JP2011215537A - Colored composition for color filter, and color filter using the same - Google Patents
Colored composition for color filter, and color filter using the same Download PDFInfo
- Publication number
- JP2011215537A JP2011215537A JP2010085872A JP2010085872A JP2011215537A JP 2011215537 A JP2011215537 A JP 2011215537A JP 2010085872 A JP2010085872 A JP 2010085872A JP 2010085872 A JP2010085872 A JP 2010085872A JP 2011215537 A JP2011215537 A JP 2011215537A
- Authority
- JP
- Japan
- Prior art keywords
- group
- color filter
- alkyl group
- squarylium compound
- same
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910001428 transition metal ion Inorganic materials 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 238000004040 coloring Methods 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- -1 compound ions Chemical class 0.000 abstract description 36
- 238000000034 method Methods 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- SXOQOOQUBDERIZ-UHFFFAOYSA-N 3,4-dichlorocyclobut-3-ene-1,2-dione Chemical compound ClC1=C(Cl)C(=O)C1=O SXOQOOQUBDERIZ-UHFFFAOYSA-N 0.000 description 2
- XFTUGNYHMOMVDH-UHFFFAOYSA-N 3-chloro-4-(4-methoxyphenyl)cyclobut-3-ene-1,2-dione Chemical compound C1=CC(OC)=CC=C1C1=C(Cl)C(=O)C1=O XFTUGNYHMOMVDH-UHFFFAOYSA-N 0.000 description 2
- SOAGITVEXAAUCT-UHFFFAOYSA-N 3-chloro-4-[4-(dibutylamino)phenyl]cyclobut-3-ene-1,2-dione Chemical compound C1=CC(N(CCCC)CCCC)=CC=C1C1=C(Cl)C(=O)C1=O SOAGITVEXAAUCT-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 2
- 229910001453 nickel ion Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FEUFEGJTJIHPOF-UHFFFAOYSA-N 2-butyl acrylic acid Chemical compound CCCCC(=C)C(O)=O FEUFEGJTJIHPOF-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-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
- SZBNZTGCAMLMJY-UHFFFAOYSA-N 3,4-dimethoxycyclobut-3-ene-1,2-dione Chemical compound COC1=C(OC)C(=O)C1=O SZBNZTGCAMLMJY-UHFFFAOYSA-N 0.000 description 1
- IDBUSYRVNGPBPL-UHFFFAOYSA-M 3-ethyl-2-methyl-1,3-thiazol-3-ium;iodide Chemical group [I-].CCN1C=CS[C+]1C IDBUSYRVNGPBPL-UHFFFAOYSA-M 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- NJMYQRVWBCSLEU-UHFFFAOYSA-N 4-hydroxy-2-methylidenebutanoic acid Chemical compound OCCC(=C)C(O)=O NJMYQRVWBCSLEU-UHFFFAOYSA-N 0.000 description 1
- VWFBZWHAIIDHRT-UHFFFAOYSA-N 5-methyl-2-propyl-4h-pyrazol-3-one Chemical compound CCCN1N=C(C)CC1=O VWFBZWHAIIDHRT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- OISVGAHOWZSLJL-UHFFFAOYSA-N [Ni].C1(C(C=C1)=O)=O Chemical compound [Ni].C1(C(C=C1)=O)=O OISVGAHOWZSLJL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000003180 beta-lactone group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical group CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910001429 cobalt ion Inorganic materials 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical group CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical group C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940078487 nickel acetate tetrahydrate Drugs 0.000 description 1
- OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005447 octyloxy group Chemical group [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])O* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical group CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical group CCC#N FVSKHRXBFJPNKK-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
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Abstract
Description
本発明は、スクアリリウム化合物を含有することを特徴とするカラーフィルター用着色組成物とそれを用いたカラーフィルターに関する。 The present invention relates to a coloring composition for a color filter containing a squarylium compound and a color filter using the same.
カラーフィルターは高い透明性が必要とされるために、色素を用いて着色する染色法が行われてきた。例えば、被染色性のフォトレジストをパターン露光、現像することによりパターンを形成し、次いでフィルター色の色素を染色する方法を全フィルター色について順次繰り返すことにより、カラーフィルターを製造することができる。
染色法以外にもポジ型レジストを用いる方法によってもカラーフィルターを製造することができる。これらの方法により製造されるカラーフィルターは色素を用いているために透過率が高く、光学特性に優れているが、耐光性や耐熱性に限界がある。
また、顔料を用いたカラーフィルターでは、色素のような光学特性を得ることは困難であり、かつ、粘度や耐熱性に劣る欠点があった(特許文献1)。
Since color filters are required to have high transparency, a dyeing method for coloring with a dye has been performed. For example, a color filter can be produced by sequentially repeating a method of forming a pattern by pattern-exposing and developing a dyeable photoresist and then dyeing a filter color dye for all filter colors.
In addition to the dyeing method, a color filter can be produced by a method using a positive resist. The color filter produced by these methods has high transmittance and excellent optical properties because it uses a dye, but has limitations in light resistance and heat resistance.
In addition, a color filter using a pigment has a drawback that it is difficult to obtain optical characteristics such as a pigment and is inferior in viscosity and heat resistance (Patent Document 1).
本発明の目的は、粘度が低いカラーフィルター用着色組成物とそれを用いた耐熱性に優れるカラーフィルターを提供することである。 An object of the present invention is to provide a coloring composition for a color filter having a low viscosity and a color filter having excellent heat resistance using the same.
本発明者らは、鋭意検討をした結果、スクアリリウム化合物を用いたカラーフィルター用着色組成物とカラーフィルターが上記課題を解決できることを見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventors have found that a coloring composition for a color filter using a squarylium compound and a color filter can solve the above problems, and have completed the present invention.
すなわち、本発明は以下に示すものである。 That is, the present invention is as follows.
第一の発明は、下記一般式(A)〜(D)で表されるスクアリリウム化合物イオンと、水素イオン又は遷移金属イオンとからなるスクアリリウム化合物を含有することを特徴とする着色組成物である。 1st invention is a coloring composition characterized by including the squarylium compound which consists of a squarylium compound ion represented by the following general formula (A)-(D), and a hydrogen ion or a transition metal ion.
第二の発明は、バインダー成分を含有することを特徴とする第一の発明に記載のカラーフィルター用着色組成物である。 2nd invention is a coloring composition for color filters as described in 1st invention characterized by containing a binder component.
第三の発明は、第一又は第二の発明に記載のカラーフィルター用着色組成物を含有する層を備えることを特徴とするカラーフィルターである。 3rd invention is a color filter provided with the layer containing the coloring composition for color filters as described in 1st or 2nd invention.
本発明によれば、粘度に優れるカラーフィルター用着色組成物とそれを用いた耐熱性に優れるカラーフィルターを提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the coloring composition for color filters which is excellent in a viscosity, and the color filter which is excellent in heat resistance using the same can be provided.
カラーフィルター用着色組成物について説明する。 The coloring composition for color filters will be described.
本発明のカラーフィルター用着色組成物は、一般式(A)〜(D)で表されることを特徴とするスクアリリウム化合物を着色色素として用い、該スクアリリウム化合物を有機溶媒に分散させることにより得ることができる。
本発明のカラーフィルター用着色組成物は、有機溶媒以外にも、バインダー成分、シリカ粒子、添加剤等を含んでも良い。
The coloring composition for a color filter of the present invention is obtained by using a squarylium compound represented by the general formulas (A) to (D) as a coloring pigment and dispersing the squarylium compound in an organic solvent. Can do.
The coloring composition for a color filter of the present invention may contain a binder component, silica particles, an additive and the like in addition to the organic solvent.
着色色素は、一般式(A)〜(D)で表されるスクアリリウム化合物と、水素イオン又は遷移金属イオンとからなるスクアリリウム化合物である。 A coloring pigment | dye is a squarylium compound which consists of a squarylium compound represented by general formula (A)-(D), and a hydrogen ion or a transition metal ion.
一般式(A)中、R1〜R6は、同一又は異なってもよい水素、ハロゲン原子、置換基を有してもよいアルキル基、ハロゲン化アルキル基、シアノアルキル基、アルコキシ基、フェニルアルキル基、アルキルスルホン酸基を示し、R2とR3、R3とR4、R5とR6、R6とR1は連結して炭化水素環を形成してもよい。 In general formula (A), R 1 to R 6 are the same or different hydrogen, halogen atom, optionally substituted alkyl group, halogenated alkyl group, cyanoalkyl group, alkoxy group, phenylalkyl. R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 1 may be linked to form a hydrocarbon ring.
一般式(B)中、R7は、水素又は置換基を有してもよいアルキル基であり、R8〜R11は、同一又は異なってもよい水素、ハロゲン原子、置換基を有してもよいアルキル基、ハロゲン化アルキル基、シアノアルキル基、アルコキシ基、フェニルアルキル基、アルキルスルホン酸基を示し、R8とR9、R10とR11は連結して炭化水素環を形成してもよい。 In general formula (B), R 7 is hydrogen or an alkyl group which may have a substituent, and R 8 to R 11 have the same or different hydrogen, halogen atom and substituent. Represents an alkyl group, a halogenated alkyl group, a cyanoalkyl group, an alkoxy group, a phenylalkyl group, an alkylsulfonic acid group, and R 8 and R 9 , R 10 and R 11 are linked to form a hydrocarbon ring. Also good.
一般式(C)中、R12〜R14は、同一又は異なってもよい水素、ハロゲン原子、置換基を有してもよいアルキル基、ハロゲン化アルキル基、シアノアルキル基、アルコキシ基、フェニルアルキル基、アルキルスルホン酸基を示す。 In general formula (C), R 12 to R 14 may be the same or different hydrogen, halogen atom, optionally substituted alkyl group, halogenated alkyl group, cyanoalkyl group, alkoxy group, phenylalkyl. Group, an alkylsulfonic acid group.
一般式(D)中、R15〜R19は、同一又は異なってもよい水素、ハロゲン原子、置換基を有しても良いアルキル基、ハロゲン化アルキル基、シアノアルキル基、アルコキシ基、フェニルアルキル基、アルキルスルホン酸基を示し、XはO、S、N−R20、C−R21R22(R20〜R22は同一又は異なってもよい水素、ハロゲン原子、置換基を有してもよいアルキル基、ハロゲン化アルキル基、シアノアルキル基、アルコキシ基、フェニルアルキル基、アルキルスルホン酸基を示す。)を示す。 In the general formula (D), R 15 to R 19 are the same or different hydrogen, halogen atom, optionally substituted alkyl group, halogenated alkyl group, cyanoalkyl group, alkoxy group, phenylalkyl. Group, an alkylsulfonic acid group, X is O, S, N—R 20 , C—R 21 R 22 (R 20 to R 22 may be the same or different and each has a hydrogen atom, a halogen atom, or a substituent. An alkyl group, a halogenated alkyl group, a cyanoalkyl group, an alkoxy group, a phenylalkyl group, or an alkylsulfonic acid group.
遷移金属イオンとしては、ニッケルイオン、鉄イオン、銅イオン、コバルトイオン、亜鉛イオン、マグネシウムイオン等が挙げられ、特にニッケルイオンが好ましく挙げられる。 Examples of transition metal ions include nickel ions, iron ions, copper ions, cobalt ions, zinc ions, magnesium ions and the like, with nickel ions being particularly preferred.
上記ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられ、好ましくはフッ素原子が挙げられる。 As said halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, Preferably a fluorine atom is mentioned.
上記置換基を有してもよいアルキル基としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、tert−ブチル基、sec−ブチル基、n−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、n−デシル基、n−ドデシル基、n−オクタデシル基等の炭素数1〜20の直鎖又は分岐のアルキル基が挙げられ、炭素数1〜10の直鎖又は分岐のアルキル基が好ましく挙げられる。 Examples of the alkyl group which may have a substituent include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, sec-butyl group, n-pentyl group, n- Examples thereof include straight-chain or branched alkyl groups having 1 to 20 carbon atoms such as hexyl group, n-heptyl group, n-octyl group, n-decyl group, n-dodecyl group and n-octadecyl group. Preferred are 10 linear or branched alkyl groups.
上記ハロゲン化アルキル基において、炭素数は1〜12の直鎖又は分岐のハロゲン化アルキル基である。ハロゲン化アルキル基のハロゲン原子としては、スクアリリウム化合物の感度や樹脂との相溶性を向上させる効果に優れる点から、特にフッ素原子、すなわちフッ化アルキル基が好ましい。 The halogenated alkyl group is a linear or branched halogenated alkyl group having 1 to 12 carbon atoms. The halogen atom of the halogenated alkyl group is particularly preferably a fluorine atom, that is, a fluorinated alkyl group, from the viewpoint of excellent effects of improving the sensitivity of the squarylium compound and the compatibility with the resin.
上記フッ化アルキル基としては、トリフルオロメチル基、2,2,2−トリフルオロエチル基、3,3,3−トリフルオロプロピル基、4,4,4−トリフルオロブチル基、5,5,5−トリフルオロペンチル基、6,6,6−トリフルオロヘキシル基、8,8,8−トリフルオロオクチル基、2−メチル−3,3,3−トリフルオロプロピル基、ペルフルオロエチル基、ペルフルオロプロピル基、ペルフルオロブチル基、ペルフルオロヘキシル基、ペルフルオロオクチル基、2−トリフルオロメチル−ペルフルオロプロピル基等が挙げられる。 Examples of the fluorinated alkyl group include trifluoromethyl group, 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 5,5,5, 5-trifluoropentyl group, 6,6,6-trifluorohexyl group, 8,8,8-trifluorooctyl group, 2-methyl-3,3,3-trifluoropropyl group, perfluoroethyl group, perfluoropropyl Group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, 2-trifluoromethyl-perfluoropropyl group and the like.
上記シアノアルキル基としては、炭素数1〜10の直鎖又は分岐のシアノアルキル基であることが好ましく、置換されているシアノ基の数は、1〜3個が好ましい。特に好ましくは、プロピオニトリル基、ブチロニトリル基、ペンチルニトリル基、1−メチルプロピオニトリル基、1−メチルブチロニトリル基等が挙げられる。 The cyanoalkyl group is preferably a linear or branched cyanoalkyl group having 1 to 10 carbon atoms, and the number of substituted cyano groups is preferably 1 to 3. Particularly preferred are propionitrile group, butyronitrile group, pentylnitrile group, 1-methylpropionitrile group, 1-methylbutyronitrile group and the like.
上記アルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、2ーメトキシエトキシ基、ペンチルオキシ基、ヘキシルオキシ基、オクチルオキシ基、デシルオキシ基、メトキシメチル基、メトキシエチル基、メトキシプロピル基、メトキシブチル基、メトキシヘキシル基、メトキシオクチル基、エトキシエチル基、エトキシエチル基、エトキシプロピル基、エトキシブチル基、エトキシヘキシル基、エトキシオクチル基、プロポキシメチル基、プロポキシプロピル基、プロポキシヘキシル基、ブトキシエチル基等の炭素数1〜18の直鎖又は分岐のアルコキシ基が挙げられる。 As the alkoxy group, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, 2-methoxyethoxy group, pentyloxy group, hexyloxy group, octyloxy group, decyloxy group, methoxymethyl group, methoxyethyl group , Methoxypropyl group, methoxybutyl group, methoxyhexyl group, methoxyoctyl group, ethoxyethyl group, ethoxyethyl group, ethoxypropyl group, ethoxybutyl group, ethoxyhexyl group, ethoxyoctyl group, propoxymethyl group, propoxypropyl group, propoxy C1-C18 linear or branched alkoxy groups, such as a hexyl group and a butoxyethyl group, are mentioned.
上記フェニルアルキル基としては、アルキル基の炭素数が1〜8のものが好ましく、フェニル基は置換基を有してもよく、アルキル基、水酸基、スルホン酸基、アルキルスルホン酸基、ニトロ基、アミノ基、アルコキシ基、ハロゲン化アルキル基及びハロゲンからなる群から少なくとも1種の置換基を有してもよい。また、フェニルアルキル基として、ベンジル基、フェネチル基、フェニルプロピル基、フェニル−α−メチルプロピル基、フェニル−β−メチルプロピル基、フェニルブチル基、フェニルペンチル基等が挙げられる。 As said phenylalkyl group, the C1-C8 thing of an alkyl group is preferable, and a phenyl group may have a substituent, an alkyl group, a hydroxyl group, a sulfonic acid group, an alkylsulfonic acid group, a nitro group, You may have an at least 1 sort (s) of substituent from the group which consists of an amino group, an alkoxy group, a halogenated alkyl group, and a halogen. Examples of the phenylalkyl group include benzyl group, phenethyl group, phenylpropyl group, phenyl-α-methylpropyl group, phenyl-β-methylpropyl group, phenylbutyl group, and phenylpentyl group.
上記アルキルスルホン酸基としては、炭素数1〜6個のアルキルスルホン酸基が好ましい。具体例としては、メチルスルホン酸基、エチルスルホン酸基、プロピルスルホン酸基等が挙げられる。 As said alkylsulfonic acid group, a C1-C6 alkylsulfonic acid group is preferable. Specific examples include a methyl sulfonic acid group, an ethyl sulfonic acid group, and a propyl sulfonic acid group.
スクアリリウム化合物イオンの具体例(化学式(1)〜(24))を以下に示す。 Specific examples of the squarylium compound ions (chemical formulas (1) to (24)) are shown below.
本発明のスクアリリウム化合物の極大吸収波長は、380〜450nmであるので、3原色のうち、イエロー色として使用されるのが好ましく挙げられる。 Since the maximum absorption wavelength of the squarylium compound of the present invention is 380 to 450 nm, it is preferably used as a yellow color among the three primary colors.
本発明の着色組成物は、一般式(A)〜(D)で表されるスクアリリウム化合物イオンと、水素イオン又は遷移金属イオンとからなるスクアリリウム化合物を含有する着色色素、有機溶媒、シリカ粒子、バインダー成分、添加剤等を含有してもよい。 The colored composition of the present invention includes a colored dye, an organic solvent, silica particles, and a binder containing a squarylium compound ion composed of a squarylium compound ion represented by general formulas (A) to (D) and a hydrogen ion or a transition metal ion. You may contain a component, an additive, etc.
バインダー成分としては、アクリル樹脂又はポリエステル樹脂が挙げられる。 Examples of the binder component include an acrylic resin or a polyester resin.
アクリル樹脂としては、アクリル酸、アクリル酸メチル、アクリル酸エチル、n−ブチルアクリル酸、2−エチルアクリル酸、2−ヒドロキシエチルアクリル酸、メタアクリル酸、メタアクリル酸メチル、メタアクリル酸エチル、スチレン、マレイン酸又はフタル酸等からなるアクリルポリマーが挙げられる。
アクリル樹脂の平均分子量としては、1000〜100000が好ましく1000〜10000がより好ましく挙げられる。
As acrylic resin, acrylic acid, methyl acrylate, ethyl acrylate, n-butyl acrylic acid, 2-ethyl acrylic acid, 2-hydroxyethyl acrylic acid, methacrylic acid, methyl methacrylate, ethyl methacrylate, styrene An acrylic polymer composed of maleic acid or phthalic acid.
The average molecular weight of the acrylic resin is preferably 1000 to 100,000, and more preferably 1000 to 10,000.
ポリエステル樹脂としては、重合ポリエステル、ポリエステルアミド酸、ポリエステルをベースとするアクリルグラフトポリエステル、ポリエステルウレタン等が挙げられる。
ポリエステル樹脂の平均分子量としては、1000〜100000が好ましく1000〜10000がより好ましく挙げられる。
Examples of the polyester resin include polymerized polyester, polyester amide acid, polyester-based acrylic graft polyester, and polyester urethane.
The average molecular weight of the polyester resin is preferably from 1,000 to 100,000, more preferably from 1,000 to 10,000.
着色組成物におけるバインダー成分の含有量は、1〜50質量%が好ましく、5〜45質量%がより好ましく、10〜40質量%が特に好ましく挙げられる。 1-50 mass% is preferable, as for content of the binder component in a coloring composition, 5-45 mass% is more preferable, and 10-40 mass% is mentioned especially preferably.
シリカ粒子としては、沈降性シリカ、ヒュームドシリカ、コロイダルシリカ等が挙げられる。これらは、いずれも表面にシラノール基が存在するので、親水性を有している。
シリカ粒子は、用いる着色色素によって有機溶媒が異なるため、使用する有機溶媒に合わせて、着色組成物中におけるシリカ粒子の分散状態が良好になるように調整する必要がある。
また、シリカ粒子は、表面のシラノール基の少なくとも一部を疎水化して調整することが好ましい。シリカ粒子表面を疎水化させる方法としては、シリカとジシロキサン化合物、アルキルアルコキシシラン化合物、有機ハロゲン化ケイ素化合物等のシリル化剤を反応させることにより、シリカ粒子の表面のシラノール基をアルキルシリル基等の疎水基により修飾する方法が挙げられる。
Examples of the silica particles include precipitated silica, fumed silica, colloidal silica, and the like. All of these have hydrophilicity because silanol groups exist on the surface.
Since silica particles have different organic solvents depending on the coloring pigments to be used, it is necessary to adjust the dispersion state of the silica particles in the coloring composition in accordance with the organic solvent to be used.
The silica particles are preferably prepared by hydrophobizing at least a part of the silanol groups on the surface. As a method of hydrophobizing the surface of silica particles, the silanol groups on the surface of silica particles can be converted to alkylsilyl groups by reacting silica with a silylating agent such as a disiloxane compound, an alkylalkoxysilane compound, or an organic silicon halide compound. And a method of modifying with a hydrophobic group.
シリカ粒子の平均粒径は、好ましくは1〜50nmであり、より好ましくは3〜40nmであり、特に好ましくは3〜30nmである。 The average particle diameter of the silica particles is preferably 1 to 50 nm, more preferably 3 to 40 nm, and particularly preferably 3 to 30 nm.
着色組成物におけるシリカ粒子の配合量は、0.01〜5.0質量%が好ましく、0.01〜3.0質量%がより好ましく挙げられる。 0.01-5.0 mass% is preferable and, as for the compounding quantity of the silica particle in a coloring composition, 0.01-3.0 mass% is mentioned more preferably.
有機溶媒としては、使用するバインダー成分を溶解するものを用いるのが好ましく、例えば、N−メチル−2−ピロリドン、N,N−ジメチルアセトアミド、N,N−ジメチルホルムアミド等のアミド系極性溶媒、β−プロプオラクトン、γ−ブチロラクトン、γ−バレロラクトン、δ−バレロラクトン、γ−カプロラクトン等のラクトン類、メチルセロソルブ、エチルセロソルブ、メチルカルビトール、エチルカルビトール、プロピレングリコール、モノエチレングリコール等のエチレングリコール又はプロピレングリコール誘導体、アセト酢酸エチル、メチル−3−メトキシプロピオネート、3−メチル−3−メトキシブタノール等の脂肪族エステル、エタノール、シクロペンタノン、シクロヘキサノン等が挙げられる。
有機溶媒は単独でもよく、2種類以上混合して用いてもよい。
As the organic solvent, those that dissolve the binder component to be used are preferably used. For example, amide polar solvents such as N-methyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethylformamide, β -Lactones such as propolactone, γ-butyrolactone, γ-valerolactone, δ-valerolactone, γ-caprolactone, ethylene such as methyl cellosolve, ethyl cellosolve, methyl carbitol, ethyl carbitol, propylene glycol, monoethylene glycol Examples include glycol or propylene glycol derivatives, aliphatic esters such as ethyl acetoacetate, methyl-3-methoxypropionate, and 3-methyl-3-methoxybutanol, ethanol, cyclopentanone, and cyclohexanone.
An organic solvent may be individual and may be used in mixture of 2 or more types.
有機溶媒の総量は、60〜95質量%が好ましく、65〜95質量%がより好ましく、70〜95質量%が特に好ましく挙げられる。 The total amount of the organic solvent is preferably 60 to 95% by mass, more preferably 65 to 95% by mass, and particularly preferably 70 to 95% by mass.
添加剤としては、界面活性剤、酸化防止剤、光安定剤、加工安定剤が挙げられる。
界面活性剤としては、シリコン系界面活性剤、アクリル系界面活性剤、フッ素系界面活性剤等を用いることができる。酸化防止剤としては、ヒンダードフェノール系化合物等を用いることができる。光安定剤としては、ヒンダードアミン系化合物、ジイモニウム系化合物、アミニウム系化合物を用いることができる。加工安定剤としては、リン系化合物を用いることができる。
Examples of the additive include a surfactant, an antioxidant, a light stabilizer, and a processing stabilizer.
As the surfactant, a silicon surfactant, an acrylic surfactant, a fluorine surfactant, or the like can be used. As the antioxidant, a hindered phenol compound or the like can be used. As the light stabilizer, hindered amine compounds, diimonium compounds, and aminium compounds can be used. A phosphorus compound can be used as the processing stabilizer.
<カラーフィルター>
本発明のカラーフィルターについて説明する。
<Color filter>
The color filter of the present invention will be described.
本発明のカラーフィルターは、前記着色組成物を用い、着色組成物を基材上に塗布して作製することができる。
着色組成物を基板上に塗布する方法としては、スピンコーター、バーコーター、ブレードコーター、ロールコーター、ダイコーター、インクジェット印刷法、スクリーン印刷法等で基板に塗布する方法、基板を溶媒中に浸漬する方法、溶液を基板に噴霧する方法を用いることができる。基板としては、ソーダガラス、無アルカリガラス、ホウケイ酸ガラス、石英ガラス等の透明基板等が用いられる。
The color filter of the present invention can be produced by using the colored composition and applying the colored composition onto a substrate.
As a method of applying the coloring composition on the substrate, a method of applying to the substrate by a spin coater, a bar coater, a blade coater, a roll coater, a die coater, an ink jet printing method, a screen printing method, or the like, or immersing the substrate in a solvent The method and the method of spraying a solution on a substrate can be used. As the substrate, a transparent substrate such as soda glass, alkali-free glass, borosilicate glass, or quartz glass is used.
本発明の着色組成物を上記方法で透明基板上に塗布した後、乾燥させて、着色組成物の塗膜を作製する。加熱乾燥の場合、オーブン、ホットプレート等を使用し、50〜180℃の範囲で1分〜3時間行うのが好ましい。 After apply | coating the coloring composition of this invention on a transparent substrate by the said method, it is made to dry and the coating film of a coloring composition is produced. In the case of heat drying, it is preferable to use an oven, a hot plate, etc., and perform it in the range of 50-180 degreeC for 1 minute-3 hours.
ブッラクマトリックスを設けた基体表面へ着色組成物を塗布させて、熱により硬化又は光により重合させた後に熱により硬化させることで得ることもできる。 It can also be obtained by applying a coloring composition to the surface of a substrate provided with a black matrix, curing by heat or polymerizing by light and then curing by heat.
また、カラーフィルターの製造方法としては、フォトレジストによりパターンを形成し、次に染色する方法と、着色剤を添加したフォトレジストによりパターンを形成する方法がある。本発明のスクアリリウム化合物を用いる場合は、いずれの場合でも製造できるが、好ましくは、熱硬化性樹脂、キノンジアジド化合物、架橋剤、着色化合物、有機溶媒を含有してなるポジ型レジスト組成物を基体上に塗布後、マスクを通して露光し、露光後のポジ型レジストパターンを形成させ、上記ポジ型レジストパターンを全面露光し、露光後のポジ型レジストパターンを硬化させてカラーフィルターを製造することができる。 In addition, as a method for producing a color filter, there are a method of forming a pattern with a photoresist and then dyeing the pattern, and a method of forming a pattern with a photoresist added with a colorant. When the squarylium compound of the present invention is used, it can be produced in any case. Preferably, a positive resist composition containing a thermosetting resin, a quinonediazide compound, a crosslinking agent, a coloring compound, and an organic solvent is formed on the substrate. After the coating, the film is exposed through a mask to form an exposed positive resist pattern, the entire surface of the positive resist pattern is exposed, and the exposed positive resist pattern is cured to produce a color filter.
ブラックマトリックスを形成させ、RGB原色系あるいは、Y.M.C補色系カラーフィルターを得ることができる。ブラックマトリックスは、樹脂中にカーボンブラック、チタンブラック等の遮光材を分散させた樹脂ブラックマトリックスを用いるのが好ましく挙げられる。 A black matrix is formed and an RGB primary color system or Y.I. M.M. A C-complementary color filter can be obtained. The black matrix is preferably a resin black matrix in which a light shielding material such as carbon black or titanium black is dispersed in the resin.
本発明のカラーフィルター用着色組成物を用いて作製したカラーフィルターは、耐熱性が高い特徴を有している。 The color filter produced using the coloring composition for a color filter of the present invention has a high heat resistance.
以下、本発明を実施例に基づいてより詳細に説明する。なお、本発明は本実施例によりなんら限定されない。実施例中の「%」は「質量%」を表す。 Hereinafter, the present invention will be described in more detail based on examples. In addition, this invention is not limited at all by this Example. “%” In the examples represents “% by mass”.
<スクアリリウム化合物の合成>
本実施例で用いたスクアリリウム化合物(化合物(a)〜(j))を表1にまとめた。
<Synthesis of squarylium compound>
The squarylium compounds (compounds (a) to (j)) used in this example are summarized in Table 1.
(スクアリリウム化合物(a)の製造)
冷却管を付けた三ッ口フラスコに3,4−ジクロロ−3−シクロブテン−1,2−ジオン5.0部と、N,N−ジブチルアニリン4.6部を入れ、そこに脱水トルエン80部を加え、24時間室温にて撹拌した。反応終了後、NaHCO3水溶液で洗浄、トルエンにより抽出し溶媒を減圧留去した。得られた固体を減圧ろ過にて濾取し、ヘキサン洗浄後、減圧乾燥して3−クロロ−4−〔4−(N,N−ジブチルアミノ)フェニル〕3−シクロブテン−1,2−ジオン5.5部を得た。
(Production of squarylium compound (a))
In a three-necked flask equipped with a condenser tube, 5.0 parts of 3,4-dichloro-3-cyclobutene-1,2-dione and 4.6 parts of N, N-dibutylaniline are placed, and 80 parts of dehydrated toluene are added thereto. And stirred at room temperature for 24 hours. After completion of the reaction, the mixture was washed with an aqueous NaHCO 3 solution, extracted with toluene, and the solvent was distilled off under reduced pressure. The obtained solid was collected by filtration under reduced pressure, washed with hexane, and dried under reduced pressure to give 3-chloro-4- [4- (N, N-dibutylamino) phenyl] 3-cyclobutene-1,2-dione 5 .5 parts were obtained.
冷却管を付けた三ッ口フラスコに、3−クロロ−4−〔4−(N,N−ジブチルアミノ)フェニル〕3−シクロブテン−1,2−ジオン5.5部と酢酸:水=4:1混合溶液50部を入れ、100℃にて5時間加熱撹拌した。反応後、室温まで冷却し、析出した固体を減圧ろ過にて濾取した。水で洗浄後、減圧乾燥してスクアリリウム化合物(a)4.1部を得た。 In a three-necked flask equipped with a condenser, 5.5 parts of 3-chloro-4- [4- (N, N-dibutylamino) phenyl] 3-cyclobutene-1,2-dione and acetic acid: water = 4: 50 parts of 1 mixed solution was added and stirred with heating at 100 ° C. for 5 hours. After the reaction, the reaction mixture was cooled to room temperature, and the precipitated solid was collected by filtration under reduced pressure. After washing with water and drying under reduced pressure, 4.1 parts of squarylium compound (a) was obtained.
(スクアリリウム化合物(b)の製造)
スクアリリウム化合物(a)の製造方法において、N,N−ジブチルアニリンをN、N−ジメチル−1−ナフチルアミンに代えた以外は、スクアリリウム化合物(a)の製造方法と同様にしてスクアリリウム化合物(b)を得た。
(Production of squarylium compound (b))
The squarylium compound (b) was prepared in the same manner as the squarylium compound (a) except that N, N-dibutylaniline was replaced with N, N-dimethyl-1-naphthylamine in the method of producing the squarylium compound (a). Obtained.
(スクアリリウム化合物(c)の製造)
冷却管を付けた三ッ口フラスコに3,4−ジクロロ−3−シクロブテン−1,2−ジオン12.3部と、無水塩化アルミニウム10.9部を入れ、そこに無水クロロホルム100mlを入れ、窒素雰囲気下で室温攪拌した。そこに、無水クロロホルム20mlに溶解したアニソール10.0部を室温滴下した。滴下終了後、10時間加熱攪拌した。反応終了後、10℃以下に冷却した状態で水を100ml加えたのち、有機層を水で洗浄し、溶媒を減圧留去した。得られた固体を減圧ろ過にて濾取し、トルエン洗浄後、減圧乾燥して3−クロロ−4−(p−メトキシ−フェニル)−シクロブタ−3−エン−1,2−ジオン11.6部を得た。
冷却管を付けた三ッ口フラスコに、3−クロロ−4−(p−メトキシ−フェニル)−シクロブタ−3−エン−1,2−ジオン11.6部と酢酸:水=1:1混合溶液200部を入れ、100℃にて8時間加熱撹拌した。反応後、室温まで冷却し、溶媒を減圧除去し、析出した固体を減圧ろ過にて濾取した。水で洗浄後、減圧乾燥してスクアリリウム化合物(c)8.6部得た。
(Production of squarylium compound (c))
In a three-necked flask equipped with a condenser tube, 12.3 parts of 3,4-dichloro-3-cyclobutene-1,2-dione and 10.9 parts of anhydrous aluminum chloride are placed, and 100 ml of anhydrous chloroform is placed therein, and nitrogen is added. Stir at room temperature under atmosphere. Thereto, 10.0 parts of anisole dissolved in 20 ml of anhydrous chloroform was added dropwise at room temperature. After completion of dropping, the mixture was stirred with heating for 10 hours. After completion of the reaction, 100 ml of water was added in a state cooled to 10 ° C. or lower, the organic layer was washed with water, and the solvent was distilled off under reduced pressure. The resulting solid was collected by filtration under reduced pressure, washed with toluene, and dried under reduced pressure to give 11.6 parts of 3-chloro-4- (p-methoxy-phenyl) -cyclobut-3-ene-1,2-dione. Got.
In a three-necked flask equipped with a condenser, 11.6 parts of 3-chloro-4- (p-methoxy-phenyl) -cyclobut-3-ene-1,2-dione and acetic acid: water = 1: 1 mixed solution 200 parts were added and stirred with heating at 100 ° C. for 8 hours. After the reaction, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the precipitated solid was collected by filtration under reduced pressure. After washing with water and drying under reduced pressure, 8.6 parts of squarylium compound (c) was obtained.
(スクアリリウム化合物(d)の製造)
三ッ口フラスコに3,4−ジメトキシ−3−シクロブテン−1,2−ジオン6.2部と、3−メチル−1−(3−プロピル)−5−ピラゾロン(ランカスター社製)7.6部を入れ、そこにメタノール500mlを入れて室温攪拌した。そこに、無水炭酸カリウム5.9部を加えて5時間室温攪拌した。反応終了後、固体をろ過し、メタノールで洗浄した。得られた固体に水200mlと炭酸カリウム2.7部を加えて、50℃にて2時間加熱攪拌した。反応終了後、1M塩酸500ml中に注ぎ入れ析出した固体をろ過した。水で洗浄した後、減圧乾燥してスクアリリウム化合物(d)4.3部を得た。
(Production of squarylium compound (d))
In a three-necked flask, 6.2 parts of 3,4-dimethoxy-3-cyclobutene-1,2-dione and 7.6 parts of 3-methyl-1- (3-propyl) -5-pyrazolone (manufactured by Lancaster) Then, 500 ml of methanol was added thereto and stirred at room temperature. Thereto, 5.9 parts of anhydrous potassium carbonate was added and stirred at room temperature for 5 hours. After completion of the reaction, the solid was filtered and washed with methanol. To the obtained solid, 200 ml of water and 2.7 parts of potassium carbonate were added, and the mixture was heated and stirred at 50 ° C. for 2 hours. After completion of the reaction, the solution was poured into 500 ml of 1M hydrochloric acid and the precipitated solid was filtered. After washing with water, it was dried under reduced pressure to obtain 4.3 parts of squarylium compound (d).
(スクアリリウム化合物(e)の製造)
スクアリリウム化合物(d)の製造方法において、N−エチル−2−メチルチアゾリウムアイオダイドに代えた以外は、スクアリリウム化合物(d)の製造方法と同様にしてスクアリリウム化合物(e)を得た。
(Production of squarylium compound (e))
The squarylium compound (e) was obtained in the same manner as the squarylium compound (d) except that the method for producing the squarylium compound (d) was replaced with N-ethyl-2-methylthiazolium iodide.
(スクアリリウム化合物(f)の製造)
スクアリリウム化合物(a)4.1部と酢酸ニッケル・4水和物4.0部を、冷却管を付けた三ッ口フラスコに入れ、そこにTHF100部を加え、60℃にて4時間加熱撹拌した。反応後、室温まで冷却し、析出した固体を減圧ろ過にて濾取した。水で洗浄後、減圧乾燥して3−ヒドロキシ−4−〔4−(N-ジブチルアミノ)フェニル〕3−シクロブテン−1,2−ジオン−ニッケル錯体(スクアリリウム化合物(f))8.3部を得た。
(Production of squarylium compound (f))
Put 4.1 parts of squarylium compound (a) and 4.0 parts of nickel acetate tetrahydrate in a three-necked flask equipped with a condenser, add 100 parts of THF, and heat and stir at 60 ° C. for 4 hours. did. After the reaction, the reaction mixture was cooled to room temperature, and the precipitated solid was collected by filtration under reduced pressure. After washing with water and drying under reduced pressure, 8.3 parts of 3-hydroxy-4- [4- (N-dibutylamino) phenyl] 3-cyclobutene-1,2-dione-nickel complex (squarylium compound (f)) was added. Obtained.
(スクアリリウム化合物(g)の製造)
スクアリリウム化合物(a)を(b)に代えた以外は、スクアリリウム化合物(f)と同様の方法によってスクアリリウム化合物(g)を得た。
(Production of squarylium compound (g))
A squarylium compound (g) was obtained by the same method as the squarylium compound (f) except that the squarylium compound (a) was replaced with (b).
(スクアリリウム化合物(h)の製造)
スクアリリウム化合物(a)を(c)に代えた以外は、スクアリリウム化合物(f)と同様の方法によってスクアリリウム化合物(h)を得た。
(Production of squarylium compound (h))
The squarylium compound (h) was obtained by the same method as the squarylium compound (f) except that the squarylium compound (a) was replaced with (c).
(スクアリリウム化合物(i)の製造)
スクアリリウム化合物(a)を(d)に代えた以外は、スクアリリウム化合物(f)と同様の方法によってスクアリリウム化合物(i)を得た。
(Production of squarylium compound (i))
The squarylium compound (i) was obtained by the same method as the squarylium compound (f) except that the squarylium compound (a) was replaced by (d).
(スクアリリウム化合物(j)の製造)
スクアリリウム化合物(a)を(e)に代えた以外は、スクアリリウム化合物(f)と同様の方法によってスクアリリウム化合物(j)を得た。
(Production of squarylium compound (j))
A squarylium compound (j) was obtained by the same method as the squarylium compound (f) except that the squarylium compound (a) was replaced by (e).
実施例1〜10は着色色素としてスクアリリウム(a)〜(j)を用い、比較例1、2は着色色素としてPY138(ビーエーエスエフ社製「パリオトールイエロー」D0960)、PY185(ビーエーエスエフ社製「パリオトールイエロー」D1155)を用いた。 Examples 1 to 10 use squarylium (a) to (j) as coloring dyes, and Comparative Examples 1 and 2 use PY138 (“Pariotor Yellow” D0960 manufactured by BASF) and PY185 (manufactured by BASF Corporation) as coloring dyes. Paliotor Yellow "D1155) was used.
(実施例1)
(着色組成物の調整)
スクアリリウム化合物(a)10部、味の素ファインテクノ(株)製カチオン性ポリマーPB−814(固形分40%)12.5部、プロピレングリコールモノメチルエーテルアセテート41.2部、オルガノシリカゲル5部を撹拌し、均一に混合させて着色組成物を得た。
(カラーフィルターの作製)
得られた着色組成物をガラス基板上にスピンコートした後、有機溶媒を蒸発させた。次いで、マスクを通してガラス基板を露光した。その後100℃で加熱し、次いでアルカリ現像により露光部を除去して0.8μmの解像度を有するポジ型着色パターンを得た。これを全面露光後、150℃、15分過熱してカラーフィルターを得た。
Example 1
(Adjustment of coloring composition)
10 parts of squarylium compound (a), 12.5 parts of cationic polymer PB-814 (solid content 40%) manufactured by Ajinomoto Fine Techno Co., 41.2 parts of propylene glycol monomethyl ether acetate, 5 parts of organosilica gel are stirred. A colored composition was obtained by mixing uniformly.
(Production of color filter)
The obtained colored composition was spin-coated on a glass substrate, and then the organic solvent was evaporated. The glass substrate was then exposed through a mask. Thereafter, heating was performed at 100 ° C., and then the exposed portion was removed by alkali development to obtain a positive colored pattern having a resolution of 0.8 μm. After the entire surface was exposed, it was heated at 150 ° C. for 15 minutes to obtain a color filter.
(実施例2〜10、比較例1、2)
実施例2〜10、比較例1、2は、実施例1と同様にして、スクアリリウム(a)の代わりに表2に対応する着色色素を用いてカラーフィルターを製造した。
(Examples 2 to 10, Comparative Examples 1 and 2)
In Examples 2 to 10 and Comparative Examples 1 and 2, in the same manner as in Example 1, color filters corresponding to Table 2 were used instead of squarylium (a) to produce color filters.
(着色組成物の粘度とカラーフィルターの分光の測定の評価方法)
着色組成物の粘度とカラーフィルターの分光の極大ピークを測定し、表2に示す。
(Evaluation method for measuring viscosity of color composition and spectrum of color filter)
Table 2 shows the viscosity of the coloring composition and the spectral maximum peak of the color filter.
(カラーフィルターの耐熱性の評価方法)
カラーフィルターを250℃1時間加熱した後、膜厚及び色純度に対する残膜及び色差で評価した。残膜率が97%以上ある場合を○、97%未満の場合を×とした。色差が1未満の場合を○、1上の場合を×とした。測定結果を表2に示す。
(Evaluation method of heat resistance of color filter)
The color filter was heated at 250 ° C. for 1 hour, and then evaluated by the residual film and color difference with respect to the film thickness and color purity. The case where the remaining film ratio was 97% or more was rated as ○, and the case where it was less than 97% was rated as ×. The case where the color difference was less than 1 was marked with ◯, and the case where the color difference was above was marked with ×. The measurement results are shown in Table 2.
表3より、実施例1〜10は、粘度が低く、耐熱性に優れていることがわかった。 From Table 3, it was found that Examples 1 to 10 had low viscosity and excellent heat resistance.
本発明のスクアリリウム化合物を用いた着色組成物は、黄色を有するので、カラーフィルター用途以外にも、塗料、プラスチック、印刷インク、ゴム、レーザー、電子写真トナー、ジェットインキ、熱転写インキ等に適用できる。 Since the colored composition using the squarylium compound of the present invention has a yellow color, it can be applied to paints, plastics, printing inks, rubbers, lasers, electrophotographic toners, jet inks, thermal transfer inks and the like in addition to color filter applications.
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US8900780B2 (en) | 2011-12-26 | 2014-12-02 | Cheil Industries Inc. | Photosensitive resin composition for color filter and color filter using the same |
CN104513510A (en) * | 2013-09-26 | 2015-04-15 | 住友化学株式会社 | Coloring and solidifying resin composition |
JP2019011455A (en) * | 2016-12-27 | 2019-01-24 | 東洋インキScホールディングス株式会社 | Squarylium compound and use thereof |
JP2019157086A (en) * | 2018-03-16 | 2019-09-19 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Compound |
JP2019157087A (en) * | 2018-03-16 | 2019-09-19 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Compound |
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2010
- 2010-04-02 JP JP2010085872A patent/JP5495903B2/en active Active
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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US8900780B2 (en) | 2011-12-26 | 2014-12-02 | Cheil Industries Inc. | Photosensitive resin composition for color filter and color filter using the same |
CN104513510A (en) * | 2013-09-26 | 2015-04-15 | 住友化学株式会社 | Coloring and solidifying resin composition |
JP2019011455A (en) * | 2016-12-27 | 2019-01-24 | 東洋インキScホールディングス株式会社 | Squarylium compound and use thereof |
JP2019157086A (en) * | 2018-03-16 | 2019-09-19 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Compound |
JP2019157087A (en) * | 2018-03-16 | 2019-09-19 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Compound |
JP7053322B2 (en) | 2018-03-16 | 2022-04-12 | 東友ファインケム株式会社 | Compound |
JP7053321B2 (en) | 2018-03-16 | 2022-04-12 | 東友ファインケム株式会社 | Compound |
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