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  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
  • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
  • C08G65/4006—(I) or (II) containing elements other than carbon, oxygen, hydrogen or halogen as leaving group (X)
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  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
  • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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  • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
  • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B27/00—Layered products comprising a layer of synthetic resin
  • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
  • B32B27/285—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyethers
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  • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
  • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
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  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/062—Polyethers
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  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
  • C08F290/14—Polymers provided for in subclass C08G
  • C08F290/142—Polyethers
• • 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
  • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
  • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
• • C—CHEMISTRY; METALLURGY
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  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
  • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
  • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
  • C08G65/4031—(I) or (II) containing nitrogen
  • C08G65/4037—(I) or (II) containing nitrogen in ring structure, e.g. pyridine group
• • C—CHEMISTRY; METALLURGY
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  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
  • C08G65/48—Polymers modified by chemical after-treatment
  • C08G65/485—Polyphenylene oxides
• • C—CHEMISTRY; METALLURGY
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  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
  • C08G73/12—Unsaturated polyimide precursors
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/34—Silicon-containing compounds
  • C08K3/36—Silica
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/14—Peroxides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
  • C08K5/3415—Five-membered rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
  • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
  • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
  • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
  • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
  • C08L79/085—Unsaturated polyimide precursors
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
  • C09J171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
  • C09J171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
• • 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
  • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
• • 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
  • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
  • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/20—Exposure; Apparatus therefor
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/26—Processing photosensitive materials; Apparatus therefor
  • G03F7/30—Imagewise removal using liquid means
  • G03F7/32—Liquid compositions therefor, e.g. developers
  • G03F7/325—Non-aqueous compositions
• • 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
  • H05K1/0326—Organic insulating material consisting of one material containing O
• • 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
  • H05K1/00—Printed circuits
  • H05K1/02—Details
  • H05K1/03—Use of materials for the substrate
  • H05K1/0313—Organic insulating material
  • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
  • H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
• • 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
  • H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
  • H05K2201/02—Fillers; Particles; Fibers; Reinforcement materials
  • H05K2201/0203—Fillers and particles
  • H05K2201/0206—Materials
  • H05K2201/0209—Inorganic, non-metallic particles

Definitions

• the present invention relates to a radiation-sensitive composition for forming an insulating film, a patterned resin film, and a semiconductor circuit substrate.
• insulating films used in semiconductor circuit boards are required to have a low dielectric constant and a low dielectric loss tangent in a high frequency region (see Patent Document 1, for example).
• a composition for forming a resin film such as an insulating film having a pattern (hereinafter also referred to as "patterned resin film”) must have photolithographic properties that enable patterning by exposure and development.
• the present invention is intended to solve the above problems, and is capable of forming a resin film having a low dielectric constant, a low dielectric loss tangent, excellent stretchability and high reliability, and a photolithographic property for forming an insulating film.
• a radiation composition to provide a patterned resin film having a low dielectric constant, a low dielectric loss tangent, excellent elongation and high reliability, and a method for producing the same, and a low dielectric constant, a low dielectric loss tangent, and a low elongation It is an object of the present invention to provide a semiconductor circuit board including a patterned resin film having excellent properties and high reliability.
• the inventors of the present invention have made intensive studies to solve the above problems. As a result, the inventors have found that the above problems can be solved by a radiation-sensitive composition for forming an insulating film containing a specific polyfunctional compound, a specific polymer and a photopolymerization initiator, and have completed the present invention. Embodiment examples of the present invention are shown below.
• the polymer (B) is a polymer having a repeating structural unit represented by the following formula (a2), A radiation-sensitive composition for forming an insulating film, wherein the group Y is represented by the following formula (Y1).
• two Xs each independently represent a single bond, an oxygen atom, a sulfur atom, an amide bond, -NH-C(O)-NH- or -SO2- , and at least one X is an oxygen atom, a sulfur atom, an amide bond, -NH-C(O)-NH- or -SO 2 -;
• R a21 represents a divalent hydrocarbon group or a divalent group in which a hydrogen atom in the divalent hydrocarbon group is substituted with a functional group other than a heterocyclic ring
• R a22 represents a divalent hydrocarbon group, a divalent group in which a hydrogen atom in the divalent hydrocarbon group is substituted with a functional group other than a heterocyclic ring, or a heterocyclic ring-containing group
• R a21 and R a22 may have the group Y described above.
• R Y1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
• L Y1 is a single bond, an alkanediyl group having 1 to 5 carbon atoms, —C(O)O—, —NH —C(O)—NH— or a group combining these
• * indicates the position of bonding with the main chain or side chain constituting the polymer (B).
• the polymer (B) is a polymer having a repeating structural unit represented by the following formula (a2), A radiation-sensitive composition for forming an insulating film, wherein the group Y is represented by the following formula (Y1).
• two Xs each independently represent a single bond, an oxygen atom, a sulfur atom, an amide bond, -NH-C(O)-NH- or -SO2- , and at least one X is an oxygen atom, a sulfur atom, an amide bond, -NH-C(O)-NH- or -SO 2 -;
• R a21 represents a divalent hydrocarbon group or a divalent group in which a hydrogen atom in the divalent hydrocarbon group is substituted with a functional group other than a heterocyclic ring
• R a22 represents a divalent hydrocarbon group, a divalent group in which a hydrogen atom in the divalent hydrocarbon group is substituted with a functional group other than a heterocyclic ring, or a heterocyclic ring-containing group
• R a21 and R a22 may have the group Y described above.
• R Y1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms
• L Y1 is a single bond, an alkanediyl group having 1 to 5 carbon atoms, —C(O)O—, —NH —C(O)—NH— or a group combining these
• * indicates the position of bonding with the main chain or side chain constituting the polymer (B).
• a radiation-sensitive composition for forming an insulating film which is capable of forming a resin film having a low dielectric constant, a low dielectric loss tangent, excellent stretchability and high reliability, and having photolithographic properties. Also, a patterned resin film having a low dielectric constant, a low dielectric loss tangent, excellent elongation and high reliability, a method for producing the same, and a pattern having a low dielectric constant, a low dielectric loss tangent, excellent elongation and high reliability A semiconductor circuit board including a modified resin film can be provided.
• the radiation-sensitive composition for forming an insulating film of the present invention (hereinafter also simply referred to as "the composition of the present invention") is selected from polyfunctional maleimide compounds (A-1) and polyfunctional styryl compounds (A-2). a polymer (B) having a group Y that reacts with the maleimide group of the polyfunctional maleimide compound (A) or the styryl group of the polyfunctional styryl compound (A-2), and It contains a photoinitiator (C).
• the polyfunctional compound (A) used in the present invention is at least one selected from polyfunctional maleimide compounds (A-1) and polyfunctional styryl compounds (A-2).
• the polyfunctional maleimide compound (A-1) used in the present invention is a compound having 2 or more, preferably 3 or more maleimide groups in the molecule, and the upper limit of the number of maleimide groups is preferably 10, more preferably 4.
• the maleimide group is a group that directly acts on the group Y, which will be described later, during photocrosslinking, thermal crosslinking, etc., and it is believed that, for example, the following reactions proceed.
• composition of the present invention contains the polyfunctional maleimide compound (A-1), it is possible to form a crosslinked structure in such a manner that the group Y of the polymer (B) is consumed during exposure, and reliability is improved. It is possible to obtain a cured film with a high
• polyfunctional maleimide compound (A-1) examples include compounds represented by formula (A1) (hereinafter also referred to as "crosslinkable maleimide compound (A1)").
• crosslinkable maleimide compound (A1)) By using the crosslinkable maleimide compound (A1), the cured film formed from the composition of the present invention can more effectively exhibit the above elongation and reliability improvement effects.
• R A1 is an organic group, and examples of the organic group include aromatic ring-containing groups such as alkanediyl groups and arylene groups, alicyclic-containing groups such as cycloalkylene groups, and groups obtained from unsaturated fatty acids. and a group derived from dimer acid.
• the number of carbon atoms in the alkanediyl group is usually 1-20, preferably 2-10.
• aromatic ring-containing groups and alicyclic-containing groups include arylene groups having 6 to 20 carbon atoms and cycloalkylene groups having 3 to 20 carbon atoms, groups represented by -ZX A1 -Z-, - A group represented by ZOZX A1 -ZOZ- and a group represented by -R A2 -Z-R A2 - are exemplified.
• Z is a benzene ring or a cyclohexane ring, each independently having one or more substituents such as an alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 6 carbon atoms.
• X A1 is a direct bond, —O—, —SO 2 —, an alkanediyl group having 1 to 10 carbon atoms, or an alicyclic-containing group having 3 to 20 carbon atoms.
• R A2 is an alkanediyl group having 1 to 10 carbon atoms.
• the alkanediyl group includes a methylene group, an ethanediyl group, a propanediyl group, a hexanediyl group, an octanediyl group, a nonanediyl group, a decanediyl group, and the like.
• the arylene group includes phenylene group, methylphenylene group, t-butylphenylene group, naphthylene group and the like.
• the cycloalkylene group includes a cyclobutanediyl group, a cyclopentanediyl group, a cyclohexanediyl group, and the like.
• alkyl groups include methyl, ethyl, and propyl groups.
• the alkoxy group includes a methoxy group, an ethoxy group, and the like.
• the alicyclic ring includes cyclohexane ring, tricyclodecane ring and the like.
• crosslinkable maleimide compound (A1) examples include N,N'-ethylenebismaleimide, N,N'-hexamethylenebismaleimide, N,N'-(2,2,4-trimethylhexane)bis Maleimide ("BMI-TMH” manufactured by Daiwa Kasei Kogyo Co., Ltd.), N,N'-p-phenylene bismaleimide, N,N'-m-phenylene bismaleimide (manufactured by Daiwa Kasei Kogyo Co., Ltd.
• BMI-3000 N,N'-4-methyl-1,3-phenylenebismaleimide
• BMI-7000 manufactured by Daiwa Kasei Kogyo Co., Ltd.
• N,N'-2,4-tolylenebismaleimide N,N' -2,6-tolylenebismaleimide
• N,N'-p-xylylenebismaleimide N,N'-m-xylylenebismaleimide
• N,N'-(1,3-dimethylenecyclohexane)bismaleimide N,N'-(1,4-dimethylenecyclohexane)bismaleimide
• N,N'-(4,4'-biphenylene)bismaleimide N,N'-(4,4'-diphenylmethane)bismaleimide
• BMI-1000 manufactured by Daiwa Kasei Kogyo Co., Ltd.
• crosslinkable maleimide compound (A1) examples include bis[4-(4-maleimidophenoxy)phenyl]methane, 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, bis[4 -(4-maleimidophenoxy)phenyl]octane, bis[4-(4-maleimidophenoxy)phenyl]decane, bis[4-(4-maleimidophenoxy)phenyl]cyclohexane, bis[4-(4-maleimidophenoxy)phenyl ]-tricyclo-[5.2.1. O 2.6 ]decane.
• At least one hydrogen atom in the benzene ring and the cyclohexane ring in the exemplary compound may be independently substituted with a C 1-10 alkyl group.
• alkyl groups include methyl, ethyl, and propyl groups.
• a bismaleimide compound in which both ends of polyoxyalkylenediamine are blocked with maleic anhydride can also be used.
• the polyfunctional maleimide compound (A-1) is a compound represented by formula (0) described in WO 2019/167359, wherein at least two R 1A have a substituent.
• a polyfunctional maleimide compound having a maleimide group having 4 to 30 carbon atoms can also be used.
• various polyfunctional maleimide compounds obtained by the methods described in [0207] to [0255] of WO2019/167359 can also be used.
• a dialdehyde compound having a phenolic hydroxyl group as shown below can be used as aldehydes used in the method described in International Publication No. 2019/167359. Thereby, a polyfunctional maleimide compound having a phenolic hydroxyl group can be obtained.
• Examples of the polyfunctional maleimide (A-1) containing a polyfunctional maleimide compound having a phenolic hydroxyl group obtained by the method described in International Publication No. 2019/167359 include the compound (A-1) represented by the following formula (M1): -M1), or multimers of said compound (A-M1).
• each R M11 independently represents a monovalent organic group having a hydroxyl group or a maleimide group
• R M12 represents a hydroxyl group, an alkoxy group or a thiol group
• L M11 represents a single bond, an alkanediyl group having 1 to 5 carbon atoms, a divalent aromatic ring-containing group, or a group combining these
• n M11 represents an integer of 1 to 4
• Two or more of the plurality of R M11 are monovalent organic groups having a maleimide group.
• alkanediyl group having 1 to 5 carbon atoms examples include methylene group, ethanediyl group, propanediyl group, butanediyl group and pentanediyl group.
• divalent aromatic ring-containing group examples include the same groups as those exemplified as the aromatic ring-containing group in the formula (A1).
• Examples of the monovalent organic group having a maleimide group include groups represented by the following formulas (M31) to (M33).
• R M311 is an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, and a cycloalkoxy group having 3 to 10 carbon atoms. represents an aryl group having 6 to 15 carbon atoms, an aryloxy group having 6 to 15 carbon atoms, or a hydroxyl group; n M311 represents an integer of 0 to 4;
• R M321 is an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, and a cycloalkoxy group having 3 to 10 carbon atoms. represents an aryl group having 6 to 15 carbon atoms, an aryloxy group having 6 to 15 carbon atoms, or a hydroxyl group; n M321 represents an integer of 0 to 4 ;
• R M331 is an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, and a cycloalkoxy group having 3 to 10 carbon atoms. represents an aryl group having 6 to 15 carbon atoms, an aryloxy group having 6 to 15 carbon atoms, or a hydroxyl group; n M331 represents an integer of 0 to 4 ;
• Examples of the group represented by the formula (M31) include an N-phenylmaleimide group, a 3-ethyl-5-methyl-4-maleimidophenyl group, a 3-methoxy-4-maleimidophenyl group, a 3-phenyl-4 - maleimidophenyl group.
• Examples of multimers of the compound (A-M1) include compounds (A-M2) represented by the following formula (M2).
• each R M21 independently represents a hydrogen atom or a maleimide group
• R M12 , L M11 and n M11 are synonymous with R M12 , L M11 and n M11 in formula (M1)
• n M22 represents an integer of 1 to 10
• Two or more of the plurality of R M21 are maleimide groups.
• a commercially available product may be used as the polyfunctional maleimide compound (A-1).
• Commercially available products of the polyfunctional maleimide compound (A-1) include, for example, “BMI-2000” and “BMI-2300” manufactured by Daiwa Kasei Kogyo Co., Ltd. represented by the following formula (M41); “MIR-3000” manufactured by Nippon Kayaku Co., Ltd., “MIR-5000” manufactured by Nippon Kayaku Co., Ltd.; “SLK-3000”, “SLK-6895”, “SLK-1500”, “SLK- 2500” and “SLK-6100”.
• n M411 in the above formula (M41) represents the number of repeating units, n M411 ⁇ 2 for BMI-2000, and n M411 ⁇ 2 to 5 for BMI-2300. Further, n M421 in the above formula (M42) represents the number of repeating units, and in the case of MIR-3000, n M421 ⁇ 2-5 .
• the polyfunctional maleimide compound (A-1) can be used alone or in combination of two or more.
• the polyfunctional styryl compound (A-2) used in the present invention is a compound having 2 or more, preferably 3 or more styryl groups in the molecule, and the upper limit of the number of styryl groups is preferably 10, more preferably 4.
• a styryl group is a group that directly acts on a group Y, which will be described later, during photocrosslinking, thermal crosslinking, etc., and it is believed that the following reaction proceeds, for example.
• R in the above formula represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms.
• the polyfunctional styryl compound (A-2) in the composition of the present invention it is possible to form a crosslinked structure in such a manner that the group Y of the polymer (B) is consumed during exposure, thereby improving reliability. It is possible to obtain a cured film with a high
• polyfunctional styryl compounds (A-2) examples include compounds represented by formula (A2) (hereinafter also referred to as "crosslinkable styryl compounds (A2)").
• A2 crosslinkable styryl compounds
• the cured film formed from the composition of the present invention can further exhibit the effect of improving elongation and reliability.
• n A2 is an integer of 2 or more, preferably 2 to 10, more preferably 2 to 6, and R A2 is an n A2 -valent organic compound obtained by removing n A2 hydrogen atoms from an organic compound. is the base.
• the organic group include aliphatic hydrocarbon compounds, aromatic hydrocarbon compounds, heterocyclic compounds, and compounds containing two or more of these, such as a single bond, —O—, —S—, —SO 2 —, A group obtained by removing n A2 hydrogen atoms from a compound linked by -NR N1 -, -CO-, -COO- or -CONH- may be mentioned.
• RN1 is a hydrogen atom or a group obtained by removing one hydrogen atom from the above organic compound.
• R A3 is a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms.
• R A4 is an alkyl group having 1 to 10 carbon atoms.
• n A4 is an integer of 0-4.
• each group may be the same or different.
• the number of carbon atoms in the aliphatic hydrocarbon compound is usually 1-20, preferably 2-10.
• aromatic ring hydrocarbon compounds include aromatic hydrocarbon compounds having 6 to 20 carbon atoms such as benzene, naphthalene, anthracene, and fluorene.
• Heterocyclic compounds include nitrogen-containing heterocycles such as pyrrole, imidazole, pyrazole, pyridine, pyrimidine, triazine, pyridazine and pyrazine; oxygen-containing heterocycles such as furan and pyran; sulfur-containing heterocycles such as thiophene and thioxanthene; oxazole, thiazole, etc. containing a heteroatom of
• polycyclic styryl compound (A2) examples include divinylbenzene and compounds represented by the following formula.
• At least one hydrogen atom in the benzene ring in the exemplified compounds may be independently substituted with an alkyl group having 1 to 10 carbon atoms.
• alkyl groups include methyl, ethyl, and propyl groups.
• the polyfunctional styryl compound (A-2) can be used alone or in combination of two or more. It is also preferable to use the polyfunctional styryl compound (A-2) together with the polyfunctional maleimide compound (A-1). By using the polyfunctional styryl compound (A-2) and the polyfunctional maleimide compound (A-1) in combination, the residual film ratio (ratio at which the patterned thin film appropriately remains) is improved.
• the total content of the polyfunctional compound (A) is usually 0.1 to 200 parts by mass, preferably 1 to 100 parts by mass, with respect to 100 parts by mass of the polymer (B), More preferably, it is 5 to 50 parts by mass.
• the content of the polyfunctional compound (A) is within the above range, the cured film obtained from the composition of the present invention is excellent in both photolithography properties, chemical resistance and crack resistance.
• the polymer (B) used in the present invention is a group Y (hereinafter referred to as “reactive group Y”) and a repeating structural unit represented by the following formula (a2) (hereinafter also referred to as “repeating structural unit (a2)”), wherein the group Y is represented by the following formula (Y1).
• the polymer (B) may be a polymer having one repeating structural unit (a2) or a polymer having two or more repeating structural units (a2).
• Two Xs in formula (a2) each independently represent an oxygen atom, a sulfur atom, an amide bond, —NH—C(O)—NH— or —SO 2 —, and at least one X is oxygen atom, sulfur atom, amide bond, -NH-C(O)-NH- or -SO 2 -.
• the composition of the present invention can be used to form a patterned resin film having a low dielectric constant, a low dielectric loss tangent, and excellent elongation.
• An oxygen atom, an amide bond and -NH-C(O)-NH- are preferred because of their excellent stability.
• R a21 is a divalent hydrocarbon group or a divalent group in which a hydrogen atom in the divalent hydrocarbon group is substituted with a functional group other than a heterocyclic ring (hereinafter referred to as “bivalent Also referred to as "substituted hydrocarbon group").
• R a21 may have the group Y described above.
• R a22 is a divalent hydrocarbon group, a divalent group in which a hydrogen atom in the divalent hydrocarbon group is substituted with a functional group other than a heterocyclic ring (a divalent substituted hydrocarbon group), or a heterocyclic ring-containing group.
• R a22 may have the group Y described above.
• R a21 is preferably a divalent hydrocarbon group
• R a22 is preferably a heterocyclic ring-containing group or a divalent hydrocarbon group that does not have the reactive group. Heterocyclic-containing groups are more preferred.
• the dipole moment in the minor axis direction of the polymer (B) (perpendicular to the main chain direction of the polymer (B)) becomes small, and the composition of the present invention is used. It is preferable because a patterned resin film having a low dielectric constant, a low dielectric loss tangent, and excellent elongation can be formed.
• divalent hydrocarbon groups in R a21 and R a22 include alkanediyl groups, alicyclic-containing hydrocarbon groups, and aromatic ring-containing hydrocarbon groups.
• an aromatic ring-containing hydrocarbon group is preferable because it can form a patterned resin film having a uniform thickness.
• a hydrocarbon group having both an alicyclic ring and an aromatic ring is classified as an aromatic ring-containing hydrocarbon group.
• the carbon number of the alkanediyl group is usually 1-30, preferably 1-20.
• alkanediyl groups include methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, hexane-1,6-diyl group, octane-1,8-diyl group,
• a straight-chain alkanediyl group such as decane-1,10-diyl group; one or more side chains comprising an alkyl group having 1 to 4 carbon atoms are added to the straight-chain alkanediyl groups exemplified above.
• a branched alkanediyl group can be mentioned.
• the number of carbon atoms in the alicyclic-containing hydrocarbon group is generally 3-30, preferably 5-20.
• the alicyclic ring that is, the aliphatic hydrocarbon ring includes, for example, monocyclic aliphatic hydrocarbon rings such as cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclodecane ring; norbornane ring, norbornene ring, adamantane ring , tricyclo[5.2.1.0 2,6 ]decane ring and tricyclo[5.2.1.0 2,6 ]heptane ring.
• the alicyclic-containing hydrocarbon group can have the aliphatic hydrocarbon ring, for example, as a monovalent group (e.g., cycloalkyl group) or as a divalent group (e.g., cycloalkanediyl group);
• a group in which at least one hydrogen atom in an alkanediyl group is substituted with a monovalent aliphatic hydrocarbon ring, and a group in which a divalent aliphatic hydrocarbon ring and an alkanediyl group are linked are exemplified.
• the aromatic ring-containing hydrocarbon group includes, for example, an arylene group and a divalent group represented by -R 3 -Ar-R 3 -.
• Ar is an arylene group
• R 3 is each independently an alkanediyl group (the alkanediyl group usually has 1 to 6 carbon atoms).
• an arylene group means a divalent hydrocarbon group having one or more aromatic rings, i.e., an aromatic hydrocarbon ring, and having two bonds on the aromatic hydrocarbon ring. .
• the arylene group has a plurality of aromatic hydrocarbon rings, the two bonds may exist on the same aromatic hydrocarbon ring or different aromatic hydrocarbon rings.
• the aromatic hydrocarbon ring contained in the arylene group includes, for example, a benzene ring; a benzo-condensed ring such as a naphthalene ring, anthracene ring, tetracene ring, and pentacene ring.
• the arylene group preferably has 6 to 50 carbon atoms, more preferably 6 to 30 carbon atoms.
• the arylene group includes, for example, a phenylene group, a naphthalenediyl group, an anthracenediyl group, a tetracenediyl group, a pentacenediyl group, and divalent groups represented by the following formulas (a1-1) to (a1-4).
• Each aromatic hydrocarbon ring (eg, benzene ring) contained in these groups can have one or more substituents, and the substituents include, for example, an alkyl group having 1 to 30 carbon atoms, a cyclo Examples include alkyl groups, aryl groups, and aralkyl groups. When the aromatic hydrocarbon ring has two or more substituents, each substituent may be the same or different.
• each Z is independently a single bond or a divalent hydrocarbon group having 1 to 20 carbon atoms; preferably a divalent hydrocarbon group having 1 to 20 carbon atoms.
• n is an integer of 0-3.
• the divalent hydrocarbon group having 1 to 20 carbon atoms include alkanediyl groups such as methylene group, ethylene group, 1,1-dimethylmethane-1,1-diyl group and decane-1,1-diyl group.
• aryl group-substituted alkanediyl group such as diphenylmethylene group
• cycloalkanediyl group such as cyclohexane-1,1-diyl group and 3,3,5-trimethylcyclohexane-1,1-diyl group
• phenylene group, fluorenylidene group are mentioned.
• each R 11 is independently a hydrogen atom or an alkyl group, preferably an alkyl group having 1 to 10 carbon atoms.
• the divalent substituted hydrocarbon group for R a21 and R a22 is a group in which a functional group other than the reactive group and the heterocyclic ring is introduced into the divalent hydrocarbon group.
• the functional group include groups other than the reactive groups, which are selected from halogen atoms, nitro groups, cyano groups, allyl groups, and vinyl groups.
• the functional group is preferably not a highly polar functional group such as a hydroxyl group.
• the heterocyclic ring-containing group for R a22 includes, for example, a cyclic imide group, an alicyclic imide ring-containing group having a structure in which a cyclic imide group is fused to an alicyclic hydrocarbon group, a heteroaromatic ring-containing group, and an aromatic ring.
• aromatic imide ring-containing groups having a structure in which a cyclic imide group is condensed examples of the alicyclic imide ring-containing group having a structure in which the cyclic imide group is condensed to the cyclic imide group or the alicyclic hydrocarbon group include groups represented by the following formulae.
• heteroaromatic ring examples include N-containing aromatic rings such as pyrimidine ring, pyrazine ring, pyridazine ring, pyridine ring, pyrrole ring, and pyrazole ring; O-containing aromatic rings such as furan rings; S-containing aromatic rings such as thiophene rings. N- and O-containing aromatic rings such as benzoxazole ring and isoxazole ring; and N- and S-containing aromatic rings such as isothiazole ring.
• aromatic imide ring-containing group examples include a phthalimide group.
• the heterocyclic ring may have one or more, for example 1 to 2, substituents bonded to the heterocyclic ring, and the substituents include, for example, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, and an allyl group. and a monovalent hydrocarbon group having 1 to 20 carbon atoms such as a vinyl group, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, a nitro group, and a cyano group, and other than the reactive group groups.
• the functional group is preferably not a highly polar functional group such as a hydroxyl group.
• the number of carbon atoms in the hydrocarbon group and the halogenated hydrocarbon group is preferably 1-3. When a heterocycle has more than one substituent, each substituent may be the same or different.
• a benzoxazole ring-containing group, an aromatic imide ring-containing group, and a pyrimidine group can form a patterned resin film excellent in low dielectric constant and low dielectric loss tangent using the composition of the present invention.
• a divalent group obtained by removing two hydrogen atoms from pyrazine or pyridazine more preferably a divalent group obtained by removing two hydrogen atoms from pyrimidine, pyrazine or pyridazine, and removing two hydrogen atoms from pyrimidine are particularly preferred.
• R Y1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
• alkyl groups having 1 to 5 carbon atoms include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, sec -pentyl group and 3-pentyl group.
• R Y1 is preferably a hydrogen atom, a methyl group or an ethyl group, more preferably a hydrogen atom or a methyl group.
• L Y1 represents a single bond, an alkanediyl group having 1 to 5 carbon atoms, —C(O)O—, —NH—C(O)—NH—, or a group combining these.
• alkanediyl group having 1 to 5 carbon atoms include methylene group, ethylene group, propanediyl group, butanediyl group and pentanediyl group.
• L Y1 is preferably a single bond, methylene group, ethylene group, —C(O)O—, —NH—C(O)—NH—, —C(O)O—(CH 2 ) y —, —C (O)O-(CH 2 ) y -OC(O)- or -C(O)O-(CH 2 ) y -NH-C(O)-NH- (y is an integer of 1 to 3) and more preferably a single bond, —C(O)O—(CH 2 ) 2 —OC(O)— or —C(O)O—(CH 2 ) 2 —NH—C(O)—NH— is.
• R a21 is preferably an aromatic ring-containing hydrocarbon group, more preferably an arylene group.
• R a22 is preferably an aromatic ring-containing hydrocarbon group or a heterocyclic ring-containing group, and is an arylene group or a divalent group obtained by removing two hydrogen atoms from pyrimidine. is more preferable.
• the composition of the present invention can be used to form a patterned resin film excellent in low dielectric constant and low dielectric loss tangent.
• Preferred embodiments of the polymer (B) include polyimides, polyimide precursors, polybenzoxazoles, polybenzoxazole precursors and polyphenylene ethers.
• the polymer (B) is a linear polymer having the group Y at the polymer chain end, particularly a linear polymer represented by the following formula (BB). can be used to form a patterned resin film with excellent elongation.
• R a21 , R a22 and X have the same meanings as in formula (a2), and R a23 and R a24 have the same meanings as R a21 and R a22 respectively.
• Y means the reactive group Y described above.
• n indicates that the structure in parentheses is a repeating structural unit, that is, the repeating structural unit (a2) is ...- Ra22 -X- Ra21 -X- Ra22 -X- Ra21 -X- are connected like
• the repeating structural unit (a2) may be of one type or two or more types.
• Each of m and p independently represents an integer of 0 or 1 or more, preferably 0 or an integer of 1-10, more preferably 0 or an integer of 1-5.
• R a25 and R a26 have the same meanings as R a21 and R a22 , respectively, but when a reactive group Y is bonded, they have valences according to the number of reactive groups Y.
• q and r each independently represent an integer of 2 or more, preferably an integer of 2-8, more preferably an integer of 2-4.
• the content of the repeating structural unit (a2) is usually 30% by mass or more, preferably 50% by mass or more, more preferably 70% by mass or more, based on 100% by mass of the polymer (B). Preferably, it is 90% by mass or more.
• the composition of the present invention tends to have excellent resolution, and the resin film obtained from the composition of the present invention tends to have a low dielectric constant, a low dielectric loss tangent, and excellent elongation.
• the content of repeating structural units (a2) can be measured by 13 C-NMR.
• the group Y contained in the polymer (B) can be analyzed qualitatively or quantitatively by combining the matrix-assisted laser desorption ionization method, the three-dimensional nuclear magnetic resonance method, the titration method, and the like.
• the weight average molecular weight (Mw) of the polymer (B) measured by gel permeation chromatography is determined from the viewpoint of the resolution of the composition of the present invention and the elongation of the resin film obtained from the composition of the present invention.
• Mw weight average molecular weight
• polystyrene in terms of polystyrene, is usually 1,000 to 200,000, preferably 2,000 to 100,000, more preferably 5,000 to 100,000.
• the details of the method for measuring Mw are as described in Examples.
• the polymer (B) may be used alone or in combination of two or more.
• the lower limit of the content of the polymer (B) in 100% by mass of the solid content of the composition of the present invention is usually 20% by mass, preferably 40% by mass, more preferably 60% by mass; It is usually 99% by mass, preferably 95% by mass.
• the content of the polymer (B) is at least the lower limit value or at most the upper limit value, there is a tendency to obtain a radiation-sensitive composition for forming an insulating film capable of forming a patterned resin film with high resolution.
• the said solid content means all the components other than the organic solvent (E) mentioned later which can be contained in the composition of this invention.
• Polymer (B) can be produced, for example, by polycondensation. More specifically, when X is an oxygen atom, bisphenol compounds and dihalogen compounds are used as monomers, and alkali metal compounds are used as polymerization catalysts, and when X is a sulfur atom, bisthiol compounds and dihalogen compounds are used as monomers. , and an alkali metal compound as a polymerization catalyst, and when X is an amide bond, it can be produced using a diamine compound, an acid dianhydride, and an acid dichloride as monomers. Examples of the reactive group Y modifier include compounds having one functional group in the molecule that is the same as the functional group that reacts during the polycondensation of the monomer and one or more groups Y. be done.
• the polymer (B11) having the formula (a2) where X is an oxygen atom and the reactive group Y is an ⁇ -methylstyryl group will be described.
• the polymer (B11) has, for example, a phenolic compound (bb1) having two phenolic hydroxyl groups, a halogen compound (bb2) having two halogen atoms, and one phenolic hydroxyl group and one ⁇ -methylstyryl group. It can be obtained by polymerizing at least the reactive group Y modifier (bb3).
• the reactive group Y modifier can be represented by the following formula (YM).
• R Y1 and L Y1 have the same definitions as R Y1 and L Y1 in formula (Y1)
• Z YM is a functional group possessed by the terminal of the main chain or side chain of the polymer (B). It is not particularly limited as long as it is a group capable of reacting with the group.
• examples include an isocyanate group, an acid anhydride group, and a chlorine atom.
• the terminal of the main chain or side chain of B) is a phenolic hydroxyl group
• a chlorine atom can be mentioned
• the terminal of the main chain or side chain of the polymer (B) is a carboxyl group or an acid anhydride group.
• the terminal of the main chain or side chain of the polymer (B) is a chlorinated heteroaromatic ring, may include a hydroxyl group and an amino group.
• the phenol compound (bb1), the halogen compound (bb2), and the reactive group Y modifier (bb3) are polymerized in an appropriate polymerization solvent in the presence of an alkali metal compound.
• the amount of the phenol compound (bb1) to be used is generally less than 100 mol, preferably 90.0 to 99.9 mol, per 100 mol of the halogen compound (bb2).
• the amount of the reactive group Y modifier (bb3) to be used is generally less than 50 mol, preferably 0.1 to 20.0 mol, per 100 mol of the halogen compound (bb2).
• alkali metal compounds include carbonates, hydrogencarbonates and hydroxides of alkali metals such as lithium, sodium and potassium. Among these, carbonates and hydroxides are preferred, and potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide are more preferred.
• the polymer (B) in which X in formula (a2) is other than an oxygen atom can be produced, for example, by known polycondensation.
• the composition of the present invention contains a photopolymerization initiator (C).
• the photopolymerization initiator (C) crosslinks the group Y in the polymer (B) with the polyfunctional maleimide compound (A) by exposure to radiation such as visible light, ultraviolet light, deep ultraviolet light, electron beams, and X-rays. It is a compound that generates an active species that accelerates the reaction.
• the photopolymerization initiator (C) may be used alone or in combination of two or more.
• the exposure treatment of the coating film formed from the composition of the present invention promotes the cross-linking reaction between the group Y in the polymer (B) and the polyfunctional maleimide compound (A), forming a cross-linked structure in the exposed areas. It is considered that the solubility in the developing solution is lowered as a result.
• the photopolymerization initiator (C) is preferably a photosensitive radical polymerization initiator that generates radicals upon irradiation with light.
• Examples include oxime compounds, organic halogenated compounds, oxydiazole compounds, carbonyl compounds, ketal compounds and benzoin compounds , acridine compounds, organic peroxide compounds, azo compounds, coumarin compounds, azide compounds, metallocene compounds, hexaarylbiimidazole compounds, organic boric acid compounds, disulfonic acid compounds, onium salt compounds, acylphosphine (oxide) compounds.
• oxime-based compounds, particularly photoradical polymerization initiators having an oxime ester structure are preferred from the viewpoint of sensitivity.
• a photoradical polymerization initiator having an oxime ester structure may have geometric isomers resulting from the double bond of the oxime, but these are not distinguished, and both are included in the photoradical polymerization initiator (C).
• photoradical polymerization initiators having an oxime ester structure include, for example, WO2010/146883, JP-A-2011-132215, JP-A-2008-506749, JP-A-2009-519904, and JP-A-2009- Photoradical polymerization initiators described in JP-A-519991 can be mentioned.
• radical photopolymerization initiators having an oxime ester structure include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine and N-ethoxycarbonyloxy-1-phenylpropane.
• photopolymerization initiators (C) may be used singly or in combination of two or more.
• the lower limit of the content of the photopolymerization initiator (C) with respect to 100 parts by mass of the polymer (B) in the composition of the present invention is usually 0.01 parts by mass, preferably 0.1 parts by mass, more preferably 0.1 part by mass. 5 parts by mass; the upper limit is usually 30 parts by mass, preferably 20 parts by mass, more preferably 10 parts by mass.
• the content of the photopolymerization initiator (C) is at least the above lower limit, the exposed portions are sufficiently cured, and the heat resistance of the patterned resin film is likely to be improved.
• the content of the photopolymerization initiator (C) is equal to or less than the upper limit, a patterned resin film with high resolution can be easily obtained without lowering the transparency to the light used for exposure.
• the composition of the present invention may contain a surfactant (D) from the viewpoint of improving coatability, defoaming properties, leveling properties and the like.
• the surfactant is not particularly limited, and known nonionic surfactants, fluorosurfactants and silicone surfactants can be used.
• Examples of commercially available surfactants include BM-1000, BM-1100 (manufactured by BM Chemie), Megafac F142D, F172, F173 and F183 (manufactured by Dainippon Ink and Chemicals Co., Ltd.), Florard FC- 135, FC-170C, FC-430, FC-431 (manufactured by Sumitomo 3M), Surflon S-112, S-113, S-131, S-141, S-145 ( Asahi Glass Co., Ltd.), SH-28PA, -190, -193, SZ-6032, SF-8428 (manufactured by Toray Silicone Co., Ltd.), NBX-15 (manufactured by Neos Co., Ltd.), etc.
• Fluorine-based surfactants KL-245, KL-270 (manufactured by Kyoeisha Chemical Co., Ltd.), SH28PA (manufactured by Dow Corning Toray), etc. Silicone-based surfactants commercially available; Nonion S -6, Nonion 0-4, Pronon 201, Pronon 204 (manufactured by NOF Corporation), Emulgen A-60, A-90, A-500 (manufactured by Kao Corporation), KL-600 (Kyoeisha Chemical (manufactured by Co., Ltd.) and the like are commercially available nonionic surfactants.
• the surfactant (D) may be used alone or in combination of two or more. Surfactant (D) is preferably used in an amount of 5 parts by mass or less, more preferably in the range of 0.01 to 2 parts by mass, based on 100 parts by mass of polymer (B).
• the composition of the invention may contain an organic solvent (E).
• organic solvent (E) By using the organic solvent (E), the handleability of the composition of the present invention can be improved, and the viscosity and storage stability can be adjusted.
• the organic solvent (E) is not particularly limited as long as it is an organic solvent capable of dissolving or dispersing each component such as the polyfunctional maleimide compound (A), the polymer (B) and the photopolymerization initiator (C).
• Examples of the organic solvent (E) include ketone solvents, alcohol solvents, ether solvents, ester solvents, amide solvents, and hydrocarbon solvents.
• Ketone solvents include, for example, acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, diethyl ketone, methyl-iso-butyl ketone, 2-heptanone (methyl amyl ketone), ethyl-n-butyl ketone, methyl- chain ketone solvents such as n-hexyl ketone, di-iso-butyl ketone and trimethylnonanone; cyclic ketone solvents such as cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone and methylcyclohexanone; 2,4-pentanedione, Acetonylacetone, acetophenone.
• alcohol solvents examples include aliphatic monoalcohol solvents having 1 to 18 carbon atoms such as 4-methyl-2-pentanol and n-hexanol; alicyclic monoalcohol solvents having 3 to 18 carbon atoms such as cyclohexanol; Polyhydric alcohol solvents having 2 to 18 carbon atoms such as 1,2-propylene glycol; and polyhydric alcohol partial ether solvents having 3 to 19 carbon atoms such as propylene glycol monomethyl ether.
• ether solvents include dialkyl ether solvents such as diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, diisoamyl ether, dihexyl ether and diheptyl ether; cyclic ether solvents such as tetrahydrofuran and tetrahydropyran; diphenyl ether, anisole and the like. aromatic ring-containing ether solvents.
• dialkyl ether solvents such as diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, diisoamyl ether, dihexyl ether and diheptyl ether
• cyclic ether solvents such as tetrahydrofuran and tetrahydropyran
• diphenyl ether anisole and the like.
• aromatic ring-containing ether solvents aromatic ring-containing ether solvents.
• ester solvents include monocarboxylic acid ester solvents such as n-butyl acetate and ethyl lactate; polyhydric alcohol carboxylate solvents such as propylene glycol acetate; polyhydric alcohol partial ether carboxylate solvents such as propylene glycol monomethyl ether acetate; Polyvalent carboxylic acid diester solvents such as diethyl oxalate; lactone solvents such as ⁇ -butyrolactone and ⁇ -valerolactone; and carbonate solvents such as dimethyl carbonate, diethyl carbonate, ethylene carbonate and propylene carbonate.
• monocarboxylic acid ester solvents such as n-butyl acetate and ethyl lactate
• polyhydric alcohol carboxylate solvents such as propylene glycol acetate
• polyhydric alcohol partial ether carboxylate solvents such as propylene glycol monomethyl ether acetate
• Polyvalent carboxylic acid diester solvents such as dieth
• amide solvents include cyclic amide solvents such as N,N'-dimethylimidazolidinone and N-methyl-2-pyrrolidone; N-methylformamide, N,N-dimethylformamide, N,N-diethylformamide, and acetamide. , N-methylacetamide, N,N-dimethylacetamide, and N-methylpropionamide.
• hydrocarbon solvents examples include aliphatic hydrocarbon solvents having 5 to 12 carbon atoms such as n-pentane and n-hexane; aromatic hydrocarbon solvents having 6 to 16 carbon atoms such as toluene and xylene.
• the organic solvent (E) is preferably at least one selected from ketone solvents, ester solvents and amide solvents.
• the composition of the present invention can contain one or more organic solvents (E).
• the content of the organic solvent (E) in the composition of the present invention is such that the solid content concentration in the composition is usually 10 to 50% by mass.
• composition of the present invention may contain other components as long as the objects and characteristics of the present invention are not impaired.
• Other components include, for example, a cross-linking agent other than the polyfunctional maleimide compound (A); a polymer other than the polymer (B); Additives such as fillers and quenchers are included.
• the composition of the present invention can be produced by uniformly mixing each component constituting the composition of the present invention. Moreover, in order to remove foreign matter, after uniformly mixing the respective components, the obtained mixture can be filtered with a filter or the like.
• a patterned resin film obtained by curing the composition of the present invention has excellent elongation. This is presumed for the following reasons. Since the polymer (B) has the reactive groups substantially only at the ends of the polymer chains, when the composition of the present invention is subjected to cross-linking treatment, cross-linking occurs so that the polymer chains in the polymer (B) are chain-extended. Therefore, the cross-linking density is low, and on the other hand, it is thought that the polymer chains are entangled with each other to a large extent, resulting in loose interaction between the polymer chains. Therefore, it is presumed that the extensibility of the obtained patterned resin film was improved.
• the patterned resin film obtained from the composition of the present invention has a low dielectric constant and a low dielectric loss tangent.
• the dipole moment in the minor axis direction (perpendicular to the main chain direction of the polymer) in the repeating structural unit of the polymer used is small.
• cross-linking mainly occurs at the polymer chain terminal, not in the repeating structural unit (a2) of the polymer (B), so it is speculated that the change in the dipole moment is small throughout the formation of the patterned resin film. be done.
• a coating film made of the composition of the present invention can be developed with a developer containing an organic solvent, as described later.
• a hygroscopic and highly polar functional group such as a phenolic hydroxyl group is introduced into the repeating structural unit of the polymer in order to impart alkaline developability to the polymer.
• the introduction amount of the highly polar functional group in the polymer is large, and it is considered that the dielectric constant and the dielectric loss tangent are high for this reason.
• the introduction amount of the highly polar functional group to the polymer can be reduced, and thus the dielectric constant is low. , and a low dielectric loss tangent can be achieved.
• the method of the present invention for producing a resin film having a pattern comprises a step (1) of forming a coating film of the composition of the present invention on a substrate, and selectively exposing the coating film to light. A step (2) and a step (3) of developing the exposed coating film with a developer containing an organic solvent.
• step (1) the composition of the present invention is generally applied onto a substrate so that the thickness of the finally obtained patterned resin film is, for example, 0.1 to 100 ⁇ m.
• the substrate is heated using an oven or a hot plate, usually at 50 to 140° C. for 10 to 360 seconds.
• a coating film of the composition of the present invention is formed on the substrate.
• substrates include silicon wafers, compound semiconductor wafers, wafers with metal thin films, glass substrates, quartz substrates, ceramic substrates, aluminum substrates, and substrates having semiconductor chips on the surface of these substrates.
• coating methods include dipping, spraying, bar coating, roll coating, spin coating, curtain coating, gravure printing, silk screen, and inkjet.
• step (2) the coating film is selectively exposed using, for example, a contact aligner, stepper or scanner.
• a contact aligner for example, a contact aligner, stepper or scanner.
• selective specifically means through a photomask on which a predetermined mask pattern is formed.
• the exposure light examples include ultraviolet light, visible light, and the like, and usually light with a wavelength of 200 to 500 nm (eg, i-line (365 nm)) is used.
• the exposure dose varies depending on the type of each component in the composition of the present invention, the mixing ratio, the thickness of the coating film, etc., but the exposure dose is usually 100 to 1500 mJ/cm 2 .
• heat treatment post-exposure baking
• the conditions for the heat treatment after exposure vary depending on the content of each component in the composition of the present invention and the thickness of the coating film, but are usually 70 to 250° C., preferably 80 to 200° C., for 1 to 60 minutes. degree.
• a desired patterned resin film is formed on the substrate by developing the exposed coating film with a developer containing an organic solvent to dissolve and remove the non-exposed areas.
• the developing method includes, for example, a shower developing method, a spray developing method, an immersion developing method, and a puddle developing method.
• the developing conditions are usually 20 to 40° C. for 1 to 10 minutes.
• the developer contains one or more organic solvents.
• the developer include organic solvents such as ketone solvents, alcohol solvents, ether solvents, ester solvents, amide solvents, and hydrocarbon solvents, and liquids containing such organic solvents.
• organic solvents include the compounds exemplified as the organic solvent (E).
• E organic solvent
• at least one solvent selected from ketone solvents, ester solvents and amide solvents is preferred.
• Components other than the organic solvent in the developer include, for example, water, silicon oil and surfactants.
• the content of the organic solvent in the developer is preferably 80% by mass or more, more preferably 90% by mass or more, still more preferably 95% by mass or more, and particularly preferably 99% by mass or more.
• the patterned resin film After forming a patterned resin film by developing the exposed coating film using a developer containing an organic solvent, the patterned resin film can be washed with water or the like and dried.
• the shape of the pattern in the patterned resin film is not particularly limited as long as it has a concave-convex structure, and examples thereof include a line and space pattern, dot pattern, hole pattern, and grid pattern.
• Step (4)> In the method for producing a patterned resin film of the present invention, after the step (3), the patterned resin film is sufficiently removed by heat treatment (post-baking) as necessary in order to sufficiently develop the properties as an insulating film. It can have a step (4) of curing.
• the curing conditions are not particularly limited, but depending on the application of the patterned resin film, for example, the patterned resin film is heated at a temperature of 100 to 250° C. for about 30 minutes to 10 hours.
• the patterned resin film obtained by the manufacturing method of the present invention can be suitably used as an insulating film (eg, surface protective film, interlayer insulating film, flattening film) possessed by a semiconductor circuit board.
• an insulating film eg, surface protective film, interlayer insulating film, flattening film
• a semiconductor circuit board including the resin film having the pattern (patterned resin film) can be produced.
• the semiconductor circuit board has a patterned resin film formed from the composition of the present invention described above, preferably a patterned insulating film such as a surface protective film, an interlayer insulating film, and a planarizing film, so that it can be used as a high-frequency circuit board. Useful.
• Table 1 below shows the types and amounts of the monomers used in Synthesis Examples 1 to 8, and the weight average molecular weights (Mw) of the obtained polymers.
• Table 2 shows the polyfunctional maleimide compound, polyfunctional styryl compound, polymer, photopolymerization initiator and other components shown in Tables 2-1 to 2-3 below (hereinafter collectively referred to as "Table 2").
• the organic solvent shown in Table 2 was used in the amount and mixed uniformly so that the solid content concentration shown in Table 2 was obtained, and the radiation-sensitive compositions of Examples 1 to 16 and Comparative Examples 1 to 5 were produced. .
• the obtained radiation-sensitive composition was evaluated as follows. Table 2 shows the results.
• a 6-inch silicon wafer was spin-coated with the radiation-sensitive composition, and then heated at 110° C. for 5 minutes using a hot plate to prepare a coating film (thickness: 10 ⁇ m). Then, using an aligner (manufactured by Suss Microtec, model "MA-150"), the coating film is exposed to ultraviolet rays from a high-pressure mercury lamp through a photomask so that the exposure amount at a wavelength of 365 nm is 500 mJ/cm 2 . did. Subsequently, immersion development was performed at 23° C. for 3 minutes using a developer (cyclopentanone).
• the developed coating film was heated in an oven under nitrogen atmosphere under the heating conditions (curing temperature, curing time) shown in Table 2 to produce a patterned resin film.
• the produced resin film having a pattern was observed with an electron microscope and evaluated according to the following criteria. ⁇ : A square pattern of 50 ⁇ m in length and 50 ⁇ m in width was formed. x: A square pattern with a length of 50 ⁇ m and a width of 50 ⁇ m cannot be formed.
• the radiation-sensitive composition was applied onto a substrate with a release agent, and then heated at 110° C. for 5 minutes using an oven to prepare a coating film.
• an aligner manufactured by Suss Microtec, model "MA-150"
• the entire surface of the coating film was irradiated with ultraviolet rays from a high-pressure mercury lamp so that the exposure amount at a wavelength of 365 nm was 500 mJ/cm 2 .
• heating was performed under the heating conditions (curing temperature, curing time) shown in Table 2 under a nitrogen atmosphere.
• the post-baking coating film was peeled off from the release material-attached substrate to obtain a resin film having a thickness of 15 ⁇ m.
• the resulting resin film was cut into strips measuring 5 cm long and 0.5 cm wide.
• the tensile elongation at break (%) of the strip-shaped resin film was measured with a tensile compression tester (product name “SDWS-0201 type”, manufactured by Imada Seisakusho Co., Ltd.).
• the average value of five measurements was defined as "elongation (initial value)" and evaluated according to the following criteria.
• Elongation is 10% or more
• ⁇ Elongation is less than 10% or cannot be measured
• the tensile test piece prepared above was subjected to three times of reflow in air (maximum temperature 260°C), and then exposed to an environment of 130°C/85% RH/96 hours.
• the tensile elongation of the test piece after exposure was measured in the same manner as the elongation (initial value) and was defined as "elongation (after PCT test)".
• the radiation-sensitive composition was applied onto a substrate with a release agent, and then heated at 110° C. for 5 minutes using an oven to prepare a coating film.
• an aligner manufactured by Suss Microtec, model "MA-150"
• the entire surface of the coating film was irradiated with ultraviolet rays from a high-pressure mercury lamp so that the exposure amount at a wavelength of 365 nm was 500 mJ/cm 2 .
• heating was performed under the heating conditions (curing temperature, curing time) shown in Table 2 under a nitrogen atmosphere.
• the post-baking coating film was peeled off from the release material-attached substrate to obtain a resin film having a thickness of 10 ⁇ m.
• the relative permittivity ( ⁇ r ) and dielectric loss tangent (tan ⁇ ) of the obtained resin film at 10 GHz were measured under the conditions of 23° C. and relative humidity of 50% RH with a dielectric property measuring device (10 GHz cavity manufactured by Kanto Denshi Applied Development Co., Ltd.). resonator), and measured by the cavity resonator perturbation method.
• A1-1) a polyfunctional maleimide compound represented by the following formula (A1-1) (“BMI-2000” manufactured by Daiwa Kasei Kogyo Co., Ltd.)
• A1-2 a polyfunctional maleimide compound represented by the following formula (A1-2) (“BMI-2300” manufactured by Daiwa Kasei Kogyo Co., Ltd.)
• A1-3 a polyfunctional maleimide compound represented by the following formula (A1-3) (“BMI-4000” manufactured by Daiwa Kasei Kogyo Co., Ltd.)
• A1-4 a polyfunctional maleimide compound represented by the following formula (A1-4) (“MIR-3000” manufactured by Nippon Kayaku Co., Ltd.)
• C1 "Irgacure OXE02" manufactured by BASF Corporation
• D1 fluorine-based surfactant (“NBX-15” manufactured by Neos Co., Ltd.)
• E1 cyclohexanone
• E2 gamma butyrolactone

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