CN108239429A - Compound, colored resin composition, colour filter, display device and solid-state imager - Google Patents
Compound, colored resin composition, colour filter, display device and solid-state imager Download PDFInfo
- Publication number
- CN108239429A CN108239429A CN201711382469.6A CN201711382469A CN108239429A CN 108239429 A CN108239429 A CN 108239429A CN 201711382469 A CN201711382469 A CN 201711382469A CN 108239429 A CN108239429 A CN 108239429A
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- resin composition
- compound
- aromatic
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 239000011342 resin composition Substances 0.000 title claims abstract description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 67
- 229910052799 carbon Inorganic materials 0.000 claims description 67
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 239000011347 resin Substances 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 20
- 239000003505 polymerization initiator Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000003086 colorant Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 52
- -1 o- tolyl Chemical group 0.000 description 43
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 40
- 239000002904 solvent Substances 0.000 description 35
- 239000002585 base Substances 0.000 description 28
- 238000004519 manufacturing process Methods 0.000 description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 239000000049 pigment Substances 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000012752 auxiliary agent Substances 0.000 description 9
- 125000001246 bromo group Chemical group Br* 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000004040 coloring Methods 0.000 description 7
- 239000000470 constituent Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 4
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 150000004816 dichlorobenzenes Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 150000004767 nitrides Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 2
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical compound BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical compound FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241001062009 Indigofera Species 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 2
- 150000005204 hydroxybenzenes Chemical class 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 description 2
- 239000000983 mordant dye Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002921 oxetanes Chemical group 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- 238000001259 photo etching Methods 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000992 solvent dye Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- QRFALSDGOMLVIR-UHFFFAOYSA-N 1,2,3,4-tetrabromobenzene Chemical compound BrC1=CC=C(Br)C(Br)=C1Br QRFALSDGOMLVIR-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical class CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical class O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- ZEWLHMQYEZXSBH-UHFFFAOYSA-N 4-[2-(2-methylprop-2-enoyloxy)ethoxy]-4-oxobutanoic acid Chemical compound CC(=C)C(=O)OCCOC(=O)CCC(O)=O ZEWLHMQYEZXSBH-UHFFFAOYSA-N 0.000 description 1
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- RNQBLUNNAYFBIW-NPULLEENSA-M hexadecyl(trimethyl)azanium (2S)-2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound COc1ccc2cc(ccc2c1)[C@H](C)C([O-])=O.CCCCCCCCCCCCCCCC[N+](C)(C)C RNQBLUNNAYFBIW-NPULLEENSA-M 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 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
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
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- 238000004904 shortening Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 229910021509 tin(II) hydroxide Inorganic materials 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
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- 229920002554 vinyl polymer Polymers 0.000 description 1
- YEIGUXGHHKAURB-UHFFFAOYSA-N viridine Natural products O=C1C2=C3CCC(=O)C3=CC=C2C2(C)C(O)C(OC)C(=O)C3=COC1=C23 YEIGUXGHHKAURB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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Abstract
The present invention relates to compound, colored resin composition, colour filter, display device and solid-state imagers.The contrast of colour filter formed by the colored resin composition of the present invention can fully be met.
Description
Technical field
The present invention relates to compound, colored resin composition, colour filter, display device and solid-state imagers.
Background technology
It is passed in the display devices such as liquid crystal display device, el display device and plasma scope, CCD, CMOS
Colour filter used in the solid-state imagers such as sensor is manufactured by colored resin composition.It is combined as such pigmentary resin
Object, it is known that include the composition (patent document 1) part brominated phthalocyanine zinc pigment as colorant.
Existing technical literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 2004-70342 bulletins
Invention content
The subject that the invention solves
The colour filter formed by previously known above-mentioned colored resin composition cannot fully meet contrast sometimes.
Means for solving the problems
The present invention includes following invention.
[1] colored resin composition, which contain toner and resin, above-mentioned colorant includes the chemical combination represented by formula (Ia)
Object.
[in formula (Ia), R1~R4Each independently represent can have substituent group carbon number 6~20 aromatic hydrocarbyl or
There can be the aromatic heterocycle of the carbon number 3~19 of substituent group.
R5~R12Each independently represent hydrogen atom, halogen atom, cyano, nitro, the carbon number 1~20 that there can be substituent group
Saturated hydrocarbyl, can be with the carbon number 6~20 of substituent group aromatic hydrocarbyl or can the virtue with the carbon number 3~19 of substituent group
Fragrant race's heterocycle.R5With R6、R7With R8、R9With R10And R11With R12It can respectively be combined with each other and form the virtue that can have substituent group
Fragrant race's hydrocarbon ring.
M represents the metallic atom of divalent or the trivalent with substituent group or the metallic atom of 4 valencys.]
[2] colored resin composition described in above-mentioned [1] also includes polymerizable compound and polymerization initiator.
[3] colour filter formed as the colored resin composition described in above-mentioned [1] or [2].
[4] display device, it includes the colour filters described in above-mentioned [3].
[5] solid-state imager, it includes the colour filters described in above-mentioned [3].
[6] compound represented by formula (Ib ').
[in formula (Ib '), ring A1~A4The aromatic series hydrocarbon ring of substituent group can be had by each independently representing.But, ring A1~
A4In it is at least one be the aromatic series hydrocarbon ring with substituent group.
R1~R4Each independently represent can be with the carbon number 6~20 of substituent group aromatic hydrocarbyl or can with substitution
The aromatic heterocycle of the carbon number 3~19 of base.
M represents the metallic atom of divalent or the trivalent with substituent group or the metallic atom of 4 valencys.]
The effect of invention
Colored resin composition using the present invention can manufacture the high colour filter of contrast.
Specific embodiment
The colored resin composition of the present invention includes colorant and resin.Colorant is known as " colorant sometimes below
(A) ", resin is known as " resin (B) " sometimes.
＜ colorants (A) ＞
Above-mentioned colorant (A) includes the compound represented by formula (Ia).Below sometimes by the compound represented by formula (Ia)
Referred to as " compound (Ia) ".
[in formula (Ia), R1~R4Each independently represent can have substituent group carbon number 6~20 aromatic hydrocarbyl or
There can be the aromatic heterocycle of the carbon number 3~19 of substituent group.
R5~R12Each independently represent hydrogen atom, halogen atom, cyano, nitro, the carbon number 1~20 that there can be substituent group
Saturated hydrocarbyl, can be with the carbon number 6~20 of substituent group aromatic hydrocarbyl or can the virtue with the carbon number 3~19 of substituent group
Fragrant race's heterocycle.R5With R6、R7With R8、R9With R10And R11With R12It can respectively be combined with each other and form the virtue that can have substituent group
Fragrant race's hydrocarbon ring.
M represents the metallic atom of divalent or the trivalent with substituent group or the metallic atom of 4 valencys.]
By R1~R4And R5~R12The carbon number of the aromatic hydrocarbyl of expression is preferably 6~15, and more preferably 6~12.As this
Aromatic hydrocarbyl, can enumerate phenyl, o- tolyl, m- tolyl, p- tolyl, xylyl, 4- n-butyls phenyl,
4- tert-butyls phenyl, naphthalene, anthryl, phenanthryl, xenyl, terphenyl etc., preferably phenyl, o- tolyl, m- toluene
Base, p- tolyl, 4- n-butyls phenyl, particularly preferably 4- tert-butyl phenyl, 4- n-butyls phenyl, phenyl.
By R1~R4And R5~R12The above-mentioned aromatic hydrocarbyl represented can have the substituent group of 1 or 2 or more.It is taken as this
Dai Ji can enumerate the halogen atoms such as fluorine atom, chlorine atom, iodine atom, bromine atoms；The carbon numbers such as chloromethyl, trifluoromethyl 1~6
Halogenated alkyl；The alkoxy of the carbon numbers such as methoxyl group, ethyoxyl 1~6；Hydroxyl；The alkane sulphonyl of the carbon numbers such as mesyl 1~6
Base；Alkoxy carbonyl of the carbon numbers such as methoxycarbonyl, ethoxy carbonyl 1~6 etc..As the aromatic hydrocarbyl with substituent group,
Such as 2- fluorophenyls, 2- chlorphenyls, 2- bromophenyls, 2- iodophenyls, 3- fluorophenyls, 3- chlorphenyls, 3- bromophenyls, 3- can be enumerated
Iodophenyl, 4- fluorophenyls, 4- chlorphenyls, 4- bromophenyls, 4- iodophenyls, 2,3- dichlorophenyls, 2,4 dichloro benzene base, 2,5- dichloros
Phenyl, 2,6- dichlorophenyls, 3,5- dichlorophenyls, 2,6- difluorophenyls, 1,3,5- trichlorophenyls, 2,3,4,5- tetrachloros phenyl,
4- chloromethyl phenyls, 2- trifluoromethyls, 2- methoxyphenyls, 3- methoxyphenyls, 4- methoxyphenyls, 2- hydroxy phenyls, 3-
Hydroxy phenyl, 4- hydroxy phenyls, 4- aminosulfonylphenyls, 2- methanesulfonylphenYls etc., preferably 2- methoxyphenyls, 3- methoxies
Base phenyl, 4- methoxyphenyls.
By R1~R4And R5~R12The carbon number of the aromatic heterocycle of expression is preferably 3~12, and more preferably 3~8.As
The aromatic heterocycle, can enumerate thienyl, methylthiophene base, furyl, pyrrole radicals, imidazole radicals, pyrazolyl, thiazolyl,
Isothiazolyl, pyridyl group, indyl, isoindolyl, indazolyl etc..
By R1~R4And R5~R12The above-mentioned aromatic heterocycle represented can have the substituent group of 1 or 2 or more.As this
Substituent group can enumerate the halogen atoms such as fluorine atom, chlorine atom, iodine atom, bromine atoms；The carbon numbers such as chloromethyl, trifluoromethyl 1~
6 halogenated alkyl；The alkoxy of the carbon numbers such as methoxyl group, ethyoxyl 1~6；Hydroxyl；The alkane sulphonyl of the carbon numbers such as mesyl 1~6
Base；Alkoxy carbonyl of the carbon numbers such as methoxycarbonyl, ethoxy carbonyl 1~6 etc..As the heteroaromatic with substituent group
Base can enumerate thienyl, furyl, pyrrole radicals, thiazolyl, oxazolyls etc..
By R5~R12The saturated hydrocarbyl of expression can be straight-chain, branch's chain state and cricoid any.As straight-chain
Or the saturated hydrocarbyl of branch's chain state, methyl, ethyl, n-propyl, normal-butyl, n-pentyl, n-hexyl, n-heptyl, just can be enumerated
The straight-chain alkyls such as octyl group, n-nonyl, positive decyl, dodecyl, n-hexadecyl, n-eicosane base；Isopropyl, isobutyl
Base, isopentyl, neopentyl, 2- ethylhexyls etc. divide branched-chain alkyl etc.；Cycloalkyl such as cyclohexyl etc..The carbon number of the saturated hydrocarbyl
Preferably 1~10, more preferably 1~8, further preferably 1~6.
By R5~R12The above-mentioned saturated hydrocarbyl represented can have the substituent group of 1 or 2 or more.As the substituent, it can arrange
Enumerate the halogen atoms such as fluorine atom, chlorine atom, iodine atom, bromine atoms；The alkoxy of the carbon numbers such as methoxyl group, ethyoxyl 1~6；Hydroxyl
Base；Cyano；The acyl groups such as acetyl group；The alkane sulfonyl of the carbon numbers such as mesyl 1~6；The carbon such as methoxycarbonyl, ethoxy carbonyl
Alkoxy carbonyl of number 1~6 etc..As the saturated hydrocarbyl with substituent group, chloromethyl, trifluoromethyl, hydroxyl second can be enumerated
Base, ethoxyethyl group, cyanopropyl, acetyl group propyl etc..
As by R5~R12The halogen atom of expression can enumerate fluorine atom, chlorine atom, bromine atoms, iodine atom etc., preferably
For bromine atoms.
R5With R6、R7With R8、R9With R10Or R11With R12It can respectively be combined with each other and form aromatic series hydrocarbon ring.As the virtue
Fragrant race's hydrocarbon ring, can enumerate benzene.The structure that the aromatic series hydrocarbon ring of carbon number 6~20 forms further is condensed or combined on the benzene
Included in the aromatic series hydrocarbon ring.As the structure for condensing on benzene or forming with reference to aromatic series hydrocarbon ring, can enumerate naphthalene, anthracene,
Phenanthrene, biphenyl, terphenyl etc..In addition, the structure that the saturated hydrocarbyl of carbon number 1~20 is combined in aromatic series hydrocarbon ring is also contained in virtue
In fragrant race's hydrocarbon ring.As aromatic series hydrocarbon ring, preferably benzene.
R5With R6、R7With R8、R9With R10Or R11With R12The aromatic series hydrocarbon ring of formation can have the substitution of 1 or 2 or more
Base.As the substituent, the halogen atoms such as fluorine atom, chlorine atom, iodine atom, bromine atoms can be enumerated；Chloromethyl, trifluoromethyl
Wait the halogenated alkyl of carbon numbers 1~6；The alkoxy of the carbon numbers such as methoxyl group, ethyoxyl 1~6；Hydroxyl；The carbon numbers such as mesyl 1~6
Alkane sulfonyl；The acyl group of the carbon numbers such as acetyl group 2~6；Hydroxycarbonyl group；The carbon numbers such as methoxycarbonyl, ethoxy carbonyl 1~6
Alkoxy carbonyl etc..As the aromatic series hydrocarbon ring with substituent group, such as phenyl-monofluoride, difluorobenzene, trifluoro-benzene, four can be enumerated
Fluorobenzene, monochloro-benzene, dichloro-benzenes, trichloro-benzenes, tetrachlorobenzene, phenyl-monobromide, dibromobenzene, tribromo-benzene, tetrabromo-benzene, methoxybenzene, ethyoxyl
Benzene, hydroxy benzenes, mesyl benzene, acetylbenzene, hydroxycarbonyl group benzene, methoxycarbonyl benzene, ethoxy carbonyl benzene etc., preferably second
Acyl group benzene, hydroxycarbonyl group benzene, ethoxy carbonyl benzene, phenyl-monofluoride, monochloro-benzene, phenyl-monobromide, difluorobenzene, dichloro-benzenes, dibromobenzene, especially
Preferably monochloro-benzene.
As the metallic atom of the valency of the divalent represented by above-mentioned M~4, the long week according to IUPAC1990 rules can be enumerated
The metallic atom of race of the 2nd race~the 15th is classified as in phase type periodic table.In these, as metallic element, preferably Mg, Ti, Zr, V,
Nb、Ta、Cr、Mo、W、Mn、Fe、Co、Ni、Ru、Rh、Pd、Os、Ir、Pt、Cu、Ag、Au、Zn、Cd、Hg、Al、Ga、In、Si、Ge、
Sn, Pb, Sb, Bi etc., more preferable Ti, Zr, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Hg, Al, Ga, Si, Ge, Sn etc., it is further excellent
Select Ni, Zn, Hg, most preferably Zn.
The metallic atom of trivalent or 4 valencys has substituent group in above-mentioned metallic atom.It is preferred that trivalent or 4 valencys with substituent group
Metallic atom with 2 nitrogen-atoms by forming 2 N-M keys, thereby using 2 valences, with remaining valence and substituent group
With reference to.The substituent group that metallic atom as trivalent or 4 valencys has can enumerate the halogen atoms such as chlorine atom；Oxo base；Hydroxyl；
The acyloxy such as acetoxyl group；Alkane sulfonyloxies such as mesyloxy etc..
As the trivalent with halogen atom or the metallic atom of 4 valencys, AlCl, SiCl can be enumerated2、VCl、VCl2、VOCl、
FeCl, GaCl, ZrCl etc..
As the trivalent with oxo base or the metallic atom of 4 valencys, VO, GeO etc. can be enumerated.
As the trivalent with hydroxyl or the metallic atom of 4 valencys, Si (OH) can be enumerated2、Cr(OH)2、Sn(OH)2Deng.
Compound (Ia) preferred R5~R12It is at least one for the aromatic hydrocarbyl of carbon number 6~20 or the virtue of carbon number 3~19
Fragrant race's heterocycle or R5With R6、R7With R8、R9With R10Or R11With R12It is combined with each other and forms aromatic series hydrocarbon ring, further
The compound preferably represented by formula (Ib).To " compound (Ib) " be known as by the compound that formula (Ib) represents sometimes below.
[in formula (Ib), ring A1~A4The aromatic series hydrocarbon ring of substituent group can be had by each independently representing.R1~R4With M with it is upper
It states identical.]
Further more, by A1~A4At least one of the aromatic series hydrocarbon ring of expression can be the aromatic series hydrocarbon ring with substituent group.
It, sometimes will be by A in compound (Ib)1~A4At least one of the aromatic series hydrocarbon ring of expression is the aromatic series hydrocarbon ring with substituent group
Compound be known as " compound (Ib ') ".
As by A1~A4The aromatic series hydrocarbon ring of expression, can enumerate benzene.Carbon number is further condensed or combined on the benzene
The structure of 6~20 aromatic series hydrocarbon ring is also contained in above-mentioned aromatic series hydrocarbon ring.It condenses as on benzene or combines aromatic series
The structure of hydrocarbon ring can enumerate naphthalene, anthracene, phenanthrene, biphenyl, terphenyl etc..In addition, carbon number 1~20 is combined in aromatic series hydrocarbon ring
The structure of saturated hydrocarbyl be also contained in aromatic series hydrocarbon ring.As aromatic series hydrocarbon ring, preferably benzene.
By A1~A4The above-mentioned aromatic series hydrocarbon ring represented can have the substituent group of 1 or 2 or more.As the substituent, it can arrange
Enumerate the saturated hydrocarbyl of carbon number 1~20；The aromatic hydrocarbyl of carbon number 6~20；The halogen such as fluorine atom, chlorine atom, iodine atom, bromine atoms
Plain atom；The halogenated alkyl of the carbon numbers such as chloromethyl, trifluoromethyl 1~6；The alkoxy of the carbon numbers such as methoxyl group, ethyoxyl 1~6；Hydroxyl
Base；The alkane sulfonyl of the carbon numbers such as mesyl 1~6；The acyl group of the carbon numbers such as acetyl group 2~6；Hydroxycarbonyl group；Methoxycarbonyl,
Alkoxy carbonyl of the carbon numbers such as ethoxy carbonyl 1~6 etc..As the aromatic series hydrocarbon ring with substituent group, such as one can be enumerated
Fluorobenzene, difluorobenzene, trifluoro-benzene, phenyl tetrafluoride, monochloro-benzene, dichloro-benzenes, trichloro-benzenes, tetrachlorobenzene, phenyl-monobromide, dibromobenzene, tribromo-benzene, four
Bromobenzene, methoxybenzene, ethoxybenzene, hydroxy benzenes, mesyl benzene, acetylbenzene, hydroxycarbonyl group benzene, methoxycarbonyl benzene, second
Epoxide carbonyl benzene etc., preferably acetylbenzene, hydroxycarbonyl group benzene, ethoxy carbonyl benzene, phenyl-monofluoride, monochloro-benzene, phenyl-monobromide, difluoro
Benzene, dichloro-benzenes, dibromobenzene, particularly preferably monochloro-benzene.
As compound (Ib), the compound preferably represented by formula (Ic).Below sometimes by the chemical combination represented by formula (Ic)
Object is known as " compound (Ic) ".
[in formula (Ic), R21~R36Each independently represent the saturated hydrocarbons of hydrogen atom, the carbon number 1~20 that there can be substituent group
Base, the aromatic hydrocarbyl of carbon number 6~20 that can have substituent group, halogen atom, the halogenated alkyl of carbon number 1~6, carbon number 1~6
Alkoxy, hydroxyl, the alkane sulfonyl of carbon number 1~6, the acyl group of carbon number 2~6, hydroxycarbonyl group or carbon number 1~6 alkoxy carbonyl
Base.
R1~R4It is same as described above with M.]
Further more, R21~R36At least one of can be can have substituent group carbon number 1~20 saturated hydrocarbyl, can have
The aromatic hydrocarbyl of the carbon number 6~20 of substituted base, halogen atom, the halogenated alkyl of carbon number 1~6, carbon number 1~6 alkoxy,
Hydroxyl, the alkane sulfonyl of carbon number 1~6, the acyl group of carbon number 2~6, hydroxycarbonyl group or carbon number 1~6 alkoxy carbonyl.
By R21~R36The saturated hydrocarbyl with substituent group that represents and by R5~R12What is represented has the full of substituent group
It is identical with alkyl.
By R21~R36The aromatic hydrocarbyl with substituent group that represents and by R1~R4And R5~R12What is represented has
The aromatic hydrocarbyl of substituent group is identical.
As by R21~R36The halogen atom of expression can enumerate fluorine atom, chlorine atom, iodine atom, bromine atoms etc., make
For halogenated alkyl, chloromethyl, trifluoromethyl etc. can be enumerated, as alkoxy, methoxyl group, ethyoxyl etc. can be enumerated, as
Alkane sulfonyl can enumerate mesyl etc., as alkoxy carbonyl, can enumerate methoxycarbonyl, ethoxy carbonyl etc..
As compound (Ic), preferably by R21~R36In the group of expression 1~8 for chlorine atom or bromine atoms, remaining as
The compound of hydrogen atom and by R21~R36The group of expression is all the compound of hydrogen atom.It is highly preferred that it can enumerate by formula
(I-1)~(I-23) compound represented, particularly preferably, the compound represented by formula (I-1)~(I-6) can be enumerated.
Compound (Ia) for example can be anti-by the compound that formula (II) represents and the compound that is represented by formula (III) by making
Should, next, with formamide and synthesize the compound represented by formula (IV), make the compound represented by formula (IV) and by
The compound that formula (V) represents is reacted and is manufactured.
[in formula, R1~R12It is same as described above with M.X represents halogen atom.Zn-Represent the anion of n valencys, a, b represent nature
Number.But, a × n is equal with b × 2.]
For the containing ratio of compound (Ia), in the total amount of colorant (A), for example, for 1~100 mass %, preferably
For 50~100 mass %, more preferably 80~100 mass %, most preferably 90~100 mass %.
Colorant (A) may include dyestuff or pigment as the colorant other than compound (Ia).As dyestuff, can enumerate
Solvent dye, acid dyes, direct dyes, mordant dye etc., such as colour index (The Society of Dyers can be enumerated
And Colourists publish) in be classified as other than pigment the compound of substance with tone, dyeing notes (Se Ran societies)
Described in well known dyestuff.It as pigment, is not particularly limited, well known pigment can be used, such as can enumerate in color
The pigment of pigment is classified as in index (The Society of Dyers and Colourists publication).
Such as it can enumerate：
C.I. pigment yellow 1 (record of C.I. pigment yellows omitted below, only record serial number), 3,12,13,14,15,16,17,
20、24、31、53、83、86、93、94、109、110、117、125、128、137、138、139、147、148、150、153、154、
166th, the yellow uitramarines such as 173,194,214；
C.I. the orange pigments such as pigment orange 13,31,36,38,40,42,43,51,55,59,61,64,65,71,73；
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,175,176,177,180,192,209,
215th, the red pigments such as 216,224,242,254,255,264,265；
C.I. pigment blue 15,15：3、15：4、15：6th, the green pigments such as 60,80；
C.I. the violet pigments such as pigment violet 1,19,23,29,32,36,38；
C.I. viridine greens such as pigment Green 7,36,58 etc..
As workable dyestuff, can enumerate：
C.I. solvent yellow 4,14,15,23,24,38,62,63,68,82,94,98,99,162；
C.I. solvent red 45,49,125,130；
C.I. solvent orange 2,7,11,15,26,56；
C.I. solvent blue 4,5,37,67,70,90；
C.I. the green C.I. solvent dyes such as 1,4,5,7,34,35 of solvent,
C.I. Indian yellow 1,3,7,9,11,17,23,25,29,34,36,38,40,42,54,65,72,73,76,79,98,
99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、155、157、160、
161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、
212、214、220、221、228、230、232、235、238、240、242、243、251；
C.I. azogeramine, 4,8,14,17,18,26,27,29,31,34,35,37,42,44,50,57,66,73,88,
91、97、103、111、114、129、133、134、138、143、145、150、151、158、176、182、183、195、198、
206、211、215、216、217、227、228、249、252、257、258、260、261、266、268、270、274、277、280、
281、308、312、315、316、339、341、345、346、349、382、383、394、401、412、417、418、422、426；
C.I. acid orange 6,7,8,10,12,26,50,51,52,56,62,63,64,74,75,94,95,107,108,
169、173；
C.I. acid violet 6B, 7,17,19；
C.I. Blue VRS, 7,9,15,18,22,29,42,59,60,62,70,72,74,82,83,86,87,90,92,
93、100、102、103、104、113、117、120、126、130、131、142、147、151、154、158、161、166、167、
168、170、171、184、187、192、199、210、229、234、236、242、243、256、259、267、285、296、315、
335；
C.I. the C.I. acid dyes such as acid green 1,3,5,9,16,50,58,63,65,80,104,105,106,109；
C.I. directly Huang 2,33,34,35,38,39,43,47,50,54,58,68,69,70,71,86,93,94,95,98,
102、108、109、129、136、138、141；
C.I. directly red 79,82,83,84,91,92,96,97,98,99,105,106,107,172,173,176,177,
179、181、182、184、204、207、211、213、218、220、221、222、232、233、234、241、243、246、250；
C.I. direct orange 26,34,39,41,46,50,52,56,57,61,64,65,68,70,96,97,106,107；
C.I. direct purple 47,52,54,59,60,65,66,79,80,81,82,84,89,90,93,95,96,103,104；
C.I. directly indigo plant 1,2,6,8,15,22,25,41,57,71,76,78,80,81,84,85,86,90,93,94,95,
97、98、99、100、101、106、107、108、109、113、114、115、117、119、120、137、149、150、153、155、
156、158、159、160、161、162、163、164、165、166、167、168、170、171、172、173、188、189、190、
192、193、194、195、196、198、199、200、201、202、203、207、209、210、212、213、214、222、225、
226、228、229、236、237、238、242、243、244、245、246、247、248、249、250、251、252、256、257、
259、260、268、274、275、293；
C.I. the C.I. such as direct green 25,27,31,32,34,37,63,65,66,67,68,69,72,77,79,82 directly contaminate
Material,
C.I. the C.I. disperse dyes such as disperse yellow 54,76,
C.I. alkali blue 1,3,5,7,9,19,24,25,26,28,29,40,41,54,58,59,64,65,66,67,68；
C.I. 1 grade C.I. basic dyes of Viride Nitens,
C.I. active yellow 2,76,116；
C.I. 16 grade C.I. reactive dye of reactive orange,
C.I. mordant yellow 5,8,10,16,20,26,30,31,33,42,43,45,56,61,62,65；
C.I. mordant rouge 1,2,4,9,12,14,17,18,19,22,23,24,25,26,30,32,33,36,37,38,39,
41、43、45、46、48、53、56、63、71、74、85、86、88、90、94、95；
C.I. mordant dyeing orange 3,4,5,8,12,13,14,20,21,23,24,28,29,32,34,35,36,37,42,43,47,
48；
C.I. mordant dyeing purple 1,2,4,5,7,14,22,24,30,31,32,37,40,41,44,45,47,48,53,58；
C.I. mordant dyeing indigo plant 1,2,3,7,9,12,13,15,16,19,20,21,22,26,30,31,39,40,41,43,44,
49、53、61、74、77、83、84；
C.I. the C.I. mordant dyes such as viridon 1,3,4,5,10,15,26,29,33,34,35,41,43,53,
C.I. 1 grade C.I. reducing dyes of vat green etc..
For the content of colorant (A), relative to 100 mass parts of resin (B), preferably 0.1~100 mass parts, more
Preferably 1~50 mass parts, further preferably 5~30 mass parts.
＜ resins (B) ＞
Resin (B) is not particularly limited, preferably alkali soluble resin, more preferably have come from from unsaturated carboxylic acid and
The resin of the structural unit of at least one kind of (a) (hereinafter sometimes referred to " (a) ") selected in unsaturated carboxylic acid anhydrides.Resin (B) is preferred
Also with selected from from the cyclic annular ether structure with carbon number 2~4 and the monomer (b) of ethylenic unsaturated bond (hereinafter sometimes referred to
" (b) ") structural unit, from can with (a) be copolymerized monomer (c) (but, different from (a) and (b)) (hereinafter sometimes referred to
" (c) ") structural unit and side chain there is at least one of the structural unit structural unit of ethylenic unsaturated bond.
As (a), specifically, such as acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3 can be enumerated, 4,5,
6- tetrabydrophthalic anhydrides, mono succinate [2- (methyl) acryloyl-oxyethyl] ester etc., preferably acrylic acid, metering system
Acid, maleic anhydride.
(b) the cyclic annular ether structure preferably with carbon number 2~4 is (such as selected from oxirane ring, oxetanes ring and tetrahydrochysene
It is at least one kind of in furan nucleus) and (methyl) acryloxy monomer.
It should be explained that in this specification, " (methyl) acrylic acid " represents at least 1 in acrylic acid and methacrylic acid
Kind.The token of " (methyl) acryloyl group " and " (methyl) acrylate " etc. also has same meaning.
As (b), such as (methyl) glycidyl acrylate, vinylbenzyl glycidyl base ether, (first can be enumerated
Base) acrylic acid 3,4- epoxy tricyclics [5.2.1.02,6] last of the ten Heavenly stems ester, 3- ethyls -3- (methyl) acryloyloxymethyls oxetanes,
(methyl) tetrahydrofurfuryl acrylate etc., preferably (methyl) glycidyl acrylate, (methyl) acrylic acid 3,4- epoxy tricyclics
[5.2.1.02,6] last of the ten Heavenly stems ester, 3- ethyls -3- (methyl) acryloyloxymethyl oxetanes.
As (c), such as (methyl) methyl acrylate, (methyl) butyl acrylate, (methyl) acrylic acid ring can be enumerated
Own ester, (methyl) acrylic acid 2- methyl cyclohexyls, (methyl) acrylic acid tricyclic [5.2.1.02,6] decane -8- base esters, (methyl) third
Olefin(e) acid benzyl ester, (methyl) acrylic acid 2- hydroxy methacrylates, N-phenylmaleimide, N- N-cyclohexylmaleimides, N- benzyl horses
Come acid imide, styrene, vinyltoluene etc., optimization styrene, vinyltoluene, N-phenylmaleimide, N- cyclohexyl
Maleimide, N- benzyl maleimides etc..
It can be by making (b) addition in (a) and (c) with the resin in structural unit of the side chain with ethylenic unsaturated bond
Copolymer or (a) addition is made to be manufactured in the copolymer of (b) and (c).The resin can be make (a) addition in (b) with
(c) copolymer and then the resin for forming carboxylic acid anhydride reactant.
The weight average molecular weight of the polystyrene conversion of resin (B) is preferably 3000~100000, more preferably 5000~
50000, further preferably 5000~30000.
The dispersion degree [weight average molecular weight (Mw)/number-average molecular weight (Mn)] of resin (B) is preferably 1.1~6, more preferably
1.2~4.
The acid value of resin (B) is in terms of solid constituent conversion, preferably 50~170mg-KOH/g, more preferably 60~
150mg-KOH/g, further preferably 70~135mg-KOH/g.Wherein acid value be as in order to will resin (B) 1g neutralize needed for
Potassium hydroxide the value that measures of amount (mg), such as can be titrated and be obtained by using potassium hydroxide aqueous solution.
For the containing ratio of resin (B), relative to the total amount of solid constituent, preferably 7~65 mass %, more preferably
13~60 mass %, further preferably 17~55 mass %.
Wherein, " total amount of solid constituent " in this specification refers to eliminate from the total amount of colored resin composition molten
Amount after the content of agent.The total amount of solid constituent and it can for example use liquid chromatogram or gas relative to the content of its each ingredient
Analysis means well known to phase chromatography etc. measure.
The colored resin composition of the present invention may include polymerizable compound and/or polymerization initiator.It below sometimes will packet
Colored resin composition containing polymerizable compound and polymerization initiator is known as " colored curable resin composition ".In addition, with
Under polymerizable compound is known as " polymerizable compound (C) " sometimes, polymerization initiator is known as " polymerization initiator sometimes
(D)”。
＜ polymerizable compounds (C) ＞
Polymerizable compound (C) is polymerize using the living radical and/or acid that are generated by polymerization initiator (D)
Compound, such as the compound of the ethylenic unsaturated bond with polymerism can be enumerated etc., preferably (methyl) acrylate
Compound.
Wherein, polymerizable compound (C) is preferably the polymerizable compound with 3 or more ethylenic unsaturated bonds.As
Such polymerizable compound, such as trimethylolpropane tris (methyl) acrylate, pentaerythrite three (methyl) can be enumerated
Acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, six (first of dipentaerythritol
Base) acrylate etc..
The weight average molecular weight of polymerizable compound (C) be preferably more than 150 and 2900 hereinafter, more preferably more than 250 and
Less than 1500.
In the case of comprising polymerizable compound (C), for the containing ratio of polymerizable compound (C), relative to solid
The total amount of ingredient, preferably 7~65 mass %, more preferably 13~60 mass %, further preferably 17~55 mass %.
＜ polymerization initiators (D) ＞
Polymerization initiator (D) as long as living radical, acid etc. are generated under the action of light, heat and polymerization can be caused
Compound is then not particularly limited, and can use well known polymerization initiator.Cause as the polymerization for generating living radical
Agent, such as N- benzoyloxys -1- (4- Phenylsulfanyls phenyl) butane -1- ketone -2- imines, N- benzoxies can be enumerated
Base -1- (4- Phenylsulfanyls phenyl) octane -1- ketone -2- imines, N- benzoyloxys -1- (4- Phenylsulfanyls phenyl) -3-
Cyclopenta propane -1- ketone -2- imines, 2- methyl -2- morpholinoes -1- (4- methylsulfanyls phenyl) propane -1- ketone, 2- dimethyl
Amino -1- (4- morphlinophenyls) -2- benzyl butane -1- ketone, 1- hydroxycyclohexylphenylketones, bis- (the trichloromethyl) -6- of 2,4-
Piperonyl -1,3,5- triazines, 2,4,6- trimethyl benzoyl diphenyl base phosphine oxides, 2,2 '-bis- (2- chlorphenyls) -4,4 ', 5,
5 '-tetraphenyl bisglyoxaline etc..
In the case of comprising polymerization initiator (D), for the content of polymerization initiator (D), relative to resin (B) and
100 mass parts of total amount of polymerizable compound (C), more preferably preferably 0.1~30 mass parts, 1~20 mass parts.If
The content of polymerization initiator (D) then with high sensitivity, the tendency for shortening the time for exposure, therefore is filtered in above-mentioned range
The productivity of color device improves.
The colored resin composition of the present invention may include polymerization trigger auxiliary agent.Polymerization trigger auxiliary agent is known as sometimes below
" polymerization trigger auxiliary agent (D1) ".
＜ polymerization trigger auxiliary agents (D1) ＞
Polymerization trigger auxiliary agent (D1) is the polymerization for promoting the polymerizable compound for having caused polymerization by polymerization initiator
Compound or sensitizer.In the case of comprising polymerization trigger auxiliary agent (D1), usually it is applied in combination with polymerization initiator (D).
As polymerization trigger auxiliary agent (D1), it can enumerate 4,4 '-bis- (dimethylamino) benzophenone (common name Michler's keton),
4,4 '-bis- (diethylamino) benzophenone, 9,10- dimethoxys anthracene, 2,4- diethyl thioxanthones, N-phenylglycine etc..
In the case of using these polymerization trigger auxiliary agents (D1), relative to the total of resin (B) and polymerizable compound (C)
100 mass parts are measured, content is preferably 0.1~30 mass parts, more preferably 1~20 mass parts.If polymerization trigger auxiliary agent
(D1) amount in the range, then further can form colored pattern, the productivity of colour filter is tended to improve with high sensitivity.
The colored resin composition of the present invention preferably comprises solvent.Solvent is known as " solvent (E) " sometimes below.
＜ solvents (E) ＞
Solvent (E) is not particularly limited, solvent usually used in the field can be used.Such as can to enumerate ester output molten
Agent (molecule includes-COO- and the solvent without-O-), ether solvents (molecule includes-O- and the solvent without-COO-), ether-ether are molten
Agent (molecule includes the solvent of-COO- and-O-), ketone solvent (molecule includes-CO- and the solvent without-COO-), alcoholic solvent (divide
Son includes OH and the solvent without-O- ,-CO- and-COO-), aromatic hydrocarbon solvents, amide solvent, dimethyl sulfoxide (DMSO) etc..
As solvent, ethyl lactate, butyl lactate, 2- hydroxy-methyl isobutyl acids, n-butyl acetate, butyric acid second can be enumerated
The ester solvents such as ester, butyl butyrate, ethyl pyruvate, methyl acetoacetate, adnoral acetate and gamma-butyrolacton (molecule includes-
COO- and the solvent without-O-)；Ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3- methoxyl groups -1-
The ether solvents such as butanol, diethylene glycol dimethyl ether, diethylene glycol (DEG) methyl ethyl ether (molecule includes-O- and the solvent without-COO-)；3-
Methoxy methyl propionate, 3- ethoxyl ethyl propionates, acetic acid 3- methoxybutyls, propylene glycol monomethyl ether, ethylene glycol
The ether-ethers such as single monoethyl ether acetate, diethylene glycol monoethyl ether acetate solvent (molecule includes the solvent of-COO- and-O-)；4- hydroxyls
(molecule includes-CO- and is free of-COO-'s the ketone solvents such as base -4-methyl-2 pentanone, heptanone, 4-methyl-2 pentanone, cyclohexanone
Solvent)；The alcoholic solvents such as butanol, cyclohexanol, propylene glycol (molecule includes OH and the solvent without-O- ,-CO- and-COO-)；N,N-
Amide solvents such as dimethylformamide, DMAC N,N' dimethyl acetamide and N-Methyl pyrrolidone etc..
As solvent, more preferable propylene glycol monomethyl ether, propylene glycol monomethyl ether, ethyl lactate, N- methyl pyrroles
Pyrrolidone and 3- ethoxyl ethyl propionates.
In the case of comprising solvent (E), for the containing ratio of solvent (E), combined relative to the pigmentary resin of the present invention
The total amount of object, preferably 70~95 mass %, more preferably 75~92 mass %.In other words, the solid of colored resin composition
The total amount of ingredient is preferably 5~30 mass %, more preferably 8~25 mass %.If the content of solvent (E) is in above-mentioned range
Interior, then flatness when being coated with becomes good, the in addition no deficiency of colour saturation when foring colour filter, therefore special with display
Property becomes good tendency.
＜ other compositions ＞
The colored resin composition of the present invention may include levelling agent, filler, other high-molecular compounds, close as needed
Close well known additive in the technical fields such as accelerating agent, antioxidant, light stabilizer, chain-transferring agent.
The manufacturing method ＞ of ＜ colored resin compositions
The colored resin composition of the present invention can be by by colorant (A), resin (B) and used as needed
Polymerizable compound (C), polymerization initiator (D), solvent (E) and other compositions are mixed and are prepared.
The manufacturing method ＞ of ＜ colour filters
As by the present invention colored resin composition manufacture colored pattern method, can enumerate photoetching process, ink-jet method,
Print process etc..Wherein, preferred photoetching process.
Colored resin composition using the present invention can make the high colour filter of contrast.The colour filter can be used as
The colour filter used in the display devices such as liquid crystal display device, organic el device, Electronic Paper and solid-state imager.
Embodiment
The present invention is described in more detail by the following examples, but the present invention is not limited by these embodiments.In example,
It represents % and part of content or usage amount, is then quality criteria as long as no special instructions.
Hereinafter, the structure of compound passes through quality analysis (LC：1200 type of Agilent systems, MAS：Agilent LC/MSD
Type) confirm.
(synthesis example 1)
5.0 parts of phthalonitrile (Tokyo chemical conversion (strain) manufacture) is made to be dissolved in dehydration diethyl ether (Northeast chemistry (strain) manufacture)
In 40 parts, -20 DEG C are cooled to, instills 42.6 parts of the 1M tetrahydrofuran solutions (Northeast chemistry (strain) manufacture) of phenyl-magnesium-bromide.Drop
After entering, room temperature is warming up to, has been stirred 3 hours.After obtained reaction solution is concentrated, addition is previously added first of the magnesium sulfate through dehydration
280 parts of amide (Tokyo chemical conversion (strain) manufacture), has been stirred 3 hours at 140 DEG C.It is cooled to room temperature after reaction, will be precipitated
Solid filtering.After obtained screening is cleaned with 700 parts of methanol/water mixed liquor, it was dried under reduced pressure for 1 evening at 60 DEG C, obtains
1.7 parts of the compound represented by (formula IV -1).Yield is 22%.
Identification：(quality analysis) ionization mode=ESI+：M/z=[M+H]+398.5
Definite quality：397.2
(synthesis example 2)
Next, add in 0.5 part of the compound represented by formula (IV-1), zinc acetate (and Wako Pure Chemical Industries (strain) manufacture)
0.3 part, 0.325 part of diisopropyl ethyl amine (Tokyo chemical conversion (strain) manufacture), n-butyl alcohol (and Wako Pure Chemical Industries (strain) manufacture) 10
Part, it has carried out being heated to reflux 6 hours at 110 DEG C.It is cooled to room temperature after reaction, the solid of precipitation is filtered.It will obtain
Solid cleaned with 50 parts of chloroform in heating after, be dried under reduced pressure for 1 evening at 60 DEG C, obtained the chemical combination represented by formula (I-1)
0.4 part of object.Yield is 76%.
Identification：(quality analysis) ionization mode=ESI+：M/z=[M+H]+857.0
Definite quality：856.23
(synthesis example 3)
2.0 parts of 3- chlore O-phthalic acids nitrile (and Wako Pure Chemical Industries (strain) manufacture) is made to be dissolved in dehydration diethyl ether (Northeast chemistry
(strain) manufactures) in 28 parts, -20 DEG C are cooled to, instills the 1M tetrahydrofuran solutions (Northeast chemistry (strain) manufacture) of phenyl-magnesium-bromide
13.2 parts.After instillation, room temperature is warming up to, has been stirred 3 hours.After obtained reaction solution is concentrated, addition is previously added magnesium sulfate
75 parts of the formamide (Tokyo chemical conversion (strain) manufacture) through dehydration, has been stirred 30 minutes at 140 DEG C.It is cooled to room after reaction
Temperature filters the solid of precipitation.After obtained screening is cleaned with 375 parts of methanol/water mixed liquor, 1 is dried under reduced pressure at 60 DEG C
Evening has obtained 1.2 parts of the compound represented by (formula IV -2).Yield is 43%.
Identification：(quality analysis) ionization mode=ESI+：M/z=[M+H]+466.5
Definite quality：465.1
(synthesis example 4)
Next, add in 4.0 parts of the compound represented by formula (IV-2), zinc acetate (and Wako Pure Chemical Industries (strain) manufacture)
1.8 parts, 2.0 parts of diisopropyl ethyl amine (Tokyo chemical conversion (strain) manufacture), n-butyl alcohol (and Wako Pure Chemical Industries (strain) manufacture) 120
Part, it has carried out being heated to reflux for 3 hours at 110 DEG C.It is cooled to room temperature after reaction, the solid of precipitation is filtered.It will obtain
Solid chloroform, tetrahydrofuran heating clean after, be dried under reduced pressure at 60 DEG C 1 evening, obtained the chemical combination represented by formula (I-4)
2.2 parts of object.Yield is 55%.
Identification：(quality analysis) ionization mode=ESI+：M/z=[M+H]+994.8
Definite quality：992.07
(synthesis example 5)
It flows into suitable nitrogen in the flask with reflux condenser, dropping funel and blender, is replaced into nitrogen atmosphere,
371 parts of acetic acid 1- methoxyl group -2- propyl ester is packed into, is heated to 85 DEG C while stirring.It is dripped next, lasting 4 hours in the flask
Enter 54 parts of acrylic acid, acrylic acid 3,4- epoxy tricyclics [5.2.1.02,6] decane -8- base esters and acrylic acid 3,4- epoxy tricyclics
[5.2.1.02,6] decane -9- base esters 225 parts of mixture (trade name " E-DCPA ", Co., Ltd. Daicel manufacture), vinyl
The mixed solution of 81 parts of toluene (isomer mixture), 80 parts of acetic acid 1- methoxyl group -2- propyl ester.On the other hand, it lasts 5 hours and drips
Enter 30 parts of polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) is dissolved in 160 parts of acetic acid 1- methoxyl group -2- propyl ester and
Into solution.After the instillation of initiator solution, after maintaining 4 hours at the same temperature, room temperature is cooled to, is glued with Type B
The viscosity of degree (23 DEG C) measure of meter is 246mPas.The solid constituent of resin (B-1) solution is 37.5%, solid constituent conversion
Acid value is 115mg-KOH/g.The weight average molecular weight Mw of the copolymer of generation is 10600, and dispersion degree [Mw/Mn] is 2.01.Resin
(B-1) there is following structural unit.
Resin polystyrene conversion weight average molecular weight (Mw) and number-average molecular weight (Mn) measure use GPC method,
It is carried out under conditions of below.
Device：HLC-8120GPC (Tosoh (strain) manufacture)
Column：TSK-GELG2000HXL
Column temperature：40℃
Solvent：THF
Flow velocity：1.0mL/min
It is detected liquid solid component concentration；0.001~0.01 mass %
Injection rate：50μL
Detector：RI
Correction standard substance：TSK STANDARD POLYSTYRENE
F-40, F-4, F-288, A-2500, A-500 (Tosoh (strain) manufacture)
The ratio between weight average molecular weight and number-average molecular weight that polystyrene obtained above is converted (Mw/Mn) are as dispersion
Degree.
[Examples 1 to 2, comparative example 1]
[preparation of colored resin composition]
Each ingredient is mixed by the number shown in table 1, has obtained colored resin composition.
【Table 1】
Table 1
Note 1：
Note 2：The liquid that the right ingredient in table is mixed, pigment is made fully to disperse using ball mill
Note 3：Solid constituent conversion amount
Note 4：The solvent used other than face material dispersion liquid
Note 5：It is manufactured using the method described in the synthetic example 1 of Japanese Unexamined Patent Publication 2004-70342 bulletins
[making of colored pattern]
In the glass substrate (EAGLE 2000 of 5cm square；Corning Incorporated manufacture) on using spin-coating method be coated with pigmentary resin
After composition, prebake 3 minutes at 100 DEG C have obtained coloring compositions nitride layer.After letting cool, make to form coloring compositions nitride layer
Substrate and quartz glass photomask between be divided into 100 μm, use exposure machine (TME-150RSK；Foretell プ Us Application (strain) to manufacture),
Under air atmosphere, use 150mJ/cm2Light exposure (365nm benchmark) carried out light irradiation.As photomask, formation has been used
The photomasks of 100 μm of lines and space pattern.Coloring compositions nitride layer after light is irradiated is including nonionic surfactants
0.12% and potassium hydroxide 0.04% water system developer solution at 24 DEG C immersion development 60 seconds, after washing, in an oven, 150
It is baked after twenty minutes at DEG C, has obtained colored pattern.
As a result the colored pattern obtained with light microscope observation by the colored resin composition of Examples 1 and 2 confirms and divides
Discern 100 μm of lines and gap.
[film thickness measuring]
Use film thickness measuring device (DEKTAK (registered trademark) 3；Japanese vacuum technique (strain) manufacture) determine
The film thickness of colored pattern.It shows the result in table 2.
[making of coloring film]
In the glass substrate (EAGLE 2000 of 5cm square；Corning Incorporated manufactures) on, pigmentary resin is coated with using spin-coating method
After composition is so that the film thickness after baking becomes the film thickness identical with above-mentioned colored pattern afterwards, prebake 3 minutes at 100 DEG C.
After letting cool, exposure machine (TME-150RSK is used；Foretell プ Us Application (strain) to manufacture), under air atmosphere, use 150mJ/cm2Exposure
Amount (365nm benchmark) has carried out light irradiation.After light irradiation, baked, obtained after twenty minutes in an oven, at 150 DEG C
Color film.
[contrast evaluation]
For obtained coloring film, contrast meter (CT-1 is used；Pot slope motor (strain) manufacture, color evaluating BM-
5A；Foretell the manufacture of プ U ソ Co., Ltd., light source；F-10, light polarizing film；Pot slope motor (strain) manufactures) determine contrast.It should say
Bright, blank value during measure is 30000.It shows the result in table 2.
【Table 2】
| Film thickness (μm) | Contrast | |
| Embodiment 1 | 20 | 27100 |
| Embodiment 2 | 20 | 22100 |
| Comparative example 1 | 20 | 8200 |
The contrast of coloring film that the colored resin composition using embodiment identified above obtains is high.Thus may be used
Know, coloring film, the colored pattern obtained by the colored resin composition of the present invention can be used as colour filter, include the colour filter
The display characteristic of display device is excellent, the camera shooting excellent of the solid-state imager comprising the colour filter.
Industrial availability
Colored curable resin composition using the present invention, being capable of the high colour filter of degree of being contrasted.
Claims (6)
1. colored resin composition, which contain toner and resin, the colorant includes the compound represented by formula (Ia),
In formula (Ia), R1~R4Each independently represent can be with the carbon number 6~20 of substituent group aromatic hydrocarbyl or can be with
The aromatic heterocycle of the carbon number 3~19 of substituent group,
R5~R12Each independently represent hydrogen atom, halogen atom, cyano, nitro, can have substituent group carbon number 1~20 it is full
With alkyl, can be with the carbon number 6~20 of substituent group aromatic hydrocarbyl or can the aromatic series with the carbon number 3~19 of substituent group
Heterocycle, R5With R6、R7With R8、R9With R10And R11With R12It can respectively be combined with each other and form the aromatic series that can have substituent group
Hydrocarbon ring,
M represents the metallic atom of divalent or the trivalent with substituent group or the metallic atom of 4 valencys.
2. colored resin composition according to claim 1 also includes polymerizable compound and polymerization initiator.
3. the colour filter formed by colored resin composition according to claim 1 or 2.
4. display device, it includes colour filters according to claim 3.
5. solid-state imager, it includes colour filters according to claim 3.
6. the compound represented by formula (Ib ')：
In formula (Ib '), ring A1~A4The aromatic series hydrocarbon ring of substituent group, but, ring A can be had by each independently representing1~A4In extremely
Few one is the aromatic series hydrocarbon ring with substituent group,
R1~R4Each independently represent can be with the carbon number 6~20 of substituent group aromatic hydrocarbyl or can be with substituent group
The aromatic heterocycle of carbon number 3~19,
M represents the metallic atom of divalent or the trivalent with substituent group or the metallic atom of 4 valencys.
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| JP2016-251978 | 2016-12-26 | ||
| JP2016251978A JP6912885B2 (en) | 2016-12-26 | 2016-12-26 | Colored resin compositions, color filters, display devices, solid-state image sensors, and compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103454859A (en) * | 2012-05-29 | 2013-12-18 | 住友化学株式会社 | Colored curable resin composition |
| CN103732692A (en) * | 2011-09-30 | 2014-04-16 | 富士胶片株式会社 | Colored curable composition, color filter, method for producing color filter, and display device |
| CN105388705A (en) * | 2014-09-01 | 2016-03-09 | 东友精细化工有限公司 | Coloured photosensitive resin composition |
| CN105392806A (en) * | 2013-07-09 | 2016-03-09 | 富士胶片株式会社 | Coloring composition, cured film, color filter, method for producing color filter, solid-state imaging element, and image display device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH1192479A (en) * | 1997-09-17 | 1999-04-06 | Mitsui Chem Inc | Optical recording medium |
| JP4368157B2 (en) | 2002-07-24 | 2009-11-18 | 大日本印刷株式会社 | Green pigment for color filter, green pigment dispersion, photosensitive coloring composition, color filter, and liquid crystal panel |
| WO2010133208A1 (en) * | 2009-05-19 | 2010-11-25 | Technische Universität Dresden | Semiconducting component |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103732692A (en) * | 2011-09-30 | 2014-04-16 | 富士胶片株式会社 | Colored curable composition, color filter, method for producing color filter, and display device |
| CN103454859A (en) * | 2012-05-29 | 2013-12-18 | 住友化学株式会社 | Colored curable resin composition |
| CN105392806A (en) * | 2013-07-09 | 2016-03-09 | 富士胶片株式会社 | Coloring composition, cured film, color filter, method for producing color filter, solid-state imaging element, and image display device |
| CN105388705A (en) * | 2014-09-01 | 2016-03-09 | 东友精细化工有限公司 | Coloured photosensitive resin composition |
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| TW201823372A (en) | 2018-07-01 |
| JP2018104551A (en) | 2018-07-05 |
| KR20180075391A (en) | 2018-07-04 |
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| CN108239429B (en) | 2021-10-22 |
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