WO2023171186A1 - 化合物、当該化合物の製造方法、レベリング剤、コーティング組成物、レジスト組成物及び物品 - Google Patents

化合物、当該化合物の製造方法、レベリング剤、コーティング組成物、レジスト組成物及び物品 Download PDF

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Publication number
WO2023171186A1
WO2023171186A1 PCT/JP2023/003306 JP2023003306W WO2023171186A1 WO 2023171186 A1 WO2023171186 A1 WO 2023171186A1 JP 2023003306 W JP2023003306 W JP 2023003306W WO 2023171186 A1 WO2023171186 A1 WO 2023171186A1
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compound
group
carbon atoms
alkyl group
meth
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PCT/JP2023/003306
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English (en)
French (fr)
Japanese (ja)
Inventor
龍太 藤原
純平 植野
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DIC Corp
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DIC Corp
Dainippon Ink and Chemicals Co Ltd
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Priority to EP23766366.1A priority Critical patent/EP4491648A4/en
Priority to CN202380023020.8A priority patent/CN118742582A/zh
Priority to US18/842,203 priority patent/US20250188226A1/en
Priority to JP2024505948A priority patent/JP7563651B2/ja
Priority to KR1020247022724A priority patent/KR20240157636A/ko
Publication of WO2023171186A1 publication Critical patent/WO2023171186A1/ja
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
    • 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
    • C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • 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
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • 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
    • 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
    • C08F2438/00—Living radical polymerisation
    • C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP

Definitions

  • the present invention relates to a compound, a method for producing the compound, a leveling agent, a coating composition, a resist composition, and an article.
  • a leveling agent is an additive that improves repellency and unevenness of a coating film obtained by applying a coating composition such as a paint 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, lowering the surface tension of the coating film, and smoothing the resulting coating film. A coating film with a smooth surface can reduce the occurrence of repelling and unevenness.
  • Leveling agents have a variety of uses, and 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 applied onto a glass substrate by a coating method such as spin coating or slit coating, and the dried coating film is exposed to light using a mask and then developed to form a colored pattern. It includes a step of forming. At this time, if the smoothness of the coating film is not good and the film thickness is uneven, or if there is uneven coating or repelling, there is a risk that color unevenness will occur in pixels.
  • a leveling agent By adding a leveling agent to the color resist composition, the smoothness of the resulting coating film is improved, and the smoothness of the red (R), green (G), and blue (B) pixels and the areas formed between these pixels are improved.
  • the surface of the black matrix (BM) can exhibit high smoothness, and a color filter with less color unevenness can be obtained.
  • a silicone polymer leveling agent As a leveling agent that provides smoothness to such a coating film, a silicone polymer leveling agent has been proposed (Patent Documents 1 and 2).
  • a coating film obtained by applying a coating composition containing a leveling agent onto a substrate can exhibit high smoothness.
  • This coating film is generally dried in a vacuum drying device to evaporate the solvent in the coating film, and the coating film on the substrate is dried within the drying device chamber while being supported by support pins.
  • a temperature difference occurred between the part where the support pin and the base material abutted and the other part, and unevenness in pins (drying unevenness) occurred due to the difference in drying speed. It was difficult to resolve this unevenness even when a leveling agent was added.
  • a leveling agent that can perform the following functions.
  • the problem to be solved by the present invention is to provide a compound that can function as a leveling agent that provides a coating film with high smoothness and an effect of suppressing unevenness.
  • Another problem to be solved by the present invention is to provide a leveling agent that can impart high smoothness to a coating film even when added in a small amount and can also provide an effect of suppressing pin unevenness.
  • Another problem to be solved by the present invention is to provide a coating composition and a resist composition that can provide a coating film with high smoothness and an effect of suppressing pin unevenness.
  • Another problem to be solved by the present invention is to provide a cured product that has high smoothness and suppresses pin unevenness.
  • a compound has polymer blocks of polymerizable monomers at both ends of the silicone chain and has a degree of dispersion within a specific range, it will form a coating film.
  • the present invention was completed by discovering that it provides high smoothness and suppressing pin unevenness.
  • the present invention relates to a compound having living polymer blocks of polymerizable monomers at both ends of a silicone chain.
  • the present invention can provide a compound that functions as a leveling agent that provides coating films with high smoothness and suppresses unevenness.
  • (meth)acrylate refers to one or both of acrylate and methacrylate.
  • the compound of the present invention is a compound having a polymer block of a polymerizable monomer at both ends of a silicone chain, and has a degree of dispersion (Mw/Mn), which is the ratio of weight average molecular weight to number average molecular weight, of 1. It ranges from 0 to 2.0.
  • Mw/Mn degree of dispersion
  • both ends of the silicone chain means both ends of the main chain of the silicone chain (the longest molecular chain among the molecular chains constituting the silicone chain).
  • the compound of the present invention has a degree of dispersion (Mw/Mn) in the range of 1.0 to 2.0, and is a compound with little variation in molecular weight, so compared to conventional compounds with a high degree of dispersion, it is relatively In addition, the proportion of molecular weight suitable for leveling effect increases. As a result, it is possible to obtain the property that a substance that conventionally requires a large amount to be added in order to exhibit an effect can exhibit its effect with a small amount added.
  • the number average molecular weight of the silicone chain is, for example, in the range of 100 to 50,000, preferably in the range of 500 to 20,000, more preferably in the range of 1,000 to 15,000, even more preferably 1. ,000 to 10,000.
  • the number average molecular weight of silicone chains can be determined by 29 Si NMR analysis.
  • the proportion of the silicone chains is, for example, in the range of 1 to 95% by weight, preferably in the range of 5 to 70% by weight, more preferably in the range of 10 to 65% by weight, even more preferably 20 to 60% by weight. % range.
  • the ratio of silicone chains is a value based on the mass of the compound of the present invention (mass of silicone chains/mass of compound).
  • the proportion of silicone chains is a value calculated from the raw material charging ratio during production, and can be adjusted by the raw material charging ratio of the silicone compound and polymerizable monomer used for producing the compound of the present invention.
  • the silicone chain possessed by the compound of the present invention is preferably a silicone chain represented by the following formula (1).
  • R 11 , R 12 , R 13 and R 14 are each independently an alkyl group having 1 to 18 carbon atoms or a phenyl group.
  • L 11 and L 12 are each independently a divalent organic group or a single bond.
  • n is an integer.
  • the alkyl group having 1 to 18 carbon atoms for R 11 , R 12 , R 13 and R 14 is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group.
  • n is an integer of 2 or more
  • a plurality of R 13s may be the same or different from each other
  • a plurality of R 14s may be the same or different from each other.
  • n is preferably an integer in the range of 5 to 300, more preferably an integer in the range of 10 to 250, even more preferably an integer in the range of 10 to 200, most preferably 40 to 150. is an integer in the range .
  • the divalent organic group of L 11 and L 12 is preferably an alkylene group having 1 to 50 carbon atoms or an alkyleneoxy group having 1 to 50 carbon atoms.
  • Examples of the alkylene group having 1 to 50 carbon atoms for L 11 and L 12 include methylene group, ethylene group, n-propylene group, n-butylene group, n-pentylene group, n-hexylene group, n-heptylene group, Examples include n-octylene group, n-nonylene group, n-decylene group, n-dodecylene group, isopropylene group, 2-methylpropylene group, 2-methylhexylene group, tetramethylethylene group, etc.
  • the alkylene group having 1 to 50 carbon atoms in L 11 and L 12 is preferably an alkylene group having 1 to 15 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, and even more preferably methylene. group, ethylene group, n-propylene group or isopropylene group.
  • the alkyleneoxy group having 1 to 50 carbon atoms as L 11 and L 12 is, for example, a group in which one or more -CH 2 - in the alkylene group is substituted with -O-.
  • the alkyleneoxy group having 1 to 50 carbon atoms in L 11 and L 12 is preferably an alkyleneoxy group having 1 to 15 carbon atoms, more preferably an alkyleneoxy group having 1 to 8 carbon atoms, and Preferred are a methyleneoxy group, an ethyleneoxy group, a propyleneoxy group, an oxytrimethylene group, a butyleneoxy group, an oxytetramethylene group, a pentyleneoxy group, a heptyleneoxy group, or an octyleneoxy group.
  • the carbon atom may be further substituted with a hydroxyl group, etc. .
  • the bond that L 11 and L 12 have is a bond that is bonded directly or via a linking group to the polymer block of the polymerizable monomer.
  • the "polymerizable monomer” means a compound having a polymerizable unsaturated group
  • the "polymer block” refers to the polymerizable monomer described above. A segment consisting of a repeating structure derived from a monomer.
  • Examples of the polymerizable unsaturated group include a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, a vinyl ether group, an allyl group, a styryl group, and a maleimide group.
  • a (meth)acryloyl group and a (meth)acryloyloxy group are preferred because they have good availability of raw materials and good polymerization reactivity.
  • the polymer block of the polymerizable monomer contained in the compound of the present invention is preferably a polymer block of the polymerizable monomer (2) that can exhibit compatibility with the base polymer of the coating composition.
  • the polymerizable monomer (2) is preferably selected from an alkyl group having 1 to 18 carbon atoms, an aromatic group having 6 to 18 carbon atoms, a group containing a polyoxyalkylene chain, and a group containing a polyester chain. It is a polymerizable monomer having one or more.
  • the alkyl group having 1 to 18 carbon atoms in the polymerizable monomer (2) may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group, and specific examples include a methyl group, an ethyl group, and a normal alkyl group. Examples include 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 that the polymerizable monomer (2) has is preferably an alkyl group having 1 to 6 carbon atoms.
  • Examples of the aromatic group having 6 to 18 carbon atoms included in the polymerizable monomer (2) include a phenyl group, a naphthyl group, an anthracen-1-yl group, and a phenanthren-1-yl group.
  • the group containing a (poly)oxyalkylene chain that the polymerizable monomer (2) has is a monovalent group containing a repeating oxyalkylene moiety or a divalent linking group containing a repeating oxyalkylene moiety.
  • the polymerizable unsaturated group possessed by the polymerizable monomer (2) is a (meth)acryloyl group
  • the polymerizable monomer having a group containing a (poly)oxyalkylene chain has the following formula (2-poa1 ) or (2-poa2), preferably a compound represented by the above formula (2-poa1).
  • R a21 each independently represents a hydrogen atom or a methyl group.
  • R a22 is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms.
  • p is an integer greater than or equal to
  • q is an integer greater than or equal to
  • r is an integer greater than or equal to
  • p+q+r is an integer greater than or equal to 1.
  • X, Y and Z are each independently an alkylene group having 1 to 6 carbon atoms.
  • the alkylene groups having 1 to 6 carbon atoms in X, Y, and Z are preferably alkylene groups having 2 to 4 carbon atoms.
  • Examples of the polymerizable monomer (2) having an alkyl group having 1 to 18 carbon atoms and whose polymerizable unsaturated group is a (meth)acryloyl 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 Acrylate, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, stearyl (meth)acrylate
  • Examples of the polymerizable monomer (2) having a phenylalkyl group having 7 to 18 carbon atoms or a phenoxyalkyl group having 7 to 18 carbon atoms and whose polymerizable unsaturated group is a (meth)acryloyl group include, for example: Examples include benzyl (meth)acrylate, phenoxymethyl (meth)acrylate, and 2-phenoxyethyl (meth)acrylate.
  • Examples of the polymerizable monomer (2) having an alkyl group having 1 to 18 carbon atoms and whose polymerizable unsaturated group is a vinyl ether group include methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n - Alkyl vinyl ethers such as 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; cycloalkyl vinyl ethers, etc. It will be done.
  • Examples of the polymerizable monomer (2) having an aromatic group having 6 to 18 carbon atoms include styrene, ⁇ -methylstyrene, p-methylstyrene, p-methoxystyrene, and the like.
  • Examples of the polymerizable monomer (2) having an alkyl group having 1 to 18 carbon atoms and whose polymerizable unsaturated group is a (meth)acryloylamino group include N,N-dimethylacrylamide, N,N- Examples include diethylacrylamide, N-isopropylacrylamide, diacetone acrylamide, acroylmorpholine, and the like.
  • Examples of the polymerizable monomer (2) having an alkyl group having 1 to 18 carbon atoms and whose polymerizable unsaturated group is a maleimide group include methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, hexylmaleimide, Examples include octylmaleimide, dodecylmaleimide, stearylmaleimide, cyclohexylmaleimide, and the like.
  • Examples of the polymerizable monomer (2) having a group containing a polyoxyalkylene chain and whose polymerizable unsaturated group is a (meth)acryloyl 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) 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/pol
  • 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.
  • the polymerizable monomer (2) is preferably a compound represented by the following formula (2-1), a compound represented by the following formula (2-2), or a compound represented by the following formula (2-3). , one or more selected from the group consisting of a compound represented by the following formula (2-4) and a compound represented by the following formula (2-5), more preferably a compound represented by the following formula (2-1). selected from the group consisting of a compound represented by the following formula (2-2), a compound represented by the following formula (2-3), and a compound represented by the following formula (2-4).
  • One or more types. These compounds can exhibit high compatibility when the polymers of the invention are used as leveling agents.
  • R 21 is a hydrogen atom or a methyl group
  • R 22 is an alkyl group having 1 to 18 carbon atoms
  • R 23 is a hydrogen atom or a methyl group
  • R 24 is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms
  • R25 is a hydrogen atom or a methyl group
  • R 26 is an alkyl group having 1 to 18 carbon atoms or an alkyl group having an ether bond having 1 to 18 carbon atoms
  • R 27 is a hydrogen atom or a methyl group
  • R 28 is an alkyl group having 1 to 18 carbon atoms or an alkyl group having an ether bond having 1 to 18 carbon atoms
  • L 2 is a divalent organic group or a single bond
  • R 29 is a hydrogen atom or a methyl group
  • R 30 is each independently an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atom
  • the m n's in parentheses may be the same or different.
  • q p's in parentheses may be the same or different.
  • q p's in parentheses may be the same or different.
  • the divalent organic group of L 2 in formulas (2-3) and (2-4) is the same as the divalent organic group of L 11 .
  • the polymerizable monomer (2) consists of a compound represented by the above formula (2-2), a compound represented by the above formula (2-3), and a compound represented by the above formula (2-4). It is preferable that one or more selected from the group is included.
  • a group consisting of a compound represented by the above formula (2-2), a compound represented by the above formula (2-3), and a compound represented by the above formula (2-4) as the polymerizable monomer (2) A compound represented by the above formula (2-2), a compound represented by the above formula (2-3) based on the total amount of the polymerizable monomer (2), when one or more selected from It is preferable that the total amount of the formula (2-4) is 50% by mass or more.
  • Polymerizable monomer (2) can be produced by a known method. Moreover, a commercially available product may be used as the polymerizable monomer (2).
  • a commercially available polymerizable monomer (2) having a group containing a polyoxyalkylene chain and having a (meth)acryloyl group as a polymerizable unsaturated group "NK Ester M” manufactured by Shin Nakamura Chemical Co., Ltd.
  • the number of polymerizable monomers constituting the polymer block may be one type alone, or two or more types may be used.
  • the polymerization form of the copolymer is not particularly limited, and the polymer block is a copolymer of two or more types of polymerizable monomers having different structures. It may be a random copolymer or a block copolymer of two or more types of polymerizable monomers having mutually different structures.
  • the number average molecular weight (Mn) of the compound of the present invention is preferably in the range of 1,000 to 200,000, more preferably in the range of 1,500 to 50,000, even more preferably in the range of 2,000 to 20,000. ,000 range.
  • the weight average molecular weight (Mw) of the compound of the present invention is preferably in the range of 1,000 to 400,000, more preferably in the range of 2,000 to 100,000, even more preferably 4,000 to 40,000. ,000 range.
  • the number average molecular weight (Mn) and weight average molecular weight (Mw) of the compound of the present invention are measured by the methods described in Examples.
  • the dispersity (Mw/Mn) of the compound of the present invention is in the range of 1.0 to 2.0, preferably in the range of 1.0 to 1.8, more preferably in the range of 1.0 to 1.6. is within the range of In order to bring the degree of dispersion within the above range, it is necessary to carry out living radical polymerization, which will be described later, in the production of the compound, and so-called free radical polymerization cannot bring the degree of dispersion within the above range.
  • the compound of the present invention is produced in a reaction system containing a compound (1) having a functional group capable of generating radicals at both ends of a silicone chain, and a polymerizable monomer (2).
  • the polymerizable monomer (2) can be produced by living radical polymerization of the polymerizable monomer (2) at both ends of the compound (1).
  • the number average molecular weight of the silicone chain possessed by compound (1) is, for example, in the range of 100 to 50,000, preferably in the range of 500 to 20,000, and more preferably in the range of 1,000 to 15,000. , more preferably in the range of 1,000 to 10,000.
  • Examples of the functional group having the radical generating ability of compound (1) include an organic group having a halogen atom, an organic group having an alkyl tellurium group, an organic group having a dithioester group, an organic group having a peroxide group, and an azo group. Examples include organic groups. From the viewpoint of ease of synthesis, ease of polymerization control, and variety of applicable polymerizable monomers, it is preferable that the functional group having the radical-generating ability of compound (1) is an organic group having a halogen atom. .
  • Examples of the organic group having a halogen atom include organic groups containing a 2-bromo-2-methylpropionyloxy group, a 2-bromo-propionyloxy group, a parachlorosulfonylbenzoyloxy group, and the like.
  • the compound (1) having a functional group capable of generating radicals at both ends of the silicone chain is preferably a compound represented by the following formula (1-1).
  • R 11 , R 12 , R 13 and R 14 are each independently an alkyl group having 1 to 18 carbon atoms or a phenyl group.
  • L 11 and L 12 are each independently a divalent organic group or a single bond.
  • n is an integer.
  • X 1 and X 2 are each independently a functional group having the ability to generate radicals.
  • R 11 , R 12 , R 13 , R 14 , L 11 , L 12 and n are R 11 , R 12 , R 13 , R 14 in the formula (1) , L 11 , L 12 and n.
  • the functional group having the ability to generate radicals of X 1 and X 2 is, for example, a functional group having a halogen atom, preferably a functional group represented by the following formula (X-1). be.
  • R HAL is a halogen atom.
  • R 16 and R 17 are each independently an alkyl group having 1 to 6 carbon atoms.
  • Q is an oxygen atom or a sulfur atom.
  • Specific examples of the compound (1) having functional groups capable of generating radicals at both ends of the silicone chain include the following compounds.
  • n is an integer.
  • Compound (1) having a functional group capable of generating radicals at both ends of a silicone chain can be produced by a known method.
  • the polymerizable monomer (2) used in the method for producing the compound of the present invention is the same as the polymerizable monomer (2) explained for the compound of the present invention, and may be used alone. You may use more than one species in combination.
  • reaction raw materials used in the production of the compound of the present invention are not limited to only the compound (1) having a functional group capable of generating radicals at both ends of the silicone chain and the polymerizable monomer (2), but can also achieve the effects of the present invention.
  • Monomers other than compound (1) and polymerizable monomer (2) may be used within a range that does not impair the properties. Examples of the other monomers include hydroxyalkyl (meth)acrylate, paravinylbenzoic acid, and N-phenylmaleimide.
  • the above-mentioned other monomers which are reaction raw materials may be used alone or in combination of two or more.
  • the charging ratio of the compound (1) having a functional group capable of generating radicals at both ends of the silicone chain and the polymerizable monomer (2) is not particularly limited, but the weight ratio (compound (1)/polymerizable monomer (2)), for example, 1/99 to 99/1, preferably 5/95 to 80/20, more preferably 10/90 to 70/30.
  • a dormant species whose active polymerization terminal is protected by an atom or an atomic group reversibly generates radicals and reacts with the monomer, so that a growth reaction progresses, and even if the first monomer is consumed, The growing ends can react with sequentially added second monomers to obtain block polymers without losing activity.
  • living radical polymerization include atom transfer radical polymerization (ATRP), reversible addition-fragmentation radical polymerization (RAFT), nitroxide-mediated radical polymerization (NMP), and organic tellurium-based radical polymerization (TERP).
  • ATRP atom transfer radical polymerization
  • RAFT reversible addition-fragmentation radical polymerization
  • NMP nitroxide-mediated radical polymerization
  • TERP organic tellurium-based radical polymerization
  • ATRP is polymerized using an organic halide or a halogenated sulfonyl compound as a polymerization initiator and a metal complex consisting of a transition metal compound and a ligand as a catalyst.
  • the compound (1) can function as a polymerization initiator, and the compound (1) can undergo living radical polymerization of the polymerizable monomer (2).
  • Transition metal compounds that can be used in ATRP are those represented by M n+ X n .
  • R 11 represents an aryl group, a linear or branched alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms)
  • R 12 represents a hydrogen atom, a halogen, and 1 to 10 carbon atoms.
  • n represents the formal charge on the metal and is an integer from 0 to 7.
  • the ligand compound capable of coordinating with the transition metal of the above-mentioned transition metal compound includes a coordination compound containing one or more nitrogen, oxygen, phosphorus, or sulfur atoms that can coordinate with the transition metal through a ⁇ bond.
  • a compound having a ligand containing two or more carbon atoms that can coordinate with a transition metal through a ⁇ bond, a compound that has a ligand that can coordinate with a transition metal through a ⁇ bond or an ⁇ bond Examples include compounds.
  • the transition metal complex is not particularly limited, but transition metal complexes of Groups 7, 8, 9, 10, and 11 are preferred, and more preferred are zero-valent copper, monovalent copper, and divalent ruthenium. , divalent iron or divalent nickel complexes.
  • divalent ruthenium complexes include dichlorotris(triphenylphosphine)ruthenium, dichlorotris(tributylphosphine)ruthenium, dichloro(cyclooctadiene)ruthenium, dichlorobenzeneruthenium, dichlorop-cymeneruthenium, dichloro(norbornadiene)ruthenium, Examples include cis-dichlorobis(2,2'-bipyridine)ruthenium, dichlorotris(1,10-phenanthroline)ruthenium, and carbonylchlorohydridotris(triphenylphosphine)ruthenium.
  • divalent 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.
  • 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, 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 Examples include.
  • Aromatic solvents such as toluene, xylene, 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 Examples include.
  • the above solvents may be used alone or in combination of two or more.
  • the polymerization temperature during the living radical polymerization is preferably in the range of room temperature to 120°C.
  • metals resulting from the transition metal compound used in the polymerization may remain in the resulting compound.
  • the metal remaining in the obtained polymer is preferably removed using activated alumina or the like after the polymerization is completed.
  • the compound of the present invention can be suitably used as a leveling agent in a coating composition, and the coating composition of the present invention contains the compound of the present invention. Since the compound 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 that has low environmental load and has low accumulation potential in the environment.
  • the content of the compound of the present invention contained in the coating composition of the present invention varies depending on the type of base resin, coating method, intended film thickness, etc., but for example, 0
  • the range is from .001 to 10 parts by weight, preferably from 0.01 to 5 parts by weight, more preferably from 0.02 to 2 parts by weight, and even more preferably from 0.02 to 1 part by weight. is within the range of
  • the compound of the present invention can exhibit a leveling effect even in a small amount, and can suppress the occurrence of problems such as foaming during coating.
  • 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 paint composition include petroleum resin paint, shellac paint, rosin paint, cellulose paint, rubber paint, lacquer paint, and cashew resin paint. , paints using natural resins such as oil-based vehicle paints; phenolic 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 , paints using synthetic resins such as fluororesin paints, etc.
  • paints using natural resins such as oil-based vehicle paints
  • phenolic 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
  • paints using synthetic resins such as fluororesin paints, etc.
  • colorants such as pigments, dyes, and carbon
  • inorganic powders such as silica, titanium oxide, zinc oxide, aluminum oxide, zirconium oxide, calcium oxide, and calcium carbonate
  • higher fatty acids such as stearic acid
  • Organic fine powder of acrylic resin, polyethylene, etc. e.g., polyethylene, etc.
  • additives such as light resistance improvers, weather resistance improvers, heat resistance improvers, antioxidants, thickeners, anti-settling agents, etc. can be added as appropriate. .
  • any known and publicly used coating method can be used, such as a slit coater, slit & spin coater, spin coater, roll coater, electrostatic coating, bar coater, Methods include gravure coater, die coater, knife coater, inkjet, dipping coating, spray coating, shower coating, screen printing, gravure printing, offset printing, and reverse coating.
  • Photosensitive resin compositions have physical properties such as resin solubility, viscosity, transparency, refractive index, conductivity, and ion permeability that change when irradiated with light such as visible light or ultraviolet light.
  • resist compositions photoresist compositions, color resist compositions for color filters, etc.
  • the resist composition is usually applied by spin coating onto a silicon wafer or a glass substrate on which various metals have been deposited to a thickness of about 1 to 2 ⁇ m. At this time, if the coating film thickness fluctuates or coating unevenness occurs, the linearity and reproducibility of the pattern deteriorates, resulting in a problem that a resist pattern having the desired precision cannot be obtained.
  • the coating composition of the present invention exhibits high leveling properties and can form a uniform coating film (cured product), the coating composition of the present invention does not have the above-mentioned problems when used as a resist composition. can be solved.
  • the photoresist composition contains an alkali-soluble resin, a radiation-sensitive substance (photosensitive substance), a solvent, etc. in addition to the compound of the present invention.
  • the alkali-soluble resin contained in the photoresist composition is a resin that is soluble in an alkaline solution that is a developer used when patterning a resist.
  • alkali-soluble resins include novolak resins obtained by condensing aromatic hydroxy compound derivatives such as phenol, cresol, xylenol, resorcinol, phloroglycinol, and hydroquinone with aldehyde compounds such as formaldehyde, acetaldehyde, and benzaldehyde; Polymers or copolymers of vinylphenol compound derivatives such as vinylphenol, m-vinylphenol, p-vinylphenol, and ⁇ -methylvinylphenol; (meth)acrylics such as acrylic acid, methacrylic acid, and hydroxyethyl (meth)acrylate.
  • Acid-based polymers or copolymers polyvinyl alcohol; modified products in which radioactive ray-sensitive groups such as quinonediazide groups, naphthoquinone azide groups, aromatic azide groups, and aromatic cinnamoyl groups are introduced through some of the hydroxyl groups of these various resins.
  • Resin examples include urethane resins containing acidic groups such as carboxylic acid and sulfonic acid in the molecule. These alkali-soluble resins may be used alone or in combination of two or more.
  • the radiation-sensitive substance contained in the photoresist composition refers to the radiation-sensitive substance that can be used to cure an alkali-soluble resin by irradiating it with energy rays such as ultraviolet rays, deep ultraviolet rays, excimer laser light, X-rays, electron beams, ion beams, molecular beams, and gamma rays.
  • energy rays such as ultraviolet rays, deep ultraviolet rays, excimer laser light, X-rays, electron beams, ion beams, molecular beams, and gamma rays.
  • energy rays such as ultraviolet rays, deep ultraviolet rays, excimer laser light, X-rays, electron beams, ion beams, molecular beams, and gamma rays.
  • a substance that changes the solubility in a developer examples include quinonediazide compounds, diazo compounds, azide compounds, onium salt compounds, halogenated organic compounds, mixtures
  • 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, and sulfonic acid chloride of quinonediazide derivatives such as 2,1-naphthoquinonediazide-5-sulf
  • diazo compound examples include salts of condensates of p-diazodiphenylamine and formaldehyde or acetaldehyde, hexafluorophosphates, tetrafluoroborates, perchlorates or periodates, and condensates of the above.
  • diazo resin inorganic salts which are reactive organisms
  • 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-based compounds examples include azidocarconic acid, diazidobenzalmethylcyclohexanones, azidocinnamylideneacetophenones, aromatic azide compounds, aromatic diazide compounds, and the like.
  • halogenated organic compound examples include halogen-containing oxadiazole compounds, halogen-containing triazine compounds, halogen-containing acetophenone compounds, halogen-containing benzophenone compounds, halogen-containing sulfoxide compounds, halogen-containing sulfone 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-dibromophenyl
  • Examples of the organic acid ester include carboxylic acid esters, sulfonic acid esters, and the like. Further, examples of the organic acid amide include carboxylic acid amide, sulfonic acid amide, and the like. Furthermore, examples of the organic acid imide include carboxylic acid imide, sulfonic acid imide, and the like.
  • the radiation-sensitive substances may be used alone 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 weight, more preferably in the range of 50 to 150 parts by weight, based on 100 parts by weight 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, and 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, propy
  • the color resist composition contains an alkali-soluble resin, a polymerizable compound, a colorant, etc. in addition to the compound of the present invention.
  • the same alkali-soluble resin contained in the above-mentioned photoresist composition can be used.
  • the polymerizable compound contained in the color resist composition is, for example, a compound having a photopolymerizable functional group that can be polymerized or crosslinked by irradiation with active energy rays such as ultraviolet rays.
  • examples of the above polymerizable compounds 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, and aromatic compounds. Esters obtained by esterification reactions between polyhydroxy compounds and unsaturated carboxylic acids, unsaturated carboxylic acids and polyhydric carboxylic acids, and polyhydric 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, a polymerizable compound having an acid group, and the like.
  • the polymerizable compounds may be used alone or in combination of two or more.
  • ester of the aliphatic polyhydroxy compound and unsaturated carboxylic acid examples include ethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, and trimethylolethane tri(meth)acrylate.
  • itaconic acid esters in which the (meth)acrylic acid portion of these acrylates is replaced with itaconic acid, crotonic acid esters in which crotonic acid is replaced, or maleic esters in which the (meth)acrylic acid portion is replaced with maleic acid.
  • ester of the aromatic polyhydroxy compound and unsaturated carboxylic acid examples include hydroquinone di(meth)acrylate, resorcin di(meth)acrylate, and pyrogallol tri(meth)acrylate.
  • the ester obtained by the esterification reaction of an unsaturated carboxylic acid, a polyhydric carboxylic acid, and a polyhydric 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 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 a (meth)acryloyl group-containing hydroxy compound include aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; fatty acids such as cyclohexane diisocyanate and isophorone diisocyanate; Cyclic diisocyanates; aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate; and (meth)acrylates such as 2-hydroxyethyl (meth)acrylate and 3-hydroxy[1,1,1-tri(meth)acryloyloxymethyl]propane. Examples include reactants with hydroxy compounds having an acryloyl group.
  • 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.
  • the aliphatic polyhydroxy compound used for preparing the polyfunctional polymerizable compound is preferably pentaerythritol or dipentaerythritol.
  • the acid value of the polyfunctional polymerizable compound is preferably in the range of 0.1 to 40, more preferably in the range of 5 to 30, since it provides good developability, curability, etc.
  • a mixture of polymerizable compounds is used. It is preferable that the acid value of is within the above range.
  • polymerizable compound having an acid group examples include a mixture containing dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and a 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 those mentioned above include (meth)acrylamides such as ethylene bis(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, the amount is in the range of 20 to 50% by mass.
  • the coloring agent of the color resist composition is not particularly limited as long as it can be colored, and for example, it may be a pigment or a dye.
  • the pigment may be either an organic pigment or an inorganic pigment.
  • the organic pigment pigments of various hues such as red pigment, green pigment, blue pigment, yellow pigment, purple pigment, orange pigment, and brown pigment can be used.
  • the chemical structure of the organic pigment includes, for example, azo type, phthalocyanine type, quinacridone type, benzimidazolone type, isoindolinone type, dioxazine type, indanthrene type, perylene type, and the like.
  • the inorganic pigment include barium sulfate, lead sulfate, titanium oxide, yellow lead, red iron oxide, and chromium oxide.
  • C.I below means a color index.
  • red pigment examples include 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, 194, 200
  • C. I. Pigment Red 48:1, 122, 168, 177, 202, 206, 207, 209, 224, 242 or 254 is preferred; I. Pigment Red 177, 209, 224 or 254 is more preferred.
  • Examples of the green pigment include 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. Among these, C. I. Pigment Green 7, 36 or 58 are preferred.
  • blue pigment examples include 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. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, or 15:6 is preferred; I. Pigment Blue 15:6 is more preferred.
  • Examples of the yellow pigment include 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,
  • Examples of the purple pigment include 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, etc.
  • C. I. Pigment Violet 19 or 23 is preferred; C.I. I. Pigment Violet 23 is more preferred.
  • orange pigment examples include 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. Pigment Orange 38 or 71 is preferred.
  • Each pixel of the three primary colors of a color filter used in a liquid crystal display device and an organic EL display device is red (R), green (G), and blue (B), so the main components are the red pigment, green pigment, and blue pigment.
  • organic pigments of colors such as yellow, purple, and orange may be used as hue adjustment.
  • the average particle diameter 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 brightness of color liquid crystal display devices and organic EL display devices. It is preferable to use the organic pigment by dispersing it so that it has 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, even more preferably 40 nm or less, and particularly preferably in the range of 10 to 30 nm.
  • the average particle diameter of the organic pigment is measured using a dynamic light scattering particle size distribution meter, such as the Nanotrac particle size distribution measuring device "UPA-EX150" manufactured by Nikkiso Co., Ltd. -EX250" etc.
  • 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, etc. Examples include black, furnace black, graphite, iron black, and titanium black. Among these, carbon black and titanium black are preferred from the viewpoint of light shielding rate and image characteristics. Alternatively, a combination of two or more organic pigments may be used to obtain black color by mixing colors.
  • carbon blacks include, for example, MA7, MA8, MA11, MA100, MA100R, MA220, MA230, MA600, #5, #10, #20, #25, #30, #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, Pri manufactured by Evonik Degussa Japan Co., Ltd.
  • resin-coated carbon black is preferred as it has the high optical density and high surface resistivity required for the black matrix of a color filter.
  • titanium blacks include, for example, titanium blacks 10S, 12S, 13R, 13M, and 13MC manufactured by Mitsubishi Materials Corporation.
  • BM black matrix
  • two or more organic pigments may be mixed to form a black color
  • a black pigment may be a mixture of three color pigments of red, green, and blue.
  • Colorants that can be mixed to prepare black pigments include Victoria Pure Blue (C.I. 42595), Auramine O (C.I. 41000), Cathylone Brilliant Flavin (Basic 13), Rhodamine 6GCP (C.I. .I.45160), Rhodamine B (C.I.45170), Safranin OK70:100 (C.I.50240), Erioglaucine X (C.I.42080), No.
  • coloring materials that can be used in combination to prepare black pigments include, for example, C.I. I. Yellow pigment 20, 24, 86, 93, 109, 110, 117, 125, 137, 138, 147, 148, 153, 154, 166, C.I. I. Orange pigment 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 pigment 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. Brown pigments 23, 25, 26, etc. can be mentioned.
  • the average primary particle size of carbon black is preferably in the range of 0.01 to 0.08 ⁇ m, and more preferably in the range of 0.02 to 0.05 ⁇ m for good developability.
  • Carbon black has a particle shape different from that of organic pigments and the like, and exists in a state called a structure in which primary particles are fused together, 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 determined by the same method as for the organic pigments, DBP absorption (JIS K6221) and specific surface area (by BET method) are generally used. JIS K6217) is preferably measured and used as an index of the structure and pore amount.
  • the absorption amount of dibutylphthalic acid (hereinafter abbreviated as "DBP") of carbon black is preferably in the range of 40 to 100 cm 3 /100g, and is in the range of 50 to 80 cm 3 /100g for good dispersibility and developability. is more preferable.
  • the specific surface area of carbon black measured by the BET method is preferably in the range of 50 to 120 m 2 /g, and more preferably in the range of 60 to 95 m 2 /g because of good dispersion stability.
  • dyes used as colorants in the color resist composition include azo dyes, anthraquinone dyes, phthalocyanine dyes, quinone imine dyes, quinoline dyes, nitro dyes, carbonyl dyes, methine dyes, etc. .
  • Examples of the azo dye include C.I. I. Acid Yellow 11, C. I. Acid Orange 7, C. I. Acid Red 37, C. I. Acid Red 180, C. I. Acid Blue 29, C. I. Direct Red 28, C. I. Direct Red 83, C. I. Direct Yellow 12, C. I. Direct Orange 26, C. I. Direct Green 28, C. I. Direct Green 59, C. I. Reactive Yellow 2, C. I. Reactive Red 17, C. I. Reactive Red 120, C. I. Reactive Black 5, C. I. Disperse Orange 5, C. I. Dispersed Red 58, C. I. Disperse Blue 165, C. I. Basic Blue 41, C. I. Basic Red 18, C. I. Mordant Red 7, C. I. Mordant Yellow 5, C. I. Examples include Mordant Black 7.
  • anthraquinone dye examples include C.I. I. Bat Blue 4, C. I. Acid Blue 40, C. I. Acid Green 25, C. I. Reactive Blue 19, C. I. Reactive Blue 49, C. I. Dispersed Red 60, C. I. Disperse Blue 56, C. I. Examples include Disperse Blue 60.
  • Examples of the phthalocyanine dye include C.I. I.
  • Examples of the quinone imine dye include C.I. I. Basic Blue 3, C. I.
  • Examples of the quinoline dye include Basic Blue 9, and examples of the quinoline dye include C.I. I. Solvent Yellow 33, C. I. Acid Yellow 3, C. I.
  • Examples of the nitro dye include Disperse Yellow 64, and examples of the nitro dye include C.I. I. Acid Yellow 1, C. I. Acid Orange 3, C. I. Examples include Disperse Yellow 42.
  • pigments as the colorant in the color resist composition, since the resulting coating film has excellent light resistance, weather resistance, and fastness.However, in order to adjust the hue, pigments may be used as necessary.
  • a dye may be used in combination.
  • the content of the colorant is preferably 1% by mass or more, more preferably 5 to 80% by mass, and more preferably 5 to 70% by mass based on the total solid content of the color resist composition. It is more preferable that the range is %.
  • the content of the colorant in the color resist composition is based on the total solids of the color resist composition. It is preferably in the range of 5 to 60% by weight, more preferably in the range of 10 to 50% by weight.
  • the content of the colorant 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; pigment intermediates or derivatives; dye intermediates or derivatives; resin-type dispersants such as polyamide resins, polyurethane resins, polyester resins, and acrylic resins.
  • graft copolymers having a nitrogen atom, acrylic block copolymers having a nitrogen atom, urethane resin dispersants, etc. are preferable.
  • these dispersants have a nitrogen atom, the nitrogen atom has an affinity for the pigment surface, and the parts other than the nitrogen atom increase the affinity for the medium, thereby improving dispersion stability.
  • These dispersants may be used alone or in combination of two or more.
  • organic solvent used in preparing the pigment dispersion examples include acetate-based solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate; propionate-based solvents such as ethoxypropionate; toluene and xylene.
  • aromatic solvents such as methoxybenzene; ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; aliphatic hydrocarbons such as hexane Solvents include nitrogen compound solvents such as N,N-dimethylformamide, ⁇ -butyrolactam and N-methyl-2-pyrrolidone; lactone solvents such as ⁇ -butyrolactone; carbamate esters and the like. These solvents may be used alone or in combination of two or more.
  • Examples of the method for preparing the pigment dispersion include a method involving a colorant kneading and dispersion step and a fine dispersion step, a method involving only a fine dispersion step, and the like.
  • the colorant, a part of the alkali-soluble resin, and, if necessary, the dispersant are mixed and kneaded.
  • the colorant can be dispersed by applying strong shearing force using a kneader.
  • Machines used for kneading include two-roll, three-roll, ball mill, thoron mill, disperser, kneader, co-kneader, homogenizer, blender, single-screw or twin-screw extruder, and the like. It is preferable to refine the particle size of the colorant by a salt milling method or the like before performing the above-mentioned kneading.
  • a solvent is added to the composition containing the colorant obtained in the kneading and dispersion step, or a colorant, an alkali-soluble resin, a solvent, and, if necessary, the dispersant is mixed.
  • the colorant particles can be dispersed to a fine state close to that of primary particles.
  • 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 using a dynamic light scattering particle size distribution analyzer, such as the Nanotrac particle size distribution analyzer "UPA-EX150” manufactured by Nikkiso Co., Ltd. -EX250" etc.
  • coating compositions photoresist compositions, and color resist compositions have been exemplified above as coating compositions, the present invention is 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 materials anti-glare
  • LR anti-reflection
  • QDD quantum dot displays
  • CF color filters
  • Color resist, inkjet ink, printing ink or paint Black resist, inkjet ink, printing ink or paint to form a black matrix, black column spacer, black photo spacer for CF such as LCD; Used for CF such as LCD. Paints for transparent protective films that protect CF surfaces; Resin compositions for LCD liquid crystal materials, column spacers, and photo spacers; Resin compositions for pixel partition walls of LCDs, PDPs, OLEDs, QDDs, etc.; positive photoresists for electrode formation.
  • protective films protective films, insulating films, plastic casings, paints for plastic casings, bezel (picture frame) inks; prism sheets that are backlight components of LCDs, light diffusion films; paints for organic insulating films of liquid crystal TFT arrays in LCDs; Internal polarizing plate surface protective coating material; PDP phosphor; OLED organic EL material, encapsulant (protective film, gas barrier); QDD quantum dot ink, encapsulant, protective film; micro (mini) LED display High refractive index lens, low refractive index sealing, LED pixel; positive photoresist used in semiconductor manufacturing, chemically amplified photoresist, antireflection film, multilayer material (SOC, SOG), underlayer film, buffer coat, developer , rinsing liquid, pattern collapse prevention agent, polymer residue removal liquid, cleaning agent and other chemicals, nanoimprint mold release agent; resin compositions for semiconductor post-processing or printed wiring boards (epoxy resin, phenolic resin, polyphenylene ether resin, liquid
  • Inkjet ink for printed matter ink for offset printing, ink for gravure printing, ink for screen printing, photoresist for printing plate manufacturing process, photosensitive material for planographic printing plate (PS plate), packaging adhesive, ballpoint pen ink; plastic film Primers for easy adhesion; Water repellents for textiles; Non-diffusing agents for grease; Cleaning liquids for cleaning the surfaces of various products or parts; Hard coat materials for optical recording media such as CDs, DVDs, and Blu-ray discs; Smartphones Or paints or hard coat materials for mobile phone casings or screens; hard coat materials for transfer films for insert molds (IMD, IMF); release films; paints or coats for various plastic molded products such as home appliance casings.
  • IMD insert molds
  • Materials Printing inks or paints for various building materials such as decorative boards; Coating materials for residential window glass; Paints for woodwork such as furniture; Coating materials for artificial/synthetic leather; Rubber roller coatings for OA equipment such as copy machines and printers
  • Materials Glass coating materials for reading parts of OA equipment such as copy machines and scanners; Optical lenses or coating materials for cameras, video cameras, glasses, contact lenses, etc.; Coating materials for windshields and glass of watches, etc.; Automobiles , Coating materials for windows of various vehicles such as railway vehicles; Paints for anti-reflection coatings for solar cell cover glasses or films; Paints or coating materials for FRP bathtubs; PCM for metal building materials or home appliances; Photo fabrication process, etc. Examples include single layer or multilayer coating compositions.
  • the compound of the present invention Since the compound of the present invention has an excellent ability to reduce surface tension, it has not only leveling properties but also wettability, permeability, detergency, water repellency, oil repellency, antifouling property, lubricity, anti-blocking property, It can also be expected to have various functions in terms of mold releasability. Furthermore, when the compound of the present invention is blended into 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 dispersant for the fine particles.
  • the compound of the present invention can be added to adhesive compositions used for adhesive tapes, etc., to improve not only leveling properties but also reduction of peeling force, suppression of peeling force fluctuations, and peeling electrification. It can also be expected to have various functions of suppressing
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) are values calculated in terms of polystyrene based on gel permeation chromatography (GPC) measurements.
  • the GPC measurement conditions are as follows.
  • Measuring device High-speed GPC device “HLC-8420GPC” manufactured by Tosoh Corporation Column: "TSK GUARDCOLUMN SuperHZ-L” manufactured by Tosoh Corporation + “TSK gel SuperHZM-N” manufactured by Tosoh Corporation + “TSK gel SuperHZM-N” manufactured by Tosoh Corporation + “TSK gel SuperHZM-N” manufactured by Tosoh Corporation + “TSK gel SuperHZM-N” manufactured by Tosoh Corporation Detector: RI (differential refractometer) Data processing: “EcoSEC Data Analysis version 1.07” manufactured by Tosoh Corporation Column temperature: 40°C Developing solvent: Tetrahydrofuran Flow rate: 0.35 mL/min Measurement sample: 7.5 mg of the sample was dissolved in 10 mL of tetrahydrofuran, and the resulting solution was filtered with a microfilter to obtain the measurement sample. Sample injection volume: 20 ⁇ L Standard sample: The
  • Example 1 Synthesis of compound (1) having living polymer blocks at both ends of silicone chain
  • a stirring device 35.10 g of n-heptane as a solvent
  • 70.0 g of a silicone compound having hydroxyl groups at both ends represented by the following formula (a-1) 35.10 g of n-heptane as a solvent and 70.0 g of a silicone compound having hydroxyl groups at both ends represented by the following formula (a-1) were added.
  • 00g and 9.81g of triethylamine as a catalyst were charged, and the temperature inside the flask was raised to 40°C.
  • n 1 is 65 on average.
  • Mn molecular weight of the silicone chain
  • a flask purged with nitrogen was charged with 3.10 g of polypropylene glycol monomethacrylate (average repeating number of propylene glycol: 4 to 6) and 10.00 g of methyl ethyl ketone as a solvent, and the temperature was raised to 60° C. with stirring under a nitrogen stream.
  • 0.67 g of 2,2'-bipyridyl and 0.19 g of cuprous chloride were added as catalysts, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 60°C.
  • 5.00 g of the compound represented by the above formula (A-1) was added as a polymerization initiator, and living polymerization was performed at 60° C. for 27 hours under a nitrogen stream.
  • the molecular weight of the obtained compound (1) was measured by GPC, and the weight average molecular weight (Mw) was 12,100, the number average molecular weight (Mn) was 8,400, and (Mw/Mn) was 1.4. . Moreover, the ratio of silicone chains in compound (1) was 57% by mass.
  • Example 2 Synthesis of compound (2) having living polymer blocks at both ends of silicone chain
  • a flask purged with nitrogen was charged with 9.00 g of polypropylene glycol monomethacrylate (average repeating number of propylene glycol: 4 to 6) and 14.35 g of methyl ethyl ketone as a solvent, and the temperature was raised to 60° C. with stirring under a nitrogen stream.
  • 0.67 g of 2,2'-bipyridyl and 0.19 g of cuprous chloride were added as catalysts, and the mixture was stirred for 30 minutes while maintaining the inside of the flask at 60°C.
  • the molecular weight of the obtained compound (2) was measured by GPC, and the weight average molecular weight (Mw) was 16,300, the number average molecular weight (Mn) was 11,200, and (Mw/Mn) was 1.5. . Moreover, the ratio of silicone chains in compound (2) was 33% by mass.
  • Example 3 Synthesis of compound (3) having living polymer blocks at both ends of silicone chain
  • a stirring device 100.00 g
  • a thermometer 100.00 g
  • 200.0 g of a silicone compound having hydroxyl groups at both ends represented by the following formula (a-2) 100.00 g
  • a silicone compound having hydroxyl groups at both ends represented by the following formula (a-2) 100.00 g
  • a silicone compound having hydroxyl groups at both ends represented by the following formula (a-2) were added.
  • 00g and 12.45g of triethylamine as a catalyst were charged, and the temperature inside the flask was raised to 40°C.
  • n 2 is 130 on average.
  • Mn molecular weight of the silicone chain
  • the molecular weight of the obtained compound (3) was measured by GPC, and the weight average molecular weight (Mw) was 27,600, the number average molecular weight (Mn) was 19,500, and (Mw/Mn) was 1.4. . Moreover, the ratio of silicone chains in compound (3) was 32% by mass.
  • n 3 is 65 on average.
  • Mn molecular weight of the silicone chain
  • the weight average molecular weight (Mw) was 6,500
  • the number average molecular weight (Mn) was 1,900
  • (Mw/Mn) was 3. It was 4.
  • the ratio of silicone chains in compound (1') was 30% by mass.
  • the weight average molecular weight (Mw) was 7000
  • the number average molecular weight (Mn) was 2,000
  • (Mw/Mn) was 3.5. Met.
  • the ratio of silicone chains in compound (2') was 30% by mass.
  • 3 ml of the obtained resist composition was dropped onto the center of a 10 cm x 10 cm chromium-plated glass substrate, and spin coating was performed at a rotation speed of 400 rpm and a rotation time of 20 seconds to obtain a coated substrate.
  • SUS pins were placed on the four corners of a hot plate, and the obtained coating base material was placed on the support pins and dried by heating at 100° C. for 100 seconds to produce a laminate having a coating layer.
  • Pin unevenness evaluation The portion of the laminate produced above where the support pin and the coated substrate came into contact was visually observed, and the pin unevenness of the coating layer was evaluated according to the following criteria.
  • “Pin unevenness” refers to film thickness unevenness (drying unevenness) that occurs mainly in the area where the support pin and the coating base material contact, and is similar to ripples that spread around the area where the support pin and the coating base material contact. Confirmed by shape. 1: Hardly any pin unevenness is observed 2: Pin unevenness is observed

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PCT/JP2023/003306 2022-03-08 2023-02-02 化合物、当該化合物の製造方法、レベリング剤、コーティング組成物、レジスト組成物及び物品 Ceased WO2023171186A1 (ja)

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EP23766366.1A EP4491648A4 (en) 2022-03-08 2023-02-02 COMPOUND, PROCESS FOR PRODUCING SAID COMPOUND, LEVELING AGENT, COATING COMPOSITION, PHOTORESIST COMPOSITION, AND ARTICLE
CN202380023020.8A CN118742582A (zh) 2022-03-08 2023-02-02 化合物、该化合物的制造方法、流平剂、涂覆组合物、抗蚀剂组合物及物品
US18/842,203 US20250188226A1 (en) 2022-03-08 2023-02-02 Compound, method for producing the compound, leveling agent, coating composition, resist composition, and article
JP2024505948A JP7563651B2 (ja) 2022-03-08 2023-02-02 化合物、当該化合物の製造方法、レベリング剤、コーティング組成物、レジスト組成物及び物品
KR1020247022724A KR20240157636A (ko) 2022-03-08 2023-02-02 화합물, 당해 화합물의 제조 방법, 레벨링제, 코팅 조성물, 레지스트 조성물 및 물품

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Citations (7)

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Publication number Priority date Publication date Assignee Title
US3300309A (en) 1963-09-06 1967-01-24 Polychrome Corp Moisture-resistant planographic plates and methods of producing same
JPH0397735A (ja) * 1989-08-14 1991-04-23 Minnesota Mining & Mfg Co <3M> シロキサンイニファーター化合物
JP2000514479A (ja) * 1996-07-10 2000-10-31 カーネギー メロン ユニヴァーシティー 原子転移ラジカル重合を用いる新規のホモ―及びコポリマーの調製
JP2002179991A (ja) 2000-09-29 2002-06-26 Byk Chem Gmbh 表面コーティング用レベリング剤
CN101983976A (zh) * 2010-12-10 2011-03-09 华东理工大学 一种氟硅嵌段共聚物的制备方法
CN105713157A (zh) * 2016-02-29 2016-06-29 南京林业大学 一种具有pH响应的两亲性有机硅嵌段共聚物及制备方法
JP2018199765A (ja) 2017-05-26 2018-12-20 楠本化成株式会社 両親媒性ブロック共重合体を利用した塗料用レベリング剤

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300309A (en) 1963-09-06 1967-01-24 Polychrome Corp Moisture-resistant planographic plates and methods of producing same
JPH0397735A (ja) * 1989-08-14 1991-04-23 Minnesota Mining & Mfg Co <3M> シロキサンイニファーター化合物
JP2000514479A (ja) * 1996-07-10 2000-10-31 カーネギー メロン ユニヴァーシティー 原子転移ラジカル重合を用いる新規のホモ―及びコポリマーの調製
JP2002179991A (ja) 2000-09-29 2002-06-26 Byk Chem Gmbh 表面コーティング用レベリング剤
CN101983976A (zh) * 2010-12-10 2011-03-09 华东理工大学 一种氟硅嵌段共聚物的制备方法
CN105713157A (zh) * 2016-02-29 2016-06-29 南京林业大学 一种具有pH响应的两亲性有机硅嵌段共聚物及制备方法
JP2018199765A (ja) 2017-05-26 2018-12-20 楠本化成株式会社 両親媒性ブロック共重合体を利用した塗料用レベリング剤

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Title
See also references of EP4491648A4

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EP4491648A4 (en) 2025-07-02
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