WO2024004462A1 - Composition de résine photosensible négative, procédé de production de film de résine à motif, film de résine à motif, et substrat de circuit semi-conducteur - Google Patents

Composition de résine photosensible négative, procédé de production de film de résine à motif, film de résine à motif, et substrat de circuit semi-conducteur Download PDF

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WO2024004462A1
WO2024004462A1 PCT/JP2023/019497 JP2023019497W WO2024004462A1 WO 2024004462 A1 WO2024004462 A1 WO 2024004462A1 JP 2023019497 W JP2023019497 W JP 2023019497W WO 2024004462 A1 WO2024004462 A1 WO 2024004462A1
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group
polymer
negative photosensitive
resin composition
photosensitive resin
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PCT/JP2023/019497
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English (en)
Japanese (ja)
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宏和 伊東
卓 小川
光香 安藤
了嗣 多田羅
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Jsr株式会社
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    • 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
    • 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
    • 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
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor

Definitions

  • the present invention relates to a negative photosensitive resin composition, a method for producing a patterned resin film, a patterned resin film, and a semiconductor circuit board.
  • 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, for example, Patent Document 1).
  • a composition for forming a patterned resin film such as an insulating film (hereinafter also referred to as "patterned resin film”) must have photolithographic properties that can be patterned by exposure and development.
  • the present invention solves the above problems, and provides a photosensitive resin composition that can form a resin film having excellent elongation and high reliability, and has photolithographic properties. It is an object of the present invention to provide a patterned resin film that is excellent and has high reliability and a method for manufacturing the same, and to provide a semiconductor circuit board including a patterned resin film that has excellent elongation and high reliability.
  • the present inventors conducted extensive studies to solve the above problems. As a result, it was discovered that the above problems could be solved by a negative photosensitive resin composition having the following composition, and the present invention was completed.
  • the present invention includes, for example, the following aspects.
  • a negative photosensitive resin composition containing a polymer (A), a crosslinking agent (B), and a photocation generator (C),
  • the polymer (A) has a reactive group Y at the end that reacts with the crosslinking agent (B) by the action of cations generated from the photocation generator (C) upon irradiation with light, and has the following formula: It has the structural unit shown in (a2), Photocation generation in which the photocation generator (C) generates an acid having a pKa (1) of ⁇ 3 or more and 3 or less, which is determined by a Gaussian function based on the pKa of methanesulfonic acid in an aqueous solution at 25° C., by light irradiation.
  • X 1 each independently represents a single bond, an oxygen atom, a sulfur atom, an ester bond, an amide bond, or -SO 2 -
  • R 1 represents a divalent hydrocarbon group, or a divalent group into which a functional group other than a heterocycle is introduced into the divalent hydrocarbon group
  • R 2 represents a divalent hydrocarbon group, a divalent group into which a functional group other than a heterocycle is introduced into the divalent hydrocarbon group, or a divalent heterocycle-containing group.
  • the reactive group Y is a phenolic hydroxyl group or a group that generates a phenolic hydroxyl group by the action of an acid.
  • R Z11 each independently represents an alkyl group, cycloalkyl group, alkoxy group, alkoxycarbonyl group, or alkylcarbonyl group
  • R Z12 each independently represents an alkyl group, cycloalkyl group, or naphthyl group.
  • n Z11 represents an integer from 1 to 7
  • X ⁇ represents a counter anion.
  • a semiconductor circuit board comprising a resin film having the pattern described in item [11].
  • the present invention it is possible to form a resin film having excellent stretchability and high reliability, and it is possible to provide a photosensitive resin composition having photolithographic properties, which has excellent stretchability and high reliability. It is possible to provide a patterned resin film having the following properties and a method for manufacturing the same, and to provide a semiconductor circuit board including a patterned resin film having excellent elongation and high reliability.
  • the present invention will be explained in detail below.
  • the negative photosensitive resin composition of the present invention (hereinafter also simply referred to as “composition of the present invention") comprises a polymer (A), a crosslinking agent (B), and a photocation generator (C ).
  • the polymer (A) has a reactive group Y at its end that reacts with the crosslinking agent (B) by the action of cations generated from the photocation generator (C) upon irradiation with light, and has the following formula: It has the structural unit shown in (a2).
  • the polymer (A) may be a polymer having one type of structural unit (a2) or a polymer having two or more types of structural units (a2).
  • ⁇ X 1 ⁇ X 1 in formula (a2) each independently represents a single bond, an oxygen atom, a sulfur atom, an ester bond, an amide bond, or -SO 2 -.
  • the composition of the present invention can be used to form a patterned resin film with a low dielectric constant, low dielectric loss tangent, and excellent elongation, and the polymer (A) has excellent solubility in organic solvents and storage stability. Since they are excellent in stability, single bonds, oxygen atoms and ester bonds are preferred, and oxygen atoms and ester bonds are more preferred.
  • ⁇ R 1 and R 2 ⁇ R 1 in formula (a2) is a divalent hydrocarbon group, or a divalent group into which a functional group other than a heterocycle is introduced into the divalent hydrocarbon group (hereinafter referred to as a "divalent substituted hydrocarbon group"). ).
  • R 2 in formula (a2) represents a divalent hydrocarbon group, a divalent substituted hydrocarbon group, or a divalent heterocycle-containing group.
  • R 1 is preferably a divalent hydrocarbon group
  • R 2 is preferably a divalent heterocycle-containing group or a divalent hydrocarbon group, and more preferably a divalent heterocycle-containing group.
  • the dipole moment in the short axis direction of the polymer (A) becomes small, and when using the composition of the present invention, This is preferable because a patterned resin film with low dielectric constant, low dielectric loss tangent, and excellent stretchability can be formed.
  • divalent hydrocarbon group examples include an alkanediyl group, an alicyclic-containing hydrocarbon group, and an aromatic ring-containing hydrocarbon group.
  • aromatic ring-containing hydrocarbon groups are preferred because they can form a patterned resin film. Note that a hydrocarbon group having both an alicyclic ring and an aromatic ring is classified as an aromatic ring-containing hydrocarbon group.
  • the number of carbon atoms in the alkanediyl group is usually 1 to 30, preferably 1 to 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, Linear alkanediyl group such as decane-1,10-diyl group; formed by adding one or more side chains consisting of an alkyl group having 1 to 4 carbon atoms to the above-exemplified linear alkanediyl group Branched alkanediyl groups are mentioned.
  • the alicyclic-containing hydrocarbon group usually has 3 to 30 carbon atoms, preferably 5 to 20 carbon atoms.
  • Examples of the alicyclic ring, that is, aliphatic hydrocarbon ring include monocyclic aliphatic hydrocarbon rings such as cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, and cyclodecane ring; norbornane ring, norbornene ring, and adamantane ring. , a tricyclo[5.2.1.0 2,6 ]decane ring, a tricyclo[5.2.1.0 2,6 ]heptane ring, and other polycyclic aliphatic hydrocarbon rings.
  • 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); for example, Examples include 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 connected.
  • a monovalent group e.g., cycloalkyl group
  • a divalent group e.g., cycloalkanediyl group
  • aromatic ring-containing hydrocarbon group examples include 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).
  • arylene group refers to a divalent hydrocarbon group having one or more aromatic rings, that is, aromatic hydrocarbon rings, and having two bonds on the aromatic hydrocarbon ring. .
  • the two bonds may exist in the same aromatic hydrocarbon ring or in different aromatic hydrocarbon rings.
  • Examples of the aromatic hydrocarbon ring contained in the arylene group include benzene ring; benzo-fused rings such as naphthalene ring, anthracene ring, tetracene ring, and pentacene ring.
  • the number of carbon atoms in the arylene group is preferably 6 to 50, more preferably 6 to 30.
  • arylene group examples include phenylene group, naphthalenediyl group, anthracenediyl group, tetracenediyl group, pentacenediyl group, and divalent groups shown in the following formulas (a1-1) to (a1-4).
  • Each aromatic hydrocarbon ring (e.g. 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.
  • Z is each 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 from 0 to 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.
  • R 11 is each independently a hydrogen atom or an alkyl group, preferably an alkyl group having 1 to 10 carbon atoms.
  • the divalent substituted hydrocarbon group in R 1 and R 2 is a group in which a functional group other than a heterocycle is introduced into the divalent hydrocarbon group.
  • the functional group is selected from, for example, a halogen atom, a nitro group, a cyano group, an allyl group, and a vinyl group. Further, from the viewpoint of low dielectric properties, the functional group is preferably not a highly polar functional group such as a hydroxyl group.
  • Examples of the divalent heterocycle-containing group for R 2 include 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 Examples include aromatic imide ring-containing groups having a structure in which a cyclic imide group is fused to an aromatic ring.
  • Examples of the cyclic imide group and the alicyclic imide ring-containing group having a structure in which a cyclic imide group is fused to an alicyclic hydrocarbon group include groups represented by the following formulas.
  • heteroaromatic ring examples include N-containing aromatic rings such as a pyrimidine ring, pyrazine ring, pyridazine ring, pyridine ring, pyrrole ring, and pyrazole ring; O-containing aromatic rings such as a furan ring; and S-containing aromatic rings such as a thiophene ring. N- and O-containing aromatic rings such as benzoxazole rings and isoxazole rings; N- and S-containing aromatic rings such as isothiazole rings.
  • aromatic imide ring-containing group examples include a phthalimide group and a group represented by the following formula.
  • the heterocycle can have one or more substituents, for example 1 to 2, bonded to the heterocycle, and the substituents include, for example, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an allyl group. and a monovalent hydrocarbon group having 1 to 20 carbon atoms such as a vinyl group, a halogenated monovalent hydrocarbon group having 1 to 20 carbon atoms, a nitro group, and a cyano group, and other than the above-mentioned reactive groups. Examples include groups. Further, from the viewpoint of low dielectric properties, 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 halogenated hydrocarbon group is preferably 1 to 3. When the heterocycle has two or more substituents, each substituent may be the same or different.
  • heteroaromatic ring-containing groups benzoxazole ring-containing groups, aromatic imide ring-containing groups, and pyrimidine can be used to form patterned resin films with 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 is preferable, a divalent group obtained by removing two hydrogen atoms from pyrimidine, pyrazine or pyridazine is more preferable, and a divalent group obtained by removing two hydrogen atoms from pyrimidine.
  • divalent groups are particularly preferred.
  • the reactive group Y contained in the polymer (A) is a group that reacts with the crosslinking agent (B) by the action of cations generated from the photocation generator (C) upon irradiation with light.
  • the cation promotes the crosslinking reaction between the polymer (A) and the crosslinking agent (B).
  • the reactive group Y examples include a thiol group, an amino group, a sulfonic acid group, a carboxy group, a phenolic hydroxyl group, and a group that generates these groups by the action of an acid.
  • the composition of the present invention can be used to form a patterned resin film with a low dielectric constant, low dielectric loss tangent, and excellent elongation, and the polymer (A) has a high solubility in organic solvents.
  • a phenolic hydroxyl group and a group that generates a phenolic hydroxyl group by the action of the acid are preferred because they have excellent storage stability and storage stability.
  • Examples of the group generating a phenolic hydroxyl group include a group protected with an acid-dissociable group such as an acetal-protected phenolic hydroxyl group and a t-butyl group-protected phenolic hydroxyl group.
  • R 1 is preferably an aromatic ring-containing hydrocarbon group, more preferably an arylene group.
  • R 2 is preferably a heterocycle-containing group, and is preferably a divalent group obtained by removing two hydrogen atoms from pyrimidine, pyrazine, or pyridazine, or a cyclic imide-containing group. More preferably, it is a divalent group obtained by removing two hydrogen atoms from pyrimidine, or a cyclic imide-containing group.
  • the polymer (A) has a structural unit in which R 1 is an aromatic ring-containing hydrocarbon group and R 2 is a heterocycle-containing group in the formula (a2), and has a reactive group Y at the terminal.
  • R 1 is an arylene group
  • R 2 is a divalent group obtained by removing two hydrogen atoms from pyrimidine, or a cyclic imide-containing group.
  • the reactive group Y is present only at the end.
  • a patterned resin film having a low dielectric constant, low dielectric loss tangent, and excellent extensibility can be formed using the composition of the present invention.
  • Preferred embodiments of the polymer (A) include polyimide, polyimide precursors, and polyether, and a more preferred embodiment is polyether.
  • the polymer (A) is a linear polymer having a structural unit (a2) and a reactive group Y only at the end of the polymer chain, particularly a linear polymer represented by the following formula (AA).
  • a polymer (AA) is preferable because a patterned resin film with excellent extensibility can be formed using the composition of the present invention.
  • Y represents a reactive group Y
  • R 1 , R 2 and X have the same meanings as the same symbols in formula (a2).
  • n indicates that the structural unit (a2) in parentheses is a repeating structural unit. That is, the repeating structural unit (a2) is bonded like...-R 2 -X-R 1 -X-R 2 -X-R 1 -X-....
  • the repeating structural unit (a2) may be one type or two or more types.
  • m and p each independently represent 0 or 1. Note that -(X-R 1 )p- in formula (AA) may be one type or two or more types.
  • 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 (A). 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 ratio of the repeating structural unit (a2) can be measured by 13 C-NMR.
  • the reactive group Y contained in the polymer (A) can be qualitatively or quantitatively analyzed by combining matrix-assisted laser desorption ionization, three-dimensional nuclear magnetic resonance, titration, etc. can.
  • the weight average molecular weight (Mw) of the polymer (A) measured by gel permeation chromatography is determined from the viewpoint of the resolution of the composition of the present invention and the extensibility of the resin film obtained from the composition of the present invention.
  • Mw weight average molecular weight
  • in terms of polystyrene is usually 1,000 to 200,000, preferably 2,000 to 100,000, and more preferably 5,000 to 100,000. Details of the method for measuring Mw are as described in Examples.
  • the polymer (A) may be used alone or in combination of two or more.
  • the lower limit of the content of the polymer (A) in 100% by mass of the solid content of the composition of the present invention is usually 20% by mass, preferably 40% by mass, and more preferably 60% by mass; the upper limit is: It is usually 99% by mass, preferably 95% by mass.
  • the content ratio of the polymer (A) is greater than or equal to the lower limit value or less than the upper limit value, a negative photosensitive resin composition that can form a patterned resin film with high resolution tends to be obtained.
  • the solid content refers to all components other than the organic solvent (E) described below that may be included in the composition of the present invention.
  • Polymer (A) can be produced, for example, by polycondensation. More specifically, when X is an oxygen atom, a bisphenol compound or a dihalogen compound is used as a monomer, and an alkali metal compound is used as a polymerization catalyst, and when X is a sulfur atom, a bisthiol compound or a dihalogen compound is used as a monomer. , and an alkali metal compound as a polymerization catalyst, and when X is an ester bond, it can be produced using a dicarboxylic acid compound or a dihalogen compound as a monomer, and an alkali metal compound as a polymerization catalyst.
  • the polymer (A) a polymer (A11) in which X is an oxygen atom in formula (a2) and has a phenolic hydroxyl group as the reactive group Y will be described.
  • the polymer (A11) can be obtained, for example, by polymerizing at least a phenol compound (aa1) having two phenolic hydroxyl groups and a halogen compound (aa2) having two halogen atoms.
  • the phenol compound (aa1) and the halogen compound (aa2) are polymerized in a suitable polymerization solvent in the presence of an alkali metal compound.
  • the amount of the halogen compound (aa2) to be used is usually less than 100 mol, preferably 90.0 to 99.9 mol, per 100 mol of the phenol compound (aa1). With such a quantitative ratio, a polymer having a phenolic hydroxyl group at the polymer terminal can be obtained.
  • alkali metal compound examples include carbonates, hydrogen carbonates, and hydroxides of alkali metals such as lithium, sodium, and potassium.
  • carbonates and hydroxides are preferred, and potassium carbonate, sodium carbonate, potassium hydroxide, and sodium hydroxide are more preferred.
  • the polymer (A) in which X is other than an oxygen atom in formula (a2) can be produced, for example, by known polycondensation.
  • the composition of the present invention further contains a crosslinking agent (B) for purposes such as curing the patterned resin film.
  • the crosslinking agent (B) is a crosslinking component that reacts with the reactive group Y in the polymer (A) by the action of cations generated from the photocation generator (C) upon irradiation with light.
  • crosslinking agent (B) examples include a crosslinking agent (b1) having at least two groups represented by -R B1 --O-R B2 such as a methylol group and an alkoxymethyl group, and a crosslinking agent (b1) having at least two oxetane rings.
  • examples include agents. Among these, crosslinking agent (b1) is preferred.
  • R B1 is an alkanediyl group, preferably an alkanediyl group having 1 to 10 carbon atoms
  • R B2 is a hydrogen atom or an alkyl group, preferably a hydrogen atom. Or an alkyl group having 1 to 10 carbon atoms.
  • Examples of the alkanediyl group in R B1 include a methylene group and an ethylene group, and examples of the alkyl group in R B2 include a methyl group, an ethyl group, a propyl group, and a butyl group.
  • crosslinking agent (b1) examples include compounds having two or more amino groups bonded with groups represented by -R B1 -O-R B2 , methylol group-containing phenol compounds, and alkylmethylol group-containing phenol compounds. .
  • Examples of the amino group to which the group represented by -R B1 -O-R B2 is bonded include a group represented by formula (b1-1) and a group represented by formula (b1-2).
  • R B1 is an alkanediyl group having 1 to 10 carbon atoms
  • R B2 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • m is 1 or 2
  • n is 0 or 1
  • m+n is 2
  • * is a bond.
  • Examples of the crosslinking agent (b1) include nitrogen atom-containing compounds such as polymethylolated melamine, polymethylolated glycoluril, polymethylolated guanamine, and polymethylolated urea; Examples include compounds in which all or a portion of the CH 2 OH group bonded to the alkyl ether is alkyl etherified.
  • examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, a propyl group, and a butyl group, and these may be the same or different.
  • the active methylol groups that have not been alkyl etherified may be self-condensed within one molecule, or may be condensed between two molecules, resulting in the formation of an oligomer component.
  • crosslinking agent (b1) examples include those described in JP-A-6-180501, JP-A-2006-178059, and JP-A-2012-226297.
  • melamine crosslinking agents such as polymethylolated melamine, hexamethoxymethylated melamine, hexaethoxymethylated melamine, hexapropoxymethylated melamine, hexabutoxymethylated melamine; polymethylolated glycoluril, 1,3, Glycoluril crosslinking agents such as 4,6-tetrakis(methoxymethyl)glycoluril and tetrabutoxymethylglycoluril; 3,9-bis[2-(3,5-diamino-2,4,6-triazaphenyl) ethyl]2,4,8,10-tetraoxospiro[5.5]undecane, 3,9-bis[2-(3,5-diamino-2,4,6-triazaphenyl)propyl
  • Examples of the methylol group-containing phenol compound and the alkylmethylol group-containing phenol compound include 2,6-dimethoxymethyl-4-t-butylphenol and 2,6-dimethoxymethyl-p-cresol.
  • the crosslinking agent (B) may be used alone or in combination of two or more.
  • the lower limit of the content of the crosslinking agent (B) based on 100 parts by mass of the polymer (A) in the composition of the present invention is usually 0.1 part by mass, preferably 1 part by mass, and more preferably 2 parts by mass;
  • the upper limit is usually 40 parts by weight, preferably 30 parts by weight, and more preferably 20 parts by weight.
  • the composition of the present invention contains a photocation generator (C).
  • the photocation generator (C) is a compound that generates cations such as H + when irradiated with light, which promotes the crosslinking reaction between the reactive group in the polymer (A) and the crosslinking agent (B). It is.
  • cations are generated from the photocation generator (C) in the exposed area, and based on the action of the cations, the reactive groups in the polymer (A) It is thought that the crosslinking reaction with the crosslinking agent (B) is promoted, a crosslinked structure is formed in the exposed area, and the solubility in the developer decreases.
  • the photocation generator (C) is an acid whose pKa (1) determined by Gaussian function is -3 or more and 3 or less, based on the pKa of methanesulfonic acid in an aqueous solution at 25°C.
  • a photocation generator (C1) generated by.
  • the lower limit of the pKa(1) is preferably -2.9, and the upper limit is preferably 1, more preferably 0.5.
  • the photocation generator (C) contains the photocation generator (C1), a patterned resin film with excellent elongation, high reliability, and high resolution can be obtained. Cheap.
  • pKa (1) was calculated based on the pKa of methanesulfonic acid in an aqueous solution at 25°C by the density functional (DFT) method at the B3LYP/6-311G* calculation level using the quantum chemical calculation program Gaussian09. Ru.
  • acids with a pKa (1) of -3 or more and 3 or less generated from the photocation generator (C1) include hydrochloric acid, nitric acid, trifluoroacetic acid, and alkyl group-substituted benzenes such as p-toluenesulfonic acid.
  • acids with a pKa (1) of -3 or more and 3 or less generated from the photocation generator (C1) include hydrochloric acid, nitric acid, trifluoroacetic acid, and alkyl group-substituted benzenes such as p-toluenesulfonic acid.
  • substituted or unsubstituted aromatic sulfonic acids such as sulfonic acid and alkoxy-substituted benzenesulfonic acids such as p-methoxybenzenesulfonic acid.
  • substituted or unsubstituted aromatic sulfonic acids are preferred from the viewpoint of difficulty in volat
  • Examples of the photocation generator (C1) include chlorine-containing compounds, diazomethane compounds, imidosulfonate compounds, oxime sulfonate compounds, and onium salts. Among these, chlorine-containing compounds, imidosulfonate compounds, oxime sulfonate compounds, and onium salts are preferred from the viewpoint of sensitivity and insulation.
  • chlorine-containing compound examples include chloroalkyl group-containing hydrocarbon compounds and chloroalkyl group-containing heterocyclic compounds.
  • preferred chlorine-containing compounds include; phenyl-bis(trichloromethyl)-s-triazine, 4-methoxyphenyl-bis(trichloromethyl)-s-triazine, styryl-bis(trichloromethyl)-s-triazine, naphthyl-bis(trichloromethyl)-s-triazine, 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis-(trichloromethyl)-1,3,5-triazine, etc.
  • Examples include trichloromethyl-s-triazine derivatives.
  • Examples of the imidosulfonate compound and oxime sulfonate compound include the compounds described in paragraphs [0057] to [0076] of Japanese Patent No. 6279614, which are described herein. Specific examples include the compound (C1-2) described in the Examples section.
  • Examples of the onium salt include triarylsulfonium salts, diaryliodonium salts, and salts represented by the following formula (Z1), from the viewpoint of high acid generation efficiency and high resolution for i-line, A compound represented by the following formula (Z1) is preferred. Specific examples include the compound (C1-1) described in the Examples section.
  • R Z11 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, an alkoxycarbonyl group, or an alkylcarbonyl group
  • each R Z12 independently represents an alkyl group, a cycloalkyl group, or a naphthyl group, or represents a ring structure formed by two R Z12s
  • n Z11 represents an integer from 1 to 7
  • X ⁇ represents a counter anion.
  • Examples of the alkyl group as R Z11 and R Z12 include an alkyl group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms.
  • Examples of the cycloalkyl group as R Z11 and R Z12 include a cycloalkyl group having 3 to 20 carbon atoms.
  • Examples of the alkoxy group for R Z11 include an alkoxycarbonyl group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms.
  • Examples of the alkoxycarbonyl group for R Z11 include alkoxycarbonyl groups having 1 to 5 carbon atoms.
  • Examples of the alkylcarbonyl group for R Z11 include alkylcarbonyl groups having 1 to 5 carbon atoms.
  • Examples of the ring structure formed by two R Z12 include the structures shown below.
  • n X1 represents an integer from 1 to 5.
  • the photocation generator (C1) may be used alone or in combination of two or more.
  • the lower limit of the content of the photocation generator (C1) based on 100 parts by mass of the polymer (A) in the composition of the present invention is usually 0.01 parts by mass, preferably 0.1 parts by mass, more preferably 0.01 parts by mass.
  • the upper limit is usually 30 parts by weight, preferably 20 parts by weight, and more preferably 10 parts by weight.
  • the photocation generator (C) may contain a photocation generator (C2) other than the photocation generator (C1) within a range that does not impair the effects of the present invention.
  • the pKa (1) of the acid generated from each photocation generator by light irradiation is It is preferable that the total sum obtained by multiplying the content ratio (mol %) of is -3 or more and 3 or less.
  • a photosensitive acid generator that generates an acid upon irradiation with light is preferable, and examples thereof include onium salt compounds, halogen-containing compounds, sulfone compounds, sulfonic acid compounds, sulfonimide compounds, and diazomethane compounds. It will be done.
  • Examples of the photocation generator (C2) such as onium salt compounds, halogen-containing compounds, sulfonic compounds, sulfonic acid compounds, sulfonimide compounds, and diazomethane compounds, include paragraph [0074] of JP-A No. 2014-186300. - [0079] (excluding compounds corresponding to the photocation generator (C1)), and these are considered to be described in this specification.
  • the composition of the present invention may contain a surfactant (D) from the viewpoint of improving coating properties, antifoaming properties, leveling properties, and the like.
  • the surfactant is not particularly limited, and known nonionic surfactants, fluorine surfactants, and silicone surfactants can be used.
  • Examples of commercially available surfactants include BM-1000, BM-1100 (manufactured by BM Chemie), Megafac F142D, Megafac F172, Megafac F173, Megafac F183 (manufactured by Dainippon Ink and Chemicals Co., Ltd.), and Florado FC- 135, FC-170C, FC-430, FC-431 (manufactured by Sumitomo 3M Ltd.), Surflon S-112, S-113, S-131, S-141, S-145 ( Commercially available under the names of SH-28PA, SH-190, SH-193, SZ-6032, SF-8428 (manufactured by Toray Silicone Co., Ltd.), NBX-15 (manufactured by Neos Co., Ltd.), etc.
  • Fluorinated surfactants silicone surfactants commercially available under the names of KL-245, KL-270 (manufactured by Kyoeisha Chemical Co., Ltd.), SH28PA (manufactured by Toray Dow Corning); Nonion S -6, Nonion 0-4, Pronone 201, Pronone 204 (manufactured by NOF Corporation), Emulgen A-60, Emulgen A-90, Emulgen A-500 (manufactured by Kao Corporation), KL-600 (Kyoeisha Chemical) Examples include nonionic surfactants commercially available under the names of Co., Ltd.) and the like.
  • the surfactant (D) may be used alone or in combination of two or more.
  • the surfactant (D) is preferably used in an amount of 5 parts by weight or less, more preferably 0.01 to 2 parts by weight, based on 100 parts by weight of the polymer (A).
  • the composition of the present 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 can dissolve or disperse each component such as the polymer (A), the crosslinking agent (B), and the photocation generator (C).
  • Examples of the organic solvent (E) include ketone solvents, alcohol solvents, ether solvents, ester solvents, amide solvents, and hydrocarbon solvents.
  • ketone solvent examples include 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- Chained ketone solvents such as n-hexylketone, di-iso-butylketone, and trimethylnonanone; cyclic ketone solvents such as cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone, and methylcyclohexanone; 2,4-pentanedione; Examples include acetonyl acetone and acetophenone.
  • alcohol solvents 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; Examples include polyhydric alcohol solvents having 2 to 18 carbon atoms such as 1,2-propylene glycol; partial ether solvents of polyhydric alcohols 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, etc.
  • 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, etc.
  • aromatic ring-containing ether solvents include 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; Polyhydric carboxylic acid diester solvents such as diethyl oxalate; lactone solvents such as ⁇ -butyrolactone and ⁇ -valerolactone; 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
  • Polyhydric carboxylic acid diester solvents such as
  • amide solvent examples 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 solvent 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, polymers other than the polymer (A); additives such as low-molecular phenol compounds, adhesion aids, crosslinked fine particles, leveling agents, sensitizers, inorganic fillers, and quenchers. .
  • a compound having a reactive functional group such as a carboxy group, a methacryloyl group, a vinyl group, an isocyanate group, an epoxy group, an amino group, or a silane coupling agent
  • a reactive functional group such as a carboxy group, a methacryloyl group, a vinyl group, an isocyanate group, an epoxy group, an amino group, or a silane coupling agent
  • Specific examples include polyhydric acids such as oxalic acid, silane coupling agents such as 3-glycidoxypropyltrimethoxysilane, and nitrogen heterocyclic compounds such as pyridine, pyrazine, pyrimidine, and benzotriazole.
  • the composition of the present invention can be manufactured by uniformly mixing the components constituting the composition of the present invention. Further, in order to remove foreign substances, after uniformly mixing the above-mentioned components, the resulting mixture can be filtered using a filter or the like.
  • a patterned resin film obtained by curing the composition of the present invention has excellent extensibility. This is presumed to be due to the following reasons. Since the polymer (A) has the reactive group Y substantially only at the end of the polymer chain, when the composition of the present invention is crosslinked, the crosslinking occurs so that the polymer chain in the polymer (A) is chain-extended. Therefore, the crosslinking density is low, and on the other hand, it is thought that the polymer chains are often entangled with each other, resulting in a gentle interaction between the polymer chains. Therefore, it is presumed that the extensibility of the resulting 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 short axis direction (perpendicular to the main chain direction of the polymer) in the repeating structural unit of the polymer used is small.
  • crosslinking mainly occurs at the end of the polymer chain rather than in the repeating structural unit (a2) of the polymer (A)
  • it is assumed that the change in the dipole moment is small through 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 below.
  • a hygroscopic 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 amount of the highly polar functional group introduced into the polymer is considered to be large, resulting in a high dielectric constant and dielectric loss tangent.
  • the present invention since a developer containing an organic solvent can be used to form a patterned resin film, it is possible to reduce the amount of the highly polar functional group introduced into the polymer, and therefore, the dielectric constant is low. , and a low dielectric loss tangent can be achieved.
  • the method for producing a resin film having a pattern (patterned resin film) of the present invention includes 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.
  • the method includes 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 usually applied onto a substrate so that the thickness of the patterned resin film finally obtained is, for example, 0.1 to 100 ⁇ m.
  • the substrate coated with the composition is usually heated at 50 to 140° C. for 10 to 360 seconds using an oven or a hot plate. In this way, a coating film made of the composition of the present invention is formed on the substrate.
  • Examples of the substrate 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 surfaces of these substrates.
  • Examples of the coating method include a dipping method, a spray method, a bar coating method, a roll coating method, a spin coating method, a curtain coating method, a gravure printing method, a silk screen method, and an inkjet method.
  • step (2) the coating film is selectively exposed to light using, for example, a contact aligner, a stepper, or a scanner.
  • “selectively” means through a photomask on which a predetermined mask pattern is formed.
  • the exposure light examples include ultraviolet rays and visible light, and light with a wavelength of 200 to 500 nm (eg, i-line (365 nm)) is usually used.
  • the amount of irradiation due to exposure varies depending on the type of each component in the composition of the present invention, the blending ratio, the thickness of the coating film, etc., but the amount of exposure is usually 100 to 1500 mJ/cm 2 .
  • heat treatment after exposure In order to allow the crosslinking reaction to proceed sufficiently, it is preferable to perform a heat treatment (post-exposure bake) after exposure.
  • the conditions for 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. That's about it.
  • step (3) the exposed coating film is developed with a developer containing an organic solvent to dissolve and remove non-exposed areas, thereby forming a desired patterned resin film on the substrate.
  • a developer containing an organic solvent to dissolve and remove non-exposed areas, thereby forming a desired patterned resin film on the substrate.
  • the developing method include a shower developing method, a spray developing method, an immersion developing method, and a paddle developing method.
  • the developing conditions are usually 20 to 40°C for about 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, or liquids containing the organic solvents.
  • organic solvents include the compounds exemplified as organic solvent (E). Among these, at least one selected from ketone solvents, ester solvents and amide solvents is preferred.
  • components other than the organic solvent in the developer include water, silicone 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, even more preferably 95% by mass or more, and particularly preferably 99% by mass or more.
  • 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 an uneven structure, and examples include a line and space pattern, a dot pattern, a hole pattern, and a lattice pattern.
  • Step (4)> In the method for producing a patterned resin film of the present invention, after step (3), in order to fully develop the characteristics as an insulating film, the patterned resin film is sufficiently heated by heat treatment (post-baking) as necessary. It can have a step (4) of curing. Curing conditions are not particularly limited, but depending on the intended use of the patterned resin film, heating is performed, for example, 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, a surface protective film, an interlayer insulating film, a planarizing film) included in a semiconductor circuit board.
  • an insulating film eg, a surface protective film, an interlayer insulating film, a planarizing film
  • a semiconductor circuit board including a resin film having the above-described pattern (patterned resin film) can be manufactured.
  • the semiconductor circuit board has a patterned resin film formed from the above-described composition of the present invention, preferably a patterned insulating film such as a surface protection film, an interlayer insulating film, and a flattening film, so that it can be used as a high-frequency circuit board. Useful.
  • the contents of the flask were heated at 130° C. for 6 hours, and water generated during heating was removed from the Dean-Stark tube as needed. After cooling the contents of the flask to room temperature, the precipitated solids were filtered off, methanol was added to the filtrate, the precipitated solids were washed with methanol, and these solids were dried to obtain the polymer (A1). Ta.
  • the obtained polymer (A1) was analyzed by 13 C-NMR etc., it was revealed that it was a polymer having the structure shown in formula (A1).
  • the weight average molecular weight (Mw) of the polymer (A1) was 8,000.
  • the negative photosensitive resin composition was spin-coated onto a 6-inch silicon wafer, and then heated at 110° C. for 5 minutes using a hot plate to form a coating film (thickness: 10 ⁇ m).
  • a coating film (thickness: 10 ⁇ m).
  • an aligner manufactured by Suss Microtec, model "MA-150"
  • the coating film was exposed to ultraviolet rays from a high-pressure mercury lamp through a photomask so that the exposure amount at a wavelength of 365 nm was 500 mJ/ cm2. did.
  • immersion development was performed at 23° C. for 3 minutes using a developer (cyclopentanone).
  • the developed coating film was heated in an oven under a nitrogen atmosphere under the heating conditions (curing temperature and curing time) shown in Table 2 to produce a patterned resin film.
  • the resin film having the manufactured pattern was observed with an electron microscope and evaluated based on the following criteria. Good: A square pattern of 50 ⁇ m in length and 50 ⁇ m in width was formed. ⁇ : A square pattern of 50 ⁇ m in length and 50 ⁇ m in width cannot be formed.
  • the negative photosensitive resin composition was applied onto a substrate with a release material, and then heated in an oven at 110° C. for 5 minutes to form 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 using an oven under the heating conditions (curing temperature and curing time) shown in Table 2 under a nitrogen atmosphere.
  • the coated film after heating in post-baking was peeled off from the substrate with the mold release material to obtain a resin film with a thickness of 15 ⁇ m.
  • the obtained resin film was cut into strips measuring 5 cm in length and 0.5 cm in width.
  • the tensile elongation at break (%) of the rectangular resin film was measured using a tensile compression tester (product name "SDWS-0201 model", manufactured by Imada Seisakusho Co., Ltd.).
  • the average value of the five measurements was taken 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 atmospheric reflow (maximum temperature 260°C) three times, 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)".
  • E1 Fluorine surfactant (“NBX-15” manufactured by NEOS Co., Ltd.)
  • E2 Cyclohexanone
  • F1 Benzotriazole
  • F3 3-glycidoxypropyltrimethoxysilane

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Abstract

Une composition de résine photosensible négative comprend : un polymère (A) ; un agent de réticulation (B) ; et un générateur de photo-cations (C), le polymère (A) ayant un motif constitutif représenté par la formule (a2) et ayant, au niveau d'une extrémité, un groupe réactif Y qui réagit avec l'agent de réticulation (B) grâce à l'action de cations générés par le générateur de photo-cations (C) par irradiation de lumière, et le générateur de photo-cations (C) comprenant un générateur de photo-cations (C1) qui génère, par irradiation de lumière, un acide ayant un pKa (1) d'au moins -3 et d'au plus 3 tel que calculé à l'aide d'une fonction gaussienne basée sur le pKa de l'acide méthanesulfonique dans une solution aqueuse à 25°C.
PCT/JP2023/019497 2022-06-30 2023-05-25 Composition de résine photosensible négative, procédé de production de film de résine à motif, film de résine à motif, et substrat de circuit semi-conducteur WO2024004462A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001147527A (ja) * 1999-11-19 2001-05-29 Nippon Kayaku Co Ltd 感光性樹脂組成物及びこれを用いた感光性フィルム
JP2015031724A (ja) * 2013-07-31 2015-02-16 日立化成株式会社 半導体装置の製造方法及びその製造方法によって得られる半導体装置
WO2020021827A1 (fr) * 2018-07-25 2020-01-30 Jsr株式会社 Composition de résine photosensible, procédé de production d'un film de résine à motifs, film de résine à motifs et substrat de circuit à semi-conducteurs
WO2021006181A1 (fr) * 2019-07-05 2021-01-14 富士フイルム株式会社 Composition photosensible thermodurcissable, film durci, corps multicouche, procédé de production de film durci et dispositif à semi-conducteur
WO2021039841A1 (fr) * 2019-08-27 2021-03-04 富士フイルム株式会社 Procédé de fabrication de film durci, composition de résine photodurcissable, procédé de fabrication de stratifié, et procédé de fabrication de dispositif à semi-conducteurs

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001147527A (ja) * 1999-11-19 2001-05-29 Nippon Kayaku Co Ltd 感光性樹脂組成物及びこれを用いた感光性フィルム
JP2015031724A (ja) * 2013-07-31 2015-02-16 日立化成株式会社 半導体装置の製造方法及びその製造方法によって得られる半導体装置
WO2020021827A1 (fr) * 2018-07-25 2020-01-30 Jsr株式会社 Composition de résine photosensible, procédé de production d'un film de résine à motifs, film de résine à motifs et substrat de circuit à semi-conducteurs
WO2021006181A1 (fr) * 2019-07-05 2021-01-14 富士フイルム株式会社 Composition photosensible thermodurcissable, film durci, corps multicouche, procédé de production de film durci et dispositif à semi-conducteur
WO2021039841A1 (fr) * 2019-08-27 2021-03-04 富士フイルム株式会社 Procédé de fabrication de film durci, composition de résine photodurcissable, procédé de fabrication de stratifié, et procédé de fabrication de dispositif à semi-conducteurs

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