WO2022201432A1 - Film de résine photosensible, procédé de formation de motif de réserve et procédé de formation d'un motif de câblage - Google Patents

Film de résine photosensible, procédé de formation de motif de réserve et procédé de formation d'un motif de câblage Download PDF

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Publication number
WO2022201432A1
WO2022201432A1 PCT/JP2021/012569 JP2021012569W WO2022201432A1 WO 2022201432 A1 WO2022201432 A1 WO 2022201432A1 JP 2021012569 W JP2021012569 W JP 2021012569W WO 2022201432 A1 WO2022201432 A1 WO 2022201432A1
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Prior art keywords
photosensitive resin
resin film
resist pattern
forming
mass
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PCT/JP2021/012569
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English (en)
Japanese (ja)
Inventor
穣 川上
尚樹 平松
Original Assignee
昭和電工マテリアルズ株式会社
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Priority to PCT/JP2021/012569 priority Critical patent/WO2022201432A1/fr
Priority to CN202180095650.7A priority patent/CN117099044A/zh
Priority to KR1020237035166A priority patent/KR20230158050A/ko
Priority to JP2023508316A priority patent/JPWO2022201432A1/ja
Publication of WO2022201432A1 publication Critical patent/WO2022201432A1/fr

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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
    • G03F7/027—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
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C08F222/10—Esters
    • 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
    • C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
    • C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—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
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • 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

Definitions

  • the present disclosure relates to a photosensitive resin film, a method of forming a resist pattern, and a method of forming a wiring pattern.
  • photosensitive materials are used as resists for making conductor patterns.
  • a photosensitive resin composition is used to form a resist, and then a conductive pattern, metal posts, and the like are formed by plating. More specifically, a photosensitive layer is formed on a substrate using a photosensitive resin composition or the like, the photosensitive layer is exposed through a predetermined mask pattern, and then a conductor pattern, metal posts, etc. are formed.
  • a resist pattern is formed by developing so that portions can be selectively removed (peeled off). Next, a conductor such as copper is formed on the removed portion by plating, and then the resist pattern is removed to manufacture a wiring board having a conductor pattern, metal posts, etc. (for example, Patent Documents 1 and 2 reference).
  • the photosensitive resin film is required to be capable of forming a thick resist pattern and to shorten the peeling time of the formed resist pattern.
  • the present disclosure has been made in view of the above circumstances, and includes a photosensitive resin film capable of achieving both pattern formability and peeling properties, a method for forming a resist pattern using the same, and a method for forming a wiring pattern. intended to provide
  • a photosensitive resin film according to the present disclosure contains a binder polymer, a photopolymerizable compound containing an acrylate compound, a photopolymerization initiator, and a polymerization inhibitor, and has a thickness of 35 to 300 ⁇ m.
  • a method for forming a resist pattern according to the present disclosure includes the steps of providing a photosensitive layer on a substrate using the photosensitive resin film described above, and irradiating at least a portion of the photosensitive layer with actinic rays to form a photocured portion. and removing at least part of the photosensitive layer other than the photocured portion to form a resist pattern.
  • the method of forming a wiring pattern according to the present disclosure includes the steps of plating a substrate on which a resist pattern is formed by the method of forming a resist pattern to form a conductor pattern, and removing the photocured portion after the plating.
  • a numerical range indicated using “to” indicates a range including the numerical values before and after “to” as the minimum and maximum values, respectively.
  • the upper limit or lower limit of the numerical range at one stage may be replaced with the upper limit or lower limit of the numerical range at another stage.
  • the upper or lower limits of the numerical ranges may be replaced with the values shown in the examples.
  • (meth)acrylic acid means at least one of “acrylic acid” and “methacrylic acid” corresponding thereto, and the same applies to other similar expressions such as (meth)acrylate.
  • the "acrylate compound” includes a compound having an acryloyl group
  • the “methacrylate compound” includes a compound having a methacryloyl group.
  • solid content refers to non-volatile content excluding volatile substances such as water and solvents contained in the photosensitive resin composition, and when the resin composition is dried, It also includes those that are liquid, syrup-like, and wax-like at room temperature around 25°C.
  • the photosensitive resin film according to this embodiment contains a binder polymer, a photopolymerizable compound containing an acrylate compound, a photopolymerization initiator, and a polymerization inhibitor, and has a thickness of 35 to 300 ⁇ m.
  • the photosensitive resin film according to this embodiment can be produced using a photosensitive resin composition containing a binder polymer, a photopolymerizable compound, a photopolymerization initiator, and a polymerization inhibitor.
  • a photosensitive resin composition containing a binder polymer, a photopolymerizable compound, a photopolymerization initiator, and a polymerization inhibitor.
  • the binder polymer (hereinafter also referred to as "(A) component") can be produced, for example, by radically polymerizing a polymerizable monomer.
  • polymerizable monomers include styrene or styrene derivatives, polymerizable monomers having a carboxy group, polymerizable monomers having a hydroxyl group, (meth)acrylic acid benzyl esters, (meth)acrylic acid alkyl esters, Acrylamides such as (meth)acrylic acid tetrahydrofurfuryl ester, (meth)acrylic acid dimethylaminoethyl ester, (meth)acrylic acid diethylaminoethyl ester, (meth)acrylic acid glycidyl ester, diacetone acrylamide, acrylonitrile, alkyl vinyl ether, 2 , 2,2-trifluoroethyl (meth)acrylate, and
  • the (A) component may have a structural unit based on styrene or a styrene derivative from the viewpoint of adhesion and peeling properties.
  • Styrene derivatives are polymerizable compounds such as vinyltoluene, ⁇ -methylstyrene, etc., in which the hydrogen atom at the ⁇ -position or aromatic ring of styrene is substituted.
  • the component (A) can be produced, for example, by radically polymerizing a polymerizable monomer containing styrene or a styrene derivative and another polymerizable monomer.
  • the content of structural units based on styrene or styrene derivatives in component (A) may be 15 to 64% by mass, 25 to 60% by mass, 35 to 55% by mass, or 45 to 50% by mass.
  • the content of the structural unit based on styrene or a styrene derivative is 15% by mass or more, the adhesion tends to be improved, and when it is 64% by mass or less, it is possible to suppress the size of the peeled pieces during development and shorten the time required for peeling. There is a tendency to suppress prolongation.
  • the (A) component may have a carboxy group from the viewpoint of alkali developability.
  • the polymerizable monomer having a carboxyl group include (meth)acrylic acid, ⁇ -bromoacrylic acid, ⁇ -chloroacrylic acid, ⁇ -furyl (meth)acrylic acid, ⁇ -styryl (meth)acrylic acid, ) Maleic acid monoesters such as acrylic acid, maleic acid, maleic anhydride, monomethyl maleate, monoethyl maleate, monoisopropyl maleate, fumaric acid, cinnamic acid, ⁇ -cyanocinnamic acid, itaconic acid, crotonic acid, and propiolic acid.
  • the polymerizable monomer having a carboxy group may be (meth)acrylic acid or methacrylic acid.
  • the content of the structural unit based on the polymerizable monomer having a carboxy group is 10 to 50% by mass, based on the total amount of the component (A). It may be 15 to 40% by mass, or 20 to 35% by mass.
  • the content of the structural unit based on the polymerizable monomer having a carboxy group is 10% by mass or more, the alkali developability tends to be improved, and when it is 50% by mass or less, the alkali resistance tends to be excellent.
  • the (A) component may have a hydroxyl group from the viewpoint of subdividing the exfoliated pieces.
  • Polymerizable monomers having a hydroxyl group include, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3 - hydroxyl group-containing (meth)acrylates such as hydroxybutyl (meth)acrylate and 4-hydroxybutyl (meth)acrylate; and hydroxyl group-containing vinyl ethers such as 2-hydroxyethyl vinyl ether, 3-hydroxypropyl vinyl ether and 4-hydroxybutyl vinyl ether. be done.
  • the content of the structural unit based on the polymerizable monomer having a hydroxyl group is 0.5 to 15% by mass based on the total amount of component (A). , 1 to 10% by weight, or 2 to 5% by weight.
  • the component (A) may have a structural unit based on benzyl (meth)acrylate.
  • the content of structural units derived from (meth)acrylic acid benzyl ester in component (A) is 5 to 40% by mass, 10 to 35% by mass, or 15 to 30% by mass from the viewpoint of improving resolution and aspect ratio. %.
  • the (A) component may have a structural unit based on a (meth)acrylic acid alkyl ester from the viewpoint of improving the plasticity of the resist pattern.
  • (meth)acrylic acid alkyl esters include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, and (meth)acrylate.
  • the acid value of component (A) is 100 to 220 mgKOH/g, 120 to 210 mgKOH/g, 140 to 200 mgKOH/g, 160 to 195 mgKOH/g, or It may be 170-190 mg KOH/g.
  • the weight average molecular weight (Mw) of component (A) may be 10,000 to 100,000, 15,000 to 80,000, 18,000 to 60,000, 20,000 to 50,000, or 25,000 to 40,000. When the Mw of the component (A) is 10,000 or more, the developer resistance of the photocured portion tends to be excellent.
  • Component (A) may have a dispersity (weight average molecular weight/number average molecular weight) of 1.0 to 3.0, or 1.0 to 2.0. Resolution tends to improve as the degree of dispersion decreases.
  • the weight average molecular weight and number average molecular weight in this specification are values measured by gel permeation chromatography (GPC) and converted from standard polystyrene as a standard sample.
  • the (A) component can be used singly or in combination of two or more.
  • the component (A) when two or more are used in combination for example, two or more binder polymers composed of different polymerizable monomers, two or more binder polymers having different Mw, and different dispersities. Two or more binder polymers are included.
  • the content of component (A) is 30 to 80 parts by mass, 40 to 75 parts by mass, 50 to 70 parts by mass, or 50 to It may be 60 parts by mass. When the content of the component (A) is within this range, the strength of the photocured portion of the photosensitive resin film and the photosensitive layer will be better.
  • the photosensitive resin film forms a thick resist pattern with excellent adhesion during development.
  • component (B) a photopolymerizable compound
  • the time required for stripping the formed resist pattern can be shortened.
  • the present inventors presume that the acryloyl group has no methyl group, is less hydrophobic than the methacryloyl group, and has no steric hindrance due to the methyl group, making it easier to remove the resist pattern with a stripping solution.
  • the acrylate compound is not particularly limited as long as it has at least one acryloyl group, and may have two or more acryloyl groups.
  • acrylate compounds include acrylates having a polyhydric alcohol-derived skeleton, acrylates having a urethane bond, acrylates having a bisphenol skeleton, acrylates having an alicyclic skeleton, acrylates having a phthalic acid skeleton, nonylphenoxypolyethyleneoxyacrylate, and acrylic acid alkyl esters.
  • An acrylate compound can be used individually by 1 type or in combination of 2 or more types.
  • acrylates having a polyhydric alcohol-derived skeleton include polyalkylene glycol diacrylate, trimethylolpropane diacrylate, trimethylolpropane triacrylate, EO-modified trimethylolpropane triacrylate, PO-modified trimethylolpropane triacrylate, EO, Examples include PO-modified trimethylolpropane triacrylate, tetramethylolmethane triacrylate, tetramethylolmethane tetraacrylate, and acrylates having a skeleton derived from dipentaerythritol or pentaerythritol.
  • EO-modified means having a block structure of ethylene oxide (EO) groups
  • PO-modified means having a block structure of propylene oxide (PO) groups.
  • a polyalkylene glycol diacrylate may have at least one of an EO group and a PO group, or may have both an EO group and a PO group.
  • the EO groups and PO groups may be present continuously in blocks or randomly.
  • the PO group may be either an oxy-n-propylene group or an oxyisopropylene group.
  • the secondary carbon of the propylene group may be bonded to the oxygen atom, or the primary carbon may be bonded to the oxygen atom.
  • the acrylate having a urethane bond includes, for example, an acrylic monomer having an OH group at the ⁇ -position and a diisocyanate (isophorone diisocyanate, 2,6-toluene diisocyanate, 2,4-toluene diisocyanate, 1,6-hexamethylene diisocyanate, etc.).
  • a diisocyanate isophorone diisocyanate, 2,6-toluene diisocyanate, 2,4-toluene diisocyanate, 1,6-hexamethylene diisocyanate, etc.
  • Addition reactants tris(acryloxytetraethyleneglycol isocyanate) hexamethylene isocyanurate, EO-modified urethane diacrylate, and EO,PO-modified urethane diacrylate.
  • acrylates having a bisphenol skeleton examples include 2,2-bis(4-(acryloxypolyethoxy)phenyl)propane, 2,2-bis(4-(acryloxypolypropoxy)phenyl)propane, 2,2- Bis(4-(acryloxypolybutoxy)phenyl)propane and 2,2-bis(4-(acryloxypolyethoxypolypropoxy)phenyl)propane.
  • 2,2-bis(4-(acryloxypolyethoxy)phenyl)propane is preferable from the viewpoint of further improving pattern formability.
  • an acrylate having an alicyclic hydrocarbon group having 5 to 20 carbon atoms can be used as the acrylate having an alicyclic hydrocarbon group having 5 to 20 carbon atoms.
  • Alicyclic skeletons include, for example, cyclopentane, cyclohexane, cyclooctane, cyclodecane, norbornane, dicyclopentane, and tricyclodecane.
  • the acrylate compound may be an acrylate having a tricyclodecane skeleton in order to further improve the peeling properties.
  • Examples of acrylates having an alicyclic skeleton include dicyclopentenyl acrylate, dicyclopentanyl acrylate, dicyclopentenyloxyethyl acrylate, cyclohexyl acrylate, cyclohexyl diacrylate, and tricyclodecane dimethanol diacrylate.
  • Examples of commercial products of tricyclodecanedimethanol diacrylate include A-DCP (tricyclodecanedimethanol diacrylate, manufactured by Shin-Nakamura Chemical Co., Ltd.).
  • acrylates having a phthalic acid skeleton include ⁇ -chloro- ⁇ -hydroxypropyl- ⁇ '-acryloyloxyethyl-o-phthalate, ⁇ -hydroxyethyl- ⁇ '-acryloyloxyethyl-o-phthalate, and ⁇ - Hydroxypropyl- ⁇ '-acryloyloxyethyl-o-phthalate can be mentioned.
  • nonylphenoxypolyethyleneoxyacrylate examples include nonylphenoxytetraethyleneoxyacrylate, nonylphenoxypentaethyleneoxyacrylate, nonylphenoxyhexaethyleneoxyacrylate, nonylphenoxyheptaethyleneoxyacrylate, nonylphenoxyoctaethyleneoxyacrylate, nonylphenoxynonaethyleneoxy acrylates, nonylphenoxydecaethyleneoxy acrylate, and nonylphenoxyundecaethyleneoxy acrylate.
  • Component (B) preferably contains a diacrylate having two acryloyl groups as an acrylate compound from the viewpoint of further improving the balance between pattern formability and peeling properties. More preferably it contains an acrylate.
  • the (B) component may further contain a methacrylate compound.
  • methacrylate compounds include methacrylates having a polyhydric alcohol-derived skeleton, methacrylates having a urethane bond, methacrylates having a bisphenol skeleton, methacrylates having an alicyclic skeleton, methacrylates having a phthalic acid skeleton, nonylphenoxypolyethyleneoxymethacrylate, and methacrylic acid alkyl esters.
  • methacrylate compound a compound obtained by changing the acryloyl group of the acrylate compound described above to a methacryloyl group can be used.
  • a methacrylate compound can be used individually by 1 type or in combination of 2 or more types.
  • the amount of the acrylate compound contained in component (B) is preferably 5% by mass or more, based on the total amount of component (B), from the viewpoint of shortening the resist pattern stripping time, 10% by mass or more, 15% by mass, It may be 80% by mass or more, or 20% by mass or more, and from the viewpoint of improving the resolution of the resist pattern, it is preferably 85% by mass or less, and 80% by mass or less, 75% by mass or less, or 70% by mass or less. may be
  • the photopolymerization initiator (hereinafter also referred to as “component (C)" is not particularly limited as long as it can polymerize the component (B). It can be selected as appropriate.
  • the component (C) may contain a hexaarylbiimidazole derivative or an acridine compound having one or more acridinyl groups in order to improve sensitivity and resolution in a well-balanced manner.
  • Component can be used individually by 1 type or in combination of 2 or more types.
  • hexaarylbiimidazole derivatives include 2-(o-chlorophenyl)-4,5-diphenylbiimidazole, 2,2′,5-tris-(o-chlorophenyl)-4-(3,4-dimethoxyphenyl )-4′,5′-diphenylbiimidazole, 2,4-bis-(o-chlorophenyl)-5-(3,4-dimethoxyphenyl)-diphenylbiimidazole, 2,4,5-tris-(o- chlorophenyl)-diphenylbiimidazole, 2-(o-chlorophenyl)-bis-4,5-(3,4-dimethoxyphenyl)-biimidazole, 2,2′-bis-(2-fluorophenyl)-4,4 ',5,5'-tetrakis-(3-methoxyphenyl)-biimidazole, 2,2'-bis-(2,3
  • acridine compounds include 9-phenylacridine, 9-(p-methylphenyl)acridine, 9-(m-methylphenyl)acridine, 9-(p-chlorophenyl)acridine, 9-(m-chlorophenyl)acridine, 9-aminoacridine, 9-dimethylaminoacridine, 9-diethylaminoacridine, 9-pentylaminoacridine, 1,2-bis(9-acridinyl)ethane, 1,4-bis(9-acridinyl)butane, 1,6- bis(9-acridinyl)hexane, 1,8-bis(9-acridinyl)octane, 1,10-bis(9-acridinyl)decane, 1,12-bis(9-acridinyl)dodecane, 1,14-bis( 9-acridinyl)tetradecane,
  • the content of component (C) is 0.5 to 10 parts by mass, 1 to 8 parts by mass, or 2 to 5 parts by mass with respect to the total amount of 100 parts by mass of components (A) and (B). may When the content of component (C) is 0.5 parts by mass or more, photosensitivity, resolution and adhesion tend to be improved, and when it is 10 parts by mass or less, resist pattern formability tends to be more excellent.
  • the photosensitive resin film according to the present embodiment can improve the pattern formability by containing (D) a polymerization inhibitor (hereinafter also referred to as "(D) component").
  • (D) component can be used individually by 1 type or in combination of 2 or more types.
  • the component (D) may contain a compound represented by the following formula (I) from the viewpoint of further improving the pattern formability.
  • R 5 is a halogen atom, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an amino group, an aryl group, a mercapto group, or a It represents an alkylmercapto group, a carboxylalkyl group having 1 to 10 carbon atoms in the alkyl group, an alkoxy group having 1 to 20 carbon atoms, or a heterocyclic group.
  • the aryl group may be substituted with an alkyl group having 1 to 20 carbon atoms.
  • R 5 may be a hydrogen atom or an alkyl group having 1 to 20 carbon atoms from the standpoint of further improving compatibility with component (A).
  • the alkyl group having 1 to 20 carbon atoms represented by R 5 may be an alkyl group having 1 to 4 carbon atoms.
  • m may be 2 or 3, or may be 2 from the standpoint of further improving resolution.
  • Examples of compounds represented by the above formula (I) include catechol, 2-methylcatechol, 3-methylcatechol, 4-methylcatechol, 2-ethylcatechol, 3-ethylcatechol, 4-ethylcatechol, 2-propyl catechol, 3-propylcatechol, 4-propylcatechol, 2-n-butylcatechol, 3-n-butylcatechol, 4-n-butylcatechol, 2-tert-butylcatechol, 3-tert-butylcatechol, 4-tert Catechol compounds such as -butylcatechol and 3,5-di-tert-butylcatechol; Resorcinol compounds such as resorcinol, 2-propylresorcinol, 4-propylresorcinol, 2-n-butylresorcinol, 4-n-butylresorcinol, 2-tert-butylresorcinol, 4-tert-butylresorcinol; 1,4-hydroquinone, hydroquinone compounds such as
  • the (D) component may contain a catechol compound from the viewpoint of improving resolution.
  • the catechol compounds include 2-methylcatechol, 3-methylcatechol, 4-methylcatechol, 2-ethylcatechol, 3-ethylcatechol, 4-ethylcatechol, 2-propylcatechol, 3-propylcatechol, 4-propylcatechol, 2-n-butylcatechol, 3-n-butylcatechol, 4-n-butylcatechol, 2-tert-butylcatechol, 3-tert-butylcatechol, 4-tert-butylcatechol, 3,5-di-tert- Alkylcatechols such as butylcatechol are preferred, with 3-tert-butylcatechol, 4-tert-butylcatechol, or 3,5-di-tert-butylcatechol being more preferred.
  • the content of component (D) is 0.010 to 0.30 parts by mass, 0.015 to 0.20 parts by mass, or 0.020 parts by mass based on 100 parts by mass of the total amount of components (A) and (B). It may be up to 0.10 parts by mass.
  • the exposure time can be shortened.
  • the photoreaction of the photocured portion can be sufficiently advanced, and the pattern formability can be further enhanced.
  • the photosensitive resin composition according to the present embodiment may optionally contain a sensitizer, a dye, a photocoloring agent, a thermal coloration inhibitor, a plasticizer, a pigment, a filler, an antifoaming agent, a flame retardant, and adhesion.
  • Additives such as imparting agents, leveling agents, release accelerators, antioxidants, fragrances, imaging agents, thermal cross-linking agents, and polymerization inhibitors may be further contained. These additives can be used singly or in combination of two or more.
  • Sensitizers include, for example, dialkylaminobenzophenone compounds, pyrazoline compounds, anthracene compounds, coumarin compounds, xanthone compounds, thioxanthone compounds, oxazole compounds, benzoxazole compounds, thiazole compounds, benzothiazole compounds, triazole compounds, stilbene compounds, and triazine compounds. , thiophene compounds, naphthalimide compounds, triarylamine compounds, and aminoacridine compounds.
  • the content of the sensitizer is 0.01 to 1 part by mass, 0.02 to 0.02 part by mass, per 100 parts by mass of the total amount of components (A) and (B). It may be 5 parts by weight, 0.03 to 0.2 parts by weight, or 0.04 to 0.1 parts by weight.
  • Dyes include, for example, malachite green, victoria pure blue, brilliant green, and methyl violet.
  • Photochromic agents include, for example, tribromophenylsulfone, leucocrystal violet, diphenylamine, benzylamine, triphenylamine, diethylaniline, and o-chloroaniline.
  • Plasticizers include, for example, p-toluenesulfonamide.
  • FIG. 1 is a schematic cross-sectional view showing one embodiment of a photosensitive resin film.
  • the photosensitive resin film 1 according to this embodiment may be formed on the support film 2 using the photosensitive resin composition described above.
  • the photosensitive resin film according to this embodiment can be used in the form of a photosensitive element including a support film 2 and a photosensitive resin film 1 provided on the support film 2 as shown in FIG.
  • the thickness of the photosensitive resin film 1 is 35-300 ⁇ m.
  • the thickness of the photosensitive resin film 1 may be 40 ⁇ m or more, 45 ⁇ m or more, or 50 ⁇ m or more from the viewpoint of forming a wiring pattern with a high aspect ratio. From the viewpoint of peelability of the photosensitive resin film, the thickness of the photosensitive resin film 1 may be 250 ⁇ m or less, 200 ⁇ m or less, or 150 ⁇ m or less.
  • polyester films such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT) and polyethylene-2,6-naphthalate (PEN), and polyolefin films such as polypropylene and polyethylene.
  • PET polyethylene terephthalate
  • PBT polybutylene terephthalate
  • PEN polyethylene-2,6-naphthalate
  • polyolefin films such as polypropylene and polyethylene.
  • the haze of the support film may be 0.01-5.0%, 0.01-1.5%, 0.01-1.0%, or 0.01-0.5% .
  • Haze refers to a value measured using a commercially available cloudiness meter (turbidity meter) in accordance with the method specified in JIS K7105. Haze can be measured with a commercially available turbidity meter such as NDH-5000 (manufactured by Nippon Denshoku Industries Co., Ltd., trade name).
  • the thickness of the support film may be 1-200 ⁇ m, 1-100 ⁇ m, 1-60 ⁇ m, 5-60 ⁇ m, 10-60 ⁇ m, 10-50 ⁇ m, 10-40 ⁇ m, 10-30 ⁇ m, or 10-25 ⁇ m.
  • the thickness of the support film is 1 ⁇ m or more, it tends to be possible to suppress the support film from tearing when the support film is peeled off. Further, when the thickness of the support film is 200 ⁇ m or less, there is a tendency to easily obtain an economic benefit.
  • a protective film may be laminated on the surface of the photosensitive resin film 1 opposite to the support film 2 .
  • a polymer film such as polyethylene or polypropylene may be used as the protective film.
  • the same polymer film as the support film may be used, or a different polymer film may be used. It is preferable that the adhesive force between the protective film and the photosensitive resin film 1 is smaller than the adhesive force between the support film 2 and the photosensitive resin film 1 .
  • the photosensitive resin film 1 can be formed, for example, by applying a photosensitive resin composition onto the support film 2 and then drying it. Coating can be performed using known methods such as roll coating, comma coating, gravure coating, air knife coating, die coating, and bar coating. Drying can be performed at 70 to 150° C. for about 5 to 30 minutes.
  • a solvent may be added to the photosensitive resin composition to use a solution having a solid content of about 30 to 60% by mass.
  • Solvents include, for example, methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N,N-dimethylformamide, and propylene glycol monomethyl ether.
  • a solvent can be used individually by 1 type or in combination of 2 or more types. In this case, the amount of residual solvent in the photosensitive resin film is preferably 2% by mass or less in order to prevent the solvent from diffusing in subsequent steps.
  • the form of the photosensitive element is not particularly limited.
  • it may be in the form of a sheet, or may be in the form of a roll wound around a core.
  • the film When wound into a roll, the film may be wound with the support film on the outside.
  • the winding core include plastics such as polyethylene resin, polypropylene resin, polystyrene resin, polyvinyl chloride resin, and ABS resin (acrylonitrile-butadiene-styrene copolymer).
  • an end face separator may be installed from the viewpoint of end face protection, or a moisture-proof end face separator may be installed from the viewpoint of edge fusion resistance.
  • the photosensitive element may be packaged by wrapping it in a black sheet with low moisture permeability.
  • the photosensitive resin film according to the present embodiment has excellent pattern formability, it is possible to form a resist pattern with a high aspect ratio.
  • the method of forming a resist pattern comprises a step of providing a photosensitive layer on a substrate using the photosensitive resin film described above (hereinafter also referred to as a “photosensitive layer forming step”), and at least one step of forming the photosensitive layer.
  • a step of irradiating the part with actinic rays to form a photocured part (hereinafter also referred to as an “exposure step”), and a step of removing at least a part of the photosensitive layer other than the photocured part to form a resist pattern. (hereinafter also referred to as “development step”).
  • a resist pattern can be called a photocured product pattern of a photosensitive resin film, and can be called a relief pattern.
  • the method of forming a resist pattern can also be said to be a method of manufacturing a substrate with a resist pattern.
  • the photosensitive layer forming step when the photosensitive element is used, if the photosensitive element has a protective film, remove it, and then heat the photosensitive resin film to about 70 to 130 ° C. while heating under reduced pressure or at normal temperature. Under reduced pressure, the photosensitive layer is formed on the substrate by pressure-bonding to the substrate at a pressure of about 0.1 to 1 MPa (about 1 to 10 kgf/cm 2 ).
  • a copper-clad laminate is used in which a layer made of an insulating material such as a glass fiber reinforced epoxy resin is provided with a copper foil on one side or both sides thereof.
  • Exposure methods include a method of irradiating actinic rays imagewise through a negative or positive mask pattern called artwork (mask exposure method), a method of imagewise irradiating actinic rays by a projection exposure method, LDI (Laser Direct Imaging) exposure method, DLP (Digital Light Processing) exposure method, and other direct drawing exposure methods can be used to imagewise irradiate actinic rays.
  • artwork mask exposure method
  • LDI Laser Direct Imaging
  • DLP Digital Light Processing
  • a light source for actinic rays known light sources can be used.
  • a material that effectively emits ultraviolet rays and visible light is used.
  • post-exposure baking may be performed after exposure and before development.
  • the temperature when performing PEB may be 50-100°C.
  • a heater a hot plate, a box-type dryer, a heating roll, or the like may be used.
  • the development step at least a portion of the photosensitive layer other than the photocured portion is removed from the substrate, thereby forming a resist pattern on the substrate.
  • Developing methods include wet development and dry development, and wet development is widely used.
  • development is performed by a known development method using a developer corresponding to the photosensitive resin composition.
  • the developing method include methods using a dipping method, a paddle method, a spray method, brushing, slapping, scrubbing, rocking immersion, etc.
  • a high-pressure spray method may be used from the viewpoint of improving resolution. Development may be performed by combining two or more of these methods.
  • the composition of the developer is appropriately selected according to the composition of the photosensitive resin composition.
  • Examples of the developer include alkaline aqueous solutions and organic solvent developers.
  • an alkaline aqueous solution may be used as the developer.
  • the base of the alkaline aqueous solution includes, for example, alkali hydroxides such as lithium, sodium or potassium hydroxide; alkali carbonates such as lithium, sodium, potassium or ammonium carbonates or bicarbonates; potassium phosphate, sodium phosphate alkali metal phosphates such as sodium pyrophosphate, alkali metal pyrophosphates such as potassium pyrophosphate; borax, sodium metasilicate, tetramethylammonium hydroxide, ethanolamine, ethylenediamine, diethylenetriamine, 2-amino-2-hydroxy Methyl-1,3-propanediol, 1,3-diaminopropanol-2, and morpholine.
  • alkali hydroxides such as lithium, sodium or potassium hydroxide
  • alkali carbonates such as lithium, sodium, potassium or ammonium carbonates or bicarbonates
  • potassium phosphate sodium phosphate alkali
  • alkaline aqueous solutions used for development include 0.1 to 5% by mass sodium carbonate aqueous solution, 0.1 to 5% by mass potassium carbonate aqueous solution, and 0.1 to 5% by mass aqueous sodium hydroxide solution.
  • the pH of the alkaline aqueous solution may be in the range of 9 to 11, and the temperature of the alkaline aqueous solution can be adjusted according to the developability of the photosensitive layer.
  • a surfactant, an antifoaming agent, and a small amount of organic solvent for promoting development may be mixed in the alkaline aqueous solution.
  • Organic solvents used in the alkaline aqueous solution include, for example, acetone, ethyl acetate, alkoxyethanol having an alkoxy group having 1 to 4 carbon atoms, ethyl alcohol, isopropyl alcohol, butyl alcohol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol.
  • Monobutyl ether may be mentioned.
  • organic solvents used in organic solvent developers include 1,1,1-trichloroethane, N-methylpyrrolidone, N,N-dimethylformamide, cyclohexanone, methylisobutylketone, and ⁇ -butyrolactone.
  • the organic solvent may be used as an organic solvent developer by adding water in the range of 1 to 20% by mass.
  • heating at about 60 to 250° C. or exposure at about 0.2 to 10 J/cm 2 is performed as necessary. may include a step of further hardening the resist pattern.
  • the method for forming a wiring pattern according to the present embodiment includes a step of plating a substrate on which a resist pattern has been formed by the method of forming a resist pattern to form a conductor pattern, and removing the photocured portion after the plating. Have a process.
  • a resist pattern formed on a substrate with a conductor layer is used as a mask to plate copper, solder, or the like on the conductor layer of the substrate that is not covered with resist.
  • the resist is removed by removing the resist pattern, which will be described later, and the conductor layer covered with the resist is etched to form a conductor pattern.
  • the plating method may be electroplating or electroless plating, and electroless plating may be used.
  • Electroless plating includes, for example, copper plating such as copper sulfate plating and copper pyrophosphate plating, solder plating such as high-throw solder plating, Watt bath (nickel sulfate-nickel chloride) plating, nickel plating such as nickel sulfamate plating, Gold plating such as hard gold plating and soft gold plating can be used.
  • the resist pattern on the substrate is removed.
  • the resist pattern can be removed, for example, with a stronger alkaline aqueous solution than the alkaline aqueous solution used in the developing step.
  • a strong alkaline aqueous solution for example, a 1 to 10% by mass sodium hydroxide aqueous solution, a 1 to 10% by mass potassium hydroxide aqueous solution, or the like is used. Among these, a 1 to 5% by mass aqueous sodium hydroxide solution or an aqueous potassium hydroxide solution may be used.
  • the desired printed wiring board can be manufactured by further etching the conductor layer covered with the resist by etching to form a conductor pattern.
  • the etching method at this time is appropriately selected according to the conductor layer to be removed.
  • the etchant described above can be applied.
  • Methods for removing the resist pattern include, for example, an immersion method and a spray method, which may be used alone or in combination.
  • FIG. 2 shows one aspect of the process of forming a wiring pattern using the photosensitive resin film according to this embodiment.
  • the photosensitive layer 20 is formed by laminating the photosensitive resin film 1 on the substrate 10 in which the conductive layer is formed on the insulating layer by the photosensitive layer forming step.
  • the photosensitive layer 20 is irradiated with actinic rays 30 in the exposure process described above to form a photocured portion in the photosensitive layer 20 .
  • a resist pattern 22, which is a photocured portion is formed on the substrate 10 by removing regions other than the photocured portion formed by the exposure step from the substrate by a development step.
  • a plating layer 40 is formed on the substrate 10 not covered with the resist by plating using the resist pattern 22 as a mask.
  • the resist pattern 22, which is the photo-cured portion is peeled off with a strong alkaline aqueous solution to form a conductor pattern 42.
  • the photosensitive resin film according to the present embodiment has excellent pattern formability even if it is a thick film, and the formed resist pattern has excellent peeling properties. It can be suitably used for
  • Weight average molecular weight 120 mg of the binder polymer solution was collected and dissolved in 5 mL of THF to prepare a sample for Mw measurement. Mw was derived by measuring by gel permeation chromatography (GPC) and converting using a standard polystyrene calibration curve. The conditions of GPC are shown below.
  • ((C) photoinitiator) B-CIM 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (Changzhou Power Electronics New Materials Co., Ltd.)
  • TBC 4-tert-butyl catechol (DIC Corporation)
  • a solution of a photosensitive resin composition is uniformly applied onto a polyethylene terephthalate (PET) film (manufactured by Toray Industries, Inc., trade name: FB-40) with a thickness of 16 ⁇ m, and dried at 70° C. for 10 minutes using a hot air convection dryer. and dried at 100° C. for 10 minutes to form a photosensitive layer on one side of the PET film as the support film.
  • PET polyethylene terephthalate
  • a copper clad laminate (manufactured by Showa Denko Materials Co., Ltd., trade name “MCL-E-67”) in which copper foil (thickness: 12 ⁇ m) is laminated on both sides of a glass fiber reinforced epoxy resin layer is washed with water, pickled and washed with water. It was then dried in an air stream. Then, the copper-clad laminate was heated to 80° C. to laminate a photosensitive resin film on the copper surface of the copper-clad laminate. Lamination was carried out using heat rolls at 110° C. at a pressure of 0.4 MPa and a roll speed of 1.0 m/min. Thus, a laminate was obtained in which the copper-clad laminate, the photosensitive layer and the PET film were laminated in this order.
  • a 41-step tablet having a density range of 0.00 to 2.00, a density step of 0.05, a tablet size of 20 mm ⁇ 187 mm, and each step size of 3 mm ⁇ 12 mm was applied.
  • a photo tool was placed.
  • the photosensitive layer was exposed with a predetermined amount of energy using a parallel light exposure device (manufactured by ORC Manufacturing Co., Ltd., product name "EXM-1201") using a high-pressure mercury lamp as a light source.
  • a photomask PKG R&D Test Pattern No. 2 was applied as a negative for evaluation. 2 (negative for evaluation: having a wiring pattern with a line width/space width of x/250 (x: 2 to 30, unit: ⁇ m)), and the number of remaining steps after development of a 41-step tablet was 14. Exposure was performed with an energy amount of 0. After the exposure, the PET film was peeled off, and a 1% by weight sodium carbonate aqueous solution at 30° C. was sprayed for twice the shortest development time (shortest time for removing the unexposed portion) to remove the unexposed portion.
  • Photosensitive resin film 1... Photosensitive resin film, 2... Support film, 10... Substrate, 20... Photosensitive layer, 22... Resist pattern, 30... Active ray, 40... Plating layer, 42... Conductor pattern.

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Abstract

La présente invention concerne : un film de résine photosensible qui contient un polymère liant, un composé photopolymérisable comprenant un composé acrylate, un initiateur de photopolymérisation et un inhibiteur de polymérisation, et dont l'épaisseur est de 35 à 300 µm ; un procédé de formation d'un motif de réserve à l'aide du film de résine photosensible ; et un procédé de formation d'un motif de câblage.
PCT/JP2021/012569 2021-03-25 2021-03-25 Film de résine photosensible, procédé de formation de motif de réserve et procédé de formation d'un motif de câblage WO2022201432A1 (fr)

Priority Applications (4)

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PCT/JP2021/012569 WO2022201432A1 (fr) 2021-03-25 2021-03-25 Film de résine photosensible, procédé de formation de motif de réserve et procédé de formation d'un motif de câblage
CN202180095650.7A CN117099044A (zh) 2021-03-25 2021-03-25 感光性树脂膜、抗蚀剂图案的形成方法及配线图案的形成方法
KR1020237035166A KR20230158050A (ko) 2021-03-25 2021-03-25 감광성 수지 필름, 레지스트 패턴의 형성 방법, 및 배선 패턴의 형성 방법
JP2023508316A JPWO2022201432A1 (fr) 2021-03-25 2021-03-25

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PCT/JP2021/012569 WO2022201432A1 (fr) 2021-03-25 2021-03-25 Film de résine photosensible, procédé de formation de motif de réserve et procédé de formation d'un motif de câblage

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007114731A (ja) * 2005-09-20 2007-05-10 Hitachi Chem Co Ltd 感光性エレメント
WO2009133817A1 (fr) * 2008-04-28 2009-11-05 日立化成工業株式会社 Composition de résine photosensible, élément photosensible, procédé de formation d’un motif de réserve et procédé de fabrication de carte de circuit imprimé
JP2016031503A (ja) * 2014-07-30 2016-03-07 日立化成株式会社 導電パターンの形成方法、導電パターン基板及びタッチパネルセンサ
WO2017018053A1 (fr) * 2015-07-29 2017-02-02 日立化成株式会社 Composition de résine photosensible, élément photosensible, procédé de formation d'un motif de réserve et procédé de production de carte imprimée

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4108243B2 (ja) 1999-04-14 2008-06-25 旭化成エレクトロニクス株式会社 感光性樹脂積層体
DE102006056073A1 (de) 2006-11-28 2008-05-29 Arvinmeritor Emissions Technologies Gmbh Krümmer für eine Abgasanlage

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007114731A (ja) * 2005-09-20 2007-05-10 Hitachi Chem Co Ltd 感光性エレメント
WO2009133817A1 (fr) * 2008-04-28 2009-11-05 日立化成工業株式会社 Composition de résine photosensible, élément photosensible, procédé de formation d’un motif de réserve et procédé de fabrication de carte de circuit imprimé
JP2016031503A (ja) * 2014-07-30 2016-03-07 日立化成株式会社 導電パターンの形成方法、導電パターン基板及びタッチパネルセンサ
WO2017018053A1 (fr) * 2015-07-29 2017-02-02 日立化成株式会社 Composition de résine photosensible, élément photosensible, procédé de formation d'un motif de réserve et procédé de production de carte imprimée

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