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WO2012118031A1 - Composition de résine photosensible, film de photoréserve l'utilisant, procédé de formation d'un motif de réserve et procédé de formation d'un motif de conducteur - Google Patents

Composition de résine photosensible, film de photoréserve l'utilisant, procédé de formation d'un motif de réserve et procédé de formation d'un motif de conducteur Download PDF

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Publication number
WO2012118031A1
WO2012118031A1 PCT/JP2012/054824 JP2012054824W WO2012118031A1 WO 2012118031 A1 WO2012118031 A1 WO 2012118031A1 JP 2012054824 W JP2012054824 W JP 2012054824W WO 2012118031 A1 WO2012118031 A1 WO 2012118031A1
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Prior art keywords
resin composition
photosensitive resin
meth
group
acrylate
Prior art date
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Ceased
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PCT/JP2012/054824
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English (en)
Japanese (ja)
Inventor
大貴 豊田
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Nichigo Morton Co Ltd
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Nichigo Morton Co Ltd
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Priority to CN201280011581.8A priority Critical patent/CN103430100B/zh
Priority to KR1020137026142A priority patent/KR101811091B1/ko
Publication of WO2012118031A1 publication Critical patent/WO2012118031A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • 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
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • 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
    • G03F7/085—Photosensitive compositions characterised by adhesion-promoting non-macromolecular additives
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/032—Organic insulating material consisting of one material
    • H05K1/0346—Organic insulating material consisting of one material containing N
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
    • H05K3/06—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed chemically or electrolytically, e.g. by photo-etch process
    • H05K3/061—Etching masks
    • H05K3/064—Photoresists

Definitions

  • the present invention relates to a photosensitive resin composition that can be developed with an alkaline aqueous solution, a photoresist film comprising a photosensitive resin composition layer comprising the photosensitive resin composition and a support layer, and a substrate using the photoresist film.
  • the present invention relates to a method for forming a resist pattern and a method for forming a conductor pattern using the photoresist film.
  • the present invention relates to a photosensitive resin composition that provides a resist pattern suitable for manufacturing a member such as an ITO electrode, an address electrode, or an electromagnetic wave shield in the field of flat panel displays, and a related technique.
  • the photolithographic method is a method in which a photosensitive resin composition is applied onto a substrate, pattern exposure is performed to polymerize and cure the exposed portion of the photosensitive resin composition, and an unexposed portion is removed with a developer to form a resist on the substrate.
  • a method of forming a conductor pattern on a substrate by forming a pattern, forming a conductor pattern by etching or plating, and then peeling and removing the resist pattern from the substrate.
  • a method for producing a printed wiring board using the photoresist film will be briefly described below.
  • a photoresist film has a protective layer, for example, a polyethylene film
  • this is peeled from the photosensitive resin composition layer.
  • a photosensitive resin composition layer and a support layer are laminated on a substrate such as a copper clad laminate using a laminator so that the substrate, the photosensitive resin composition layer, and the support layer are in this order.
  • the exposed portion is polymerized and cured by exposing the photosensitive resin composition layer with active energy rays such as ultraviolet rays including i rays (365 nm) emitted from an ultrahigh pressure mercury lamp through a photomask having a wiring pattern.
  • the support layer for example, a polyethylene terephthalate film is peeled off.
  • an unexposed portion of the photosensitive resin composition layer is dissolved or dispersed and removed with a developer, for example, an aqueous solution having weak alkalinity, to form a resist pattern on the substrate.
  • a developer for example, an aqueous solution having weak alkalinity
  • the process for forming a circuit is roughly divided into two methods.
  • the first method is a method (etching method) in which after removing the copper surface of the substrate not covered with the resist pattern by etching, the resist pattern portion is removed with an alkaline aqueous solution stronger than the developer.
  • the second method is a method (plating method) in which the copper surface of the substrate is plated with copper, solder, and nickel, and then the resist pattern portion is removed and the copper surface of the substrate that appears is etched. is there.
  • a semi-additive construction method is used to create a high-density wiring with a uniform conductor shape.
  • a resist pattern is first formed on a seed copper thin film by the above-described method.
  • plating is performed between the resist patterns to form a plated copper wiring, and after the resist is peeled off, the plated copper wiring and the seed copper thin film are simultaneously etched by a technique called flash etching.
  • the semi-additive method has a thin seed copper thin film and is hardly affected by etching, and can form rectangular and high-density wiring.
  • a semi-cured resist called a soot (cured resist foot) may be generated at the boundary between the cured resist and the substrate after development (see FIG. 1).
  • a soot cured resist foot
  • the surface area of the seed copper thin film that appears after the development due to the soot is reduced, and the ground area of the plated copper wiring formed by the plating method and the copper thin film is reduced. Therefore, it leads to a problem that the plated copper wiring is easily peeled off. Further, since the sushi is under the plated copper wiring, it is caught when the resist is peeled off, which causes a peeling failure.
  • Patent Document 1 proposes a method for preventing halation on the substrate surface of transmitted light and suppressing the generation of sedge by using a triazine compound.
  • Patent Document 2 proposes a method of suppressing the generation of a semi-cured resist (soo) by using a photopolymerizable compound having a fluorene skeleton in the molecule.
  • a photosensitive resin composition having good resolution and adhesion, extremely small susceptibility of the cured resist after development, and good peelability
  • the photosensitive resin Photoresist film comprising a photosensitive resin composition layer comprising a composition and a support layer, a method for forming a resist pattern on a substrate using the photoresist film, and a method for forming a conductor pattern using the photoresist film
  • the purpose is to provide.
  • a photopolymerizable monomer component in a photosensitive resin composition containing a binder polymer as a main component and containing a photopolymerizable monomer and a photopolymerization initiator.
  • a monomer having an amino group and a benzotriazole derivative having a carboxyl group as a peelability-imparting component, high resolution and high adhesiveness are expressed, and the cured resist has a very small skirt after development. It has been found that the peelability is good and the above object can be achieved, and the present invention has been completed.
  • the gist of the present invention includes (A) a binder polymer, (B) a photopolymerizable monomer having an amino group, (C) a photopolymerization initiator, and (D) a benzotriazole derivative having a carboxyl group. It is related with the photosensitive resin composition characterized by these.
  • the present invention also relates to a photoresist film comprising a photosensitive resin composition layer comprising the photosensitive resin composition of the present invention and a support layer.
  • the present invention relates to a method for forming a resist pattern, which includes a step of forming a photosensitive resin composition layer on a substrate using the photoresist film of the present invention, exposing and developing.
  • the present invention also includes a step of forming a photosensitive resin composition layer on a circuit-forming substrate using the photoresist film of the present invention, exposing and developing to form a resist pattern, and the resist pattern It is related with the formation method of the conductor pattern which has the process of etching or plating the said board
  • Photosensitivity comprising (A) a binder polymer, (B) a photopolymerizable monomer having an amino group, (C) a photopolymerization initiator, and (D) a benzotriazole derivative having a carboxyl group. Resin composition.
  • R 1 in the formula is independently each .R 2 and R 3 is H or CH 3, represents a hydrogen atom, an alkyl group, a group selected from the group consisting of alkoxy group and a halogen group, R 2 And R 3 may be bonded to each other to form a ring containing N.
  • X represents an alkylene group having 1 to 10 carbon atoms, or (C 2 H 4 O) m or (C 3 H 6 O) n.
  • M and n are each an integer of 1 to 10 polyoxyalkylene groups, and the polyoxyalkylene groups are random polymerization or block polymerization.
  • the photopolymerizable monomer having an amino group (B) is contained in an amount of 0.01 to 30 parts by weight with respect to 100 parts by weight of the (A) binder polymer [1] or [2] The photosensitive resin composition as described in 2. [4] Any of [1] to [3], wherein (D) the benzotriazole derivative having a carboxyl group is contained in an amount of 0.01 to 2 parts by weight with respect to 100 parts by weight of the (A) binder polymer.
  • a photoresist film comprising a photosensitive resin composition layer comprising the photosensitive resin composition according to any one of [1] to [5] and a support layer.
  • a method for forming a resist pattern comprising forming a photosensitive resin composition layer on a substrate using the photoresist film according to [6], exposing and developing.
  • a photosensitive resin composition layer is formed on a circuit-forming substrate, exposed and developed to form a resist pattern, and the resist pattern
  • a method for forming a conductor pattern comprising: etching or plating the circuit forming substrate on which is formed, and peeling the resist pattern.
  • the photosensitive resin composition and the photoresist film of the present invention have the effect that the resolution and adhesion are good, and the cured resist has a very small skirt and a good peelability after development. Therefore, the resist pattern forming method and the conductor pattern forming method using the photoresist film of the present invention can provide an effect that the resist pattern peeling failure and the conductor pattern (wiring) peeling are reduced.
  • FIG. A shows a cross-sectional view after development, B after plating, and C after peeling.
  • (meth) acryl means acryl or methacryl corresponding thereto
  • (meth) acrylate means acrylate or methacrylate corresponding thereto
  • (meth) acrylo means acrylo or methacrylo corresponding thereto.
  • the photosensitive resin composition of the present invention contains (A) a binder polymer, (B) a photopolymerizable monomer having an amino group, (C) a photopolymerization initiator, and (D) a benzotriazole derivative having a carboxyl group. It is characterized by doing.
  • Examples of the (A) binder polymer include acrylic polymers, styrene polymers, epoxy polymers, amide polymers, amide epoxy polymers, alkyd polymers, phenol polymers, and the like. One of these polymers can be used alone or in combination of two or more. Among these polymers, a carboxyl group-containing polymer is preferable.
  • Examples of the carboxyl group-containing polymer include acrylic polymers, polyester polymers, polyamide polymers, epoxy polymers and the like. Among them, (meth) acrylic acid esters and ethylenically unsaturated carboxylic acids and as necessary. It is preferable to use an acrylic polymer obtained by copolymerizing other copolymerizable monomers.
  • the content of the structural unit based on the (meth) acrylic acid ester is from the viewpoint of improving the alkali developability, resolution, and release properties.
  • the content is preferably 10 to 70 parts by mass, more preferably 20 to 60 parts by mass, and particularly preferably 30 to 50 parts by mass.
  • the content of the structural unit based on the ethylenically unsaturated carboxylic acid is high in resolution and adhesion, soot generation suppression, and peelability. From the viewpoint, it is preferably 12 to 50 parts by mass, more preferably 15 to 40 parts by mass, and particularly preferably 18 to 30 parts by mass. If the content of the ethylenically unsaturated carboxylic acid is too small, the alkali reactivity tends to be inferior and the development time and the peeling time tend to be long. If the content is too large, the developer resistance tends to decrease and the adhesion tends to decrease.
  • the content of structural units based on other copolymerizable monomers is preferably 10 to 80 parts by mass, It is preferably 20 to 70 parts by mass, particularly preferably 30 to 60 parts by mass.
  • These carboxyl group-containing polymers are used alone or in combination of two or more.
  • Examples of the carboxyl group-containing polymer used in combination of two or more types include, for example, two or more types of carboxyl group-containing polymers composed of different copolymerization components, two or more types of carboxyl group-containing polymers having different weight average molecular weights, and different dispersions. And two or more kinds of carboxyl group-containing polymers.
  • the acrylic polymer will be described. However, the acrylic polymer used in the present invention is not limited to the following.
  • Examples of the (meth) acrylic acid ester include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, Aliphatic (meth) acrylates having an alkyl group such as cyclohexyl (meth) acrylate having 1 to 20, preferably 1 to 10 carbon atoms; Aromatic (meth) acrylates such as benzyl (meth) acrylate; Diethylaminoethyl (meth) acrylate Amino group-containing (meth) acrylates such as dimethylaminoethyl (meth) acrylate; hydroxyl-containing (meth) acrylates such as hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate; glycidyl (me
  • Examples of the ethylenically unsaturated carboxylic acid include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid, and dicarboxylic acids such as maleic acid, fumaric acid, and itaconic acid, and anhydrides thereof.
  • Half esters can also be used, and these can be used alone or in combination of two or more. Of these, acrylic acid and methacrylic acid are particularly preferable.
  • Examples of the other copolymerizable monomers include (meth) acrylamide, 2,2,3,3-tetrafluoropropyl (meth) acrylate, acrylamide, diacetone acrylamide, styrene, ⁇ -methylstyrene, vinylnaphthalene, Examples include vinylcyclohexane, vinyltoluene, vinyl acetate, alkyl vinyl ether, (meth) acrylonitrile and the like, and these can be used alone or in combination of two or more.
  • the weight average molecular weight is preferably 50,000 to 200,000, more preferably 10,000 to 100,000, from the viewpoints of resolution and adhesion, soot generation suppression, and peelability.
  • the value is preferably 100 to 300 mgKOH / g, more preferably 120 to 250 mgKOH / g, and particularly preferably 140 to 190 mgKOH / g.
  • the weight average molecular weight (Mw) is a value obtained by measuring a THF (tetrahydrofuran) solution of a dry polymer on a polystyrene basis using a GPC (gel permeation chromatography) apparatus.
  • the acid value is the weight of KOH (potassium hydroxide) necessary to neutralize 1 g of the polymer.
  • the acid value is determined by adding alcohols such as methanol, ketones such as acetone and methyl ethyl ketone, or a mixed solvent thereof. It is measured by neutralizing titrating the dissolved polymer.
  • the weight average molecular weight is too small, the cured photosensitive resin composition tends to be brittle, whereas if it is too large, the resolution and resist peelability tend to decrease.
  • the acid value is too small, the effect of suppressing a decrease in resolution and resist peelability tends to be weakened.
  • the acid value is too large, the effect of suppressing a decrease in fine line adhesion of the cured resist tends to be weakened. is there.
  • the glass transition temperature (Tg) of the acrylic polymer is preferably in the range of 30 to 150 ° C, more preferably in the range of 60 to 120 ° C. If the glass transition temperature is too low, the photosensitive resin composition tends to flow and tends to cause edge fusion when it is rolled into a photoresist film. On the other hand, if the glass transition temperature is too high, it is used as a photoresist film. There is a tendency that the followability to the unevenness of the substrate surface at the time is lowered.
  • the glass transition temperature (Tg) may be measured by DSC (Differential Scanning Colorimetry) or may be calculated using the Fox equation when the glass transition temperature of the homopolymer of the copolymer monomer of the binder polymer is known. it can. In the present invention, it is calculated by the Fox equation.
  • Tg represents the glass transition temperature of the copolymer.
  • Wa, Wb,... represent the weight fraction of the a component, b component,... Ta, Tb,.
  • B represents the glass transition temperature of the homopolymer of component.
  • Examples of the photopolymerizable monomer having an amino group include N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, and diethylaminopropyl (meth).
  • acrylamide normal propyl (meth) acrylamide, isopropyl (meth) acrylamide, N- (meth) acryloylmorpholine, at least one photopolymerizable unsaturated compound selected from the group represented by the following general formula (I) Also mentioned.
  • R 1 in the formula represents H or CH 3 a is .
  • R 2 and R 3 are each independently a hydrogen atom, an alkyl group, a group selected from the group consisting of alkoxy group and a halogen group, R 2 and R 3 may be bonded to each other to form a ring containing N.
  • X represents an alkylene group having 1 to 10 carbon atoms, or (C 2 H 4 O) m or (C 3 H 6 O) n.
  • M and n are each an integer of 1 to 10 polyoxyalkylene groups, and the polyoxyalkylene groups are random polymerization or block polymerization.
  • R 1 in the formula is H or CH 3 .
  • R 2 and R 3 each independently represent a group selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, and a halogen group, and R 2 and R 3 may be bonded to each other to form a ring containing N. good.
  • the alkyl group and alkoxy group usually have 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms.
  • X is an alkylene group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or (C 2 H 4 O) m or (C 3 H 6 O) n, and m and n are each an integer of 1 to 10 It is a polyoxyalkylene group.
  • the polyoxyalkylene group may be random polymerization or block polymerization.
  • Specific examples of the compound represented by the general formula (I) include N, N-dimethylaminomethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, and N, N-dimethyl.
  • the occurrence of scum in the cured resist is due to the partial reaction of the acidic groups of the semi-cured resist, which is weakly cured, with the developer, and the semi-cured resist moves to the bottom of the resist during drying after development without being removed. It is presumed to be.
  • the amino group of the photopolymerizable monomer (B) causes a neutralization reaction with the acidic group in the binder polymer (A) in the photosensitive resin composition, and (A) the acidic group of the binder polymer is covered. It can be considered that the developer resistance is improved and the reattachment of the semi-cured resist is reduced, that is, the sash is reduced.
  • the monomer (B) since the monomer (B) has a photopolymerizable structure, the degree of cure is increased and an improvement in adhesion can be expected. Therefore, the monomer (B) can have the same effect as long as it has an amino group and can be photopolymerized.
  • the content of the photopolymerizable monomer (B) having an amino group is preferably 0.01 to 30 parts by weight, more preferably 0.8 parts per 100 parts by weight of the (A) binder polymer.
  • the amount is 1 to 25 parts by weight, more preferably 0.5 to 20 parts by weight, and particularly preferably 1 to 15 parts by weight.
  • the photopolymerizable monomer shown below can be used together with the photopolymerizable monomer having an amino group.
  • a monomer having one polymerizable unsaturated group 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-phenoxy-2-hydroxy Propyl (meth) acrylate, 2- (meth) acryloyloxy-2-hydroxypropyl phthalate, 3-chloro-2-hydroxypropyl (meth) acrylate, glycerin mono (meth) acrylate, 2- (meth) acryloyloxyethyl acid phosphate , Half (meth) acrylates of phthalic acid derivatives, and the like, and these can be used alone or in combination of two or more.
  • Examples of the monomer having two polymerizable unsaturated groups include, for example, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, Propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polyethylene glycol / polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, oxyethylene group-containing bisphenol A Type di (meth) acrylate, oxypropylene group-containing bisphenol A type di (meth) acrylate, oxyethylene / oxypropylene group-containing bisphenol A type di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, glycerin di (meth)
  • a monomer having three or more polymerizable unsaturated groups for example, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, tri (meth) acryloyl
  • examples thereof include oxyethoxytrimethylolpropane and glycerin polyglycidyl ether poly (meth) acrylate, and these can be used alone or in combination of two or more.
  • urethane (meth) acrylate may be mentioned.
  • urethane (meth) acrylates include diisocyanates such as hexamethylene diisocyanate and tolylene diisocyanate, and hydroxyl groups in one molecule such as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and oligopropylene glycol monomethacrylate.
  • examples thereof include a hydroxyl group-containing (meth) acrylate having a (meth) acryl group and, if necessary, a compound obtained by reacting with a polyol. These may be used alone or in combination of two or more.
  • the total amount of the photopolymerizable monomer (B) having an amino group and the photopolymerizable monomer other than (B) is 10 to 200 parts by weight with respect to 100 parts by weight of the (A) binder polymer. It is preferably 30 to 160 parts by weight, more preferably 50 to 120 parts by weight, and particularly preferably 60 to 100 parts by weight. When the content is too small, curing tends to be insufficient, and when the content is too large, cold flow tends to occur.
  • Examples of (C) photopolymerization initiators include (C1) hexaarylbisimidazole derivatives, (C2) alkylaminobenzophenone derivatives, N-arylglycine derivatives, acridine derivatives, anthraquinone derivatives such as diaminoanthraquinone, N, N, N ', N'-tetraarylbenzidine derivatives, riboflavin triacetate, benzophenone, benzyldimethyl ketal, thioxanthone derivatives, alkylaminobenzoic acid alkyl esters, triazine derivatives, coumarin derivatives such as coumarin 6, triphenylphosphine, tolylphosphine, trixylyl And triarylphosphine such as phosphine, tribiphenylphosphine, trinaphthylphosphine, trianthrylphosphine, triphenanthrylpho
  • Examples of (C1) hexaarylbisimidazole derivatives include 2,2′-bis (2,3-dichlorophenyl) -4,4 ′, 5,5′-tetrakis (3-methoxyphenyl) bisimidazole, 2,2 '-Bis (2,3-dichlorophenyl) -4,4', 5,5'-tetrakis (4-methoxyphenyl) bisimidazole, 2,2'-bis (2,4-dichlorophenyl) -4,4 ', 5,5′-tetrakis (3-methoxyphenyl) phenylbisimidazole, 2,2′-bis (2,5-dichlorophenyl) -4,4 ′, 5,5′-tetrakis (3-methoxyphenyl) bisimidazole, 2,2'-bis (2,6-dichlorophenyl) -4,4 ', 5,5'-tetrakis (3-methoxy
  • Examples of (C2) alkylaminobenzophenone derivatives include 4,4′-bis (diethylamino) benzophenone, 3,3′-dimethyl-4-methoxybenzophenone, 4,4′-bis (dimethylamino) benzophenone, and the like.
  • 4,4′-bis (diethylamino) benzophenone is particularly preferable, and these can be used alone or in combination of two or more.
  • the photosensitive resin composition of the present invention preferably contains at least (C1) hexaarylbisimidazole derivative as the photopolymerization initiator (C) from the viewpoint of increasing sensitivity, and in particular, (C1) hexaarylbis. It preferably contains an imidazole derivative and another photopolymerization initiator, and further preferably contains a (C1) hexaarylbisimidazole derivative and (C2) an alkylaminobenzophenone derivative.
  • the content of the (C) photopolymerization initiator is preferably 1 to 20 parts by weight, particularly 2 to 16 parts by weight, more preferably 3 to 12 parts by weight with respect to 100 parts by weight of the (A) binder polymer. It is preferable that (C) If the content of the photopolymerization initiator is too small, the required sensitivity, resolution, and adhesion tend to be not obtained, and if too large, insoluble matter tends to be generated in the photosensitive resin composition. It is in.
  • (C1) a hexaarylbisimidazole derivative and another photopolymerization initiator are used in combination, for example, when (C1) a hexaarylbisimidazole derivative and (C2) an alkylaminobenzophenone derivative are used in combination, (A) 100 weight of binder polymer
  • the amount of (C1) hexaarylbisimidazole derivative is preferably 1 to 16 parts by weight, particularly 2 to 13 parts by weight, more preferably 3 to 10 parts by weight, and (C2) the alkylaminobenzophenone derivative is 0 parts by weight. It is preferably 0.01 to 4 parts by weight, particularly 0.02 to 3 parts by weight, and more preferably 0.06 to 2 parts by weight.
  • Examples of (D) benzotriazole derivatives having a carboxyl group include 4-carboxybenzotriazole, 5-carboxybenzotriazole, 1- (1 ′, 2′-dicarboxyethyl) benzotriazole, 1- (2 ′, 3 '-Dicarboxypropyl) benzotriazole, 1-((bis (2-ethylhexyl) amino) methyl) -1H-benzotriazolecarboxylic acid is preferably used, and these may be used alone or in combination of two or more. it can. Note that 4-carboxybenzotriazole and 5-carboxybenzotriazole are particularly preferable because of their availability.
  • the benzotriazole derivative is known to have good affinity with copper metal, and it is considered that the benzotriazole derivative is coordinated on the copper substrate after laminating a photoresist film on the copper substrate.
  • the strong alkaline aqueous solution at the time of stripping and the carboxyl group cause a neutralization reaction, so that the resist can be easily stripped from the interface of the copper substrate.
  • the content of the (D) carboxyl group-containing benzotriazole derivative is preferably 0.01 to 2 parts by weight, particularly 0.04 to 1.6 parts by weight, based on 100 parts by weight of the (A) binder polymer. Part, more preferably 0.08 to 1 part by weight.
  • the weight ratio (B) / (D) of the component is preferably in the range of 1 to 500.
  • the weight ratio (B) / (D) is preferably in the range of 3 to 200, and the weight ratio (B) / (D) is preferably in the range of 5 to 50. If the ratio is too low, peeling can be easily performed, but the soot tends to increase. If the ratio is too high, the generation of soot can be suppressed, but the peeling tends to be difficult.
  • the photosensitive resin composition of the present invention preferably further contains a dye.
  • dyes include crystal violet, malachite green, and malachite. Green Lake, Brilliant Green, Diamond Green, Patent Blue, Chill Violet, Victoria Blue, Victoria Pure Blue, Oil Blue, Basic Blue 20, Rose Aniline, Parafuchsin, Ethylene Violet and other Coloring Dyes, Tris (4-Dimethylamino-2- And leuco dyes such as methylphenyl) methane [leuco crystal violet], tris (4-dimethylamino-2-methylphenyl) methane [leucomalachite green], and fluorane dye.
  • the photosensitive resin composition of the present invention may contain a halogen compound.
  • the halogen compound include amyl bromide, isoamyl bromide, isobutylene bromide, ethylene bromide, diphenylmethyl bromide, benzyl bromide, methylene bromide, tribromomethylphenyl sulfone, carbon tetrabromide, tris (2 , 3-dibromopropyl) phosphate, trichloroacetamide, amyl iodide, isobutyl iodide, 1,1,1-trichloro-2,2-bis (p-chlorophenyl) ethane, chlorinated triazine compounds and the like.
  • the photosensitive resin composition of the present invention may contain an additive such as a plasticizer, if necessary.
  • additives include polyethylene glycol, polypropylene glycol, polyoxypropylene polyoxyethylene ether, polyoxyethylene monomethyl ether, polyoxypropylene monomethyl ether, polyoxyethylene polyoxypropylene monomethyl ether, polyoxyethylene monoethyl Glycol esters such as ether, polyoxypropylene monoethyl ether, polyoxyethylene polyoxypropylene monoethyl ether, phthalic acid esters such as diethyl phthalate, o-toluenesulfonic acid amide, p-toluenesulfonic acid amide, citric acid Tributyl, triethyl citrate, acetyl triethyl citrate, acetyl tri-n-propyl citrate, tri-n-acetyl citrate Chill, and the like.
  • the photosensitive resin composition of the present invention it is also possible to contain a radical polymerization inhibitor in the photosensitive resin composition.
  • the radical polymerization inhibitor include p-methoxyphenol, hydroquinone, pyrogallol, naphthylamine, tert-butylcatechol, cuprous chloride, 2,6-di-tert-butyl-p-cresol, 2,2'-methylenebis. (4-methyl-6-tert-butylphenol), 2,2'-methylenebis (4-ethyl-6-tert-butylphenol), nitrosophenylhydroxyamine aluminum salt, diphenylnitrosamine and the like.
  • the photosensitive resin composition of the present invention is optionally mixed with a solvent such as methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N, N-dimethylformamide, propylene glycol monomethyl ether, or a mixed solvent thereof. It is good also as a solution with a solid content of about 30 to 60% by weight. This solution can be used as a coating solution for forming a photosensitive resin composition layer of a photoresist film described later.
  • a solvent such as methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N, N-dimethylformamide, propylene glycol monomethyl ether, or a mixed solvent thereof. It is good also as a solution with a solid content of about 30 to 60% by weight. This solution can be used as a coating solution for
  • a photosensitive resin composition layer by applying this coating solution on a substrate such as a circuit-forming substrate and drying it, from the viewpoint of work efficiency and the like, a photoresist film described later It is preferably used for forming a photosensitive resin composition layer.
  • the photosensitive resin composition of the present invention includes adhesion promoters, antioxidants, thermal polymerization inhibitors, surface tension modifiers, stabilizers, chain transfer agents, antifoaming agents, flame retardants, and the like.
  • An agent may be contained as appropriate, and in such a case, the content is 0.01 to 20 parts by mass with respect to 100 parts by mass of the total solid content of the components (A) to (D). It is preferably contained in an amount of 0.02 to 15 parts by mass, and more preferably 0.03 to 10 parts by mass. These are used alone or in combination of two or more.
  • the photoresist film of the present invention includes a photosensitive resin composition layer comprising a photosensitive resin composition and a support layer.
  • the support layer used here is preferably a transparent layer that transmits light emitted from the exposure light source.
  • a support layer for example, a polyethylene terephthalate film, a polyvinyl alcohol film, a polyvinyl chloride film, a vinyl chloride copolymer film, a polyvinylidene chloride film, a vinylidene chloride copolymer film, a polymethyl methacrylate copolymer film, Examples thereof include a polystyrene film, a polyacrylonitrile film, a styrene copolymer film, a polyamide film, and a cellulose derivative film. Among these, a polyethylene terephthalate film is preferable. These films can be stretched if necessary.
  • the haze of the support layer is preferably 5 or less.
  • a thinner support layer is advantageous in terms of image formation and economy, but a thickness of 10 to 30 ⁇ m is preferably used in order to maintain strength.
  • the thickness of the photosensitive resin composition layer in the photoresist film varies depending on the application, but is preferably 5 to 100 ⁇ m, more preferably 7 to 60 ⁇ m, and particularly preferably 10 to 50 ⁇ m. If the photosensitive resin composition layer is too thin, the film strength tends to be too low, and if it is too thick, the adhesion, sensitivity, and resolution tend to decrease.
  • the photoresist film of the present invention may have a protective layer on the surface opposite to the support layer side of the photosensitive resin composition layer, if necessary.
  • a protective layer is required to be sufficiently smaller than the protective layer.
  • the protective layer for example, a polyethylene film or a polypropylene film can be preferably used.
  • the thickness of the protective layer is preferably 10 to 100 ⁇ m, more preferably 10 to 50 ⁇ m.
  • a coating solution containing the photosensitive resin composition of the present invention is applied to one side of a support layer, dried, and if necessary, the coated surface is coated with a protective layer.
  • a coating liquid containing the photosensitive resin composition of the present invention is uniformly applied to one side of the support layer by a roll coater method, a bar coater method, or the like, and the temperature is gradually increased from 50 to 120 ° C. or higher. It can be manufactured by drying in an oven to form a photosensitive resin composition layer and then pressure laminating a protective layer on the upper surface of the layer.
  • a resist pattern using the photoresist film of the present invention can be formed by a process including a lamination process, an exposure process, and a development process.
  • An example of a specific method is shown below.
  • the substrate to be processed include a copper-clad laminate for the purpose of producing a printed wiring board, and a glass substrate (for example, a substrate for plasma display panel or surface electrolysis for the purpose of producing an uneven substrate). Display substrate), silicone wafers having through-holes, and ceramic substrates.
  • the plasma display panel substrate is a substrate in which an electrode is formed on a glass substrate, a dielectric layer is formed, a partition wall glass paste is applied, and a partition wall glass paste portion is subjected to sandblasting to form a partition wall. It is a material.
  • a lamination process is performed using a laminator.
  • the protective layer is peeled off, and then the photosensitive resin composition layer is heat-pressed and laminated on the surface of the substrate to be processed with a laminator.
  • the photosensitive resin composition layer may be laminated only on one side of the substrate surface, or may be laminated on both sides.
  • the heating temperature at this time is generally 40 to 160 ° C.
  • an exposure process is performed using an exposure machine. If necessary, the support layer is peeled off and exposed to active light through a photomask.
  • the exposure amount is determined by the light source illuminance and the exposure time, but may be measured using a light meter.
  • a direct drawing exposure method may be used.
  • the direct drawing exposure method is a method in which exposure is performed by directly drawing on a substrate without using a photomask.
  • the light source for example, a semiconductor laser having a wavelength of 350 to 410 nm or an ultrahigh pressure mercury lamp is used.
  • the drawing pattern is controlled by a computer, and the exposure amount in this case is determined by the light source illuminance and the moving speed of the substrate.
  • the photosensitive resin composition of the present invention is a dilute alkali development type, a 0.1 to 5% by weight alkaline aqueous solution containing an alkali compound such as sodium carbonate, potassium carbonate or tetramethylammonium hydroxide is used for development. Do it.
  • the pH of the alkaline aqueous solution is preferably in the range of 9 to 11, and the temperature is adjusted according to the developability of the photosensitive resin composition layer.
  • the resist pattern is obtained by the above-described steps, in some cases, a heating step at 100 to 300 ° C. or a UV curing step can be performed. By carrying out these steps, further chemical resistance can be improved.
  • the conductor pattern forming method of the present invention is performed by performing the following steps after performing the above-described resist pattern formation using a circuit-forming substrate such as a copper-clad laminate or a flexible substrate as a base material. First, a conductor pattern is formed on the surface of the substrate exposed by development using a known method such as plating or etching.
  • plating methods used for plating include 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 such as nickel sulfamate Examples thereof include gold plating such as plating, hard gold plating, and soft gold plating.
  • a plating pretreatment agent such as a degreasing agent or a soft etching agent.
  • Etching is usually performed according to a conventional method using an acidic etching solution such as a cupric chloride-hydrochloric acid aqueous solution or a ferric chloride-hydrochloric acid aqueous solution.
  • an ammonia-based alkaline etching solution is also used.
  • an alkali stripping solution composed of an alkaline aqueous solution having a concentration of about 0.1 to 10% by weight containing an alkali compound such as sodium hydroxide or potassium hydroxide, or an organic amine-based stripping of a 3 to 15% by weight aqueous solution.
  • the resist pattern is stripped and removed using a liquid (particularly, one containing monoethanolamine as a main component).
  • a conductor film may be laminated on the resist pattern without removing the resist pattern.
  • flash etching is then performed.
  • the photoresist film in an Example and a comparative example was produced as follows.
  • the solution of the photosensitive resin composition shown in Table 1 was adjusted so that the solid content was 55% by weight, stirred and mixed well, and an applicator was used on a 16 ⁇ m thick polyethylene terephthalate (PET) film as a support film.
  • PET polyethylene terephthalate
  • the coating film thickness after drying was 25 ⁇ m. It dried for 2 minutes each in 60 degreeC and 90 degreeC oven, and also it coat
  • the obtained photoresist film was evaluated as follows.
  • the PET film After exposure, after 15 minutes, the PET film is peeled off and sprayed with a 0.7 wt% sodium carbonate aqueous solution at 27 ° C. for a development time that is twice the breakpoint (time for complete dissolution of the unexposed area). Unexposed portions were dissolved and removed to obtain a cured resist image. From each exposure amount and the number of steps remaining after development, an exposure amount (mJ / cm 2 ) at which the number of remaining step steps after development of the stove 21-step tablet was 6 steps was examined.
  • Adhesion As a mask film at the time of exposure, using a line pattern mask of an exposed portion alone, the exposure was performed with an exposure amount that the number of steps of the step tablet was six, and developed.
  • the minimum mask width ( ⁇ m) at which the cured resist pattern was normally formed was defined as the adhesion value.
  • the photosensitive resin compositions of Examples 1 to 7 are excellent in resolution and adhesion. Furthermore, since the width of the cured resist is small, it is difficult for troubles to occur during subsequent etching or plating. Moreover, since the peelability is also good, stable productivity can be secured.
  • the photosensitive resin compositions of Comparative Examples 1 to 4 were inferior in both resolution and adhesion. Moreover, since the photosensitive resin composition of Comparative Examples 1, 3, and 4 has a large thickness of the cured resist, there is a possibility that troubles may occur during subsequent etching or plating. Furthermore, since the photosensitive resin compositions of Comparative Examples 1 and 2 have poor peelability, it is difficult to obtain a stable throughput.
  • the photosensitive resin composition and the photoresist film of the present invention have the effect that the resolution and adhesion are good, and the cured resist has a very small skirt and a good peelability after development. Therefore, the photosensitive resin composition and the photoresist film of the present invention are suitable as resist materials such as etching resists and plating resists in the fields of production of printed wiring boards, lead frames, semiconductor packages and the like, and precision metal processing. Can be used.

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Abstract

La présente invention concerne une composition de résine photosensible comprenant un polymère liant, un monomère photopolymérisable contenant un groupe amine, un initiateur de photopolymérisation et un dérivé de benzotriazole contenant un groupe carboxyle. La présente invention concerne également un film de photoréserve contenant une couche de la composition de résine photosensible, comprenant la composition de résine photosensible, ainsi qu'une couche de support. La composition de résine photosensible et le film de photoréserve présentent d'excellentes résolution et adhérence, une marge extrêmement réduite sur la réserve durcie après développement et d'excellentes propriétés de démoulage.
PCT/JP2012/054824 2011-03-03 2012-02-27 Composition de résine photosensible, film de photoréserve l'utilisant, procédé de formation d'un motif de réserve et procédé de formation d'un motif de conducteur Ceased WO2012118031A1 (fr)

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CN201280011581.8A CN103430100B (zh) 2011-03-03 2012-02-27 感光性树脂组合物、使用其的光致抗蚀膜、抗蚀图案的形成方法以及导体图案的形成方法
KR1020137026142A KR101811091B1 (ko) 2011-03-03 2012-02-27 감광성 수지 조성물, 이를 이용한 포토레지스트 필름, 레지스터 패턴의 형성 방법 및 도체 패턴의 형성 방법

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JP5990366B2 (ja) * 2011-03-31 2016-09-14 旭化成株式会社 積層体及びそれを用いたロール
JP5842077B1 (ja) * 2015-07-01 2016-01-13 三井金属鉱業株式会社 キャリア付銅箔、銅張積層板及びプリント配線板
JP6567952B2 (ja) * 2015-10-26 2019-08-28 旭化成株式会社 感光性樹脂組成物、感光性樹脂積層体及びレジストパターン形成方法
CN108628093A (zh) * 2017-03-23 2018-10-09 株式会社田村制作所 感光性树脂组合物
CN109388026A (zh) * 2017-08-11 2019-02-26 日兴材料株式会社 光致抗蚀膜、抗蚀图案的形成方法及导体图案的形成方法
JP7190439B2 (ja) * 2017-11-06 2022-12-15 旭化成株式会社 感光性樹脂積層体及びレジストパターンの製造方法
CN110531583B (zh) * 2019-09-14 2023-09-29 浙江福斯特新材料研究院有限公司 感光性树脂组合物、干膜抗蚀层

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JPH07168357A (ja) * 1993-05-14 1995-07-04 E I Du Pont De Nemours & Co 金属をメッキ浴から基体の上にメッキするための方法
JPH07253667A (ja) * 1994-01-10 1995-10-03 E I Du Pont De Nemours & Co 光画像形成可能な液状組成物および乾燥フィルムの製造方法
JP2006519404A (ja) * 2003-02-27 2006-08-24 エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション 感光性組成物及びそれの使用
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JP4931533B2 (ja) * 2005-09-28 2012-05-16 旭化成イーマテリアルズ株式会社 感光性樹脂組成物およびその積層体
CN101568882A (zh) * 2007-02-02 2009-10-28 旭化成电子材料株式会社 感光性树脂组合物及层压体
JP5356934B2 (ja) * 2009-07-02 2013-12-04 太陽ホールディングス株式会社 光硬化性熱硬化性樹脂組成物、そのドライフィルム及び硬化物並びにそれらを用いたプリント配線板

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JPH07168357A (ja) * 1993-05-14 1995-07-04 E I Du Pont De Nemours & Co 金属をメッキ浴から基体の上にメッキするための方法
JPH07253667A (ja) * 1994-01-10 1995-10-03 E I Du Pont De Nemours & Co 光画像形成可能な液状組成物および乾燥フィルムの製造方法
JP2006519404A (ja) * 2003-02-27 2006-08-24 エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション 感光性組成物及びそれの使用
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