WO2020044918A1 - Composition de résine photosensible négative - Google Patents

Composition de résine photosensible négative Download PDF

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Publication number
WO2020044918A1
WO2020044918A1 PCT/JP2019/029854 JP2019029854W WO2020044918A1 WO 2020044918 A1 WO2020044918 A1 WO 2020044918A1 JP 2019029854 W JP2019029854 W JP 2019029854W WO 2020044918 A1 WO2020044918 A1 WO 2020044918A1
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WIPO (PCT)
Prior art keywords
group
photosensitive resin
resin composition
component
negative photosensitive
Prior art date
Application number
PCT/JP2019/029854
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English (en)
Japanese (ja)
Inventor
朋哉 鈴木
安達　勲
Original Assignee
日産化学株式会社
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Application filed by 日産化学株式会社 filed Critical 日産化学株式会社
Priority to KR1020217005961A priority Critical patent/KR20210052452A/ko
Priority to JP2020540172A priority patent/JP7464911B2/ja
Priority to CN201980056292.1A priority patent/CN112639618A/zh
Publication of WO2020044918A1 publication Critical patent/WO2020044918A1/fr
Priority to JP2024043870A priority patent/JP2024073626A/ja

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    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
    • 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
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • 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
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • 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
    • 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
    • C08F222/36—Amides or imides
    • C08F222/40—Imides, e.g. cyclic imides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor

Definitions

  • the present invention relates to a negative photosensitive resin composition containing an alkali-soluble polymer, at least two kinds of crosslinkable compounds, at least one kind of photopolymerization initiator, and a solvent.
  • a negative photosensitive resin composition for forming a microlens containing an alkali-soluble polymer, at least two kinds of crosslinkable compounds, at least one kind of photopolymerization initiator, and a solvent.
  • it relates to a negative photosensitive resin composition for forming a microlens.
  • CMOS image sensors have been provided with microlenses in order to improve light collection efficiency.
  • an etch-back method is known (Patent Documents 1 and 2). That is, a resist pattern is formed on the microlens resin layer formed on the color filter, and the resist pattern is reflowed by heat treatment to form a lens pattern. Using the lens pattern formed by reflowing the resist pattern as an etching mask, the lower microlens resin layer is etched back, and the lens pattern shape is transferred to the microlens resin layer to produce a microlens.
  • Such microlenses are required to have various properties such as chemical resistance and high transparency.
  • a film is formed in a pattern only at an arbitrary position on an electronic device element such as a CCD / CMOS image sensor, a liquid crystal display, and an organic EL display, photolithography is required.
  • a photosensitive material is required to be able to form a pattern with a low exposure amount (sensitivity characteristics) and to suppress generation of a residue after alkali development.
  • Patent Document 3 a microlens-forming photosensitive resin composition containing a maleimide-based copolymer
  • Patent Document 4 a positive resist composition containing a triazine skeleton
  • these patent documents require high-temperature heating of more than 100 ° C., for example, 140 ° C. to 260 ° C., in order to satisfy the above-mentioned various properties, particularly solvent resistance. Not satisfying.
  • the present invention has been made based on the above circumstances, and the problem to be solved is that a film obtained at a baking temperature of 100 ° C. has high transparency, solvent resistance, sensitivity characteristics, and unexposed portions.
  • the purpose of the present invention is to provide a negative photosensitive resin composition which can significantly improve the residue of the above.
  • the present invention relates to the following component (A), 80% to 90% by mass based on 100% by mass of component (A), and 3% by mass based on 100% by mass of component (B). % Of the following (C) component and a solvent.
  • C) at least one photopolymerization initiator
  • the at least two kinds of crosslinkable compounds include, for example, a crosslinkable compound having two acryloyloxy groups or methacryloyloxy groups in one molecule as the polymerizable group, and an acryloyloxy group or methacryloyloxy group as the polymerizable group. It contains a crosslinkable compound having three or more in one molecule.
  • the alkali-soluble polymer has, for example, a structural unit selected from the group consisting of the formulas (1a), (1b), (1c), (1d), and (1e).
  • R 1 represents a hydrogen atom or a methyl group
  • A represents an —O— group or a —NH— group
  • X represents a single bond, an alkylene group having 1 to 3 carbon atoms, or 1 to 3 carbon atoms.
  • the divalent linking group represents, for example, the alkyleneoxy group having 1 to 3 carbon atoms or a group in which two or more alkyleneoxy groups having 1 to 3 carbon atoms are bonded.
  • the alkali-soluble polymer is, for example, a copolymer further having a structural unit selected from the group consisting of the following formulas (2a), (2b) and (2c) different from the structural units.
  • R 1 represents a hydrogen atom or a methyl group
  • A represents an —O— group or a —NH— group
  • X represents a single bond
  • Z 4 represents a divalent linking group containing an alkyleneoxy group
  • Z 4 represents a linear organic group having 1 to 3 carbon atoms, or a branched or cyclic organic group having 3 to 14 carbon atoms. .
  • the divalent linking group represents, for example, the alkyleneoxy group having 1 to 3 carbon atoms or a group in which two or more alkyleneoxy groups having 1 to 3 carbon atoms are bonded.
  • the organic group may have at least one hetero atom such as a nitrogen atom and an oxygen atom, and may have a double bond or a triple bond between two carbon atoms or between a carbon atom and a hetero atom. Is also good.
  • the cyclic organic group include an aromatic hydrocarbon group, an alicyclic hydrocarbon group, a bridged hydrocarbon group, and a heterocyclic group.
  • the negative photosensitive resin composition of the present invention is, for example, for forming microlenses.
  • the present invention also includes a step of applying the negative-type photosensitive resin composition on a substrate and prebaking to form a resin film, a step of exposing the resin film through a mask, and a step of applying the exposed resin film to an alkaline developer. And a step of exposing the entire surface of the resin film after the development.
  • the method may further include a step of post-baking the resin film after or before the step of exposing the entire surface of the resin film after the development.
  • the negative photosensitive resin composition of the present invention can be prepared by optimizing the addition amount of an alkali-soluble polymer, at least two types of crosslinkable compounds, and at least one type of photopolymerization initiator, so that A film obtained at a baking temperature of ° C. is highly transparent, has high sensitivity, has little residue in unexposed areas, and has excellent solvent resistance. Therefore, the negative photosensitive resin composition of the present invention is suitable as a material for forming a microlens.
  • the present invention relates to the component (A), 80% to 90% by mass based on 100% by mass of the component (A), and 3% to 20% by mass based on 100% by mass of the total amount of the component (B) % Of the component (C) and a solvent.
  • the solid content of the negative photosensitive resin composition of the present invention excluding the solvent is usually 1% by mass to 50% by mass.
  • the components of the negative photosensitive resin composition of the present invention excluding the solvent are defined as solids.
  • the component (A) in the negative photosensitive resin composition of the present invention is an alkali-soluble polymer.
  • the polymer is a polymer of a raw material monomer containing a monomer having an alkali-soluble group and optionally another monomer.
  • the alkali-soluble polymer of the component (A) may have an alkali-soluble group, and there is no particular limitation on the skeleton of the main chain and the type of side chain of the polymer constituting the polymer.
  • the weight average molecular weight of the alkali-soluble polymer is, for example, from 1,000 to 50,000, preferably from 3,000 to 40,000.
  • the weight average molecular weight is a value obtained by gel permeation chromatography (GPC) using polystyrene as a standard sample.
  • Examples of the monomer having an alkali-soluble group include a monomer having a carboxyl group, a monomer having a phenolic hydroxy group, a monomer having an acid anhydride group, and a monomer having a maleimide group.
  • Examples of the monomer having a carboxyl group include acrylic acid, methacrylic acid, crotonic acid, mono- (2- (acryloyloxy) ethyl) phthalate, mono- (2- (methacryloyloxy) ethyl) phthalate, N- (carboxy) Phenyl) maleimide, N- (carboxyphenyl) methacrylamide, N- (carboxyphenyl) acrylamide, 4-vinylbenzoic acid.
  • Examples of the monomer having a phenolic hydroxy group include hydroxystyrene, N- (hydroxyphenyl) acrylamide, N- (hydroxyphenyl) methacrylamide, and N- (hydroxyphenyl) maleimide.
  • Examples of the monomer having an acid anhydride group include maleic anhydride and itaconic anhydride.
  • Examples of the monomer having a maleimide group include the aforementioned N- (carboxyphenyl) maleimide, N- (hydroxyphenyl) maleimide, and maleimide.
  • a polymer of a monomer containing at least one selected from the group consisting of acrylic acid, methacrylic acid, maleic anhydride, and maleimide is preferable.
  • the alkali-soluble polymer of the component (A) may be a copolymer of the monomer having an alkali-soluble group and another monomer.
  • the copolymer is not limited to a copolymer obtained from two kinds of monomers, and may be a terpolymer (ternary copolymer) obtained from three kinds of monomers.
  • Specific examples of the other monomer include an acrylate compound, a methacrylate compound, an N-substituted maleimide compound, an acrylonitrile compound, an acrylamide compound, a methacrylamide compound, a styrene compound, and a vinyl compound.
  • specific examples of the other monomer will be described, but the invention is not limited thereto.
  • the acrylate compound examples include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, phenoxyethyl acrylate, 2,2,2-trifluoroethyl Acrylate, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate, 2-methyl-2- Adamantyl acrylate, 2-propyl-2-adamantyl acrylate, 8-methyl-8 Tricyclodecyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybuty
  • methacrylate compound examples include, for example, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate, phenyl methacrylate, phenoxyethyl methacrylate, 2,2,2-trifluoroethyl Methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, 2-methoxyethyl methacrylate, methoxytriethylene glycol methacrylate, 2-ethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methoxybutyl methacrylate, 2-methyl-2-methyl Adamantyl methacrylate, ⁇ -butyrolactone Tacrylate, 2-propyl-2-adamantyl methacrylate,
  • vinyl compound examples include methyl vinyl ether, benzyl vinyl ether, vinyl naphthalene, vinyl anthracene, vinyl biphenyl, vinyl carbazole, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, and propyl vinyl ether.
  • styrene compound examples include styrene, methylstyrene, chlorostyrene, and bromostyrene.
  • N-substituted maleimide compound examples include N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.
  • acrylonitrile compound examples include acrylonitrile.
  • the method for obtaining the alkali-soluble polymer of the component (A) is not particularly limited, but generally, a raw material monomer containing the above-mentioned monomer having an alkali-soluble group is polymerized in a polymerization solvent at a temperature of usually 50 ° C to 110 ° C. It is obtained by reacting.
  • the alkali-soluble polymer obtained by the above method has a structural unit selected from the group consisting of the formulas (1a), (1b), (1c), (1d) and (1e).
  • the alkali-soluble polymer may further have a structural unit different from the structural unit and selected from the group consisting of the formulas (2a), (2b) and (2c).
  • the content of the component (A) in the negative photosensitive resin composition of the present invention is usually 48% by mass to 55% by mass based on the content in the solid content of the composition.
  • the component (B) in the negative photosensitive resin composition of the present invention comprises at least two polymerizable groups selected from the group consisting of an acryloyloxy group, a methacryloyloxy group, an allyl group and a vinyl group.
  • Species of crosslinkable compounds As the component (B), a combination of a crosslinkable compound having two polymerizable groups in one molecule and a crosslinkable compound having three or more polymerizable groups in one molecule is preferable.
  • the polymerizable group exists at a molecular terminal of the crosslinkable compound.
  • the crosslinkable compound of the component (B) has a weight average molecular weight of 200 to 200 from the viewpoint that the compatibility with other components of the negative photosensitive resin composition of the present invention is good and the developability is not affected. 1,000 compounds are preferred.
  • crosslinking compound examples include, for example, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, pentaerythritol triacrylate, pentaerythritol Trimethacrylate, pentaerythritol diacrylate, pentaerythritol dimethacrylate, tetramethylolpropanetetraacrylate, tetramethylolpropanetetramethacrylate, tetramethylolmethanetetraacrylate, tetramethylolmethanetetramethacrylate, trimethylolpropanetriacrylate, trimethylolpropanetriacrylate,
  • the crosslinkable compound can be easily obtained as a commercial product, for example, KAYARAD (registered trademark) T-1420, DPHA, DPHA-2C, D-310, D-330, DPCA-20.
  • BP-10EA HPP-A, G-201P, TMP-A, TMP-3EO-A, TMP-6EO-3A, PE-3A, PE-4A, DPE-6A Epoxy ester 40EM, 70PA, 200PA, 80MFA, 3002M, 3002A, 3000MK, 3000A, EX-0205, AH-600, AT-600, UA-306H, UA-306T, UA-306I UA-510H, UF-8001G, DAUA-167 (manufactured by Kyoeisha Chemical Co., Ltd.); EBECRYL (registered trademark) TPGDA, 145, 150, PEG400DA, 11, HPNDA, PETIA, PETIA, PETRA, TMPTA, TMPEOTA, OTA480, DPHA, 180, 40, 140, 204, 205, 210, 215, 220, 6202, 230, 244, 245, 264, 265, 270, 280 / 15IB, 284,
  • the crosslinkable compound (B) is used in combination of two or more.
  • a crosslinkable compound having two polymerizable groups in one molecule and a crosslinkable compound having three or more polymerizable groups in one molecule are preferable.
  • the crosslinkable compound having three or more polymerizable groups in one molecule may be a combination of two or more crosslinkable compounds having different numbers of polymerizable groups.
  • an acryloyloxy group or a methacryloyloxy group is preferable.
  • the content of the component (B) in the negative photosensitive resin composition of the present invention is from 80% by mass to 90% by mass relative to 100% by mass of the component (A).
  • the component (C) in the negative photosensitive resin composition of the present invention is at least one kind of photopolymerization initiator.
  • the photopolymerization initiator of the component (C) is not particularly limited as long as it has absorption in a light source used at the time of photocuring.
  • photopolymerization initiator examples include tert-butylperoxy-iso-butyrate, 2,5-dimethyl-2,5-bis (benzoyldioxy) hexane, and 1,4-bis [ ⁇ - (tert-butyldioxy) -Iso-propoxy] benzene, di-tert-butyl peroxide, 2,5-dimethyl-2,5-bis (tert-butyldioxy) hexene hydroperoxide, ⁇ - (iso-propylphenyl) -iso-propyl hydroperoxide, tert -Butyl hydroperoxide, 1,1-bis (tert-butyldioxy) -3,3,5-trimethylcyclohexane, butyl-4,4-bis (tert-butyldioxy) valerate, cyclohexanone peroxide, 2,2 ′, 5,5 '-Tetra (tert-butyl
  • the photopolymerization initiator can be obtained as a commercial product, for example, OMNIRAD (registered trademark) 651, 184, 500, 2959, 127, 754, 907, 369, 379, 379EG, 819, 819DW, 1700, 1870, 784, 1173, MBF, 4265, TPO (all manufactured by IGM Resins) [former IRGACURE (registered trademark) 651, 184, 500] , 2959, 127, 754, 907, 369, 379, 379EG, 819, 819DW, 1700, 1870, 784, 1173, MBF, 4265, TPO , BASF Japan Ltd.)], IRGACURE (registered trademark) 1800, OXE01, OXE02 (all above) BASF Japan Co., Ltd.), KAYACURE (registered trademark) DETX, MBP, DMBI, EPA, OA (all manufactured by Nippon Kayaku Co., Ltd.), VICURE-10,
  • the photopolymerization initiator of the component (C) can be used alone or in combination of two or more.
  • the content of the component (C) in the negative photosensitive resin composition of the present invention is 3% by mass to 20% by mass based on 100% by mass of the total amount of the component (B).
  • the negative photosensitive resin composition of the present invention contains a solvent.
  • the solvent is not particularly limited as long as it dissolves the components (A), (B) and (C).
  • solvent examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and propylene.
  • propylene glycol monomethyl ether propylene glycol monomethyl ether acetate, 2-heptanone, ethyl lactate, butyl lactate, and cyclohexanone are preferred from the viewpoint of improving the leveling property of the coating film.
  • the solvents can be used alone or in combination of two or more.
  • the negative photosensitive resin composition of the present invention may also contain a surfactant for the purpose of improving coatability.
  • a surfactant for example, polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene Polyoxyethylene alkyl aryl ethers such as ethylene nonyl phenyl ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Sorbitan fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as bitane
  • the surfactants can be used alone or in combination of two or more.
  • its content in the negative photosensitive resin composition of the present invention is 3% by mass or less, for example, 0.1% by mass based on the content in the solid content of the composition. It is from 0001% by mass to 3% by mass, preferably from 0.001% by mass to 1% by mass, more preferably from 0.01% by mass to 0.5% by mass.
  • the negative photosensitive resin composition of the present invention is, as long as the effects of the present invention are not impaired, as necessary, a curing aid, an ultraviolet absorber, a sensitizer, a plasticizer, an antioxidant, an adhesion aid, Alternatively, a dissolution promoter such as a polyhydric phenol or a polycarboxylic acid can be included as another additive.
  • the method for preparing the negative photosensitive resin composition of the present invention is not particularly limited.
  • the alkali-soluble polymer of the component (A) is dissolved in the solvent, and the resulting solution is mixed with the crosslinkable component of the component (B).
  • the compound and the photopolymerization initiator of the component (C) are mixed at a predetermined ratio to form a uniform solution.
  • the above-mentioned other additives are further added and mixed if necessary.
  • Substrate a semiconductor substrate such as silicon covered with a silicon oxide film, a semiconductor substrate such as silicon covered with a silicon nitride film or a silicon oxynitride film, a silicon nitride substrate, a quartz substrate, a glass substrate (alkali-free glass, low
  • a suitable coating method such as a spinner or a coater.
  • a coating film is formed by pre-baking using a heating means such as a hot plate.
  • the pre-bake conditions are appropriately selected from a bake temperature of 80 ° C. to 150 ° C. and a bake time of 0.3 to 60 minutes, preferably a bake temperature of 80 ° C. to 100 ° C. and a bake time of 0.5 to 5 minutes. It is.
  • the thickness of the film formed from the negative photosensitive resin composition of the present invention is, for example, 0.005 ⁇ m to 20 ⁇ m, and preferably 0.01 ⁇ m to 15 ⁇ m.
  • a mask for forming a predetermined pattern on the obtained film.
  • a mask for example, a g-line, an i-line, and a KrF excimer laser can be used.
  • post-exposure heating (Post @ Exposure @ Bake) is performed as necessary. Conditions for the post-exposure baking are appropriately selected from a heating temperature of 80 ° C. to 100 ° C. and a heating time of 0.3 to 60 minutes. Then, development is performed with an alkaline developer.
  • alkaline developer examples include an aqueous solution of an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, an aqueous solution of a quaternary ammonium hydroxide such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline, and ethanolamine. And aqueous alkaline solutions such as aqueous amine solutions such as propylamine and ethylenediamine. Further, a surfactant can be added to these developers.
  • an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide
  • a quaternary ammonium hydroxide such as tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline
  • ethanolamine aqueous alkaline solutions
  • aqueous amine solutions such as propylamine and ethylenediamine.
  • a surfactant can be added to these developers.
  • the development conditions are appropriately selected from a development temperature of 5 ° C. to 50 ° C. and a development time of 10 seconds to 300 seconds.
  • the film formed from the negative photosensitive resin composition of the present invention can be easily developed at room temperature using an aqueous solution of tetramethylammonium hydroxide.
  • rinsing is appropriately performed using, for example, ultrapure water as a rinsing liquid.
  • the developed film is entirely exposed using, for example, a g-line, an i-line, or a KrF excimer laser. Further, before or after the entire surface exposure, post-baking may be performed on the developed film by using a heating means such as a hot plate.
  • the post-baking conditions are appropriately selected from, for example, a baking temperature of 80 to 100 ° C. and a baking time of 0.5 to 60 minutes.
  • Example 1 19.7 g of a solution (solid content concentration: 35% by mass) of the alkali-soluble polymer as the component (A) obtained in Synthesis Example 1, and PET-30 (Nippon Kayaku Co., Ltd.) as a crosslinkable compound as the component (B) 3.4 g) and 2.1 g of ABE-300 (manufactured by Shin-Nakamura Chemical Co., Ltd.), IRGACURE (registered trademark) OXE01 (manufactured by BASF Japan Co., Ltd.) as a photopolymerization initiator as a component (C).
  • ABE-300 manufactured by Shin-Nakamura Chemical Co., Ltd.
  • IRGACURE registered trademark
  • OXE01 manufactured by BASF Japan Co., Ltd.
  • OMNIRAD registered trademark
  • 184 manufactured by IGM Resins
  • DFX-18 manufactured by Neos
  • a surfactant 0.0040 g was dissolved in 5.6 g of propylene glycol monomethyl ether and 18.4 g of propylene glycol monomethyl ether acetate. The solution was used. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore size of 1 ⁇ m to prepare a negative photosensitive resin composition.
  • Example 2 19.6 g of a solution (solid content concentration: 35% by mass) of the alkali-soluble polymer (A) obtained in Synthesis Example 1, and PET-30 (Nippon Kayaku Co., Ltd.) as a crosslinkable compound as the component (B) 4.1 g) and 2.1 g of ABE-300 (manufactured by Shin-Nakamura Chemical Co., Ltd.), IRGACURE (registered trademark) OXE01 (manufactured by BASF Japan Ltd.) as a photopolymerization initiator as a component (C).
  • ABE-300 manufactured by Shin-Nakamura Chemical Co., Ltd.
  • IRGACURE registered trademark
  • OXE01 manufactured by BASF Japan Ltd.
  • Example 3 18.8 g of a solution (solid content concentration: 35% by mass) of the alkali-soluble polymer as the component (A) obtained in Synthesis Example 1, and PET-30 (Nippon Kayaku Co., Ltd.) as a crosslinkable compound as the component (B) 3.9 g of ABE-300 (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) and 2.0 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF Japan) as a photopolymerization initiator as the component (C).
  • ABE-300 manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • IRGACURE registered trademark
  • OXE01 manufactured by BASF Japan
  • OMNIRAD registered trademark
  • 184 manufactured by IGM Resins
  • DFX-18 manufactured by Neos Corporation
  • a surfactant 0.0040 g was dissolved in 6.2 g of propylene glycol monomethyl ether and 18.4 g of propylene glycol monomethyl ether acetate. The solution was used. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore size of 1 ⁇ m to prepare a negative photosensitive resin composition.
  • Example 4 23.7 g of a solution (solid content concentration: 35% by mass) of the alkali-soluble polymer as the component (A) obtained in Synthesis Example 2, and PET-30 (Nippon Kayaku Co., Ltd.) as a crosslinkable compound as the component (B) 5.0 g of ABE-300 (manufactured by Shin-Nakamura Chemical Co., Ltd.) and IRGACURE (registered trademark) OXE01 (manufactured by BASF Japan Ltd.) as a photopolymerization initiator as a component (C).
  • ABE-300 manufactured by Shin-Nakamura Chemical Co., Ltd.
  • IRGACURE registered trademark
  • OXE01 manufactured by BASF Japan Ltd.
  • OMNIRAD registered trademark
  • 184 manufactured by IGM Resins
  • DFX-18 manufactured by Neos Corporation
  • a surfactant 0.0050 g was dissolved in 1.2 g of propylene glycol monomethyl ether and 16.6 g of propylene glycol monomethyl ether acetate. The solution was used. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore size of 1 ⁇ m to prepare a negative photosensitive resin composition.
  • OMNIRAD registered trademark
  • 184 manufactured by IGM Resins
  • DFX-18 manufactured by Neos
  • a surfactant 0.0040 g was dissolved in 4.9 g of propylene glycol monomethyl ether and 18.4 g of propylene glycol monomethyl ether acetate. The solution was used. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore size of 1 ⁇ m to prepare a negative photosensitive resin composition.
  • the content of the component (B) is out of the range of the present invention.
  • Comparative Example 2 15.6 g of a solution (solid content concentration: 35% by mass) of the alkali-soluble polymer as the component (A) obtained in Synthesis Example 1, and PET-30 (Nippon Kayaku Co., Ltd.) as a crosslinkable compound as the component (B) 3.3 g of ABE-300 (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) and 3.3 g of IRGACURE (registered trademark) OXE01 (manufactured by BASF Japan) as a photopolymerization initiator as a component (C).
  • ABE-300 manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • IRGACURE registered trademark
  • OXE01 manufactured by BASF Japan
  • 0.0039 g was dissolved in 2.6 g of propylene glycol monomethyl ether and 18.5 g of propylene glycol monomethyl ether acetate to form a solution. Thereafter, the mixture was filtered using a polyethylene microfilter having a pore size of 1 ⁇ m to prepare a negative photosensitive resin composition.
  • the content of the component (B) is out of the range of the present invention, and the component (B) is a crosslinkable compound having two polymerizable groups in one molecule. Not included.
  • the mixture was filtered using a polyethylene microfilter having a pore size of 1 ⁇ m to prepare a negative photosensitive resin composition.
  • the content of the component (B) is out of the range of the present invention, and the component (B) is a crosslinkable compound having two polymerizable groups in one molecule. Not included.
  • the mixture was filtered using a polyethylene microfilter having a pore size of 1 ⁇ m to prepare a negative photosensitive resin composition.
  • the content of the component (B) is out of the range of the present invention, and the component (B) is a crosslinkable compound having two polymerizable groups in one molecule. Not included.
  • the entire surface of the resin film was irradiated with ultraviolet rays having an exposure amount of 1000 mJ / cm 2 at 365 nm by a batch type UV irradiation device (high-pressure mercury lamp 2 kW ⁇ 1 lamp) (manufactured by Eye Graphics Co., Ltd.).
  • a cured film was formed on a quartz substrate. Both the pre-bake and post-bake were performed in the air.
  • the transmittance of these cured films was measured using an ultraviolet-visible spectrophotometer UV-2550 (manufactured by Shimadzu Corporation) while changing the wavelength in steps of 2 nm in a wavelength range of 400 nm to 800 nm. Table 2 shows the values of the minimum transmittance measured in the wavelength range of 400 nm to 800 nm. A value closer to 100% indicates that a transparent film was obtained.
  • the resin film was developed for 60 seconds using an aqueous solution of tetramethylammonium hydroxide (TMAH) having a concentration shown in Table 1 as an alkaline developer, rinsed with ultrapure water for 20 seconds, and dried.
  • TMAH tetramethylammonium hydroxide
  • the resin film formed from the negative photosensitive resin compositions prepared in Comparative Examples 3 and 5 was removed from the silicon wafer. Further, the remaining resin film was post-baked on a hot plate at 100 ° C. for 5 minutes.
  • the entire surface of the resin film is irradiated with ultraviolet light having an exposure amount of 1000 mJ / cm 2 at 365 nm by a batch type UV irradiation device (high-pressure mercury lamp 2 kW ⁇ 1 lamp) (manufactured by Eye Graphics Co., Ltd.)
  • a cured film was formed on the silicon wafer. Both the pre-bake and post-bake were performed in the air.
  • TMAH tetramethylammonium hydroxide
  • TMAH tetramethylammonium hydroxide
  • the rectangular pattern was not formed from the resin films formed from the negative photosensitive resin compositions prepared in Comparative Examples 3 and 5.
  • the thickness of the formed product on the silicon wafer was measured by the same method as that for measuring the thickness of the resin film.
  • the residual film ratio (%) was evaluated by comparing with the film thickness of the resin film immediately after prebaking. Table 2 shows the results.
  • the residual film ratio is calculated from the formula (film thickness after development / film thickness after pre-baking) ⁇ 100, and the closer the value is to 100%, the less the exposed portion of the resin film is likely to be dissolved in the developing solution. .
  • the film thickness of the unexposed portion of the resin film was measured using a light interference type film thickness measuring device Lambda Ace VM-2110 (manufactured by SCREEN Semiconductor Solutions Co., Ltd.). The smaller the film thickness, the smaller the residue.
  • the residue was evaluated as “x” when the film thickness was 10 nm or more, “ ⁇ ” when it was less than 10 nm and 5 nm or more, and “ ⁇ ” when it was less than 5 nm. Table 2 shows the evaluation results.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Materials For Photolithography (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerisation Methods In General (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)

Abstract

Le problème décrit par l'invention est de concevoir une nouvelle composition de résine photosensible négative. Selon l'invention, la solution porte sur une composition de résine photosensible négative comprenant un composant (A), un composant (B) dans une proportion de 80 à 90 % en masse par rapport à 100 % en masse du composant (A), un composant (C) en une proportion de 3 à 20 % en masse par rapport à 100 % en masse, c'est-à-dire la quantité totale, du composant (B), et un solvant ; (A) : un polymère soluble dans les alcalis ; (B) : au moins deux composés réticulables ayant chacun, par molécule, au moins deux groupes polymérisables choisis dans le groupe constitué par un groupe acryloyloxy, un groupe méthacryloyloxy, un groupe allyle et un groupe vinyle ; et (C) : au moins un initiateur de photopolymérisation.
PCT/JP2019/029854 2018-08-30 2019-07-30 Composition de résine photosensible négative WO2020044918A1 (fr)

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