WO2024204019A1 - 感光性樹脂組成物、硬化膜、電子装置および電子装置の製造方法 - Google Patents

感光性樹脂組成物、硬化膜、電子装置および電子装置の製造方法 Download PDF

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WO2024204019A1
WO2024204019A1 PCT/JP2024/011610 JP2024011610W WO2024204019A1 WO 2024204019 A1 WO2024204019 A1 WO 2024204019A1 JP 2024011610 W JP2024011610 W JP 2024011610W WO 2024204019 A1 WO2024204019 A1 WO 2024204019A1
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Prior art keywords
resin composition
photosensitive resin
group
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polyether
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English (en)
French (fr)
Japanese (ja)
Inventor
咲子 鈴木
竜二 広澤
誠 堀井
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Sumitomo Bakelite Co Ltd
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Sumitomo Bakelite Co Ltd
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Priority to EP24780137.6A priority Critical patent/EP4692940A1/en
Priority to JP2025510825A priority patent/JPWO2024204019A1/ja
Priority to CN202480021805.6A priority patent/CN121002446A/zh
Priority to KR1020257035786A priority patent/KR20250168502A/ko
Publication of WO2024204019A1 publication Critical patent/WO2024204019A1/ja
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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
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
    • C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/10—Block or graft copolymers containing polysiloxane sequences
    • C09D183/12—Block or graft copolymers containing polysiloxane sequences containing polyether sequences
    • 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
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • 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
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • 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
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
    • 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
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • 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
    • G03F7/16—Coating processes; 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
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences

Definitions

  • the present invention relates to a photosensitive resin composition, a cured film, an electronic device, and a method for manufacturing an electronic device.
  • a cured film obtained by exposing a photosensitive resin composition to light may be used as a permanent film that constitutes an electronic device.
  • An example of a technology related to such a photosensitive resin composition is described in Patent Document 1.
  • Patent Document 1 aims to provide a photosensitive resin composition that has excellent chemical resistance while maintaining high sensitivity, and describes a photosensitive resin composition that includes (A) a polymer component containing a polymer that satisfies at least one of the following (1) and (2): (1) a polymer having (a1) a structural unit having a residue in which an acid group is protected by an acid-decomposable group, and (a2) a structural unit having a crosslinkable group; (2) a polymer having (a1) a structural unit having a residue in which an acid group is protected by an acid-decomposable group, and (a2) a structural unit having a crosslinkable group; (B) a photoacid generator; (C) an aromatic heterocyclic compound; and (D) a solvent, wherein the aromatic heterocyclic compound (C) has a molecular weight of 1000 or less, contains at least one nitrogen atom in the aromatic ring, and contains at least two coordinating atoms in the aromatic ring.
  • a photosensitive resin composition that includes
  • the present invention provides a photosensitive resin composition with improved defoaming properties.
  • the present invention provides the following photosensitive resin composition, cured film, electronic device, and method for manufacturing an electronic device.
  • the composition comprises an alkali-soluble resin (A), a polyether-modified polydimethylsiloxane (B), a solvent (C), and a photosensitizer (D),
  • the photosensitive resin composition wherein the polyether-modified polydimethylsiloxane (B) has a weight average molecular weight (Mw) in terms of polystyrene, as measured by gel permeation chromatography, of 1,000 or more and 5,000 or less.
  • the solvent (C) contains a solvent (C1)
  • the photosensitive resin composition according to [2], wherein the content of the solvent (C1) in the solvent (C) is 50% by mass or more and 100% by mass or less with respect to the total amount of the solvent (C).
  • the present invention provides a photosensitive resin composition with improved defoaming properties.
  • FIG. 1 is a diagram showing an example of an electronic device including the photosensitive resin composition of the present embodiment.
  • the photosensitive resin composition of this embodiment contains an alkali-soluble resin (A), a polyether-modified polydimethylsiloxane (B), a solvent (C), and a photosensitizer (D), and the polyether-modified polydimethylsiloxane (B) has a polystyrene-equivalent weight average molecular weight (Mw) of 1,000 or more and 5,000 or less, as measured by gel permeation chromatography.
  • Mw polystyrene-equivalent weight average molecular weight
  • the weight average molecular weight (Mw) in terms of polystyrene, as measured by gel permeation chromatography is from the viewpoints of further improving the defoaming properties and further improving the affinity to aqueous solvents, 1000 or more, preferably 1200 or more, more preferably 1300 or more, and even more preferably 1400 or more, and from the viewpoint of further improving the defoaming properties, is from the viewpoints of further improving the defoaming properties, 5000 or less, preferably 4000 or less, more preferably 3000 or less, even more preferably 2500 or less, and even more preferably 2000 or less.
  • the weight average molecular weight (Mw) in terms of polystyrene, as measured by gel permeation chromatography is from 1,000 to 5,000, preferably from 1,200 to 4,000, more preferably from 1,300 to 3,000, even more preferably from 1,400 to 2,500, and even more preferably from 1,400 to 2,000, from the viewpoints of further improving the defoaming property and further improving the affinity for aqueous solvents.
  • the polyether-modified polydimethylsiloxane (B) may be used alone or in combination of two or more.
  • the weight average molecular weight (Mw) of one of the polyether-modified polydimethylsiloxanes (B) is within the above range, but it is preferable that the weighted average value of the weight average molecular weights (Mw) of the polyether-modified polydimethylsiloxanes (B) is within the above range.
  • the weight average molecular weight (Mw) of the polyether-modified polydimethylsiloxane (B) can be calculated using a molecular weight distribution curve obtained by GPC (Gel Permeation Chromatography).
  • the weight average molecular weight (Mw) of the polyether-modified polydimethylsiloxane (B) is calculated using a polystyrene-equivalent value obtained from a calibration curve of standard polystyrene (PS) obtained by GPC measurement.
  • PS standard polystyrene
  • the photosensitive resin composition of the present embodiment contains an alkali-soluble resin (A), a polyether-modified polydimethylsiloxane (B), a solvent (C), and a photosensitizer (D).
  • A alkali-soluble resin
  • B polyether-modified polydimethylsiloxane
  • C solvent
  • D photosensitizer
  • the weight average molecular weight (Mw) of the polyether-modified polydimethylsiloxane (B) is within the above range, the amount of fluorine-based surfactant used can be reduced, while the defoaming property of the photosensitive resin composition can be improved.
  • Mw weight average molecular weight
  • the polyether-modified polydimethylsiloxane (B) has a suitable weight average molecular weight (Mw) range, which improves the compatibility between the polyether-modified polydimethylsiloxane (B) and the solvent (C), thereby reducing the foam stability, thereby improving the defoaming property of the photosensitive resin composition.
  • the polyether-modified polydimethylsiloxane (B) has a polyether-modified group, which makes it moderately non-polar, which reduces the foam stability, thereby improving the defoaming property of the photosensitive resin composition.
  • the alkali-soluble resin (A) can be selected according to the physical properties such as mechanical properties and optical properties required for the resin film.
  • Specific examples of the alkali-soluble resin (A) include polyamide resins, polybenzoxazole resins, polyimide resins, phenolic resins, hydroxystyrene resins, and cyclic olefin resins, and one or more of these can be used in combination.
  • the alkali-soluble resin (A) preferably contains one or more selected from the group consisting of polyamide resins and polybenzoxazole resins, and more preferably contains polybenzoxazole resins, among the above specific examples.
  • the physical properties such as the mechanical strength of the cured film made of the photosensitive resin composition, the uniformity of the film thickness can be improved and the occurrence of defects can be further suppressed.
  • the polyamide resin preferably contains an aromatic polyamide containing an aromatic ring in the structural unit of the polyamide, and more preferably contains a structural unit represented by the following formula (PA1): This can further improve the physical properties such as mechanical strength of the cured film made of the photosensitive resin composition, thereby further improving the uniformity of the film thickness and further suppressing the occurrence of defects.
  • PA1 structural unit represented by the following formula
  • the aromatic ring refers to a benzene ring, a condensed aromatic ring such as a naphthalene ring, an anthracene ring, or a pyrene ring, or a heteroaromatic ring such as a pyridine ring or a pyrrole ring, etc.
  • the polyamide resin of this embodiment preferably contains a benzene ring as the aromatic ring.
  • the polyamide resin containing the structural unit represented by the above formula (PA1) is a precursor of polybenzoxazole resin.
  • the polyamide resin containing the structural unit represented by the above formula (PA1) can be dehydrated and ring-closed to form a polybenzoxazole resin by, for example, heat-treating it at a temperature of 150°C or higher and 420°C or lower for 30 minutes to 50 hours.
  • the structural unit of the above formula (PA1) becomes a structural unit represented by the following formula (PBO1) through dehydration and ring-closure.
  • the photosensitive resin composition may be subjected to the heat treatment to dehydrate and ring-close the polyamide resin to form a polybenzoxazole resin. That is, when a photosensitive resin composition containing a polyamide resin is subjected to the heat treatment, the photosensitive resin composition contains a polybenzoxazole resin.
  • the alkali-soluble resin (A) contains a polyamide resin containing a structural unit represented by the above formula (PA1)
  • a cured film described later may be produced, and then the heat treatment may be carried out to dehydrate and ring-close the polybenzoxazole resin.
  • the polyamide resin is dehydrated and ring-opened to form a polybenzoxazole resin, the mechanical properties and thermal properties can be further improved, and deformation of the cured film can be further suppressed.
  • polyamide resin polyimide resin
  • PA2 polyamide resin containing a structural unit represented by the following formula
  • PA2 is a precursor of a polyimide resin.
  • the polyamide resin containing a structural unit represented by the following formula (PA2) can be dehydrated and ring-closed to form a polyimide resin by, for example, heat-treating the polyamide resin at a temperature of 150° C. or higher and 420° C. or lower for 30 minutes to 50 hours.
  • the structural unit represented by the following formula (PA2) becomes a structural unit represented by the following formula (PI1) through dehydration and ring-closure.
  • the photosensitive resin composition may be subjected to the above-mentioned heat treatment to dehydrate and close the ring, thereby forming a polyimide resin. That is, the heat-treated photosensitive resin composition contains a polyimide resin that is the alkali-soluble resin (A).
  • the alkali-soluble resin (A) contains a polyamide resin containing a structural unit represented by the following formula (PA2)
  • PA2 polyamide resin containing a structural unit represented by the following formula
  • the resin after producing a resin film and an electronic device described later, the resin may be subjected to the above-mentioned heat treatment to dehydrate and ring-close the polyimide resin.
  • R 1 B and R 1 C preferably each independently represent an organic group having 1 to 30 carbon atoms.
  • R 1 B and R 1 C are the same as those in formula (PA2) above.
  • R 1 B and R 1 C in formula (PA2) and formula (PI1) are preferably an organic group having an aromatic ring.
  • the organic group having an aromatic ring is preferably one containing a benzene ring, a naphthalene ring or an anthracene ring, more preferably one containing a benzene ring, which can further improve the dispersibility of the alkali-soluble resin (A) and the defoaming property of the photosensitive resin composition.
  • the polyamide resin can be polymerized, for example, as follows. First, in the polymerization step (S1), a diamine monomer and a dicarboxylic acid monomer are polycondensed to polymerize a polyamide. Next, in the low molecular weight component removal step (S2), low molecular weight components are removed to obtain a polyamide resin mainly composed of polyamide.
  • Polymerization step (S1) In the polymerization step (S1), a diamine monomer and a dicarboxylic acid monomer are polycondensed.
  • the method of polycondensation for polymerizing polyamide is not limited, and specifically, melt polycondensation, acid chloride method, direct polymerization, etc. Condensation, etc.
  • a compound selected from the group consisting of tetracarboxylic dianhydride, trimellitic anhydride, dicarboxylic acid dichloride, and active ester type dicarboxylic acid may be used.
  • the method for obtaining the compound includes reacting a dicarboxylic acid with 1-hydroxy-1,2,3-benzotriazole or the like.
  • diamine monomer and dicarboxylic acid monomer used in the polymerization of the polyamide resin are described. Note that only one type of each of the diamine monomer and the dicarboxylic acid monomer may be used, or one or more types selected from the group consisting of two or more types of diamine monomers and two or more types of dicarboxylic acid monomers may be used.
  • diamine monomer used in the polymerization it is preferable to use a diamine monomer containing an aromatic ring in the structure, and it is more preferable to use a diamine monomer containing a phenolic hydroxyl group in the structure.
  • a polyamide resin By producing a polyamide resin using such a diamine monomer as a raw material, the conformation of the polyamide resin can be controlled, and the dispersibility of the alkali-soluble resin (A) in the photosensitive resin composition can be further improved.
  • the diamine monomer containing a phenolic hydroxyl group in the structure is preferably a diamine monomer represented by the following formula (DA1).
  • DA1 diamine monomer represented by the following formula (DA1)
  • PA3 structural unit represented by the following formula (PA3).
  • R4 is preferably a group formed by one or more atoms selected from the group consisting of a hydrogen atom, a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, a silicon atom, a chlorine atom, a fluorine atom and a bromine atom.
  • R5 to R10 each preferably independently represent a hydrogen atom or an organic group having from 1 to 30 carbon atoms.
  • R 5 to R 10 are the same as those in formula (DA1) above.
  • R4 in formula (DA1) and formula (PA3) is preferably a group formed by one or more atoms selected from the group consisting of a hydrogen atom, a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, a silicon atom, a chlorine atom, a fluorine atom, and a bromine atom.
  • R4 is preferably a divalent group.
  • the divalent group refers to the valence of an atom. That is, R4 has two bonds to other atoms.
  • R 4 in Formula (DA1) and Formula (PA3) contains a carbon atom
  • R 4 is preferably a group having 1 to 30 carbon atoms, more preferably a group having 1 to 10 carbon atoms, even more preferably a group having 1 to 5 carbon atoms, and still more preferably a group having 1 to 3 carbon atoms.
  • R 4 in formula (DA1) and formula (PA3) contains a carbon atom
  • specific examples of R 4 include an alkylene group, an arylene group, a halogen-substituted alkylene group, and a halogen-substituted arylene group.
  • the alkylene group may be, for example, a straight-chain alkylene group or a branched-chain alkylene group.
  • straight-chain alkylene group examples include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, a decanylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group.
  • branched alkylene groups include alkylmethylene groups such as -C( CH3 ) 2- , -CH( CH3 )-, -CH(CH2CH3)-, -C (CH3 ) ( CH2CH3 )-, -C ( CH3 ) ( CH2CH2CH3 )-, and -C( CH2CH3 ) 2- ; and alkylethylene groups such as -CH( CH3 ) CH2- , -CH( CH3 ) CH ( CH3 ) -, -C ( CH3 ) 2CH2- , -CH( CH2CH3 ) CH2- , and -C( CH2CH3 ) 2 - CH2- .
  • the arylene group examples include a phenylene group, a biphenylene group, a naphthylene group, an anthrylene group, and groups in which two or more arylene groups are bonded to each other.
  • the halogen-substituted alkylene group and the halogen-substituted arylene group those in which the hydrogen atom in the above-mentioned alkylene group and arylene group is replaced with a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom can be preferably used. Among these, those in which the hydrogen atom is replaced with a fluorine atom are preferred.
  • R 4 in formula (DA1) and formula (PA3) does not contain a carbon atom
  • specific examples of R 4 include groups containing an oxygen atom or a sulfur atom.
  • R 5 to R 10 in formula (DA1) and formula (PA3) are preferably each independently hydrogen or an organic group having 1 to 30 carbon atoms, preferably hydrogen or an organic group having 1 to 10 carbon atoms, more preferably hydrogen or an organic group having 1 to 5 carbon atoms, even more preferably hydrogen or an organic group having 1 to 3 carbon atoms, and even more preferably hydrogen or an organic group having 1 to 2 carbon atoms.
  • This allows aromatic rings of the polyamide resin to be closely arranged. Therefore, the molecules of the alkali-soluble resin (A) and the metal molecules are more strongly bound to each other in a coordinated manner, and the molecular structure can be frozen, thereby further improving the adhesion.
  • organic group having 1 to 30 carbon atoms for R 5 to R 10 in Formula (DA1) and Formula (PA3) include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, and decyl group; alkenyl groups such as allyl group, pentenyl group, and vinyl group; alkynyl groups such as ethynyl group; alkylidene groups such as methylidene group and ethylidene group; aryl groups such as tolyl group, xylyl group, phenyl group, naphthyl group, and anthracenyl group; aralkyl groups such as methyl group,
  • diamine monomer represented by formula (DA1) it is preferable to use one or more selected from the group consisting of 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, 4,4'-methylenebis(2-amino-3,6 dimethylphenol), 4,4'-methylenebis(2-aminophenol), 1,1-bis(3-amino-4-hydroxyphenyl)ethane and 3,3'-diamino-4,4'-dihydroxydiphenyl ether.
  • the aromatic rings of the polyamide resin can be arranged closely together.
  • the molecular structure can be frozen with a coordination in which the molecules of the alkali-soluble resin (A) and the metal molecules are more strongly bound, and the adhesion can be further improved.
  • the diamine monomer one or two or more of the above specific examples can be used in combination. The structural formulae of these diamine monomers are shown below.
  • dicarboxylic acid monomer As the dicarboxylic acid monomer used in the polymerization, it is preferable to use a dicarboxylic acid monomer containing an aromatic ring in the structure. As the dicarboxylic acid monomer containing an aromatic ring, it is preferable to use one represented by the following formula (DC1).
  • DC1 Dicarboxylic acid monomer
  • By producing a polyamide resin using such a dicarboxylic acid monomer as a raw material it is possible to control the conformation of the polyamide resin and further improve the dispersibility of the alkali-soluble resin (A) in the mixed solvent. And, by improving the dispersibility of the alkali-soluble resin (A), it is possible to further improve the defoaming property of the photosensitive resin composition.
  • R 11 is preferably a group formed by one or more atoms selected from the group consisting of a hydrogen atom, a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, a silicon atom, a chlorine atom, a fluorine atom, and a bromine atom.
  • R 12 to R 19 each preferably independently represent a hydrogen atom or an organic group having 1 to 30 carbon atoms.
  • the polyamide resin typically contains a structural unit represented by the following formula (PA4):
  • PA4 the definitions of R 11 and R 12 to R 19 are the same as those in formula (DC1).
  • R 11 in formula (DC1) and formula (PA4) is preferably a group formed by one or more atoms selected from the group consisting of a hydrogen atom, a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, a silicon atom, a chlorine atom, a fluorine atom, and a bromine atom.
  • R 11 is preferably a divalent group.
  • the term "divalent group” refers to the valence of an atom. In other words, R 11 has two bonds to other atoms.
  • R 11 in Formula (DC1) and Formula (PA4) contains a carbon atom
  • R 11 is preferably a group having 1 to 30 carbon atoms, more preferably a group having 1 to 10 carbon atoms, even more preferably a group having 1 to 5 carbon atoms, and still more preferably a group having 1 to 3 carbon atoms.
  • R 11 in formula (DC1) and formula (PA4) contains a carbon atom
  • specific examples of R 11 include an alkylene group, an arylene group, a halogen-substituted alkylene group, and a halogen-substituted arylene group.
  • the alkylene group may be, for example, a straight-chain alkylene group or a branched-chain alkylene group.
  • straight-chain alkylene group examples include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, a decanylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group.
  • branched alkylene groups include alkylmethylene groups such as -C( CH3 ) 2- , -CH( CH3 )-, -CH(CH2CH3)-, -C (CH3 ) ( CH2CH3 )-, -C ( CH3 ) ( CH2CH2CH3 )-, and -C( CH2CH3 ) 2- ; and alkylethylene groups such as -CH( CH3 ) CH2- , -CH( CH3 ) CH ( CH3 ) -, -C ( CH3 ) 2CH2- , -CH( CH2CH3 ) CH2- , and -C( CH2CH3 ) 2 - CH2- .
  • the arylene group include a phenylene group, a biphenylene group, a naphthylene group, an anthrylene group, and groups in which two or more arylene groups are bonded to each other.
  • the halogen-substituted alkylene group and the halogen-substituted arylene group may be the above-mentioned alkylene group and arylene group in which a hydrogen atom is replaced with a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom.
  • a hydrogen atom such as a fluorine atom, a chlorine atom, or a bromine atom.
  • R 11 in formula (DC1) and formula (PA4) does not contain a carbon atom
  • specific examples of R 11 include groups containing an oxygen atom or a sulfur atom.
  • R 12 to R 19 are preferably each independently hydrogen or an organic group having 1 to 30 carbon atoms, more preferably hydrogen or an organic group having 1 to 10 carbon atoms, even more preferably hydrogen or an organic group having 1 to 5 carbon atoms, even more preferably hydrogen or an organic group having 1 to 3 carbon atoms, and even more preferably hydrogen.
  • organic group having 1 to 30 carbon atoms for R 12 to R 19 in formula (DC1) and formula (PA4) include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group; alkenyl groups such as an allyl group, a pentenyl group, and a vinyl group; alkynyl groups such as an ethynyl group; alkylidene groups such as a methylidene group and an ethylidene group; aryl groups such as a tolyl group, a
  • dicarboxylic acid monomer examples include diphenyl ether 4,4'-dicarboxylic acid, isophthalic acid, terephthalic acid, and 4,4'-biphenyl dicarboxylic acid.
  • diphenyl ether 4,4'-dicarboxylic acid or isophthalic acid isophthalic acid
  • diphenyl ether 4,4'-dicarboxylic acid isophthalic acid
  • diphenyl ether 4,4'-dicarboxylic acid This allows the aromatic rings of the polyamide resin to be closely arranged. Therefore, the molecular structure can be frozen in a coordination in which the molecules of the alkali-soluble resin (A) and the metal molecules are more strongly bound, and adhesion can be further improved.
  • the polyamide resin has a terminal amino group modified with a specific acid anhydride or a specific monocarboxylic acid.
  • the specific acid anhydride and the specific monocarboxylic acid have one or more functional groups selected from the group consisting of an alkenyl group, an alkynyl group, and a hydroxyl group.
  • the specific acid anhydride and the specific monocarboxylic acid preferably contain, for example, a nitrogen atom. This can further improve the wettability of the photosensitive resin composition with metal after post-baking.
  • specific acid anhydrides include maleic anhydride, citraconic anhydride, 2,3-dimethylmaleic anhydride, 4-cyclohexene-1,2-dicarboxylic anhydride, exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride, 5-norbornene-2,3-dicarboxylic anhydride, methyl-5-norbornene-2,3-dicarboxylic anhydride, itaconic anhydride, HET anhydride, 4-ethynylphthalic anhydride, 4-phenylethynylphthalic anhydride, and 4-hydroxyphthalic anhydride.
  • the specific acid anhydrides may be one or a combination of two or more of the above specific examples.
  • the specific ring-shaped acid anhydride is opened.
  • the structural unit derived from the specific ring-shaped acid anhydride may be ring-closed to form an imide ring.
  • a method for ring-closing may be heat treatment.
  • the specific monocarboxylic acid include 5-norbornene-2-carboxylic acid, 4-hydroxybenzoic acid, 3-hydroxybenzoic acid, etc.
  • the specific monocarboxylic acid one or a combination of two or more of the specific examples can be used.
  • the carboxyl group present at the terminal of the polyamide resin may be modified simultaneously with or after the polymerization step (S1).
  • the modification can be carried out, for example, by reacting a dicarboxylic acid monomer or a polyamide resin with a specific nitrogen atom-containing heteroaromatic compound. Therefore, it is preferable that the polyamide resin has a terminal carboxyl group modified with a specific nitrogen atom-containing heteroaromatic compound.
  • the specific nitrogen atom-containing heteroaromatic compound has one or more functional groups selected from the group consisting of 1-(5-1H-triazoyl)methylamino group, 3-(1H-pyrazoyl)amino group, 4-(1H-pyrazoyl)amino group, 5-(1H-pyrazoyl)amino group, 1-(3-1H-pyrazoyl)methylamino group, 1-(4-1H-pyrazoyl)methylamino group, 1-(5-1H-pyrazoyl)methylamino group, (1H-tetrazol-5-yl)amino group, 1-(1H-tetrazol-5-yl)methyl-amino group and 3-(1H-tetrazol-5-yl)benz-amino group.
  • Low molecular weight component removal step (S2) Following the polymerization step (S1), it is preferable to carry out a low molecular weight component removal step (S2) to remove the low molecular weight components.
  • the organic layer containing the mixture of low molecular weight components and polyamide resin is concentrated by filtration or the like, and then redissolved in an organic solvent such as water/isopropanol. This allows the precipitate to be filtered off. As a result, a polyamide resin from which low molecular weight components have been removed can be obtained.
  • a photosensitive resin composition in the form of a varnish without going through a process in which the solvent is completely evaporated and the composition becomes dry after the low molecular weight component removal process. This makes it possible to further suppress the decrease in dispersibility of the alkali-soluble resin (A) due to interactions between the polyamide resin molecules resulting from amide bonds. Therefore, the defoaming properties of the photosensitive resin composition can be further improved.
  • phenolic resin examples include novolac-type phenolic resins such as phenol novolac resin, cresol novolac resin, bisphenol novolac resin, and phenol-biphenyl novolac resin; reaction products of phenolic compounds such as novolac-type phenolic resin, resol-type phenolic resin, and cresol novolac resin with aldehyde compounds; reaction products of phenolic compounds such as phenol aralkyl resin with dimethanol compounds, etc.
  • the phenolic resin may contain one or more of the above specific examples.
  • the phenol compound used in the above-mentioned reaction product of a phenol compound and an aldehyde compound or the reaction product of a phenol compound and a dimethanol compound is not limited.
  • phenolic compounds include cresols such as phenol, o-cresol, m-cresol, and p-cresol; xylenols such as 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, and 3,5-xylenol; ethylphenols such as o-ethylphenol, m-ethylphenol, and p-ethylphenol; alkylphenols such as isopropylphenol, butylphenol, and p-tert-butylphenol; polyhydric phenols such as resorcinol, catechol, hydroquinone, pyrogallol, and
  • the aldehyde compound used in the reaction product of the phenol compound and the aldehyde compound is not limited as long as it is a compound having an aldehyde group.
  • Specific examples of such aldehyde compounds include formaldehyde, paraformaldehyde, acetaldehyde, benzaldehyde, salicylaldehyde, etc.
  • the aldehyde compound one or more of the above specific examples can be used.
  • the dimethanol compound used in the reaction product of the phenol compound and the dimethanol compound is not limited.
  • specific examples of such dimethanol compounds include dimethanol compounds such as 1,4-benzenedimethanol, 1,3-benzenedimethanol, 4,4'-biphenyldimethanol, 3,4'-biphenyldimethanol, 3,3'-biphenyldimethanol, 2,6-naphthalenedimethanol, and 2,6-bis(hydroxymethyl)-p-cresol; and bis(alkoxymethyl) compounds such as 1,4-bis(methoxymethyl)benzene, 1,3-bis(methoxymethyl)benzene, 4,4'-bis(methoxymethyl)biphenyl, 3,4'-bis(methoxymethyl)biphenyl, 3,3'-bis(methoxymethyl)biphenyl, and methyl 2,6-naphthalenedicarboxylate.
  • halogenoalkyl compounds such as 1,4-bis(chloromethyl)benzene, 1,3-bis(chloromethyl)benzene, 1,4-bis(bromomethyl)benzene, 1,3-bis(bromomethyl)benzene, 4,4'-bis(chloromethyl)biphenyl, 3,4'-bis(chloromethyl)biphenyl, 3,3'-bis(chloromethyl)biphenyl, 4,4'-bis(bromomethyl)biphenyl, 3,4'-bis(bromomethyl)biphenyl or 3,3'-bis(bromomethyl)biphenyl, and biphenyl aralkyl compounds such as 4,4'-bis(methoxymethyl)biphenyl and 4,4'-bis(methoxymethyl)biphenyl.
  • the dimethanol compound one or more of the above specific examples can be used.
  • the hydroxystyrene resin is not limited, and specifically, a polymerization or copolymerization product obtained by polymerizing or copolymerizing one or more selected from the group consisting of hydroxystyrene, hydroxystyrene derivatives, styrene, and styrene derivatives can be used.
  • Specific examples of the hydroxystyrene derivatives and styrene derivatives include those in which hydrogen atoms in the aromatic ring of hydroxystyrene or styrene are substituted with monovalent organic groups.
  • Examples of the monovalent organic groups substituting hydrogen atoms include alkyl groups such as methyl, ethyl, and n-propyl groups; alkenyl groups such as allyl and vinyl groups; alkynyl groups such as ethynyl groups; alkylidene groups such as methylidene and ethylidene groups; cycloalkyl groups such as cyclopropyl groups; and heterocyclic groups such as epoxy and oxetanyl groups.
  • the cyclic olefin resin is not limited, and specifically, a polymerization or copolymerization product obtained by polymerizing or copolymerizing one or more types selected from the group consisting of norbornene and norbornene derivatives can be used.
  • norbornene derivatives include norbornadiene, bicyclo[2.2.1]-hept-2-ene (common name: 2-norbornene), 5-methyl-2-norbornene, 5-ethyl-2-norbornene, 5-butyl-2-norbornene, 5-hexyl-2-norbornene, 5-decyl-2-norbornene, 5-allyl-2-norbornene, 5-(2-propenyl)-2-norbornene, 5-(1-methyl-4-pentenyl)-2-norbornene, 5-ethynyl-2-norbornene, 5-benzyl-2-norbornene, 5-phenethyl-2-norbornene, 2-acetyl-5-norbornene, methyl 5-norbornene-2-carboxylate, and 5-norbornene-2,3-dicarboxylic anhydride.
  • 2-norbornene commonly name: 2-norbornene
  • the lower limit of the content of the alkali-soluble resin (A) in the photosensitive resin composition is preferably 30 parts by mass or more, more preferably 40 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 60 parts by mass or more, and even more preferably 70 parts by mass or more, when the total solid content of the photosensitive resin composition is 100 parts by mass. This can further improve the dispersibility of the alkali-soluble resin (A) in the photosensitive resin composition and further improve the defoaming property of the photosensitive resin composition.
  • the upper limit of the content of the alkali-soluble resin (A) in the photosensitive resin composition is preferably 95 parts by mass or less, more preferably 90 parts by mass or less, and even more preferably 85 parts by mass or less, based on 100 parts by mass of the total solid content of the photosensitive resin composition.
  • the total solid content of the photosensitive resin composition refers to the total of the components contained in the photosensitive resin composition excluding the solvent.
  • the weight average molecular weight (Mw) of the alkali-soluble resin (A) is preferably 5,000 or more, more preferably 6,000 or more, even more preferably 7,000 or more, and is preferably 70,000 or less, more preferably 65,000 or less, even more preferably 60,000 or less.
  • the weight average molecular weight (Mw) of the alkali-soluble resin (A) is preferably 5,000 or more and 70,000 or less, more preferably 6,000 or more and 65,000 or less, and even more preferably 7,000 or more and 60,000 or less, from the viewpoint of further improving the dispersibility of the alkali-soluble resin (A) in the photosensitive resin composition.
  • polyether-modified polydimethylsiloxane (B) The polyether-modified polydimethylsiloxane (B) of the present embodiment preferably contains a polyether-modified polydimethylsiloxane represented by the following general formula (1), which can further improve the defoaming property during production of the photosensitive resin composition.
  • the polyether-modified polydimethylsiloxane (B) represented by the following general formula (1) has a polydimethylsiloxane chain, which is the main chain, that has a helical structure, and the dimethyl groups and polyether-modified groups, which are side chains, are arranged on the surface side of the helical structure, so that there is an advantage in that the properties of the polyether-modified polydimethylsiloxane (B) can be further controlled by the side chain structure.
  • m is preferably an average value of 1 or more and 5 or less
  • p is preferably an average value of 1 or more and 10 or less
  • q is preferably an average value of 0 or more and less than 1.
  • R preferably represents hydrogen or an alkyl group having 1 to 5 carbon atoms.
  • x is preferably 1 or more, more preferably 2 or more, on average, and is preferably 50 or less, more preferably 40 or less.
  • x in the general formula (1) is preferably 1 or more and 50 or less, and more preferably 2 or more and 40 or less.
  • y is preferably 1 or more, more preferably 2 or more, on average, and is preferably 10 or less, more preferably 8 or less, and further preferably 6 or less.
  • y is preferably 1 or more and 10 or less, more preferably 2 or more and 8 or less, and further preferably 2 or more and 6 or less.
  • the ratio of x to y (x/y) is preferably 1 or more, more preferably 1.2 or more, and is preferably 5 or less, more preferably 4 or less.
  • the ratio of x to y (x/y) is preferably 1 or more and 5 or less, and more preferably 1.2 or more and 4 or less.
  • the compatibility of the polyether-modified polydimethylsiloxane (B), the alkali-soluble resin (A), the solvent (C), and the photosensitizer (D) is improved.
  • the more polar (hydrophilic) the polyether modified group is the more stable the foam is, and the lower the defoaming property.
  • the less polar (hydrophobic) the polyether modified group is the lower the foam stability is, and the higher the defoaming property is.
  • m is preferably 1 or more, more preferably 2 or more, and is preferably 5 or less, more preferably 4 or less, on average.
  • m in the general formula (1) is preferably 1 or more and 5 or less, and more preferably 2 or more and 4 or less.
  • p is an average value that is preferably 1 or more, more preferably 3 or more, even more preferably 4 or more, and even more preferably 5 or more, and is preferably 10 or less, more preferably 9 or less.
  • p is an average value and is preferably 1 or more and 10 or less, more preferably 3 or more and 10 or less, further preferably 4 or more and 9 or less, and further preferably 5 or more and 9 or less.
  • q is an average value and is preferably equal to or greater than 0 and less than 1.
  • R preferably represents hydrogen or an alkyl group having 1 to 5 carbon atoms, more preferably hydrogen or a methyl group, and further preferably hydrogen.
  • the polyether-modified polydimethylsiloxane (B) becomes appropriately highly polar (hydrophilic), and thus the polyether-modified polydimethylsiloxane (B) can be dissolved in an aqueous solvent.
  • the polyether-modified polydimethylsiloxane (B) can be synthesized from a polyether compound and polydimethylsiloxane.
  • m, p, q, x, and y in the general formula (1) can be adjusted by adjusting the type and mixing ratio of the polyether compound and polydimethylsiloxane used.
  • the m, p, q, x, and y in the general formula (1) can be determined from the structures of the polyether compound and polydimethylsiloxane used in the synthesis of the polyether-modified polydimethylsiloxane (B).
  • m, p, q, x, and y in the general formula (1) can also be identified by known polymer structure analysis methods such as NMR, IR, pyrolysis GC-MS, TOF-SIMS, and LC-TOF/MS.
  • the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn) (Mw/Mn) of the polyether-modified polydimethylsiloxane (B) is preferably 1 or more, more preferably 2 or more, and is preferably 10 or less, more preferably 8 or less, even more preferably 7 or less, even more preferably 6 or less, even more preferably 4 or less, and even more preferably 3 or less.
  • the ratio (Mw/Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the polyether-modified polydimethylsiloxane (B) is preferably 1 or more and 10 or less, more preferably 1 or more and 8 or less, even more preferably 1 or more and 7 or less, even more preferably 2 or more and 6 or less, even more preferably 2 or more and 4 or less, and even more preferably 2 or more and 3 or less, from the viewpoint of further improving the defoaming property of the photosensitive resin composition.
  • the weight average molecular weight of the maximum peak of the molecular weight distribution of the polyether-modified polydimethylsiloxane (B) measured by gel permeation chromatography in terms of polystyrene is preferably 1,000 or more, more preferably 1,300 or more, and even more preferably 1,800 or more, and is preferably 5,000 or less, more preferably 4,000 or less.
  • the weight average molecular weight of the polyether-modified polydimethylsiloxane (B) at the maximum peak of the molecular weight distribution in terms of polystyrene measured by gel permeation chromatography is preferably 1,000 or more and 5,000 or less, more preferably 1,300 or more and 5,000 or less, and even more preferably 1,800 or more and 4,000 or less.
  • the defoaming properties of the photosensitive resin composition are further improved. Also, when the weight average molecular weight of the maximum peak of the polyether-modified polydimethylsiloxane (B) is equal to or less than the above upper limit, the compatibility with ⁇ -butyrolactone described below is improved, and the defoaming properties of the photosensitive resin composition are further improved.
  • the number average molecular weight (Mn) and the weight average molecular weight of the maximum peak of the polyether-modified polydimethylsiloxane (B) are the same as the weight average molecular weight (Mw) of the polyether-modified polydimethylsiloxane (B) described above, and are measured by gel permeation chromatography (GPC) and calculated in terms of polystyrene.
  • the weight average molecular weight of the maximum peak of the polyether-modified polydimethylsiloxane (B) can be calculated by peak separation of the chromatography obtained by gel permeation chromatography (GPC).
  • the peak separation software for example, Eco-SEC manufactured by Tosoh Corporation can be used.
  • the maximum peak refers to the peak with the maximum integrated value.
  • the surface tension (mN/m) of the polyether-modified polydimethylsiloxane (B) is preferably 20 mN/m or more, more preferably 25 mN/m or more, even more preferably 27 mN/m or more, and is preferably 40 mN/m or less, more preferably 35 mN/m or less, even more preferably 30 mN/m or less.
  • the surface tension (mN/m) of the polyether-modified polydimethylsiloxane (B) is measured using a contact angle meter at 23° C. in a 1% GBL solution. As the contact angle meter, a DMs-401 (Kyowa Interface Science Co., Ltd.) can be used.
  • the density (g/mL) of the polyether-modified polydimethylsiloxane (B), measured at 20° C. in accordance with ISO 2811-3:2011, is preferably 0.90 g/mL or more, more preferably 0.95 g/mL or more, and is preferably 1.15 g/mL or less, more preferably 1.10 g/mL or less, from the viewpoint of containing as little low molecular weight components as possible.
  • the refractive index of the polyether-modified polydimethylsiloxane (B), as measured in accordance with DIN 51423, is preferably 1.30 or more, more preferably 1.40 or more, and is preferably 1.60 or less, more preferably 1.50 or less, from the viewpoint of containing as little low molecular weight components as possible.
  • the non-volatile content of the polyether-modified polydimethylsiloxane (B), as measured in accordance with ISO 3251:2019 under heating conditions at 105°C for 1 hour, is preferably 85.0% or more, more preferably 87.0% or more, and even more preferably 90.0% or more, from the viewpoint of containing as little low molecular weight components as possible.
  • the content of the polyether-modified polydimethylsiloxane (B) is preferably 10 ppm or more, more preferably 50 ppm or more, and even more preferably 90 ppm or more, and is preferably 3000 ppm or less, more preferably 2500 ppm or less, even more preferably 2000 ppm or less, and even more preferably 1600 ppm or less, based on the entire photosensitive resin composition.
  • the content of the polyether-modified polydimethylsiloxane (B) is preferably 10 ppm or more and 3000 ppm or less, more preferably 10 ppm or more and 2500 ppm or less, even more preferably 50 ppm or more and 2000 ppm or less, and still more preferably 90 ppm or more and 1600 ppm or less, based on the entire photosensitive resin composition.
  • the content of the polyether-modified polydimethylsiloxane (B) is within the above range, the defoaming property of the photosensitive resin composition can be further improved.
  • the solvent (C) preferably contains the following solvent (C1).
  • the solvent (C1) preferably contains at least one selected from the group consisting of ⁇ -butyrolactone (GBL), N-methyl-2-pyrrolidone (NMP), N-ethyl-2-pyrrolidone (NEP), propylene glycol monomethyl ether (PGME), 3-methyl-2-oxazolidinone, 3-methoxy-N,N-dimethylpropanamide, and propylene glycol monomethyl ether acetate (PGMEA).
  • GBL ⁇ -butyrolactone
  • NMP N-methyl-2-pyrrolidone
  • NEP N-ethyl-2-pyrrolidone
  • PGME propylene glycol monomethyl ether
  • 3-methyl-2-oxazolidinone 3-methoxy-N,N-dimethylpropanamide
  • PGMEA propylene glycol monomethyl ether acetate
  • the photosensitive resin composition it more preferably contains one selected from the group consisting of ⁇ -butyrolactone (GBL), N-methyl-2-pyrrolidone (NMP), N-ethyl-2-pyrrolidone (NEP), and 3-methyl-2-oxazolidinone, and further preferably contains ⁇ -butyrolactone.
  • GBL ⁇ -butyrolactone
  • NMP N-methyl-2-pyrrolidone
  • NEP N-ethyl-2-pyrrolidone
  • 3-methyl-2-oxazolidinone 3-methyl-2-oxazolidinone
  • ⁇ -butyrolactone has good compatibility with the above-mentioned polyether-modified polydimethylsiloxane (B) in that it can make the surface tension of the entire photosensitive resin composition more appropriate and can make the polarity of the polyether-modified polydimethylsiloxane (B) in the photosensitive resin composition more appropriate, and therefore the defoaming property of the photosensitive resin composition can be further improved.
  • Solvent (C) may contain other solvents in addition to solvent (C1).
  • other solvents include urea-based solvents such as N,N-dimethylacetamide, tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidinone, tetrabutylurea, N,N'-dimethylpropyleneurea, 1,3-dimethoxy-1,3-dimethylurea, N,N'-diisopropyl-O-methylisourea, O,N,N'-triisopropylisourea, O-tert-butyl-N,N'-diisopropylisourea, O-ethyl-N,N'-diisopropylisourea, and O-benzyl-N,N'-diisopropylisourea; tetrahydrofurfuryl alcohol.
  • TNU tetramethylurea
  • suitable solvents include alcohol-based solvents such as benzyl alcohol, 2-ethylhexanol, butanediol, and isopropyl alcohol; ketone-based solvents such as cyclopentanone, cyclohexanone, diacetone alcohol, and 2-heptanone; carbonate-based solvents such as ethylene carbonate and propylene carbonate; sulfone-based solvents such as dimethyl sulfoxide (DMSO) and sulfolane; ester-based solvents such as methyl pyruvate, ethyl pyruvate, and methyl-3-methoxypropionate; and aromatic hydrocarbon-based solvents such as mesitylene, toluene, and xylene.
  • the solvents may be one or a combination of two or more of the above specific examples.
  • the content of the solvent (C1) is preferably 50 mass % or more, more preferably 60 mass % or more, even more preferably 70 mass % or more, even more preferably 80 mass % or more, even more preferably 90 mass % or more, and is preferably 100 mass % or less, based on the total amount of the solvent (C).
  • the content of the solvent (C1) is preferably from 50% by mass to 100% by mass, more preferably from 60% by mass to 100% by mass, even more preferably from 70% by mass to 100% by mass, even more preferably from 80% by mass to 100% by mass, and even more preferably from 90% by mass to 100% by mass, based on the entire solvent (C).
  • the content of the solvent (C) is preferably 40% by mass or more, more preferably 50% by mass or more, and is preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less, when the entire photosensitive resin composition is taken as 100% by mass.
  • Photosensitizer (D) As the photosensitizer (D), a photoacid generator that generates an acid by absorbing light energy can be used. Specific examples of the photoacid generator include diazoquinone compounds, diaryliodonium salts, 2-nitrobenzyl ester compounds, N-iminosulfonate compounds, imidosulfonate compounds, 2,6-bis(trichloromethyl)-1,3,5-triazine compounds, and dihydropyridine compounds. Among these, the photosensitizer (D) preferably contains a photosensitive diazoquinone compound. This can further improve the sensitivity of the photosensitive resin composition. Therefore, the accuracy of the pattern can be improved, and the appearance can be further improved.
  • the photoacid generator can contain one or more of the above specific examples.
  • a triarylsulfonium salt, a sulfonium borate salt, or other onium salt may be used as the photosensitizer (D) in combination with the above specific examples, thereby further improving the sensitivity of the photosensitive resin composition.
  • Q is a structure represented by the following formula (a), (b), or (c), or a hydrogen atom, with the proviso that at least one of Q in each diazoquinone compound is a structure represented by the following formula (a), (b), or (c).
  • Q of the diazoquinone compound preferably contains the following formula (a) or the following formula (b). This can further improve the transparency of the photosensitive resin composition. Therefore, the appearance of the photosensitive resin composition can be further improved.
  • the lower limit of the content of the photosensitizer (D) in the photosensitive resin composition is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and still more preferably 10 parts by mass or more, based on 100 parts by mass of the alkali-soluble resin (A). This allows the photosensitive resin composition to exhibit appropriate sensitivity.
  • the upper limit of the content of the photosensitizer (D) in the photosensitive resin composition is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, per 100 parts by mass of the alkali-soluble resin (A), which makes it possible to prevent the photosensitive resin composition from being repelled by a metal material present on the surface of the substrate of the semiconductor device.
  • the photosensitive resin composition according to this embodiment may further contain an adhesion assistant (E).
  • the adhesion aid (E) preferably contains one selected from the group consisting of a triazole compound, an aminosilane, an imide compound, an epoxysilane, a (meth)acrylic silane, and a reaction product of an epoxy compound and an aminotriazole, which can further improve the affinity between the photosensitive resin composition and the metal member.
  • triazole compounds include 4-amino-1,2,4-triazole, 4H-1,2,4-triazole-3-amine, 4-amino-3,5-di-2-pyridyl-4H-1,2,4-triazole, 3-amino-5-methyl-4H-1,2,4-triazole, 4-methyl-4H-1,2,4-triazole-3-amine, 3,4-diamino-4H-1,2,4-triazole, 3,5-diamino-4H-
  • 1,2,4-triazoles include 1,2,4-triazole, 1,2,4-triazole-3,4,5-triamine, 3-pyridyl-4H-1,2,4-triazole, 4H-1,2,4-triazole-3-carboxamide, 3,5-diamino-4-methyl-1,2,4-triazole, 3-pyridyl-4-methyl-1,2,4-triazole, and 4-methyl-1,2,4-triazole-3-carboxamide.
  • the triazole compound one or
  • aminosilanes include condensates of cyclohexene-1,2-dicarboxylic anhydride and 3-aminopropyltriethoxysilane, condensates of 3,3',4,4'-benzophenonetetracarboxylic dianhydride and 3-aminopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane
  • imide compounds examples include the compounds listed below. These can be used alone or in combination of two or more.
  • epoxy silanes include 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, etc.
  • one or a combination of two or more types of epoxy silanes can be used.
  • (meth)acrylic silanes include 3-(meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, etc.
  • As the (meth)acrylic silane one or a combination of two or more of the above specific examples can be used.
  • Examples of the epoxy compound and aminotriazole used in the reaction product of the epoxy compound and aminotriazole include the following.
  • the epoxy compound is not limited as long as it contains an epoxy group, and examples of the epoxy group-containing compound include bisphenol A type epoxy resin, bisphenol F type epoxy resin, naphthalene type epoxy resin, biphenyl type epoxy resin, phenol novolac resin type epoxy resin, etc.
  • Examples of the aminotriazole include 3-amino-1,2,4-triazole and 4-amino-1,2,4-triazole.
  • the content of the adhesion assistant (E) in the photosensitive resin composition is preferably 0 part by mass or more, more preferably 1.0 part by mass or more, even more preferably 2.0 parts by mass or more, even more preferably 3.0 parts by mass or more, and is preferably 15 parts by mass or less, more preferably 13 parts by mass or less, even more preferably 12 parts by mass or less, based on 100 parts by mass of the alkali-soluble resin (A).
  • the dispersibility of the adhesion aid (E) in the photosensitive resin composition is improved, and the adhesion of the photosensitive resin composition to an adherend can be further improved, thereby making it possible to further suppress the intrusion of foreign matter between the resin film and the adherend to which the resin film is adhered.
  • the total content of the alkali-soluble resin (A), polyether-modified polydimethylsiloxane (B), solvent (C) and photosensitizer (D) is preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, and even more preferably 90% by mass or more, when the entire photosensitive resin composition is taken as 100% by mass, from the viewpoint of further improving the defoaming properties of the photosensitive resin composition and further improving the coatability of the photosensitive resin composition, and may be, for example, 100% by mass or less, or 99% by mass or less.
  • the total content of the alkali-soluble resin (A) and the polyether-modified polydimethylsiloxane (B) is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, and is preferably 50% by mass or less, more preferably 45% by mass or less, even more preferably 40% by mass or less, when the entire photosensitive resin composition is taken as 100% by mass, from the viewpoint of further improving the defoaming property of the photosensitive resin composition and further improving the performance balance of the mechanical properties and coatability of the photosensitive resin composition.
  • the photosensitive resin composition according to this embodiment may further contain additives such as a thermal crosslinking agent, an antioxidant, a dissolution promoter, a filler, and a sensitizer.
  • additives such as a thermal crosslinking agent, an antioxidant, a dissolution promoter, a filler, and a sensitizer.
  • the photosensitive resin composition according to this embodiment may further contain a thermal crosslinking agent, which can further improve the mechanical properties of the cured product of the photosensitive resin composition.
  • a thermal crosslinking agent examples include compounds having a methylol group, phenols, compounds having an alkoxymethyl group, methylol melamine compounds, alkoxy melamine compounds, alkoxy methyl glycoluril compounds, methylol urea compounds, cyano compounds, isocyanate compounds, epoxy group-containing compounds, maleimide compounds, xylene derivatives, etc.
  • the thermal crosslinking agent one or a combination of two or more of the above specific examples can be used.
  • the photosensitive resin composition according to the present embodiment may further contain an antioxidant.
  • an antioxidant at least one selected from a phenol-based antioxidant, a phosphorus-based antioxidant, and a thioether-based antioxidant can be used.
  • the antioxidant can further suppress oxidation of the resin film formed by the photosensitive resin composition.
  • the photosensitive resin composition according to the present embodiment may further include a dissolution promoter.
  • the dissolution promoter is a component capable of improving the solubility of the exposed portion of the coating film formed using the photosensitive resin composition in a developer and improving scum during patterning.
  • a dissolution promoter a compound having a phenolic hydroxyl group is preferable.
  • the dissolution promoter preferably contains one having a biphenol type skeleton or a bisphenol A type skeleton. This allows the skeleton of the alkali-soluble resin (A) to interact with the dissolution promoter, further improving the dispersibility of the alkali-soluble resin (A).
  • the photosensitive resin composition according to the present embodiment may further contain a filler.
  • a filler an appropriate filler can be selected depending on the mechanical properties and thermal properties required for the resin film formed by the photosensitive resin composition, and specific examples thereof include inorganic fillers and organic fillers. Examples of inorganic fillers include silica, metal compounds, talc, clay, mica, glass fibers, etc. Specific examples of organic fillers include organosilicone powder, polyethylene powder, etc.
  • the filler one or a combination of two or more of the above-mentioned fillers can be used.
  • the method for preparing the photosensitive resin composition in this embodiment is not limited, and any known method can be used depending on the components contained in the photosensitive resin composition.
  • the photosensitive resin composition can be prepared by mixing and dissolving the alkali-soluble resin (A), the polyether-modified polydimethylsiloxane (B), and the photosensitizer (D) in the solvent (C), thereby obtaining a photosensitive resin composition in the form of a varnish.
  • the photosensitive resin composition of the present embodiment is used to form a cured film for semiconductor devices such as wafer level packages and panel level packages.
  • the above-mentioned cured film is composed of a cured film obtained by, for example, applying a photosensitive resin composition, pre-baking, exposing and developing it, patterning it into a desired shape, and curing it by post-baking.
  • the cured film can be used as a buffer coat film (protective film), an interlayer film, a dam material, etc. for electronic devices.
  • the above-mentioned cured film can be suitably used as a buffer coat film.
  • the step of applying the photosensitive resin composition is preferably performed by, for example, spin coating. This allows a more uniform resin film to be formed on the substrate.
  • the thickness of the cured film is not particularly limited, but is, for example, from 2 ⁇ m to 30 ⁇ m, and preferably from 5 ⁇ m to 20 ⁇ m.
  • various methods can be applied to remove the solvent (e.g., heating, etc.), but in the case of using it for a panel level package, it is preferable to apply reduced pressure drying in consideration of the relatively large area. In other words, it is preferable to dry the panel coated with the photosensitive resin composition in a reduced pressure environment (e.g., an environment of 30 Pa or less).
  • the conditions are, for example, 70 to 160° C. and about 5 seconds to 30 minutes.
  • electromagnetic waves or particle beams of various wavelengths can be used.
  • ultraviolet rays such as g-rays and i-rays, visible light, lasers, X-rays, electron beams, etc. are used.
  • Ultraviolet rays such as g-rays or i-rays are preferred.
  • the exposure amount is appropriately set depending on the sensitivity of the photosensitive resin composition, and is, for example, about 30 to 3000 mJ/ cm2 . Exposure is usually performed using an appropriate mask pattern. For development, various developers can be used.
  • alkaline developers such as alkali metal carbonates, alkali metal hydroxides, and tetramethylammonium hydroxide
  • organic developers such as dimethylformamide, N-methyl-2-pyrrolidone, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and butyl acetate.
  • alkaline developers are preferred, and an aqueous solution of tetramethylammonium hydroxide is particularly preferred.
  • Methods for supplying the developer include spray, paddle, and immersion methods. In terms of processing large-area panels, the spray method is preferred.
  • the post-baking conditions are not particularly limited, but are, for example, at a temperature of 80° C. or higher and 450° C. or lower for 30 minutes or longer and 300 minutes or shorter.
  • the electronic device 100 shown in FIG. 1 is, for example, a semiconductor chip.
  • the electronic device 100 is mounted on a wiring board via bumps 52 to obtain a semiconductor package.
  • the electronic device 100 includes a semiconductor substrate on which semiconductor elements such as transistors are provided, and a multilayer wiring layer provided on the semiconductor substrate (not shown).
  • the uppermost layer of the multilayer wiring layer includes an interlayer insulating film 30 and a top layer wiring 34 provided on the interlayer insulating film 30.
  • the top layer wiring 34 is made of, for example, Al.
  • a passivation film 32 is provided on the interlayer insulating film 30 and the top layer wiring 34. An opening is provided in a part of the passivation film 32 to expose the top layer wiring 34.
  • a redistribution layer 40 is provided on the passivation film 32.
  • the redistribution layer 40 has an insulating layer 42 provided on the passivation film 32, a redistribution 46 provided on the insulating layer 42, and an insulating layer 44 provided on the insulating layer 42 and the redistribution 46.
  • the insulating layer 42 has an opening through which the top layer wiring 34 is exposed.
  • the redistribution 46 is formed on the insulating layer 42 and in the opening provided in the insulating layer 42, and is electrically connected to the top layer wiring 34.
  • the insulating layer 44 has an opening through which a predetermined region of the redistribution 46 is exposed.
  • a bump 52 is formed, for example, via a UBM (Under Bump Metallurgy) layer 50.
  • the electronic device 100 is connected to a wiring board or the like, for example, via the bump 52.
  • one or more of insulating layers 42 and 44 can be formed, for example, by a cured film formed by curing the above-mentioned photosensitive resin composition.
  • a coating film formed from the photosensitive resin composition is exposed to ultraviolet light, developed and patterned, and then heated and cured to form insulating layer 42 or insulating layer 44.
  • the method for producing an electronic device of this embodiment includes a coating film forming step of applying the photosensitive resin composition of this embodiment onto a substrate to form a coating film.
  • the method for producing an electronic device according to the present embodiment may further include an exposure step of exposing the formed coating film to light, a development step of developing the exposed coating film, and a heating step of heating the coating film remaining after development to harden the coating film and form a hardened film. This forms a hardened film of the photosensitive resin composition, and the hardened film is used as the insulating layer 42 or the insulating layer 44 constituting the electronic device 100.
  • the method for producing an electronic device may further include a step of cleaning the coating film on the back side of the substrate after the coating film forming step, which makes it possible to remove unnecessary coating film that has spread to the back side of the substrate when the coating film is formed by spin coating or the like, and to improve the shape of the edge of the cured film formed from the coating film.
  • the photosensitive resin composition of this embodiment has an appropriate affinity with the back-rinse solvent used to remove unnecessary coating film during coating film formation, so that the end shape of the cured film can be made appropriate.
  • the photosensitive resin composition of this embodiment has an appropriately low affinity with the back-rinse solvent, so that the back-rinse solvent can be prevented from wrapping around the substrate surface, i.e., the coating film side of the photosensitive resin composition on the substrate, and the coating film is not dissolved inadvertently.
  • the coating film is prebaked to form a cured film, the occurrence of unexpected steps or defects at the end can be suppressed, and the end shape can be made better.
  • the photosensitive resin composition of this embodiment has an appropriately high affinity with the back-rinse solvent, so that the original purpose of the back-rinse solvent, that is, removing unnecessary photosensitive resin composition that has wrapped around the back side of the substrate during coating film formation, can be achieved.
  • the penetration diameter of the back-rinse solvent is preferably 15 mm or more, more preferably 18 mm or more, even more preferably 20 mm or more, and is preferably 28 mm or less, more preferably 26 mm or less, even more preferably 23 mm or less.
  • the penetration diameter is equal to or less than the above upper limit (the back-rinse solvent does not penetrate too much)
  • the affinity between the photosensitive resin composition and the back-rinse solvent can be appropriately reduced, and the shape of the edge of the coating film can be made better.
  • the affinity between the photosensitive resin composition and the back-rinse solvent can be appropriately improved, and unnecessary coating film on the back surface of the substrate can be cleaned and removed as desired.
  • the affinity between the photosensitive resin composition and the back-rinse solvent is evaluated by the following method.
  • the photosensitive resin composition is spin-coated on a substrate to a thickness of 20 ⁇ m to form a coating film.
  • 7 mg of back-rinse solvent is dropped onto the coating film from a height of 5 cm from the coating film surface using a dropper.
  • the penetration diameter of the back-rinse solvent on the coating film (the diameter of the part penetrated by the back-rinse solvent) (mm) is measured.
  • alkali-soluble resin 1 which is a polyamide resin, was synthesized by the following procedure.
  • a four-necked glass separable flask equipped with a thermometer, a stirrer, a raw material inlet, and a dry nitrogen gas inlet tube 170.20 g (0.346 mol) of a mixture of dicarboxylic acid derivatives obtained by reacting 206.58 g (0.800 mol) of diphenyl ether-4,4'-dicarboxylic acid represented by the following formula (DC2) with 216.19 g (1.600 mol) of 1-hydroxy-1,2,3-benzotriazole monohydrate, 4.01 g (0.047 mol) of 5-aminotetrazole, 45.22 g (0.196 mol) of 4,4'-methylenebis(2-aminophenol) represented by the following formula (DA2), and 56.24 g (0.196 mol) of 4,4'-methylenebis(2-aminophenol) represented by the following formula (DA2), and
  • the precipitate was then filtered off and thoroughly washed with water, and then dispersed in NMP (N-methylpyrrolidone) without drying, to obtain a solution of the desired alkali-soluble resin 1.
  • the weight average molecular weight Mw of the resulting alkali-soluble resin 1 was 18081.
  • Photosensitizer 1 which is a diazoquinone compound, was synthesized by the following procedure. Into a four-neck separable flask equipped with a thermometer, a stirrer, a raw material inlet, and a dry nitrogen gas inlet tube, 11.04 g (0.026 mol) of a compound represented by the following formula (P-1), 18.81 g (0.070 mol) of 1,2-naphthoquinone-2-diazide-5-sulfonyl chloride, and 170 g of acetone were placed and stirred to dissolve.
  • P-1 a compound represented by the following formula (P-1)
  • P-1 1,2-naphthoquinone-2-diazide-5-sulfonyl chloride
  • Thermal crosslinking agent 1 paraxylene glycol (PXG, manufactured by Ihara Nikkei Chemical Industry Co., Ltd.)
  • Dissolution promoter 1 2,2'-methylene bisphenol (manufactured by Honshu Chemical Industry Co., Ltd., product name: o,o'-BPF)
  • Dissolution promoter 2 Compound of the following formula (2), manufactured by Air Water Inc.
  • Adhesion aid 1 3-methacryloxypropyltrimethoxysilane
  • Adhesion aid 2 3-glycidoxypropyltriethoxysilane
  • Solvent 1 ⁇ -butyrolactone (GBL)
  • Solvent 2 N-methyl-2-pyrrolidone (NMP)
  • NMP N-methyl-2-pyrrolidone
  • Fluorosurfactant 1 FC4432, manufactured by 3M Japan Ltd., weight average molecular weight (Mw): 8202, maximum peak molecular weight: 16182, surface tension: 24.2 mN/m
  • Polyether-modified polydimethylsiloxane 1 was synthesized by referring to Synthesis Example 2 in paragraph 0115 of JP-A-2002-079109, using polydimethylsiloxane represented by the following formula (4) and a polyether compound represented by the following formula (3) instead of dimethallyl polyether.
  • the obtained polyether-modified polydimethylsiloxane 1 had m of 3, p of 7, q of 0, x of 4, y of 3, and R of hydrogen in the above general formula (1). Note that m, p, q, x, and y in general formula (1) were determined from the structures of the polydimethylsiloxane represented by the above formula (4) and the polyether compound represented by the above formula (3) used in the synthesis of polyether-modified polydimethylsiloxane 1.
  • the polystyrene-equivalent weight average molecular weight of the obtained polyether-modified polydimethylsiloxane 1 was measured by the gel permeation chromatography method described below and was found to be 1730.
  • the polystyrene-equivalent weight average molecular weight at the maximum peak of the molecular weight distribution was 2234, and Mw/Mn was 2.23.
  • the surface tension of polyether-modified polydimethylsiloxane 1 was 29.4 mN/m
  • the density was 1.037 ⁇ 0.030 g/mL
  • the refractive index was 1.433 ⁇ 0.010
  • the non-volatile content was 96.25 ⁇ 3.75%.
  • Polyether-modified polydimethylsiloxane 2 was synthesized in a manner similar to that of Polyether-modified polydimethylsiloxane 1 described above, except that the types and compounding ratios of polydimethylsiloxane and polyether compound were changed.
  • the obtained polyether-modified polydimethylsiloxane 2 had m of 3, p of 3, q of 5, x of 3, y of 3, and R of hydrogen in the above general formula (1).
  • m, p, q, x, and y in general formula (1) were determined from the structures of the polydimethylsiloxane and polyether compound used in the synthesis of polyether-modified polydimethylsiloxane 2.
  • the density of the polyether-modified polydimethylsiloxane was measured at 20° C. in accordance with ISO 2811-3:2011.
  • the refractive index of the polyether-modified polydimethylsiloxanes was determined according to DIN 51423.
  • the non-volatile content of the polyether-modified polydimethylsiloxane was measured in accordance with ISO 3251:2019 at 105° C. for 1 hour.
  • the surface tension (mN/m) of the polyether-modified polydimethylsiloxane and the fluorosurfactant was measured at 23° C. in a 1% GBL solution using a contact angle meter (DMs-401, Kyowa Interface Science Co., Ltd.).
  • Photosensitive resin compositions of Examples and Comparative Examples were prepared as follows, and their defoaming properties were evaluated. Each raw material component other than polyether-modified polydimethylsiloxane and fluorosurfactant was placed in a stirring vessel (bottom area: 70 cm2 ) according to the formulation in Table 1 so that the total amount of photosensitive resin composition was 500 mL, and stirred under conditions of temperature: 23°C, stirring blade height: 1.0 cm from the bottom, rotation speed: 250 rpm, stirring time: 3 hours, and nitrogen atmosphere.
  • a surfactant was added according to the formulation in Table 1, and stirred under conditions of temperature: 23°C, stirring blade height: 1.0 cm from the bottom, rotation speed: 100 rpm, stirring time: 30 minutes, and nitrogen atmosphere to obtain the photosensitive resin composition of each example.
  • 5 mL of the resulting photosensitive resin composition was placed in a 20 mL graduated cylinder and allowed to stand at 23° C. for 15 hours. The foam height (mm) after 15 hours was measured. The results are shown in Table 1. Note that a lower foam height indicates better defoaming properties.

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002079109A (ja) 1999-12-14 2002-03-19 Hitachi Chem Co Ltd 光半導体金属−有機物質混合体、光半導体金属含有組成物、光触媒性被膜の製造法及び光触媒性部材
JP2013035838A (ja) * 2011-08-04 2013-02-21 Lg Chem Ltd シラン系化合物およびこれを含む感光性樹脂組成物
JP2016189006A (ja) 2012-09-28 2016-11-04 富士フイルム株式会社 感光性樹脂組成物、これを用いた硬化膜の製造方法、硬化膜、液晶表示装置および有機ｅｌ表示装置
JP2017198840A (ja) * 2016-04-27 2017-11-02 株式会社カネカ 隔壁形成用ポジ型感光性組成物
WO2018159236A1 (ja) * 2017-02-28 2018-09-07 富士フイルム株式会社 インクジェット用液体組成物、及び、インクジェット記録方法
JP2022157763A (ja) * 2021-03-31 2022-10-14 富士フイルム株式会社 機上現像型平版印刷版原版、平版印刷版の作製方法、及び構造体
JP7202037B1 (ja) * 2021-12-29 2023-01-11 互応化学工業株式会社 レジスト用樹脂組成物、レジスト膜の製造方法、及びパターン化されたレジスト膜
JP2023055060A (ja) 2021-10-05 2023-04-17 美的集団股▲フン▼有限公司 内接噛合遊星歯車装置及びロボット用関節装置

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002079109A (ja) 1999-12-14 2002-03-19 Hitachi Chem Co Ltd 光半導体金属−有機物質混合体、光半導体金属含有組成物、光触媒性被膜の製造法及び光触媒性部材
JP2013035838A (ja) * 2011-08-04 2013-02-21 Lg Chem Ltd シラン系化合物およびこれを含む感光性樹脂組成物
JP2016189006A (ja) 2012-09-28 2016-11-04 富士フイルム株式会社 感光性樹脂組成物、これを用いた硬化膜の製造方法、硬化膜、液晶表示装置および有機ｅｌ表示装置
JP2017198840A (ja) * 2016-04-27 2017-11-02 株式会社カネカ 隔壁形成用ポジ型感光性組成物
WO2018159236A1 (ja) * 2017-02-28 2018-09-07 富士フイルム株式会社 インクジェット用液体組成物、及び、インクジェット記録方法
JP2022157763A (ja) * 2021-03-31 2022-10-14 富士フイルム株式会社 機上現像型平版印刷版原版、平版印刷版の作製方法、及び構造体
JP2023055060A (ja) 2021-10-05 2023-04-17 美的集団股▲フン▼有限公司 内接噛合遊星歯車装置及びロボット用関節装置
JP7202037B1 (ja) * 2021-12-29 2023-01-11 互応化学工業株式会社 レジスト用樹脂組成物、レジスト膜の製造方法、及びパターン化されたレジスト膜

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