WO2023276517A1 - Composition de résine, produit durci, procédé de production de produit durci, composant électronique, dispositif d'affichage et dispositif à semi-conducteur - Google Patents

Composition de résine, produit durci, procédé de production de produit durci, composant électronique, dispositif d'affichage et dispositif à semi-conducteur Download PDF

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Publication number
WO2023276517A1
WO2023276517A1 PCT/JP2022/021888 JP2022021888W WO2023276517A1 WO 2023276517 A1 WO2023276517 A1 WO 2023276517A1 JP 2022021888 W JP2022021888 W JP 2022021888W WO 2023276517 A1 WO2023276517 A1 WO 2023276517A1
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formula
resin composition
group
cured product
carbon atoms
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PCT/JP2022/021888
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English (en)
Japanese (ja)
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荘司優
小笠原央
荒木斉
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東レ株式会社
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Priority to JP2022535492A priority Critical patent/JPWO2023276517A1/ja
Priority to KR1020237037759A priority patent/KR20240028331A/ko
Publication of WO2023276517A1 publication Critical patent/WO2023276517A1/fr

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    • 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
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G73/22—Polybenzoxazoles
    • 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/011—Crosslinking or vulcanising agents, e.g. accelerators
    • 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
    • C08K5/13—Phenols; Phenolates
    • 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
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/22—Exposing sequentially with the same light pattern different positions of the same surface
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Definitions

  • the present invention relates to a resin composition, a cured product, a method for producing a cured product, an electronic component, a display device, and a semiconductor device.
  • polyimide resins and polybenzoxazole resins which are excellent in heat resistance and elongation at break, have been widely used for surface protective films and interlayer insulating films of semiconductor devices.
  • polyimide and polybenzoxazole are obtained by thermally dehydrating and ring-closing a coating film of these precursors to obtain a thin film having excellent heat resistance and elongation at break. In that case, high-temperature firing at around 350° C. is usually required.
  • MRAM Magneticoresistive Random Access Memory
  • the film after heat curing remains as a permanent film inside the device, so the physical properties of the cured product, especially the elongation, are very important. Also, when used as an insulating film between wiring layers in a wafer level package, it is necessary that no cracks or peeling occur in a reliability test such as a thermal cycle test.
  • Patent Document 1 a method using a polybenzoxazole precursor having an aliphatic group (Patent Document 1) or a photosensitive resin composition containing a novolac resin having a crosslinkable group has been proposed (Patent Document 2).
  • the polybenzoxazole precursor having an aliphatic group described in Patent Document 1 and the cured product of the photosensitive resin composition containing the novolac resin described in Patent Document 2 are included in the cured product after the thermal cycle test.
  • the resin deteriorates and cracks occur after the reliability test.
  • the novolak resin described in Patent Document 2 has a low breaking elongation when cured, cracks are likely to occur after a thermal cycle test.
  • the present invention relates to the following. That is, the resin composition of the present invention is a resin composition containing (A) a resin represented by formula (1) and (B) a resin represented by formula (2).
  • each X independently represents a repeating structural unit of polyamide, polyimide, polybenzoxazole or a precursor thereof, and R 1 is a monovalent represented by formula (3) or formula (4). is the base.
  • R a represents a group selected from the group consisting of R 1 , a hydrogen atom, and a monovalent organic group having 1 to 20 carbon atoms.
  • n 1 is an integer from 2 to 200;
  • each Y independently represents a repeating structural unit of polyamide, polyimide, polybenzoxazole, or a precursor thereof, and R2 is a monovalent group represented by formula (5).
  • R b represents a group selected from the group consisting of R 2 , a hydrogen atom and a monovalent organic group having 1 to 20 carbon atoms.
  • n2 is an integer from 2 to 200;
  • R 3 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms. * represents a joint.
  • the resin composition of the present invention comprises (A) a resin represented by formula (1) (hereinafter sometimes referred to as component (A) or (A) resin) and (B) represented by formula (2). containing a resin (hereinafter sometimes referred to as (B) component or (B) resin).
  • each X independently represents a repeating structural unit of polyamide, polyimide, polybenzoxazole or a precursor thereof, and R 1 is a monovalent represented by formula (3) or formula (4). is the base.
  • R a represents a group selected from the group consisting of R 1 , a hydrogen atom, and a monovalent organic group having 1 to 20 carbon atoms.
  • n 1 is an integer from 2 to 200;
  • each Y independently represents a repeating structural unit of polyamide, polyimide, polybenzoxazole, or a precursor thereof, and R2 is a monovalent group represented by formula (5).
  • R b represents a group selected from the group consisting of R 2 , a hydrogen atom and a monovalent organic group having 1 to 20 carbon atoms.
  • n2 is an integer from 2 to 200;
  • R 3 is a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms. * represents a joint.
  • the terminal of component (A) reacts with the terminal of component (B) in low-temperature curing at 250° C. or less, resulting in a cured product. Since the molecular weight of the resin inside can be increased, the elongation at break and the crack resistance after the thermal cycle test are improved.
  • X in component (A) and Y in component (B) are each independently repeating structural units of polyamide, polyimide, polybenzoxazole, or precursors thereof.
  • Polyimide is not particularly limited as long as it has an imide ring.
  • the polyimide precursor is not particularly limited as long as it has a structure that becomes a polyimide having an imide ring upon dehydration and ring closure, and may contain polyamic acid, polyamic acid ester, or the like.
  • the polyamide is not particularly limited as long as it has an amide bond.
  • Polybenzoxazole is not particularly limited as long as it has a benzoxazole ring.
  • the polybenzoxazole precursor is not particularly limited as long as it has a structure that becomes polybenzoxazole having a benzoxazole ring upon dehydration and ring closure, and may contain polyhydroxyamide or the like.
  • Components (A) and (B) are used because they can easily provide excellent properties as surface protective films for semiconductor devices, interlayer insulating films, insulating layers for display devices such as organic light-emitting devices, and flattening films for TFT substrates. It is preferable that the amount of outgas at a high temperature of 160° C. or higher after heat treatment is small.
  • component (A) and component (B) preferably contain at least one selected from the group consisting of polyamide, polyimide, polybenzoxazole, precursors thereof, and copolymers thereof.
  • the components (A) and (B) can be obtained, for example, by polycondensing dicarboxylic acids, dicarboxylic acid derivatives, acid dianhydrides, diamines, acid anhydrides, monoamines, and the like.
  • dicarboxylic acid derivatives include, but are not limited to, dicarboxylic acid dichlorides, active amide compounds such as hydroxybenzotriazole and imidazole.
  • R 1 in component (A) and R 2 in component (B) contain monoamines, acid anhydrides, monocarboxylic acids, monocarboxylic acid chloride compounds, monoactive ester compounds, etc. as main chain end caps. Obtained by condensation.
  • R 1 in component (A) and R 2 in component (B) are at least one hydrogen atom selected from maleimide, maleic acid monoalkyl ester, 2-aminostyrene, 3-aminostyrene, 4-aminostyrene, etc. , a structure in which the OH or amino group of the carboxyl group is removed (hereinafter sometimes referred to as "residue").
  • R a in components (A) and (B) represents a group selected from the group consisting of R 1 , a hydrogen atom, and an organic group having 1 to 20 carbon atoms
  • R b represents R 2 , a hydrogen atom.
  • organic groups having 1 to 20 carbon atoms include aniline, 2-ethynylaniline, 3-ethynylaniline, 4-ethynylaniline, 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1- Hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-amino naphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy -5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 2-
  • the repeating structural unit of the polyimide is a repeating structural unit represented by formula (6)
  • the repeating structural unit of the polyamide, polyimide precursor or polybenzoxazole precursor is a repeating structural unit represented by formula (7)
  • the repeating structural unit of the polybenzoxazole is represented by formula (8). is preferably a repeating structural unit.
  • R 4 represents a tetravalent organic group having 4 to 40 carbon atoms.
  • R 5 represents a divalent organic group having 4 to 40 carbon atoms.
  • R 6 represents a divalent to octavalent organic group having 4 to 40 carbon atoms.
  • R 7 represents a divalent to tetravalent organic group having 4 to 40 carbon atoms.
  • R 8 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
  • q and r are in the range of 0 ⁇ q ⁇ 4, 0 ⁇ r ⁇ 4 and represent integers satisfying 0 ⁇ q+r ⁇ 6.
  • s represents an integer from 0 to 2;
  • R 9 represents a divalent organic group having 4 to 40 carbon atoms.
  • R 10 represents a divalent organic group having 4 to 40 carbon atoms.
  • R 4 represents a tetravalent organic group having 4 to 40 carbon atoms.
  • examples of the tetravalent organic group having 4 to 40 carbon atoms include residues of aromatic tetracarboxylic acids and aliphatic tetracarboxylic acids.
  • the aliphatic tetracarboxylic acid residue is preferably an alicyclic tetracarboxylic acid residue.
  • residue of the aromatic tetracarboxylic acid include pyromellitic acid, 3,3′,4,4′-biphenyltetracarboxylic acid, 2,3,3′,4′-biphenyltetracarboxylic acid, 2 ,2′,3,3′-biphenyltetracarboxylic acid, 3,3′,4,4′-diphenylethertetracarboxylic acid, 3,3′,4,4′-benzophenonetetracarboxylic acid, 2,2′,3 ,3′-benzophenonetetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)propane, 2,2-bis(2,3-dicarboxyphenyl)propane, 1,1-bis(3,4 -dicarboxyphenyl)ethane, 1,1-bis(2,3-dicarboxyphenyl)ethane, bis(3,4-dicarboxyphenyl)methane
  • residue of the aliphatic tetracarboxylic acid include residues of cyclobutanetetracarboxylic acid and 1,2,3,4-cyclopentanetetracarboxylic acid.
  • pyromellitic acid, 3,3′,4,4′-biphenyltetracarboxylic acid, 3,3′,4,4′-diphenylethertetracarboxylic acid, 2,2-bis(3,4-di carboxyphenyl) is the residue of hexafluoropropane. Two or more types of these residues may be included.
  • R 6 represents a divalent to octavalent organic group having 4 to 40 carbon atoms
  • R 10 represents a divalent organic group having 4 to 40 carbon atoms in formula (8).
  • divalent to octavalent organic groups having 4 to 40 carbon atoms include residues of aromatic dicarboxylic acids, aromatic tricarboxylic acids, aromatic tetracarboxylic acids, aliphatic dicarboxylic acids, aliphatic tetracarboxylic acids, and the like. be done.
  • aromatic dicarboxylic acid residue examples include residues of terephthalic acid, isophthalic acid, diphenyletherdicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyldicarboxylic acid, benzophenonedicarboxylic acid, triphenyldicarboxylic acid, and the like. be done.
  • aromatic tricarboxylic acid residue examples include residues of trimellitic acid, trimesic acid, diphenylethertricarboxylic acid, biphenyltricarboxylic acid, and the like.
  • aromatic tetracarboxylic acid residue examples include pyromellitic acid, 3,3′,4,4′-biphenyltetracarboxylic acid, 2,3,3′,4′-biphenyltetracarboxylic acid, 2, 2′,3,3′-biphenyltetracarboxylic acid, 3,3′,4,4′-diphenylethertetracarboxylic acid, 3,3′,4,4′-benzophenonetetracarboxylic acid, 2,2′,3, 3′-benzophenonetetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)propane, 2,2-bis(2,3-dicarboxyphenyl)propane, 1,1-bis(3,4- dicarboxyphenyl)ethane, 1,1-bis(2,3-dicarboxyphenyl)ethane, bis(3,4-dicarboxyphenyl)methane, bis(2,3-dicar
  • residues of aliphatic dicarboxylic acids include residues of adipic acid, sebacic acid, dodecanedioic acid, 1,4-cyclohexanedicarboxylic acid, and the like.
  • aliphatic tetracarboxylic acids include residues of cyclobutanetetracarboxylic acid and 1,2,3,4-cyclopentanetetracarboxylic acid.
  • R6 and R10 may contain two or more of these residues.
  • R 8 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, such as a hydrocarbon group, a fluoroalkyl group, a phenyl group and a substituted phenyl group.
  • Substituents of the substituted phenyl group include hydrocarbon groups, fluoroalkyl groups, phenyl groups, nitro groups, cyano groups, carboxyl groups, hydroxyl groups, amino groups, sulfonic acid groups and the like.
  • R 5 in formula (6), R 7 in formula (7), and R 9 in formula (8) contain structures derived from diamine residues.
  • the diamine residue include 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, 3,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, 1,4-bis( 4-aminophenoxy)benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxy)biphenyl, bis ⁇ 4-(4-amino phenoxy)phenyl ⁇ ether, 1,4-bis(4-aminophenoxy)benzene, 2,2'-dimethyl-4,4'-diaminobiphenyl, 2,2'-diethyl-4,4'-dia
  • R 4 in formula (6) and R 6 in formula (7) are structures represented by formula (9), and R 5 in formula (6) and R 7 in formula (7) are It preferably has a structure represented by formula (10).
  • R 11 represents a single bond, —O—, —C(CF 3 ) 2 —, or a structure represented by formula (11). * represents a joint.
  • R 12 is a single bond, —O—, —C(CH 3 ) 2 — or —C(CF 3 ) 2 —, and each R 13 is independently a hydrogen atom or a represents a monovalent organic group of ⁇ 20.
  • R 14 represents a structure represented by a single bond, —O—, —C(CH 3 ) 2 — or —C(CF 3 ) 2 —. * represents a joint.
  • the resin composition contains (A) component and (B) component having the structural units of the formula (9) and the formula (10) in the formula (6) or (7). High breaking elongation and high crack resistance can be easily obtained in cured products.
  • R 9 in formula (8) is a structure represented by a single bond, a divalent hydrocarbon group having 1 to 6 carbon atoms, or a fluoroalkylene group having 1 to 6 carbon atoms
  • R 10 is represented by formula (12 ) preferably has a structure represented by
  • R 15 represents a structure represented by a single bond, —O—, —C(CH 3 ) 2 — or —C(CF 3 ) 2 —. * represents a chemical bond.
  • R 1 and R 2 in the resin composition of the present invention have properties as an electron donor and an electron acceptor, respectively, and tend to form a charge transfer complex with each other. Therefore, the coexistence of R 1 and R 2 significantly improves the reactivity between the terminal groups compared to the presence of R 1 or R 2 alone.
  • M When M is within the above range, it becomes easier to form a charge transfer complex of R 1 and R 2 , and the reactivity between the terminal groups is significantly improved, so that the cured product has high elongation at break and high crack resistance. can get things.
  • M 0.25 or more and 4 or less, a cured product having sufficient mechanical strength can be obtained, and the cured product has high breaking elongation and high crack resistance.
  • the ratio M of the substance amount of terminal group R 1 of component (A) to the substance amount of terminal R 2 of component (B) can be determined by nuclear magnetic resonance (1H-NMR, 13C-NMR), infrared absorption spectroscopy (IR method), matrix-assisted laser desorption ionization method-time-of-flight mass spectrometry (MALDI-TOFMS) in a resin composition in which the molecular structures of components (A) and (B) have been identified, 1H-NMR. use.
  • the signal originating from the R 1 hydrogen atom appears at 5 to 6 ppm and the signal originating from the R 2 hydrogen atom appears at 6 to 6.5 ppm.
  • the total integrated value of the signal derived from the hydrogen atom of the amide bond appearing at 9 to 11 ppm is 100
  • the total integrated value of the signal derived from the hydrogen atom of the terminal group R 1 of the component (A) is r 1
  • the component (B) The total integral value of the signal derived from the hydrogen atom of the terminal group R 2 of is r 2
  • the weight average molecular weight of the resin composition of the present invention is preferably 5,000 or more and 35,000 or less.
  • a weight-average molecular weight of 5,000 or more in terms of polystyrene by GPC (gel permeation chromatography) is preferable because cracks do not occur in the film-forming process before curing, and 10,000 or more is more preferable.
  • the weight average molecular weight is more preferably 30,000 or less, even more preferably 25,000 or less.
  • the weight average molecular weight (Mw) can be confirmed using GPC (gel permeation chromatography).
  • NMP N-methyl-2-pyrrolidone
  • NMP is measured as a developing solvent and can be obtained in terms of polystyrene.
  • the resin composition of the present invention may contain a photoacid generator. Photosensitivity can be imparted to the resin composition by containing a photoacid generator.
  • the photoacid generator generates acid in the light-irradiated portion of the resin composition. As a result, the solubility of the light-irradiated portion in an alkaline developer increases, so that a positive pattern in which the light-irradiated portion dissolves can be obtained.
  • the photoacid generators mentioned above include quinonediazide compounds, sulfonium salts, phosphonium salts, diazonium salts, iodonium salts, and the like.
  • the resin composition of the present invention can further contain a sensitizer and the like, if necessary.
  • quinonediazide compound a compound in which a sulfonic acid of naphthoquinonediazide is ester-bonded to a compound having a phenolic hydroxyl group is preferable.
  • Compounds having a phenolic hydroxyl group include Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, TrisP-SA, TrisOCR-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP -IPZ, BisOCP-IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, methylenetris-FR-CR, BisRS-26X, DML-MBPC, DMLMBOC, DML-OCHP, DML-PCHP, DML- PC, DML-PTBP, DML-34X, DML-EP, DML-POP, Dimethylol-BisOC-P, DML-PFP, DML-PSBP, DML-MTrisPC, TriML-P, TriML-35XL, TML-BP, TML- HQ, TML-pp-BPF, TML-BPA, TMOM-BP, HML-TP
  • Sulfonic acids of naphthoquinonediazide include 4-naphthoquinonediazide sulfonic acid and 5-naphthoquinonediazide sulfonic acid.
  • the affinity of the quinonediazide compound for an alkaline aqueous solution is lowered.
  • the solubility of the resin composition in the unexposed area in an alkaline aqueous solution is greatly reduced.
  • the quinonediazide sulfonyl group is converted to indenecarboxylic acid by exposure, and a high dissolution rate in an alkaline aqueous solution of the resin composition having photosensitivity in the exposed area can be obtained. That is, as a result, the dissolution rate ratio between the exposed area and the unexposed area of the composition can be increased, and a pattern with high resolution can be obtained.
  • a resin composition having positive-type photosensitivity that is sensitive to the i-line (365 nm), h-line (405 nm), g-line (436 nm) of a general mercury lamp and broadband including them. can get things.
  • the photoacid generator may be contained alone or in combination of two or more, and a resin composition having high sensitivity and photosensitivity can be obtained.
  • both a 5-naphthoquinonediazidesulfonyl group and a 4-naphthoquinonediazidesulfonyl group are preferably used.
  • a 5-naphthoquinonediazide sulfonyl ester compound has absorption extending to the g-line region of a mercury lamp, and is suitable for g-line exposure and full-wavelength exposure.
  • a 4-naphthoquinonediazide sulfonyl ester compound has absorption in the i-line region of a mercury lamp and is suitable for i-line exposure. It is preferable to select a 4-naphthoquinonediazide sulfonyl ester compound or a 5-naphthoquinone diazidesulfonyl ester compound depending on the wavelength of exposure.
  • a naphthoquinonediazidesulfonyl ester compound containing a 4-naphthoquinonediazidesulfonyl group and a 5-naphthoquinonediazidesulfonyl group in the same molecule can also be used in combination.
  • a quinonediazide compound can be synthesized by a known method through an esterification reaction between a compound having a phenolic hydroxyl group and a quinonediazide sulfonic acid compound. By using a quinonediazide compound, the resolution, sensitivity, and film retention rate are further improved.
  • sulfonium salts phosphonium salts and diazonium salts are preferable because they moderately stabilize the acid component generated by exposure. Among them, sulfonium salts are preferred.
  • the content of the photoacid generator is preferably 0.1 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass as the total amount of the components (A) and (B).
  • the content of the photoacid generator is 0.1 parts by mass or more and 100 parts by mass or less, photosensitivity can be imparted while maintaining the heat resistance, chemical resistance, and breaking elongation of the film after heat treatment. .
  • the content of the photoacid generator is more preferably 1 part by mass or more, and 3 parts by mass, relative to 100 parts by mass of the total amount of components (A) and (B).
  • the above is more preferable.
  • 100 mass parts or less are more preferable, and 80 mass parts or less are still more preferable.
  • the amount is 1 part by mass or more and 100 parts by mass or less, photosensitivity can be imparted while maintaining the heat resistance, chemical resistance and breaking elongation of the film after heat treatment.
  • the content of the photoacid generator is 0.1 parts by mass with respect to 100 parts by mass of the total amount of components (A) and (B).
  • the above is more preferable, 1 part by mass or more is more preferable, and 3 parts by mass or more is particularly preferable.
  • it is more preferably 100 parts by mass or less, even more preferably 80 parts by mass or less, and particularly preferably 50 parts by mass or less.
  • the amount is 0.1 parts by mass or more and 100 parts by mass or less, photosensitivity can be imparted while maintaining the heat resistance, chemical resistance and breaking elongation of the film after heat treatment.
  • the resin composition of the present invention preferably contains a photopolymerization initiator and a photopolymerizable compound.
  • the photopolymerization initiator and photopolymerizable compound polymerize in the light-irradiated portion of the resin composition and become insoluble in the developer. As a result, the solubility in the developing solution of the light-irradiated portion is drastically reduced, so that a negative pattern in which the light-unirradiated portion dissolves can be obtained.
  • Benzophenones such as benzophenone, Michler's ketone, 4,4'-bis(diethylamino)benzophenone, and 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone.
  • benzylidenes such as 3,5-bis(diethylaminobenzylidene)-N-methyl-4-piperidone and 3,5-bis(diethylaminobenzylidene)-N-ethyl-4-piperidone; 7-diethylamino-3-thenonylcoumarin, 4,6-dimethyl-3-ethylaminocoumarin, 3,3-carbonylbis(7-diethylaminocoumarin), 7-diethylamino-3-(1-methylbenzimidazolyl)coumarin, 3 - Coumarins such as (2-benzothiazolyl)-7-diethylaminocoumarin.
  • anthraquinones such as 2-t-butylanthraquinone, 2-ethylanthraquinone and 1,2-benzanthraquinone
  • benzoins such as benzoin methyl ether, benzoin ethyl ether and benzoin isopropyl ether
  • mercaptos such as ethylene glycol di(3-mercaptopropionate), 2-mercaptobenzthiazole, 2-mercaptobenzoxazole and 2-mercaptobenzimidazole
  • glycines such as N-phenylglycine, N-methyl-N-phenylglycine, N-ethyl-N-(p-chlorophenyl)glycine, N-(4-cyanophenyl)glycine
  • 1-phenyl-1,2-butanedione-2-(o-methoxycarbonyl)oxime 1-phenyl-1,2-propanedione-2-(o(methoxycarbonyl)
  • Oximes 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-2-methyl-1[4-(methylthio)phenyl]-2-morpholinopropan-1-one
  • A-aminoalkylphenones such as 2,2′-bis(o-chlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole and the like.
  • oximes are preferred. More preferred are 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(o-benzoyl)oxime, bis(A -isonitrosopropiophenone oxime) isophthal, 1,2-octanedione-1-[4-(phenylthio)phenyl]-2-(o-benzoyloxime), OXE02, NCI-831. These are used alone or in combination of two or more. The structures of OXE-02 and NCI-831 are shown in the following formulas.
  • the content of the photopolymerization initiator is preferably 0.1 to 60 parts by mass, more preferably 0.2 to 40 parts by mass with respect to 100 parts by mass as the total amount of components (A) and (B).
  • amount is 0.1 part by mass or more, sufficient radicals are generated by light irradiation, and sensitivity is improved.
  • the solubility in the developer is improved.
  • the photopolymerizable compound examples include compounds having unsaturated double bond-containing groups such as vinyl groups, allyl groups, acryloyl groups, and methacryloyl groups, and unsaturated triple bond-containing groups such as propargyl groups.
  • the photopolymerizable compound may contain two or more of these unsaturated bond-containing groups.
  • conjugated vinyl groups, acryloyl groups, and methacryloyl groups are preferred from the standpoint of polymerizability.
  • the number of unsaturated bonds in the photopolymerizable compound is preferably 1 to 6 from the viewpoint of suppressing cracks in the cured product caused by excessive cross-linking points due to the polymerization reaction.
  • photopolymerizable compounds include diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane diacrylate, and trimethylolpropane.
  • photopolymerizable compounds include 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, dimethylol-tricyclodecane diacrylate, isobornyl acrylate, isobornyl methacrylate, pentaerythritol tri Acrylates, pentaerythritol tetraacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, methylenebisacrylamide, N,N-dimethylacrylamide, N-methylolacrylamide, 2,2,6 ,6-tetramethylpiperidinyl methacrylate, 2,2,6,6-tetramethylpiperidinyl acrylate, N-methyl-2,2,6,6-tetramethylpiperid
  • dipentaerythritol hexaacrylate dipentaerythritol hexamethacrylate, ethylene oxide-modified bisphenol A diacrylate, ethylene oxide-modified bisphenol A dimethacrylate, propylene oxide-modified bisphenol A diacrylate, and propylene oxide-modified bisphenol A dimethacrylate.
  • the content of the photopolymerizable compound in the resin composition of the present invention is 40 parts by mass with respect to 100 parts by mass of the total amount of components (A) and (B) from the viewpoint of improving the residual film rate after development. It is preferably 50 parts by mass or more, more preferably 50 parts by mass or more. On the other hand, from the viewpoint of improving the breaking elongation of the cured product, the content of the photopolymerizable compound is 150 parts by mass or less with respect to 100 parts by mass of the total amount of components (A) and (B). is preferred, and 100 parts by mass or less is more preferred.
  • the resin composition of the present invention may contain a thermal cross-linking agent.
  • the thermal cross-linking agent includes at least two groups selected from the group consisting of acrylic groups, methacrylic groups, epoxy groups, oxetanyl groups, benzoxazine structures, alkoxymethyl groups and methylol groups. is a compound.
  • Thermal cross-linking agents preferably include, but are not limited to, compounds having at least two alkoxymethyl or methylol groups.
  • "having at least two alkoxymethyl groups or methylol groups” means having two or more alkoxymethyl groups, having two or more methylol groups, and having a total of two or more alkoxymethyl groups and methylol groups.
  • a crosslinked structure can be formed by a condensation reaction with a resin and a molecule of the same kind.
  • a photoacid generator When used in combination with a photoacid generator, a wider range of designs is possible for improving sensitivity and breaking elongation of cured products.
  • thermal cross-linking agents include DML-PC, DML-PEP, DML-OC, DML-OEP, DML-34X, DML-PTBP, DML-PCHP, DML-OCHP, DML-PFP and DML-PSBP.
  • DML-POP DML-MBOC, DML-MBPC, DML-MTrisPC, DML-BisOC-Z, DMLBisOCHP-Z, DML-BPC, DML-BisOC-P, DMOM-PC, DMOM-PTBP, DMOM-MBPC, TriML -P, TriML-35XL, TML-HQ, TML-BP, TML-pp-BPF, TML-BPE, TML-BPA, TML-BPAF, TML-BPAP, TMOM-BP, TMOM-BPE, TMOM-BPA, TMOM -BPAF, TMOM-BPAP, HML-TPPHBA, HML-TPHAP, HMOM-TPPHBA, HMOM-TPHAP (the above are trade names, manufactured by Honshu Chemical Industry Co., Ltd.), "NIKALAC (registered trademark)" MX-290, NIKALAC MX -280, NIKALAC MX-
  • the content of the compound having at least two alkoxymethyl groups or methylol groups is preferably 10 parts by mass or less with respect to 100 parts by mass as the total amount of components (A) and (B). Within this range, a wide range of designs can be made more appropriately for improving the sensitivity and breaking elongation of the cured product.
  • the resin composition of the present invention preferably contains (G) a compound represented by formula (13) (hereinafter sometimes referred to as component (G)).
  • component (G) a compound represented by formula (13)
  • These compounds have a structure that does not have an aromatic ring in the molecule, so that the solubility in an alkaline developer increases, and patterning can be performed with high sensitivity.
  • the decomposition of (G) in the resin cured product due to heat or light irradiation including ultraviolet rays can be suppressed, and three-dimensional cross-linking can be formed, so it has a high breaking elongation and high crack resistance even after a thermal cycle test. It is possible to obtain a cured product having.
  • L 1 represents a structure represented by an alkylene group having 1 to 8 carbon atoms.
  • Compounds represented by formula (13) include, for example, “TEPIC (registered trademark)”-S, “TEPIC”-L, “TEPIC”-VL, and “TEPIC”-FL. From the viewpoint of compatibility and curability, it is preferable to use these compounds. A product name (manufactured by Shikoku Kasei Co., Ltd.) may also be used.
  • the content of the compound represented by formula (13) is 5 parts by mass or more with respect to 100 parts by mass of the total amount of components (A) and (B) from the viewpoint of improving crack resistance in thermal cycles. preferably 10 parts by mass or more.
  • the total amount of component (A) and component (B) may be 100 parts by mass or less with respect to 100 parts by mass. preferable.
  • the resin composition of the present invention may contain an adhesion improver.
  • Adhesion improvers include vinyltrimethoxysilane, vinyltriethoxysilane, epoxycyclohexylethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, Silane coupling agents such as 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, titanium chelating agents, aluminum chelating agents, aromatic amine compounds and alkoxy group-containing A compound obtained by reacting a silicon compound can be contained. You may contain 2 or more types of these.
  • adhesion to an underlying base material such as a silicon wafer, ITO, SiO 2 , or silicon nitride can be enhanced when developing a resin film.
  • resistance to oxygen plasma and UV ozone treatment used for cleaning can be enhanced.
  • the content of the adhesion improver in the resin composition is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass as the total amount of components (A) and (B). By setting it as such a range, the adhesiveness after image development is high, and the resin composition excellent in resistance to oxygen plasma and UV ozone treatment can be provided.
  • the resin composition of the present invention may contain a compound having a phenolic hydroxyl group in order to facilitate alkali developability. Since the resin composition contains a compound having a phenolic hydroxyl group, it is almost insoluble in an alkaline developer before exposure, and easily dissolved in an alkaline developer after exposure. Easier to develop in time. Therefore, it becomes easier to improve the sensitivity.
  • Compounds having a phenolic hydroxyl group selected from these points include, for example, Bis-Z, BisOC-Z, BisOPP-Z, BisP-CP, Bis26X-Z, BisOTBP-Z, BisOCHP-Z, BisOCR-CP, BisP -MZ, BisP-EZ, Bis26X-CP, BisP-PZ, BisP-IPZ, BisCRIPZ, BisOCP-IPZ, BisOIPP-CP, Bis26X-IPZ, BisOTBP-CP, TekP-4HBPA (Tetrakis P-DO-BPA), TrisPHAP , TrisPPA, TrisP-PHBA, TrisP-SA, TrisOCR-PA, BisOFP-Z, BisRS-2P, BisPG-26X, BisRS-3P, BisOC-OCHP, BisPC-OCHP, Bis25X-OCHP, Bis26X-OCHP, BisOCHP-OC , Bis236T-OCHP, methylenetris-FR-CR, BisRS-
  • the resin composition of the present invention may contain a surfactant as necessary.
  • a surfactant By containing a surfactant, it is possible to improve the wettability with the substrate and improve the film thickness uniformity of the coating film.
  • Commercially available compounds can be used as surfactants.
  • the silicone-based surfactants include the SH series, SD series, and ST series of Toray Dow Corning Silicone Co., Ltd., the BYK series of BYK Chemie Japan, the KP series of Shin-Etsu Silicone Co., Ltd., the Disform series of NOF Corporation, Toshiba Silicone Co., Ltd.'s TSF series, etc.
  • fluorine-based surfactants include Dainippon Ink Industry's "Megafac (registered trademark)” series, Sumitomo 3M's Florard series, and Asahi Glass' “Surflon (registered trademark)” series.
  • Surfactants obtained from acrylic and/or methacrylic polymers include, but are not limited to, Polyflow series from Kyoeisha Chemical Co., Ltd., and "Disparon (registered trademark)” series from Kusumoto Kasei Co., Ltd.
  • the content of the surfactant is preferably 0.001 parts by mass or more and 1 part by mass or less with respect to 100 parts by mass as the total amount of components (A) and (B).
  • the wettability between the resin composition and the substrate and the film thickness uniformity of the coating film can be improved without causing defects such as air bubbles and pinholes.
  • the resin composition of the present invention may contain a solvent.
  • Solvents include N-methyl-2-pyrrolidone, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2 - polar aprotic solvents such as imidazolidinone, N,N'-dimethylpropyleneurea, N,N-dimethylisobutyamide, methoxy-N,N-dimethylpropionamide, tetrahydrofuran, dioxane, propylene glycol monomethyl ether, propylene ethers such as glycol monoethyl ether; ketones such as acetone, methyl ethyl ketone and diisobutyl ketone; esters such as ethyl acetate, butyl acetate, isobutyl acetate,
  • the content of the solvent is preferably 100 parts by mass or more for the total amount of 100 parts by mass of the components (A) and (B), since the composition is easily dissolved. It is preferable to contain 1,500 parts by mass or less because it is easy to form.
  • the components (A) and (B) are mixed with, if necessary, a photoacid generator, a photopolymerization initiator, a thermal cross-linking agent, a compound having a phenolic hydroxyl group, an adhesion improver, a surfactant, a solvent, and the like.
  • the resin composition can be obtained by dissolving the resin composition.
  • Dissolution methods include heating and stirring.
  • the heating temperature is preferably set within a range that does not impair the performance of the resin composition, and is usually 25°C to 80°C.
  • the order of dissolving each component is not particularly limited, and for example, a method of dissolving compounds in order of low solubility can be mentioned.
  • the rotation speed is preferably set within a range that does not impair the performance of the resin composition, and is usually 200 rpm to 2000 rpm. Even when the mixture is stirred, it may be heated as necessary, and the temperature is usually 25°C to 80°C.
  • ingredients that tend to generate air bubbles during stirring and dissolution such as surfactants and some adhesion improvers
  • dissolving the other ingredients before adding them at the end will prevent poor dissolution of other ingredients due to air bubbles. can be prevented.
  • the viscosity of the resin composition of the present invention is preferably 2 to 5,000 mPa ⁇ s at 25°C.
  • a desired film thickness can be easily obtained by adjusting the solid content concentration so that the viscosity is 2 mPa ⁇ s or more.
  • the viscosity is 5,000 mPa ⁇ s or less, it becomes easy to obtain a highly uniform coating film.
  • the viscosity measurement here is a measurement using a TVE-25 type viscometer (manufactured by Toki Sangyo Co., Ltd.), a former E-type viscometer/DVE-type viscometer, and 1.1 mL of the resin composition of the present invention is sampled. and pour into the sample cup.
  • torque is selected in the range of 65-6000 ⁇ N ⁇ m and measured in the range of rotational speeds of 0.5-100 rpm.
  • the resin composition of the present invention having such a viscosity can easily be obtained by adjusting the combined content of component (A) and component (B) in 100% by mass of the resin composition of the present invention to 5 to 60% by mass. can get to
  • solid content concentration refers to components other than the solvent.
  • the obtained resin composition is preferably filtered using a filtration filter to remove dust and particles.
  • filter pore sizes include, but are not limited to, 0.5 ⁇ m, 0.2 ⁇ m, 0.1 ⁇ m, 0.05 ⁇ m, and 0.02 ⁇ m.
  • Materials for the filter include polypropylene (PP), polyethylene (PE), nylon (NY), polytetrafluoroethylene (PTFE), etc., and polyethylene and nylon are preferred.
  • the cured product of the present invention is a cured product obtained by curing the resin composition of the present invention.
  • the curing reaction cross-linking reaction and ring closure reaction proceed by heat, light, etc.
  • the obtained cured product has improved heat resistance, elongation at break and chemical resistance.
  • the cured product is heat treated for 5 minutes to 2 hours between 50 ° C. and 200 ° C. where the solvent in the resin composition before curing volatilizes
  • the cured product film after heat treatment is compared to the cured product film thickness before heat treatment. If the film thickness change rate is within 10%, it is assumed that the film is cured.
  • the cured product of the present invention has high elongation at break and high crack resistance even after a thermal cycle test, and can improve the reliability of the semiconductor device, electronic component, and display device of the present invention.
  • the cured product of the present invention contains a resin having a structure represented by formula (14) or (15).
  • These structures are structures in which R 1 of component (A) and R 2 of component (B) in the resin composition of the present invention react after heat curing, and when the cured product contains a resin having these structures A cured product having high elongation at break and high crack resistance can be obtained due to the extension of the polymer chain due to the reaction between the polymer ends.
  • R 1 of component (A) and R 2 of component (B) in the resin composition of the present invention react after heat curing, they have a structure represented by formula (14) or formula (15) due to their bonding mode. It will be.
  • the cured product of the present invention may have only the structure represented by formula (14), may have only the structure represented by formula (15), or may have formula (14) You may have the structure represented by the formula (15) and the structure represented by the formula (15) at the same time.
  • These structures in the cured product are obtained by hydrolyzing the cured product with an alkali or the like, or the cured product itself, by nuclear magnetic resonance spectroscopy (1H-NMR, 13C-NMR), It can be identified using infrared absorption spectroscopy (IR method), matrix-assisted laser desorption/ionization method-time-of-flight mass spectrometry (MALDI-TOFMS), and the like.
  • the cured product of the present invention preferably contains a resin having a trifluoromethyl group. Having a trifluoromethyl group improves the hydrophobicity of the cured product and improves the crack resistance in a thermal cycle test.
  • the cured product may contain a resin having a structure represented by formula (14) or formula (15) and a trifluoromethyl group.
  • the cured product may contain a resin that does not have the structure represented by the formula (14) or (15) and has a trifluoromethyl group. From the viewpoint of compatibility, the cured product preferably contains a resin having a structure represented by formula (14) or formula (15) and a trifluoromethyl group.
  • the method for producing a cured product of the present invention includes a step of applying the resin composition of the present invention, a step of forming a pattern through an ultraviolet irradiation step and a developing step, and a step of heating to form a relief pattern layer of the cured product. is preferably included.
  • resin film refers to a film obtained by coating the resin composition of the present invention on a substrate and drying it.
  • the resin composition of the present invention is applied onto a substrate and dried to obtain a resin film.
  • a resin composition containing the above photoacid generator, or a resin composition containing the above photopolymerization initiator and a photopolymerizable compound it is preferable to use a resin composition containing the above photoacid generator, or a resin composition containing the above photopolymerization initiator and a photopolymerizable compound. Drying is preferably carried out using an oven, hot plate, infrared rays, or the like, at a temperature of 50° C. to 140° C. for 1 minute to 2 hours.
  • substrates include silicon wafers, ceramics, gallium arsenide, organic circuit substrates, inorganic circuit substrates, and circuit-forming materials disposed on these substrates, but are not limited to these.
  • coating methods include a spin coating method, a slit coating method, a dip coating method, a spray coating method, and a printing method.
  • the coating film thickness varies depending on the coating method, the solid content concentration of the composition, the viscosity, etc., but the coating is usually applied so that the film thickness after drying is 0.1 to 150 ⁇ m.
  • the base material to be coated with the resin composition may be pretreated with the above-described adhesion improver.
  • a solution obtained by dissolving 0.5 to 20 parts by mass of an adhesion improver in a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and diethyl adipate is used.
  • a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and diethyl adipate.
  • examples thereof include methods of treating the surface of the base material by spin coating, slit die coating, bar coating, dip coating, spray coating, vapor treatment, and the like.
  • After treating the surface of the base material it may be dried under reduced
  • the process of forming a pattern through an ultraviolet irradiation process and a development process may include an exposure process of irradiating chemical warfare through a mask having a desired pattern on a photosensitive resin film.
  • Chemical warfare used for exposure includes ultraviolet rays, visible rays, electron beams, X-rays, and the like. is preferably used.
  • Developers include tetramethylammonium hydroxide, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, Aqueous solutions of alkaline compounds such as dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, hexamethylenediamine, N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, ⁇ -butyrolactone , polar solvents such as dimethylacrylamide, alcohols such as methanol, ethanol and isopropanol, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, ketones such as cyclopen
  • Solvents include, but are not limited to.
  • the developer may be a mixed solution of two or more selected from the above solvents.
  • the film can be rinsed with water, ethanol, alcohol such as isopropyl alcohol, ethyl lactate, ester such as propylene glycol monomethyl ether acetate, but not limited thereto.
  • the solution used for the rinse treatment may be a mixed solution of two or more selected from the above solvents.
  • the relief pattern layer of the cured product is formed by heat-treating the resin film to promote thermal cross-linking reaction and thermal ring-closing reaction.
  • the heat treatment of the resin film may be performed by gradually increasing the temperature, or may be performed while continuously increasing the temperature.
  • the heat treatment is preferably carried out for 5 minutes to 5 hours.
  • heat treatment is performed at 140° C. for 30 minutes, followed by heat treatment at 320° C. for 60 minutes.
  • the heat treatment temperature is preferably 140° C. or higher and 400° C. or lower.
  • the heat treatment temperature is preferably 140° C. or higher, more preferably 160° C. or higher, in order to advance the thermal crosslinking reaction and the thermal ring-closing reaction.
  • the heat treatment temperature is preferably 400° C. or lower, more preferably 350° C. or lower, in order to provide an excellent cured product and improve the yield.
  • the electronic component, display device or semiconductor device of the present invention comprises the cured product of the present invention.
  • the cured product of the present invention By having the cured product of the present invention, it is possible to obtain a highly reliable electronic component, display device or semiconductor device that does not generate cracks even after a thermal cycle test.
  • Examples of the configuration of the electronic component, display device, or semiconductor device of the present invention include, for example, the electronic component, display device, or semiconductor device described in JP-A-2020-66651 and WO 2021/085321. is not limited to
  • the present invention will be described below with reference to examples, etc., but the present invention is not limited to these examples.
  • the resin compositions in the examples were evaluated by the following methods.
  • a resin composition hereinafter referred to as varnish
  • a 1 ⁇ m polytetrafluoroethylene filter manufactured by Sumitomo Electric Industries, Ltd.
  • Terminal group R 1 of component (A) and terminal R 2 of component (B) in the resin composition 2 was calculated using 1H-NMR.
  • the measurement conditions are as follows. Measuring equipment: JNM-ECZ400R manufactured by JEOL RESONANCE Magnetic field strength: 400MHz Reference substance: Tetramethylsilane (TMS) Solvent: dimethyl sulfoxide (DMSO) Measurement temperature: 40°C In the obtained 1 H-NMR spectrum, the signal originating from the R 1 hydrogen atom appears at 5 to 6 ppm and the signal originating from the R 2 hydrogen atom appears at 6 to 6.5 ppm.
  • the total integrated value of the signal derived from the hydrogen atom of the amide bond appearing at 9 to 11 ppm is 100
  • the total integrated value of the signal derived from the hydrogen atom of the terminal group R 1 of the component (A) is r 1
  • the component (B) The total integral value of the signal derived from the hydrogen atom of the terminal group R 2 of is r 2
  • the weight-average molecular weight of the resin composition was obtained by standard polystyrene conversion using gel permeation chromatography (GPC).
  • the weight average molecular weight was measured using the following apparatus and conditions.
  • Measuring device Alliance e2695 manufactured by System Waters Detector: 2489 UV/Vis Detector (measurement wavelength 260 nm)
  • Measurement conditions column TOSOH TSK Guard column TOSOH TSK-GEL ⁇ -4000 TOSOH TSK-GEL ⁇ -2500
  • Developing solution NMP (containing 0.05 M lithium chloride and 0.05 M phosphoric acid)
  • Flow rate 0.4 ml/min
  • detector UV270 nm
  • the resin composition may be diluted with a solvent (NMP (containing 0.05 M lithium chloride and 0.05 M phosphoric acid)) for measurement so that detection can be performed with an analyzable peak intensity.
  • NMP containing 0.05 M lithium chloride and 0.05 M phosphoric acid
  • This film was cut into strips with a width of 1.5 cm and a length of 5 cm.
  • the elongation at break was measured by pulling at 5 mm/min. Measurement was performed on 10 strips per sample, and the average value of the top 5 points was obtained from the results.
  • a value of breaking elongation of 40% or more was rated as very good (3), a value of 20% or more and less than 40% was rated as good (2), and a value of less than 20% was rated as poor (1).
  • the varnish was applied on the evaluation substrate by a spin coating method using a coating and developing apparatus ACT-8 (manufactured by Tokyo Electron Ltd.) so that the film thickness after heat treatment at 120° C. for 3 minutes would be 8 to 12 ⁇ m.
  • Pre-baking was performed to produce a resin film. All pre-baking was performed at 120° C. for 3 minutes.
  • the resin film was heated from 50° C. to 250° C. at a rate of 3.5° C./min under a nitrogen stream using an inert oven (CLH-21CD-S, manufactured by Koyo Thermo Systems Co., Ltd.). After heating, heat treatment was performed at 250° C. for 1 hour to cure the resin film and obtain a cured product.
  • the film thickness after pre-baking is measured using a light interference film thickness measuring device Lambda Ace STM-602 manufactured by Dainippon Screen Mfg. Co., Ltd. with a refractive index of 1.629. Measured at a refractive index of 1.773.
  • the evaluation substrate (hereinafter referred to as the sample) was taken out.
  • the sample was put into a thermal cycle tester (conditions: -65°C/30min to 150°C/30min) and subjected to 200 cycles. After that, the sample was taken out and the presence or absence of cracks in the cured product was observed using an optical microscope. A total of 10 observations were made at 2 locations each at the center of the substrate and 4 edges of the substrate, with 0 cracks being evaluated as very good, 1-2 cracks being evaluated as good, and 3 or more cracks being generated. A sample with 4 cracks was rated as 2 as slightly defective, and a sample with 5 to 10 cracks was rated as 1 as defective. A smaller number of cracks indicates better crack resistance. The evaluation result is preferably 3 or 4, most preferably 4.
  • the photosensitive varnishes of Examples 17 to 20 were applied onto an 8-inch silicon wafer by spin coating using a coating and developing apparatus ACT-8 so that the film thickness after prebaking at 120° C. for 3 minutes was 12 ⁇ m.
  • exposure machine i-line stepper manufactured by Nikon Corporation, NSR-2005i9C was used with a mask capable of forming a circular opening pattern of 3 to 50 ⁇ m on the cylindrical copper wiring. It was exposed with an exposure dose of cm 2 .
  • the film was developed using a 2.38% by mass tetramethylammonium (TMAH) aqueous solution (manufactured by Tama Kagaku Kogyo), rinsed with pure water, shaken off and dried to obtain a relief pattern film.
  • TMAH tetramethylammonium
  • CLH-21CD-S manufactured by Koyo Thermo Systems Co., Ltd.
  • the temperature was raised to 250° C. at an oxygen concentration of 20 ppm or less at 3.5° C./min, and heat treatment was performed at 250° C. for 1 hour. .
  • the wafer was taken out and immersed in 45 mass % hydrofluoric acid for 1 minute to peel off the cured product from the wafer.
  • a diluted HCl aqueous solution was prepared by diluting 20 g of concentrated hydrochloric acid (35% HCl aqueous solution) with 400 ml of deionized water.
  • the diluted HCl aqueous solution was gradually added to neutralize the alkaline hydrolysis aqueous solution.
  • a precipitate generated after the neutralization was collected by filtration, and the separated precipitate was washed with about 850 ml of ion-exchanged water.
  • the precipitate after washing was put into a hot air dryer and dried at 80° C. for 24 hours.
  • the precipitate obtained after drying was subjected to structural analysis of the cured product using 1H-NMR and FT-IR.
  • the measurement conditions are as follows. Measurement: 1H-NMR Measuring equipment: JNM-ECZ400R manufactured by JEOL RESONANCE Magnetic field strength: 400MHz Reference substance: Tetramethylsilane (TMS) Solvent: dimethyl sulfoxide (DMSO) Measurement temperature: 40°C.
  • FT-IR Measuring equipment INVENIO S manufactured by BRUKER Mode: Transmission Specimen: KBr plate Accumulation times: 16
  • the structure of formula (14) or formula (15) can be calculated from the integral ratio of each hydrogen atom, and in the obtained FT-IR spectrum, the structure of formula (14) or formula (15) Since a characteristic peak derived from a carbonyl group appears, the chemical structure of formula (14) or formula (15) can be identified.
  • a characteristic signal derived from a hydrogen atom directly connected to the tertiary carbon of Formula (14) or Formula (15) appears at 2 to 4 ppm. A cured product in which the signal was observed was evaluated as 1, and a cured product in which the signal was not observed was evaluated as 0.
  • Examples 1 to 12, 23, 24 As shown in Table 1, a varnish was prepared by adding 20 g of NMP as a solvent to 5 g of component (A) and 5 g of component (B).
  • Example 13 A varnish was prepared by adding 20 g of NMP as a solvent to 2.5 g of A-2 and 7.5 g of B-2.
  • Example 14 A varnish was prepared by adding 20 g of NMP as a solvent to 7.5 g of A-2 and 2.5 g of B-2.
  • Example 15 A varnish was prepared by adding 20 g of NMP as a solvent to 2.5 g of A-12 and 7.5 g of B-12.
  • Example 16 A varnish was prepared by adding 20 g of NMP as a solvent to 7.5 g of A-12 and 2.5 g of B-12.
  • Example 17 and 18 As shown in Table 1, to 5 g of component (A) and 5 g of component (B), 2.0 g of the following (C) photoacid generator, 3.0 g of (D) thermal cross-linking agent, and 20 g of ⁇ -butyrolactone as a solvent were added. A varnish was produced by
  • Example 19 and 20 As shown in Table 1, for 5 g of component (A) and 5 g of component (B), 1.5 g of the following (E) photopolymerization initiator, 4.5 g of (F) photopolymerizable compound, and 20 g of ⁇ -butyrolactone as a solvent. In addition, a varnish was produced.
  • Example 21 A varnish was prepared by adding 20 g of NMP as a solvent to 1.5 g of A-2 and 8.5 g of B-2.
  • Example 22 A varnish was prepared by adding 20 g of NMP as a solvent to 8.5 g of A-2 and 1.5 g of B-2.
  • Table 1 shows the material amount ratio, molecular weight, breaking elongation, and crack evaluation results of the resin compositions obtained in Examples and Comparative Examples.
  • Example 25 A varnish was prepared by adding 1 g of G-1 and 20 g of NMP as a solvent to 5 g of A-2 and 5 g of B-2.
  • Example 26 A varnish was prepared by adding 1 g of G-2 and 20 g of NMP as a solvent to 5 g of A-2 and 5 g of B-2.
  • Example 27 A varnish was prepared by adding 1 g of G-2 and 20 g of NMP as a solvent to 5 g of A-11 and 5 g of B-11.
  • Example 28 A varnish was prepared by adding 1 g of G-2 and 20 g of NMP as a solvent to 5 g of A-12 and 5 g of B-12.
  • Example 29 A varnish was prepared by adding 0.5 g of G-2 and 20 g of NMP as a solvent to 5 g of A-11 and 5 g of B-11.
  • Example 30 A varnish was prepared by adding 10 g of G-2 and 20 g of NMP as a solvent to 5 g of A-11 and 5 g of B-11.
  • Example 31 A varnish was prepared by adding 0.5 g of G-3 and 20 g of NMP as a solvent to 5 g of A-11 and 5 g of B-11.
  • Example 32 A varnish was prepared by adding 0.5 g of G-4 and 20 g of NMP as a solvent to 5 g of A-11 and 5 g of B-11.
  • a varnish was prepared by adding 0.3 g of G-3 and 20 g of NMP as a solvent to 10 g of A-11.
  • a varnish was prepared by adding 1 g of G-3 and 20 g of NMP as a solvent to 10 g of A-11.
  • Table 2 shows the breaking elongation and crack evaluation results of the resin compositions obtained in each example and comparative example.
  • the resin composition of the present invention can be used for surface protective films such as semiconductor elements, interlayer insulating films, insulating layers of display devices such as organic light-emitting elements, flattening films of thin film transistor (hereinafter referred to as TFT) substrates, and wiring protective insulating films of circuit boards. , on-chip microlenses of solid-state imaging devices, flattening films for various displays and solid-state imaging devices, and solder resists for circuit boards.
  • surface protective films such as semiconductor elements, interlayer insulating films, insulating layers of display devices such as organic light-emitting elements, flattening films of thin film transistor (hereinafter referred to as TFT) substrates, and wiring protective insulating films of circuit boards.
  • TFT thin film transistor

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  • Engineering & Computer Science (AREA)
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  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de résine qui présente un allongement à la rupture élevé et qui présente une haute résistance à la fissuration même après un test de cyclage thermique, un produit durci obtenu à partir de ladite composition de résine, et un composant électronique, un dispositif d'affichage et un dispositif à semi-conducteur. La composition de résine selon l'invention contient une résine (A) et une résine (B), dont chacune présente une structure spécifiée au niveau des extrémités correspondantes, ladite résine (A) résine et ladite résine (B) contenant au moins un élément choisi dans le groupe constitué par un polyamide, un polyimide, un polybenzoxazole, les précurseurs correspondants et les copolymères correspondants.
PCT/JP2022/021888 2021-07-02 2022-05-30 Composition de résine, produit durci, procédé de production de produit durci, composant électronique, dispositif d'affichage et dispositif à semi-conducteur WO2023276517A1 (fr)

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JP2004224894A (ja) * 2003-01-22 2004-08-12 Nippon Shokubai Co Ltd マレイミド系共重合体
JP2010159402A (ja) * 2008-12-12 2010-07-22 Chisso Corp インクジェット用インク
WO2012133429A1 (fr) * 2011-03-29 2012-10-04 日産化学工業株式会社 Composition de résine photosensible négative
JP2016132736A (ja) * 2015-01-20 2016-07-25 日立化成株式会社 ポリイミド樹脂組成物及び粘着シート
WO2018003725A1 (fr) * 2016-06-29 2018-01-04 富士フイルム株式会社 Composition de résine photosensible négative, film durci, procédé de production de film durci, dispositif semi-conducteur, procédé de production de stratifié, procédé de production de dispositif semi-conducteur et précurseur de polyimide
WO2018037997A1 (fr) * 2016-08-22 2018-03-01 旭化成株式会社 Composition de résine photosensible et procédé de formation de motif en relief durci
JP2020020975A (ja) * 2018-08-01 2020-02-06 Jsr株式会社 感放射線性組成物およびその用途

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5386781B2 (ja) 2007-03-12 2014-01-15 日立化成デュポンマイクロシステムズ株式会社 感光性樹脂組成物、該樹脂組成物を用いたパターン硬化膜の製造方法及び電子部品
JP5640413B2 (ja) 2010-03-19 2014-12-17 東レ株式会社 ポジ型感光性樹脂組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004224894A (ja) * 2003-01-22 2004-08-12 Nippon Shokubai Co Ltd マレイミド系共重合体
JP2010159402A (ja) * 2008-12-12 2010-07-22 Chisso Corp インクジェット用インク
WO2012133429A1 (fr) * 2011-03-29 2012-10-04 日産化学工業株式会社 Composition de résine photosensible négative
JP2016132736A (ja) * 2015-01-20 2016-07-25 日立化成株式会社 ポリイミド樹脂組成物及び粘着シート
WO2018003725A1 (fr) * 2016-06-29 2018-01-04 富士フイルム株式会社 Composition de résine photosensible négative, film durci, procédé de production de film durci, dispositif semi-conducteur, procédé de production de stratifié, procédé de production de dispositif semi-conducteur et précurseur de polyimide
WO2018037997A1 (fr) * 2016-08-22 2018-03-01 旭化成株式会社 Composition de résine photosensible et procédé de formation de motif en relief durci
JP2020020975A (ja) * 2018-08-01 2020-02-06 Jsr株式会社 感放射線性組成物およびその用途

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