
- 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
- 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 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002460 pentacosyl 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])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
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- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical group CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SURWZXDYYLMDQT-UHFFFAOYSA-M sodium;2,3,4,5,6-pentafluorobenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F SURWZXDYYLMDQT-UHFFFAOYSA-M 0.000 description 1
- 125000004079 stearyl 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])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
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002469 tricosyl 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])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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 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
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
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- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
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- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
- C07C309/31—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups by alkyl groups containing at least three carbon atoms
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- C07C309/01—Sulfonic acids
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- C07C309/01—Sulfonic acids
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- C07C309/40—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitro or nitroso groups bound to the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- C09B11/00—Diaryl- or thriarylmethane dyes
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- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
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- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
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- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
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- C09B69/00—Dyes not provided for by a single group of this subclass
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- G02B5/22—Absorbing filters
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C309/01—Sulfonic acids
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
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- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
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- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
- C08F120/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F120/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
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- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
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- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/36—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to some other heterocyclic ring
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- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/36—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to some other heterocyclic ring
- C09B62/365—Specific dyes not provided for in groups C09B62/38 - C09B62/42
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- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
Definitions
- the present invention relates to a polymer used for forming colored pixels such as a color filter, a printing ink, an inkjet ink, and a paint, and a coloring composition containing the polymer.
- Color pixel formation methods in the production of color filters such as liquid crystal display devices and solid-state image sensors include dyeing methods using dyes as dyes, dye dispersion methods, pigment dispersion methods using pigments, electrodeposition methods, and printing methods. Etc. are known. In recent years, improvements in luminance and contrast are particularly required as the characteristics of color filters. According to the pigment dispersion method using a pigment, since heat resistance and light resistance are higher than those of dyes, a color pixel with little deterioration in a heating process at the time of panel manufacture and high long-term reliability can be obtained. Therefore, the pigment dispersion method has become mainstream at present. However, when a pigment is used, since the pigment itself has a particle size, there is a problem that the contrast is lowered due to light scattering. Attempts have been made to make the pigment fine, but there is a limit to making it fine, and securing the dispersion stability of the finely divided pigment has also been an issue.
- the present inventors have found a compound having a cationic rhodamine derivative having a specific anion as a counter anion and an ethylenically unsaturated bond, or a polymer having a monomer unit derived from the compound. By using it as a dye, it was found that a colored composition having excellent heat resistance and little dye elution was obtained, and the present invention was completed.
- the present invention is derived from "(i) a compound having an aryl group having an electron-withdrawing substituent and an anion containing an anion group as a counter anion and (ii) a compound having an ethylenically unsaturated bond.”
- the present invention relates to a “coloring composition comprising the polymer or compound” and a “coloring composition for a color filter comprising the polymer or compound”.
- the coloring composition containing the polymer or compound of the present invention has a heat resistance effect superior to that of the conventional coloring composition.
- the polymer or compound of the present invention has an effect that the elution of the dye (colorant) is small when these are used as a colorant in a resist material. Therefore, compared with the conventional coloring composition, provision of the outstanding coloring composition which does not have problems, such as a fall of color density and color mixing, is enabled.
- anion group in the anion of the cationic rhodamine derivative examples include a sulfonate anion group, a quaternary boron anion group, a nitrate ion, and a phosphate ion.
- a sulfonic acid anion group and a quaternary boron anion group are preferable, and a quaternary boron anion group is more preferable.
- Examples of the electron-withdrawing substituent in the anion according to the present invention include a halogenated alkyl group having 1 to 3 carbon atoms, a halogeno group, a nitro group, etc. Among them, a halogeno group and a nitro group are preferable, and a halogeno group is preferable. Particularly preferred.
- halogenated alkyl group having 1 to 3 carbon atoms examples include chloromethyl group, trichloromethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 2-chloropropyl group, 3-chloropropyl group, Chloroalkyl group such as 2-chloro-2-propyl group; bromomethyl group, tribromomethyl group, 2-bromoethyl group, 2,2,2-tribromoethyl group, 2-bromopropyl group, 3-bromopropyl group, Bromoalkyl groups such as 2-bromo-2-propyl group; iodomethyl group, triiodomethyl group, 2-iodoethyl group, 2,2,2-triiodoethyl group, 2-iodopropyl group, 3-iodopropyl group, Iodoalkyl groups such as 2-iodo-2-propyl group; fluoromethyl
- halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group, and a fluoro group is preferable.
- the electron-withdrawing substituent in the anion according to the present invention is preferably one having a strong electron-withdrawing force, preferably a trifluoromethyl group, a fluoro group, or a nitro group, and more preferably a fluoro group or a nitro group.
- Examples of the aryl group in the anion according to the present invention include a phenyl group and a naphthyl group, and a phenyl group is preferable.
- Examples of the aryl group having an electron-withdrawing substituent in the anion according to the present invention include those represented by the following general formulas (XI) and (XII).
- m represents an integer of 1 to 5
- m R 41 s each independently represent a halogenated alkyl group having 1 to 3 carbon atoms, a halogen atom or a nitro group, and * represents a bond. Represents.
- k represents an integer of 1 to 7.
- R 41 and * are the same as above.
- K R 41 may be the same or different.
- m is usually an integer of 1 to 5, but when R 41 is a halogen atom, it is preferably 2 to 5, more preferably 3 to 5, and still more preferably 5.
- R 41 is a nitro group, it is preferably 1 to 3, and more preferably 1.
- R 41 is a halogenated alkyl group, 1 to 5 is preferable.
- k is usually an integer of 1 to 7, but preferably 2 to 7 when R 41 is a halogen atom.
- R 41 is a nitro group, it is preferably 1 to 3, and more preferably 1.
- R 41 is a halogenated alkyl group, 1 to 7 is preferred.
- the halogenated alkyl group having 1 to 3 carbon atoms of R 41 in the general formula (XI) and the general formula (XII) is an alkyl halide having 1 to 3 carbon atoms in the electron-withdrawing substituent in the anion according to the present invention.
- the same thing as a group is mentioned, A preferable thing is also the same.
- halogen atom in the general formula (XI) and the general formula (XII) examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among them, a fluorine atom is preferable.
- R 41 in the general formula (XI) and the general formula (XII) are the same as the preferable examples of the electron-withdrawing substituent in the anion according to the present invention.
- Specific examples of the group represented by the general formula (XI) include a trifluoromethylphenyl group, a di (trifluoromethyl) phenyl group, a tri (trifluoromethyl) phenyl group, a monofluorophenyl group, a difluorophenyl group, Trifluorophenyl, perfluorophenyl, monochlorophenyl, dichlorophenyl, trichlorophenyl, perchlorophenyl, monobromophenyl, dibromophenyl, tribromophenyl, perbromophenyl, monoiodophenyl, di Examples include iodophenyl group, triiodophenyl group, periodiophenyl group, nitrophenyl group, dinitrophenyl group, trinitrophenyl group, and the like. Difluorophenyl group, trifluorophenyl group, perfluorophenyl group,
- Specific examples of the group represented by the general formula (XII) include, for example, a trifluoromethylnaphthyl group, a di (trifluoromethyl) naphthyl group, a tri (trifluoromethyl) naphthyl group, a monofluoronaphthyl group, a difluoronaphthyl group, Trifluoronaphthyl group, perfluoronaphthyl group, monochloronaphthyl group, dichloronaphthyl group, trichloronaphthyl group, perchloronaphthyl group, monobromonaphthyl group, dibromonaphthyl group, tribromonaphthyl group, perbromonaphthyl group, monoiodonaphthyl group , Diiodonaphthyl group, triiodonaphthyl group, periodona
- the aryl group having an electron-withdrawing substituent in the anion according to the present invention is preferably a group represented by the general formula (XI), specifically, a trifluoromethylphenyl group, a nitrophenyl group, Dinitrophenyl group, trinitrophenyl group, monofluorophenyl group, difluorophenyl group, trifluorophenyl group, and perfluorophenyl group are preferable, and difluorophenyl group, trifluorophenyl group, nitrophenyl group, and perfluorophenyl group are more preferable. More preferred are a nitrophenyl group and a perfluorophenyl group.
- anion containing an aryl group having an electron-withdrawing substituent and an anion group according to the present invention include those represented by the following general formulas (XIII) to (XVI).
- R 41 and m are the same as above.
- M R 41 may be the same or different.
- R 41 and k are the same as above.
- the k R 41 s may be the same or different.
- R 41 and k are the same as above.
- the k R 41 s may be the same or different.
- R 42 to R 45 each independently represents a halogenated alkyl group having 1 to 3 carbon atoms, a halogen or a nitro group, and m 1 to m 4 each independently represents 1 to 5 carbon atoms
- m 1 single R 42 represents an integer may be the same or different
- m 2 pieces of R 43, m 3 pieces of R 44 and m 4 pieces of R 45 also may be the same as or different from each other .
- Examples of the combination of R 41 and m in the general formula (XIII) include those described in the following table.
- the anion according to the present invention is preferably one represented by the general formula (XIII) or the general formula (XVI), more preferably one represented by the general formula (XVI).
- Is particularly preferred Is more preferable.
- the cationic rhodamine derivative according to the present invention has the anion according to the present invention as a counter anion, and examples thereof include compounds represented by the following general formula (VII).
- R 1 to R 4 are each independently a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, a sulfoalkyl group having 1 to 6 carbon atoms, or 2 carbon atoms.
- R 5 to R 6 each independently represents a hydrogen atom or a methyl group.
- An ⁇ represents an anion (an anion including an aryl group having an electron-withdrawing substituent and an anion group) according to the present invention. ]
- the alkyl group having 1 to 30 carbon atoms in R 1 to R 4 may be linear, branched or cyclic, preferably has 1 to 6 carbon atoms, and more preferably has 1 to 3 carbon atoms. .
- the hydroxyalkyl group having 1 to 6 carbon atoms in R 1 to R 4 is preferably 1 to 3 carbon atoms. Specifically, for example, hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, hydroxypentyl Group, hydroxyhexyl group and the like.
- the sulfoalkyl group having 1 to 6 carbon atoms in R 1 to R 4 preferably has 1 to 3 carbon atoms, and specifically includes, for example, a sulfomethyl group, a sulfoethyl group, a sulfopropyl group, a sulfobutyl group, a sulfopentyl group, a sulfo group.
- a hexyl group etc. are mentioned.
- the carboxyalkyl group having 2 to 7 carbon atoms in R 1 to R 4 preferably has 3 to 6 carbon atoms, and specifically includes, for example, a carboxymethyl group, a carboxyethyl group, a carboxypropyl group, a carboxybutyl group, and a carboxypentyl group. Group, a carboxyhexyl group, etc. are mentioned, A carboxyethyl group is preferable.
- the cyanoalkyl group having 2 to 7 carbon atoms in R 1 to R 4 preferably has 2 to 4 carbon atoms.
- a cyanomethyl group, a cyanoethyl group, a cyanopropyl group, a cyanobutyl group, a cyanopentyl group, a cyano group A hexyl group etc. are mentioned, A cyanoethyl group is preferable.
- the alkoxyalkyl group having 2 to 6 carbon atoms in R 1 to R 4 preferably has 3 to 5 carbon atoms, and specifically includes, for example, a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an ethoxyethyl group, and propoxymethyl. Group, propoxyethyl group, butoxymethyl group, butoxyethyl group and the like.
- the halogenoalkyl group having 1 to 6 carbon atoms in R 1 to R 4 is preferably 1 to 3 carbon atoms, and specifically includes, for example, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a trichloromethyl group, A tribromomethyl group, a triiodomethyl group, etc. are mentioned.
- the phenyl group or benzyl group in R 1 to R 4 may have 1 to 5, preferably 1 to 3 substituents.
- substituents include a methyl group, an ethyl group, a propyl group, Alkyl groups having 1 to 6 carbon atoms such as isopropyl group, butyl group, isobutyl group, t-butyl group and pentyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; sulfonic acid group, methoxy group, Alkoxy groups having 1 to 6 carbon atoms such as ethoxy group, propoxy group, butoxy group, t-butoxy group, hexyloxy group; hydroxyalkyl groups such as hydroxyethyl group, hydroxypropyl group; methoxyethyl group, ethoxyethyl group, ethoxy C2-C10 alkoxyalkyl groups such as propy
- a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, a hexyl group, and the like are preferable, and a hydrogen atom, a methyl group, an ethyl group, and a propyl group are preferable.
- Etc. are more preferable, and a hydrogen atom and an ethyl group are particularly preferable.
- R 5 and R 6 are preferably a hydrogen atom or a methyl group.
- R 1 to R 6 examples include those listed in the following table.
- the polymer of the present invention is a polymer having a monomer unit derived from a compound having the cationic rhodamine derivative according to the present invention and the ethylenically unsaturated bond according to the present invention.
- the weight average molecular weight (Mw) of the polymer of the present invention is usually 2,000 to 100,000, preferably 2,000 to 50,000, more preferably 2,000 to 30,000.
- the degree of dispersion (Mw / Mn) is usually 1.00 to 5.00, preferably 1.00 to 3.00.
- the ethylenically unsaturated bond according to the present invention may be any ethylenically unsaturated bond having polymerizability, and specifically includes a vinyl group having no aromaticity.
- the group having an ethylenically unsaturated bond according to the present invention and the cationic rhodamine derivative according to the present invention are bonded directly or via an appropriate spacer.
- the spacer include an alkylene group having 1 to 21 carbon atoms having at least one of —O—, —OCO—, —COO—, or an arylene group in the chain, and a hydroxyl group as a substituent.
- polymer of the present invention include those having a monomer unit derived from a compound represented by the following general formula (I).
- R 1 to R 6 and An ⁇ are the same as described above.
- R 7 represents a hydrogen atom or a methyl group
- a 1 represents at least one of —O—, —OCO—, —COO—, or an arylene group.
- R 7 is preferably a methyl group.
- the alkylene group having 1 to 9 carbon atoms in A 1 may be any of linear, branched and cyclic alkylene groups, preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. .
- the alkylene group having 1 to 6 carbon atoms having a hydroxyl group as a substituent in A 1 above preferably has 1 to 3 carbon atoms, and specifically includes, for example, a hydroxymethylene group, a hydroxyethylene group, a 1-hydroxypropylene group, Examples include 2-hydroxypropylene group, 1-hydroxybutylene group, 1-hydroxypentylene group, methylenehydroxyhexylmethyl group and the like.
- arylene group in the alkylene group having 1 to 21 carbon atoms having -O-, -OCO-, -COO- group or arylene in A 1 and having a hydroxyl group as a substituent examples thereof include those having 6 to 10 carbon atoms, and specific examples thereof include a phenylene group and naphthylene.
- alkylene group having 1 to 21 carbon atoms which has —O—, —OCO—, —COO— group or arylene in A 1 and has a hydroxyl group as a substituent include Group represented by formula (VI-I)
- R 52 represents an alkylene group having 1 to 6 carbon atoms having a hydroxyl group as a substituent, and p2 represents an integer of 1 to 3).
- Examples of the cycloalkylene group having 4 to 7 carbon atoms having a hydroxyl group as a substituent in R 51 of the general formula (VI-I) include a hydroxycyclobutylene group, a hydroxycyclopentylene group, a hydroxycyclohexylene group, a hydroxycyclohexane group. Examples include a heptylene group.
- Examples of the alkylene group having 1 to 6 carbon atoms having a hydroxyl group as a substituent in R 52 of the general formula (VI-II) include a hydroxymethylene group, a hydroxyethylene group, a hydroxypropylene group, a hydroxybutylene group, and a hydroxypentylene group. And a hydroxyhexylene group.
- Preferable specific examples of the group represented by the general formula (VI-II) include, for example, —CH 2 —CH (OH) —CH 2 —O— (CH 2 ) 2 —, —CH 2 —CH (OH) —CH 2 —O— (CH 2 ) 3 —, —CH 2 —CH (OH) —CH 2 —O— (CH 2 ) 4 —, Etc.
- the arylene group of the alkylene group having 1 to 21 carbon atoms and having at least one group of —O—, —OCO—, —COO— or an arylene group in A 1 above has 6 to 10 carbon atoms Specifically, a phenylene group, naphthylene, etc. are mentioned.
- Examples of the branched alkylene group having 1 to 3 carbon atoms represented by R 54 include a methylmethylene group, a methylethylene group, and a methylpropylene group.
- methylene group, ethylene group, propylene group, butylene group, pentylene group, hexylene group is preferable, and a methylene group, an ethylene group, a propylene group are more preferred, and an ethylene group is particularly preferred.
- a 2 is preferably —O—.
- the number of atoms between the double bond and the benzene ring that is, represented by —C ( ⁇ O) —O—A 1 —A 2 —C ( ⁇ O) —
- the reaction rate when the compound is polymerized increases, and the effect of the polymer of the present invention can be further exhibited.
- the number exceeds 16 the heat resistance effect gradually decreases. Therefore, the number of atoms is usually 5 to 20, preferably 6 to 16, more preferably 6 to 14, and particularly preferably 10 to 14.
- R 1 to R 7 , A 1 and A 2 in the general formula (I) include those described in the following table, for example.
- the polymer of the present invention may be a homopolymer or a copolymer as long as it has a monomer unit derived from the compound represented by the general formula (I), but a copolymer having a high heat resistance effect is preferable.
- Examples of the copolymer include a monomer unit derived from the compound represented by the general formula (I) and a compound represented by the following general formula (II), general formula (III), general formula (IV), or general formula (V). Examples thereof include those derived from 1 to 2 types of derived monomer units.
- R 11 represents a hydrogen atom or a methyl group
- R 12 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a hydroxylalkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
- R 15 represents an alkylene group having 1 to 3 carbon atoms
- R 16 represents a phenyl group having a hydroxyl group as a substituent or an unsubstituted phenyl group, or an alkyl group having 1 to 3 carbon atoms
- q represents an integer of 1 to 3
- R 17 to R 19 represent an alkyl group having 1 to 3 carbon atoms
- R 20 represents an alkylene group having 1 to 3 carbon atoms
- R 11 is the same as above.
- R 13 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms;
- R 14 represents a hydrogen atom or a dialkylaminoalkyl group having 3 to 7 carbon atoms;
- R 13 and R 14 may form a morpholino group with a nitrogen atom adjacent to R 13 and R 14 ),
- R 31 represents a phenyl group or a pyrrolidino group, and R 11 is the same as above.
- R 33 represents a nitrogen atom or an oxygen atom
- j represents 0 when R 33 is an oxygen atom
- R 32 represents a hydrogen atom.
- R 11 in the general formula (II) is preferably a methyl group.
- the alkyl group having 1 to 18 carbon atoms in R 12 of the general formula (II) may be linear, branched or cyclic.
- Examples of the hydroxylalkyl group having 1 to 10 carbon atoms in R 12 of the general formula (II) include a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxypentyl group, and a hydroxyhexyl group.
- Examples of the aryl group having 6 to 10 carbon atoms in R 12 of the general formula (II) include a phenyl group and a naphthyl group.
- Examples thereof include an arylalkyl group having 7 to 13 carbon atoms in R 12 of the general formula (II), a benzyl group, a phenylethyl group, a phenylpropyl group, a naphthylmethyl group, a naphthylethyl group, a naphthylpropyl group, and the like, and a benzyl group is preferable. .
- Examples of the alkoxyalkyl group having 2 to 9 carbon atoms in R 12 of the general formula (II) include methoxymethyl group, methoxyethyl group, methoxypropyl group, methoxybutyl group, methoxypentyl group, methoxyhexyl group, methoxyheptyl group, methoxy Octyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, ethoxybutyl group, ethoxypentyl group, ethoxyhexyl group, ethoxyheptyl group, propoxymethyl group, propoxyethyl group, propoxypropyl group, propoxybutyl group, propoxypentyl group And propoxyhexyl group.
- Examples of the alkoxyalkoxyalkyl group having 3 to 9 carbon atoms in R 12 of the general formula (II) include a methoxymethoxymethyl group, a methoxymethoxyethyl group, a methoxymethoxypropyl group, an ethoxymethoxymethyl group, an ethoxymethoxyethyl group, and an ethoxymethoxypropyl group.
- Examples of the aryloxyalkyl group having 7 to 13 carbon atoms in R 12 of the general formula (II) include a phenoxymethyl group, a phenoxyethyl group, a phenoxypropyl group, a naphthyloxymethyl group, a naphthyloxyethyl group, and a naphthyloxypropyl group. Can be mentioned.
- Examples of the morpholinoalkyl group having 5 to 7 carbon atoms in R 12 of the general formula (II) include morpholinomethyl group, morpholinoethyl group, morpholinopropyl group and the like.
- Examples of the trialkylsilyl group having 3 to 9 carbon atoms in R 12 of the general formula (II) include a trimethylsilyl group, a tolylethylsilyl group, a tripropylsilyl group, a dimethylethylsilyl group, and a diethylmethylsilyl group.
- Examples of the alicyclic hydrocarbon group having 6 to 10 carbon atoms having oxygen in R 12 of the general formula (II) include a dicyclopentenyloxyethyl group.
- Examples of the alicyclic hydrocarbon group having 6 to 10 carbon atoms that does not contain oxygen in R 12 of the general formula (II) include a cyclohexyl group, an isobornyl group, and a dicyclopentanyl group.
- dialkylaminoalkyl group having 3 to 9 carbon atoms in R 12 of the general formula (II) examples include dimethylaminomethyl group, dimethylaminoethyl group, dimethylaminopropyl group, diethylaminomethyl group, diethylaminoethyl group, diethylaminopropyl group, A propylaminomethyl group, a dipropylaminoethyl group, a dipropylaminopropyl group, etc. are mentioned.
- Examples of the fluorinated alkyl group having 1 to 18 carbon atoms in R 12 of the general formula (II) include 2,2,2-trifluoroethyl group, 2,2,3,3? Tetrafluoropropyl group, 2,2,3,3? Tetrafluoropropyl group, 2,2,3,3,4,4-hexafluoropropyl group, 2,2,3,3,4,4,5,5-octafluoropentyl group, 3,3,4,4 5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl; 2- (heptadecafluorooctyl) ethyl group and the like.
- N-alkylenephthalimide group having 1 to 6 carbon atoms in R 12 of the general formula (II) examples include a 2-phthalimidoethyl group and a 2-tetrahydrophthalimidoethyl group.
- Examples of the alkylene group having 1 to 3 carbon atoms in R 15 in the general formula (II-I) include a methylene group, an ethylene group, and a propylene group, and an ethylene group is preferable.
- Examples of the phenyl group having or not substituted with the hydroxyl group of R 16 in the general formula (II-I) include a hydroxyphenyl group and a phenyl group.
- Examples of the alkyl group having 1 to 3 carbon atoms of R 16 in the general formula (II-I) include a methyl group, an ethyl group, and a propyl group.
- Specific examples of the group represented by the general formula (II-I) include 2-hydroxy-3-phenoxymethyl group, 2-hydroxy-3-phenoxyethyl group, 2-hydroxy-3-phenoxypropyl group, methyltrimethylene Examples thereof include a glycol group, a methyltriethylene glycol group, and a methyltripropylene glycol group. Among them, a 2-hydroxy-3-phenoxypropyl group, a methyltripropylene glycol group, a methyltriethylene glycol group, and the like are preferable.
- Examples of the alkyl group having 1 to 3 carbon atoms in R 17 to R 19 in the general formula (II-II) include a methyl group, an ethyl group, and a propyl group, and a methyl group is preferable.
- Examples of the alkylene group having 1 to 3 carbon atoms in R 20 in the general formula (II-II) include a methylene group, an ethylene group, and a propylene group.
- Specific examples of the group represented by the general formula (II-II) include a trimethylammonium methyl group, a trimethylammonium ethyl group, a triethylammonium methyl group, and a triethylammonium ethyl group.
- R 12 in the general formula (II) is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or 7 carbon atoms.
- a hydrogen atom, an arylalkyl group having 7 to 13 carbon atoms, and a group represented by the general formula (II-III) are more preferable.
- Preferred specific examples of the general formula (II) include methacrylic acid, benzyl methacrylate, hydroxyethyl methacrylate, methyl methacrylate and the like, and among them, methacrylic acid, benzyl methacrylate and the like are preferable.
- Examples of the alkyl group having 1 to 3 carbon atoms in R 13 of the general formula (III) include a methyl group, an ethyl group, and a propyl group.
- Examples of the dialkylaminoalkyl group having 3 to 9 carbon atoms in R 14 of the general formula (III) include a dimethylaminomethyl group, a dimethylaminoethyl group, a dimethylaminopropyl group, a diethylaminomethyl group, a diethylaminoethyl group, a diethylaminopropyl group, A propylaminomethyl group, a dipropylaminoethyl group, a dipropylaminopropyl group, etc. are mentioned.
- Examples of the alkyl group of 1 to 3 include the same groups as those described above for R 13 .
- Examples of the hydroxyalkyl group having 1 to 6 carbon atoms in R 14 of the general formula (III) include a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxypentyl group, a hydroxyhexyl group, and the like.
- An ethyl group is preferred.
- Specific preferred examples of the general formula (III) include (meth) acrylamide, N, N-dimethylacrylamide, N, N-diethylacrylamide, hydroxyethyl (meth) acrylamide, 4-acryloylmorpholine, (Meth) acrylamide, N, N-dimethylacrylamide and N, N-diethylacrylamide are preferred, and N, N-diethylacrylamide is particularly preferred.
- general formula (IV) examples include styrene, ⁇ -methylstyrene, N-vinylpyrrolidone and the like. Among them, styrene and ⁇ -methylstyrene are preferable, and styrene is particularly preferable.
- the alkyl group having 1 to 20 carbon atoms in R 32 of the general formula (V) may be linear, branched or cyclic.
- Examples of the hydroxylalkyl group having 1 to 10 carbon atoms in R 32 of the general formula (V) include a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a hydroxypentyl group, a hydroxyhexyl group, a hydroxyheptyl group, Examples thereof include a hydroxyoctyl group, a hydroxynonyl group, and a hydroxydecyl group.
- Examples of the halogenated alkyl group having 1 to 10 carbon atoms in R 32 of the general formula (V) include a chloromethyl group, a chloroethyl group, a chloro n-propyl group, a chloroisopropyl group, a chloro n-butyl group, and a chloro tert-butyl group.
- chloro-n-pentyl group chloro-n-hexyl group, chloro-n-heptyl group, chloro-n-octyl group, chloro-n-nonyl group, chloro-n-decyl group, methyl fluoride group, fluorine Ethyl fluoride group, fluoride-n-propyl group, isopropyl fluoride group, fluoride-n-butyl group, fluoride-tert-butyl group, fluoride-n-pentyl group, fluoride-n-hexyl group, fluorine Fluorinated n-heptyl group, fluorinated n-octyl group, fluorinated n-nonyl group, fluorinated n-decyl group and the like.
- Examples of the alkylcycloalkyl group having 1 to 10 carbon atoms in R 32 of the general formula (V) include a methylcyclohexyl group, an ethylcyclohexyl group, a propylcyclohexyl group, and a butylcyclohexyl group.
- Examples of the halogenated cycloalkyl group having 6 to 7 carbon atoms in R 32 of the general formula (V) include a chlorocyclohexyl group, a fluorinated cyclohexyl group, a bromocyclohexyl group, a chlorocycloheptyl group, a fluorinated cycloheptyl group, and a bromocycloheptyl group. Groups and the like.
- Examples of the aryl group having 6 to 10 carbon atoms in R 32 of the general formula (V) include a phenyl group and a naphthyl group.
- Examples of the aryl group having 6 to 10 carbon atoms having a substituent of an alkyl group having 1 to 6 carbon atoms in R 32 of the general formula (V) include a methylphenyl group, an ethylphenyl group, an n-propylphenyl group, and n-butyl. Examples thereof include a phenyl group, an n-pentylphenyl group, and an n-hexylphenyl group.
- Examples of the halogenated aryl group having 6 to 10 carbon atoms in R 32 of the general formula (V) include a chlorophenyl group, a phenyl fluoride group, a chloronaphthyl group, and a fluorinated naphthyl group.
- Preferred specific examples of the general formula (V) include maleic anhydride, maleimide, N-methylmaleimide, N-ethylmaleimide, N-butylmaleimide, N-octylmaleimide, N-dodecylmaleimide, N- (2-ethylhexyl) Maleimide, N- (2-hydroxyethyl) maleimide, N- (2-chlorohexyl) maleimide, N-cyclohexylmaleimide, N- (2-methylcyclohexyl) maleimide, N- (2-ethylcyclohexyl) maleimide, N- ( 2-chlorocyclohexyl) maleimide, N-phenylmaleimide, N- (2-methylphenyl) maleimide, N- (2-ethylphenyl) maleimide, N- (2-chlorophenyl) maleimide, etc., among which N-phenyl Maleimide is preferred.
- copolymer of the present invention examples include the following combinations of monomer units, among which combinations 1, 5, 6 and 7 are preferable.
- compound 2 represented by general formula (II) is represented by 2 Those containing types are preferred.
- the weight ratio of the monomer unit derived from the compound represented by general formula (I) and the monomer unit derived from the compound represented by general formula (II), general formula (III), general formula (IV) or general formula (V) is The monomer unit derived from the compound represented by the general formula (I) is usually 1 to 90% by weight, preferably 5%, based on the total weight of the obtained polymer. ⁇ 85% by weight.
- the polymer of the present invention is produced, for example, as follows. That is, the polymer of the present invention can be obtained by subjecting the compound of the present invention obtained as described above to a polymerization reaction known per se.
- the polymer of the present invention is a copolymer
- the compound of the present invention and the compound represented by the general formula (II), the general formula (III), the general formula (IV) or the general formula (V) are used during the polymerization reaction.
- One or two of these may be mixed so that the ratio of monomer units derived from the respective monomers in the finally obtained polymer is as described above, and then polymerized.
- the polymerization reaction is performed as follows, for example. That is, a compound represented by general formula (I) having an anion according to the present invention, or a compound represented by general formula (I) having an anion according to the present invention and general formula (II), general formula (III), 1 to 2 kinds of the compounds represented by the general formula (IV) or the general formula (V) are mixed with an appropriate solvent having a volume of 1 to 10 times the total volume thereof, for example, toluene, 1,4-dioxane, tetrahydrofuran, isopropanol , Methyl ethyl ketone, propylene glycol monomethyl ether acetate, etc., and 0.01 to 30% by weight of a polymerization initiator such as azoisobutyronitrile, 2,2′-azobis (2,4 -Dimethylvaleronitrile), 2,2'-azobis (2-methylpropionate), 2,2'-azobis (2-methylbutyronitrile), benzoic per
- the compound of the present invention has the cationic rhodamine derivative according to the present invention and the ethylenically unsaturated bond according to the present invention, and also has the anion according to the present invention as a counter anion.
- Specific examples of the compound of the present invention include compounds represented by the above general formula (I). Specific examples, preferred and preferred combinations of R 1 to R 7 , A 1 , A 2 , and An ⁇ in the general formula (I) are the same as those described in the above section [Polymer of the present invention]. Is mentioned.
- the compound of the present invention is produced, for example, as follows.
- a ′ 1 is an alkylene group having 1 to 21 carbon atoms having at least one of —O— and an arylene group in the chain; Represents an alkylene group, and Epo represents 3,4-epoxycyclohexyl or an epoxy group.
- the compound represented by the general formula (I-III) has the electron-withdrawing property according to the present invention.
- a salt of an anion containing an aryl group having a substituent for example, sodium salt, potassium salt, lithium salt, etc. of the anion
- an appropriate solvent such as dichloromethane at 10 to 50 ° C. for 10 to 120 minutes.
- the compound of the present invention can be obtained by performing anion exchange reaction of an anion.
- examples of the anion represented by Z ⁇ include Cl ⁇ , NO 3 ⁇ , SO 4 ⁇ , PO 4 ⁇ and the like. Or an anion according to the present invention.
- Preferred examples of the combination of R 1 to R 6 in the general formula (II) include the same combinations as those described in the section of the general formula (I).
- Preferred combinations of R 7 , A 1 and A 2 in the general formula (I-II) include the same combinations as those described in the section of the general formula (I).
- the amount of the compound represented by the general formula (I-II) is 1 to 5 mol times the rhodamine derivative represented by the general formula (II), The amount is preferably 1 to 2 mole times.
- the dehydrating condensing agent is not particularly limited as long as it is generally used as a dehydrating condensing agent.
- inorganic dehydrating agents such as diphosphorus pentoxide and anhydrous zinc chloride; for example, dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-ethyl-3
- Carbodiimides such as-(3-dimethylaminopropylcarbodiimide) hydrochloride; for example, polyphosphoric acid, acetic anhydride, sulfuric acid, carbonyldiimidazole, p-toluenesulfonic acid and the like, and carbodiimides are preferred.
- the amount of the dehydrating condensing agent to be used is 1 to 10 mol times, preferably 1 to 5 mol times based on the compound represented by the general formula (I-II).
- a catalyst such as dimethylaminopyridine may be used in order to improve the efficiency of the dehydrating condensing agent.
- the amount of the catalyst used is 0.1 to 10 mole times the compound represented by the general formula (I-II).
- the reaction for obtaining the compound represented by the general formula (I-III) is usually carried out by reacting in a reaction solvent at 10 to 50 ° C. for 5 to 24 hours.
- the reaction solvent include ethers such as diethyl ether, diisopropyl ether, ethyl methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane; for example, acetone, dimethyl ketone, methyl ethyl ketone, diethyl ketone, 2-hexanone, t-butyl.
- Ketones such as methyl ketone, cyclopentanone, cyclohexanone; halogenated hydrocarbons such as chloromethane, methylene chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, chlorobenzene; carbonization such as n-hexane, benzene, toluene, xylene, etc.
- Hydrogen for example, esters such as ethyl acetate, butyl acetate and methyl propionate; nitriles such as acetonitrile; and amides such as N, N-dimethylformamide Etc., and among them halogenated hydrocarbons are preferable, dichloromethane is more preferable. These may be used alone or in appropriate combination of two or more.
- the amount of the reaction solvent used is usually 1 to 50 times, preferably 1 to 20 times the total volume of the rhodamine derivative represented by the general formula (II) and the compound represented by the general formula (I-II). It is.
- the general formula (I-IV) of A '1 in the compound represented by, -O- and a is at least one group of the alkylene group having 1 to 21 carbon atoms having in the chain an arylene group, in the A 1 - Examples thereof include the same alkylene groups having 1 to 21 carbon atoms having at least one O- or arylene group in the chain.
- Examples of the alkylene group having 1 to 9 carbon atoms of A ′ 1 in the compound represented by the general formula (I-IV) include the same as the alkylene group having 1 to 9 carbon atoms of A 1 .
- a preferable combination of R 7 , A ′ 1 and A 2 is a combination according to the preferable one of R 7 , A 1 and A 2 described in the section of the general formula (I). Is mentioned.
- the amount of the compound represented by the general formula (I-IV) to be used is 1 to 5 mol times, preferably 1 to 2 mol times that of the rhodamine derivative represented by the general formula (II).
- Examples of the catalyst used in the method of obtaining the general formula (I-III) using the compound represented by the general formula (I-IV) include tetraethylammonium bromide, tetrabutylammonium bromide, tetraethylammonium chloride, tetrabutylphosphonium bromide. And quaternary salt catalysts such as triphenylbenzylphosphonium chloride; amines such as triethylamine and tributylamine.
- the amount of the catalyst to be used is 1 to 10 mol times, preferably 1 to 5 mol times based on the compound represented by the general formula (I-I).
- the method for obtaining the general formula (I-III) using the compound represented by the general formula (I-IV) is usually carried out by reacting in a reaction solvent at 10 to 50 ° C. for 5 to 24 hours.
- the reaction solvent are the same as those described in the method for obtaining the general formula (I-III). These may be used alone or in appropriate combination of two or more.
- the amount of the reaction solvent used is usually 1 to 50 times, preferably 1 to 20 times the total volume of the rhodamine derivative represented by the general formula (II) and the compound represented by the general formula (I-III). It is.
- the coloring composition of the present invention contains at least one polymer or compound of the present invention. Since the colored composition can form an excellent colored cured film, it is used for forming a colored pixel such as a color filter used in a liquid crystal display (LCD) or a solid-state imaging device (CCD, CMOS, etc.), printing ink, It can be used for applications such as inkjet inks and paints. In particular, it can be suitably used for a color filter of a liquid crystal display device.
- the coloring composition of the present invention preferably contains at least one or more of the above-described polymers or compounds of the present invention, a polymerization initiator, a binder resin, and a radically polymerizable monomer or oligomer. , A silane coupling agent and a crosslinking agent may be included.
- the coloring composition contains 1 to 50%, preferably 5 to 30%, of the polymer or compound of the present invention relative to the weight of the coloring composition.
- the weight of a coloring composition here means the weight of the solid component except a solvent, and represents the same meaning hereafter.
- the polymerization initiator known thermal polymerization initiators and photopolymerization initiators can be used, and photopolymerization initiators are preferred. Specifically, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1- ON, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl-phenylketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one Acetophenones such as 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone; benzoins such as benzoin, benzoin isopropyl ether and benzoin isobutyl ether; 2,4,6-trimethylbenzoyldiphenylphosphine oxide Acylphos
- Benzophenone methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4,4'-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, Benzophenone series such as acrylated benzophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 3,3′-dimethyl-4-methoxybenzophenone; 2-isopropylthioxanthone, 2,4- Thioxanthone series such as dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone; Aminobenzophenone series such as Michler ketone, 4,4'-diethylaminobenzophenone; 1- [4- (phenylthio ) Phenyl] -1,2-octanedione 2- (o
- the above polymerization initiators may be used alone or in combination of two or more.
- the content thereof is 1 to 50% by weight, preferably 5 to 30% by weight, based on the weight of the coloring composition.
- binder resin examples include an ethylenically unsaturated monomer having at least one carboxyl group or hydroxyl group, or an ethylenically unsaturated monomer having an ethylenically unsaturated monomer and an aromatic hydrocarbon group or an aliphatic hydrocarbon group. And those having an epoxy group at the side chain or terminal of the copolymer, those having an acrylate added, and the like. These may be used alone or in combination of two or more.
- ethylenically unsaturated monomer having a carboxyl group examples include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, benzyl methacrylate, crotonic acid, ⁇ -chloroacrylic acid, ethacrylic acid and cinnamic acid; maleic acid , Unsaturated dicarboxylic acids (anhydrides) such as maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid; trivalent or higher unsaturated polycarboxylic acids (anhydrides) 2- (meth) acryloyloxyethyl hexahydrophthalic acid, 2-methacryloyloxyethyl 2-hydroxypropyl phthalate, 2-acryloyloxyethyl 2-hydroxyethyl phthalic acid and the like.
- unsaturated monocarboxylic acids such as acrylic acid, methacryl
- the content of the binder resin is 10% to 50% by weight, preferably 20% to 50% by weight, based on the weight of the coloring composition.
- radical polymerizable monomer or oligomer examples include polyethylene glycol diacrylate (having 2 to 14 ethylene groups), polyethylene glycol dimethacrylate (having 2 to 14 ethylene groups), and trimethylolpropane.
- the content of the radical polymerizable monomer or oligomer is usually 20% to 60% by weight, preferably 30% to 60% by weight, more preferably 40% to 60% by weight, based on the weight of the coloring composition. It is. In particular, when used with the compound of the present invention, if the radical polymerizable monomer or oligomer is 40 wt% to 60 wt%, a higher heat resistance effect can be obtained.
- the pigment may be any pigment used for producing a blue or green coloring pattern, and examples thereof include phthalocyanine pigments.
- phthalocyanine pigments include those containing magnesium, titanium, iron, cobalt, nickel, copper, zinc, and aluminum as a central metal.
- Pigment blue 79 C.I. I. Pigment green 7, C.I. I. Pigment green 36, C.I. I. Pigment green 37, C.I. I. Pigment green 58, chloroaluminum phthalocyanine, hydroxyaluminum phthalocyanine, aluminum phthalocyanine oxide, zinc phthalocyanine, C.I. I. Pigment blue 15, C.I. I. Pigment Blue 15: 6, Pigment Blue 15: 1, C.I. I. Pigment blue 15: 2, C.I. I. Pigment Green 58 is preferable. I. Pigment blue 15: 6, C.I. I. Pigment Green 58 is preferable.
- the content of the pigment is 10 to 50% by weight, preferably 10 to 30% by weight, based on the weight of the coloring composition.
- the coloring composition of the present invention contains the above pigment, it preferably contains a pigment dispersant.
- the pigment dispersant include polyamidoamine and salts thereof, polycarboxylic acid and salts thereof, high molecular weight unsaturated acid ester, modified polyurethane, modified polyester, modified poly (meth) acrylate, and (meth) acrylic copolymer. , Naphthalenesulfonic acid formalin condensate], polyoxyethylene alkyl phosphate ester, polyoxyethylene alkyl amine, alkanol amine and the like.
- the pigment dispersants may be used alone or in combination of two or more. The content thereof is usually 1 to 80% by weight, preferably 10 to 60% by weight, based on the weight of the pigment.
- the solvent may be appropriately selected according to the components contained in the coloring composition. Specifically, for example, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, oxy Methyl acetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-oxypropionate, ethyl 3-oxypropionate, 3-methoxypropionic acid Methyl, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, eth
- the silane coupling agent is used when bonded to a substrate such as glass.
- silane coupling agent conventionally known silane coupling agents generally used in this field can be used.
- the reactive organic functional group include an epoxy group, a thiol group, a hydroxyl group, an amino group, a ureido group, a vinyl group, Examples include silane coupling agents having an acryloyl group and the like.
- the silane coupling agent may be used in an amount of usually 0.1 to 10% by weight, preferably 1 to 5% by weight in the reaction solution.
- crosslinking agent examples include (a) an epoxy resin, (b) a melamine compound, a guanamine compound, a glycoluril compound substituted with at least one substituent selected from a methylol group, an alkoxymethyl group, and an acyloxymethyl group.
- a urea compound (c) a phenol compound, a naphthol compound, or a hydroxyanthracene compound substituted with at least one substituent selected from a methylol group, an alkoxymethyl group, and an acyloxymethyl group.
- Resins are preferred. There is no particular limitation as long as the film can be cured by a crosslinking reaction.
- substituents selected from a melamine compound, a guanamine compound, a glycoluril compound or a urea compound
- a methylol group, an alkoxymethyl group, and an acyloxymethyl group, substituted with a group examples thereof include naphthol compounds and hydroxyanthracene compounds, and among them, polyfunctional epoxy resins are preferable.
- the content of the crosslinking agent is 10% to 50% by weight, preferably 20% to 50% by weight, based on the weight of the coloring composition.
- the coloring composition of the present invention may contain a polymerization inhibitor, a surfactant, an additive and the like in addition to the above-described ones, and they are not particularly limited as long as they are known per se. There is no limitation as long as it is an amount usually used in this field.
- the coloring composition of the present invention is prepared by mixing the aforementioned components.
- Example 1 Synthesis of Dye Monomer M-2
- 11.8 g (0.020 mol) of dye monomer M-1 and lithium salt of tetrakis (pentafluorophenyl) boron (IV) 13 After adding 0.7 g (0.020 mol, manufactured by Tosoh Finechem Co., Ltd.), 150 ml of dichloromethane, and 150 ml of ion-exchanged water, the mixture was stirred at room temperature for 30 minutes to carry out a salt exchange reaction. After completion of the reaction, the organic layer was washed 4 times with about 150 ml of ion exchange water.
- Example 2 Synthesis of Dye Monomer M-3 Instead of 13.7 g of tetrakis (pentafluorophenyl) boron (IV) lithium salt, 4.0 g of 4-nitrobenzenesulfonic acid (0.020 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) was used. The compound was synthesized in the same manner as in Synthesis Example 2 except that it was used. As a result, 14.4 g (yield 94.7%) of a red viscous liquid in which chloride ions of the dye monomer M-1 were exchanged with 4-nitrobenzenesulfonate anions. This is designated as Dye Monomer M-3.
- Example 3 Synthesis of Dye Monomer M-4 Instead of 13.7 g of tetrakis (pentafluorophenyl) boron (IV) lithium salt, 5.4 g of sodium pentafluorobenzenesulfonate (0.020 mol, Wako Pure Chemical Industries, Ltd.)
- the product was synthesized in the same manner as in Synthesis Example 2 except that As a result, 15.0 g (yield 93.5%) of a red viscous liquid in which the chloride ion of the dye monomer M-1 was exchanged with a pentafluorobenzenesulfonate anion was obtained. This is designated as Dye Monomer M-4.
- Example 4 Synthesis of Dye Monomer M-5 Instead of 13.7 g of the tetrakis (pentafluorophenyl) boron (IV) lithium salt, 3.5 g of 4-fluorobenzenesulfonic acid (0.020 mol, manufactured by Sigma-Aldrich) The compound was synthesized in the same manner as in Synthesis Example 2 except that was used. As a result, 13.6 g (yield 93.0%) of a red viscous liquid in which the chloride ion of the dye monomer M-1 was exchanged with 4-fluorobenzenesulfonate anion. This is designated as Dye Monomer M-5.
- Synthesis Example 3 Synthesis of dye monomer M-7 3.8 g (0.020 mol) of p-toluenesulfonic acid monohydrate was used instead of 13.7 g of the lithium salt of tetrakis (pentafluorophenyl) boron (IV). Except for the above, synthesis was performed in the same manner as in Synthesis Example 2. as a result, As a result, 13.6 g (yield 91.0%) of a red viscous liquid in which the chloride ion of the dye monomer M-1 was exchanged with the p-toluenesulfonic acid anion was obtained. This is designated as Dye Monomer M-7.
- Example 6 Synthesis of dye monomer M-11 In a 500 ml round bottom flask equipped with a stirrer, 12.1 g (0.020 mol) of dye monomer M-10, tetrakis (pentafluorophenyl) boron (IV) After adding 13.7 g (0.020 mol, manufactured by Tosoh Finechem Co., Ltd.), 150 ml of dichloromethane, and 150 ml of ion-exchanged water, a salt exchange reaction was carried out by stirring at room temperature for 30 minutes. After completion of the reaction, the organic layer was washed 4 times with about 150 ml of ion exchange water.
- Example 7 Synthesis of Dye Polymer P-2 A 200 ml round bottom flask equipped with a stirrer, a cooling tube, a thermometer, and a nitrogen introducing tube was charged with 27.9 g of propylene glycol monomethyl ether acetate (manufactured by Wako Pure Chemical Industries, Ltd.) And heated under a nitrogen stream until the internal temperature reached 90 ° C.
- Examples 8 to 10 Synthesis of dye polymers P-3 to 5 Dye polymers were obtained in the same manner as in Example 1 except that the dye monomer M-3 was used instead of the dye monomer M-2. This is designated as Dye Polymer P-3. Similarly, dye polymers P-4 and P-5 were obtained using dye monomer M-4 or 5 instead of dye monomer M-2.
- Example 11 Synthesis of Dye Polymer P-8 (Synthesis of Polymer with High Dye Monomer Ratio) Propylene glycol monomethyl ether acetate 11.6 g (manufactured by Wako Pure Chemical Industries, Ltd.) is placed in a 200 ml round bottom flask equipped with a stirrer, cooling tube, thermometer and nitrogen introduction tube, and the internal temperature is reduced under a nitrogen stream. Heated to 90 ° C.
- Example 12 Synthesis of Dye Polymer P-9 A dye polymer was obtained in the same manner as in Example 1 except that the dye monomer M-9 was used instead of the dye monomer M-2. This is designated as Dye Polymer P-9.
- Example 13 Synthesis of Dye Polymer P-11 A dye polymer was obtained in the same manner as in Example 1, except that the dye monomer M-11 was used instead of the dye monomer M-2. This is designated as Dye Polymer P-11.
- Example 14 Synthesis of Dye Polymer P-12 (Synthesis of Polymer with High Dye Monomer Ratio) 9.3 g of propylene glycol monomethyl ether acetate (manufactured by Wako Pure Chemical Industries, Ltd.) is placed in a 100 ml round bottom flask equipped with a stirrer, a cooling tube, a thermometer, and a nitrogen introduction tube. Heated to 90 ° C.
- the nonvolatile content concentration of this polymer solution was 35.7%.
- Example 18 Synthesis of dye polymer P-16
- 50.1 g of benzyl methacrylate was changed to 32.1 g of methyl methacrylate and 18 g of diethylacrylamide (manufactured by Wako Pure Chemical Industries, Ltd.).
- Example 21 Evaluation of heat resistance of polymer (230 ° C., 0.5 hour)
- the heat resistance of the dye polymers P-2 to P-5, P-9 and P-11 obtained in Examples 5 to 8 was evaluated as follows. That is, the obtained dye polymers P-2 to P-5, P-9, and P-11 were each spin-coated on a 3-inch glass wafer (Eagle XG manufactured by Corning), and then heated on a hot plate heated to 90 ° C. And dried for 90 seconds to obtain a thin film having a thickness of 1 micron. Each thin film thus obtained was measured for absorbance ( ⁇ a) at the maximum absorption wavelength using a spectrophotometer (Spectrophotometer UV-2550 manufactured by Shimadzu Corporation), and then 30 minutes on a hot plate heated to 230 ° C.
- a spectrophotometer Spectrophotometer UV-2550 manufactured by Shimadzu Corporation
- Example 22 Evaluation of heat resistance of monomer (230 ° C., 0.5 hour)
- the heat resistance of the dye monomers M-2 to M-5, M-9 and M-11 obtained in Examples 1 to 6 was evaluated as follows. (1) Synthesis of polymer containing no dye 98.5 g of propylene glycol monomethyl ether acetate was placed in a 500 ml round bottom flask equipped with a stirrer, a cooling tube, a thermometer, and a nitrogen introducing tube, and the internal temperature was reduced under a nitrogen stream. Heated to 90 ° C.
- dye polymers P-2 to P-5, P-9 and P-11 of Example 21, and dye monomers M-2 to M-4, M-9 of Example 22 and M-11 was found to exhibit higher heat resistance than dye monomers M-1, M-6 and M-7, and dye polymers P-1, P-6, and P-7 in Comparative Examples 1 and 2. .
- the dye monomers M-1, M-6 and M-7 and the dye monomers M-2 to M-4, M-9 and M-11 have different anion components.
- Example 23 Evaluation of heat resistance of polymer (230 ° C., 1.5 hours) The same as Example 21 except that the heating time was 30 minutes and 90 minutes and dye polymers P-2 to P-4, P-9, P-10, P-11, P-13 to P-17 were used. The heat resistance of these polymers was evaluated by the method. The obtained results are shown in Table 2.
- Example 24 Evaluation of heat resistance of monomer (230 ° C., 1.5 hours) Dye monomers M-2 to 4, M-9, M-10 and M-11 were evaluated for heat resistance in the same manner as in Example 22 except that the heating time was changed to 90 minutes. The obtained results are shown in Table 2.
- Example 23 Example 24, Comparative Example 3 and Comparative Example 4, the heat resistance was evaluated by setting the heating time of the above Example 21, Example 22, Comparative Example 1 and Comparative Example 2 to 90 minutes, respectively. .
- Table 2 As in the case of the heating time of 30 minutes, the dye polymers P-2 to P-4, P-9 and P-11 of Example 23 and the dye monomer of Example 24 were used.
- M-2 to M-4, M-9 and M-11 are dye polymers P-1, P-6, P-7, and dye monomers M-1, M-6, M, which are different in anionic component from them. Each showed higher heat resistance than -7.
- the resist solution was spin-coated on a 3-inch glass wafer, and then dried for 100 seconds on a hot plate heated to 100 ° C. to obtain a thin film having a thickness of 1.5 ⁇ m.
- Each of the obtained thin films was irradiated with a light amount of 200 mJ / cm 2 using a high-pressure mercury lamp, immersed in a 0.5% KOH aqueous solution for 90 seconds, washed with ion-exchanged water, and further heated to 230 ° C. Heated on hot plate for 30 minutes.
- Example 26 Evaluation of solvent resistance of cured film of dye polymer P-13 Dye polymer in the same manner as in Example 25 except that dye monomer P-13 was used instead of dye polymer P-12. The solvent resistance of P-13 was evaluated. The obtained results are shown in Table 3 together with the results of Example 25.
- Example 28 Evaluation of solvent resistance of cured film of dye monomer M-11 Dye monomer in the same manner as in Example 27 except that dye monomer M-11 was used instead of dye monomer M-2. The solvent resistance of M-11 was evaluated. The resist composition and solvent resistance results are shown in Table 3 together with the results of Examples 25 to 27.
- KAYARAD DPHA Dipentaerythritol hexaacrylate (Nippon Kayaku Co., Ltd.)
- IRGACURE 369 2-Benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 (manufactured by BASF)
- LS-3380 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)
- PGMEA Propylene glycol monomethyl ether acetate
- NMP N-methyl-2-pyrrolidone
- a pattern is usually formed on a substrate with a polymer containing the first color and then a pattern containing the polymer containing the second color. At this time, the patterned polymer is exposed to the solvent of the polymer containing the second color. At this time, if the dye is eluted from the patterned polymer into the solvent, it causes a color mixture with the second color simultaneously with a decrease in color density. Therefore, the solvent resistance of the cured polymer is an important factor. As is apparent from Table 3, when P-12, P-13, M-2 or M-11 is used as a dye, the solvent resistance to the solvent is very high, and the residual ratio of the dye is approximately 90% or more. there were.
- M-12 used in Comparative Example 5 had a low solvent resistance of 43%. This was thought to be due to the fact that the anion was chloride ion and rhodamine B not having a polymerizable group, so that it was not immobilized in the cured film.
- the dye polymers P-12 and P-13 used in Examples 25 and 26 were obtained by polymerizing the dye monomers M-2 and M-11 of Examples 27 and 28, respectively. However, it was found that the solvent resistance was higher when added in the form of a dye polymer than when added to the resist in the form of a dye monomer.
- Example 35 Synthesis of dye monomer M-21 (1) Synthesis of 4-hydroxybutyl methacrylate 135 g of 1,4-butanediol (1.5 mol, manufactured by Wako Pure Chemical Industries, Ltd.), 96 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.5 mol, manufactured by Toyobo Co., Ltd.) and 1.2 g of N, N-dimethylaminopyridine (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in 2 L of dichloromethane.
- Example 36 Synthesis of Dye Monomer M-22 (1) Synthesis of 6-hydroxyhexyl methacrylate 177 g of 1,6-hexanediol (1.5 mol, manufactured by Wako Pure Chemical Industries, Ltd.), 96 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.5 mol, manufactured by Toyobo Co., Ltd.) and 12 g of N, N-dimethylaminopyridine (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in 2 L of dichloromethane, and 43 g of methacrylic acid (0.5 mol, Wako Pure) Yaku Kogyo Co., Ltd.) was added dropwise and stirred at room temperature for 12 hours.
- Example 37 Synthesis of Dye Monomer M-23 (1) Synthesis of 8-hydroxyoctyl methacrylate 1,8-octanediol 219 g (1.5 mol, manufactured by Wako Pure Chemical Industries, Ltd.), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 96 g (0.5 mol, manufactured by Toyobo Co., Ltd.) and 12 g of N, N-dimethylaminopyridine (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in 2 L of dichloromethane, and 43 g of methacrylic acid (0.5 mol, Wako Pure) Yaku Kogyo Co., Ltd.) was added dropwise and stirred at room temperature for 12 hours.
- methacrylic acid 0.5 mol, Wako Pure
- Example 38 Synthesis of dye monomer M-24 (1) Synthesis of 10-hydroxydecyl methacrylate 87 g of 1,10-decanediol (0.5 mol, manufactured by Wako Pure Chemical Industries, Ltd.), 43 g of methacrylic acid (0.5 mol, manufactured by Wako Pure Chemical Industries, Ltd.) ), P-toluenesulfonic acid 5.1 g (manufactured by Wako Pure Chemical Industries, Ltd.), p-methoxyphenol 0.6 g (manufactured by Wako Pure Chemical Industries, Ltd.) and 150 ml of hexane were mixed and reflux dehydrated for 15 hours. .
- Example 39 Synthesis of Dye Monomer M-25 (1) Synthesis of 12-hydroxydodecyl methacrylate 101 g of 1,12-dodecanediol (0.5 mol, manufactured by Wako Pure Chemical Industries, Ltd.), 43 g of methacrylic acid (0.5 mol, manufactured by Wako Pure Chemical Industries, Ltd.) ), P-toluenesulfonic acid 5.1 g (manufactured by Wako Pure Chemical Industries, Ltd.), p-methoxyphenol 0.6 g (manufactured by Wako Pure Chemical Industries, Ltd.) and 150 ml of hexane were mixed and reflux dehydrated for 15 hours. .
- Example 40 Synthesis of Dye Polymer P-20 Into a 200 ml round bottom flask equipped with a stirrer, a condenser, a thermometer, and a nitrogen introduction tube, 27.9 g of propylene glycol monomethyl ether acetate (manufactured by Wako Pure Chemical Industries, Ltd.) And heated under a nitrogen stream until the internal temperature reached 90 ° C.
- Examples 41 to 45 Synthesis of Dye Polymers P-21 to 25 The experiment was performed in the same manner as in Example 40 except that 48.0 g of dye monomers M-21 to M25 were used instead of 48.0 g of dye monomer M-2. Five types of dye polymers were obtained. These are designated as dye polymers P-21, P-22, P-23, P-24, and P-25, respectively. Further, as a result of gel permeation chromatography analysis of the obtained polymer solutions of P-21 to P-25, the amount of unreacted dye monomer contained was 15.2%, 4.9% in area%, respectively. They were 3.2%, 0.9%, and 5.3%. The results are shown in Table 5 together with the results of Example 40.
- Example 46 Evaluation of heat resistance of dye polymers P-20 to 25 (230 ° C., 0.5 hour) The heat resistance of the dye polymers P-21 to P-25 was evaluated in the same manner as in Example 21 except that P-21 to P-25 were used as the dye polymers. The results are shown in Table 5 together with the unreacted monomer amounts of Examples 40 to 45.
- the polymer of the present invention can reduce the residual monomer by increasing the number of atoms between the double bond (polymerizable group) and the benzene ring (phenyl group) in the contained dye monomer.
- the number of atoms between the double bond and the benzene ring is 10 or more, the residual monomer is greatly reduced, 14 is the least residual monomer, but 16 is conversely an increase in the residual monomer. I understood. This was thought to be due to an improvement in the decrease in polymerizability due to steric hindrance of the dye.
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Abstract
Description
また、本発明のポリマー又は化合物は、これらを着色剤としてレジスト材料に混合して用いた場合、染料(着色剤)の溶出が少ないという効果を奏する。そのため、従来の着色組成物と比較して、色濃度の低下や混色等の問題を有さない優れた着色組成物の提供を可能とする。
カチオン性ローダミン誘導体が有するアニオン(以下、本発明に係るアニオンと略記する場合がある)におけるアニオン基としては、例えばスルホン酸アニオン基、4級ホウ素アニオン基、硝酸イオン、燐酸イオン等が挙げられ、スルホン酸アニオン基、4級ホウ素アニオン基が好ましく、4級ホウ素アニオン基がより好ましい。
mは、通常1~5の整数であるが、R41がハロゲン原子の場合は2~5が好ましく、3~5がより好ましく、5が更に好ましい。R41がニトロ基の場合は1~3が好ましく、1がより好ましい。R41がハロゲン化アルキル基の場合は、1~5が好ましい。
一般式(XIII)における、R41及びmの組合せとしては、例えば下記表記載のものが挙げられる。
本発明に係るカチオン性ローダミン誘導体は、上記本発明に係るアニオンをカウンターアニオンとして有するものであり、例えば下記一般式(VII)で示される化合物が挙げられる。
[式中、R1~R4はそれぞれ独立して、水素原子、炭素数1~30のアルキル基、炭素数1~6のヒドロキシアルキル基、炭素数1~6のスルホアルキル基、炭素数2~7のカルボキシアルキル基、炭素数2~7のシアノアルキル基、炭素数2~6のアルコキシアルキル基、炭素数1~6のハロゲノアルキル基、置換基を有する又は無置換のフェニル基またはベンジル基を表し、R5~R6はそれぞれ独立して水素原子またはメチル基を表す。An-は、本発明に係るアニオン(電子吸引性の置換基を有するアリール基及びアニオン基を含むアニオン)を表す。]
本発明のポリマーは、上記本発明に係るカチオン性ローダミン誘導体と本発明に係るエチレン性不飽和結合とを有する化合物由来のモノマー単位を有するポリマーである。
(式中、R1~R6及びAn-は上記と同じ。R7は、水素原子またはメチル基を表し、A1は、-O-、-OCO-、-COO-又はアリーレン基の少なくとも1つの基を鎖中に有し、且つ、ヒドロキシル基を置換基として有する炭素数1~21のアルキレン基、-O-、-OCO-、-COO-又はアリーレン基の少なくとも1つの基を鎖中に有する炭素数1~21のアルキレン基、炭素数1~9のアルキレン基、或いは、水酸基を置換基として有する炭素数1~6のアルキレン基を表し、A2は-NH-または-O-を表す。)
(式中、R51は、ヒドロキシル基を置換基として有する炭素数4~7のシクロアルキレン基を表し、p1は、1~3の整数を表す。)、下記一般式(VI-II)で示される基
で示される基(式中、R52は、ヒドロキシル基を置換基として有する炭素数1~6のアルキレン基を表し、p2は、1~3の整数を表す。)等が挙げられる。
-C6H9(OH)-CH2-、
-C6H9(OH)-C2H5-、
-C6H9(OH)-C3H7-、
等が挙げられる。
-CH2-CH(OH)-CH2-O-(CH2)2-、
-CH2-CH(OH)-CH2-O-(CH2)3-、
-CH2-CH(OH)-CH2-O-(CH2)4-、
等が挙げられる。
-(CH2)p3-OCO-R53-COO-(CH2)p4- (VII-I)
(式中、R53は、フェニレン基、シクロアルキレン基を表し、p3及びp4は、それぞれ独立して、1~3の整数を表す。)、
一般式(VII-II)で示される基
-(C2H4O)p5-(CH2)p6- (VII-II)
(式中、p5は、1~9の整数を表し、p6は、1~3の整数を表す。)、
一般式(VII-III)で示される基
-(CH2CH(CH3)O)p7-R54- (VII-III)
(式中、p7は1~9の整数を表し、R54は、分枝状の炭素数1~3のアルキレン基等が挙げられる。)等が挙げられる。
-CH2CH2-O-CO-C6H4-CO-O-CH2CH2-、
-CH2CH2-O-CO-C6H10-CO-O-CH2CH2-
等が挙げられる。
-(CH2CH2O)-CH2CH2-、-(CH2CH2O)2-CH2CH2-
-(CH2CH2O)3-CH2CH2-、-(CH2CH2O)4-CH2CH2-
-(CH2CH2O)5-CH2CH2-、-(CH2CH2O)6-CH2CH2-
-(CH2CH2O)7-CH2CH2-、-(CH2CH2O)8-CH2CH2-
-(CH2CH2O)9-CH2CH2-、
等が挙げられる。
-(CH2CH(CH3)O)-CH2CH(CH3)-
-(CH2CH(CH3)O)2-CH2CH(CH3)-
-(CH2CH(CH3)O)3-CH2CH(CH3)-
-(CH2CH(CH3)O)4-CH2CH(CH3)-
-(CH2CH(CH3)O)5-CH2CH(CH3)-
-(CH2CH(CH3)O)6-CH2CH(CH3)-
-(CH2CH(CH3)O)7-CH2CH(CH3)-
-(CH2CH(CH3)O)8-CH2CH(CH3)-
-(CH2CH(CH3)O)9-CH2CH(CH3)-
-CH(CH3)CH2-O-CH2CH(CH3)-、
等が挙げられる。
基、炭素数7~13のアリールアルキル基、炭素数2~9のアルコキシアルキル基、炭素数3~9のアルコキシアルコキシアルキル基、炭素数7~13のアリールオキシアルキル基、炭素数5~7のモルホリノアルキル基、炭素数3~9のトリアルキルシリル基、酸素原子を有する又は酸素原子を有さない炭素数6~10の脂環式炭化水素基、炭素数3~9のジアルキルアミノアルキル基、炭素数1~18のフッ化アルキル基、又は炭素数1~6のN-アルキレンフタルイミド基、下記一般式(II-I)で示される基
下記一般式(II-II)で示される基
1~3のアルキル基としては、上記R13と同じものが挙げられる。
本発明のポリマーは、例えば以下の如く製造される。即ち、上記の如く得られた本発明の化合物を自体公知の重合反応に付すことにより、本発明のポリマーを得ることができる。本発明のポリマーがコポリマーの場合には、重合反応の際に、上記本発明の化合物と一般式(II)、一般式(III)、一般式(IV)又は一般式(V)で示される化合物の1~2種とを、最終的に得られるポリマー中の各モノマーに由来するモノマー単位の比率が上記の如くなるように混合した後、重合させればよい。
本発明の化合物は、上記本発明に係るカチオン性ローダミン誘導体と上記本発明に係るエチレン性不飽和結合とを有し、且つ、上記本発明に係るアニオンをカウンターアニオンとして有するものである。
本発明の化合物は、例えば以下の如く製造される。
本発明の着色組成物は、上記本発明のポリマー又は化合物を少なくとも1種含むものである。該着色組成物は、優れた着色硬化膜を形成することができるため、液晶表示装置(LCD)や固体撮像素子(CCD、CMOS等)に用いられるカラーフィルター等の着色画素形成用途、印刷インキ、インクジェットインキ、および塗料等の用途に用いることができる。特に、液晶表示装置のカラーフィルター用として好適に用いることができる。
上記ラジカル重合性モノマーまたはオリゴマーの含有量は、着色組成物の重量に対して、通常20重量%~60重量%、好ましくは30重量%~60重量%、より好ましくは40重量%~60重量%である。特に、本発明の化合物と用いる場合には、ラジカル重合性モノマーまたはオリゴマーを40重量%~60重量%とすると、より高い耐熱性効果を奏することができる。
架橋反応により膜硬化を行なえるものであれば、特に限定されず、例えば、例えば、(a)エポキシ樹脂、(b)メチロール基、アルコキシメチル基、及びアシロキシメチル基から選ばれる少なくとも1つの置換基で置換された、メラミン化合物、グアナミン化合物、グリコールウリル化合物又はウレア化合物、(c)メチロール基、アルコキシメチル基、及びアシロキシメチル基から選ばれる少なくとも1つの置換基で置換された、フェノール化合物、ナフトール化合物又はヒドロキシアントラセン化合物、が挙げられ、中でも、多官能エポキシ樹脂が好ましい。
攪拌装置を備えた2Lの丸底フラスコに、ローダミンB47.9g(0.10mol、和光純薬工業(株)製)、ジクロロメタン500ml、ヒドロキシエチルメタクリレート 15.6g(0.12mol、和光純薬工業(株)製)、4‐ジメチルアミノピリジン4.9g(0.04mol、和光純薬工業(株)製)、1‐エチル‐3‐(3‐ジメチルアミノプロピル)カルボジイミド塩酸塩32.6g(0.17mol、東洋紡(株)製)を加え、室温で24時間攪拌して反応させた。反応終了後、有機層を約500mlのイオン交換水で洗浄した。次いで、硫酸ナトリウム50g加えて脱水し、重合禁止剤としてp‐メトキシフェノール10mg(和光純薬工業(株)製)を加えて減圧下で溶媒を留去し、赤色の固体44g(収率74.6%)を得た。これを染料モノマーM‐1とする。
撹拌装置を備えた500mlの丸底フラスコに、染料モノマーM‐1 11.8g(0.020mol)、テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩 13.7g(0.020mol、東ソー・ファインケム(株)製)、ジクロロメタン150ml、イオン交換水150mlを加えた後、室温で30分間攪拌することにより、塩交換反応を行った。反応終了後、有機層を約150mlのイオン交換水で4回洗浄した。次いで、p‐メトキシフェノール5mg(和光純薬工業(株)製)を加え、減圧下で濃縮し、染料モノマーM‐1の塩化物イオンがテトラキス(ペンタフルオロフェニル)ホウ素(IV)アニオンに交換された赤色の固体22.8g(収率92.3%)を得た。これを染料モノマーM-2とする。
テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩13.7gの代わりに4‐ニトロベンゼンスルホン酸4.0g(0.020mol、東京化成(株)製)を用いた以外は、合成例2と同様の方法で合成した。その結果、染料モノマーM‐1の塩化物イオンが4‐ニトロベンゼンスルホン酸アニオンに交換された、赤色粘調の液体14.4g(収率94.7%)を得た。これを染料モノマーM‐3とする。
テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩13.7gの代わりにペンタフルオロベンゼンスルホン酸ナトリウム5.4g(0.020mol、和光純薬工業(株)製)を用いた以外は、合成例2と同様の方法で合成した。その結果、染料モノマーM‐1の塩化物イオンがペンタフルオロベンゼンスルホン酸アニオンに交換された、赤色粘調の液体15.0g(収率93.5%)を得た。これを染料モノマーM‐4とする。
テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩13.7gの代わりに4-フルオロベンゼンスルホン酸3.5g(0.020mol、シグマアルドリッチ(株)製)を用いた以外は、合成例2と同様の方法で合成した。その結果、染料モノマーM‐1の塩化物イオンが4-フルオロベンゼンスルホン酸アニオンに交換された、赤色粘調の液体13.6g(収率93.0%)を得た。これを染料モノマーM‐5とする。
テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩13.7gの代わりにドデシルベンゼンスルホン酸6.6g(0.020mol)を用いた以外は、合成例2と同様の方法で合成した。その結果、染料モノマーM‐1の塩化物イオンがドデシルベンゼンスルホン酸アニオンに交換された、赤色粘調の液体17.0g(収率93.4%)を得た。これを染料モノマーM‐6とする。
テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩13.7gの代わりにp-トルエンスルホン酸・1水和物3.8g(0.020mol)を用いた以外は、合成例2と同様の方法で合成した。その結果、
染料モノマーM‐1の塩化物イオンがp-トルエンスルホン酸アニオンに交換された、赤色粘調の液体13.6g(収率91.0%)を得た。これを染料モノマーM‐7とする。
(1)ローダミン6Gの加水分解
攪拌装置を備えた丸底フラスコに、ローダミン6G(化合物1)12.0g(0.025mol、和光純薬工業(株)製)、水酸化ナトリウム1.1g(0.026mol、和光純薬工業(株)製)及びエタノール80mL(和光純薬工業(株)製)を加え、70℃で12時間反応させた。減圧濃縮によって溶媒を留去した後、イオン交換水130mLを加え、1mol/L HCl水溶液をpHが2付近になるまで滴下し、1時間撹拌した。析出した結晶をろ取して、ローダミン6Gの加水分解体(化合物2)10.3g(収率91%)を得た。
攪拌装置を備えた丸底フラスコに、ローダミン6Gの加水分解体(化合物2)10.2g(0.023mol)、2-ヒドロキシエチルメタクリレート(化合物3)3.5g(0.027mol、和光純薬工業(株)製)、4‐ジメチルアミノピリジン0.8g(0.007mol、和光純薬工業(株)製)、1‐エチル‐3‐(3‐ジメチルアミノプロピル)カルボジイミド塩酸塩7.4g(0.038mol、東洋紡(株)製)、ジクロロメタン90mL(和光純薬工業(株)製)を加え、室温で24時間反応させた。反応終了後、イオン交換水を加えて洗浄し、減圧濃縮によって溶媒を留去した。さらにシリカゲルカラムで精製し、減圧濃縮にて溶媒を留去し、褐色固体の染料モノマーM-8(化合物4)を12.1g(収率95%)得た。
撹拌装置を備えた丸底フラスコに、染料モノマーM-8(化合物4)9.0g(0.016mol)、テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩10.9g(0.016mol、東ソー・ファインケム(株)製)、ジクロロメタン110ml(和光純薬工業(株)製)及びイオン交換水30mlを加えた後、室温で3時間反応させ、塩交換反応を行った。反応終了後、水層を分液し、イオン交換水で洗浄した。その後、水層を減圧下で濃縮し、染料モノマーM-8の塩化物イオンがテトラキス(ペンタフルオロフェニル)ホウ素(IV)アニオンに交換された褐色固体(化合物5)19.3g(収率100%)を得た。これを染料モノマーM-9とする。
攪拌装置を備えた2Lの丸底フラスコに、ローダミンB47.9g(0.10mol、和光純薬工業(株)製)、ジクロロメタン500ml、ヒドロキシブチルアクリレート17.3g(0.12mol、和光純薬工業(株)製)、4‐ジメチルアミノピリジン4.9g(0.04mol、和光純薬工業(株)製)、1‐エチル‐3‐(3‐ジメチルアミノプロピル)カルボジイミド塩酸塩32.6g(0.17mol、東洋紡(株)製)を加え、室温で24時間攪拌して反応させた。反応終了後、有機層を約500mlのイオン交換水で洗浄した。次いで、硫酸ナトリウム50g加えて脱水し、重合禁止剤としてp‐メトキシフェノール10mg(和光純薬工業(株)製)を加えて減圧下で溶媒を留去し、赤色の固体48.5g(収率80.2%)を得た。これを染料モノマーM‐10とする。
撹拌装置を備えた500mlの丸底フラスコに、染料モノマーM‐10 12.1g(0.020mol)、テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩 13.7g(0.020mol、東ソー・ファインケム(株)製)、ジクロロメタン150ml、イオン交換水150mlを加えた後、室温で30分間攪拌することにより、塩交換反応を行った。反応終了後、有機層を約150mlのイオン交換水で4回洗浄した。次いで、p‐メトキシフェノール5mg(和光純薬工業(株)製)を加え、減圧下で濃縮し、染料モノマーM‐10の塩化物イオンがテトラキス(ペンタフルオロフェニル)ホウ素(IV)アニオンに交換された赤色の固体23.5g(収率93.9%)を得た。これを染料モノマーM-11とする。
撹拌装置を備えた500mlの丸底フラスコに、ローダミンB 9.6g(0.020mol)、テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩 13.7g(0.020mol、東ソー・ファインケム(株)製)、ジクロロメタン150ml、イオン交換水150mlを加えた後、室温で30分間攪拌することにより、塩交換反応を行った。反応終了後、有機層を約150mlのイオン交換水で4回洗浄した。次いで、減圧下で濃縮し、ローダミンBの塩化物イオンがテトラキス(ペンタフルオロフェニル)ホウ素(IV)アニオンに交換された赤色の固体21.1g(収率94.0%)を得た。これを染料モノマーM-12とする。
攪拌装置、冷却管、温度計、窒素導入管を備えた200mlの丸底フラスコに、プロピレングリコールモノメチルエーテルアセテート27.9g(和光純薬工業(株)製)を入れ、窒素気流下で内温が90℃になるまで加熱した。次いで、染料モノマーM-2 3.0g、ベンジルメタクリレート50.1g(和光純薬工業(株)製)、メタクリル酸6.9g(和光純薬工業(株)製)、ジメチル2,2´‐アゾビス(2-メチルプロピオネート)(和光純薬工業(株)製重合開始剤V‐601)9.6g、及びプロピレングリコールモノメチルエーテルアセテート27.9g(和光純薬工業(株)製)を混合した溶液を、2時間かけて丸底フラスコに滴下した。その後、得られた溶液を90℃で2時間反応させた。反応後、室温まで冷却し、プロピレングリコールモノメチルエーテルアセテート48.6gを加えて希釈し、染料ポリマーを得た。これを染料ポリマーP-2(重量比:染料モノマーM-2/ベンジルメタクリレート/メタクリル酸=3.0/50.1/6.9)とする。
染料モノマーM-2の代わりに染料モノマーM-3を用いた以外は、実施例1と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-3とする。また、同様に、染料モノマーM-2の代わりに染料モノマーM-4又は5を用い、染料ポリマーP-4およびP-5を得た。
染料モノマーM-2の代わりに染料モノマーM-1、6又は7を用いた以外は、実施例1と同様の方法により、染料ポリマーを得た。これらをそれぞれ染料ポリマーP-1、P-6、P-7とする。
攪拌装置、冷却管、温度計、窒素導入管を備えた200mlの丸底フラスコに、プロピレングリコールモノメチルエーテルアセテート11.6g(和光純薬工業(株)製)を入れ、窒素気流下で内温が90℃になるまで加熱した。次いで、染料モノマーM-2 20g、ベンジルメタクリレート2.1g(和光純薬工業(株)製)、メタクリル酸2.9g(和光純薬工業(株)製)、ジメチル2,2´‐アゾビス(2-メチルプロピオネート)(和光純薬工業(株)製重合開始剤V‐601)4g、及びプロピレングリコールモノメチルエーテルアセテート11.6g(和光純薬工業(株)製)を混合した溶液を、2時間かけて丸底フラスコに滴下した。その後、得られた溶液を90℃で2時間反応させた。反応後、室温まで冷却し、プロピレングリコールモノメチルエーテルアセテート20.2gを加えて希釈し、染料ポリマーを得た。これを染料ポリマーP-8(重量比:染料モノマーM-2/ベンジルメタクリレート/メタクリル酸=80/8.5/11.5)とする。
染料モノマーM-2の代わりに染料モノマーM-9を用いた以外は、実施例1と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-9とする。
染料モノマーM-2の代わりに染料モノマーM-11を用いた以外は、実施例1と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-11とする。
攪拌装置、冷却管、温度計、窒素導入管を備えた100mlの丸底フラスコに、プロピレングリコールモノメチルエーテルアセテート9.3g(和光純薬工業(株)製)を入れ、窒素気流下で内温が90℃になるまで加熱した。次いで、染料モノマーM-2 16g、ベンジルメタクリレート4g(和光純薬工業(株)製)、ジメチル2,2´‐アゾビス(2-メチルプロピオネート)(和光純薬工業(株)製重合開始剤V‐601)3.2g、及びプロピレングリコールモノメチルエーテルアセテート9.3g(和光純薬工業(株)製)を混合した溶液を、2時間かけて丸底フラスコに滴下した。その後、得られた溶液を90℃で2時間反応させた。反応後、室温まで冷却し、プロピレングリコールモノメチルエーテルアセテート16.2gを加えて希釈し、染料ポリマーを得た。これを染料ポリマーP-12(重量比:染料モノマーM-2/ベンジルメタクリレート=80/20)とする。このポリマー溶液の不揮発分濃度は、35.7%であった。
染料モノマーM-2の代わりに染料モノマーM-11を用いた以外は、実施例10と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-12(重量比:染料モノマーM-11/ベンジルメタクリレート=80/20)とする。このポリマー溶液の不揮発分濃度は、34.3%であった。
ベンジルメタクリレート50.1gを、ベンジルメタクリレート32.1gとコハク酸モノ(2-メタクリロイルオキシエチル)(新中村化学(株)製NKエステルSA)18gに変更した以外は、実施例7と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-14(染料モノマーM-2/ベンジルメタクリレート/コハク酸モノ(重量比:2-メタクリロイルオキシエチル)/メタクリル酸=5/53.5/30/11.5)とする。
ベンジルメタクリレート50.1gを、メチルメタクリレート32.1g、コハク酸モノ(2-メタクリロイルオキシエチル)18gに変更した以外は、実施例7と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-15(重量比:染料モノマーM-2/メチルメタクリレート/コハク酸モノ(2-メタクリロイルオキシエチル)/メタクリル酸=5/53.5/30/11.5)とする。
ベンジルメタクリレート50.1gを、メチルメタクリレート32.1g、ジエチルアクリルアミド(和光純薬工業(株)製)18gに変更した以外は、実施例7と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-16(重量比:染料モノマーM-2/メチルメタクリレート/ジエチルアクリルアミド/メタクリル酸=5/53.5/30/11.5)とする。
ベンジルメタクリレート50.1gを、メチルメタクリレート32.1g、スチレン(和光純薬工業(株)製)18gに変更した以外は、実施例7と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-17(重量比:染料モノマーM-2/メチルメタクリレート/スチレン/メタクリル酸=5/53.5/30/11.5)とする。
ベンジルメタクリレート50.1gを、メチルメタクリレート32.1g、N-フェニルマレイミド18gに変更した以外は、実施例7と同様の方法により、染料ポリマーを得た。これを染料ポリマーP-18(重量比:染料モノマーM-2/メチルメタクリレート/N-フェニルマレイミド/メタクリル酸=5/53.5/30/11.5)とする。
実施例5~8で得た染料ポリマーP-2~P-5、P-9及びP-11の耐熱性を下記のようにして評価した。
即ち、得られた染料ポリマーP-2~P-5、P-9及びP-11をそれぞれ3インチのガラスウエハー(コーニング社製イーグルXG)にスピンコートした後、90℃に加熱したホットプレート上で90秒間乾燥して膜厚1ミクロンの薄膜を得た。得られた薄膜それぞれを、分光光度計(島津製作所製分光光度計UV-2550)を用いて最大吸収波長での吸光度(λa)を測定し、その後、230℃に加熱したホットプレート上で30分間加熱した後、再度、吸光度(λb)を測定した。λaとλbの値から下記式より染料残存率(%)を求めた。また、得られた染料残存率について、下記の判定基準に従って評価した。
染料残存率(%)=(λb/λa)×100
◎:染料残存率≧81%
○:61%≦染料残存率<80%
△:51%≦染料残存率<60%
×:染料残存率≦50%
得られた結果を表1に示す。
染料ポリマーP-2~P-5、P-9及びP-11の代わりに染料ポリマーP-1、6又は7を用いた以外は、実施例21と同様の方法により、染料ポリマーP-1、6及び7の耐熱性評価を行った。
得られた結果を表1に示す。
実施例1~6で得た染料モノマーM-2~M-5、M-9及びM-11の耐熱性を下記のように評価した。
(1)染料を含まないポリマーの合成
攪拌装置、冷却管、温度計、窒素導入管を備えた500mlの丸底フラスコに、プロピレングリコールモノメチルエーテルアセテート98.5gを入れ、窒素気流下で内温が90℃になるまで加熱した。次いで、ベンジルメタクリレート 186.2g、メタクリル酸25.6g、ジメチル2,2´‐アゾビス(2-メチルプロピオネート)(和光純薬工業(株)製重合開始剤V‐601)33.9g、及びプロピレングリコールモノメチルエーテルアセテート98.5gを混合した溶液を、2時間かけて丸底フラスコに滴下した。その後、得られた溶液を90℃で2時間反応させた。反応後、室温まで冷却し、プロピレングリコールモノメチルエーテルアセテート171.5gを加えて希釈し、淡黄色透明のポリマー溶液を得た。これをポリマーAとする。尚、ポリマーAの不揮発分濃度は35.9%であった。
染料モノマー(M-2~M-4、M-9又はM-11)1g、ポリマーA52.9g、及びプロピレングリコールモノメチルエーテルアセテート3.2gを混合し、染料モノマー混合溶液Bを調製した。
染料ポリマーP-2~P-5の代わりに染料モノマー混合溶液Bを用いた以外は、実施例21と同様の方法により耐熱性を評価した。
染料モノマーM-2~M-5、M-9及びM-11の代わりに染料モノマーM-1、6又は7を用いた以外は、実施例21と同様の方法により、染料ポリマーP-1、6及び7の耐熱性評価を行った。
得られた結果を、実施例21、実施例22、及び比較例1と併せて表1に示す。
比較例2及び実施例22において、染料モノマーM-1、M-6及びM-7と染料モノマーM-2~M-4、M-9及びM-11とではそのアニオン成分が異なることから、アニオン成分として、テトラキス(ペンタフルオロフェニル)ホウ素(IV)アニオン、4-ニトロベンゼンスルホン酸アニオン、ペンタフルオロベンゼンスルホン酸アニオンを用いると耐熱性が向上すると考えられた。また、実施例21のP-5も優れた耐熱効果を示したことから、アニオン成分として4-フルオロベンゼンスルホン酸アニオンを用いても同様に耐熱性が向上すると考えられた。
また、実施例21の染料ポリマーは、実施例22の染料モノマーよりも染料残存率が高いことから、ポリマー化することにより更に耐熱性が向上することが分かった。
加熱時間30分を90分とし、染料ポリマーP-2~P-4、P-9、P-10、P-11、P-13~P-17を用いた以外は、実施例21と同様の方法により、これらのポリマー耐熱性評価を行った。得られた結果を表2に示す。
染料ポリマーP-2~P-4の代わりに染料ポリマーP-1、6又は7を用いた以外は、実施例21と同様の方法により、染料ポリマーP-1、6及び7の耐熱性評価を行った。得られた結果を表2に示す。
加熱時間30分を90分とした以外は実施例22と同様の方法により、染料モノマーM-2~4、M-9、M-10及びM-11の耐熱性評価を行った。
得られた結果を表2に示す。
加熱時間30分を90分とした以外は実施例22と同様の方法により、染料モノマーM-1、M-6及びM-7の耐熱性評価を行った。
得られた結果を、実施例23、実施例24及び比較例3と併せて表2に示す。
その結果、表2に示すように、加熱時間30分の場合と同様に、実施例23の染料ポリマーP-2~P-4、P-9及びP-11、並びに、実施例24の染料モノマーM-2~M-4、M-9及びM-11は、それらとアニオン成分が異なる染料ポリマーP-1、P-6、P-7、および、染料モノマーM-1、M-6、M-7と比較して、それぞれ高い耐熱性を示した。特に、テトラキス(ペンタフルオロフェニル)ホウ素(IV)アニオンをアニオン成分に用いたM-2、M-9及びM-11の染料モノマー、並びに、これらモノマーを含有するP-2、P-9、P-11、及びP-13~17の染料ポリマーが高い耐熱性を示すことが分かった。また、染料ポリマーは、染料モノマーと比較しても優れた耐熱性を有することが分かった。
一方、比較例3のP-1、P-6およびP-7、比較例4のM-1、M-6およびM-7は、30分の加熱の場合(比較例1および2)と比較して、染料残存率が大きく低下した。実施例23や24の染料ポリマー及び染料モノマーを用いた結果でも染料残存率の低下は見られるが、低下率に大きな差が見られた。
実施例14で得た染料ポリマーP-12を用い、簡易な紫外線硬化性のカラーレジストを作成し、硬化膜のプロピレングリコールモノメチルエーテルアセテートに対する耐溶剤性を評価した。
即ち、不揮発分の重量比で染料ポリマーP-12/ポリマーA/ジペンタエリスリトールヘキサアクリレート/2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1/3-メタクリルオキシプロピルトリメトキシシラン=18.8/36.2/30/10/5となるように混合し、レジスト液を得た。このレジスト液を、それぞれ3インチのガラスウエハーにスピンコートした後、100℃に加熱したホットプレート上で100秒間乾燥して膜厚1.5ミクロンの薄膜を得た。得られた薄膜のそれぞれに、高圧水銀灯を用いて200mJ/cm2の光量を照射し、0.5%KOH水溶液に90秒間浸漬したのち、イオン交換水で洗浄し、更に、230℃に加熱したホットプレート上で30分間加熱した。
分光光度計を用いて最大吸収波長での吸光度(λc)を測定し、その後、プロピレングリコールモノメチルエーテルの溶液に2時間浸漬した後、100℃に加熱したホットプレート上で100秒間加熱した後、再度、吸光度(λd)を測定した。λcとλdの値から下記式より染料残存率(%)を求めた。得られた染料残存率を耐溶剤性の指標とした。
染料残存率(%)=(λd/λc)×100
レジストの組成と耐溶剤性の結果を表3に示した。
染料ポリマーP-12の代わりに染料モノマーP-13を用いた以外は、実施例25と同様の方法により、染料ポリマーP-13の耐溶剤性の評価を行った。
得られた結果を、実施例25の結果と併せて表3に示した。
染料ポリマーP-12の代わりに染料モノマーM-2を用い、不揮発分の重量比で染料モノマーM-2/ポリマーA/ジペンタエリスリトールヘキサアクリレート/2―ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1/3-メタクリルオキシプロピルトリメトキシシラン=15/40/30/10/5となるように混合した以外は、実施例25と同様の方法により、染料モノマーM-2の耐溶剤性の評価を行った。レジストの組成と耐溶剤性の結果を、実施例25、26の結果と併せて表3に示した。
染料モノマーM-2の代わりに染料モノマーM-11を用いた以外は、実施例27と同様の方法により、染料モノマーM-11の耐溶剤性の評価を行った。レジストの組成と耐溶剤性の結果を、実施例25~27の結果と併せて表3に示した。
染料モノマーM-2の代わりに染料モノマーM-12を用いた以外は、実施例27と同様の方法により、染料モノマーM-12の耐溶剤性の評価を行った。レジストの組成と耐溶剤性の結果を、実施例25~28の結果と併せて表3に示した。
IRGACURE 369:2‐ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1((株)BASF社製)
LS-3380:3-メタクリルオキシプロピルトリメトキシシラン(信越化学工業(株)製)
PGMEA:プロピレングリコールモノメチルエーテルアセテート
NMP :N-メチル-2-ピロリドン
表3から明らかなように、P-12、P-13、M-2又はM-11を染料として用いた場合、溶媒への耐溶剤性が非常に高く、ほぼ90%以上の染料残存率であった。一方、比較例5で用いたM-12は、その耐溶剤性は43%と低かった。これは、アニオンが塩素イオンであり、重合性基を有さないローダミンBであるため、硬化膜中に固定化されていないことがその原因と考えられた。
表3の結果によれば、実施例25、26に使用した染料ポリマーP-12、P-13は、それぞれ、実施例27、28の染料モノマーM-2、M-11をポリマー化したものであるが、染料モノマーの形でレジストに添加するよりも、染料ポリマーの形で添加した方が、耐溶剤性が高いことが分かった。
不揮発分の重量比で染料モノマーM-2/ポリマーA/ジペンタエリスリトールヘキサアクリレート/2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1/3-メタクリルオキシプロピルトリメトキシシラン=15/25/45/10/5(実施例29)、15/10/60/10/5(実施例30)、又は15/0/70/10/5(実施例31)となるように混合して得たレジスト液を用いた以外は、実施例27と同様に実験し、耐溶剤性の評価を行った。レジストの組成と評価結果を表4に示す。
不揮発分の重量比で染料モノマーM-11/ポリマーA/ジペンタエリスリトールヘキサアクリレート/2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン-1/3-メタクリルオキシプロピルトリメトキシシラン=15/25/45/10/5(実施例32)、15/10/60/10/5(実施例33)、又は15/0/70/10/5(実施例34)となるように混合して得たレジスト液を用いた以外は、実施例28と同様に実験し、耐溶剤性の評価を行った。レジストの組成と評価結果を表4に示す。
また、ポリマー成分Aを全てDPHAとした実施例31及び34では、UV硬化後に膜が割れて基板から剥がれたため、耐溶剤性の測定をすることができなかった。これは、ポリマー成分Aを除去したことで紫外線照射後の膜は強い硬化収縮を生じ、基材への密着性が低下したためと考えられた。
(1)4-ヒドロキシブチルメタクリレートの合成
1,4-ブタンジオール135g(1.5モル、和光純薬工業(株)製)、1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド塩酸塩96g(0.5モル、東洋紡(株)製)、N,N-ジメチルアミノピリジン1.2g(和光純薬工業(株)製)を2Lのジクロロメタンに溶解した。次いで、メタクリル酸43g(0.5モル、和光純薬工業(株)製)を滴下して加え、室温で12時間攪拌した。その後、ロータリーエバポレーターを用いて溶媒を減圧留去し、ヘキサン/酢酸エチルを体積比で1/1に混合した溶液を展開溶媒としたシリカゲルカラムクロマトグラフィーにより精製し、無色オイル状の4-ヒドロキシブチルメタクリレート50g(収率63%)を得た。
攪拌装置を備えた2Lの丸底フラスコに、ローダミンB47.9g(0.10mol、和光純薬工業(株)製)、ジクロロメタン500ml、上記(1)で得た4-ヒドロキシブチルメタクリレート19.0g(0.12mol)、4‐ジメチルアミノピリジン4.9g(0.04mol、和光純薬工業(株)製)、1‐エチル‐3‐(3‐ジメチルアミノプロピル)カルボジイミド塩酸塩32.6g(0.17mol、東洋紡(株)製)を加え、室温で24時間攪拌して反応させた。反応終了後、有機層を約500mlのイオン交換水で洗浄した。次いで、硫酸ナトリウム50g加えて脱水し、重合禁止剤としてp‐メトキシフェノール10mg(和光純薬工業(株)製)を加えて減圧下で溶媒を留去し、赤色の固体52.6g(収率85.0%)を得た。
撹拌装置を備えた1Lの丸底フラスコに、上記(2)で得た赤色の固体37.2g(0.060mol)、テトラキス(ペンタフルオロフェニル)ホウ素(IV)のリチウム塩 41.1g(0.060mol、東ソー・ファインケム(株)製)、ジクロロメタン450ml、イオン交換水450mlを加えた後、室温で30分間攪拌することにより、塩交換反応を行った。反応終了後、有機層を約450mlのイオン交換水で4回洗浄した。次いで、p‐メトキシフェノール15mg(和光純薬工業(株)製)を加え、減圧下で濃縮し、染料モノマーM‐1の塩化物イオンがテトラキス(ペンタフルオロフェニル)ホウ素(IV)アニオンに交換された赤色の固体70.5g(収率93.0%)を得た。これを染料モノマーM-21とする。
(1)6-ヒドロキシヘキシルメタクリレートの合成
1,6-ヘキサンジオール177g(1.5モル、和光純薬工業(株)製)、1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド塩酸塩96g(0.5モル、東洋紡(株)製)、N,N-ジメチルアミノピリジン12g(和光純薬工業(株)製)を2Lのジクロロメタンに溶解し、メタクリル酸43g(0.5モル、和光純薬工業(株)製)を滴下して加え、室温で12時間攪拌した。ロータリーエバポレーターを用いて溶媒を減圧留去し、ヘキサン/酢酸エチルを体積比で1/1に混合した溶液を展開溶媒としたシリカゲルカラムクロマトグラフィーにより精製し、無色オイル状の6-ヒドロキシヘキシルメタクリレート56g(収率60%)を得た。
4-ヒドロキシブチルメタクリレート19.0g(0.12mol)の代わりに6-ヒドロキシヘキシルメタクリレート22.4g(0.12mol)を用いた以外は、実施例35の(2)及び(3)の方法に準じてモノマーを合成した。得られたモノマーを染料モノマーM-22とする。
(1)8-ヒドロキシオクチルメタクリレートの合成
1,8-オクタンジオール219g(1.5モル、和光純薬工業(株)製)、1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド塩酸塩96g(0.5モル、東洋紡(株)製)、N,N-ジメチルアミノピリジン12g(和光純薬工業(株)製)を2Lのジクロロメタンに溶解し、メタクリル酸43g(0.5モル、和光純薬工業(株)製)を滴下して加え、室温で12時間攪拌した。ロータリーエバポレーターを用いて溶媒を減圧留去し、ヘキサン/酢酸エチルを3/2の体積比で混合した溶液を展開溶媒としたシリカゲルカラムクロマトグラフィーにより精製し、無色オイル状の8-ヒドロキシオクチルメタクリレート72g(収率68%)を得た。
4-ヒドロキシブチルメタクリレート19.0g(0.12mol)の代わりに8-ヒドロキシオクチルメタクリレート25.7g(0.12mol)を用いた以外は、実施例35の(2)及び(3)の方法に準じてモノマーを合成した。得られたモノマーを染料モノマーM-23とする。
(1)10-ヒドロキシデシルメタクリレートの合成
1,10-デカンジオール87g(0.5モル、和光純薬工業(株)製)、メタクリル酸43g(0.5モル、和光純薬工業(株)製)、p-トルエンスルホン酸5.1g(和光純薬工業(株)製)、p-メトキシフェノール0.6g(和光純薬工業(株)製)およびヘキサン150mlを混合し、15時間還流脱水した。得られた反応液に、83%のメタノール水溶液500mlを加えて十分に攪拌したのち、メタノール水溶液層をヘキサンで3回洗浄し、副生性物である1,12-ドデカンジオールジメタクリレートを除去した。次いで、メタノール水溶液層からメタノールを減圧留去したのち、ヘキサンにて12-ヒドロキシドデシルメタクリレートを抽出した。その後、溶媒を留去して10-ヒドロキシデシルメタクリレート63g(収率52%)を得た。
4-ヒドロキシブチルメタクリレート19.0g(0.12mol)の代わりに10-ヒドロキシデシルメタクリレート29.1g(0.12mol)を用いた以外は、実施例35の(2)及び(3)の方法に準じてモノマーを合成した。得られたモノマーを染料モノマーM-24
とする。
(1)12-ヒドロキシドデシルメタクリレートの合成
1,12-ドデカンジオール101g(0.5モル、和光純薬工業(株)製)、メタクリル酸43g(0.5モル、和光純薬工業(株)製)、p-トルエンスルホン酸5.1g(和光純薬工業(株)製)、p-メトキシフェノール0.6g(和光純薬工業(株)製)およびヘキサン150mlを混合し、15時間還流脱水した。得られた反応液に、83%のメタノール水溶液500mlを加えて十分に攪拌したのち、メタノール水溶液層をヘキサンで3回洗浄し、副生性物である1,12-ドデカンジオールジメタクリレートを除去した。次いで、メタノール水溶液層からメタノールを減圧留去したのち、ヘキサンにて12-ヒドロキシドデシルメタクリレートを抽出した。その後、溶媒を留去して12-ヒドロキシドデシルメタクリレート43g(収率32%)を得た。
4-ヒドロキシブチルメタクリレート19.0g(0.12mol)の代わりに12-ヒドロキシドデシルメタクリレート32.4g(0.12mol)を用いた以外は、実施例35の(2)及び(3)の方法に準じてモノマーを合成した。得られたモノマーを染料モノマーM-25とする。
攪拌装置、冷却管、温度計、窒素導入管を備えた200mlの丸底フラスコに、プロピレングリコールモノメチルエーテルアセテート27.9g(和光純薬工業(株)製)を入れ、窒素気流下で内温が90℃になるまで加熱した。次いで、染料モノマーM-2 48.0g、メチルメタクリレート5.0g(和光純薬工業(株)製)、メタクリル酸7.0g(和光純薬工業(株)製)、ジメチル2,2´‐アゾビス(2-メチルプロピオネート)(和光純薬工業(株)製重合開始剤V‐601)9.6g、及びプロピレングリコールモノメチルエーテルアセテート27.9g(和光純薬工業(株)製)を混合した溶液を、2時間かけて丸底フラスコに滴下した。その後、得られた溶液を90℃で2時間反応させた。反応後、室温まで冷却し、プロピレングリコールモノメチルエーテルアセテート48.6gを加えて希釈し、染料ポリマーを得た。これを染料ポリマーP-20(重量比:染料モノマーM-2/メチルメタクリレート/メタクリル酸=80/8.3/11.7)とする。また、得られたポリマー溶液のゲルパーミエーションクロマトグラフィー分析の結果、含有する未反応の染料モノマーの割合重量量は、総重量の19.8%であった。
染料モノマーM-2 48.0gの代わりに染料モノマーM-21~M25 48.0gを用いた以外は、それぞれ実施例40と同様に実験し、5種類の染料ポリマーを得た。これらをそれぞれ染料ポリマーP-21、P-22、P-23、P-24、P-25とする。また、得られたP-21~P-25のポリマー溶液のゲルパーミエーションクロマトグラフィー分析の結果、含有する未反応の染料モノマー量は、面積%でそれぞれ、15.2%、4.9%、3.2%、0.9%、5.3%であった。その結果を実施例40の結果と合わせて表5に示す。
染料ポリマーとしてP-21~P-25を用いた以外は、実施例21と同様の方法により、染料ポリマーP-21~P-25の耐熱性評価を行った。その結果を実施例40~45の未反応モノマー量と併せて表5に示す。
また、耐熱性評価の結果、染料モノマー中の二重結合とベンゼン環の間の原子の数が6~14の場合には優れた耐熱性効果を示したが、16の場合には耐熱性が低下した。この原因は定かではないが、鎖長が長くなり、ポリマーの動きの自由度が増大することにより、染料の骨格自体の分解が促進されたためと考えられた。
Claims (20)
- (i)電子吸引性の置換基を有するアリール基及びアニオン基を含むアニオンをカウンターアニオンとして有するカチオン性ローダミン誘導体と(ii)エチレン性不飽和結合とを有する化合物由来のモノマー単位を有するポリマー。
- 電子吸引性の置換基が、炭素数1~3のハロゲン化アルキル基、ハロゲン原子又は/およびニトロ基である、請求項1記載のポリマー。
- 電子吸引性の置換基がハロゲン原子である、請求項1記載のポリマー。
- 電子吸引性の置換基がフッ素原子である、請求項1記載のポリマー。
- アリール基がフェニル基である、請求項1記載のポリマー。
- アニオン基が、4級ホウ素アニオン基又はスルホン酸アニオン基である、請求項1記載のポリマー。
- モノマー単位が、下記一般式(I)で示される化合物由来のモノマー単位を有するものである、請求項1記載のポリマー
(式中、R1~R4はそれぞれ独立して、水素原子、炭素数1~30のアルキル基、炭素数1~6のヒドロキシアルキル基、炭素数1~6のスルホアルキル基、炭素数2~7のカルボキシアルキル基、炭素数2~7のシアノアルキル基、炭素数2~6のアルコキシアルキル基、炭素数1~6のハロゲノアルキル基、置換基を有する又は無置換のフェニル基またはベンジル基を表し、R5~R7はそれぞれ独立して水素原子またはメチル基を表し、A1は、-O-、-OCO-、-COO-又はアリーレン基の少なくとも1つの基を鎖中に有し、且つ、ヒドロキシル基を置換基として有する炭素数1~21のアルキレン基、-O-、-OCO-、-COO-又はアリーレン基の少なくとも1つの基を鎖中に有する炭素数1~21のアルキレン基、炭素数1~9のアルキレン基、或いは、水酸基を置換基として有する炭素数1~6のアルキレン基を表し、A2は-NH-または-O-を表す。An-は、電子吸引性の置換基を有するアリール基含むアニオンを表す)。 - ポリマーがコポリマーである、請求項8記載のポリマー。
- コポリマーが、下記一般式(II)、一般式(III)、一般式(IV)又は一般式(V)で示される化合物由来のモノマー単位1~2種と上記一般式(I)で示される化合物由来のモノマー単位とを構成成分とするものである、請求項8記載のポリマー
[式中、R11は、水素原子又はメチル基を表し、R12は、水素原子、炭素数1~18のアルキル基、炭素数1~10のヒドロキシルアルキル基、炭素数6~10のアリール基、炭素数7~13のアリールアルキル基、炭素数2~9のアルコキシアルキル基、炭素数3~9のアルコキシアルコキシアルキル基、炭素数7~13のアリールオキシアルキル基、炭素数5~7のモルホリノアルキル基、炭素数3~9のトリアルキルシリル基、酸素を有する又は酸素を有さない炭素数6~10の脂環式炭化水素基、炭素数3~9のジアルキルアミノアルキル基、炭素数1~18のフッ化アルキル基、又は炭素数1~6のN-アルキレンフタルイミド基、下記一般式(II-I)で示される基
(式中、R15は、炭素数1~3のアルキレン基を表し、R16は、ヒドロキシル基を置換基として有する又は無置換のフェニル基、或いは炭素数1~3のアルキル基を表し、qは1~3の整数を表す。)、
下記一般式(II-II)で示される基
(式中、R17~R19は炭素数1~3のアルキル基を表し、R20は炭素数1~3のアルキレン基を表す。)、下記一般式(II-III)で示される基
(式中、lは、1~6の整数を表し、R21はフェニレン基又はシクロへキシレン基を表す)を表す。]、
(式中、R11は上記と同じ。R13は、水素原子又は炭素数1~3のアルキル基を表し、R14は、水素原子、炭素数1~3のアルキル基、炭素数3~7のジアルキルアミノアルキル基、又は炭素数1~6のヒドロキシアルキル基を表す。R13とR14は、これらと隣接する窒素原子とでモルホリノ基を形成してもよい。)、
(式中、R31は、フェニル基、ピロリジノ基を表し、R11は上記と同じ。)
(式中、R33は、窒素原子又は酸素原子を表し、jは、R33が酸素原子の場合に0を表し、R33が窒素原子の場合には1を表す。R32は、水素原子、炭素数1~20のアルキル基、炭素数1~10のヒドロキシルアルキル基、炭素数1~10のハロゲン化アルキル基、炭素数1~10のアルキルシクロアルキル基、炭素数6~7のハロゲン化シクロアルキル基、炭素数6~10のアリール基、炭素数1~6のアルキル基を置換基として有する炭素数6~10のアリール基、又は、炭素数6~10のハロゲン化アリール基を表す。)。 - (i)電子吸引性の置換基を有するアリール基及びアニオン基を含むアニオンをカウンターアニオンとして有するカチオン性ローダミン誘導体と(ii)エチレン性不飽和結合とを有する化合物。
- 電子吸引性の置換基が、炭素数1~3のハロゲン化アルキル基、ハロゲン原子又は/およびニトロ基である、請求項11記載の化合物。
- 電子吸引性の置換基がハロゲン原子である、請求項11記載の化合物。
- 電子吸引性の置換基がフッ素原子である、請求項11記載の化合物。
- アリール基がフェニル基である、請求項11記載の化合物。
- アニオン基が、4級ホウ素アニオン基又はスルホン酸アニオン基である、請求項11記載の化合物。
- 化合物が、下記一般式(I)で示される化合物である、請求項11記載の化合物
(式中、R1~R4はそれぞれ独立して、水素原子、炭素数1~30のアルキル基、炭素数1~6のヒドロキシアルキル基、炭素数1~6のスルホアルキル基、炭素数2~7のカルボキシアルキル基、炭素数2~7のシアノアルキル基、炭素数2~6のアルコキシアルキル基、炭素数1~6のハロゲノアルキル基、置換基を有する又は無置換のフェニル基またはベンジル基を表し、R5~R7はそれぞれ独立して水素原子またはメチル基を表し、A1は、-O-、-OCO-、-COO-又はアリーレン基の少なくとも1つの基を鎖中に有し、且つ、ヒドロキシル基を置換基として有する炭素数1~21のアルキレン基、-O-、-OCO-、-COO-又はアリーレン基の少なくとも1つの基を鎖中に有する炭素数1~21のアルキレン基、炭素数1~9のアルキレン基、或いは、水酸基を置換基として有する炭素数1~6のアルキレン基を表し、A2は-NH-または-O-を表す。An-は、電子吸引性の置換基を有するアリール基及びアニオン基を含むアニオンを表す)。 - 請求項1記載のポリマー又は請求項11記載の化合物を含んでなる着色組成物。
- 請求項1記載のポリマー又は請求項11記載の化合物を含んでなるカラーフィルター用着色組成物。
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CN105073801B (zh) | 2017-03-08 |
EP2957578A1 (en) | 2015-12-23 |
CN105073801A (zh) | 2015-11-18 |
KR102148640B1 (ko) | 2020-08-28 |
EP2957578B1 (en) | 2017-03-22 |
US10450462B2 (en) | 2019-10-22 |
TWI615433B (zh) | 2018-02-21 |
KR20150119279A (ko) | 2015-10-23 |
EP2957578A4 (en) | 2015-12-23 |
US20160040013A1 (en) | 2016-02-11 |
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TW201443135A (zh) | 2014-11-16 |
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