WO2008056819A1 - Color filter, and liquid crystal display device and ccd device each using the color filter - Google Patents
Color filter, and liquid crystal display device and ccd device each using the color filter Download PDFInfo
- Publication number
- WO2008056819A1 WO2008056819A1 PCT/JP2007/072059 JP2007072059W WO2008056819A1 WO 2008056819 A1 WO2008056819 A1 WO 2008056819A1 JP 2007072059 W JP2007072059 W JP 2007072059W WO 2008056819 A1 WO2008056819 A1 WO 2008056819A1
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- pigment
- group
- color filter
- solvent
- compound
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- 230000009977 dual effect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- IAJNXBNRYMEYAZ-UHFFFAOYSA-N ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC)C1=CC=CC=C1 IAJNXBNRYMEYAZ-UHFFFAOYSA-N 0.000 description 1
- WNIHNYUROPJCLW-UHFFFAOYSA-N ethyl 2-ethoxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OCC WNIHNYUROPJCLW-UHFFFAOYSA-N 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- JLEKJZUYWFJPMB-UHFFFAOYSA-N ethyl 2-methoxyacetate Chemical compound CCOC(=O)COC JLEKJZUYWFJPMB-UHFFFAOYSA-N 0.000 description 1
- WHRLOJCOIKOQGL-UHFFFAOYSA-N ethyl 2-methoxypropanoate Chemical compound CCOC(=O)C(C)OC WHRLOJCOIKOQGL-UHFFFAOYSA-N 0.000 description 1
- FJAKCEHATXBFJT-UHFFFAOYSA-N ethyl 2-oxobutanoate Chemical compound CCOC(=O)C(=O)CC FJAKCEHATXBFJT-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-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
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- DVFRXGSDHNXWDP-UHFFFAOYSA-N hexanoic acid;2-(2-hydroxypropoxy)propan-1-ol Chemical compound CCCCCC(O)=O.CC(O)COC(C)CO DVFRXGSDHNXWDP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000012510 hollow fiber Substances 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical class C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- XVTQAXXMUNXFMU-UHFFFAOYSA-N methyl 2-(3-oxo-2-pyridin-2-yl-1h-pyrazol-5-yl)acetate Chemical compound N1C(CC(=O)OC)=CC(=O)N1C1=CC=CC=N1 XVTQAXXMUNXFMU-UHFFFAOYSA-N 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- AKWHOGIYEOZALP-UHFFFAOYSA-N methyl 2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC AKWHOGIYEOZALP-UHFFFAOYSA-N 0.000 description 1
- XPIWVCAMONZQCP-UHFFFAOYSA-N methyl 2-oxobutanoate Chemical compound CCC(=O)C(=O)OC XPIWVCAMONZQCP-UHFFFAOYSA-N 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 1
- AWIZFKXFPHTRHN-UHFFFAOYSA-N naphtho[2,3-f]quinoline Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 AWIZFKXFPHTRHN-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229940099800 pigment red 48 Drugs 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000075 poly(4-vinylpyridine) Chemical class 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000005143 pyrolysis gas chromatography mass spectroscopy Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- LBMZLLXZMSMJPJ-UHFFFAOYSA-N thiepane 1-oxide Chemical compound O=S1CCCCCC1 LBMZLLXZMSMJPJ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005627 triarylcarbonium group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
-
- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/1462—Coatings
- H01L27/14621—Colour filter arrangements
Definitions
- the present invention relates to a color filter having a high contrast ratio and an excellent hue, and to a liquid crystal display device and a CCD device each using the color filter.
- LCD liquid crystal display
- CRT Braun tube
- Improvement in performances of the color filter is a key to responding to such the demand. This is because the color filter plays a role in coloring of display image of a LCD panel and the like, and therefore directly controls color properties of the LCD panel. As properties required for the color filter, high optical transmission, color purity, high contrast, lowered reflection, and the like can be mentioned. In particular, a low contrast causes a display screen to become dark owing to attenuation of light and causes discrimination between dark and bright to become unclear. Therefore, a high contrast property is desired. Besides, it is also desired that a reproduction range of color that is obtained by combining B, G, and R is wide, and purity of each of thus-obtained color is high. However, improvement of contrast of color filters sometimes results in decrease in color purity accompanied by a decrease of a color reproduction range.
- JP-A- 10- 130547 a dispersion in which a coloring matter is dispersed in an organic solvent
- the problem to be solved in the present invention is to provide a color filter that has a high contrast and an excellent chromaticity and also has suitability for a continuous production. Further, another problem to be solved in the present invention is to provide a liquid crystal display device and a CCD device each exhibits excellent image display performances, in which the above-described high quality color filter is used.
- a color filter having a layer colored in at least one prescribed hue and formed on a substrate which comprises: a water-insoluble organic pigment (a), a monomer or oligomer having a polymerizable group (b), and a water-soluble polymer (c), in the form of a pigment dispersion, in which the dispersion is solidified by polymerizing the monomer or oligomer so as to form said colored layer, wherein a content of the water-soluble polymer (c) in the colored layer is at least 0.1 mass % of the total solid content.
- the pigment dispersion comprises the organic pigment (a) in a form of fine particles, wherein the fine particles are deposited by mixing an organic pigment solution of the organic pigment (a) dissolved in a good solvent, together with a solvent that has compatibility with the good solvent and functions as a poor solvent for the organic pigment.
- a pigment dispersion which comprises a water-insoluble organic pigment (a) and a water- soluble polymer (b), wherein a water content of the pigment dispersion is 10 mass% or less, and wherein a content of the water-soluble polymer (b) is at least 0.1 mass% of the organic pigment (a).
- the color filter of the present invention has at least one colored layer formed on a substrate.
- a transparent substrate is preferred, and use can be made of glass plates such as a soda glass plate having a silicon oxide coating on a surface thereof, a low-expansion glass, and a silica glass plate.
- resin films such as polyethylene terephtharate, cellulose triacetate, polystyrene, and polycarbonate may be used.
- a method of forming the colored layer on the substrate there is no particular limitation, so long as it is an ordinary method used to prepare a color filter.
- a color filter may be obtained by coating such pigment dispersion as described later on a substrate, to form a colored photosensitive resin layer using an apparatus such as a spin coater, a slit coater, and a roll coater, followed by exposure and development.
- a colored layer is formed by initially forming the above-described colored photosensitive resin layer on a temporary support, and then transferring the colored photosensitive resin layer on a substrate using a laminator, followed by exposure and development; and/or a method in which a colored layer is formed by spraying drops of a pigment dispersion onto a substrate using a so-called inkjet system.
- the thickness of the colored layer is not particularly limited, but preferably in the range of from 0.5 ⁇ m to 5 ⁇ m, and more preferably in the range of from 1 ⁇ m to 3 ⁇ m.
- the area of the colored layer is not particularly limited.
- the area is preferably in the range of from 400 ⁇ m 2 to 90,000 ⁇ m 2 , and more preferably in the range of from 1,000 ⁇ m 2 to 15,000 ⁇ m 2 .
- the above-described colored layer in the color filter of the present invention is formed from a polymerized and solidified material that is obtained by polymerizing a pigment dispersion comprising a water-insoluble organic pigment (a), a monomer or oligomer having a polymerizable group (b), and a water-soluble polymer (c).
- the water-insoluble organic pigment there is no particular limitation, so long as the pigment is sparingly soluble in water. It is preferred that the pigment is dispersed in a dispersion in a form of fine pigment particles.
- a preferable method may be chosen from various methods such as a vapor phase method, a grinding method, a re-precipitation method, and a laser ablation method, according to the kind of pigment and/or purpose. It is preferred to use such a fine particle deposition method which will be described later, from the viewpoint of obtaining pigment particles that are fine in size and have a uniform particle size distribution and excellent dispersion stability.
- examples the water-insoluble organic pigment include perylene-, perynone-, quinacridone-, quinacridonequinone-, anthraquinone-, anthanthrone-, benzimidazolone-, condensed disazo-, disazo-, azo-, indanthrone-, p ' hthalocyanine-, triaryl carbonium-, dioxazine-, aminoanthraquinone-, diketopyrrolopyrrole-, thioindigo-, isoindoline-, isoindolinone-, pyranthrone-, or isoviolanthrone-compound pigment, or a mixture thereof.
- examples of the water-insoluble organic pigment include perylene-compound pigments, such as C.I. Pigment Red 190 (CI. No. 71140), C.I. Pigment Red 224 (CI. No. 71 127), C.I. Pigment Violet 29 (CI. No. 71 129), or the like; perynone-compound pigments, such as C.I. Pigment Orange 43 (CI. No. 71105), C.I. Pigment Red 194 (CI. No. 71 100) or the like; quinacridone-compound pigments, such as C.I. Pigment Violet 19 (CI. No. 73900), C.I. Pigment Violet 42, CI. Pigment Red 122 (CI. No.
- anthanthrone-compound pigments such as C.I. Pigment Red 168 (CI. No. 59300) or the like
- benzimidazolone-compound pigments such as C.I. Pigment Brown 25 (CI. No. 12510), CI. Pigment Violet 32 (CI. No. 12517), C.I. Pigment Yellow 180 (CI. No. 21290), C.I. Pigment Yellow 181 (CI. No. 11777), C.I. Pigment Orange 62 (CI. No. 11775), C.I. Pigment Red 185 (CI. No. 12516), or the like
- condensed disazo-compound pigments such as C.I. Pigment Yellow 93 (CI. No.
- C.I. Pigment Yellow 94 (CI. No. 20038), C.I. Pigment Yellow 95 (CI. No. 20034), C.I. Pigment Yellow 128 (CI. No. 20037), C.I. Pigment Yellow 166 (CI. No. 20035), C.I. Pigment Orange 34 (CI. No. 21115), C.I. Pigment Orange 13 (CI. No. 21110), C.I. Pigment Orange 31 (CI. No. 20050), C.I. Pigment Red 144 (CI. No. 20735), C.I. Pigment Red 166 (CI. No. 20730), C.I. Pigment Red 220 (CI. No. 20055), C.I. Pigment Red 221 (CI. No.
- C.I. Pigment Red 242 (CI. No. 20067), C.I. Pigment Red 248, C.I. Pigment Red 262, CI. Pigment Brown 23 (CI. No. 20060), or the like; disazo- compound pigments, such as C.I. Pigment Yellow 13 (CI. No. 21 100), C.I. Pigment Yellow 83 (CI. No. 21108), C.I. Pigment Yellow 188 (CI. No. 21094), or the like; azo-compound pigments, such as C.I.
- Pigment Red 187 (CI. No. 12486), CI. Pigment Red 170 (CI. No. 12475), C.I. Pigment Yellow 74 (CI. No. 1 1714), C.I. Pigment Yellow 150 (CI. No. 48545), C.I. Pigment Red 48 (CI. No. 15865), C.I. Pigment Red 53 (CI. No. 15585), C.I. Pigment Orange 64 (CI. No. 12760), CI. Pigment Red 247 (CI. No. 15915), or the like; indanthrone-compound pigments, such as CI. Pigment Blue 60 (CI. No. 69800), or the like; phthalocyanine-compound pigments, such as C.I.
- Pigment Green 7 (CI. No. 74260), C.I. Pigment Green 36 (CI. No. 74265), Pigment Green 37 (CI. No. 74255), Pigment Blue 16 (CI. No. 74100), C.I. Pigment Blue 75 (CI. No. 74160:2), C.I. Pigment Blue 15:6 (CI. No. 74160), C.I. Pigment Blue 15:3 (CI. No. 74160) or the like; triaryl carbonium-compound pigments, such as C.I. Pigment Blue 56 (CI. No. 42800), C.I. Pigment Blue 61 (CI. No. 42765: 1), or the like; dioxazine-compound pigments, such as C.I.
- Pigment Violet 23 (CI. No. 51319), C.I. Pigment Violet 37 (CI. No. 51345), or the like; aminoanthraquinone-compound pigments, such as C.I. Pigment Red 177 (CI. No. 65300), or the like; diketopyrrolopyrrole-compound pigments, such as C.I. Pigment Red 254 (CI. No. 561 10), C.I. Pigment Red 255 (CI. No. 561050), C.I. Pigment Red 264, C.I. Pigment Red 272 (CI. No. 561 150), C.I. Pigment Orange 71, C.I.
- Pigment Orange 73 or the like
- thioindigo-compound pigments such as C.I. Pigment Red 88 (CI. No. 73312), or the like
- isoindoline-compound pigments such as C.I. Pigment Yellow 139 (CI. No. 56298), CI. Pigment Orange 66 (CI. No. 48210), or the like
- isoindolinone-compound pigments such as C.I. Pigment Yellow 109 (CI. No. 56284), C.I. Pigment Yellow 185 (CI. No. 56290), C.I. Pigment Orange 61 (CI. No. 1 1295), or the like
- pyranthrone-compound pigments such as C.I.
- Pigment Orange 40 (CI. No. 59700), C.I. Pigment Red 216 (CI. No. 59710), or the like; quinophthalone-compound pigments, such as C.I. Pigment Yellow 138; or isoviolanthrone-compound pigments, such as C.I. Pigment Violet 31 (CI. No. 60010), or the like.
- two or more kinds of the organic pigment or solid solution thereof may be used in combination. Besides, they may be used together with ordinary dyes.
- the content of the organic pigment is preferably in the range of from 10 mass% to 70 mass%, more preferably from 30 mass% to 60 mass%, based on the total solid content in the colored layer.
- the monomer or oligomer having a polymerizable group used in the color filter of the present invention is preferably a monomer or oligomer which has two or more ethylenically unsaturated double bonds and which undergoes addition-polymerization by irradiation with light.
- the monomer or oligomer may be a compound having at least one addition-polymerizable ethylenically unsaturated group therein and having a boiling point of 100 0 C or higher at normal pressure.
- Examples thereof include: a monofunctional acrylate and a monofunctional methacrylate such as dipentaerythritol hexa(meth)acrylate, polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, and phenoxyethyl(meth)acrylate; polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolethane triacrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane diacrylate, neopentyl glycol di(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, hexanediol di(meth)acrylate
- Another preferred examples include those compounds that are obtained by addition reaction of ethylene oxide or propylene oxide to polyfunctional alcohol, followed by (meth)acrylation, as described in formulae (1) and (2) of JP-A- 10-62986.
- (meth)acrylate is used to mean both “acrylate” and “methacrylate”.
- Examples of the monomer and oligomer having a polymerizable group further include urethane acrylates as described in JP-B-48-41708 ("JP-B" means examined Japanese patent publication), JP-B-50- 6034, and JP-A-51 -37193 ; and polyester acrylates as described in JP-A 48-64183, JP-B-49-43191 , and JP- B-52-30490; polyfunctional acrylates or polyfunctional methacrylates such as an epoxy acrylate which is a reaction product of an epoxy resin and (meth)acrylic acid.
- JP-B means examined Japanese patent publication
- JP-B-50- 6034 JP-A-51 -37193
- polyester acrylates as described in JP-A 48-64183, JP-B-49-43191 , and JP- B-52-30490
- polyfunctional acrylates or polyfunctional methacrylates such as an epoxy acrylate which is a reaction product of an epoxy resin and (me
- trimethylolpropane tri(meth)acrylate pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and dipentaerythritol penta(meth)acrylate are preferable.
- polymerizable compound B described in JP-A-1 1-133600 can be mentioned as a preferable example.
- These monomers or oligomers having a polymerizable group preferably have a molecular weight of 200 to 1000, and they may be used singly or as a mixture of two or more kinds thereof.
- the content of the monomer or oligomer having a polymerizable group is not particularly limited, but the content thereof is generally in a range of from 5 mass% to 50 mass%, preferably from 10 mass% to 40 mass%, in terms of the polymer in the colored layer, based on the total solid content in the colored layer. If this content is too large, control of development properties becomes difficult, raising problems of production suitability. If the content is too small, a curing force at the time of exposure becomes insufficient. [0018]
- the colored layer contains a water-soluble polymer.
- the water-soluble polymer preferably has solubility to pure water (25 °C) of 10 or more, more preferably 50 or more, and especially preferably 100 or more.
- polymers that are neutral in the state of aqueous solution which means that the polymers scarcely affect to the color filter.
- a water-soluble compound whose 50 mass% aqueous solution shows pH of from 5 to 9, more preferably from 6 to 8.
- synthetic polymer compounds such as polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, polyethylene glycol, and polyethylene oxide, and copolymers of these compounds. Of these polymer compounds, polyvinyl pyrrolidone is especially preferred.
- These water-soluble polymers may be used singly or in combination of two or more kinds of polymers.
- the molecular weight of the water-soluble polymer is not particularly limited, but a number- average molecular weight (Mn) thereof is preferably from 1,000 to 2,000,000, more preferably from 5,000 to 1,000,000, furthermore preferably from 10,000 to 500,000, and especially preferably from 10,000 to 100,000. [0020]
- the content of the water-soluble polymer in the colored layer is 0.1 mass% or more, preferably 0.5 mass% or more, and more preferably 1 mass% or more, based on the total solid content in the colored layer.
- the content of the water-soluble polymer in the colored layer is 5 mass% or less, based on the total solid content of the colored layer.
- binders having an acidic group are preferred.
- the binder may be added at the time of preparation of inkjet ink or colored photosensitive resin composition. It is also preferred to add the binder at the time of preparation of pigment dispersion, or prior to the preparation thereof, or alternatively at the time of formation of pigment fine particles as described later.
- the binder may be added to both or either of the organic pigment solution and the poor solvent used at the time of depositing pigment fine particles by adding thereto the organic pigment solution. Alternatively, it is also preferred to add a binder solution separately at the time of formation of pigment fine particles.
- the binder is preferably an alkali-soluble polymer having a polar group such as a carboxylic acid group or a carboxylate group at its side chain.
- a polar group such as a carboxylic acid group or a carboxylate group at its side chain.
- examples thereof include a methacrylic acid copolymer, an acrylic acid copolymer, an itaconic acid copolymer, a crotonic acid copolymer, a maleic acid copolymer, and a partially esterified maleic acid copolymer described in, for example, JP-A-59-44615, JP-B-54-34327, JP-B-58-12577, JP-B-54-25957, JP-A-59-53836, and JP-A-59-71048.
- the examples further include a cellulose derivative having a carboxylic acid group or a carboxylate group at its side chain.
- a product obtained by adding a cyclic acid anhydride to a polymer having a hydroxyl group can also be preferably used.
- particularly preferable examples of the binder include a copolymer of benzyl (meth)acrylate and (meth)acrylic acid and a multi-component copolymer of benzyl (meth)acrylate, (meth)acrylic acid, and any other monomer, described in U.S. Patent No. 4,139,391.
- Each of these binder polymers having a polar group may be used singly, or may be used in combination with an ordinary film formable polymer so that they are used in a state of a composition.
- alkali-soluble polymer herein means a polymer whose acid strength is in the pH range of 1 or more but less than 5 when the pH of an aqueous solution containing 50 mass% of the polymer dissolved therein is measured. Based on the acid strength, the alkali-soluble polymer is distinguished from the above-described neutral water-soluble polymer.
- a polymerizable group may be included in the side chain, and ultraviolet curing resins and thermosetting resins are also useful.
- examples of the polymers containing polymerizable groups are given below, but not limited to these, provided that an alkali soluble group, such as -COOH group, -OH group, and an ammonium group, and a carbon-carbon unsaturated bond, are included therein.
- a compound having an acryloyl group, and an acid anhydride, and an isocyanate group, in place of the epoxy ring can be used.
- a reaction product which is obtained by reacting a saturated- or unsaturated- polybasic acid anhydride with a compound obtained by reacting a compound having an epoxy ring with an unsaturated carboxylic acid, such as acrylic acid, as disclosed in JP-A-6- 102669 and JP-A-6-1938 can also be used.
- Examples of the compound which has both an alkali-soluble group, such as a -COOH group, and a carbon-carbon unsaturated group include DIANAL NR series (trade name, manufactured by Mitsubishi Rayon Co., Ltd.), PHOTOMER 6173 (trade name; -COOH group-containing polyurethane acrylic oligomer, manufactured by Diamond Shamrock Co, Ltd.), VISCOAT R-264 and KS RESIST 106 (both trade names; manufactured by Osaka Organic Chemical Industry Ltd.), CYCLOMER P series and PRAXEL CF200 series (both trade names, manufactured by Daicel Chemical Industries, Ltd.), EBECRYL 3800 (trade name, manufactured by Daicel-UCB Company Ltd.), and the like.
- DIANAL NR series trade name, manufactured by Mitsubishi Rayon Co., Ltd.
- PHOTOMER 6173 trade name; -COOH group-containing polyurethane acrylic oligomer, manufactured by Diamond Shamrock Co, Ltd.
- the binder resin organic macromolecule polymers having a water-soluble atomic group at a part of side chains of the polymer can be used. It is preferable that the binder resin is a linear organic macromolecule polymer miscible with a monomer and is soluble in an organic solvent and an alkaline solution (preferably one developable with a weak alkaline aqueous solution).
- Examples of such an alkali-soluble resin include polymers which have a carboxylic acid in a side chain, such as the methacrylic acid copolymer, the acrylic acid copolymer, the itaconic acid copolymer, the crotonic acid copolymer, the maleic acid copolymer, the partially esterified maleic acid copolymer, and the like as disclosed in, for example, JP-A-59-44615, JP-A-54-34327, JP-A-58-12577, JP-A-54-25957, JP-A-59- 53836, and JP-A-59-71048.
- acidic cellulose derivatives which have a carboxylic acid in a side chain are useful.
- a polymer having a hydroxyl group to which an acid anhydride is added, and the like are also useful as the aforementioned alkali-soluble resin.
- benzyl(meth)acrylate/(meth)acrylic acid copolymers and multi-component copolymers of benzyl(meth)acrylate/(meth)acrylic acid/other monomer are particularly preferred among these polymers.
- copolymer A a copolymer composed of at least (i) at least one acid component monomer selected from maleic acid anhydride (MAA), acrylic acid (AA), methacrylic acid (MA), and fumaric acid (FA), and (ii) alkylpolyoxyethylene (meth)acrylate, and (iii) benzyl (meth)acrylate.
- an average molecular weight (Mw) of the above- described copolymer in terms of polystyrene, according to GPC is preferably in the range of from 3,000 to 50,000, and more preferably from 5,000 to 30,000. [0025] If the composition ratio by mass of (i) an acid component monomer is in the above-described range, alkali solubility and dissolution properties to solvents hardly decrease.
- binder polymers having a polar group may be used singly or in the form of a composition containing the binder polymer together with an ordinary film-forming polymer.
- the addition amount of the binder polymer is generally in the range of from 10 to 200 mass parts, preferably from 25 to 100 mass parts, based on 100 mass parts of pigment fine particles.
- the number of acid groups in the polymer compound is not particularly limited; but the number of repeating units each having an acid group(s) is preferably 5 to 100, and more preferably 10 to 100, when the number of repeating units in one molecule is set to 100.
- the polymerization ratio between (1) a repeating unit derived from a compound having a carboxyl group and (2) a repeating unit derived from a compound having a carboxylate group is preferably as follows: a ratio of the repeating unit (1) is 5 to 40 mol %, a ratio of the repeating unit (2) is 40 to 90 mol %, and a ratio of a repeating unit(s) except the repeating units (1) and (2) is 25 mol % or less.
- the molecular weight of the alkali-soluble binder polymer compound having an acid group is preferably 3,000 to 1,000,000, more preferably 4,000 to 200,000, and particularly preferably 5,000 to 80,000. [0027]
- the content of the binder in the color filter of the present invention there is no particular limitation.
- the content of the binder in a colored layer is generally in the range of from 15 to 50 mass%, preferably from 20 to 45 mass%, based on the total solid content in the colored layer. If the amount of the binder is too large, viscosity of a pigment dispersion used at the time of production of the color filter becomes too high, which causes problem in production suitability. On the other hand, if the amount of the binder is too small, problems in coating film formation arise. [0028]
- photopolymerization initiator or the photopolymerization initiator series examples include vicinal polyketaldonyl compounds disclosed in U.S. Patent No.
- polymerization initiator C described in JP-A-11-133600, and oximes such as 1- phenyl-l,2-propanedion-2-(o-ethoxycarbonyl)oxime, O-benzoyl-4'-(benzmercapto)benzoyl-hexyl-ketoxime, 2,4,6-trimethylphenylcarbonyl-diphenylphosphonyloxide, and hexafluorophosphoro-trialkylphenyl phosphonium salt can also be mentioned as preferable examples.
- photopolymerization initiators and photopolymerization initiator series each may be used singly.
- a mixture of two or more selected from these photopolymerizable initiators and photopolymerization initiator series may be used.
- the display property, particularly evenness of display can be improved.
- the content of the photo-polymerization initiator and the photo-polymerization initiator series used in the color filter of the present invention there is no particular limitation.
- the content thereof in a colored layer is generally in the range of from 0.5 to 20 mass%, preferably from 1 to 15 mass%, based on the total solid content in the colored layer. If the amount of the initiator or the initiator series is too large, exposure sensitivity becomes too high, which causes difficulty in control. If the amount of the initiator or the initiator series is too small, exposure sensitivity becomes too low. [0032]
- an organic solvent may further be used.
- the organic solvent include esters, such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butylate, ethyl butylate, butyl butylate, an alkyl ester compound, methyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, alkyl 3-oxypropionate compound (e.g.
- solvents as the solvent to be used in the present invention, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, butyl acetate, methyl 3-methoxypropionate, 2- heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate and the like are preferable. These solvents may be used singly or in combination of two or more thereof. [0033] Further, if necessary, a solvent having a boiling point of from 180 °C to 250 0 C may be used.
- the high boiling solvent examples include diethyleneglycol monobutylether, diethyleneglycol monoethyletheracetate, diethyleneglycol monoethylether, 3,5,5-trimethyl-2-cyclohexene-l-on, butyl lactate, dipropyleneglycol monomethyletheracetate, propyleneglycol monomethyletheracetate, propyleneglycol diacetate, propyleneglycol-n-propyletheracetate, diethyleneglycol diethylether, 2-ethylhexylacetate, 3- methoxy-3-methylbutylacetate, ⁇ -butyllactone, tripropyleneglycol methylethylacetate, dipropyleneglycol n- butylacetate, propyleneglycol phenyletheracetate, and 1,3-butanediol diacetate.
- the content of the solvent in the color filter of the present invention is not particularly limited. However, it is preferred that the content of the solvent be 10 to 95 mass % in the pigment dispersion. [0034]
- the inkjet ink for color filter preferably comprises a suitable surfactant from the viewpoint of achieving a uniform film thickness and of prevention of color unevenness caused by variation in the film thickness effectively.
- a suitable surfactant from the viewpoint of achieving a uniform film thickness and of prevention of color unevenness caused by variation in the film thickness effectively.
- the surfactant include surfactants disclosed in JP-A-2003-337424 and JP-
- the content of the surfactant in the color filter of the present invention is not particularly limited. However, it is preferred that the content of the surfactant be 5 mass% or less based on the total solid content in the colored layer. [0035] It is preferred that the color filter of the present invention include a thermal polymerization inhibitor.
- thermal polymerization inhibitor examples include hydroquinone, hydroquinone monomethyl ether, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4'- thiobis(3-methyl-6-t-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2-mercaptobenzimidazole, and phenothiazine.
- the content of the thermal polymerization inhibitor in the color filter of the present invention is not particularly limited. However, it is preferred that the content of the thermal polymerization inhibitor in a colored layer be 1 mass% or less based on the total solid content in the colored layer.
- the color filter of the present invention may include an ultraviolet absorber.
- the ultraviolet absorber include compounds disclosed in JP-A-5-72724, a sal icy late-based ultraviolet absorber, a benzophenone-based ultraviolet absorber, a benzotriazole-based ultraviolet absorber, a cyanoacrylate-based ultraviolet absorber, a nickel-chelate-based ultraviolet absorber, and a hindered- amine-based ultraviolet absorber.
- phenyl salicylate 4-t-butyl phenylsalicylate, 2,4-di-t-butyl phenyl-3',5'-di-t-4'-hydroxybenzoate, 4-t-butyl phenylsalicylate, 2,4-dihydroxybenzophenone, 2-hydroxy-4- methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-chlorobenzotriazole, ethyl-2-cyano-3,3-diphenyl acrylate, 2,2'- hydroxy-4-methoxybenzophenone, nickel dibutyl dithiocarbamate, bis(2,2,6,6-tetramethyl-4-pyridine)- sebacate, 4-t-butyl phenylsalicylate, phenyl
- the pigment dispersion may be used in the form of an inkjet ink at the time of preparation of a colored layer. It is preferred to control the temperature of the ink so that a deviation of viscosity of the ink would be within ⁇ 5%.
- the viscosity at the time of injection is preferably from 5 to 25 mPa-s, more preferably from 8 to 22 mPa-s, and especially preferably from 10 to 20 mPa-s (the viscosity used in the present specification is a value at 25 0 C, unless specifically indicated otherwise).
- the viscosity may be adjusted by controlling the kind of components to be contained in the ink and the amount thereof. The viscosity may be measured using ordinary equipments such as a cone-and-plate-system rotational viscometer and an E type viscometer.
- the surface tension of the ink at the time of injection be from 15 to 40 mN/m, from the viewpoint of improvement in smoothness (flatness) of the pixel (surface tension used in the present specification is a value at 23 °C unless specifically indicated otherwise).
- the surface tension is more preferably from 20 to 35 mN/m, and most preferably from 25 to 30 mN/m.
- the surface tension may be adjusted by adding surfactants and selecting the kind of solvent to be used.
- the surface tension may be measured according to a platinum plate method using known measuring equipments such as a surface tension-measuring device (CBVP-Z, manufactured by Kyowa Interface Science Co., Ltd.) and a full automatic balancing type electro surface tensiometer ESB-V (manufactured by Kyowa Science).
- CBVP-Z surface tension-measuring device
- ESB-V full automatic balancing type electro surface tensiometer
- a method of spraying the above-described pigment dispersion as an inkjet ink for color filter it is possible to employ any of various methods such as a method of continuously spraying an electrified ink and then controlling the ink by electric field, and a method of intermittently spraying an ink using a piezoelectric element, and a method of intermittently spraying an ink with utilizing bubbles generated by heating the ink.
- any of ordinary methods such as a method of thermally curing an ink, a photo-curing method, and a method of previously forming a transparent image-receiving layer on a substrate, followed by stroke of ink droplets.
- an inkjet head (hereinafter sometimes simply referred to as a head), ordinary heads, such as continuous type heads and dot-on-demand type heads can be used. Of these dot-on-demand-type heads, preferred as thermal heads are those of the type having a movable bulb for discharge as described in JP-A- 9-323420.
- the piezo head use can be made of heads described in, for example, EP 277,703 A and EP 278,59OA. It is preferred that the head have a temperature control function so that the temperature of the ink can be managed.
- an injection temperature so that the viscosity at the time of injection would be within the range of from 5 to 25 mPa-s and to control the temperature of the ink so that the deviation of the viscosity would be within ⁇ 5%. It is preferred that the head operate with a drive frequency in the range of from 1 to 500 kHz.
- each pixel image element
- a thermal processing a so-called bake processing
- a substrate having thereon a layer photo-polymerized by light irradiation is heated in a heating machine such as an electric furnace and a drying oven, or alternatively said substrate is irradiated using an infrared lamp.
- the temperature and time required for heating depends on a composition of the colored photosensitive composition and the thickness of the formed layer. Generally, it is preferred to heat at a temperature of from about 120 0 C to about 250 0 C for a period of time ranging from about 10 minutes to about 120 minutes, from such the viewpoints of attaining sufficient solvent resistance, alkali resistance, and ultraviolet absorbance.
- the pattern shape of the thus-formed color filter is not particularly limited. Accordingly, it may be a stripe shape, which is a general black matrix shape, or a lattice shape, or a delta configuration shape. [0041] It is preferred to use a preparation method in which a barrier rib is formed prior to the image element-forming step using an inkjet ink for color filter, and then the ink is supplied to a portion surrounded with the barrier rib.
- the barrier rib is not particularly limited. However, in the case where a color filter is formed, it is preferred to use a barrier rib having a black matrix function and a light shielding effect (hereinafter, such the barrier rib is simply referred to as "barrier rib").
- the barrier rib may be prepared by the same materials and according to the same method as ordinary black matrixes for color filter.
- the black matrix include those described in paragraphs [0021] to [0074] of JP-A-2005-3861 and paragraphs [0012] to [0021] of JP-A-2004-240039, and black matrixes for inkjet described in paragraphs [0015] to [0020] of JP-A-2006- 17980 and paragraphs [0009] to [0044] of JP-A-2006-10875.
- the above-described pigment dispersion may be used in a form of a colored photosensitive resin composition, to form a coating film.
- the "colored photosensitive resin composition” refers to a composition containing the pigment dispersion.
- the thickness of the coating film may be properly determined. However, the thickness is preferably in the range of from 0.5 ⁇ m to 5.0 ⁇ m, and more preferably from 1.0 ⁇ m to 3.0 ⁇ m.
- a polymerized coating of the colored photosensitive resin composition may be formed by polymerizing a monomer or oligomer having a polymerizable group incorporated in the composition, thereby to prepare a color filter having the thus-formed polymerized coating.
- Polymerization of the monomer or oligomer having a polymerizable group may be performed by causing a photo-polymerization initiator or a photo-polymerization initiator series to act by irradiation of light.
- the aforementioned coating film can be formed by coating the colored photosensitive resin composition by a known coating method, followed by drying. It is preferred that the colored photosensitive resin composition be coated by using a slit nozzle having a slit at a portion through which the coating liquid is discharged. Specifically, preferable are slit nozzles and slit coaters described in JP-A- 2004-89851, JP-A-2004- 17043, JP-A-2003-170098, JP-A-2003-164787, JP-A-2003-10767, JP-A-2002- 79163, and JP-A-2001-310147. [0044]
- a spin coating is excellent in such the point that a thin film of 1 ⁇ m to 3 ⁇ m can be uniformly coated with high precision.
- the spin coating can be widely and generally used for preparation of color filters.
- it is required to further improve production efficiency and production cost in accordance with inclination to large-sized liquid crystal display devices and mass production thereof. Therefore, the slit coating, which is more suited for coating on a wide and large area substrate than the spin coating, has been adopted in production of color filters.
- the slit coating is superior to the spin coating from the viewpoint of saving of liquid to be used; and the slit coating can obtain a uniform coating from a lesser coating amount.
- the slit coating is a coating method characterized by the steps of using a coating head having a slit (gap) of a width of several ten microns at a tip and having a length corresponding to the coating width of a rectangular substrate, and moving the substrate and/or the coating head at a definite relative speed, while maintaining a clearance (gap) between the substrate and the coating head at a distance of from several ten microns to several hundred microns, and coating on the substrate a coating liquid fed from the slit in a predetermined discharge amount.
- a coating head having a slit (gap) of a width of several ten microns at a tip and having a length corresponding to the coating width of a rectangular substrate, and moving the substrate and/or the coating head at a definite relative speed, while maintaining a clearance (gap) between the substrate and the coating head at a distance of from several ten microns to several hundred microns, and coating on the substrate a coating liquid fed
- the slit coating has such advantages as follows: (1) a liquid loss is less than a spin coating; (2) a workload at the time of conducting a wash processing is reduced because no coating liquid would be spattered; (3) no contamination (re-inclusion) owing to the spattered liquid component to a coating film would be caused; (4) a tact time is shortened because no dwell time to start up spinning is necessary; (5) it easily coats a large-sized substrate. From these advantages, the slit coating is suitable to production of a color filter for a large-sized-screen liquid crystal display device, and the slit coating has been expected as a coating method that is also useful for reduction in a coating amount of the liquid. [0046]
- a coating film of much larger area can be formed by the slit coating than the spin coating. Therefore, it is necessary to keep a certain degree of relative speed between a coater and a material to be coated at the time when a coating liquid is discharged from a wide slit exit. For this reason, a good fluidity is required to a coating liquid used for the slit coating method. Further, it is particularly required for the slit coating to maintain various conditions of the coating liquid fed from a slit of the coating head to a substrate constant over the entire coating width. If solution physical properties such as fluidity and viscoelastic properties of the coating liquid are insufficient, a coating unevenness easily occurs, so that it becomes difficult to keep a coating thickness constant toward the direction of a coating width. Consequently, the coating unevenness causes such the problem that it is difficult to obtain a uniform coating. [0047]
- a photosensitive resin transfer material may be prepared by providing a photosensitive resin layer using the aforementioned colored photosensitive resin composition.
- the photosensitive resin transfer material is preferably formed by using a composite film, similarly to the photosensitive resin transfer material described in JP-A-5-72724.
- the structure of the composite film may be, for example, a lamination in which a temporary support, a thermoplastic resin layer, an intermediate layer, a photosensitive resin layer, and a protective film are disposed in this order.
- the temporary support has flexibility and does not remarkably deform, shrink, or elongate even under pressure or under pressure and heat.
- Examples of such a temporary support include a polyethylene terephthalate film, a cellulose triacetate film, a polystyrene film, and a polycarbonate film. Among them, a biaxially-stretched polyethylene terephthalate film is particularly preferable.
- the component used in the thermoplastic resin layer is preferably an organic polymer substance described in JP-A-5-72724.
- the substance is more preferably an organic polymer substance having a softening point of about 80 °C or lower according to the Vicat method (specifically, the method of measuring a polymer softening point according to American Material Test Method ASTMD 1235).
- the substance may be an organic polymer, and examples thereof include: a polyolefin such as polyethylene or polypropylene; an ethylene copolymer such as a copolymer of ethylene and vinyl acetate or a saponified product thereof; a copolymer of ethylene and acrylic acid ester or a saponified product thereof; polyvinyl chloride; a vinyl chloride copolymer such as a copolymer of vinyl chloride and vinyl acetate or a saponified product thereof; polyvinylidene chloride; a vinylidene chloride copolymer; polystyrene; a styrene copolymer such as a copolymer of styrene and (meth)acrylic acid ester or a saponified product thereof; polyvinyl toluene; a vinyltoluene copolymer such as a copolymer of vinyltoluene and (meth)acrylic acid ester or a sap
- the photosensitive resin transfer material it is preferable to provide an intermediate layer so as to prevent mixing of components during application of a plurality of coating layers and during storage after the application.
- the intermediate layer is preferably an oxygen blocking film having oxygen blocking function described as "a separating layer" in JP-A-5-72724.
- the oxygen blocking film is preferably a film with a low oxygen permeability and is dispersible or soluble in water or an aqueous alkaline solution.
- a film may be properly selected from known oxygen blocking films. Among them, a combination of polyvinyl alcohol and polyvinylpyrrolidone is particularly preferable.
- the protective film may comprise a material which is the same as or similar to that of the temporary support, but the protective film should be easily separated from the photosensitive resin layer.
- the protective film material may be, for example, silicone paper, polyolefin sheet or polytetrafluoroethylene sheet.
- the photosensitive resin transfer material can be prepared by: coating a temporary support with a coating liquid (coating liquid for thermoplastic resin layer) in which additives for a thermoplastic resin layer are dissolved and drying the coating liquid to form a thermoplastic resin layer; and then coating the thermoplastic resin layer with a coating liquid for intermediate layer containing a solvent which does not dissolve the thermoplastic resin layer, and drying the coating liquid for intermediate layer; and then, coating the intermediate layer with a coating liquid for photosensitive resin layer containing a solvent which does not dissolve the intermediate layer, and drying the coating liquid for photosensitive resin layer.
- a coating liquid coating liquid for thermoplastic resin layer
- the photosensitive resin transfer material may be prepared by: preparing a sheet in which a thermoplastic resin layer and an intermediate layer are disposed on the aforementioned temporary support, and a sheet in which a photosensitive resin layer is disposed on a protective film, and adhering the sheets to each other such that the intermediate layer and the photosensitive resin layer contact each other.
- the photosensitive resin transfer material may also be prepared by: preparing a sheet in which a thermoplastic resin layer is disposed on the aforementioned temporary support, and a sheet in which a photosensitive resin layer and an intermediate layer are disposed on a protective film, and adhering the sheets to each other such that the thermoplastic resin layer and the intermediate layer contact each other.
- the thickness of the photosensitive resin layer is preferably 1.0 to 5.0 ⁇ m, more preferably 1.0 to 4.0 ⁇ m, and particularly preferably 1.0 to 3.0 ⁇ m.
- the thickness of the temporary support is preferably 15 to 100 ⁇ m
- the thickness of the thermoplastic resin layer is preferably 2 to 30 ⁇ m
- the thickness of the intermediate layer is preferably 0.5 to 3.0 ⁇ m
- the thickness of the protective film is preferably 4 to 40 ⁇ m.
- the thicknesses of respective layers are not limited to the above ranges.
- Coating operation in the above methods may be performed by a known coating apparatus.
- a coating apparatus slit coater
- Preferable examples of the slit coater are as described above.
- the color filter of the present invention may have only a single hue, or three different hues such as red, blue, and green, or alternatively four different hues further including black, according to an end use.
- the color filter of the present invention may be used as a color filter excellent in contrast.
- contrast used in the present specification means a ratio of the amount of transmitted light when polarization axes are parallel to the amount of transmitted light when polarization axes are perpendicular, with respect to a color filter placed between two polarizing plates (see, for example, The 7th Color Optics Conference 1990; Color Filter for 512-color 10.4"-size TFT-LCD; Ueki, Koseki, Fukunaga, Yamanaka).
- the color filter having a high contrast enables enlarging a discrimination of brightness at the time when the color filter is combined with a liquid crystal. Therefore, the high contrast is a very important performance in enhancing replacement of CRTs by liquid crystal display devices.
- the contrast of the color filter according to the present invention is, if it is a monochromatic type, preferably 3,000 or more, more preferably 5,000 or more, and especially preferably 7,000 or more. With respect to a color filter having R pixel, G pixel, and B pixel, and, if necessary, further provided with a black matrix, the contrast is preferably 3,000 or more, more preferably 5,000 or more, and especially preferably 6,000 or more.
- the present invention is characterized in that such a high contrast can be realized thereby. [0057]
- chromaticity in the present invention is measured by a microscopic spectrophotometer
- the color filter of the present invention can be produced by, for example, a method of repeating, until the layers of the respective colors are provided, the process comprising: forming a photosensitive resin layer on a substrate; and exposing and developing the photosensitive resin layer. Black matrix may be introduced so as to partition the boundaries of the photosensitive resin layers, in accordance with the necessity.
- formation of the photosensitive resin layer on a substrate may be conducted, for example, by (a) applying the respective colored photosensitive resin compositions by a known coating device or by (b) using the aforementioned photosensitive resin transfer material so as to adhere the photosensitive resin layer by a laminator.
- any of known coating apparatuses may be used for applying the colored photosensitive resin composition, when producing the color filter of the present invention.
- a slit-coater is particularly preferably used.
- the slit coater are as described above.
- its film thickness is preferably 1.0 to 3.0 ⁇ m, more preferably 1.0 to 2.5 ⁇ m, and still more preferably 1.5 to 2.5 ⁇ m.
- the photosensitive resin layer formed into a film shape may be adhered to the substrate previously explained by a heated and/or pressurized roller or flat plate by pressure adhesion or heat pressure adhesion.
- laminators and laminating methods described in the following documents may be used: JP-A-7-1 10575, JP-A-11-77942, JP-A-2000-334836, and JP-A-2002- 148794. From the viewpoint of suppression of contamination by foreign substances, it is preferable to use the method described in JP-A-7-1 10575.
- an oxygen blocking film may further be provided on the photosensitive resin layer, whereby the exposure sensitivity can be improved.
- the oxygen blocking film those explained in the above can be mentioned.
- the thickness of the oxygen blocking film is not particularly limited, and the thickness is preferably 0.5 to 3.0 ⁇ m in general.
- the color filter of the present invention can be obtained by repeating, until the resin layers of the respective colors are provided, the process comprising: arranging a predetermined mask over a photosensitive resin layer formed on a substrate; exposing the photosensitive resin layer to light from above the mask which has passed through the mask, the thermoplastic resin layer, and the intermediate layer, and then developing the photosensitive resin layer with a developer.
- the light source for the exposure can be suitably selected from light sources capable of emitting lights within the wavelength region capable of curing the photosensitive resin layer (e.g. 365 nm, 405 nm, etc.). Specific examples thereof include an ultrahigh-pressure mercury lamp, a high-pressure mercury lamp, and a metal halide lamp.
- the exposure amount is usually about 5 to 200 mJ/cm 2 , and preferably about 10 to 100 mJ/cm 2 .
- the developer is not particularly limited and may be a known developer such as the developer described in JP-A-5-72724.
- the developer is preferably a developer of a type which dissolves uncured photosensitive resin layer during development; for example, a developer containing a compound with a pKa of 7 to 13 at a concentration of 0.05 to 5 mol/L is preferable.
- the developer may include a small amount of an organic solvent miscible with water.
- Examples of the organic solvent miscible with water include methanol, ethanol, 2-propanol, 1- propanol, butanol, diacetonealcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-butyl ether, benzyl alcohol, acetone, methyl ethyl ketone, cyclohexanone, ⁇ - caprolactone, ⁇ -butyrolactone, dimethylformamide, dimethylacetamide, hexamethylphosphoramide, ethyl lactate, methyl lactate, ⁇ -caprolactam, and N-methylpyrrolidone.
- the concentration of the organic solvent is preferably 0.1 mass% to 30 mass%.
- a known surfactant may be further added to the developer.
- the concentration of the surfactant is preferably 0.01 mass% to 10 mass%.
- the developing method may be a known method such as paddle development, shower development, shower & spin development, or dip development.
- the shower development will be explained.
- the developer is sprayed onto the exposed photosensitive resin layer with a shower, so that the uncured portion is removed. It is preferable to spray an alkaline solution having poor ability to dissolve the photosensitive resin layer by using a shower on the like before development, so as to remove the thermoplastic resin layer and the intermediate layer. Further, after development, it is preferable to spray a cleaner or the like by using a shower while rubbing the surface with a brush or the like to remove the development residue.
- the liquid temperature of the developer is preferably 20 0 C to 40 0 C, and the pH of the developer is preferably 8 to 13.
- the colored photosensitive resin composition for forming a color filter are stacked to form a base, a transparent electrode is formed thereon, and protrusions for split-orientation is further provided thereon to form a spacer, as described in JP-A- 1 1 -248921 and Japanese Patent No. 3255107. This embodiment is preferable from the viewpoint of cost reduction.
- the film thickness becomes smaller in every overlaying owing to the leveling of the coating liquid. For this reason, it is preferable to stack the four colors of K (black), R, G, and B and to provide protrusions for split-orientation thereon.
- the transfer material having a thermoplastic resin layer it is preferable to stack two or three colors since the thicknesses are maintained constant.
- the size of the base is preferably 25 ⁇ m x 25 ⁇ m or larger, more preferably 30 ⁇ m x 30 ⁇ m or larger.
- the liquid crystal display device of the present invention is excellent in definition such as black depth owing to the use of the color filter that is excellent in contrast according to the present invention.
- the liquid crystal display device of the present invention can be suitably used also as a large screen liquid crystal display device such as a display for a notebook computer and a television monitor.
- pigment dispersion used in the color filter of the present invention contain pigment fine particles. It is more preferred that the pigment fine particles are formed (deposited) by mixing an organic pigment solution of the organic pigment dissolved in a good solvent, together with a solvent that has compatibility with the good solvent but functions as a poor solvent for the organic pigment (hereinafter, this solvent is sometimes referred to as a “poor solvent for the organic pigment” or simply as a “poor solvent”). (Hereinafter, this method is sometimes referred to as a "fine particle deposition method").
- the poor solvent for the organic pigment is not particularly limited as long as the solvent is compatible, or mixes uniformly, with a good solvent used to dissolve the organic pigment.
- the solubility of the organic pigment in the poor solvent is preferably 0.02 mass% or less, more preferably 0.01 mass% or less.
- the solubility of the organic pigment in the poor solvent has no particular lower limit, but it is practical that the solubility is 0.000001 mass% or more in consideration of an organic pigment to be ordinarily used.
- the solubility may be solubility in the case where the organic material is dissolved in the presence of an acid or an alkali.
- compatibility or uniform mixing property between the good solvent and the poor solvent is such that the amount of the good solvent soluble in the poor solvent is preferably 30 mass% or more, more preferably 50 mass% or more.
- the amount of the good solvent soluble in the poor solvent has no particular upper limit, but it is practical that the solvents can mix with each other at an arbitrary ratio.
- Examples of the poor solvents include aqueous solvents (e.g., water, hydric alcohol, hydrochloric acid, and aqueous sodium hydroxide solution), alcohol compound solvents, ketone compound solvents, ether compound solvents, aromatic compound solvents, carbon disulfide solvents, aliphatic compound solvents, nitrile compound solvents, halogen-containing compound solvents, ester compound solvents, ionic solvents, and mixed solvents thereof.
- aqueous solvents e.g., water, hydric alcohol, hydrochloric acid, and aqueous sodium hydroxide solution
- alcohol compound solvents e.g., ketone compound solvents, ether compound solvents, aromatic compound solvents, carbon disulfide solvents, aliphatic compound solvents, nitrile compound solvents, halogen-containing compound solvents, ester compound solvents, ionic solvents, and mixed solvents thereof.
- the poor solvents include aqueous solvents, alcohol compound solvents, ketone compound solvents, ether compound solvents, ester compound solvents, and mixed solvents thereof; and more preferable examples of the poor solvents include aqueous solvents, alcohol compound solvents, and ester compound solvents.
- Examples of the alcohol compound solvents include methanol, ethanol, isopropyl alcohol, n- propyl alcohol, l-methoxy-2-propanol, and the like.
- Examples of the ketone compound solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and the like.
- Examples of ether compound solvents include dimethylether, diethylether, tetrahydrofuran, and the like.
- Examples of the aromatic compound solvents include benzene, toluene, and the like.
- Examples of the aliphatic compound solvents include hexane, and the like.
- Examples of the nitrile compound solvents include acetonitrile, and the like.
- halogen-containing compound solvents examples include dichloromethane, trichloroethylene, and the like.
- ester compound solvents examples include ethyl acetate, ethyl lactate, 2-(l-methoxy)propyl acetate, and the like.
- ionic solvents examples include a salt of 1-butyl- 3-methylimidazolium and PF 6 " , and the like.
- the good solvent is not particularly limited as long as it can dissolve the organic pigment to be used, and is compatible, or uniformly mixed, with the aforementioned poor solvent.
- the solubility of the organic pigment in the good solvent is preferably 0.2 mass% or more, and more preferably 0.5 mass% or more.
- the solubility of the organic pigment in the good solvent has no particular upper limit, but it is practical that the solubility is 50 mass% or less in consideration of an organic material to be ordinarily used.
- the solubility may be solubility in the case where the organic material is dissolved in the presence of an acid or an alkali.
- a preferable range for compatibility or uniform mixing property between the poor solvent and the good solvent is as described above. [0073]
- Examples of the good solvents include alcohol compound solvents, amide compound solvents, ketone compound solvents, ether compound solvents, aromatic compound solvents, carbon disulfide solvents, aliphatic compound solvents, nitrile compound solvents, sulfoxide compound solvents, halogen- containing compound solvents, ester compound solvents, ionic liquids, mixed solvents thereof, and the like.
- alcohol compound solvents, ketone compound solvents, ether compound solvents, sulfoxide compound solvents, ester compound solvents, amide compound solvents, and the mixed solvents thereof are preferable; alcohol compound solvents, ester compound solvents, sulfoxide compound solvents, and amide compound solvents are more preferable; and sulfoxide compound solvents and amide compound solvents are particularly preferable.
- Examples of the sulfoxide compound solvent include dimethyl sulfoxide, diethyl sulfoxide, hexamethylene sulfoxide, and sulfolane.
- Examples of the amide compound solvent include N 5 N- dimethylformamide, 1 -methyl-2-pyrrolidone, 2-pyrrolidinone, l,3-dimethyl-2-imidazolidinone, 2- pyrroridinone, ⁇ -caprolactam, formamide, N-methylformamide, acetamide, N-methylacetamide, N,N- dimethylacetamide, N-methylpropaneamide, and hexamethylphosphoric triamide. [0075]
- the concentration of the organic pigment solution prepared by dissolving the organic pigment in the good solvent is preferably in the range of the saturation concentration of the organic pigment with respect to the good solvent under conditions at the time of the dissolution to about one hundredth of the saturation concentration.
- the condition under which the organic pigment solution is prepared is not particularly restricted, and can be selected from a range from a normal pressure condition to a subcritical or supercritical condition.
- the temperature in the case where the solution is prepared under normal pressure is preferably -10 to 150 C C, more preferably -5 to 130 0 C, and particularly preferably 0 to 100 0 C.
- the identical solvent is not selected for both the good solvent and the poor solvent.
- Any solvents may be used in combination of them as long as an organic material to be used shows solubility in the good solvent sufficiently higher than that in the poor solvent.
- the difference in solubility between them is preferably 0.2 mass% or more, and more preferably 0.5 mass% or more.
- the organic pigment be uniformly dissolved in the good solvent, and further it is preferred that the organic pigment be dissolved when the solvent is acidic or alkaline.
- an alkaline solvent is used, and in the case of an organic pigment having no group dissociative under alkaline conditions but having in the molecule thereof many nitrogen atoms, to which protons easily adhere, an acidic solvent is used.
- quinacridone-, diketopyrrolopyrrole-, and condensed disazo-compound pigments are dissolved in alkaline conditions, while phthalocyanine-compound pigments are dissolved in acidic conditions.
- Examples of a base that can be used in the case that the organic pigment is dissolved in alkaline solvent include inorganic bases, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and barium hydroxide; and organic bases, such as trialkylamine, diazabicycloundecene (DBU), and metal alkoxides.
- inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, and barium hydroxide
- organic bases such as trialkylamine, diazabicycloundecene (DBU), and metal alkoxides.
- DBU diazabicycloundecene
- the amount of the base to be used is not particularly limited, as long as the base in the amount can homogeneously dissolve the pigment.
- the amount thereof is preferably from 1.0 to 30 mole equivalents, more preferably from 1.0 to 25 mole equivalents, and further preferably from 1 to 20 mole equivalents, to the organic pigment.
- the amount thereof is preferably from 1.0 to 100 mole equivalents, more preferably from 5.0 to 100 mole equivalents, and further preferably from 20 to 100 mole equivalents, to the organic pigment.
- Examples of an acid to be used in the case that the organic pigment is dissolved in the acidic solvent include inorganic acids, such as sulfuric acid, hydrochloric acid, and phosphoric acid; and organic acids, such as acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, and trifluoromethanesulfonic acid.
- inorganic acids such as sulfuric acid, hydrochloric acid, and phosphoric acid
- organic acids such as acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, and trifluoromethanesulfonic acid.
- the inorganic acids are preferable, and sulfuric acid is especially preferable.
- the amount of the acid to be used is not particularly limited, as long as the acid in the amount can homogenously dissolve the organic pigment. In many cases, the acid is used in a larger or more excessive amount than the base. Regardless the kind of the acid being an inorganic acid or an organic acid, the amount of the acid to be used is preferably from 3 to 500 mole equivalents, more preferably from 10 to 500 mole equivalents, and further preferably from 30 to 200 mole equivalents, to the organic pigment. [0081]
- a solvent having high solubility for the alkali or the acid such as water or a lower alcohol can be added in a slight amount to the organic solvent in order that the alkali or the acid may be completely dissolved.
- the amount of water or the lower alcohol is preferably 50 mass% or less, or more preferably 30 mass% or less with respect to the total amount of the organic pigment solution. Specific examples thereof that can be used include water, methanol, ethanol, n-propanol, isopropanol, and butyl alcohol.
- the condition for the poor solvent at the time of depositing the organic pigments is not particularly restricted, and can be selected from a range from a normal pressure condition to a subcritical or supercritical condition.
- the temperature at which the organic particles are deposited under normal pressure is preferably -30 to 100 °C, more preferably -10 to 60 0 C, and particularly preferably 0 to 30 0 C.
- the viscosity of the liquid containing precipitated pigment fine particles is preferably in the range of from 0.5 to 80.0 mPa s, and more preferably from 1.0 to 50.0 mPa-s.
- an organic pigment solution and a poor solvent either of them may be added to the other to mix them.
- mixing is conducted by adding the organic pigment solution to the poor solvent; and it is also preferred that the poor solvent be in a state of being stirred at the time of mixing.
- the stirring rate is preferably 100 to 10,000 rpm, more preferably 150 to 8,000 rpm, and particularly preferably 200 to 6,000 rpm.
- a pump or the like may be or may not be used for adding.
- the adding method a method of adding a liquid inside the other liquid or a method of adding a liquid outside the other liquid may be used; a method of adding a liquid inside the other liquid is preferable.
- one of the liquids be successively fed from inside of the other liquid through a feed pipe using a pump.
- the inner diameter of the feed pipe is preferably in the range of from 0.1 mm to 200 mm, and more preferably from 0.2 mm to 100 mm.
- the speed fed from the feed pipe into the other liquid is preferably in the range of from 1 to 10,000 ml/min, and more preferably from 5 to 5,000 ml/min.
- the mixing ratio of the organic pigment solution and the poor solvent is preferably in a range of from 1/50 to 2/3, more preferably from 1/40 to 1/2, and especially preferably from 1/20 to 3/8, in terms of volume ratio.
- the pigment concentration in the liquid containing precipitated pigment fine particles is not particularly limited, as long as organic particles can be prepared, but the amount of the organic particles is preferably 10 to 40,000 mg, more preferably 20 to 30,000 mg, and particularly preferably 50 to 25,000 mg, per 1,000 ml of the dispersion solvent.
- the scale of preparation at the time when the pigment fine particles are prepared is no particular limitation to the scale of preparation at the time when the pigment fine particles are prepared.
- the preparation scale is such that the amount of the poor solvent to be mixed is preferably from 10 to 2,000 L, and more preferably from 50 to 1,000 L.
- an average scale of a group can be digitalized by several measurement methods.
- the particle diameter means a number-averaged diameter, unless otherwise particularly specified.
- the particle diameter of the pigment fine particles is preferably 1 nm to 1 ⁇ m, more preferably 1 to 100 nm, further preferably 5 to 80 nm, and particularly preferably 5 to 50 nm.
- the organic particles may be crystalline particles, amorphous particles, or a mixture of these particles, or in a state of a solid solution.
- a ratio (Mv/Mn) of volume-averaged diameter (Mv) to number- averaged diameter (Mn) is used as the indicator of the monodispersity of particles (degree of the uniformity in particle size), unless otherwise particularly specified.
- the monodispersity, the ratio Mv/Mn, of the pigment fine particles (primary particles) is preferably 1.0 to 2.0, more preferably 1.0 to 1.8, and particularly preferably 1.0 to 1.5.
- Examples of a method of measuring the particle diameter of organic particle include a microscopic method, a gravimetric method, a light scattering method, a light shielding method, an electric resistance method, an acoustic method, and a dynamic light scattering method. Of these, the microscopic method and the dynamic light scattering method are particularly preferable.
- Examples of a microscope to be used in the microscopic method include a scanning electron microscope and a transmission electron microscope.
- Examples of a particle measuring device according to the dynamic light scattering method include Nanotrac UPA-EX 150 (trade name) manufactured by NIKKISO Co., Ltd., and a dynamic light scattering photometer DLS-7000 series (trade name) manufactured by OTSUKA ELECTRONICS CO., LTD. [0084]
- a dispersing agent is preferably incorporated therein.
- the step of incorporating the dispersing agent it is preferred to add the dispersing agent to both or any one of the organic pigment solution and the poor solvent.
- pigment fine particles that have been previously surface-processed with a dispersing agent; the pigment particles may be subjected to a surface treatment capable of promoting adsorption of the dispersing agent onto the pigment particles.
- the dispersing agent has functions (1) that the dispersing agent is rapidly adsorbed on the surface of the precipitated pigment, to form fine nanoparticles, and (2) that the dispersing agent prevents these particles from aggregating again.
- the dispersing agent use can be made of an anionic, cationic, amphoteric, nonionic or pigment-derivative-type, and low-molecular-weight or polymer dispersing agent.
- the molecular weight of the polymer dispersing agent for use may be any value, as long as the dispersing agent can be uniformly dissolved in a solution, but the polymer dispersing agent preferably has a molecular weight of 1 ,000 to 2,000,000, more preferably of 5,000 to 1 ,000,000, still more preferably of 10,000 to 500,000, and particularly preferably of 10,000 to 100,000.
- polymer dispersing agent examples include polyvinyl pyrrolidone, polyvinyl alcohol, polyvinyl methyl ether, polyethylene oxide, polyethylene glycol, polypropylene glycol, polyacrylamide, vinyl alcohol/vinyl acetate copolymer, partial-formal products of polyvinyl alcohol, partial-butyral products of polyvinyl alcohol, vinylpyrrolidone/vinyl acetate copolymer, polyethylene oxide/propylene oxide block copolymer, polyacrylic acid salts, polyvinyl sulfuric acid salts, poly(4-vinylpyridine) salts, polyamides, polyallylamine salts, condensed naphthalenesulfonic acid salts, cellulose derivatives, and starch derivatives.
- natural polymers can be used, examples of which include alginic acid salts, gelatin, albumin, casein, gum arabic, tragacanth gum, and ligninsulfonic acid salts. Above all, it is preferred to use any of the aforementioned water-soluble polymers, and it is more preferred to use polyvinyl pyrrolidone. These polymers may be used singly or in combination of two or more. These dispersing agents may be used singly or in combination of two or more thereof. The dispersing agents to be used when dispersing a pigment are described in detail in "Dispersion Stabilization of Pigment and Surface Treatment Technique/Evaluation" (published by Japan Association for International Chemical Information, on December 2001), pp. 29-46. [0086]
- anionic dispersing agent examples include N-acyl-N-alkyltaurine salts, fatty acid salts, alkylsulfates, alkylbenzenesulfonates, alkylnaphthalenesulfonates, dialkylsulfosuccinates, alkylphosphates, naphthalenesulfonic acid/formalin condensates, and polyoxyethylenealkylsulfates.
- N- acyl-N-alkyltaurine salts are particularly preferable.
- the N-acyl-N-alkyltaurine salts those described in JP-A-3-273067 are preferable.
- These anionic dispersing agents may be used singly or in combination of two or more thereof.
- cationic dispersing agent examples include quaternary ammonium salts, alkoxylated polyamines, aliphatic amine polyglycol ethers, aliphatic amines, diamines and polyamines derived from aliphatic amine and aliphatic alcohol; imidazolines derived from aliphatic acid, and salts of these cationic substances. These cationic dispersing agents may be used singly or in combination of two or more thereof.
- the amphoteric dispersing agent is a dispersing agent having, in the molecule thereof, an anionic group moiety which the anionic dispersing agent has in the molecule and a cationic group moiety which the cationic dispersing agent has in the molecule.
- nonionic dispersing agents examples include polyoxyethylenealkyl ethers, polyoxyethylenealkylaryl ethers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, polyoxyethylenesorbitan fatty acid esters, polyoxyethylenealkylamines, and glycerin fatty acid esters.
- polyoxyethylenealkylaryl ethers are preferable.
- These nonionic dispersing agents may be used singly or in combination of two or more thereof.
- the pigment-derivative-type dispersing agent is defined as a dispersing agent that is derived from an organic pigment as a parent material and prepared by chemically modifying a structure of the parent material or that is obtained by a pigment-forming reaction of a chemically-modified pigment precursor.
- pigment-derivative-type dispersing agent examples include sugar-containing pigment-derivative-type dispersing agents, piperidyl-containing pigment-derivative-type dispersing agents, naphthalene- or perylene-derivative pigment-derivative-type dispersing agents, pigment-derivative-type dispersing agents having a functional group linked through a methylene group to a pigment parent structure, pigment- derivative-type dispersing agents (parent structure) chemically modified with a polymer, pigment- derivative-type dispersing agents having a sulfonic acid group, pigment-derivative-type dispersing agents having a sulfonamido group, pigment-derivative-type dispersing agents having an ether group, and pigment-derivative-type dispersing agents having a carboxylic acid group, carboxylic acid ester group, or carboxamido group.
- a pigment dispersing agent containing an amino group coexists with the organic pigment.
- the term "amino group” described herein embraces a primary amino group, a secondary amino group, and a tertiary amino group. The number of the amino group may be one or plural.
- the pigment dispersing agent containing an amino group may be a pigment derivative compound wherein a substituent having an amino group is introduced to the skeleton of the pigment, or may be a polymer compound polymerized using a monomer having an amino group as a polymerization component.
- A represents a component capable of forming an azo dye together with X-Y.
- the component A can be arbitrarily selected as long as the component is capable of forming an azo dye upon coupling with a diazonium compound. Specific examples of the component A are shown below, but the present invention is not limited to these compounds. [0094] [Chemical formula 2] F Formula 1 —2
- X represents a single bond, or a group selected from divalent connecting groups represented by structural formulae of formulae (i) to (v) set forth below. [0097] [Chemical formula 4]
- Z represents a lower alkylene group.
- Z can be expressed as
- -NR 2I represents a lower alkylamino group, or a nitrogen-containing, 5- or 6-membered, saturated heterocyclic group.
- the lower alkylamino group can be expressed as -N(C r H 2r+ i) 2 wherein r represents an integer of from 1 to 4, and preferably 1 or 2.
- the heterocyclic group is preferably any one of the heterocyclic groups shown by the following structural formulae. [0101] [Chemical formula 6]
- Each of Z and -NR 2 ] in the above-described formula (D2) may optionally have a lower alkyl group or an alkoxy group, as a substituent.
- a represents 1 or 2, and preferably 2.
- Q represents a residue of an organic dye selected from anthraquinone compound dyes, azo compound dyes, phthalocyanine compound dyes, quinacridone compound dyes, dioxazine compound dyes, anthrapyrimidine compound dyes, anthanthrone compound dyes, indanthrone compound dyes, flavanthrone compound dyes, pyranthrone compound dyes, perynone compound dyes, perylene compound dyes, and thioindigo compound dyes.
- organic dyes preferred are azo compound dyes and dioxazine compound dyes. The azo compound dyes are more preferred.
- X 1 represents -CO-, -CONH-Y 2 -, -SO 2 NH-Y 2 -, or -CH 2 NHCOCH 2 NH-Y 2 -.
- X 1 is preferably -CO- or -CONH-Y 2 -.
- Y 2 represents an alkylene group or an arylene group, each of which may be substituted. Among these groups, preferred are a phenylene group, a toluilene group, and a hexylene group. The phenylene group is more preferred.
- R 11 and R 12 each independently represent a substituted or unsubstituted alkyl group, alternatively, R n and R 12 may be bonded together to form a heterocyclic group which at least contains a nitrogen atom.
- R n and R 12 may be bonded together to form a heterocyclic group which at least contains a nitrogen atom.
- preferred are a methyl group, an ethyl group, a propyl group, and a pyrrolidinyl group which contains a nitrogen atom.
- the ethyl group is more preferred.
- Yi represents -NH- or -O-.
- Zi represents a hydroxyl group or a group represented by formula (D3a) with the proviso that in the case where nl is 1, Z x may be -NH-X 1 -Q.
- ml represents an integer of 1 to 6, and preferably 2 or 3.
- nl represents an integer of 1 to 4, and preferably 1 or 2. [0112] [Chemical formula 12]
- the compounds represented by formula (D3) can be obtained, for example, by reaction of a dye compound with an intermediate which is obtained by a reaction of a halogenated triazine compound with an amine compound having Rn and R 12 and an alcohol compound having R n and R 12 .
- the disclosure of the specification of JP-B-5-72943 can be also referred for the synthesis of the compound. [0120] ⁇ 3. Pigment dispersing agent containing graft copolymer>
- the above-described graft copolymer at least has an amino group and an ether group, and also may contain other monomers as a copolymer unit.
- the weight-average molecular weight of the graft copolymer is preferably in a range of from 3,000 to 100,000, and more preferably in a range of from 5,000 to 50,000. If the weight-average molecular weight is too small, it is difficult to prevent the pigment fine particles from aggregating, which sometimes results in elevation of viscosity. If the weight-average molecular weight is too large, solubility to an organic solvent becomes insufficient, which sometimes results in elevation of viscosity. [0121]
- the above-described graft copolymer contain as copolymer units, at least (i) a polymerizable oligomer having an ethylenically unsaturated double bond at a terminal, (ii) a monomer having an amino group and an ethylenically unsaturated double bond, and (iii) a polymerizable monomer having an ether group, and also, if necessary, contain (iv) other monomer(s).
- the content of each of the copolymer units in the graft copolymer is as follows: the content of (i) the polymerizable oligomer is preferably in the range of from 15 to 98 mass%, more preferably from 25 to 90 mass%, the content of (ii) the amino-group-containing monomer is preferably in the range of from 1 to 40 mass%, more preferably from 5 to 30 mass%, and the content of (iii) the polymerizable monomer having an ether group is preferably in the range of from 1 to 70 mass%, more preferably from 5 to 60 mass%.
- the content of the polymerizable oligomer is too small, a stereo-repulsion effect that should be attained by a dispersing agent is hardly obtained, and it sometimes becomes difficult to prevent the pigment fine particles from aggregating. If the content of the polymerizable oligomer is too large, the ratio of the amino-group-containing monomer relatively decreases so that adsorption capacity to organic particles is lowered, and dispersibility sometimes becomes insufficient. If the content of the amino-group-containing monomer is too small, dispersibility sometimes becomes insufficient owing to reduction of the adsorption capacity to organic particles.
- the content of the amino-group-containing monomer is too large, the ratio of the polymerizable oligomer relatively decreases so that a stereo-repulsion effect that should be attained by a dispersing agent is hardly obtained, and it sometimes becomes difficult to sufficiently prevent the pigment fine particles from aggregating. If the content of the polymerizable monomer having an ether group is too small, development suitability at the time of production of color filters and the like sometimes become insufficient. If the content of the polymerizable monomer having an ether group is too large, a capacity as a dispersing agent sometimes reduces.
- the polymerizable oligomer (hereinafter, sometimes also referred to as "macro monomer”) has a group having an ethylenically unsaturated double bond at one or both ends (terminals) thereof.
- the oligomer it is preferred in the present invention that the oligomer have a group having an ethylenically unsaturated double bond at only one of the ends of the oligomer.
- oligomer As the aforementioned oligomer, homopolymers or copolymers formed from at least one monomer selected from such monomers as alkyl (meth)acrylates, hydroxyalkyl (meth)acrylates, styrene, acrylonitrile, vinyl acetate, and butadiene can be mentioned. Among these oligomers, preferred are homopolymers or copolymers of alky 1 (meth)acrylates and polystyrene. In the present invention, these oligomers may further be substituted. There is no particular limitation to the substituent; a halogen atom can be mentioned as an example of the substituent. [0126] Examples of the group having an ethylenically unsaturated double bond include a (meth)acryloyl group and a vinyl group. Among these groups, (meth)acryloyl group is especially preferred. [0127]
- oligomers for use in the present invention, preferred are oligomers represented by formula (E6) set forth below. [0128]
- R 61 and R 63 each represents a hydroxyl group or a methyl group.
- R 62 represents an alkylene group which has 1 to 8 carbon atoms and which may be substituted by an alcoholic hydroxyl group, and R 62 preferably represents an alkylene group having 2 to 4 carbon atoms.
- Y 6 represents a phenyl group, a phenyl group having an alkyl group having 1 to 4 carbon atoms, or -COOR 64 (R 64 represents an alkyl group which has 1 to 6 carbon atoms and which may be substituted by an alcoholic hydroxyl group or halogen atom; a phenyl group, or an aralkyl group having 7 to 10 carbon atoms); and Y 6 preferably represents a phenyl group or -COOR 164 (R 164 represents an alkyl group which has 1 to 4 carbon atoms and which may be substituted with an alcoholic hydroxyl group), q represents a number of from 20 to 200. [0130]
- polymerizable oligomer examples include poly-2-hydroxyethyl (meth)acrylate, polystyrene, poly-methyl (meth)acrylate, poly-n-butyl (meth)acrylate, poly-i-butyl (meth)acrylate, and copolymers of these monomers.
- polymers preferred are polymers having a (meth)acryloyl group bonded to one terminal of the molecule.
- the polymerizable oligomer may be a commercially available product, or may be appropriately synthesized.
- a preferable specific example of the polymerizable oligomer in the present invention is at least one kind of an oligomer selected from a polymer of an alkyl (meth)acrylate and a copolymer of an alkyl (meth)acrylate and polystyrene, with the oligomer having a number average molecular weight of 1 ,000 to 20,000, and with the oligomer having a (meth)acryloyl group at a terminal.
- amino-group-containing monomer a preferable example is any one of the compounds represented by formula (E2) set forth below. [0134] [Chemical formula 17]
- R 21 represents a hydroxyl group or a methyl group.
- R 22 represents an alkylene group having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, and especially preferably 2 to 3 carbon atoms
- X 2 represents -N(R 23 )(R 24 ), or -R 25 N(R 26 )(R 27 ), wherein R 23 and R 24 each represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and R 25 represents an alkylene group having 1 to 6 carbon atoms, and R 26 and R 27 each represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
- R 23 and R 24 of the -N(R 23 )(R 24 ) are preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and R 25 of the -R 25 N(R 26 )(R 27 ) is preferably an alkylene group having 2 to
- R 26 and R 27 are preferably an alkyl group having 1 to 4 carbon atoms.
- R 41 has the same meaning as R 21 .
- X 4 has the same meaning as X 2 , and X 4 is preferably -N(R 43 XR 44 ) (wherein R 43 and R 44 have the same meanings as R 23 and R 24 ), or -R 45 N(R 46 XR 47 ) (wherein R 45 , R 46 , and R 47 have the same meaning as R 25 , R 26 , and R 27 ).
- the monomer represented by the above-described formula (E2) include (meth)acrylamides such as dimethyl (meth)acrylamide, diethyl(meth)acrylamide, diisopropyl(meth)acrylamide, di-n-butyl(meth)acrylamide, di-i-butyl(meth)acrylamide, morpholino(meth)acrylamide, piperidino(meth)acrylamide, N-methyl-2-pyrrolidyl(meth)acrylamide, and N,N-methylphenyl(meth)acrylamide; and aminoalkyl(meth)acrylamides such as 2-(N,N- dimethylamino)ethyl (meth)acrylamide, 2-(N,N-diethylamino)ethyl(meth)acrylamide, 3-(N,N- diethylamino)propyl(meth)acrylamide, 3-(N,N-dimethylamino) propyl(meth)acrylamide, 1-(meth)acryl
- R" represents a hydrogen atom or a methyl group.
- R 12 represents an alkylene group having 1 to 8 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms, and more preferably an alkylene group having 2 to 3 carbon atoms.
- X 1 represents -OR 13 or -OCOR 14 .
- R 13 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a phenyl group, or a phenyl group substituted with an alkyl group having 1 to 18 carbon atoms.
- R 14 represents an alkyl group having 1 to 18 carbon atoms.
- m3 denotes a number of 2 to 200, preferably 5 to 100, and particularly preferably 10 to 100.
- the polymerizable monomer having an ether group can be appropriately selected from conventional known monomers.
- the monomer can be appropriately selected from conventional known monomers. Examples thereof include polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, polyethylene glycol polypropylene glycol mono(meth)acrylate, and polytetramethylene glycol monomethacrylate. These materials may be commercially available products or may be those synthesized properly.
- Examples of these commercially available products include methoxypolyethylene glycol methacrylate (trade name: NK ESTER M-40G, M-90G, and M-230G (manufactured by Toagosei Co., Ltd.); trade name: BLENMER-PME- 100, PME-200, PME-400, PME-1000, PME-2000, and PME-4000 (manufactured by Nippon Oil & Fats Co., Ltd.)), polyethylene glycol monomethacrylate (trade name: BLENMER-PE-90, PE-200, and PE-350 (manufactured by Nippon Oil & Fats Co., Ltd.)); polypropylene glycol monomethacrylate (trade name: BLENMER-PP-500, PP-800, and PP-1000 (manufactured by Nippon Oil & Fats Co., Ltd.)), polyethylene glycol polypropylene glycol monomethacrylate (trade name: BLENMER-70
- the above-described graft copolymers may contain, additionally, the above-described other monomer(s) as a copolymer unit.
- the other monomers are not particularly limited, and they can be properly selected in accordance with purposes.
- Examples of the other monomers include aromatic vinyl compounds (e.g., styrene, ⁇ -methyl styrene, vinyl toluene), alkyl (meth)acrylates (e.g., methyl(meth)acrylate, ethyl(meth)acrylate, n-butyl(meth)acrylate, i-butyl(meth)acrylate), alkylaryl(meth)acrylates (e.g., benzyl(meth)acrylate), glycidyl(meth)acrylate, vinyl carboxylates (e.g., vinyl acetate, vinyl propionate), vinyl cyanides (e.g., (meth)acrylonitrile, ⁇ -chloro acrylonitrile), aliphatic conjugate dienes (e.g., 1 ,3-butadiene, isoprene), and (meth)acrylic acid.
- aromatic vinyl compounds e.g., styrene, ⁇
- the content of the other monomers in the above-described graft copolymers is, for example, preferably in the range of from 5 to 70 mass%. If the content is too small, it sometimes becomes difficult to control physical properties of the coating film. If the content is too large, it sometimes becomes difficult for the graft copolymer to fully exhibit its capacity as a dispersing agent. [0150]
- graft copolymers Preferable specific examples include:
- the above-described graft copolymers can be obtained by subjecting components that constitute units of the above-described copolymers to, for example, radical polymerization in a solvent.
- a radical polymerization initiator may be used.
- a chain transfer agent e.g., 2-mercapto ethanol and dodecyl mercaptan.
- a pigment dispersing agent containing a graft copolymer can be also prepared with reference to descriptions of JP-A-2001-31885.
- the content of the dispersing agent is preferably in the range of from 0.1 to 1000 mass parts, more preferably from 1 to 500 mass parts, and furthermore preferably from 5 to 20 mass parts, based on 100 mass parts of the pigment. A too-small content sometimes results in no improvement in dispersion stability of the pigment fine particles.
- the dispersing agent may be used singly or in combination of plural dispersing agents.
- the content of the dispersing agent is preferably in the range of from 0.1 to 1000 mass parts, more preferably from 1 to 500 mass parts, and furthermore preferably from 5 to 20 mass parts, based on 100 mass parts of the organic particles. A too-small content sometimes results in no improvement in dispersion stability of the organic particles.
- the dispersing agent may be used singly or in combination of plural dispersing agents.
- the pigment fine particle dispersion may be subjected to desalting and condensation, whereby a concentrated liquid suitable for a color filter coating liquid or for inkjet ink can be produced on an industrial scale.
- the condensation method is not particularly restricted as long as the pigment fine particle liquid can be concentrated by the method.
- a preferable condensation method include: a method involving adding and mixing an extraction solvent to and with a pigment fine particle dispersion, condensing and extracting the pigment fine particles to the extraction solvent phase, and filtering the concentrated extract liquid through a filter or the like, to provide a concentrated nanoparticles liquid; a method involving sedimenting the pigment fine particles by centrifugal separation for condensation; a method involving performing desalting and condensation by ultrafiltration; a method involving sublimating a solvent by vacuum freeze-drying for condensation; and a method involving drying a solvent under heat or reduced pressure for condensation.
- a combination of two or more of these methods is extremely preferably employed.
- the pigment fine particle concentration after condensation is preferably 1 to 100 mass%, more preferably 5 to 100 mass%, and particularly preferably 10 to 100 mass%.
- the extraction solvent for use in the process of concentrating and extracting is not particularly limited, but it is preferably a solvent that is substantially incompatible (immiscible) with the dispersion solvent of the pigment fine particle dispersion (e.g., aqueous solvent) (in the present specification, the term "substantially incompatible” means that the compatibility is low, and the amount of the extraction solvent soluble in the dispersion solvent is preferably 50 mass% or less, and more preferably 30 mass% or less; although the amount of the extraction solvent soluble in the dispersion solvent has no particular lower limit, it is practical that the amount is 1 mass% or more in consideration of the solubility in an ordinary solvent), and that forms an interface after the extraction solvent is mixed with the dispersion solvent and left still.
- the extraction solvent is preferably a solvent that causes weak aggregation to such a degree that the pigment fine particles can be redispersed in the extraction solvent.
- weak, redispersible aggregation means a floe that can be redispersed without applying high shearing force such as by milling or high-speed agitation. Such a state is preferable, because it is possible to prevent strong aggregation that may change the particle size, and to swell the desirable pigment fine particles with the extraction solvent, besides the dispersion solvent such as water can be easily and rapidly removed by filter-filtration.
- ester compound solvents As the extraction solvent, ester compound solvents, alcohol compound solvents, aromatic compound solvents, and aliphatic compound solvents are preferable; ester compound solvents, aromatic compound solvents, and aliphatic compound solvents are more preferable; and ester compound solvents are particularly preferable.
- ester compound solvent examples include 2-(l-methoxy)propyl acetate, ethyl acetate, ethyl lactate, and the like.
- alcohol compound solvent examples include n-butanol, isobutanol, and the like.
- aromatic compound solvent examples include benzene, toluene, xylene, and the like.
- the aliphatic compound solvent examples include n-hexane, cyclohexane, and the like.
- the extraction solvent may be a pure solvent of one of the preferable solvents above, while it may be a mixed solvent of multiple solvents.
- the amount of the extraction solvent is not particularly limited, as long as the solvent can extract the pigment fine particles, but the amount of the extraction solvent is preferably smaller than the amount of the pigment fine particle dispersion, considering extraction for concentration. If expressed by volume ratio, the amount of the extraction solvent to be added is preferably in the range of 1 to 100, more preferably in the range of 10 to 90, and particularly preferably in the range of 20 to 80, with respect to 100 of the pigment fine particle dispersion. A too-large amount may results in elongation of the period for concentration, while a too-small amount may cause insufficient extraction and residual nanoparticles in the dispersion solvent.
- the extraction solvent After addition of the extraction solvent, it is preferably agitated well for sufficient mutual contact with the dispersion. Any conventional method may be used for agitation and mixing.
- the temperature during addition and mixing of the extraction solvent is not particularly limited, but preferably 1 to 100 0 C and more preferably 5 to 60 0 C.
- Any apparatus may be used for addition and mixing of the extraction solvent as long as it can suitably carry out each step. For example, a separatory funnel-like apparatus may be used.
- the constant volume method As a method for supplementing the solvent lost due to passage through the membrane, there are the constant volume method - • where the solvent is continuously supplemented and the batch method where the solvent is intermittently added.
- the constant volume method is preferred in the present invention because of its relatively shorter desalting treatment time.
- pure water obtained by ion exchange or distillation is generally used.
- a dispersing agent or a poor solvent for dispersing agent may be mixed in the pure water.
- the dispersing agent or the poor solvent for dispersing agent can also be directly added to the pigment fine particle dispersion.
- modules of plate type, spiral type, cylinder type, hollow yarn type, hollow fiber type and so forth, in which a membrane is already incorporated are commercially available from Asahi Chemical Industry Co., Ltd., Daicel Chemical Industries, Ltd., Toray Industries, Inc., NITTO DENKO CORP. and so forth.
- the fractional molecular weight which is an index of a threshold for substances that can permeate a membrane, must be. determined based on the molecular weight of the used dispersing agent. In the present invention, those having a fractional molecular weight of 5,000 to 50,000, more preferably 5,000 to 15,000, are preferably used.
- filtration by using a filter is preferable.
- an apparatus such as a high-pressure filtration apparatus can be used.
- Preferable filters include nanofilter, ultrafilter and the like. It is preferable to remove a residual dispersion solvent by filter filtralation, so as to further concentrate pigment fine particles in the concentrated extract liquid and to obtain a concentrated nanoparticle liquid.
- a method for freeze-drying is not particularly limited, and any method may be adopted as long as a person skilled in the art can utilize the method.
- the freeze-drying method include a coolant direct expansion method, a multiple freezing method, a heating medium circulation method, a triple heat exchange method, and an indirect heating freezing method.
- the coolant direct-expansion method or the indirect heating freezing method is preferably employed, and the indirect heating freezing method is more preferably employed.
- preliminary freezing is preferably performed before freeze- drying is performed.
- Conditions for freeze-drying are not particularly limited, but a sample to be subjected to freeze-drying must be uniformly frozen. [0165]
- Examples of a device for the indirect heating freezing method include a small freeze-drying machine, an FTS freeze-drying machine, an LYOVAC freeze-drying machine, an experimental freeze- drying machine, a research freeze-drying machine, a triple heat exchange vacuum freeze-drying machine, a monocooling-type freeze-drying machine, and an HULL freeze-drying machine.
- the small freeze-drying machine, the experimental freeze-drying machine, the research freeze-drying machine, or the monocooling-type freeze-drying machine is preferably used, and the small freeze-drying machine or the monocooling-type freeze-drying machine is more preferably used.
- the temperature for freeze-drying which is not particularly limited, is, for example, about -190 to -4°C, preferably about -120 to -20 0 C, and more preferably about -80 to -60 0 C.
- the pressure for freeze- drying is not particularly limited either, and can be appropriately selected by a person skilled in the art. It is recommended that freeze-drying be performed under a pressure of, for example, about 0.1 to 35 Pa, preferably about 1 to 15 Pa, and more preferably about 5 to 10 Pa.
- the time period for freeze-drying is, for example, about 2 to 48 hours, preferably about 6 to 36 hours, or more preferably about 16 to 26 hours. It should be noted, however, that these conditions can be appropriately selected by a person skilled in the art.
- the centrifugal separator for use in the condensation of the pigment fine particles by centrifugal separation may be an arbitrary device as long as the pigment fine particles in the pigment fine particle dispersion (or the pigment fine particles concentrated extract liquid) can be sedimented.
- the centrifugal separator include a general-purpose device, a system having a skimming function (function with which a supernatant layer is sucked during the rotation of the system, to discharge to the outside of the system), and a continuous centrifugal separator for continuously discharging solid matter.
- a centrifugal force (a value representing a ratio of an applied centrifugal acceleration to the gravitational acceleration) is preferably 50 to 10,000, more preferably 100 to 8,000, and particularly preferably 150 to 6,000.
- the temperature at the time of centrifugal separation is preferably -10 to 8O 0 C, more preferably -5 to 70°C, and particularly preferably 0 to 60 0 C, though a preferable temperature varies depending on the kind of the solvent of the dispersion.
- the device for use in the condensation of the pigment fine particles by drying under reduced pressure is not particularly limited as long as the solvent of the pigment fine particle dispersion (or the pigment fine particles concentrated extract liquid) can be evaporated.
- the device include a general-purpose vacuum drier and a general-purpose rotary pump, a device capable of drying a liquid under heat and reduced pressure while stirring the liquid, and a device capable of continuously drying a liquid by passing the liquid through a tube the inside of which is heated and reduced in pressure.
- the temperature for drying under heat and reduced pressure is preferably 30 to 230 0 C, more preferably 35 to 200 0 C, or particularly preferably 40 to 180 0 C.
- the pressure for the above-mentioned reduced pressure is preferably 100 to 100,000 Pa, more preferably 300 to 90,000 Pa, and particularly preferably 500 to 80,000 Pa.
- the pigment fine particles can be efficiently concentrated from the pigment fine particle dispersion.
- the condensation ratio is, for example, as follows: when the concentration of the nanoparticles in the pigment fine particle dispersion serving as a raw material is set to 1, the concentration in a concentrated pigment fine particles paste can be preferably about 100 to 3,000 times, and more preferably about 500 to 2,000 times. [0170]
- the concentration in a concentrated pigment fine particles paste can be preferably about 100 to 3,000 times, and more preferably about 500 to 2,000 times.
- fining and dispersing When pigment fine particles are in the state of aggregation owing to the aforementioned concentration etc, it is preferred to subject the aggregation to fining and dispersing. (In the present specification, the term "fining and dispersing" means a process to release particles in a dispersion from the aggregation state, thereby to enhance degree of dispersion.)
- the organic particles contained in an organic particle liquid condensed by the above-described extraction solvent, centrifugal separation, and drying etc. are ordinarily in the state of aggregation owing to condensation of the organic particles.
- the aforementioned pigment fine particles in order to enable a rapid filtration and to obtain an excellent dispersion state again, it is preferred to obtain the aforementioned pigment fine particles as a flock.
- the flock is an assembly of fine particles weakly aggregate to each other to a degree allowing redispersion (soft- aggregated).
- nonaqueous dispersion composition dispersed in an organic solvent (nonaqueous dispersion composition) efficiently, by redispersing the separated floe (soft aggregate) in the organic solvent suitable for preparation of color filter.
- the mixed solvent of good and poor solvents is an aqueous solvent
- the average diameter of the floe is not particularly limited, but it is preferably 0.5 to 500 ⁇ m, more preferably 5 to 100 ⁇ m, considering the filtration efficiency described above.
- solvents different from both of the good solvent (first solvent) and the poor solvent (second solvent) are collectively called "third solvents”.
- the term “aggregated organic particles” means an assembly of organic particles gathered together by a secondary force, such as aggregates; in the case of nanometer- sized primary particles, they are also referred to as “aggregated nanoparticles”.
- the term “aggregated organic particles liquid” means a liquid containing aggregated organic particles, and the liquid may be, for example, a dispersion, a concentrated liquid, a paste, or slurry as long as the liquid contains the aggregated organic particles.
- the favorable fine dispersibility property giving uniform and fine particle diameter
- the favorable dispersion stability property maintaining uniform and fine particle diameter for an extended period of time
- a 1 represents a monovalent organic group having a group selected from the group consisting of an acidic group, a nitrogen-containing basic group, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxy silyl group, an epoxy group, an isocyanate group, and a hydroxyl group, or a monovalent organic group containing an organic dye structure or heterocycle each of which may further be substituted. If n is two or more, plural A 1 S may be the same or different. Specifically, A 1 is not particularly limited.
- Examples of the "monovalent organic group having an acidic group” include a monovalent organic group having an acid group such as a carboxylic acid group, a sulfonic acid group, a monosulfuric acid ester group, a phosphoric acid group, a monophosphoric acid ester group, and a boric acid.
- examples of the "monovalent organic group having a nitrogen- containing basic group” include a monovalent organic group having an amino group (-NH 2 ), a monovalent organic group having a substituted imino group (-NHR 8 , -NR 9 R 10 ) (wherein R 8 , R 9 , and R 10 each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms), a monovalent organic group having a guanidyl group represented by the following formula (al) (wherein, in formula (al), R al and R a2 each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms), and a monovalent organic group having an amidinyl group represented by the following formula (a2) (wherein, in formula (a2), R a3
- Examples of the "monovalent organic group having a urea group” include -NHCONHR 15 (wherein R 15 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms), and the like.
- Examples of the "monovalent organic group having a urethane group” include -NHCOOR 16 , -OCONHR 17 (wherein R 16 and R 17 each independently represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms), and the like.
- Examples of the "monovalent organic group having 'a group having a coordinating oxygen atom'" include a group having an acetylacetonato group, a group having crown ether, and the like.
- Examples of the "monovalent organic group having a hydrocarbon group having 4 or more carbon atoms” include an alkyl group having 4 or more carbon atoms (e.g., octyl, dodecyl), an aryl group having 6 or more carbon atoms (e.g., phenyl, naphthyl), an aralkyl group having 7 or more carbon atoms (e.g., benzyl), and the like.
- the carbon atoms of these groups there is no specific upper limit; it is, however, preferred that the number of carbon atoms is 30 or less.
- Examples of the "monovalent organic group having an alkoxy silyl group” include a group having a trimethoxy silyl group or triethoxy silyl group.
- Examples of the "monovalent organic group having an epoxy group” include a group having a glycidyl group.
- Examples of the "monovalent organic group having an isocyanate group” include a 3- isocyanatopropyl group.
- Examples of the "monovalent organic group having a hydroxyl group” include a 3- hydroxypropyl group.
- a 1 preferred is a monovalent organic group having any one of an acidic group, a nitrogen-containing basic group, a urea group, and a hydrocarbon group having 4 or more carbon atoms.
- organic dye structure or heterocycle is not particularly limited.
- examples of the organic dye structure include phthalocyanine compounds, insoluble azo compounds, azo lake compounds, anthraquinone compounds, quinacridone compounds, dioxazine compounds, diketopyrrolopyrrole compounds, anthrapyridine compounds, anthanthrone compounds, indanthrone compounds, flavanthrone compounds, perynone compounds, perylene compounds, and thioindigo compounds.
- heterocycle examples include thiophene, furan, xanthene, pyrrole, pyrroline, pyrrolidine, dioxolan, pyrazole, pyrazoline, pyrazolidine, imidazole, oxazole, thiazole, oxadiazole, triazole, thiadiazole, pyran, pyridine, piperidine, dioxane, morpholine, pyridazine, pyrimidine, piperazine, triazine, trithiane, isoindoline, isoindolinone, benzimidazolone, succinimide, phthalimide, naphthalimide, hydantoin, indole, quinoline, carbazole, acridine, acridone, and anthraquinone. [0178]
- the above-described organic dye structure or heterocycle may have a substituent T.
- substituent T include an alkyl group having 1 to 20 carbon atoms (e.g., methyl, ethyl), an aryl group having 6 to 16 carbon atoms (e.g., phenyl, naphthyl), an acyloxy group having 1 to 6 carbon atoms (e.g., acetoxy), an alkoxy group having 1 to 6 carbon atoms (e.g., methoxy, ethoxy), a halogen atom (e.g., chlorine, bromine), an alkoxycarbonyl group having 2 to 7 carbon atoms (e.g., methoxycarbonyl, ethoxycarbonyl, cyclohexyloxycarbonyl), a cyano group, a carbonic acid ester group (e.g., t-butylcarbonate), a hydroxyl group, an amino group, a carboxyl group, a
- B 1 represents a group selected from the group consisting of an acidic group, a nitrogen-containing basic group, a urea group, a urethane group, a group having a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxy silyl group, an epoxy group, an isocyanate group, and a hydroxyl group, or represents an organic dye structure or heterocycle each of which may further be substituted.
- R 18 represents a single bond, or (al + l)-valent organic or inorganic connecting group, al represents 1 to 5.
- al in the case where al is two or more, plural B 1 S may be the same or different.
- R 18 represents a single bond, or a (al+l)-valent connecting group, al represents 1 to 5.
- Examples of the connecting group represented by R 18 include those formed from atoms consisting of from 1 to 100 carbon atoms, from 0 to 10 nitrogen atoms, from 0 to 50 oxygen atoms, from 1 to 200 hydrogen atoms, and from 0 to 20 sulfur atoms, which groups may be unsubstituted or substituted with a substituent.
- R 18 is preferably an organic connecting group.
- R 18 include structural units set forth below, or a group consisted of a combination of said structural units.
- the connecting group R 18 may have the aforementioned substituent T.
- R 1 represents a (m+n)-valent connecting group, m+n is within the range of 3 to 10.
- Examples of the (m+n)-valent connecting group represented by R 1 include those groups formed from atoms consisting of from 1 to 100 carbon atoms, from 0 to 10 nitrogen atoms, from 0 to 50 oxygen atoms, from 1 to 200 hydrogen atoms, and from 0 to 20 sulfur atoms, which groups may be unsubstituted or substituted with a substituent.
- R 1 is preferably an organic connecting group.
- R 1 examples include the above-described groups of (M) to (t-34) or a group (which may have a ring structure) consisted of a combination of a plurality of said groups.
- substituents include the above-described substituent T.
- R 2 represents a single bond or a divalent connecting group.
- R 2 include groups formed from atoms consisting of from 1 to 100 carbon atoms, from 0 to 10 nitrogen atoms, from 0 to 50 oxygen atoms, from 1 to 200 hydrogen atoms, and from 0 to 20 sulfur atoms, which groups may be unsubstituted or substituted with a substituent.
- Specific examples of R 2 include the above-described groups of t-3 to t-5, t-7 to t-18, t-22 to t-26, t-32 and t-34, or a group consisted of a combination of a plurality of said groups. It is preferred that R 2 have a sulfur atom at the position where said R 2 connect to R 1 .
- examples of said substituent include the above-described substituent T.
- m represents 1 to 8.
- m is preferably 1 to 5, more preferably 1 to 3, and particularly preferably 1 to 2.
- n represents 2 to 9.
- n is preferably 2 to 8, more preferably 2 to 7, and particularly preferably 3 to 6.
- P 1 represents a polymer skeleton.
- Such the polymer skeleton can be properly selected from ordinary polymers.
- polymers or copolymers derived from a vinyl monomer ester compound polymers, ether compound polymers, urethane compound polymers, amide compound polymers, epoxy compound polymers, silicone compound polymers, and modified compounds or copolymers of these polymers (e.g.
- these polymers are soluble in an organic solvent. If the polymer has a low affinity with the organic solvent, affinity of the polymer with a dispersing medium becomes weak in the case where said polymer is used, for example, as a pigment dispersing agent. Consequently, it becomes sometimes difficult to secure an adsorption layer enough for dispersion stabilization. It is preferred that P 1 have a sulfur atom at the position where said P 1 connect to R 1 . [0190]
- a 2 has the same meaning as A 1 in the above-described formula (1). Specific and preferable embodiments of A 2 are the same as those of A 1 .
- a 2 may have a substituent with examples thereof including the above-described substituent T.
- R 3 represents a (x+y)-valent connecting group.
- R J has the same meaning as R 1 .
- the preferable range of R 3 is the same as that of R 1 .
- the value of said x and its preferable range are the same as those of n in formula (1).
- the value of said y and its preferable range are the same as those of m; the value of said x+y and its preferable range are the same as those of m+n.
- the connecting group represented by R 3 is preferably an organic connecting group. Preferred specific examples of the organic connecting groups are set forth below. However, the present invention is not limited to these.
- R 4 and R 5 each independently represent a single bond or a divalent connecting group.
- divalent connecting group represented by the above-described R 4 and R 5
- preferred are an optionally substituted, straight chain, branched, or cyclic alkylene, arylene, or aralkylene group, or -O-, -S-, -C( O)-, -N(R 19 )-, -SO-, -SO 2 -, -CO 2 -, or -N(R 20 )SO 2 -, or a divalent group formed by combining two or more of these groups (wherein R 19 and R 20 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).
- the above-described divalent connecting group is preferably an organic connecting group. [0200]
- P 2 in formula (2) represents a polymer compound residue (a polymer skeleton) and can be properly selected from ordinary polymers.
- Preferred embodiments of the polymers are the same as P 1 in above-described formula (1) and a preferred embodiment thereof is also the same as P 1 .
- R 3 is the above-described specific group of (r-1), (r-2), (r-10), (r-1 1), (r- 16), or (r-17);
- R 5 is a single bond, an ethylene group, a propylene group, or a connecting group represented by formula (s- a) or (s-b) set forth below;
- P 2 is a homopolymer or copolymer derived from a vinyl monomer, an ester compound polymer, an ether compound polymer, a urethane compound polymer, or a modified compound of these polymers;
- y is 1 to 2;
- the weight-average molecular weight of the above-described polymer compound is at least 1,000, preferably from 3,000 to 100,000, more preferably from 5,000 to 80,000, and especially preferably from 7,000 to 60,000. If the weight-average molecular weight is within the above-described range, a plurality of functional groups introduced to the terminal(s) of the polymer fully exhibit their effects, and thus the polymer compound will exhibit excellent performances in terms of adsorption properties onto a solid surface, micelle-forming property, and surface activating property. Thereby, good dispersibility and dispersion stability can be attained. [0207]
- polymer compound having a weight-average molecular weight of at least 1,000 it is possible to use any of the following polymer compounds having an acidic group (hereinafter, this compound is also referred to as an "acidic-group-containing polymer compound")-
- this compound is also referred to as an "acidic-group-containing polymer compound"
- the polymer compound preferred is a polymer compound having a carboxyl group. More preferred are copolymer compounds containing (A) at least one repeating unit derived from a compound having a carboxyl group and (B) at least one repeating unit derived from a compound having a carboxylic acid ester group.
- the repeating unit (A) derived from a compound having a carboxyl group is preferably a repeating unit represented by the following formula (I), and more preferably a repeating unit derived from acrylic acid or methacrylic acid; and the repeating unit (B) derived from a compound having a carboxylic acid ester group is preferably a repeating unit represented by the following formula (II), more preferably a repeating unit represented by the following formula (IV), and particularly preferably a repeating unit derived from benzyl acrylate, benzyl methacrylate, phenethyl acrylate, phenethyl methacrylate, 3- phenylpropyl acrylate, or 3-phenylpropyl methacrylate. [0227]
- R. 2 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
- R 3 represents a group represented by the following formula (III).
- R 4 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxy group, a hydroxyalkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms; R 5 and R 6 each represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; and i represents a number of 1 to 5.
- R. 7 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
- Rg represents a group represented by the following formula (V).
- R 9 represents an alkyl group having 2 to 5 carbon atoms or an aryl group having 6 to 20 carbon atoms.
- R 10 and R 1 each represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, j represents a number of 1 to 5.
- a ratio (%) of the number of the repeating units (A) to the total number of repeating units is preferably 3 to 40, and more preferably 5 to 35.
- the term "molecular weight" of a polymer means a number average molecular weight, unless otherwise stated.
- a method of measuring the molecular weight of polymer include a chromatography method, a viscosity method, a light scattering method, and a sedimentation velocity method.
- a number-average molecular weight calculated in terms of polystyrene, measured by gel permeation chromatography (carrier: tetrahydrofuran) is used, unless otherwise specifically indicated.
- the polymer compound may be either water-soluble or oil-soluble, or may be water-soluble and oil-soluble.
- the polymer compound may be added in a state of being dissolved in an aqueous solvent or an organic solvent, or may be added in a solid state. In addition, such addition methods may be combined.
- Examples of a method of adding the polymer compound in a state of being dissolved in a solvent include: a method involving adding, to an aggregated organic particles liquid, the polymer compound in a state of being dissolved in the same solvent as that of the aggregated organic particles liquid; and a method involving adding, to the aggregated organic particles liquid, the polymer compound in a state of being dissolved in a different solvent that is compatible with the solvent of the aggregated organic particles liquid.
- the concentration of the polymer compound is not particularly limited, but the concentration is preferably 1 to 70 mass%, more preferably 2 to 65 mass%, and particularly preferably 3 to 60 mass%.
- the polymer compound may be added at the time of or before or after the deposition and formation of the pigment fine particles, may be added at the time of or before or after concentration, may be added at the time of or before or after the dispersion of the aggregated organic particles after being subjected to concentration, or may be added after the completion of these steps.
- the polymer compound may be added in plural times by dividing the whole amount thereof into plural portions.
- the above-described polymer compound having a weight-average molecular weight of 1,000 or more may be incorporated in a composition as the aforementioned binder.
- the polymer compound is added at the time of fining and dispersing the aggregated organic particles obtained after concentration of a pigment fine particles-depositing solution.
- the polymer compound is added in an amount of preferably 0.1 to 1,000 parts by mass, more preferably 5 to 500 parts by mass, and particularly preferably 10 to 300 parts by mass, when the amount of pigment fine particles is set to 100 parts by mass.
- polymer compound examples include, other than the aforementioned compounds, polyvinyl pyrrolidone, polyvinyl alcohol, polyvinyl methyl ether, polyethylene oxide, polyethylene glycol, polypropylene glycol, polyacrylamide, vinyl alcohol/vinyl acetate copolymer, partial-formal products of polyvinyl alcohol, partial-butyral products of polyvinyl alcohol, vinylpyrrolidone/vinyl acetate copolymer, polyethylene oxide/propylene oxide block copolymer, polyamides, cellulose derivatives, and starch derivatives.
- natural polymer compounds can also be used, examples of which include alginic acid salts, gelatin, albumin, casein, gum arabic, tragacanth gum, and ligninsulfonic acid salts.
- polymer compound having an acidic group examples include polyvinyl sulfuric acid and concentrated naphthalenesulfonic acid.
- Examples of the polymer compound having a carboxyl group include polyacrylic acid, polymethacrylic acid, and a cellulose derivative having a carboxyl group in any one of its side chains.
- Examples of the copolymer containing at least one repeating unit (A) derived from a compound having a carboxyl group and at least one repeating unit (B) derived from a compound having a carboxylic acid ester group include a methacrylic acid copolymer, an acrylic acid copolymer, an itaconic acid copolymer, a crotonic acid copolymer, a maleic acid copolymer, and a partially-esterified maleic acid copolymer, as described in JP-A-59-44615, JP-B-54-34327, JP-B-58- 12577, JP-B-54-25957, JP-A-59-53836, and JP-A- 59-71048.
- copolymer examples include an acrylic acid/acrylate copolymer, a methacrylic acid/acrylate copolymer, an acrylic acid/methacrylate copolymer, a methacrylic acid/methacrylate copolymer, and a multiple-component copolymer containing acrylic acid or methacrylic acid, and an acrylate or methacrylate, and any other vinyl compound, as described in U.S. Patent No. 4,139,391.
- vinyl compound examples include styrene or a substituted styrene (such as vinyltoluene or vinyl ethyl benzene); vinylnaphthalene or a substituted vinylnaphthalene; acrylamide; methacrylamide; acrylonitrile; and methacrylonitrile. Of those, styrene is preferable.
- the polymer compound having a weight average molecular weight of 1,000 or more may be used singly or in combination of two or more thereof, or may be used in combination with a compound having a molecular weight of less than 1 ,000.
- the dispersion of the pigment fine particles include an organic solvent in an amount of preferably 60 mass% or more, and more preferably 65 mass% or more.
- the organic solvent is not particularly limited, and can be appropriately selected from common solvents.
- a preferable solvent include ester compound solvents, alcohol compound solvents, aromatic compound solvents, aliphatic compound solvents, and ketone compound solvents. Of those, ester compound solvents and ketone compound solvents are particularly preferable. Those solvents may be used singly or in combination of two or more thereof.
- ester compound solvents examples include 2-(l-methoxy)propyl acetate, ethyl acetate, ethyl lactate, and the like.
- alcohol compound solvents examples include n-butanol, isobutanol, and the like.
- aromatic compound solvents examples include benzene, toluene, xylene, and the like.
- Examples of the aliphatic compound solvents include n-hexane, cyclohexane, and the like.
- Examples of the ketone compound solvents include methylethylketone, acetone, cyclohexanone, and the like.
- the aforementioned pigment fine particles can be used, for example, in a state dispersed in a vehicle.
- the vehicle means a portion of a medium in which a pigment is dispersed when the paint is in a liquid state.
- the vehicle is a liquid state and contains a portion (binder) that is to be bonded to the pigment to solidify a coating film and a component (organic solvent) for dissolving and diluting the portion.
- a binder to be used at the time of the formation of the nanoparticles and a binder to be used in redispersing may be identical to or different from each other, and they are sometimes separately referred to as a nanoparticle formation binder and a redispersion binder, respectively.
- the concentration of pigment fine particles in a dispersion composition of the pigment fine particles after re-dispersion can be properly determined in accordance with a purpose of their use.
- the concentration of the pigment fine particles is preferably in the range of from 2 to 30 mass%, more preferably in the range of from 4 to 20 mass%, and especially preferably in the range of from 5 to 15 mass%, based on the total amount of the dispersion composition.
- amounts of the binder and the dissolution and dilution component can be properly determined depending on, for example, the kind of the organic pigment.
- the amount of the binder is preferably in the range of from 1 to 30 mass%, more preferably in the range of from 3 to 20 mass%, and especially preferably in the range of from 5 to 15 mass%, based on the total amount of the dispersion composition.
- the amount of the dissolution and dilution component is preferably in the range of from 5 to 80 mass%, and more preferably in the range of from 10 to 70 mass%, based on the total amount of the dispersion composition.
- Examples of a method that can be employed for fining and dispersing such aggregated nanoparticles include a dispersing method with using a supersonic wave and a method involving applying physical energy.
- Apparatus for ultrasonic wave irradiation is preferably an apparatus that is capable of applying an ultrasonic wave at 10 kHz or more, and examples thereof include an ultrasonic wave homogenizer, an ultrasonic wave cleaning machine, and the like.
- the liquid temperature during ultrasonic wave irradiation is preferably kept at 1 to 100 °C, more preferably 5 to 60 0 C, since increase in the liquid temperature leads to thermal aggregation of nanoparticles (see "Current Pigment Dispersion Technology", Technical Information Institute Co., Ltd., 1995, p.166).
- the temperature can be controlled, for example, by adjusting the temperature of dispersion, by adjusting the temperature of a temperature-controlling layer for controlling of dispersion temperature, or the like.
- a dispersion machine to be used at the time of dispersing the concentrated pigment fine particles by the application of physical energy is not particularly limited, and examples of the dispersion machine include a kneader, a roll mill, an attritor, a super mill, a dissolver, a homomixer, and a sand mill. Further, a high pressure dispersion method and a dispersion method of using fine particle beads are also exemplified as a preferable method.
- the above-described production method it is possible, for example, to concentrate and re- disperse the pigment fine particles to be contained in each of the pigment fine particle dispersion composition and colored photosensitive resin composition, irrespective of their minute particle diameters as small as a nanometer size (for example, 10 to 100 run). Accordingly, use of either of the compositions in a color filter can obtain a color filter which exhibits a high optical density, is excellent in uniformity of the filter surface, gives a high contrast, and has reduced image noise. Further, the pigment fine particles to be contained in the pigment fine particle dispersion composition or colored photosensitive composition can be dispersed in fine-particle states of being highly and uniformly reduced in size.
- each of the compositions exerts a high coloring density even with a small thickness, thereby enabling a reduction in thickness of, for example, a color filter.
- each of the pigment fine particle dispersion composition and colored photosensitive resin composition can be advantageously used as an image forming material for producing, for example, a color proof or a color filter, when a pigment showing a clear color tone and high coloring power is incorporated into each of the compositions.
- each of the pigment fine particle dispersion composition and colored photosensitive resin composition can use a binder which is soluble in an alkaline aqueous solution in order to get along with an alkaline developer for use in exposure and development at the time of the formation of a colored image, thus each of the compositions can meet the need for environment protection.
- an organic solvent having a suitable drying property can be used as a solvent (a dispersion medium for a pigment) for use in each of the pigment fine particle dispersion composition and colored photosensitive resin composition, and the resultant compositions can satisfy the need in drying after coating the compositions.
- the color filter of the present invention has a high contrast and an excellent hue, and it is also suitable for a continuous mass production on an industrial scale. When applied to a liquid crystal display device or a CCD device, the color filter of the present invention can exhibit excellent display characteristics.
- the whole quantity of the pigment solution was injected at a current velocity of 100 ml/min, using a non-pulsating current pump, to the above-described poor solvent controlled to a temperature of 18 0C and agitated with a four-blade propeller at 500 rpm, thereby to prepare a pigment particle dispersion having a pigment concentration of 0.1 mass%.
- the thus-prepared pigment dispersion was subjected to filtration under reduced pressure using a PTFE membrane filter and then washed, followed by concentration up to a pigment concentration of 20 mass%. By a measurement with electron microscope, it was found that the average particle diameter of the pigment particles was 22 nm.
- R pigment dispersion 1-1 was prepared with the composition described in Table 1.
- the high molecular dispersing agent 1 was one produced by random copolymerization of benzyl methacrylate and methacrylic acid in a molar ratio of 60/40.
- the number-average molecular weight (Mn) thereof was 32,000 in measurement according to a gel permeation chromatography.
- the compound Jl set forth below was used as the dispersing agent A.
- a colored photosensitive resin composition Rl-I was prepared according to the composition described in Table 2.
- a color filter 1-1 provided with a black matrix, R pixel, G pixel, and B pixel was prepared as described below.
- a non-alkali glass substrate was washed using a UV washing machine, and thereafter washed with a brush using a detergent, and then further subjected to ultrasonic cleaning with ultra pure water.
- the substrate was subjected to a thermal processing at 120 0 C for 3 minutes, thereby to stabilize the surface state of the substrate.
- the substrate was cooled and temperature controlled to 23 0 C.
- a colored photosensitive resin composition Kl having the composition described in the following Table 3 was coated with a slit nozzle-equipped coater for a glass substrate (manufactured by F.A.S. Japan Corp., trade name:
- the substrate and a mask (silica exposure mask having an image pattern) were stood vertically, and in this state, the distance between the exposure mask surface and the photosensitive resin layer was set to 200 ⁇ m; and then, a pattern exposure was conducted in an exposure amount of 300 mJ/cm 2 .
- the surface of the photosensitive resin layer Kl was uniformly wetted by splaying pure water with a shower nozzle. Thereafter, the photosensitive resin layer was shower developed under conditions of flat nozzle pressure of 0.04 MPa with a KOH-series developer (developer containing KOH and a nonionic surfactant; trade name: CDK-I; manufactured by Fuji Film Electronics Materials) at 23 0 C for 80 seconds. Thereby, a patterned image was obtained. Subsequently, ultra pure water was sprayed at a pressure of 9.8 MPa using an ultra-high-pressure cleaning nozzle, to eliminate a residue. Thus, a black (K) image K was obtained. Subsequently, the image was subjected to a thermal processing at 220 0 C for 30 minutes. [0256]
- the above-described colored photosensitive resin composition K was prepared as follows: First, carbon black and propylene glycol mono methyl ether acetate were weighed, and then they were mixed at a temperature of 24 0 C ( ⁇ 2 0 C) and stirred at 150 rpm for 10 minutes. Thereafter, methyl ethyl ketone, the binder, hydroquinone mono methyl ether, the DPHA solution, the polymerization initiator A, and the surfactant were weighed, and they were added in this order at a temperature of 25 °C ( ⁇ 2 0 C), and then the resultant mixture was stirred at 150 rpm at 40 0 C ( ⁇ 2 0 C) for 30 minutes. [0257] ⁇ Formation of red (R) pixel>
- a thermally treated pixel R was formed using the above-described colored photosensitive resin composition Rl-I in the same steps as formation of the black (K) image.
- the film thickness of the thus-obtained photosensitive resin layer R and the coating amount of the pigment were shown below.
- the colored photosensitive resin composition Rl-I was prepared in the same manner as the above-described colored photosensitive resin composition K. Film thickness of photosensitive resin ( ⁇ m) 1.60 Coating amount of pigment (g/m 2 ) 1.00
- a thermally treated pixel G was formed using the colored photosensitive resin composition G having the composition shown below Table 4 in the same steps as formation of the black (K) image.
- the film thickness of the thus-obtained photosensitive resin layer G and the coating amount of the pigment were shown below.
- the colored photosensitive resin composition G was prepared in the same manner as the above-described colored photosensitive resin composition K.
- Coating amount of pigment (g/m 2 ) 1.92
- a thermally treated pixel B was formed using the colored photosensitive resin composition Bl having the composition shown below Table 5 in the same steps as formation of the black (K) image. In this manner, the desired color filter A was obtained.
- the film thickness of the thus-obtained photosensitive resin layer Bl and the coating amount of the pigment were shown below.
- the colored photosensitive resin composition B 1 was prepared in the same manner as the above-described colored photosensitive resin composition K.
- Example 1-1 except that the amount of polyvinyl pyrrolidone used at the time of preparing the R-pigment dispersion 1-1 was changed to 20,000 mg. By a measurement with electron microscope, it was found that the average particle diameter of the pigment particles was 23 nm.
- a R-pigment dispersion 1-3, a colored photosensitive resin composition Rl-3, and a color filter 1-3 using the colored photosensitive resin composition Rl-3 were prepared in the same manner as in
- Example 1-1 except that the amount of polyvinyl pyrrolidone used at the time of preparing the R-pigment dispersion 1-1 was changed to 50,000 mg. By a measurement with electron microscope, it was found that the average particle diameter of the pigment particles was 21 nm.
- Example 1-1 except that the amount of polyvinyl pyrrolidone used at the time of preparing the R-pigment dispersion 1-1 was changed to 100,000 mg. By a measurement with electron microscope, it was found that the average particle diameter of the pigment particles was 20 nm.
- Example 2 A R-pigment dispersion 2, a colored photosensitive resin composition R2, and a color filter 2 using the colored photosensitive resin composition R2 were prepared in the same manner as in Example 1-1 , except that 50,000 mg of polyvinyl pyrrolidone K.90 (manufactured by Wako Pure Chemical Industries, Ltd.) was added in place of polyvinyl pyrrolidone K25 at the time of preparing the R-pigment dispersion 1- 1. By a measurement with electron microscope, it was found that the average particle diameter of the pigment particles was 20 nm. (Example 3)
- a pigment dispersion and a pigment condensate were prepared in the same manner as in Example 1-4, except that the temperature of the poor solvent was changed to 45 0 C. By a measurement with electron microscope, it was found that the average particle diameter of the pigment particles was 53 nm.
- a R-pigment dispersion A, a colored photosensitive resin composition RA, and a color filter A using the colored photosensitive resin composition RA were prepared in the same manner as in Example 1-
- the resultant pigment composition was dispersed with using zirconia beads of 0.5 mm in diameter, at a peripheral speed of 10 m/s, for 1 hour, using a motor mill M-50 (manufactured by Eigar Japan).
- the thus- obtained pigment dispersion was designated as R-pigment dispersion B.
- R-pigment dispersion B By a measurement with electron microscope, it was found that the average particle diameter of the pigment particles was 48 nm.
- Pigment dispersions were each subjected to evaporation to dryness at 100 °C and at atmospheric pressure. Each of the thus-obtained solids was ground. 2. Each of the ground products was made into tablets according to a KBr method to prepare samples. The amount of polyvinyl pyrrolidone in each of the samples was determined using a Fourier transform infrared spectrophotometer FTIR-8400S (trade name) manufactured by Shimadzu Corporation.
- contrast of the coated product was measured according to the following method.
- a backlight unit a three- wave length cold-cathode-tube light source (FWL18EX-N, trade name, manufactured by Toshiba Lighting & Technology Corporation) provided with a diffuser plate was used.
- Each of the color filters was placed between two sheets of polarizing plates (HLC2-2518, trade name, manufactured by Sanritz Corporation), and then amounts of transmitted light at the time when polarization axes of two polarizing plates were parallel and the time when the polarization axes were perpendicular were measured.
- the ratio of these transmitted light amounts was defined as a contrast (see Color Filter for 512 color display 10.4"-size TFT-LCD, co-authored by Ueki, Koseki, Fukunaga, and Yamanaka, The seventh Color Optics Conference (1990), etc.). Chromaticity was measured using a color luminance meter (BM-5 (trade name), manufactured by Topcon Techno House Corporation).
- BM-5 color luminance meter
- the above-described two sheets of polarizing plates, color filter, and color luminance meter were placed at the following positions: A polarizing plate was disposed at the distance of 13 mm from the backlight. A cylinder of 1 1 mm in diameter and 20 mm in length was disposed at the distance of 40 mm to 60 mm from the backlight.
- the light transmitted through the cylinder was irradiated to a color filter disposed at the distance of 65 mm from the backlight.
- the transmitted light was passed through another polarizing plate disposed at the distance of 100 mm from the backlight and measured with a color luminance meter disposed at the distance of 400 mm from the backlight.
- the measuring angle in the color luminance meter was set to 2°.
- the light amount of the backlight was set so that its brightness (luminance) would be 1280 cd/m", when the two sheets of polarizing plates were arranged in a position of parallel nicol and no color filter was disposed.
- the color filter 3 showed a relatively lower contrast though it contained the water-soluble polymer. It is assumed that this result can be attributed to the fact that the pigment particles contained in the color filter 3 had a diameter as large as about 50 nm. In this connection, the color filter 3 exhibited superior contrast to the color filter B, though they included pigment particles almost identical in their particle diameter, showing an effect attributable to inclusion of the water-soluble polymer.
- ITO indium tin oxide
- a protrusion for controlling orientation of liquid crystal was formed on the ITO transparent electrode formed with the above-described spacer.
- a proximity-type exposure equipment (manufactured by Hitachi High-Tech Electronics Engineering Co., Ltd.) was set so that a certain photo mask would be located at the distance of 100 ⁇ m from the surface of the photosensitive resin layer.
- a proximity exposure was carried out through the said photo mask in an exposure amount of 150 mJ/cm 2 using an ultra-high pressure mercury lamp.
- An alignment film composed of polyimide was further provided on the thus-obtained substrate for a liquid crystal display device. Thereafter, a sealing agent made of an epoxy resin was printed at the positions corresponding to the outer frame of the black matrix that was disposed so as to surround the periphery of the pixels of the color filter.
- a liquid crystal for MVA- mode After dropping thereon a liquid crystal for MVA- mode, the above-described substrate and a counter substrate were stuck together. The stuck substrates were subjected to a thermal processing to cure the sealing agent.
- a polarizing plate HLC2-2518 manufactured by Sanritz Corporation was stuck together.
- liquid crystal display device 1-1 the liquid crystal display device provided with the color filter 1-1 was designated as liquid crystal display device 1-1.
- liquid crystal display devices 1-2 to 1-4, 2, 3, A, and B were produced, respectively.
- Image quality of each liquid crystal display device was evaluated as follows.
- a liquid crystal display device exhibiting the total score of 25 or more has sufficient properties for practical use.
- the color filter of the present invention has a high contrast and an excellent hue, and it is suitable for a continuous mass production on an industrial scale. When applied to a liquid crystal display device or a CCD device, the color filter of the present invention can exhibit excellent display characteristics. [0289]
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Abstract
Description
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JP (1) | JP2010509619A (en) |
KR (1) | KR20090081370A (en) |
CN (1) | CN101535849B (en) |
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WO (1) | WO2008056819A1 (en) |
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JP5446170B2 (en) * | 2008-08-27 | 2014-03-19 | 凸版印刷株式会社 | Red coloring composition, color filter and liquid crystal display device |
JP7196392B2 (en) * | 2017-11-10 | 2022-12-27 | Dic株式会社 | Inkjet ink for color filter, light conversion layer and color filter |
Citations (6)
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JP2002194244A (en) * | 2000-12-25 | 2002-07-10 | Fuji Photo Film Co Ltd | Pigment dispersion composition, coloring photosensitive composition obtained by using the same and color filter |
JP2002328215A (en) * | 2001-04-26 | 2002-11-15 | Fuji Photo Film Co Ltd | Photosensitive color composition |
JP2003336001A (en) * | 2002-05-21 | 2003-11-28 | Canon Inc | Organic pigment dispersion and method for manufacturing the same, aqueous coloring fluid and inkjet recording ink |
JP2004091560A (en) * | 2002-08-30 | 2004-03-25 | Japan Science & Technology Corp | New method for producing pigment nanoparticle |
JP2004211095A (en) * | 2002-12-31 | 2004-07-29 | Ind Technol Res Inst | Inkjet ink composition of photo-curing pigment type |
JP2005181383A (en) * | 2003-12-16 | 2005-07-07 | Toyo Ink Mfg Co Ltd | Blue coloring composition for color filter and color filter |
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CN1089168C (en) * | 1998-06-19 | 2002-08-14 | 清华大学 | Method for preparing color filter for color display |
KR101057248B1 (en) * | 2003-01-30 | 2011-08-16 | 신닛테츠가가쿠 가부시키가이샤 | Pigment dispersions, compositions for color filters and color filters |
EP1731576B1 (en) * | 2005-02-22 | 2010-05-12 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Diketopyrrolopyrrole Pigment dispersants and their use |
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2007
- 2007-11-07 WO PCT/JP2007/072059 patent/WO2008056819A1/en active Application Filing
- 2007-11-07 JP JP2009535194A patent/JP2010509619A/en active Pending
- 2007-11-07 CN CN2007800416886A patent/CN101535849B/en not_active Expired - Fee Related
- 2007-11-07 KR KR1020097006686A patent/KR20090081370A/en not_active Application Discontinuation
- 2007-11-08 TW TW096142159A patent/TWI409505B/en not_active IP Right Cessation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002194244A (en) * | 2000-12-25 | 2002-07-10 | Fuji Photo Film Co Ltd | Pigment dispersion composition, coloring photosensitive composition obtained by using the same and color filter |
JP2002328215A (en) * | 2001-04-26 | 2002-11-15 | Fuji Photo Film Co Ltd | Photosensitive color composition |
JP2003336001A (en) * | 2002-05-21 | 2003-11-28 | Canon Inc | Organic pigment dispersion and method for manufacturing the same, aqueous coloring fluid and inkjet recording ink |
JP2004091560A (en) * | 2002-08-30 | 2004-03-25 | Japan Science & Technology Corp | New method for producing pigment nanoparticle |
JP2004211095A (en) * | 2002-12-31 | 2004-07-29 | Ind Technol Res Inst | Inkjet ink composition of photo-curing pigment type |
JP2005181383A (en) * | 2003-12-16 | 2005-07-07 | Toyo Ink Mfg Co Ltd | Blue coloring composition for color filter and color filter |
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CN101535849B (en) | 2011-11-23 |
CN101535849A (en) | 2009-09-16 |
JP2010509619A (en) | 2010-03-25 |
TW200831956A (en) | 2008-08-01 |
TWI409505B (en) | 2013-09-21 |
KR20090081370A (en) | 2009-07-28 |
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