WO2022244586A1 - シリコーン鎖含有重合体、コーティング組成物、レジスト組成物及び物品 - Google Patents
シリコーン鎖含有重合体、コーティング組成物、レジスト組成物及び物品 Download PDFInfo
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- WO2022244586A1 WO2022244586A1 PCT/JP2022/018351 JP2022018351W WO2022244586A1 WO 2022244586 A1 WO2022244586 A1 WO 2022244586A1 JP 2022018351 W JP2022018351 W JP 2022018351W WO 2022244586 A1 WO2022244586 A1 WO 2022244586A1
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- polymerizable monomer
- containing polymer
- meth
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- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004226 phenanthren-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(C([H])=C([H])C3=C(*)C([H])=C([H])C([H])=C23)=C1[H] 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- YFMFSCRSAWIWOP-UHFFFAOYSA-N phenyl(trityl)diazene Chemical compound C1=CC=CC=C1N=NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YFMFSCRSAWIWOP-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 229940099800 pigment red 48 Drugs 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- OJTDGPLHRSZIAV-UHFFFAOYSA-N propane-1,2-diol Chemical class CC(O)CO.CC(O)CO OJTDGPLHRSZIAV-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- FZUOVNMHEAPVBW-UHFFFAOYSA-L quinoline yellow ws Chemical compound [Na+].[Na+].O=C1C2=CC=CC=C2C(=O)C1C1=NC2=C(S([O-])(=O)=O)C=C(S(=O)(=O)[O-])C=C2C=C1 FZUOVNMHEAPVBW-UHFFFAOYSA-L 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- KUIXZSYWBHSYCN-UHFFFAOYSA-L remazol brilliant blue r Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC(S(=O)(=O)CCOS([O-])(=O)=O)=C1 KUIXZSYWBHSYCN-UHFFFAOYSA-L 0.000 description 1
- HFIYIRIMGZMCPC-YOLJWEMLSA-J remazole black-GR Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(\N=N\C=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-YOLJWEMLSA-J 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 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
- 229920002050 silicone resin Polymers 0.000 description 1
- NTOOJLUHUFUGQI-UHFFFAOYSA-M sodium;4-(4-acetamidoanilino)-1-amino-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].C1=CC(NC(=O)C)=CC=C1NC1=CC(S([O-])(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O NTOOJLUHUFUGQI-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 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
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- CYTQZYFSRPGOJK-UHFFFAOYSA-N tris(2,3-dibromo-3-chloropropyl) phosphate Chemical compound ClC(Br)C(Br)COP(=O)(OCC(Br)C(Cl)Br)OCC(Br)C(Cl)Br CYTQZYFSRPGOJK-UHFFFAOYSA-N 0.000 description 1
- ZUCXUTRTSQLRCV-UHFFFAOYSA-K trisodium;1-amino-4-[3-[[4-chloro-6-(3-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2,4,6-trimethyl-5-sulfonatoanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].CC1=C(S([O-])(=O)=O)C(C)=C(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C(N)=C(C=2)S([O-])(=O)=O)C(C)=C1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S([O-])(=O)=O)=C1 ZUCXUTRTSQLRCV-UHFFFAOYSA-K 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- G03F7/004—Photosensitive materials
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/106—Esters of polycondensation macromers
- C08F222/1061—Esters of polycondensation macromers of alcohol terminated polyesters or polycarbonates, e.g. polyester (meth)acrylates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
-
- 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
- C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/47—Levelling agents
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- 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
- G03F7/004—Photosensitive materials
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
Definitions
- the present invention relates to silicone chain-containing polymers, coating compositions, resist compositions and articles.
- a leveling agent is added to smooth the coating film obtained by applying a coating composition such as a coating composition or a resist composition. Specifically, by adding a leveling agent to the coating composition, the leveling agent is oriented on the surface of the coating film to lower the surface tension of the coating film, thereby smoothing the resulting coating film.
- a coating film having a smooth surface can improve repellency and unevenness.
- Leveling agents are used, for example, in automotive paints, and a coating composition containing a leveling agent can impart high smoothness to the resulting coating film surface and can impart gloss to the appearance of automobiles. Silicone-based leveling agents have been proposed as leveling agents for automotive coatings (Patent Documents 1 and 2).
- leveling agents are diverse, and they are also used, for example, in color resist compositions used in the production of color filters for liquid crystal displays.
- a color resist composition is generally applied onto a glass substrate by a coating method such as spin coating or slit coating, and after drying, the coating film is exposed using a mask and then developed to form a colored pattern.
- the step of forming is included. At this time, when the smoothness of the coating film is not good and the film thickness is uneven, or when there is coating unevenness, cissing, etc., color unevenness may occur in the pixels.
- the smoothness of the resulting coating film is improved, and the red (R), green (G), and blue (B) pixels and the areas between these pixels are formed.
- the surface of the black matrix (BM) can exhibit high smoothness, and a color filter with little color unevenness can be obtained.
- a silicone-based leveling agent exerts a leveling effect by segregation of the silicone-based leveling agent on the surface (interface with air) due to the low surface tension of the silicone chain.
- the segregation performance was not sufficient, and the obtained leveling effect was also not sufficient.
- the problem to be solved by the present invention is to provide a silicone chain-containing polymer that functions as a leveling agent that imparts high smoothness to the coating film.
- the present inventors have conducted intensive studies to solve the above problems, and as a result, a polymer having a polymerizable monomer having a specific silicone chain and a polymerizable monomer having a specific ester chain as a polymerization component is produced.
- the present inventors have completed the present invention on the basis of the finding that the composition exhibits high leveling properties that can withstand use in resist applications.
- the present invention provides a silicone having at least a polymerizable monomer (1) having a silicone chain represented by the following general formula (A) and a polymerizable monomer (2) having a polyester chain as polymerization components. It relates to chain-containing polymers. .
- each R 11 is independently an alkyl group having 1 to 6 carbon atoms or a group represented by —OSi(R 14 ) 3 (each R 14 is independently an alkyl group having 1 to 3 carbon atoms); each R 12 is independently an alkyl group having 1 to 6 carbon atoms; R 13 is an alkyl group having 1 to 6 carbon atoms, x is an integer of 0 or more. )
- silicone chain-containing polymer that functions as a leveling agent that imparts high smoothness to the coating film.
- (meth)acrylate means one or both of acrylate and methacrylate.
- the silicone chain-containing polymer of the present invention (hereinafter sometimes simply referred to as "the polymer of the present invention") comprises a polymerizable monomer (1) having a group represented by the following general formula (A) and a polyester It is a polymer containing at least a polymerizable monomer (2) having a chain-containing group as a polymer component.
- each R 11 is independently an alkyl group having 1 to 6 carbon atoms or a group represented by —OSi(R 14 ) 3 (each R 14 is independently an alkyl group having 1 to 3 carbon atoms); each R 12 is independently an alkyl group having 1 to 6 carbon atoms; R 13 is an alkyl group having 1 to 6 carbon atoms, x is an integer of 0 or more. )
- the polyester chain-containing group has slightly lower compatibility with, for example, the binder resin and solvent contained in the coating composition, compared to the alkylene chain-containing group and the alkyleneoxy chain-containing group. Therefore, when the coating composition contains the polymer of the present invention, it is considered that the polymer of the present invention tends to segregate on the coating film surface of the coating composition.
- C C-containing groups
- a (meth)acryloyl group and a (meth)acryloyloxy group are preferable because of the availability of raw materials and favorable polymerization reactivity.
- the number of polymerizable unsaturated groups possessed by the polymerizable monomer may be one, or two or more.
- polymerization component means a component that constitutes a polymer, and does not include solvents, polymerization initiators, etc. that do not constitute a polymer.
- R 11 is preferably a methyl group or a trimethylsiloxy group
- R 12 and R 13 are preferably methyl groups.
- the number average of x is preferably an integer in the range of 1 to 200, more preferably an integer in the range of 1 to 150, still more preferably an integer in the range of 1 to 75 and particularly preferably an integer in the range of 1-20.
- the polymerizable monomer (1) should have at least the group represented by the general formula (A), and is preferably a compound represented by the following general formula (1-1).
- R 11 , R 12 , R 13 and x are respectively the same as R 11 , R 12 , R 13 and x in the general formula (A);
- R 15 is a hydrogen atom or a methyl group,
- L 1 is a divalent organic group or a single bond.
- the divalent organic group of L 1 is preferably a single bond, an alkylene group having 1 to 50 carbon atoms or an alkyleneoxy group having 1 to 50 carbon atoms.
- the alkylene group having 1 to 50 carbon atoms for L 1 includes methylene group, ethylene group, n-propylene group, n-butylene group, n-pentylene group, n-hexylene group, n-heptylene group and n-octylene. group, n-nonylene group, n-decylene group, n-dodecylene group, isopropylene group, 2-methylpropylene group, 2-methylhexylene group, tetramethylethylene group and the like.
- the alkylene group having 1 to 50 carbon atoms of L 1 is preferably an alkylene group having 1 to 15 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, still more preferably a methylene group, ethylene group, n-propylene group or isopropylene group.
- the alkyleneoxy group having 1 to 50 carbon atoms in L 1 is, for example, a group in which one —CH 2 — in the alkylene group is substituted with —O—.
- the alkyleneoxy group having 1 to 50 carbon atoms of L 1 is preferably an alkyleneoxy group having 1 to 15 carbon atoms, more preferably an alkyleneoxy group having 1 to 8 carbon atoms, and still more preferably methylene. oxy group, ethyleneoxy group, propyleneoxy group, oxytrimethylene group, butyleneoxy group, oxytetramethylene group, pentyleneoxy group, heptyleneoxy group or octyleneoxy group.
- divalent organic group for L 1 is an alkylene group having 1 to 50 carbon atoms or an alkyleneoxy group having 1 to 50 carbon atoms
- the polymerizable monomer (1) can be produced by a known method, and commercially available products may be used. Specific examples of the polymerizable monomer (1) include ⁇ -(3-methacryloyloxy)propylpolydimethylsiloxane and 3-(methacryloyloxy)propyltris(trimethylsiloxy)silane.
- the group containing the polyester chain of the polymerizable monomer (2) is preferably a group represented by the following general formula (B-1) or a group represented by the following general formula (B-2).
- R 21 is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkyl group having an ether bond having 1 to 18 carbon atoms, p is an integer ranging from 1 to 30, and q is an integer of 2 or more.
- the alkyl group having 1 to 18 carbon atoms in R 21 may be any of a linear alkyl group, a branched alkyl group and a cyclic alkyl group, and Examples include methyl group, ethyl group, normal propyl group, isopropyl group, n-butyl group, t-butyl group, n-hexyl group, cyclohexyl group, n-octyl group and hexadecyl group.
- the alkyl group having 1 to 18 carbon atoms for R 21 is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms.
- the alkyl group having 1 to 18 carbon atoms and having an ether bond for R 21 is such that —CH 2 — in the alkyl group is an ether bond (—O—) is a group substituted with That is, R 21 includes an alkyleneoxyalkyl group having 2 to 18 carbon atoms, a polyoxyalkylenealkyl group having 3 to 18 carbon atoms, and an oxacycloalkyl group having 2 to 18 carbon atoms.
- p is an integer in the range of 1 to 30, preferably an integer in the range of 1 to 10, more preferably p is in the range of 1 to 6. and more preferably p is an integer in the range of 2-6.
- q is an integer of 2 or more, for example, the number average of q is in the range of 2 to 100, preferably in the range of 2 to 50, and more It is preferably in the range of 3-30, more preferably in the range of 4-15.
- the number average value of q can be read from the GPC chart.
- the polymerizable monomer (2) may have at least a group containing a polyester chain, preferably a compound represented by the following general formula (2-1) or represented by the following general formula (2-2) It is a compound that
- R 21 , p and q are the same as R 21 , p and q of the general formulas (B-1) and (B-2);
- L2 is a divalent organic group or a single bond, R22 is a hydrogen atom or a methyl group.
- the divalent organic group for L 2 is preferably a single bond, an alkylene group having 1 to 50 carbon atoms, or an alkylene group having 1 to 50 carbon atoms. It is an oxy group or a group containing a polyoxyalkylene chain.
- the group containing a polyoxyalkylene chain is a divalent linking group containing repeating oxyalkylene moieties.
- Examples of the alkylene group having 1 to 50 carbon atoms and the alkyleneoxy group having 1 to 50 carbon atoms for L 2 are the same as those for L 1 .
- Polymerizable monomer (2) can be produced by a known method, and can be obtained, for example, by modifying a polymerizable monomer having a group containing a polyoxyalkylene chain with lactone.
- the value of q in the formulas (B-1) and (B-2) can be adjusted depending on the amount of lactone modification.
- the compound represented by the general formula (2-1) can be obtained by modifying the compound represented by the general formula (3-2) described later with a lactone.
- the polymer of the present invention may be any polymer containing the polymerizable monomer (1) and the polymerizable monomer (2) as polymerization components, and the polymerization method is not particularly limited.
- the polymer of the present invention may be a random copolymer of the polymerizable monomer (1) and the polymerizable monomer (2). It may be a block copolymer, preferably a block copolymer of polymerizable monomer (1) and polymerizable monomer (2).
- the polymer of the present invention is a block copolymer of the polymerizable monomer (1) and the polymerizable monomer (2)
- the polymer block of the polymerizable monomer (1) and the polymerizable monomer The number and bonding order of the polymer blocks of (2) are not particularly limited. It may be a polymer.
- the polymerizable monomer (1) may be a single polymerizable monomer (1) or two or more polymerizable monomers (1) having different structures.
- the polymerizable monomer (2) in the polymerization component may be a single polymerizable monomer (2) or two or more polymerizable monomers (2) having different structures.
- the content ratio of the polymerizable monomer (1) in the polymerizable component is preferably in the range of 5 to 95% by mass, more preferably 5 to 75% by mass. %, more preferably 10 to 70% by mass.
- the content of the polymerizable monomer (1) can be adjusted by adjusting the raw material charging ratio of the polymerizable monomer (1) when producing the polymer of the present invention.
- the content ratio of the polymerizable monomer (2) in the polymerizable component is preferably in the range of 5 to 95% by mass, more preferably 25 to 95% by mass. %, more preferably 30 to 90 mass %.
- the content of the polymerizable monomer (2) can be adjusted by adjusting the raw material charging ratio of the polymerizable monomer (2) when producing the polymer of the present invention.
- the content ratio of the groups represented by the general formula (A) in the polymer of the present invention (sum of the masses of the groups represented by the formula (A)/mass of the silicone chain-containing polymer) is preferably 5 to 70. % by mass, more preferably 10 to 60% by mass.
- the content ratio of the group represented by the general formula (A) can be adjusted by adjusting the raw material charging ratio of the polymerizable monomer (1) used when producing the polymer of the present invention.
- the polymerizable component may contain the polymerizable monomer (1) and the polymerizable monomer (2), and substantially consists of the polymerizable monomer (1) and the polymerizable monomer (2). Alternatively, it may consist of only the polymerizable monomer (1) and the polymerizable monomer (2).
- “substantially” means that the total content of the polymerizable monomer (1) and the polymerizable monomer (2) in the polymerization component is, for example, 80% by mass or more, 90% by mass or more, 95% by mass or more. It means that it is 98% by mass or more or 98% by mass or more.
- the polymerizable component of the polymer of the present invention may contain other polymerizable monomers other than the polymerizable monomer (1) and the polymerizable monomer (2), and the other polymerizable monomer
- the body includes a polymerizable monomer (3) having one or more selected from an alkyl group having 1 to 18 carbon atoms, an aromatic group having 6 to 18 carbon atoms and a group containing a polyoxyalkylene chain. be done.
- the alkyl group having 1 to 18 carbon atoms of the polymerizable monomer (3) may be any of a linear alkyl group, a branched alkyl group and a cyclic alkyl group. Examples include propyl, isopropyl, n-butyl, t-butyl, n-hexyl, cyclohexyl, n-octyl and hexadecyl groups.
- the alkyl group having 1 to 18 carbon atoms of the polymerizable monomer (3) may be substituted with one or more substituents such as hydroxyl group, phenyl group and phenoxy group.
- the alkyl group having 1 to 18 carbon atoms possessed by the polymerizable monomer (3) is, for example, a hydroxyalkyl group having 1 to 18 carbon atoms, a phenylalkyl group having 7 to 18 carbon atoms, a phenylalkyl group having 7 to 18 carbon atoms, contains a phenoxyalkyl group of
- the alkyl group having 1 to 18 carbon atoms possessed by the polymerizable monomer (3) is preferably an alkyl group having 1 to 8 carbon atoms.
- Examples of the aromatic group having 6 to 18 carbon atoms possessed by the polymerizable monomer (3) include phenyl group, naphthyl group, anthracen-1-yl group, phenanthren-1-yl group and the like.
- the aromatic group having 6 to 18 carbon atoms of the polymerizable monomer (3) may be further substituted with a substituent such as a hydroxyl group, an alkyl group, or an alkoxy group, for example an alkyl group having 1 to 6 carbon atoms. Includes substituted phenyl groups.
- the group containing a polyoxyalkylene chain possessed by the polymerizable monomer (3) is a monovalent group containing a repeating oxyalkylene moiety or a divalent linking group containing a repeating oxyalkylene moiety.
- Examples of the polymerizable monomer (3) having an alkyl group having 1 to 18 carbon atoms and having a (meth)acryloyl group as the polymerizable unsaturated group include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, s-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) Acrylate, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, stearyl (me
- Examples of the polymerizable monomer (3) having a hydroxyalkyl group having 1 to 18 carbon atoms and having a (meth)acryloyl group as the polymerizable unsaturated group include 2-hydroxyethyl (meth)acrylate, 2- Hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxy(meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate, 2,3-dihydroxypropyl(meth)acrylate and the like. be done.
- Examples of the polymerizable monomer (3) having a phenylalkyl group having 7 to 18 carbon atoms or a phenoxyalkyl group having 7 to 18 carbon atoms and having a (meth)acryloyl group as the polymerizable unsaturated group include benzyl (meth)acrylate, 2-phenoxymethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate and the like.
- Examples of the polymerizable monomer (3) having a group containing a polyoxyalkylene chain and having a (meth)acryloyl group as the polymerizable unsaturated group include polypropylene glycol mono(meth)acrylate, polyethylene glycol mono(meth) Acrylate, polytrimethylene glycol mono(meth)acrylate, polytetramethylene glycol mono(meth)acrylate, poly(ethylene glycol/propylene glycol) mono(meth)acrylate, polyethylene glycol/polypropylene glycol mono(meth)acrylate, poly(ethylene) glycol/tetramethylene glycol) mono(meth)acrylate, polyethylene glycol/polytetramethylene glycol mono(meth)acrylate, poly(propylene glycol/tetramethylene glycol) mono(meth)acrylate, polypropylene glycol/polytetramethylene glycol mono(meth)acrylate ) acrylate, poly(propylene glycol/tet
- poly(ethylene glycol/propylene glycol) means a random copolymer of ethylene glycol and propylene glycol
- polyethylene glycol/polypropylene glycol means a block copolymer of ethylene glycol and propylene glycol.
- Examples of the polymerizable monomer (3) having an alkyl group having 1 to 18 carbon atoms and having a vinyl ether group as the polymerizable unsaturated group include methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n -butyl vinyl ether, isobutyl vinyl ether, tert-butyl vinyl ether, n-pentyl vinyl ether, n-hexyl vinyl ether, n-octyl vinyl ether, n-dodecyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexyl vinyl ether and other alkyl vinyl ethers, cycloalkyl vinyl ethers, 2- Hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether, 4-hydroxybutyl vinyl ether, 5-hydroxypentyl vinyl ether, 6-hydroxyhexyl vinyl ether, 1-hydroxypropyl vinyl
- Examples of the polymerizable monomer (3) having an alkyl group having 1 to 18 carbon atoms and having an allyl group as the polymerizable unsaturated group include 2-hydroxyethyl allyl ether, 4-hydroxybutyl allyl ether and glycerol. monoallyl ether and the like.
- Examples of the polymerizable monomer (3) having an aromatic group with 6 to 18 carbon atoms include styrene, ⁇ -methylstyrene, p-methylstyrene, p-methoxystyrene and the like.
- Examples of the polymerizable monomer (3) having an alkyl group having 1 to 18 carbon atoms and having a (meth)acryloylamino group as the polymerizable unsaturated group include N,N-dimethylacrylamide, N,N- diethylacrylamide, N-isopropylacrylamide, diacetoneacrylamide, acryloylmorpholine and the like.
- Examples of the polymerizable monomer (3) having an alkyl group having 1 to 18 carbon atoms and having a maleimide group as the polymerizable unsaturated group include methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, hexylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, cyclohexylmaleimide and the like.
- the polymerizable monomer (3) is preferably a compound represented by the following general formula (3-1) or a compound represented by (3-2). These compounds can impart compatibility when the polymer of the present invention is used as a leveling agent.
- R 31 is an alkyl group having 1 to 18 carbon atoms
- R 32 is a hydrogen atom or a methyl group
- R 33 is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms
- R 34 is a hydrogen atom or a methyl group
- n is an integer ranging from 1-4 and m is an integer ranging from 1-200.
- the alkyl group having 1 to 18 carbon atoms for R 31 and R 33 is preferably an alkyl group having 1 to 8 carbon atoms.
- m is preferably an integer in the range of 2-50, more preferably an integer in the range of 3-20.
- the polymerizable monomer (3) is preferably a compound represented by the following general formula (3-3).
- each R 35 is independently an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms;
- R 36 is a hydrogen atom or a methyl group, l is an integer from 0 to 5;
- the content ratio of the polymerizable monomer (3) in the polymerizable component is preferably 1. It is in the range of to 20% by mass, more preferably in the range of 1 to 10% by mass.
- Polymerizable monomer (3) can be produced by a known method. Moreover, a commercial item may be used for the polymerizable monomer (3).
- a commercial product of a polymerizable monomer (3-2) having a group containing a polyoxyalkylene chain and a polymerizable unsaturated group being a (meth) acryloyl group Shin-Nakamura Chemical Co., Ltd., "NK Ester M-20G”, “NK Ester M-40G”, “NK Ester M-90G”, “NK Ester M-230G”, “NK Ester AM-90G”, “NK Ester AMP-10G", “NK Ester AMP -20G”, “NK Ester AMP-60G", NOF Corporation "Blenmer PE-90", “Blenmer PE-200", “Blenmer PE-350”, “Blenmer PME-100", “Blenmer PME- 200”, “Blenmer PME-400”, “Blenmer PME-4000”, “Blenmer PE-90
- the polymer of the present invention preferably does not contain fluorine atoms. By being a fluorine atom-free polymer, the accumulation in the environment becomes low, and the environmental load can be reduced.
- the polymers of the invention preferably do not contain reactive functional groups.
- the "reactive functional group” is a functional group capable of forming a crosslinked structure or the like by reacting with another functional group. and the like.
- the number average molecular weight (Mn) of the polymer of the present invention is preferably in the range of 1,000 to 500,000, more preferably in the range of 2,000 to 100,000, even more preferably in the range of 2,000 to 20,000 range.
- the weight average molecular weight (Mw) of the polymer of the present invention is preferably in the range of 1,000 to 500,000, more preferably in the range of 2,000 to 100,000, still more preferably in the range of 5,000 to 40,000 range.
- the dispersity (Mw/Mn) of the polymer of the present invention is, for example, 5.0 or less, preferably 3.0 or less, more preferably 2.0 or less, and still more preferably 1.5 or less. be.
- the lower limit of the degree of dispersion is not particularly limited, it is, for example, 1.0.
- the number average molecular weight (Mn) and weight average molecular weight (Mw) of the polymer of the present invention are measured by the methods described in Examples.
- the method for producing the polymer of the present invention is not particularly limited, and the polymer can be produced by a known method.
- the polymer of the present invention can be produced by a solution polymerization method, a bulk polymerization method, an emulsion polymerization method, or the like based on a polymerization mechanism such as a radical polymerization method, a cationic polymerization method, an anionic polymerization method, or the like.
- a radical polymerization method the polymer of the present invention can be produced by charging polymerization components into an organic solvent and adding a general-purpose radical polymerization initiator.
- the polymer obtained above is a random copolymer.
- Various polymerization initiators can be used, for example, peroxides such as t-butylperoxy-2-ethylhexanoate, benzoyl peroxide, diacyl peroxide, azobisisobutyronitrile , azo compounds such as dimethyl azobisisobutyrate and phenylazotriphenylmethane, and metal chelate compounds such as Mn(acac) 3 .
- peroxides such as t-butylperoxy-2-ethylhexanoate
- benzoyl peroxide diacyl peroxide
- azobisisobutyronitrile azo compounds
- azo compounds such as dimethyl azobisisobutyrate and phenylazotriphenylmethane
- metal chelate compounds such as Mn(acac) 3 .
- a chain transfer agent such as lauryl mercaptan, 2-mercaptoethanol, ethylthioglycolic acid, octylthioglycolic acid, or a thiol compound having a coupling group such as ⁇ -mercaptopropyltrimethoxysilane may be used as a chain transfer agent. may be used as an additive for
- organic solvent examples include alcohols such as ethanol, isopropyl alcohol, n-butanol, iso-butanol and tert-butanol, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and methyl amyl ketone, methyl acetate and ethyl acetate.
- alcohols such as ethanol, isopropyl alcohol, n-butanol, iso-butanol and tert-butanol
- ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and methyl amyl ketone, methyl acetate and ethyl acetate.
- the polymer of the present invention can also be produced by subjecting polymerization components to living polymerization such as living radical polymerization and living anion polymerization.
- living polymerization such as living radical polymerization and living anion polymerization.
- the polymer obtained above is a block copolymer.
- a dormant species whose active polymerization terminal is protected by an atom or an atomic group reversibly generates a radical and reacts with the monomer to proceed with the propagating reaction, even if the first monomer is consumed. Propagating ends can be reacted with sequentially added second monomers to give block polymers without loss of activity.
- Examples of such living radical polymerization include atom transfer radical polymerization (ATRP), reversible addition-fragmentation radical polymerization (RAFT), nitroxide-mediated radical polymerization (NMP), radical polymerization using organotellurium (TERP), and the like. is mentioned.
- ATRP is polymerized using an organic halide, a sulfonyl halide compound, or the like as a polymerization initiator and a metal complex composed of a transition metal compound and a ligand as a catalyst.
- polymerization initiators that can be used in ATRP include 1-phenylethyl chloride, 1-phenylethyl bromide, chloroform, carbon tetrachloride, 2-chloropropionitrile, ⁇ , ⁇ '-dichloroxylene, ⁇ , ⁇ ' -dibromoxylene, hexakis( ⁇ -bromomethyl)benzene, 2-halogenated carboxylic acids having 1 to 6 carbon atoms (e.g. 2-chloropropionic acid, 2-bromopropionic acid, 2-chloroisobutyric acid, 2-bromoisobutyric acid, etc.) and alkyl esters having 1 to 6 carbon atoms.
- alkyl esters having 1 to 6 carbon atoms of 2-halogenated carboxylic acids having 1 to 6 carbon atoms include, for example, methyl 2-chloropropionate, ethyl 2-chloropropionate, 2- Examples include methyl bromopropionate and ethyl 2-bromoisobutyrate.
- Transition metal compounds that can be used in ATRP are those represented by Mn+ Xn .
- the transition metal M n+ of the transition metal compound represented by M n+ X n includes Cu + , Cu 2+ , Fe 2+ , Fe 3+ , Ru 2+ , Ru 3+ , Cr 2+ , Cr 3+ , Mo 0 , Mo + , Mo 2+ , Mo 3+ , W 2+ , W 3+ , Rh 3+ , Rh 4+ , Co + , Co 2+ , Re 2+ , Re 3+ , Ni 0 , Ni + , Mn 3+ , Mn 4+ , V 2+ , V 3+ , Zn + , It can be selected from the group consisting of Zn2 + , Au + , Au2 + , Ag + and Ag2 + .
- X in the transition metal compound represented by M n+ X n is a halogen atom, an alkoxyl group having 1 to 6 carbon atoms, (SO 4 ) 1/2 , (PO 4 ) 1/3 , (HPO 4 ) 1/ 2 , ( H2PO4 ), triflate, hexafluorophosphate, methanesulfonate, arylsulfonate (preferably benzenesulfonate or toluenesulfonate), SeR11 , CN and R12COO .
- R 11 represents an aryl group or a linear or branched alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms); It represents a linear or branched alkyl group (preferably methyl group) having 1 to 6 carbon atoms which may be substituted 5 times (preferably 1 to 3 times with fluorine or chlorine).
- n represents the formal charge on the metal and is an integer of 0-7.
- the ligand compound capable of coordinating to the transition metal of the above transition metal compound includes one or more nitrogen atoms, oxygen atoms, phosphorus atoms or sulfur atoms capable of coordinating with the transition metal via a ⁇ bond.
- the transition metal complex is not particularly limited, but is preferably a group 7, 8, 9, 10, or 11 transition metal complex, and more preferably zerovalent copper, monovalent copper, or divalent ruthenium. , divalent iron or divalent nickel complexes.
- Divalent ruthenium complexes include dichlorotris(triphenylphosphine)ruthenium, dichlorotris(tributylphosphine)ruthenium, dichloro(cyclooctadiene)ruthenium, dichlorobenzeneruthenium, dichloro p-cymeneruthenium, dichloro(norbornadiene)ruthenium, cis-dichlorobis(2,2'-bipyridine)ruthenium, dichlorotris(1,10-phenanthroline)ruthenium, carbonylchlorohydridotris(triphenylphosphine)ruthenium and the like.
- bivalent iron complexes include bistriphenylphosphine complexes and triazacyclononane complexes.
- Atom transfer radical polymerization is not limited to the above, and ATRP other than the above can also be carried out.
- AGET ATRP, ARGET ATRP, ICAR ATRP, etc. described in "Macromol. Rapid. Commun. 2018, 1800616" can also be adopted.
- a solvent is preferably used in the living radical polymerization.
- solvents used in living radical polymerization include ester solvents such as ethyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate; ether solvents such as diisopropyl ether, dimethoxyethane, and diethylene glycol dimethyl ether; and halogen solvents such as dichloromethane and dichloroethane.
- Solvents Aromatic solvents such as toluene, xylene and anisole; Ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; Alcohol solvents such as methanol, ethanol and isopropanol; Aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide etc.
- Aromatic solvents such as toluene, xylene and anisole
- Ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone
- Alcohol solvents such as methanol, ethanol and isopropanol
- Aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide etc.
- the above solvents may be used singly or in combination of two or more.
- Method 1 Polymerizable monomer (1) and polymerizable monomer (2) are reacted in the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of coordinating with the transition metal, and a solvent.
- a method of living radical polymerization preferably atom transfer radical polymerization.
- Method 2 Polymerizable monomer (1) is subjected to living radical polymerization (preferably atom transfer radical polymerization) in the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of coordinating with the transition metal, and a solvent.
- the polymerizable monomer (2) is added to the reaction system to further polymerize the polymer block of the polymerizable monomer (1).
- a method of subjecting the monomer (2) to living radical polymerization preferably atom transfer radical polymerization.
- Method 3 Polymerizable monomer (2) is subjected to living radical polymerization (preferably atom transfer radical polymerization) in the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of coordinating with the transition metal, and a solvent.
- the polymerizable monomer (1) is added to the reaction system to further polymerize the polymer block of the polymerizable monomer (2).
- a method of subjecting the monomer (1) to living radical polymerization preferably atom transfer radical polymerization).
- the polymerization temperature during the living radical polymerization is preferably in the range of room temperature to 120°C.
- metals derived from the transition metal compound used in the polymerization may remain in the resulting polymer. Metals remaining in the resulting polymer may be removed using activated alumina or the like after the completion of the polymerization.
- the polymer of the present invention can be suitably used as a leveling agent for coating compositions, and the coating composition of the present invention contains the polymer of the present invention. Since the polymer of the present invention can be used as a fluorine atom-free leveling agent that does not contain fluorine atoms, it is a leveling agent with low environmental load and low accumulation in the environment.
- the content of the polymer of the present invention contained in the coating composition of the present invention varies depending on the type of base resin, coating method, desired film thickness, etc., but is 0 per 100 parts by mass of the solid content of the coating composition. 0.001 to 10 parts by weight is preferred, 0.01 to 5 parts by weight is more preferred, and 0.05 to 1 part by weight is even more preferred. If the content of the polymer of the present invention is within this range, the surface tension can be sufficiently lowered, the desired leveling property can be obtained, and the occurrence of defects such as foaming during coating can be suppressed. .
- the application of the coating composition of the present invention is not particularly limited, and it can be used for any application that requires leveling properties.
- the coating composition of the present invention can be used, for example, as various coating compositions and photosensitive resin compositions.
- examples of the coating composition include petroleum resin coating, shellac coating, rosin-based coating, cellulose-based coating, rubber-based coating, lacquer coating, and cashew resin coating. , paints using natural resins such as oil-based vehicle paints; phenol resin paints, alkyd resin paints, unsaturated polyester resin paints, amino resin paints, epoxy resin paints, vinyl resin paints, acrylic resin paints, polyurethane resin paints, silicone resin paints and paints using synthetic resins such as fluorine resin paints.
- By adding the polymer of the present invention to the coating composition smoothness can be imparted to the resulting coating film.
- Coloring agents such as pigments, dyes and carbon
- inorganic powders such as silica, titanium oxide, zinc oxide, aluminum oxide, zirconium oxide, calcium oxide and calcium carbonate
- Organic fine powders such as acrylic resins and polyethylene
- various additives such as light resistance improvers, weather resistance improvers, heat resistance improvers, antioxidants, thickeners and anti-settling agents can be added as appropriate.
- any method can be used as long as it is a known and public coating method.
- Methods such as gravure coater, die coater, knife coater, inkjet, dipping coating, spray coating, shower coating, screen printing, gravure printing, offset printing and reverse coating can be used.
- the photosensitive resin composition changes its physical properties such as solubility, viscosity, transparency, refractive index, conductivity and ion permeability when irradiated with light such as visible light or ultraviolet light.
- photosensitive resin compositions resist compositions (photoresist compositions, color resist compositions for color filters, etc.) are required to have high leveling properties.
- the resist composition is usually applied by spin coating to a thickness of about 1 to 2 ⁇ m on a silicon wafer or a glass substrate deposited with various metals. At this time, if the coating film thickness fluctuates or coating unevenness occurs, the linearity and reproducibility of the pattern are degraded, resulting in a problem that a resist pattern having the desired accuracy cannot be obtained.
- the polymer of the present invention exhibits a high leveling property and can form a uniform coating film (cured product), so when used as a resist composition, the above can solve the problem.
- the photoresist composition contains an alkali-soluble resin, a radiation-sensitive substance (photosensitive substance), a solvent, etc. in addition to the polymer of the present invention.
- the alkali-soluble resin contained in the photoresist composition is a resin that is soluble in an alkaline solution, which is a developer used when patterning the resist.
- Alkali-soluble resins include, for example, novolac resins obtained by condensing aromatic hydroxy compound derivatives such as phenol, cresol, xylenol, resorcinol, phlorogricinol, and hydroquinone with aldehyde compounds such as formaldehyde, acetaldehyde, and benzaldehyde; o- Polymers or copolymers of vinylphenol compound derivatives such as vinylphenol, m-vinylphenol, p-vinylphenol, and ⁇ -methylvinylphenol; (meth)acryls such as acrylic acid, methacrylic acid, and hydroxyethyl (meth)acrylate Acid-based polymer or copolymer; Polyvinyl alcohol; Modification by introducing radiation-sensitive groups such as quinonediazide groups
- the radiation-sensitive substance contained in the photoresist composition is an alkali-soluble resin that is irradiated with energy rays such as ultraviolet rays, deep ultraviolet rays, excimer laser light, X-rays, electron beams, ion beams, molecular beams, and ⁇ -rays.
- energy rays such as ultraviolet rays, deep ultraviolet rays, excimer laser light, X-rays, electron beams, ion beams, molecular beams, and ⁇ -rays.
- energy rays such as ultraviolet rays, deep ultraviolet rays, excimer laser light, X-rays, electron beams, ion beams, molecular beams, and ⁇ -rays.
- energy rays such as ultraviolet rays, deep ultraviolet rays, excimer laser light, X-rays, electron beams, ion beams, molecular beams, and ⁇ -rays.
- quinonediazide compounds examples include 1,2-benzoquinoneazide-4-sulfonic acid ester, 1,2-naphthoquinonediazide-4-sulfonic acid ester, 1,2-naphthoquinonediazide-5-sulfonic acid ester, 2, 1-naphthoquinonediazide-4-sulfonic acid ester, 2,1-naphthoquinonediazide-5-sulfonic acid ester, other 1,2-benzoquinoneazide-4-sulfonic acid chloride, 1,2-naphthoquinonediazide-4-sulfonic acid chloride , 1,2-naphthoquinonediazide-5-sulfonic acid chloride, 2,1-naphthoquinonediazide-4-sulfonic acid chloride, 2,1-naphthoquinonediazide-5-sulfonic acid chloride, and sulfonic acid chlorides of quinonediazide
- diazo compound examples include salts of condensates of p-diazodiphenylamine and formaldehyde or acetaldehyde; Examples include diazo resin inorganic salts which are reactive products, and diazo resin organic salts which are reaction products of the above condensates and sulfonic acids as described in US Pat. No. 3,300,309.
- azide compounds examples include azido chalconic acid, diazidobenzalmethylcyclohexanones, azidocinnamylideneacetophenones, aromatic azide compounds, and aromatic diazide compounds.
- halogenated organic compound examples include halogen-containing oxadiazole-based compounds, halogen-containing triazine-based compounds, halogen-containing acetophenone-based compounds, halogen-containing benzophenone-based compounds, halogen-containing sulfoxide-based compounds, halogen-containing sulfone-based compounds, and halogen-containing compounds.
- tris(2,3-dibromopropyl) phosphate tris(2,3-dibromo-3-chloropropyl) phosphate, chlorotetrabromomethane, hexachlorobenzene, hexabromobenzene, hexabromocyclododecane, hexabromobiphenyl , tribromophenyl allyl ether, tetrachlorobisphenol A, tetrabromobisphenol A, bis(bromoethyl ether) tetrabromobisphenol A, bis(chloroethyl ether) tetrachlorobisphenol A, tris(2,3-dibromopropyl) isocyanurate , 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, 2,2-bis(4-hydroxyethoxy-3,5-dibromophen
- organic acid esters include carboxylic acid esters and sulfonic acid esters.
- organic acid amides include carboxylic acid amides and sulfonic acid amides.
- organic acid imides include carboxylic acid imides, sulfonic acid imides, and the like.
- the radiation-sensitive substances may be used singly or in combination of two or more.
- the content of the radiation-sensitive substance is preferably in the range of 10 to 200 parts by mass, more preferably in the range of 50 to 150 parts by mass, with respect to 100 parts by mass of the alkali-soluble resin.
- solvents for photoresist compositions include ketones such as acetone, methyl ethyl ketone, cyclohexanone, cyclopentanone, cycloheptanone, 2-heptanone, methyl isobutyl ketone, butyrolactone; methanol, ethanol, n-propyl alcohol, iso - alcohols such as propyl alcohol, n-butyl alcohol, iso-butyl alcohol, tert-butyl alcohol, pentanol, heptanol, octanol, nonanol, decanol; ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dioxane; Alcohol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene
- the coating composition of the present invention When the coating composition of the present invention is used as a color resist composition, the color resist composition contains an alkali-soluble resin, a polymerizable compound, a colorant, etc. in addition to the polymer of the present invention.
- the same alkali-soluble resin as contained in the photoresist composition can be used.
- the polymerizable compound contained in the color resist composition is, for example, a compound having a photopolymerizable functional group capable of polymerizing or cross-linking reaction upon exposure to active energy rays such as ultraviolet rays.
- the polymerizable compound include unsaturated carboxylic acids such as (meth) acrylic acid, esters of monohydroxy compounds and unsaturated carboxylic acids, esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids, aromatic Esters of polyhydroxy compounds and unsaturated carboxylic acids, esters obtained by esterification reactions of unsaturated carboxylic acids with polyvalent carboxylic acids and polyvalent hydroxy compounds such as the aforementioned aliphatic polyhydroxy compounds and aromatic polyhydroxy compounds , a polymerizable compound having a urethane skeleton obtained by reacting a polyisocyanate compound with a (meth)acryloyl group-containing hydroxy compound, and a polymerizable compound having an acid group.
- a polymerizable compound may be used individually by
- esters of the aliphatic polyhydroxy compounds and unsaturated carboxylic acids include ethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethanetri ( meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa (Meth)acrylic acid esters such as (meth)acrylates and glycerol (meth)acrylates can be mentioned.
- the (meth)acrylic acid portion of these acrylates may be replaced with itaconic acid esters, crotonic acid esters replaced with cro
- esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids include hydroquinone di(meth)acrylate, resorcinol di(meth)acrylate, pyrogallol tri(meth)acrylate and the like.
- the ester obtained by the esterification reaction of unsaturated carboxylic acid, polyvalent carboxylic acid and polyvalent hydroxy compound may be a single substance or a mixture.
- esters include, for example, esters obtained from (meth)acrylic acid, phthalic acid and ethylene glycol, esters obtained from (meth)acrylic acid, maleic acid and diethylene glycol, (meth)acrylic acid, terephthalic acid and penta Examples thereof include esters obtained from erythritol, esters obtained from (meth)acrylic acid, adipic acid, butanediol and glycerin.
- Examples of the polymerizable compound having a urethane skeleton obtained by reacting the polyisocyanate compound with the (meth)acryloyl group-containing hydroxy compound include aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; Cyclic diisocyanates; aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate; A reaction product with a hydroxy compound having an acryloyl group can be mentioned.
- the polymerizable compound having an acid group is, for example, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and the unreacted hydroxyl group of the aliphatic polyhydroxy compound is reacted with a non-aromatic carboxylic acid anhydride.
- a polyfunctional polymerizable compound having an acid group is preferred. Pentaerythritol or dipentaerythritol is preferable as the aliphatic polyhydroxy compound used for preparing the polyfunctional polymerizable compound.
- the acid value of the polyfunctional polymerizable compound is preferably in the range of 0.1 to 40, and more preferably in the range of 5 to 30, because good developability, curability and the like are obtained.
- a mixture of polymerizable compounds is preferably within the above range.
- polymerizable compound having an acid group examples include a mixture containing dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate and succinic acid ester of dipentaerythritol pentaacrylate as a main component, and the mixture is Aronix TO. -1382 (manufactured by Toagosei Co., Ltd.).
- polymerizable compounds other than the above examples include (meth)acrylamides such as ethylenebis(meth)acrylamide; allyl esters such as diallyl phthalate; and compounds having a vinyl group such as divinyl phthalate.
- the content of the polymerizable compound is preferably in the range of 5 to 80% by mass, more preferably in the range of 10 to 70% by mass, based on the total solid content of the color resist composition. More preferably, it is in the range of 20 to 50% by mass.
- the coloring agent for the color resist composition is not particularly limited as long as it can be colored, and may be, for example, a pigment or a dye.
- Either an organic pigment or an inorganic pigment can be used as the pigment.
- the organic pigment pigments of each hue such as red pigment, green pigment, blue pigment, yellow pigment, purple pigment, orange pigment and brown pigment can be used.
- Examples of chemical structures of organic pigments include azo-based, phthalocyanine-based, quinacridone-based, benzimidazolone-based, isoindolinone-based, dioxazine-based, indanthrene-based, and perylene-based pigments.
- the inorganic pigment include barium sulfate, lead sulfate, titanium oxide, yellow lead, red iron oxide, and chromium oxide.
- C.I means a color index.
- red pigment for example, C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53: 3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81: 3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 19
- C.I. I. Pigment Red 48:1, 122, 168, 177, 202, 206, 207, 209, 224, 242 or 254 is preferred, C.I. I. Pigment Red 177, 209, 224 or 254 is more preferred.
- C.I. I. Pigment Green 1 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, 58 and the like.
- C.I. I. Pigment Green 7, 36 or 58 are preferred.
- C.I. I. Pigment Blue 1 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like.
- C.I. I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, or 15:6 is preferred, and C.I. I. Pigment Blue 15:6 is more preferred.
- C.I. I. Pigment Yellow 1 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62: 1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95,97,100,101,104,105,108,109,110,111,116,117,119,120,126,127,127:1,128,129,133,134,136,138,139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 19
- C.I. I. Pigment Yellow 83, 117, 129, 138, 139, 150, 154, 155, 180 or 185 is preferred, and C.I. I. Pigment Yellow 83, 138, 139, 150 or 180 is more preferred.
- C.I. I. Pigment Violet 1 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like.
- C.I. I. Pigment Violet 19 or 23 are preferred, C.I. I. Pigment Violet 23 is more preferred.
- C.I. I. Pigment Orange 1 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 61, 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79 and the like.
- C.I. I. Pigment Orange 38 or 71 are preferred.
- each pixel of the three primary colors of the color filter used in the liquid crystal display device and the organic EL display device is red (R), green (G), and blue (B)
- the red pigment, the green pigment and the blue pigment are the main components.
- organic pigments of colors such as yellow, purple, and orange may be used for hue adjustment.
- the average particle size of the organic pigment is preferably 1 ⁇ m or less, more preferably 0.5 ⁇ m or less, and even more preferably 0.3 ⁇ m or less, in order to increase the luminance of color liquid crystal display devices and organic EL display devices. It is preferable to disperse and use the organic pigment so as to obtain these average particle diameters.
- the average primary particle size of the organic pigment is preferably 100 nm or less, more preferably 50 nm or less, still more preferably 40 nm or less, and particularly preferably in the range of 10 to 30 nm.
- the average particle size of the organic pigment is measured by a dynamic light scattering type particle size distribution meter. -EX250” or the like.
- the colorant is not particularly limited as long as it is black, but carbon black, lamp black, acetylene black, bone black, thermal black, channel black, furnace black, graphite, iron black, titanium black and the like.
- carbon black and titanium black are preferable from the viewpoint of light shielding rate and image characteristics.
- two or more kinds of organic pigments may be mixed to obtain a black color by mixing the colors.
- carbon blacks include, for example, MA7, MA8, MA11, MA100, MA100R, MA220, MA230, MA600, #5, #10, #20, #25, #30 and #32 manufactured by Mitsubishi Chemical Corporation. , #33, #40, #44, #45, #47, #50, #52, #55, #650, #750, #850, #950, #960, #970, #980, #990, # 1000, #2200, #2300, #2350, #2400, #2600, #3050, #3150, #3250, #3600, #3750, #3950, #4000, #4010, OIL7B, OIL9B, OIL11B, OIL30B, OIL31B ⁇ Printex3 ⁇ Printex3OP ⁇ Printex30 ⁇ Printex30OP ⁇ Printex40 ⁇ Printex45 ⁇ Printex55 ⁇ Printex60 ⁇ Printex75 ⁇ Printex80 ⁇ Printex85 ⁇ Printex90 ⁇ Printex A ⁇ Print ex L ⁇ Printex G ⁇ Printex P ⁇ Printex U ⁇ Printex V ⁇ PrintexG
- resin-coated carbon black is preferable as it has a high optical density and a high surface resistivity required for the black matrix of color filters.
- titanium black products examples include titanium black 10S, 12S, 13R, 13M, 13M-C manufactured by Mitsubishi Materials Corporation.
- BM black matrix
- two or more organic pigments may be mixed to obtain black by color mixing, and a black pigment obtained by mixing three colors of red, green and blue pigments may be mentioned.
- Coloring materials that can be mixed to prepare black pigments include Victoria Pure Blue (CI 42595), Auramine O (CI 41000), Catilone Brilliant Flavin (Basic 13), Rhodamine 6GCP (C 45160), Rhodamine B (CI 45170), Safranin OK 70:100 (CI 50240), Erioglaucine X (CI 42080), No.
- coloring materials that can be mixed to prepare black pigments include, for example, C.I. I. yellow pigments 20, 24, 86, 93, 109, 110, 117, 125, 137, 138, 147, 148, 153, 154, 166, C.I. I. orange pigments 36, 43, 51, 55, 59, 61, C.I. I. red pigment 9, 97, 122, 123, 149, 168, 177, 180, 192, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, C.I. I. violet pigments 19, 23, 29, 30, 37, 40, 50, C.I. I. blue pigment 15, 15:1, 15:4, 22, 60, 64, C.I. I. green pigment 7, C.I. I. brown pigments 23, 25, 26 and the like;
- the average primary particle size of carbon black is preferably in the range of 0.01 to 0.08 ⁇ m, more preferably in the range of 0.02 to 0.05 ⁇ m because of good developability.
- Carbon black has a particle shape different from that of organic pigments, and exists in a state called a structure in which primary particles are fused to each other, and fine pores may be formed on the particle surface by post-treatment. Therefore, in order to express the particle shape of carbon black, in addition to the average particle diameter of the primary particles obtained by the same method as the organic pigment, the DBP absorption (JIS K6221) and the specific surface area by the BET method ( JIS K6217) is preferably used as an index for the structure and pore volume.
- Dibutyl phthalic acid (hereinafter abbreviated as "DBP") absorption of carbon black is preferably in the range of 40 to 100 cm 3 /100 g, and in the range of 50 to 80 cm 3 /100 g because of good dispersibility and developability. is more preferred.
- the BET specific surface area of carbon black is preferably in the range of 50 to 120 m 2 /g, more preferably in the range of 60 to 95 m 2 /g because of good dispersion stability.
- dyes used as colorants in color resist compositions include azo dyes, anthraquinone dyes, phthalocyanine dyes, quinoneimine dyes, quinoline dyes, nitro dyes, carbonyl dyes, and methine dyes. .
- azo dye for example, C.I. I. Acid Yellow 11, C.I. I. Acid Orange 7, C.I. I. Acid Red 37, C.I. I. Acid Red 180, C.I. I. Acid Blue 29, C.I. I. Direct Red 28, C.I. I. Direct Red 83, C.I. I. Direct Yellow 12, C.I. I. Direct Orange 26, C.I. I. Direct Green 28, C.I. I. Direct Green 59, C.I. I. Reactive Yellow 2, C.I. I. Reactive Red 17, C.I. I. Reactive Red 120, C.I. I. Reactive Black 5, C.I. I. Disperse Orange 5, C.I. I. disperse thread 58, C.I. I. Disperse Blue 165, C.I. I. Basic Blue 41, C.I. I. Basic Red 18, C.I. I. Mordan Tread 7, C.I. I. Mordant Yellow 5, C.I. I. mordant black 7 and the like.
- anthraquinone-based dyes examples include C.I. I. bat blue 4, C.I. I. Acid Blue 40, C.I. I. Acid Green 25, C.I. I. Reactive Blue 19, C.I. I. Reactive Blue 49, C.I. I. disperse thread 60, C.I. I. Disperse Blue 56, C.I. I. Disperse Blue 60 and the like can be mentioned.
- Examples of the phthalocyanine dyes include C.I. I. Pad Blue 5 and the like, and examples of the quinone imine dyes include C.I. I. Basic Blue 3, C.I. I. Basic Blue 9 and the like, and examples of the quinoline dye include C.I. I. Solvent Yellow 33, C.I. I. Acid Yellow 3, C.I. I. Disperse Yellow 64 and the like, and examples of the nitro-based dye include C.I. I. Acid Yellow 1, C.I. I. Acid Orange 3, C.I. I. Examples include Disperse Yellow 42 and the like.
- Pigments are preferably used as the colorant for the color resist composition because the resulting coating film has excellent light resistance, weather resistance and fastness.
- a dye may be used in combination.
- the content of the colorant is preferably 1% by mass or more, more preferably in the range of 5 to 80% by mass, more preferably 5 to 70% by mass, based on the total solid content of the color resist composition. % range is more preferred
- the content of the coloring agent in the color resist composition is It is preferably in the range of 5 to 60% by mass, more preferably in the range of 10 to 50% by mass.
- the content of the coloring agent in the color resist composition is preferably in the range of 20 to 80% by mass based on the total solid content of the color resist composition. , more preferably in the range of 30 to 70% by mass.
- the colorant when it is a pigment, it is preferably used as a pigment dispersion prepared by dispersing the pigment in an organic solvent using a dispersant.
- the dispersant include surfactants; intermediates or derivatives of pigments; intermediates or derivatives of dyes; resin type dispersants such as polyamide resins, polyurethane resins, polyester resins and acrylic resins.
- resin type dispersants such as polyamide resins, polyurethane resins, polyester resins and acrylic resins.
- a nitrogen atom-containing graft copolymer, a nitrogen atom-containing acrylic block copolymer, a urethane resin dispersant, and the like are preferable.
- these dispersants have nitrogen atoms, the nitrogen atoms have an affinity for the pigment surface, and the portion other than the nitrogen atoms increases the affinity for the medium, thereby improving the dispersion stability.
- These dispersants may be used singly or in combination of two or more.
- Efca series (“Efca 46" etc.) manufactured by BASF; "Disperbyk” series and “BYK” series ("BYK-160", “BYK” -161", “BYK-2001”, etc.); Nippon Lubrizol Co., Ltd.'s “Solspers” series; Shin-Etsu Chemical Co., Ltd.'s "KP” series; Kyoeisha Chemical Co., Ltd.'s "Polyflow” series; Kusumoto Kasei Co., Ltd. "Disparon” series manufactured by the company; "Ajisper” series manufactured by Ajinomoto Fine-Techno Co., Ltd. ("Ajisper PB-814" etc.);
- Organic solvents used in the preparation of the pigment dispersion include, for example, acetic acid ester solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate; propionate solvents such as ethoxypropionate; toluene and xylene.
- Examples of the method for preparing the pigment dispersion include a method in which a colorant is kneaded and dispersed and a fine dispersion step, and a method in which only a fine dispersion step is performed.
- the colorant, part of the alkali-soluble resin, and, if necessary, the dispersant are mixed and kneaded.
- the colorant can be dispersed by using a kneader to disperse while applying a strong shearing force.
- Machines used for kneading include two rolls, three rolls, ball mills, tron mills, dispersers, kneaders, co-kneaders, homogenizers, blenders, single-screw or twin-screw extruders, and the like. It is preferable that the particle size of the coloring agent is made fine by salt milling or the like before kneading.
- a solvent is added to the composition containing the coloring agent obtained in the kneading and dispersing step, or a mixture of a coloring agent, an alkali-soluble resin, a solvent and, if necessary, the dispersant is mixed.
- the average particle size of the primary particles of the colorant is preferably 10 to 100 nm, more preferably 10 to 60 nm.
- the average particle size of the colorant is measured by a dynamic light scattering type particle size distribution meter. -EX250” or the like.
- coating compositions As described above, coating compositions, photoresist compositions, and color resist compositions have been exemplified as coating compositions, but are not limited to these.
- liquid crystal displays hereinafter abbreviated as “LCD”
- PDP plasma displays
- organic EL displays hereinafter abbreviated as “OLED ”
- anti-glare (AG: anti-glare) hard coating material anti-reflection (LR) coating material
- low Refractive index layer coating material high refractive index layer coating material
- clear hard coating material polymerizable liquid crystal coating material
- each pixel such as RGB of a color filter (hereinafter abbreviated as "CF")
- CF color filter
- black resists, inkjet inks, printing inks or paints for forming black matrices, black column spacers, black photospacers of CFs such as LCDs; used in CFs such as LCDs coating for transparent protective film to protect the surface of CFs; liquid crystal materials for LCDs, column spacers, resin compositions
- the polymer of the present invention Since the polymer of the present invention has an excellent ability to reduce surface tension, it exhibits not only leveling properties, but also wettability, penetrability, washability, water repellency, oil repellency, antifouling properties, lubricity, and antiblocking properties. , mold releasability can also be expected. Further, when the polymer of the present invention is blended in a paint or coating agent containing fine particles, it can be expected to improve the dispersibility of the fine particles and not only provide leveling properties but also function as a fine particle dispersant.
- the polymer of the present invention is added to an adhesive composition used for adhesive tapes and the like in addition to the above coating composition, so that not only leveling properties but also reduction of peel force, suppression of fluctuation of peel force, peeling Each function of suppression of electrification can also be expected.
- the weight average molecular weight (Mw) and number average molecular weight (Mn) are polystyrene-equivalent values based on gel permeation chromatography (GPC) measurement.
- GPC gel permeation chromatography
- Example 1 Synthesis of (silicone/polyester) living block copolymer
- methyl ethyl ketone as a solvent
- 16.5 g of a polyester chain-containing monomer represented below were charged, and the temperature was raised to 50° C. while stirring under a nitrogen stream.
- 37 g of 2,2'-bipyridyl and 1.3 g of cuprous chloride were charged, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 50°C.
- 2.3 g of ethyl 2-bromoisobutyrate was added and reacted at 50° C.
- the weight average molecular weight (Mw) was 14,000
- the number average molecular weight (Mn) was 11,000
- (Mw/Mn) was 1.0.
- the content of the functional group represented by —Si[OSi(CH 3 ) 3 ] 3 in the silicone chain-containing polymer (1) was 49% by mass based on the ratio of raw materials charged.
- Example 2 Synthesis of (silicone/polyester) random copolymer
- a nitrogen-purged flask was charged with 1,352 g of butyl acetate as a solvent, and the temperature was raised to 90° C. while stirring under a nitrogen stream.
- 67.0 g of 3-methacryloyloxypropyltris(trimethylsiloxy)silane, 33.0 g of the same polyester chain-containing monomer as in Example 1, and 3.0 g of t-butylperoxy-2-ethylhexanoate as a polymerization initiator. was dissolved in 98.1 g of butyl acetate, and was added dropwise over 2 hours while maintaining the inside of the flask at 90°C. After completion of the dropwise addition, reaction was carried out at 90° C. for 7 hours under a nitrogen stream to obtain a silicone chain-containing polymer (2).
- the weight average molecular weight (Mw) was 21,000
- the number average molecular weight (Mn) was 5,800
- the (Mw/Mn) was 3.0. was 5.
- the content of the functional group represented by —Si[OSi(CH 3 ) 3 ] 3 in the silicone chain-containing polymer (2) was 49% by mass based on the ratio of raw materials charged.
- Example 3 Synthesis of (silicone/polyester) random copolymer
- the weight average molecular weight (Mw) was 21,000
- the number average molecular weight (Mn) was 5,800
- the (Mw/Mn) was 3.0.
- the content ratio of the polymerizable unsaturated monomer having a silicone chain in the silicone chain-containing polymer (3) was 20% by mass based on the raw material charging ratio.
- the value of x is a value calculated by 29 Si NMR analysis.
- the molecular weight of the obtained silicone chain-containing polymer (1′) was measured by GPC, and the weight average molecular weight (Mw) was 10,300, the number average molecular weight (Mn) was 7,900, and (Mw/Mn) was 1. .3.
- the content of the functional group represented by —Si[OSi(CH 3 ) 3 ] 3 in the silicone chain-containing polymer (1′) was 49% by mass based on the raw material charging ratio.
- the molecular weight of the obtained silicone chain-containing polymer (2′) was measured by GPC, and the weight average molecular weight (Mw) was 6,000, the number average molecular weight (Mn) was 2,500, and (Mw/Mn) was 2. .4. Moreover, the content of the functional group represented by —Si[OSi(CH 3 ) 3 ] 3 in the silicone chain-containing polymer (2′) was 49% by mass based on the raw material charging ratio.
- the molecular weight of the obtained silicone chain-containing polymer (3′) was measured by GPC, and the weight average molecular weight (Mw) was 5,000, the number average molecular weight (Mn) was 2,000, and (Mw/Mn) was 2. .5. Moreover, the content ratio of the polymerizable unsaturated monomer having a silicone chain in the silicone chain-containing polymer (3') was 29% by mass based on the ratio of raw materials charged.
- a coating film was formed as follows. Alkali-soluble resin 40% by mass resin solution (Acrydic ZL-295, manufactured by DIC Corporation) 3.0 g, Aronix M-402 (manufactured by Toagosei Chemical Co., Ltd., a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate ), 0.001 g of silicone chain-containing polymer (1) in terms of solid content, and 3.8 g of propylene glycol monomethyl ether acetate (PGMEA) were mixed to prepare a composition.
- Alkali-soluble resin 40% by mass resin solution Alkali-soluble resin 40% by mass resin solution (Acrydic ZL-295, manufactured by DIC Corporation) 3.0 g, Aronix M-402 (manufactured by Toagosei Chemical Co., Ltd., a mixture of dipentaerythritol pentaacrylate and dipentaerythritol he
- the smoothness and coating film defects of the coating film layer of the produced laminate were evaluated by the following methods. Table 1 shows the results. (Smoothness) The coating layer of the obtained laminate was visually observed, and the smoothness of the coating layer was evaluated according to the following criteria. AA: No coating film unevenness is observed. A: Almost no coating film unevenness is observed. B: Some coating film unevenness is observed. C: Coating film unevenness is observed on the whole.
- Example 1 The same evaluation as in Example 1 was performed except that the polymers produced in Examples 2 and 3 and Comparative Examples 1 to 3 were used instead of the silicone chain-containing polymer (1). Table 1 shows the results.
- compositions of Examples 1 to 3 containing a copolymer of a polymerizable monomer having a silicone group and a polymerizable monomer having a polyester chain exhibited smoothness of the coating film. It can be seen that it is superior to On the other hand, it can be seen that the compositions of Comparative Examples 1 to 3, which contain copolymers having silicone groups but no polyester chains, have insufficient smoothness of coating films.
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Abstract
Description
自動車用塗料に用いるレベリング剤としては、シリコーン系レベリング剤が提案されている(特許文献1及び2)。
レベリング剤をカラーレジスト組成物に添加することで、得られる塗膜の平滑性を向上し、赤(R)、緑(G)、青(B)の画素、及び、これら画素間に形成されたブラックマトリックス(BM)の表面が高い平滑性を示すことができ、色ムラの少ないカラーフィルターとすることができる。
本願明細書において「(メタ)アクリレート」とは、アクリレートとメタクリレートの一方又は両方を意味する。
本発明のシリコーン鎖含有重合体(以下、単に「本発明の重合体」という場合がある)は、下記一般式(A)で表される基を有する重合性単量体(1)と、ポリエステル鎖を含む基を有する重合性単量体(2)とを少なくとも重合成分とする重合体である。
R11は、それぞれ独立に、炭素原子数1~6のアルキル基又は-OSi(R14)3で表される基(R14はそれぞれ独立に炭素原子数1~3のアルキル基)であり、
R12は、それぞれ独立に、炭素原子数1~6のアルキル基であり、
R13は、炭素原子数1~6のアルキル基であり、
xは0以上の整数である。)
R11、R12、R13及びxは、それぞれ前記一般式(A)のR11、R12、R13及びxと同じであり、
R15は水素原子又はメチル基であり、
L1は2価の有機基又は単結合である。)
L1の炭素原子数1~50のアルキレンオキシ基は、好ましくは炭素原子数1~15のアルキレンオキシ基であり、より好ましくは炭素原子数1~8のアルキレンオキシ基であり、さらに好ましくはメチレンオキシ基、エチレンオキシ基、プロピレンオキシ基、オキシトリメチレン基、ブチレンオキシ基、オキシテトラメチレン基、ペンチレンオキシ基、ヘプチレンオキシ基又はオクチレンオキシ基である。
重合性単量体(1)の具体例としては、α-(3-メタクリロイルオキシ)プロピルポリジメチルシロキサン、3-(メタクリロイルオキシ)プロピルトリス(トリメチルシロキシ)シラン等が挙げられる。
R21は水素原子、炭素原子数1~18のアルキル基、又は炭素原子数1~18のエーテル結合を有するアルキル基であり、
pは1~30の範囲の整数であり、qは2以上の整数である。)
尚、qの数平均値はGPCチャートから読み取ることができる。
R21、p及びqは、前記一般式(B-1)及び(B-2)のR21、p及びqと同じであり、
L2は2価の有機基又は単結合であり、
R22は水素原子又はメチル基である。)
ここでポリオキシアルキレン鎖を含む基とは、オキシアルキレンの繰り返し部分を含む2価の連結基である。
例えば後述する一般式(3-2)で表される化合物をラクトン変性することで前記一般式(2-1)で表される化合物が得られる。
本発明の重合体は、重合性単量体(1)と重合性単量体(2)のランダム共重合体でもよく、重合性単量体(1)と重合性単量体(2)のブロック共重合体でもよく、好ましくは重合性単量体(1)と重合性単量体(2)のブロック共重合体である。
本発明の重合体が重合性単量体(1)と重合性単量体(2)のブロック共重合体である場合、重合性単量体(1)の重合体ブロックと重合性単量体(2)の重合体ブロックの数および結合順序は特に限定されず、例えば重合性単量体(1)の重合体ブロックと重合性単量体(2)の重合体ブロックが結合したジブロック共重合体でもよい。
同様に、重合成分において重合性単量体(2)は、1種単独の重合性単量体(2)でもよく、互いに構造が異なる2種以上の重合性単量体(2)でもよい。
重合性単量体(1)の含有割合は、本発明の重合体を製造する際の重合性単量体(1)の原料仕込み比により調整できる。
重合性単量体(2)の含有割合は、本発明の重合体を製造する際の重合性単量体(2)の原料仕込み比により調整できる。
前記一般式(A)で表される基の含有割合は、本発明の重合体を製造する際に用いる重合性単量体(1)の原料仕込み比により調整できる。
ここで「実質的になる」とは、重合成分における重合性単量体(1)と重合性単量体(2)の合計の含有割合が、例えば80質量%以上、90質量%以上、95質量%以上又は98質量%以上であることを意味する。
重合性単量体(3)が有する炭素原子数1~18のアルキル基は、例えば炭素原子数1~18のヒドロキシアルキル基、炭素原子数7~18のフェニルアルキル基、炭素原子数7~18のフェノキシアルキル基を含む。
重合性単量体(3)が有する炭素原子数1~18のアルキル基は、好ましくは炭素原子数1~8のアルキル基である。
重合性単量体(3)が有する炭素原子数6~18の芳香族基は、さらに水酸基、アルキル基、アルコキシ等の置換基が置換していてもよく、例えば炭素原子数1~6のアルキル基が置換したフェニル基を含む。
尚、上記「ポリ(エチレングリコール・プロピレングリコール)」は、エチレングリコールとプロピレングリコールとのランダム共重合物を意味し、「ポリエチレングリコール・ポリプロピレングリコール」は、エチレングリコールとプロピレングリコールとのブロック共重合物を意味する。
R31は炭素原子数1~18のアルキル基であり、
R32は水素原子又はメチル基であり、
R33は水素原子又は炭素原子数1~18のアルキル基であり、
R34は水素原子又はメチル基であり、
nは1~4の範囲の整数であり、mは1~200の範囲の整数である。)
前記一般式(3-2)において、mは好ましくは2~50の範囲の整数であり、より好ましくは3~20の範囲の整数である。
また、重合性単量体(3)は、市販品を用いてもよい。例えばポリオキシアルキレン鎖を含む基を有し、重合性不飽和基が(メタ)アクリロイル基である重合性単量体(3-2)の市販品として、新中村化学工業株式会社製の「NKエステルM-20G」、「NKエステルM-40G」、「NKエステルM-90G」、「NKエステルM-230G」、「NKエステルAM-90G」、「NKエステルAMP-10G」、「NKエステルAMP-20G」、「NKエステルAMP-60G」、日油株式会社製の「ブレンマーPE-90」、「ブレンマーPE-200」、「ブレンマーPE-350」、「ブレンマーPME-100」、「ブレンマーPME-200」、「ブレンマーPME-400」、「ブレンマーPME-4000」、「ブレンマーPP-1000」、「ブレンマーPP-500」、「ブレンマーPP-800」、「ブレンマー70PEP-350B」、「ブレンマー55PET-800」、「ブレンマー50POEP-800B」、「ブレンマー10PPB-500B」、「ブレンマーNKH-5050」、「ブレンマーAP-400」、「ブレンマーAE-350」等が挙げられる。
本発明において「反応性官能基」とは、他の官能基と反応して架橋構造等を形成しうる官能基であり、イソシアネート基、エポキシ基、カルボキシル基、カルボン酸ハライド基、カルボン酸無水物基等が挙げられる。
本発明の重合体の重量平均分子量(Mw)は、好ましくは1,000~500,000の範囲であり、より好ましくは2,000~100,000の範囲であり、さらに好ましくは5,000~40,000の範囲である。
本発明の重合体の分散度(Mw/Mn)は、例えば5.0以下であり、好ましくは3.0以下であり、より好ましくは2.0以下であり、さらに好ましくは1.5以下である。分散度の下限は特に制限されないが例えば1.0である。
本発明の重合体の数平均分子量(Mn)及び重量平均分子量(Mw)の値は、実施例に記載の方法により測定する。
本発明の重合体の製造方法は特に限定されず、公知の方法により製造することができる。
本発明の重合体は、ラジカル重合法、カチオン重合法、アニオン重合法等の重合機構に基づき、重合成分を溶液重合法、塊状重合法、エマルジョン重合法等により製造できる。例えばラジカル重合法であれば、有機溶媒中に重合成分を仕込み、汎用のラジカル重合開始剤を添加することで、本発明の重合体を製造できる。
上記で得られる重合体は、ランダム共重合体である。
必要に応じて、ラウリルメルカプタン、2-メルカプトエタノール、エチルチオグリコール酸、オクチルチオグリコール酸等の連鎖移動剤や、γ-メルカプトプロピルトリメトキシシラン等のカップリング基を有するチオール化合物を連鎖移動剤等の添加剤として用いてもよい。
これら溶剤は、1種単独で用いることも2種以上併用することもできる。
上記で得られる重合体は、ブロック共重合体である。
炭素原子数1~6の2-ハロゲン化カルボン酸の炭素原子数1~6のアルキルエステルのより具体的な例としては、例えば、2-クロロプロピオン酸メチル、2-クロロプロピオン酸エチル、2-ブロモプロピオン酸メチル、2-ブロモイソ酪酸エチル等が挙げられる。
Mn+Xnで表される遷移金属化合物の遷移金属Mn+としては、Cu+、Cu2+、Fe2+、Fe3+、Ru2+、Ru3+、Cr2+、Cr3+、Mo0、Mo+、Mo2+、Mo3+、W2+、W3+、Rh3+、Rh4+、Co+、Co2+、Re2+、Re3+、Ni0、Ni+、Mn3+、Mn4+、V2+、V3+、Zn+、Zn2+、Au+、Au2+、Ag+及びAg2+からなる群から選択することができる。
Mn+Xnで表される遷移金属化合物のXは、ハロゲン原子、炭素原子数1~6のアルコキシル基、(SO4)1/2、(PO4)1/3、(HPO4)1/2、(H2PO4)、トリフラート、ヘキサフルオロホスフェート、メタンスルホネート、アリールスルホネート(好ましくはベンゼンスルホネート又はトルエンスルホネート)、SeR11、CN及びR12COOからなる群から選択することができる。ここで、R11は、アリール基、直鎖状又は分岐状の炭素原子数1~20(好ましくは炭素原子数1~10)のアルキル基を表し、R12は、水素原子、ハロゲンで1~5回(好適にはフッ素もしくは塩素で1~3回)置換されていてもよい直鎖状又は分岐状の炭素原子数1~6のアルキル基(好ましくはメチル基)を表す。
Mn+Xnで表される遷移金属化合物のnは、金属上の形式電荷を表し、0~7の整数である。
リビングラジカル重合で使用する溶媒としては、例えば、酢酸エチル、酢酸ブチル、プロピレングリコールモノメチルエーテルアセテート等のエステル系溶媒;ジイソプロピルエーテル、ジメトキシエタン、ジエチレングリコールジメチルエーテル等のエーテル系溶媒;ジクロロメタン、ジクロロエタン等のハロゲン系溶媒;トルエン、キシレン、アニソール等の芳香族系溶媒;メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶剤;メタノール、エタノール、イソプロパノール等のアルコール系溶剤;ジメチルホルムアミド、ジメチルスルホキシド等の非プロトン性極性溶媒などが挙げられる。
上記溶媒は、1種単独で用いてもよく2種以上を併用してもよい。
方法1:重合開始剤、遷移金属化合物、該遷移金属と配位結合可能な配位子化合物及び溶媒の存在下で、重合性単量体(1)と重合性単量体(2)とをリビングラジカル重合(好ましくは原子移動ラジカル重合)させる方法。
方法2:重合開始剤、遷移金属化合物、該遷移金属と配位結合可能な配位子化合物及び溶媒の存在下で、重合性単量体(1)をリビングラジカル重合(好ましくは原子移動ラジカル重合)させ、重合性単量体(1)の重合体ブロックを得た後、重合性単量体(2)を反応系に加えて重合性単量体(1)の重合体ブロックにさらに重合性単量体(2)をリビングラジカル重合(好ましくは原子移動ラジカル重合)させる方法。
方法3:重合開始剤、遷移金属化合物、該遷移金属と配位結合可能な配位子化合物及び溶媒の存在下で、重合性単量体(2)をリビングラジカル重合(好ましくは原子移動ラジカル重合)させ、重合性単量体(2)の重合体ブロックを得た後、重合性単量体(1)を反応系に加えて重合性単量体(2)の重合体ブロックにさらに重合性単量体(1)をリビングラジカル重合(好ましくは原子移動ラジカル重合)させる方法。
本発明の重合体は、コーティング組成物のレベリング剤として好適に用いることができ、本発明のコーティング組成物は本発明の重合体を含む。本発明の重合体はフッ素原子を含まないフッ素原子フリーなレベリング剤とすることができるので、環境に対する蓄積性が低い環境負荷の小さいレベリング剤である。
上記塗料用組成物に本発明の重合体を添加することで、得らえれる塗膜に平滑性を付与することができる。
感光性樹脂組成物の中でも、レジスト組成物(フォトレジスト組成物、カラーフィルター用のカラーレジスト組成物等)は、高度なレベリング性が要求される。レジスト組成物は、通常、スピンコーティングによって、シリコンウェハー上又は各種金属を蒸着したガラス基板上に厚さが1~2μm程度になるように塗布される。この際、塗布膜厚が振れたり、塗布ムラが発生したりすると、パターンの直線性や再現性が低下し、目的とする精度を有するレジストパターンが得られないという問題が生じる。また、これら問題以外にも滴下跡、全体ムラ、中心部に比較しエッジ部が膜厚化するビード現象等の様々なレベリングに関与する問題もある。
本発明のコーティング組成物は、本発明の重合体が高度なレベリング性を発揮して均一な塗膜(硬化物)を形成することができるため、レジスト組成物として用いた場合に上記のような問題を解決することができる。
アルカリ可溶性樹脂としては、例えば、フェノール、クレゾール、キシレノール、レゾルシノール、フロログリシノール、ハイドロキノン等の芳香族ヒドロキシ化合物誘導体とホルムアルデヒド、アセトアルデヒド、ベンズアルデヒド等のアルデヒド化合物とを縮合して得られるノボラック樹脂;o-ビニルフェノール、m-ビニルフェノール、p-ビニルフェノール、α-メチルビニルフェノール等のビニルフェノール化合物誘導体の重合体又は共重合体;アクリル酸、メタクリル酸、ヒドロキシエチル(メタ)アクリレート等の(メタ)アクリル酸系重合体又は共重合体;ポリビニルアルコール;これら各種樹脂の水酸基の一部を介してキノンジアジド基、ナフトキノンアジド基、芳香族アジド基、芳香族シンナモイル基等の放射性線感応性基を導入した変性樹脂;分子中にカルボン酸、スルホン酸等の酸性基を含むウレタン樹脂等が挙げられる。
これらアルカリ可溶性樹脂は、1種単独で用いてもよく、2種以上を併用してもよい。
放射線感応性物質としては、例えば、キノンジアジド系化合物、ジアゾ系化合物、アジド系化合物、オニウム塩化合物、ハロゲン化有機化合物、ハロゲン化有機化合物と有機金属化合物との混合物、有機酸エステル化合物、有機酸アミド化合物、有機酸イミド化合物、ポリ(オレフィンスルホン)化合物等が挙げられる
上記の他、トリス(2,3-ジブロモプロピル)ホスフェート、トリス(2,3-ジブロモ-3-クロロプロピル)ホスフェート、クロロテトラブロモメタン、ヘキサクロロベンゼン、ヘキサブロモベンゼン、ヘキサブロモシクロドデカン、ヘキサブロモビフェニル、トリブロモフェニルアリルエーテル、テトラクロロビスフェノールA、テトラブロモビスフェノールA、ビス(ブロモエチルエーテル)テトラブロモビスフェノールA、ビス(クロロエチルエーテル)テトラクロロビスフェノールA、トリス(2,3-ジブロモプロピル)イソシアヌレート、2,2-ビス(4-ヒドロキシ-3,5-ジブロモフェニル)プロパン、2,2-ビス(4-ヒドロキシエトキシ-3,5-ジブロモフェニル)プロパン等のハロゲン系難燃剤として使用されている化合物、ジクロロフェニルトリクロロエタン等の有機クロロ系農薬として使用されている化合物等もハロゲン化有機化合物として例示される。
放射線感応性物質は、1種単独で用いてもよく2種以上を併用してもよい。
これらの溶剤は、1種単独で用いてもよく、2種以上を併用してもよい。
上記の重合性化合物としては、例えば、(メタ)アクリル酸等の不飽和カルボン酸、モノヒドロキシ化合物と不飽和カルボン酸とのエステル、脂肪族ポリヒドロキシ化合物と不飽和カルボン酸とのエステル、芳香族ポリヒドロキシ化合物と不飽和カルボン酸とのエステル、不飽和カルボン酸と多価カルボン酸及び前述の脂肪族ポリヒドロキシ化合物、芳香族ポリヒドロキシ化合物等の多価ヒドロキシ化合物とのエステル化反応により得られるエステル、ポリイソシアネート化合物と(メタ)アクリロイル基含有ヒドロキシ化合物とを反応させたウレタン骨格を有する重合性化合物、酸基を有する重合性化合物等が挙げられる。
重合性化合物は1種単独で用いてもよく、2種以上を併用してもよい。
また、これらアクリレートの(メタ)アクリル酸の部分を、イタコン酸に代えたイタコン酸エステル、クロトン酸に代えたクロトン酸エステル、或いは、マレイン酸に代えたマレイン酸エステル等も挙げられる。
不飽和カルボン酸、多価カルボン酸及び多価ヒドロキシ化合物のエステル化反応により得られるエステルは、単一物であっても、混合物であってもよい。このようなエステルとしては、例えば、(メタ)アクリル酸、フタル酸及びエチレングリコールから得られるエステル、(メタ)アクリル酸、マレイン酸及びジエチレングリコールから得られるエステル、(メタ)アクリル酸、テレフタル酸及びペンタエリスリトールから得られるエステル、(メタ)アクリル酸、アジピン酸、ブタンジオール及びグリセリンから得られるエステル等が挙げられる。
前記多官能重合性化合物の酸価は、現像性、硬化性等が良好となることから、0.1~40の範囲が好ましく、5~30の範囲がより好ましい。酸基を有する多官能重合性化合物を2種以上併用する場合、および酸基を有する多官能重合性化合物と酸基を有しない多官能重合性化合物を併用する場合には、重合性化合物の混合物の酸価が上記の範囲内になるようにすることが好ましい。
顔料は有機顔料、無機顔料のいずれであっても用いることができる。前記有機顔料としては、赤色顔料、緑色顔料、青色顔料、黄色顔料、紫色顔料、オレンジ顔料、ブラウン顔料等の各色相の顔料を使用することができる。また、有機顔料の化学構造としては、例えば、アゾ系、フタロシアニン系、キナクリドン系、ベンツイミダゾロン系、イソインドリノン系、ジオキサジン系、インダンスレン系、ペリレン系等が挙げられる。また、前記無機顔料としては、例えば、硫酸バリウム、硫酸鉛、酸化チタン、黄色鉛、ベンガラ、酸化クロム等が挙げられる。
尚、下記の「C.I.」は、カラーインデックスを意味する。
前記有機顔料の平均一次粒径は、100nm以下が好ましく、50nm以下がより好ましく、40nm以下がさらに好ましく、10~30nmの範囲が特に好ましい。
尚、有機顔料の平均粒径は、動的光散乱式の粒度分布計で測定したものであり、例えば、日機装株式会社製のナノトラック(Nanotrac)粒度分布測定装置「UPA-EX150」、「UPA-EX250」等で測定することができる。
また、2種以上の有機顔料を混合し、混色により黒色とした組み合わせでも構わない。
黒色顔料を調製するために混合使用可能な色材としては、ビクトリアピュアブルー(C.I.42595)、オーラミンO(C.I.41000)、カチロンブリリアントフラビン(ベーシック13)、ローダミン6GCP(C.I.45160)、ローダミンB(C.I.45170)、サフラニンOK70:100(C.I.50240)、エリオグラウシンX(C.I.42080)、No.120/リオノールイエロー(C.I.21090)、リオノールイエローGRO(C.I.21090)、シムラーファーストイエロー8GF(C.I.21105)、ベンジジンイエロー4T-564D(C.I.21095)、シムラーファーストレッド4015(C.I.12355)、リオノールレッド7B4401(C.I.15850)、ファーストゲンブルーTGR-L(C.I.74160)、リオノールブルーSM(C.I.26150)、リオノールブルーES(C.I.ピグメントブルー15:6)、リオノーゲンレッドGD(C.I.ピグメントレッド168)、リオノールグリーン2YS(C.I.ピグメントグリーン36)等が挙げられる。
カーボンブラックのジブチルフタル酸(以下、「DBP」と略記する。)吸収量は、40~100cm3/100gの範囲が好ましく、分散性・現像性が良好なことから50~80cm3/100gの範囲がより好ましい。カーボンブラックのBET法による比表面積は50~120m2/gの範囲が好ましく、分散安定性が良好なことから60~95m2/gの範囲がより好ましい。
前記分散剤としては、界面活性剤;顔料の中間体もしくは誘導体;染料の中間体もしくは誘導体;ポリアミド系樹脂、ポリウレタン系樹脂、ポリエステル系樹脂、アクリル系樹脂等の樹脂型分散剤等が挙げられる。これらの中でも、窒素原子を有するグラフト共重合体、窒素原子を有するアクリル系ブロック共重合体、ウレタン樹脂分散剤等が好ましい。これらの分散剤は、窒素原子を有しているため、窒素原子が顔料表面に対して親和性をもち、窒素原子以外の部分が媒質に対する親和性を高めることにより、分散安定性が向上する。
これら分散剤は、1種単独で用いてもよく、2種以上を併用してもよい。
これらの溶剤は、1種単独で用いてもよく、2種以上を併用してもよい。
混練に用いる機械としては、二本ロール、三本ロール、ボールミル、トロンミル、ディスパー、ニーダー、コニーダー、ホモジナイザー、ブレンダー、単軸もしくは二軸の押出機等が挙げられる。
着色剤は、上記の混練を行う前に、ソルトミリング法等によって粒子サイズを微細化しておくことが好ましい。
尚、本発明は下記実施例に限定されない。
GPCの測定条件は以下の通りである。
測定装置:東ソー株式会社製高速GPC装置「HLC-8420GPC」
カラム:東ソー株式会社製「TSK GUARDCOLUMN SuperHZ-L」+東ソー株式会社製「TSK gel SuperHZM-N」+東ソー株式会社製「TSK gel SuperHZM-N」+東ソー株式会社製「TSK gel SuperHZM-N」+東ソー株式会社製「TSK gel SuperHZM-N」
検出器:RI(示差屈折計)
データ処理:東ソー株式会社製「EcoSEC Data Analysis バージョン1.07」
カラム温度:40℃
展開溶媒:テトラヒドロフラン
流速:0.35mL/分
測定試料:試料7.5mgを10mlのテトラヒドロフランに溶解し、得られた溶液をマイクロフィルターでろ過したものを測定試料とした。
試料注入量:20μl
標準試料:前記「HLC-8420GPC」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A-300」
東ソー株式会社製「A-500」
東ソー株式会社製「A-1000」
東ソー株式会社製「A-2500」
東ソー株式会社製「A-5000」
東ソー株式会社製「F-1」
東ソー株式会社製「F-2」
東ソー株式会社製「F-4」
東ソー株式会社製「F-10」
東ソー株式会社製「F-20」
東ソー株式会社製「F-40」
東ソー株式会社製「F-80」
東ソー株式会社製「F-128」
東ソー株式会社製「F-288」
窒素置換したフラスコに、溶剤としてメチルエチルケトン66.0gと、下記で表されるポリエステル鎖含有モノマー16.5gを仕込み、窒素気流下にて攪拌しながら50℃に昇温した。次いで、2,2’-ビピリジル37g、塩化第一銅1.3gを仕込み、フラスコ内を50℃に保ちながら30分撹拌した。その後、2-ブロモイソ酪酸エチル2.3gを加え、窒素気流下、50℃で6時間反応させ、ε-カプロラクトン変性メタクリレートの重合体ブロックを得た。
次いで、ε-カプロラクトン変性メタクリレートの重合体ブロックを含む反応系に3-メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン33.5g加え、50℃で18時間反応させ、反応物を得た。次いで、得られた反応物に、活性アルミナ30gを加えて攪拌した。活性アルミナを濾過後、溶媒を減圧留去してシリコーン鎖含有重合体(1)を得た。
窒素置換したフラスコに、溶剤として酢酸ブチル1,352gを仕込み、窒素気流下にて攪拌しながら90℃に昇温した。次いで、3-メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン67.0g、実施例1と同じポリエステル鎖含有モノマー33.0g、及び重合開始剤であるt-ブチルペルオキシ-2-エチルヘキサノエート3.0gを酢酸ブチル98.1gに溶解したモノマー重合開始剤溶液を滴下装置にセットし、フラスコ内を90℃に保ちながら2時間かけて滴下した。滴下終了後、窒素気流下、90℃で7時間反応させ、シリコーン鎖含有重合体(2)を得た。
窒素置換したフラスコに、溶剤として酢酸ブチル1,333gを仕込み、窒素気流下にて攪拌しながら90℃に昇温した。次いで、下記で表されるαブチル-ω-(3-メタクリロキシプロピル)ポリジメチルシロキサン20.0g、実施例1と同じポリエステル鎖含有モノマー80.0g、及び重合開始剤であるt-ブチルペルオキシ-2-エチルヘキサノエート3.0gを酢酸ブチル1,000gに溶解したモノマー重合開始剤溶液を滴下装置にセットし、フラスコ内を90℃に保ちながら2時間かけて滴下した。滴下終了後、窒素気流下、90℃で5時間反応させ、シリコーン鎖含有重合体(3)を得た。
尚、xの値は29SiNMR分析により算出した値である。
窒素置換したフラスコに、溶剤としてメチルエチルケトン75.0gと、ポリ1,2-ブチレングリコールモノメタクリレート(1,2-ブチレングリコールの数平均繰り返し数6)16.5gを仕込み、窒素気流下にて攪拌しながら60℃に昇温した。次いで、2,2’-ビピリジル4.2g、塩化第一銅1.5gを仕込み、フラスコ内を60℃に保ちながら30分撹拌した。その後、2-ブロモイソ酪酸エチル2.7gを加え、窒素気流下、60℃で8時間反応させ、ポリ1,2-ブチレングリコールモノメタクリレートの重合体ブロックを得た。
次いで、ポリ1,2-ブチレングリコールモノメタクリレートの重合体ブロックを含む反応系に3-メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン33.5gを加え、60℃で20時間反応させ、反応物を得た。次いで、得られた反応物に、活性アルミナ30gを加えて攪拌した。活性アルミナを濾過後、溶媒を減圧留去してシリコーン鎖含有重合体(1’)を得た。
窒素置換したフラスコに、溶剤として酢酸ブチル133.3gを仕込み、窒素気流下にて攪拌しながら100℃に昇温した。次いで、3-メタクリロイルオキシプロピルトリス(トリメチルシロキシ)シラン67.0g、ポリ1,2-ブチレングリコールモノメタクリレート(1,2-ブチレングリコールの平均繰り返し数6)33.0g、及び重合開始剤であるt-ブチルペルオキシ-2-エチルヘキサノエート6.0gを酢酸ブチル1,000gに溶解したモノマー重合開始剤溶液を滴下装置にセットし、フラスコ内を100℃に保ちながら3時間かけて滴下した。滴下終了後、窒素気流下、100℃で5時間反応させ、シリコーン鎖含有重合体(2’)を得た。
窒素置換したフラスコに、溶剤として酢酸ブチル133.3gを仕込み、窒素気流下にて攪拌しながら110℃に昇温した。次いで、実施例3と同じα-ブチル-ω-(3-メタクリロキシプロピル)ポリジメチルシロキサン30.0g、ポリ1,2-ブチレングリコールモノメタクリレート(1,2-ブチレングリコールの数平均繰り返し数6)70.0g、及び重合開始剤であるt-ブチルペルオキシ-2-エチルヘキサノエート7.5gを酢酸ブチル100.0gに溶解したモノマー重合開始剤溶液を滴下装置にセットし、フラスコ内を110℃に保ちながら2時間かけて滴下した。滴下終了後、窒素気流下、110℃で3時間反応させ、シリコーン鎖含有重合体(3’)を得た。
実施例1で製造したシリコーン鎖含有重合体(1)を用いて以下のようにして塗膜を成膜した。
アルカリ可溶性樹脂40質量%樹脂溶液(アクリディック ZL-295、DIC株式会社製)を3.0g、アロニックスM-402(東亞合成化学株式会社製、ジペンタエリスリトールペンタアクリレートとジペンタエリスリトールヘキサアクリレートの混合物)1.2gと、シリコーン鎖含有重合体(1)を固形分換算で0.001g、プロピレングリコールモノメチルエーテルアセテート(PGMEA)3.8gを混合して組成物を調製した。
得られた組成物3mlを10cm×10cmのクロムメッキガラス基板の中央部分に滴下し、回転数1,000rpm及び回転時間10秒の条件でスピンコ-ティングした後、100℃で100秒間加熱乾燥させて塗膜層を有する積層体を作製した。
(平滑性)
得られた積層体の塗膜層を目視で観察し、下記基準に従って塗膜層の平滑性とを評価した。
AA:塗膜ムラが観察されない。
A:塗膜ムラがほとんど観察されない。
B:塗膜ムラが一部観察される。
C:塗膜ムラが全体に観測される。
Claims (14)
- 前記シリコーン鎖含有重合体中のxの数平均値が1~150の範囲である請求項1~4のいずれかに記載のシリコーン鎖含有重合体。
- 炭素原子数1~18のアルキル基、炭素原子数6~18の芳香族基及びポリオキシアルキレン鎖を含む基から選択される1以上を有する重合性単量体(3)をさらに重合成分とする請求項1~5のいずれかに記載のシリコーン鎖含有重合体。
- 前記重合成分の5~75質量%の範囲で前記重合性単量体(1)を含有する請求項1~7のいずれかに記載のシリコーン鎖含有重合体。
- 前記重合成分の80質量%以上が前記重合性単量体(1)及び前記重合性単量体(2)である請求項1~8のいずれかに記載のシリコーン鎖含有重合体。
- フッ素原子を含まない請求項1~9のいずれかに記載のシリコーン鎖含有重合体。
- 数平均分子量が1,000~500,000の範囲である請求項1~10のいずれかに記載のシリコーン鎖含有重合体。
- 請求項1~11のいずれかに記載のシリコーン鎖含有重合体を含むコーティング組成物。
- 請求項1~11のいずれかに記載のシリコーン鎖含有重合体を含むレジスト組成物。
- 請求項1~11のいずれかに記載のシリコーン鎖含有重合体を用いた物品。
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US8497335B2 (en) * | 2009-07-31 | 2013-07-30 | Kyoeisha Chemical Co., Ltd. | Surface conditioner for coating agents |
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WO2023140036A1 (ja) * | 2022-01-18 | 2023-07-27 | Dic株式会社 | シリコーン鎖含有重合体、シリコーン鎖含有重合体の製造方法、コーティング組成物、レジスト組成物及び物品 |
WO2024101164A1 (ja) * | 2022-11-10 | 2024-05-16 | Dic株式会社 | レジスト組成物およびその硬化物 |
JP7544311B1 (ja) | 2022-11-10 | 2024-09-03 | Dic株式会社 | レジスト組成物およびその硬化物 |
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JP7375983B2 (ja) | 2023-11-08 |
CN117242106A (zh) | 2023-12-15 |
KR20230156116A (ko) | 2023-11-13 |
EP4342920A4 (en) | 2024-10-09 |
US20240263025A1 (en) | 2024-08-08 |
EP4342920A1 (en) | 2024-03-27 |
JPWO2022244586A1 (ja) | 2022-11-24 |
TW202311331A (zh) | 2023-03-16 |
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