CN111758051B - 绿色着色树脂组合物 - Google Patents
绿色着色树脂组合物 Download PDFInfo
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- CN111758051B CN111758051B CN201980014501.6A CN201980014501A CN111758051B CN 111758051 B CN111758051 B CN 111758051B CN 201980014501 A CN201980014501 A CN 201980014501A CN 111758051 B CN111758051 B CN 111758051B
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- 239000011347 resin Substances 0.000 claims abstract description 75
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- 239000002904 solvent Substances 0.000 claims abstract description 50
- 239000003086 colorant Substances 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 8
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- 239000000975 dye Substances 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 229930195734 saturated hydrocarbon Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000001043 yellow dye Substances 0.000 claims description 11
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- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
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- 238000009826 distribution Methods 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 2
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- 125000002619 bicyclic group Chemical group 0.000 description 1
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ILUAAIDVFMVTAU-UHFFFAOYSA-N cyclohex-4-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC=CCC1C(O)=O ILUAAIDVFMVTAU-UHFFFAOYSA-N 0.000 description 1
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- KAAQPMPUQHKLLE-UHFFFAOYSA-N cyclohexene-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)=CC1 KAAQPMPUQHKLLE-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
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- UJKTWIYIDOPXOI-UHFFFAOYSA-L disodium 2-carboxy-4-[[4-[4-[(3-carboxy-4-oxidophenyl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]phenolate Chemical compound [Na+].[Na+].CC1=CC(=CC=C1N=NC1=CC(C([O-])=O)=C(O)C=C1)C1=CC=C(N=NC2=CC=C(O)C(=C2)C([O-])=O)C(C)=C1 UJKTWIYIDOPXOI-UHFFFAOYSA-L 0.000 description 1
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- 238000005530 etching Methods 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
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- 238000002474 experimental method Methods 0.000 description 1
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- 230000014509 gene expression Effects 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
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- AKWHOGIYEOZALP-UHFFFAOYSA-N methyl 2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC AKWHOGIYEOZALP-UHFFFAOYSA-N 0.000 description 1
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- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000001053 orange pigment Substances 0.000 description 1
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- PBHPFFDRTUWVIT-UHFFFAOYSA-N oxetan-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CCO1 PBHPFFDRTUWVIT-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
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/007—Squaraine dyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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Abstract
Description
技术领域
本发明涉及绿色着色树脂组合物,也涉及由该绿色着色树脂组合物形成的滤色器。
背景技术
现有技术文献
专利文献
专利文献1:日本特开2015-86379号公报
发明内容
本发明提供以下的[1]~[4]。
[1]一种绿色着色树脂组合物,含有着色剂、树脂和溶剂,
相对于从所述绿色着色树脂组合物的总量除去所述着色剂和所述溶剂的含量而得的量,所述树脂的含有率为70质量%以上。
[式(II)中,R1~R4各自独立地表示氢原子、卤素原子、羟基或碳原子数1~20的1价的饱和烃基。该1价的饱和烃基中所含的氢原子或甲基可以被取代成卤素原子、羟基或碳原子数1~8的烷基氨基,可以在构成该1价的饱和烃基的碳原子间***氧原子或硫原子。
R5~R8相互独立地表示氢原子或羟基。
Ar1和Ar2各自独立地表示下式(i)所示的基团。
式(i)中,R12表示碳原子数1~20的1价的饱和烃基或碳原子数2~20的1价的不饱和烃基,m表示1~5的整数。m为2以上时,多个R12可以分别相同也可以不同。*表示与氮原子的键合位点。
R9和R10各自独立地表示碳原子数1~20的1价的饱和烃基或式(i)所示的基团。该1价的饱和烃基中所含的氢原子或甲基可以被取代成卤素原子、羟基、或者被1个或2个碳原子数1~8的烷基取代的氨基,可以在构成该1价的饱和烃基的碳原子间***氧原子或硫原子]
[4]一种滤色器,由[1]~[3]中任一项所述的绿色着色树脂组合物形成。
本发明的绿色着色树脂组合物的耐热性优异。
具体实施方式
本发明的着色树脂组合物含有着色剂(A)、树脂(B)和溶剂(E)。本发明的着色树脂组合物也可以根据需要含有流平剂(F)、填充剂、其它高分子化合物、密合促进剂、抗氧化剂、光稳定剂、链转移剂等该技术领域中公知的添加剂。本发明的着色树脂组合物含有方酸染料作为着色剂(A),优选为绿色着色树脂组合物。以下,对各成分的详细情况进行说明。在本说明书中,只要没有特别说明,则作为各成分而例示的化合物可以单独或组合使用多种。
<着色剂(A)>
(染料(A-1))
式(I)中,A和A’各自独立地表示含有芳香族环或杂环的有机基团。式(I)所示的化合物中也包含具有关于式(I)所示的结构有可能性的所有共振结构的化合物。
式(II)中,R1~R4各自独立地表示氢原子、卤素原子、羟基或碳原子数1~20的1价的饱和烃基。该1价的饱和烃基中所含的氢原子或甲基可以被取代成卤素原子、羟基或碳原子数1~8的烷基氨基,可以在构成该1价的饱和烃基的碳原子间***氧原子或硫原子。
R5~R8相互独立地表示氢原子或羟基。
Ar1和Ar2各自独立地表示下式(i)所示的基团。
式(i)中,R12表示碳原子数1~20的1价的饱和烃基或碳原子数2~20的1价的不饱和烃基,m表示1~5的整数。m为2以上时,多个R12可以分别相同也可以不同。*表示与氮原子的键合位点。
R9和R10各自独立地表示碳原子数1~20的1价的饱和烃基或式(i)所示的基团。该1价的饱和烃基中所含的氢原子或甲基可以被取代成卤素原子、羟基、或者被1个或2个碳原子数1~8的烷基取代的氨基,可以在构成该一价饱和烃基的碳原子间***氧原子或硫原子。
式(II)中,作为R1~R4中的卤素原子,可举出氟原子、氯原子、溴原子或碘原子。
作为R1~R4、R9、R10和R12中的碳原子数1~20的1价的饱和烃基,例如可举出甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基、十六烷基和二十烷基等碳原子数1~20的直链状烷基;异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基和2-乙基己基等碳原子数3~20的支链状烷基;环丙基、环戊基、环己基、环庚基、环辛基和三环癸基等碳原子数3~20的脂环式饱和烃基。
作为这些饱和烃基中所含的氢原子或甲基被取代成卤素原子、羟基或者被1个或2个碳原子数1~8的烷基取代的氨基的基团,例如可举出下述式所示的基团。在此,作为被1个或2个碳原子数1~8的烷基取代的氨基,可举出甲基氨基、乙基氨基、正丙基氨基、正丁基氨基、正戊基氨基、二甲基氨基、二乙基氨基、二丁基氨基、甲基乙基氨基等。下述式中,*表示键合位点。
作为在构成这些饱和碳基的碳原子间***氧原子或硫原子的基团,例如可举出下述式所示的基团。下述式中,*表示键合位点。
作为R12中的碳原子数2~20的1价的不饱和烃基,例如可举出乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基。
作为式(i)所示的基团,例如可举出如下所述的基团。*表示与氮原子的键合位点。
作为R1~R4,优选为氢原子、羟基和甲基,更优选为氢原子。
作为R9和R10,优选为辛基、壬基、癸基、十二烷基、2-乙基己基和式(i)所示的基团,更优选为2-乙基己基。
作为R12,优选为碳原子数1~4的烷基,更优选为甲基和乙基。
式(II)中,在将
所示的基团设为X1,将
所示的基团设为X2时,作为X1和X2所示的基团,例如可举出式(A2-1)~式(A2-7)所示的基团。*表示与碳原子的键合位点。
作为式(II)所示的化合物,例如可举出表1所示的化合物(AII-1)~化合物(AII-21)。
[表1]
化合物 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | X1 | X2 |
AII-1 | H | H | H | H | H | H | H | H | A2-1 | A2-1 |
AII-2 | H | H | H | H | H | H | H | H | A2-2 | A2-2 |
AII-3 | H | H | H | H | H | H | H | H | A2-3 | A2-3 |
AII-4 | H | H | H | H | H | H | H | H | A2-4 | A2-4 |
AII-5 | H | H | H | H | H | H | H | H | A2-5 | A2-5 |
AII-6 | H | H | H | H | H | H | H | H | A2-6 | A2-6 |
AII-7 | H | H | H | H | H | H | H | H | A2-7 | A2-7 |
AII-8 | H | H | H | H | OH | OH | H | H | A2-1 | A2-1 |
AII-9 | H | H | H | H | OH | OH | H | H | A2-2 | A2-2 |
AII-10 | H | H | H | H | OH | OH | H | H | A2-3 | A2-3 |
AII-11 | H | H | H | H | OH | OH | H | H | A2-4 | A2-4 |
AII-12 | H | H | H | H | OH | OH | H | H | A2-5 | A2-5 |
AII-13 | H | H | H | H | OH | OH | H | H | A2-6 | A2-6 |
AII-14 | H | H | H | H | OH | OH | H | H | A2-7 | A2-7 |
AII-15 | H | H | H | H | OH | OH | OH | OH | A2-1 | A2-1 |
AII-16 | H | H | H | H | OH | OH | OH | OH | A2-2 | A2-2 |
AII-17 | H | H | H | H | OH | OH | OH | OH | A2-3 | A2-3 |
AII-18 | H | H | H | H | OH | OH | OH | OH | A2-4 | A2-4 |
AII-19 | H | H | H | H | OH | OH | OH | OH | A2-5 | A2-5 |
AII-20 | H | H | H | H | OH | OH | OH | OH | A2-6 | A2-6 |
AII-21 | H | H | H | H | OH | OH | OH | OH | A2-7 | A2-7 |
从原料获得性的观点考虑,更优选化合物(AII-8)~化合物(AII-14),其中,更优选化合物(AII-8)。
本发明的化合物(II)例如可以通过日本特开2002-363434号公报记载的方法来制造,具体而言,通过使式(IV-1)所示的化合物与方酸(3,4-二羟基-3-环丁烯-1,2-二酮)反应的方法来制造。
式(IV-1)中,R1、R2、R5、R6、R9和Ar1分别表示与上述相同的含义。
方酸的使用量相对于式(IV-I)所示的化合物1摩尔优选为0.5摩尔~0.8摩尔,更优选为0.55摩尔~0.6摩尔。
反应温度优选为30~180℃,更优选为80~140℃。反应时间优选为1~12小时,更优选为3~8小时。
从收率方面考虑,反应优选在有机溶剂中进行。作为有机溶剂,可举出甲苯、二甲苯等烃溶剂;氯苯、二氯苯、氯仿等卤代烃溶剂;甲醇、乙醇、异丙醇、丁醇等醇溶剂;硝基苯等硝基烃溶剂;甲基异丁基酮等酮溶剂;1-甲基-2-吡咯烷酮等酰胺溶剂等,可以将它们混合使用。其中,优选丁醇和甲苯的混合溶剂。有机溶剂的使用量相对于式(IV-I)所示的化合物1质量份优选为30质量份~200质量份,更优选为50质量份~150质量份。
由反应混合物获得作为目标化合物的化合物(II)的方法没有特别限定,可以采用公知的各种方法。例如,可举出冷却后将析出的晶体滤出的方法。优选将滤出的晶体利用水等进行清洗,接着,进行干燥。另外,也可以根据需要通过重结晶等公知的方法进一步进行纯化。
使式(IV-2)所示的化合物与式(IV-3)所示的化合物反应而制造式(IV-4)所示的化合物后,使式(IV-4)所示的化合物与式(IV-5)所示的化合物反应,由此能够制造式(IV-I)所示的化合物。
式(IV-2)~式(IV-5)中,R1、R2、R5、R6、R9、R12和m分别表示与上述相同的含义。
作为由式(IV-2)所示的化合物和式(IV-3)所示的化合物制造式(IV-4)所示的化合物的方法,可举出公知的各种方法,例如Eur.J.Org.Chem.2012,3105-3111.中记载的方法。
作为由式(IV-4)所示的化合物和式(IV-5)所示的化合物制造式(IV-1)所示的化合物的方法,可举出公知的各种方法,例如J.Polymer Sciene Science Part A:PolymerChemistry 2012,50,3788-3796中记载的方法。
染料(A-1)的含量相对于着色剂的总量为1~100质量%,优选为3~99.9质量%。
(其它着色剂成分)
为了调色,即为了调整光谱特性,着色剂(A)除染料(A-1)以外,还可以进一步含有染料(A-1)以外的染料(以下,也有时记载为染料(A-2))、颜料(P)或它们的混合物。染料(A-2)只要为方酸染料以外的染料就没有限定,可举出油溶性染料、酸性染料、酸性染料的胺盐、酸性染料的磺酰胺衍生物等染料,例如可举出彩色索引(The Society of Dyersand Colourists出版)中被分类为染料的化合物、染色笔记(色染公司)中记载的公知的染料。另外,根据化学结构,可举出香豆素染料、含金偶氮染料、吡啶酮偶氮染料、巴比妥偶氮染料、喹酞酮染料、次甲基染料、花青染料、蒽醌染料、三苯基甲烷染料、呫吨染料和酞菁染料。这些染料可以单独使用也可以并用2种以上。
具体而言,可举出C.I.溶剂黄4(以下,省略C.I.溶剂黄的记载而仅记载编号)、14、15、23、24、38、62、63、68、82、94、98、99、162;
C.I.溶剂橙2、7、11、15、26、56等C.I.溶剂染料,
C.I.酸性黄1、3、7、9、11、17、23、25、29、34、36、38、40、42、54、65、72、73、76、79、98、99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、155、157、160、161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、212、214、220、221、228、230、232、235、238、240、242、243、251;
C.I.酸性橙6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、169、173等C.I.酸性染料,
C.I.直接黄2、33、34、35、38、39、43、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、136、138、141;
C.I.直接橙34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107等C.I.直接染料,
C.I.媒染黄5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65;
C.I.媒染橙3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48等C.I.媒染染料等。
作为染料(A-2),优选为香豆素染料、含金偶氮染料、吡啶酮偶氮染料、巴比妥偶氮染料、喹酞酮染料、次甲基染料、花青染料等黄色染料。通过含有黄色染料,能够提高制成滤色器时的亮度,因而优选。
作为黄色染料,可例示以下所示的化合物。
着色树脂组合物的着色剂(A)中含有染料(A-2)时,染料(A-2)的含量相对于着色剂的总量为3~99质量%,优选为4~98质量%。如果染料(A-2)在上述范围内,则容易调整色彩值,因而优选。另外,如果含有黄色染料作为染料(A-2)且黄色染料的含量在上述范围内,则能够提高制成滤色器时的亮度,因而优选。
作为颜料(P),没有特别限定,可以使用公知的颜料,例如可举出颜色索引(TheSociety of Dyers and Colourists出版)中被分类为颜料的颜料。
例如可举出C.I.颜料黄1、3、12、13、14、15、16、17、20、24、31、53、83、86、93、94、109、110、117、125、128、137、138、139、147、148、150、153、154、166、173、194、214等黄色颜料;
C.I.颜料橙13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等橙色颜料;
C.I.颜料绿7、36、58等绿色颜料。
作为颜料(P),优选为C.I.颜料黄1、3、12、13、14、15、16、17、20、24、31、53、83、86、93、94、109、110、117、125、128、137、138、139、147、148、150、153、154、166、173、194、214等黄色颜料;以及
C.I.颜料绿7、36、58等绿色颜料,
更优选为C.I.颜料黄150、185和C.I.颜料绿58。
着色剂(A)的含量相对于着色树脂组合物的固体成分的总量优选为0.1~60质量%,更优选为1~55质量%,进一步优选为2~50质量%。如果着色剂(A)的含量在上述范围内,则在制成滤色器时的颜色浓度充分且能够在组合物中含有必要量的树脂(B),因此,能够形成机械强度充分的滤色器。在此,本说明书中的“固体成分的总量”是指从着色树脂组合物的总量中除去溶剂的含量而得的量。固体成分的总量以及相对于该固体成分的总量的各成分的含量例如可以通过液相色谱或气相色谱等公知的分析手段进行测定。
<树脂(B)>
树脂(B)没有特别限定,优选为碱可溶性树脂。作为树脂(B),可举出以下的树脂[K1]~树脂[K6]等。
树脂[K1]:选自不饱和羧酸和不饱和羧酸酐中的至少一种(Ba)(以下也有时记载为“(Ba)”)与具有碳原子数2~4的环状醚结构和烯键式不饱和键的单体(Bb)(以下也有时记载为“(Bb)”)的共聚物;
树脂[K2]:(Ba)、(Bb)和能够与(Ba)共聚的单体(Bc)(其中,与(Ba)和(Bb)不同)(以下也有时记载为“(Bc)”)的共聚物;
树脂[K3]:(Ba)与(Bc)的共聚物;
树脂[K4]:使(Bb)和(Ba)与(Bc)的共聚物反应而得的树脂;
树脂[K5]:使(Ba)和(Bb)与(Bc)的共聚物反应而得的树脂;
树脂[K6]:使(Ba)和(Bb)与(Bc)的共聚物反应,进一步使羧酸酐反应而得的树脂。
作为(Ba),具体而言,例如可举出丙烯酸、甲基丙烯酸、巴豆酸、邻乙烯基苯甲酸、间乙烯基苯甲酸、对乙烯基苯甲酸等不饱和单羧酸类;
马来酸、富马酸、柠康酸、中康酸、衣康酸、3-乙烯基邻苯二甲酸、4-乙烯基邻苯二甲酸、3,4,5,6-四氢邻苯二甲酸、1,2,3,6-四氢邻苯二甲酸、二甲基四氢邻苯二甲酸、1,4-环己烯二羧酸等不饱和二羧酸类;
甲基-5-降冰片烯-2,3-二羧酸、5-羧基双环[2.2.1]庚-2-烯、5,6-二羧基双环[2.2.1]庚-2-烯、5-羧基-5-甲基双环[2.2.1]庚-2-烯、5-羧基-5-乙基双环[2.2.1]庚-2-烯、5-羧基-6-甲基双环[2.2.1]庚-2-烯、5-羧基-6-乙基双环[2.2.1]庚-2-烯等含有羧基的双环不饱和化合物类;
马来酸酐、柠康酸酐、衣康酸酐、3-乙烯基邻苯二甲酸酐、4-乙烯基邻苯二甲酸酐、3,4,5,6-四氢邻苯二甲酸酐、1,2,3,6-四氢邻苯二甲酸酐、二甲基四氢邻苯二甲酸酐、5,6-二羧基双环[2.2.1]庚-2-烯酐等不饱和二羧酸类酐;
琥珀酸单[2-(甲基)丙烯酰氧基乙基]酯、邻苯二甲酸单[2-(甲基)丙烯酰氧基乙基]酯等2价以上的多元羧酸的不饱和单[(甲基)丙烯酰氧基烷基]酯类;
α-(羟基甲基)丙烯酸这样的在同一分子中含有羟基和羧基的不饱和丙烯酸酯类等。
这些之中,从共聚反应性的方面、得到的树脂在碱性水溶液中的溶解性的方面考虑,优选为丙烯酸、甲基丙烯酸、马来酸酐等。
(Bb)例如是指具有碳原子数2~4的环状醚结构(例如,选自环氧乙烷环、氧杂环丁烷环和四氢呋喃环中的至少一种)和烯键式不饱和键的聚合性化合物。(Bb)优选为具有碳原子数2~4的环状醚和(甲基)丙烯酰氧基的单体。
应予说明,在本说明书中,“(甲基)丙烯酸”表示选自丙烯酸和甲基丙烯酸中的至少一种。“(甲基)丙烯酰基”和“(甲基)丙烯酸酯”等的表述也具有同样的含义。
作为(Bb),例如可举出具有环氧乙烷基和烯键式不饱和键的单体、具有氧杂环丁基和烯键式不饱和键的单体、具有四氢呋喃基和烯键式不饱和键的单体等。
作为(Bb),从能够进一步提高得到的滤色器的耐热性、耐化学药品性等可靠性的方面考虑,优选为具有环氧乙烷基和烯键式不饱和键的单体。
[作为(Bc),例如可举出(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸仲丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸环戊酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸2-甲基环己酯、(甲基)丙烯酸三环[5.2.1.02,6]癸烷-8-基酯(该技术领域中,作为惯用名,被称为“(甲基)丙烯酸二环戊基酯”。另外,有时称为“(甲基)丙烯酸三环癸酯”)、(甲基)丙烯酸三环[5.2.1.02,6]癸烯-8-基酯(该技术领域中,作为惯用名,被称为“(甲基)丙烯酸二环戊烯基酯”)、(甲基)丙烯酸二环戊基氧基乙酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸金刚烷基酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸炔丙酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸萘酯、(甲基)丙烯酸苄酯等(甲基)丙烯酸酯类;
(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯等含羟基的(甲基)丙烯酸酯类;
马来酸二乙酯、富马酸二乙酯、衣康酸二乙酯等二羧酸二酯;
双环[2.2.1]庚-2-烯、5-甲基双环[2.2.1]庚-2-烯、5-乙基双环[2.2.1]庚-2-烯、5-羟基双环[2.2.1]庚-2-烯、5-羟基甲基双环[2.2.1]庚-2-烯、5-(2’-羟基乙基)双环[2.2.1]庚-2-烯、5-甲氧基双环[2.2.1]庚-2-烯、5-乙氧基双环[2.2.1]庚-2-烯、5,6-二羟基双环[2.2.1]庚-2-烯、5,6-二(羟基甲基)双环[2.2.1]庚-2-烯、5,6-二(2’-羟基乙基)双环[2.2.1]庚-2-烯、5,6-二甲氧基双环[2.2.1]庚-2-烯、5,6-二乙氧基双环[2.2.1]庚-2-烯、5-羟基-5-甲基双环[2.2.1]庚-2-烯、5-羟基-5-乙基双环[2.2.1]庚-2-烯、5-羟基甲基-5-甲基双环[2.2.1]庚-2-烯、5-叔丁氧基羰基双环[2.2.1]庚-2-烯、5-环己基氧基羰基双环[2.2.1]庚-2-烯、5-苯氧基羰基双环[2.2.1]庚-2-烯、5,6-双(叔丁氧基羰基)双环[2.2.1]庚-2-烯、5,6-双(环己基氧基羰基)双环[2.2.1]庚-2-烯等双环不饱和化合物类;
N-苯基马来酰亚胺、N-环己基马来酰亚胺、N-苄基马来酰亚胺、N-琥珀酰亚胺基-3-马来酰亚胺苯甲酸酯、N-琥珀酰亚胺基-4-马来酰亚胺丁酸酯、N-琥珀酰亚胺基-6-马来酰亚胺己酸酯、N-琥珀酰亚胺基-3-马来酰亚胺丙酸酯、N-(9-吖啶基)马来酰亚胺等二羰基酰亚胺衍生物类;
苯乙烯、α-甲基苯乙烯、间甲基苯乙烯、对甲基苯乙烯、乙烯基甲苯、对甲氧基苯乙烯、丙烯腈、甲基丙烯腈、氯乙烯、偏二氯乙烯、丙烯酰胺、甲基丙烯酰胺、乙酸乙烯酯、1,3-丁二烯、异戊二烯、2,3-二甲基-1,3-丁二烯等。
这些之中,从共聚反应性和耐热性的方面考虑,优选为苯乙烯、乙烯基甲苯、N-苯基马来酰亚胺、N-环己基马来酰亚胺、N-苄基马来酰亚胺、双环[2.2.1]庚-2-烯等。
作为树脂(B),具体可举出(甲基)丙烯酸3,4-环氧环己基甲酯/(甲基)丙烯酸共聚物、丙烯酸3,4-环氧三环[5.2.1.02.6]癸酯/(甲基)丙烯酸共聚物等树脂[K1];(甲基)丙烯酸缩水甘油酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物、(甲基)丙烯酸缩水甘油酯/苯乙烯/(甲基)丙烯酸共聚物、丙烯酸3,4-环氧三环[5.2.1.02.6]癸酯/(甲基)丙烯酸/N-环己基马来酰亚胺共聚物、3-甲基-3-(甲基)丙烯酰氧基甲基氧杂环丁烷/(甲基)丙烯酸/苯乙烯共聚物等树脂[K2];(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物、苯乙烯/(甲基)丙烯酸共聚物等树脂[K3];对(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物加成(甲基)丙烯酸缩水甘油酯而成的树脂、对(甲基)丙烯酸三环癸酯/苯乙烯/(甲基)丙烯酸共聚物加成(甲基)丙烯酸缩水甘油酯而成的树脂、对(甲基)丙烯酸三环癸酯/(甲基)丙烯酸苄酯/(甲基)丙烯酸共聚物加成(甲基)丙烯酸缩水甘油酯而成的树脂等树脂[K4];使(甲基)丙烯酸与(甲基)丙烯酸三环癸酯/(甲基)丙烯酸缩水甘油酯的共聚物进行反应而成的树脂、使(甲基)丙烯酸与(甲基)丙烯酸三环癸酯/苯乙烯/(甲基)丙烯酸缩水甘油酯的共聚物进行反应而成的树脂等树脂[K5];使(甲基)丙烯酸与(甲基)丙烯酸三环癸酯/(甲基)丙烯酸缩水甘油酯的共聚物进行反应而成的树脂进一步与四氢邻苯二甲酸酐反应而成的树脂等树脂[K6]等。
其中,作为树脂(B),优选为树脂[K1]和树脂[K2]。
例如,树脂[K1]可以参考文献“高分子合成的实验法”(大津隆行著、发行所:化学同人株式会社、第1版第1次印刷、1972年3月1日发行)中记载的方法和该文献中记载的引用文献来制造。
应予说明,得到的共聚物可以直接使用反应后的溶液,也可以使用浓缩或稀释的溶液,还可以使用通过再沉淀等方法以固体(粉体)的形式取出的固体(粉体)。特别是通过在该聚合时使用本发明的着色树脂组合物中所含的溶剂作为溶剂,可以将反应后的溶液直接用于本发明的着色树脂组合物的制备,因此,能够简化本发明的着色树脂组合物的制造工序。
树脂(B)的聚苯乙烯换算的重均分子量优选为3000~100000,更优选为5000~50000,进一步优选为5000~30000。如果分子量在上述范围内,则存在滤色器的硬度提高、残膜率高、未曝光部对显影液的溶解性良好且着色图案的分辨率提高的趋势。
树脂(B)的分子量分布[重均分子量(Mw)/数均分子量(Mn)]优选为1.1~6,更优选为1.2~4。
树脂(B)的酸值优选为50~170mg-KOH/g,更优选为60~150mg-KOH/g,进一步优选为70~135mg-KOH/g。在此,酸值是作为中和树脂(B)1g所需的氢氧化钾的量(mg)而测定的值,例如可以通过使用氢氧化钾水溶液进行滴定而求出。
相对于从着色树脂组合物的总量中除去着色剂(A)和溶剂(E)的含量而得的量,树脂(B)的含有率为70质量%以上,优选为90质量%以上,更优选为95质量%以上。通过树脂(B)的含有率为上述范围,着色剂(A)和溶剂(E)以外的其它成分的含有比例受到限定,能够得到耐热性高的滤色器。另外,树脂(B)的含量相对于着色树脂组合物的固体成分的总量优选为50质量%以上,更优选为60质量%以上。
<溶剂(E)>
溶剂(E)没有特别限定,可以使用该领域中通常使用的溶剂。例如可举出酯溶剂(在分子内含有-COO-且不含-O-的溶剂)、醚溶剂(在分子内含有-O-且不含-COO-的溶剂)、醚酯溶剂(在分子内含有-COO-和-O-的溶剂)、酮溶剂(在分子内含有-CO-且不含-COO-的溶剂)、醇溶剂(在分子内含有OH且不含-O-、-CO-和-COO-的溶剂)、芳香族烃溶剂、酰胺溶剂、二甲基亚砜。
作为酯溶剂,可举出乳酸甲酯、乳酸乙酯、乳酸丁酯、2-羟基异丁酸甲酯、乙酸乙酯、乙酸正丁酯、乙酸异丁酯、甲酸戊酯、乙酸异戊酯、丙酸丁酯、丁酸异丙酯、丁酸乙酯、丁酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、乙酰乙酸甲酯、乙酰乙酸乙酯、环己醇乙酸酯和γ-丁内酯等。
作为醚溶剂,可举出乙二醇单甲醚、乙二醇单***、乙二醇单丙醚、乙二醇单丁醚、二乙二醇单甲醚、二乙二醇单***、二乙二醇单丁醚、丙二醇单甲醚、丙二醇单***、丙二醇单丙醚、丙二醇单丁醚、3-甲氧基-1-丁醇、3-甲氧基-3-甲基丁醇、四氢呋喃、四氢吡喃、1,4-二烷、二乙二醇二甲醚、二乙二醇二***、二乙二醇甲***、二乙二醇二丙醚、二乙二醇二丁醚、苯甲醚、苯***和甲基苯甲醚等。
作为醚酯溶剂,可举出甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸丙酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-甲氧基-2-甲基丙酸甲酯、2-乙氧基-2-甲基丙酸乙酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、丙二醇单甲醚乙酸酯、丙二醇单***乙酸酯、丙二醇单丙醚乙酸酯、乙二醇单甲醚乙酸酯、乙二醇单***乙酸酯、二乙二醇单***乙酸酯和二乙二醇单丁醚乙酸酯等。
作为酮溶剂,可举出4-羟基-4-甲基-2-戊酮、丙酮、2-丁酮、2-庚酮、3-庚酮、4-庚酮、4-甲基-2-戊酮、环戊酮、环己酮和异佛尔酮等。
作为醇溶剂,可举出甲醇、乙醇、丙醇、丁醇、己醇、环己醇、乙二醇、丙二醇和甘油等。
作为芳香族烃溶剂,可举出苯、甲苯、二甲苯和均三甲苯等。
作为酰胺溶剂,可举出N,N-二甲基甲酰胺、N,N-二甲基乙酰胺和N-甲基吡咯烷酮等。
上述溶剂中,从涂布性、干燥性的方面考虑,优选1atm下的沸点为120℃~210℃的有机溶剂。作为溶剂,优选为丙二醇单甲醚乙酸酯、乳酸乙酯、丙二醇单甲醚、3-乙氧基丙酸乙酯、乙二醇单甲醚、二乙二醇单甲醚、二乙二醇单***、4-羟基-4-甲基-2-戊酮和N,N-二甲基甲酰胺,更优选为丙二醇单甲醚乙酸酯、丙二醇单甲醚、N,N-二甲基甲酰胺、N-甲基吡咯烷酮和3-乙氧基丙酸乙酯。
溶剂(E)的含量相对于本发明的着色树脂组合物的总量优选为70~95质量%,更优选为75~92质量%。换言之,着色树脂组合物的固体成分的总量优选为5~30质量%,更优选为8~25质量%。如果溶剂(E)的含量在上述范围内,则存在涂布时的平坦性变得良好的趋势。
<流平剂(F)>
作为流平剂(F),可举出有机硅系表面活性剂、氟系表面活性剂和具有氟原子的有机硅系表面活性剂等。它们也可以在侧链具有聚合性基团。
作为有机硅系表面活性剂,可举出在分子内具有硅氧烷键的表面活性剂等。具体而言,可举出Toray Silicone DC3PA、Toray Silicone SH7PA、Toray Silicone DC11PA、Toray Silicone SH21PA、Toray Silicone SH28PA、Toray Silicone SH29PA、ToraySilicone SH30PA、Toray Silicone SH8400(Toray Dow Corning株式会社制造)、KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化学工业株式会社制造)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF-4446、TSF4452和TSF4460(MomentivePerformance Materials Japan合同公司制造)等。
作为上述氟系表面活性剂,可举出在分子内具有氟碳链的表面活性剂等。具体而言,可举出Fluorad(注册商标)FC430、Fluorad FC431(住友3M株式会社制造)、Megafac(注册商标)F142D、Megafac F171、Megafac F172、Megafac F173、Megafac F177、MegafacF183、Megafac F554、Megafac R30、Megafac RS-718-K(DIC株式会社制造)、Eftop(注册商标)EF301、Eftop EF303、Eftop EF351、Eftop EF352(三菱材料电子化成株式会社制造)、Surflon(注册商标)S381、Surflon S382、Surflon SC101、Surflon SC105(旭硝子株式会社制造)和E5844(Daikin Fine Chemical研究所制造)等。
作为上述具有氟原子的有机硅系表面活性剂,可举出在分子内具有硅氧烷键和氟碳链的表面活性剂等。具体而言,可举出Megafac(注册商标)R08、Megafac BL20、MegafacF475、Megafac F477和Megafac F443(DIC株式会社制造)等。
流平剂(F)的含量相对于树脂(B)的含量100质量份优选为0.001质量份~0.2质量份,优选为0.002质量份~0.1质量份,更优选为0.005质量份~0.05质量份。如果流平剂(F)的含量在上述范围内,则能够使滤色器的平坦性良好。
<着色树脂组合物的制造方法>
本发明的着色树脂组合物例如可以通过将着色剂(A)、树脂(B)、溶剂(E)以及根据需要使用的流平剂(F)和其它成分混合而制备。
含有颜料(P)时,颜料(P)优选预先与溶剂(E)的一部分或全部混合,使用珠磨机等使其分散直至颜料的平均粒径成为0.2μm以下左右为止。此时,可以根据需要配合上述颜料分散剂、树脂(B)的一部分或全部。向这样得到的颜料分散液中以成为规定的浓度的方式混合剩余的成分,由此能够制备目标着色树脂组合物。
染料可预先分别溶解于溶剂(E)的一部分或全部中而制备溶液。优选利用孔径0.01~1μm左右的过滤器对该溶液进行过滤。
优选利用孔径0.1~10μm左右的过滤器对混合后的着色树脂组合物进行过滤。
<滤色器的制造方法>
作为由本发明的着色树脂组合物制造滤色器的方法,例如可举出将着色树脂组合物涂布于基板上,通过进行加热干燥(预烘烤)和/或减压干燥而除去溶剂等挥发成分并使其干燥,形成平滑的着色组合物层,接着进行后烘烤的方法等。这样形成的着色固化膜可以为本发明的滤色器。
作为基板,可使用石英玻璃、硼硅酸玻璃、氧化铝硅酸盐玻璃、对表面进行了二氧化硅涂布的钠钙玻璃等玻璃板、聚碳酸酯、聚甲基丙烯酸甲酯、聚对苯二甲酸乙二醇酯等树脂板、硅、在上述基板上形成有铝、银、银/铜/钯合金薄膜等的基板。也可以在这些基板上形成其它滤色器层、树脂层、晶体管、电路等。
作为涂布方法,可举出旋涂法、狭缝涂布法、狭缝和旋涂法等。
进行加热干燥时的温度优选为30~120℃,更优选为50~110℃。另外,作为加热时间,优选为10秒~60分钟,更优选为30秒~30分钟。
进行减压干燥时,优选在50~150Pa的压力下、在20~25℃的温度范围进行。
着色树脂组合物的膜厚没有特别限定,只要根据目标滤色器的膜厚而适当选择即可。
进而,优选对得到的着色树脂组合物的膜进行后烘烤。后烘烤温度优选为150~250℃,更优选为160~235℃。后烘烤时间优选为1~120分钟,更优选为10~60分钟。
得到的滤色器的膜厚没有特别限定,可根据目的、用途等进行适当调整,例如为0.1~30μm,优选为0.1~20μm,进一步优选为0.5~6μm。
这样得到的固化涂膜例如也可以通过蚀刻法等进行图案化。
根据本发明的着色树脂组合物,能够制作耐热性优异的滤色器。该滤色器作为显示装置(例如,液晶显示装置、有机EL装置、电子纸等)和固体摄像元件中使用的滤色器有用。
实施例
以下,通过实施例来更详细地说明本发明,但本发明并不受这些实施例的限定。例中,表示含量和使用量的%和份,只要没有特别说明,就为质量基准。
以下的合成例中,化合物的结构通过NMR(JNM-EX-270;(日本电子株式会社制造))进行鉴定。
将2,4-二甲基苯胺(东京化成工业株式会社制造)10.0份、2-乙基溴代己烷(东京化成工业株式会社制造)17.0份、四丁基溴化铵(和光化学工业株式会社制造)44.0份混合。将得到的混合物在90℃搅拌8小时。反应结束后,加入50份的10%碳酸氢钠水溶液后,加入乙酸乙酯100份并将水层废弃。重复2次利用水、10%盐酸进行清洗的操作后,将溶剂馏去。将得到的油在60℃减压干燥24小时,得到下式(d-1)所示的化合物9.3份。
式(d-1)所示的化合物的1H-NMR(270MHz,δ值(ppm,TMS基准),DMSO-d6)0.85(m,6H),1.23-1.42(br,8H),1.59(br,1H),2.04(s,3H),2.12(s,3H),2.91(d,2H),4.37(br,1H),6.38(d,1H),6.75(s,1H),6.77(d,1H)
将上述得到的式(d-1)所示的化合物3.0份、3-溴代苯酚(东京化成工业株式会社制造)2.2份、乙酸钯0.015份、叔丁氧基钠(东京化成工业株式会社制造)3.2份、三叔丁基膦(东京化成工业株式会社制造)0.055份、甲苯25.6份混合,在100℃搅拌15小时。向得到的混合物中加入乙酸乙酯30份、水100份并将水层废弃。重复2次利用水进行清洗的操作后,将溶剂馏去。利用硅胶色谱(氯仿/己烷=1/1)对残渣进行纯化,将得到的油在60℃减压干燥24小时,得到下式(d-2)所示的化合物所示的化合物1.9份。
式(d-2)所示的化合物的1H-NMR(270MHz,δ值(ppm,TMS基准),DMSO-d6)0.85(m,6H),1.23-1.42(br,8H),1.55(br,1H),1.94(s,3H),2.27(s,3H),2.90(d,2H),6.37(d,1H),6.75(s,1H),6.76(d,1H),6.92-7.14(m,4H),8.93(s,1H)
将上述得到的作为中间体即式(d-2)所示的化合物4.4份、3,4-二羟基-3-环丁烯-1,2-二酮(东京化成工业株式会社制造)0.8份、1-丁醇90.0份和甲苯60.0份混合。将得到的混合物一边使用Dean-Stark管将生成的水除去一边在125℃搅拌3小时。在反应结束后,将溶剂馏去,加入15份的乙酸后,滴加到18%食盐水100份中,滤出析出的固体。将滤出的固体用己烷进行清洗。将得到的固体在60℃减压干燥24小时,得到式(AII-8)所示的化合物(方酸染料a1)4.9份。
式(AII-8)所示的化合物的1H-NMR(270MHz,δ值(ppm,TMS基准),DMSO-d6)0.87(m,12H),1.21-1.57(m,16H),1.72(br,2H),2.05(s,6H),2.36(s,6H),3.37(br,2H),3.78(br,2H),6.00(br,4H),6.97-7.12(m,6H),7.77-7.95(m,2H),11.35(s,1H),12.06(s,1H)
<合成例2:黄色染料a2的合成>
通过日本特开2016-11419号公报中记载的式(Ad2-14)所示的化合物的制造方法来制造下述式所示的化合物(黄色染料b2)。下述式所示的化合物为与日本特开2016-11419号公报的式(Ad2-14)所示的化合物相同的化合物。
<合成例3:树脂b1的合成>
在具备回流冷却器、滴液漏斗和搅拌机的烧瓶内流入适量的氮气而形成氮气气氛,放入丙二醇单甲醚乙酸酯100份,一边搅拌一边加热至85℃。接着,使用滴液泵用约5小时在该烧瓶内滴加将甲基丙烯酸19份、丙烯酸3,4-环氧三环[5.2.1.02,6]癸烷-8-基酯和丙烯酸3,4-环氧三环[5.2.1.02,6]癸烷-9-基酯的混合物(含有比以摩尔比计为50:50)171份溶解于丙二醇单甲醚乙酸酯40份的溶液。另一方面,使用另一滴液泵用约5小时向烧瓶内滴加将聚合引发剂2,2’-偶氮双(2,4-二甲基戊腈)26份溶解于丙二醇单甲醚乙酸酯120份的溶液。在聚合引发剂的滴加结束后,在该温度下保持约3小时,然后冷却至室温,得到固体成分43.5%的树脂b1的溶液。
得到的树脂b1的重均分子量为8000,分子量分布为1.98,固体成分换算的酸值为53mg-KOH/g。树脂b1具有下述所示的结构单元。
树脂b1的聚苯乙烯换算的重均分子量(Mw)和数均分子量(Mn)的测定通过GPC法按以下的条件进行。以下的树脂b2~b3中也同样。
装置:HLC-8120GPC(东曹株式会社制造)
柱:TSK-GELG2000HXL
柱温:40℃
溶剂:THF
流速:1.0mL/min
被检液固体成分浓度:0.001~0.01质量%
注入量:50μL
检测器:RI
校正用标准物质:TSK STANDARD POLYSTYRENE F-40、F-4、F-288、A-2500、A-500(东曹株式会社制造)
将上述得到的聚苯乙烯换算的重均分子量和数均分子量的比(Mw/Mn)设为分子量分布。
<合成例4-1:树脂b2a的合成>
在具备回流冷却器、滴液漏斗和搅拌机的烧瓶内流入适量的氮气而形成氮气气氛,放入丙二醇单甲醚乙酸酯290份,一边搅拌一边加热至85℃。接着,用4小时滴加丙烯酸3,4-环氧三环[5.2.1.02,6]癸烷-8-基酯和丙烯酸3,4-环氧三环[5.2.1.02,6]癸烷-9-基酯(含有比率为1:1)的混合物94份、4-乙烯基苯甲酸61份、甲基丙烯酸苯酯157份和丙二醇单甲醚乙酸酯250份的混合溶液。
另一方面,用5小时滴加将2,2-偶氮双(2,4-二甲基戊腈)9份溶解于丙二醇单甲醚乙酸酯110份的混合溶液。滴加结束后,以85℃将烧瓶内保持3小时后,冷却至室温,得到B型粘度(23℃)70mPas、固体成分28.2%的共聚物(树脂b2a)溶液。生成的共聚物的重均分子量Mw为17000,分散度为2.23。树脂b2a具有下述所示的结构单元。
<合成例4-2:树脂b2b的合成>
在具备回流冷却器、滴液漏斗和搅拌机的烧瓶内流入适量的氮气而形成氮气气氛,放入丙二醇单甲醚乙酸酯306份,一边搅拌一边加热至80℃。接着,用3小时滴加丙烯酸3,4-环氧三环[5.2.1.02,6]癸烷-8-基酯和丙烯酸3,4-环氧三环[5.2.1.02,6]癸烷-9-基酯的混合物(含有比率为1:1)57份、4-乙烯基苯甲酸47份、甲基丙烯酸苯酯155份和丙二醇单甲醚乙酸酯176份的混合溶液。
另一方面,用5小时滴加将2,2-偶氮双(2,4-二甲基戊腈)3份溶解于丙二醇单甲醚乙酸酯87份的混合溶液。滴加结束后,以85℃将烧瓶内保持3小时后,冷却至室温,得到B型粘度(23℃)150mPas、固体成分27.6%的共聚物(树脂b2b)溶液。生成的共聚物的重均分子量Mw为41000,分散度为2.94。树脂b2b具有下述所示的结构单元。
<合成例5:树脂b3的合成>
向具备搅拌机、温度计、回流冷却管、滴液漏斗和气体导入管的烧瓶导入丙二醇单甲醚乙酸酯200份。然后,通过气体导入管将氮气导入烧瓶内,将烧瓶内气氛置换为氮气。将烧瓶内的溶液升温至70℃后,使用滴液漏斗用2小时将由甲基丙烯酸苄酯144份、甲基丙烯酸三环[5.2.1.02.6]癸酯30份、丙烯酸42份、偶氮二异丁腈5.2份和丙二醇单甲醚乙酸酯213份构成的混合物滴加到烧瓶内,滴加完成后,进一步在100℃搅拌5小时。在聚合引发剂的溶液滴加结束后,在70℃保持4小时,然后冷却至室温,得到固体成分34.1%的共聚物(树脂b3)溶液。树脂b3的重均分子量为1.13×104,分子量分布为2.18,固体成分换算的酸值为108.5mg-KOH/g。
树脂b3具有以下的结构单元。
[绿色着色树脂组合物的制备]
以成为下述表2和表3所示的组成的方式将各成分混合而得到绿色着色树脂组合物。表2和表3所示的组成除溶剂(E)以外为固体成分换算量。在表2和表3中,将从绿色着色树脂组合物的总量中除去着色剂(A)和溶剂(E)的含量而得的量设为基准量(S),将树脂(B)相对于基准量(S)的含有率记载为“树脂(B)的含有率”。
将表2和表3中的各成分示于下述。
黄色颜料:C.I.颜料黄150
黄色染料a2:通过合成例2合成的化合物
黄色染料a3:日本特开2012-31218号中记载的下述化合物的混合物
树脂b1:通过合成例3合成的树脂
树脂b2a:通过合成例4-1合成的树脂
树脂b2b:通过合成例4-2合成的树脂
树脂b3:通过合成例5合成的树脂
溶剂e1:丙二醇单甲醚乙酸酯
溶剂e2:N-甲基-2-吡咯烷酮
流平剂f1:Megafac(注册商标)F554(DIC株式会社制造)
[涂膜的形成]
在5cm见方的玻璃基板(eagle XG;Corning公司制造)上,以后烘烤后的膜厚成为0.5μm的方式利用旋涂法涂布实施例1~13和比较例1中制备的绿色着色树脂组合物后,在加热板上以70℃预烘烤1分钟而得到着色涂膜(以下,记载为“后烘烤前的着色涂膜”)。然后,在加热板上以220℃进行10分钟后烘烤,由此得到着色涂膜(以下,记载为“后烘烤后的着色涂膜”)。
<耐热性评价>
测定后烘烤前的着色涂膜与后烘烤后的着色涂膜的xy色度坐标(x,y)和Y,根据该测定值并通过JIS Z 8730:2009(7.色差的计算方法)中记载的方法在后烘烤前后计算色差△E*ab,将结果示于表2和表3。如果色差△E*ab为10以下,则可以说上述着色涂膜作为滤色器在实用上没有问题。
[表2]
[表3]
如表2和表3所示,使用本发明的绿色着色树脂组合物的实施例1~12与比较例1相比,在后烘烤前后色差△E*ab小,耐热性优异。
Claims (4)
式(II)中,R1~R4各自独立地表示氢原子、卤素原子、羟基或碳原子数1~20的1价的饱和烃基,该1价的饱和烃基中所含的氢原子或甲基可以被取代成卤素原子、羟基或碳原子数1~8的烷基氨基,可以在构成该1价的饱和烃基的碳原子间***氧原子或硫原子,
R5~R8相互独立地表示氢原子或羟基,
Ar1和Ar2各自独立地表示下式(i)所示的基团,
式(i)中,R12表示碳原子数1~20的1价的饱和烃基或碳原子数2~20的1价的不饱和烃基,m表示1~5的整数,m为2以上时,多个R12可以分别相同也可以不同,*表示与氮原子的键合位点,
R9和R10各自独立地表示碳原子数1~20的1价的饱和烃基或式(i)所示的基团,该1价的饱和烃基中所含的氢原子或甲基可以被取代成卤素原子、羟基、或者被1个或2个碳原子数1~8的烷基取代的氨基,可以在构成该1价的饱和烃基的碳原子间***氧原子或硫原子。
4.一种滤色器,由权利要求1~3中任一项所述的绿色着色树脂组合物形成。
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