WO2024075229A1 - 感光性樹脂組成物、感光性エレメント、プリント配線板及びプリント配線板の製造方法 - Google Patents

感光性樹脂組成物、感光性エレメント、プリント配線板及びプリント配線板の製造方法 Download PDF

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WO2024075229A1
WO2024075229A1 PCT/JP2022/037335 JP2022037335W WO2024075229A1 WO 2024075229 A1 WO2024075229 A1 WO 2024075229A1 JP 2022037335 W JP2022037335 W JP 2022037335W WO 2024075229 A1 WO2024075229 A1 WO 2024075229A1
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Prior art keywords
component
resin composition
mass
photosensitive resin
group
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PCT/JP2022/037335
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English (en)
French (fr)
Japanese (ja)
Inventor
伸仁 古室
雄汰 代島
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Resonac Corp
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Resonac Corp
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Priority to JP2024555540A priority Critical patent/JPWO2024075229A1/ja
Priority to PCT/JP2022/037335 priority patent/WO2024075229A1/ja
Priority to US18/859,679 priority patent/US20250258430A1/en
Priority to KR1020257005438A priority patent/KR20250087516A/ko
Priority to CN202280095381.9A priority patent/CN119096198A/zh
Priority to TW112135469A priority patent/TW202417522A/zh
Publication of WO2024075229A1 publication Critical patent/WO2024075229A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0755—Non-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
    • G03F7/004—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
    • G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
    • G03F7/0043—Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
    • H05K3/06—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed chemically or electrolytically, e.g. by photo-etch process
    • H05K3/061—Etching masks
    • H05K3/064—Photoresists

Definitions

  • This disclosure relates to a photosensitive resin composition for permanent resist, a photosensitive element, a printed wiring board, and a method for manufacturing a printed wiring board.
  • permanent resist In the field of printed wiring boards, permanent resist is formed on printed wiring boards.
  • the permanent resist prevents corrosion of the conductor layer and maintains electrical insulation between the conductor layers when the printed wiring board is in use.
  • permanent resist also serves as a solder resist film that prevents solder from adhering to unnecessary parts of the conductor layer of the printed wiring board in processes such as flip-chip mounting and wire bonding mounting of semiconductor elements on the printed wiring board via solder.
  • thermosetting resin composition Traditionally, permanent resists have been produced by screen printing using a thermosetting resin composition, or by a photographic method using a photosensitive resin composition.
  • a thermosetting resin paste is screen printed and thermally cured to form a permanent resist, except for the IC chip, electronic components, or LCD (liquid crystal display) panel and the connection wiring pattern portion (see, for example, Patent Document 1).
  • a photographic method is used to form an image in the permanent resist, in which a photosensitive resin composition is applied and dried, and then selectively irradiated with active light such as ultraviolet light to harden it, and only the unirradiated parts are removed by development to form an image.
  • the photographic method is widely used in the electronic materials industry to form images of photosensitive materials, since its ease of operation makes it suitable for mass production (see, for example, Patent Document 2).
  • permanent resists formed from conventional photosensitive resin compositions can crack under harsh environments such as high temperatures, and there is a demand for photosensitive resin compositions that can form permanent resists with excellent crack resistance.
  • resist residues are generated after development, which can lead to fatal defects when connecting bumps to chips, and there is a demand for photosensitive resin compositions with excellent developability.
  • the object of the present disclosure is to provide a photosensitive resin composition for permanent resist that can form a permanent resist with excellent crack resistance and excellent developability, as well as a photosensitive element, a printed wiring board, and a method for manufacturing a printed wiring board that use the photosensitive resin composition.
  • a photosensitive resin composition for a permanent resist comprising: (A) an acid-modified vinyl group-containing resin; (B) an epoxy compound; (C) a photopolymerization initiator; (D) a photopolymerizable compound; and (F) an inorganic filler, wherein an equivalent ratio of an epoxy group contained in the epoxy compound (B) to a carboxy group contained in the acid-modified vinyl group-containing resin (A) is 1.25 to 7.50; and the inorganic filler (F) comprises a silica filler having a vinyl group derived from a vinylsilane compound.
  • a method for producing a printed wiring board comprising: a step of forming a photosensitive layer on a substrate using the photosensitive resin composition according to any one of the above [1] to [4]; a step of exposing and developing the photosensitive layer to form a resist pattern; and a step of curing the resist pattern to form a permanent resist.
  • a method for producing a printed wiring board comprising the steps of: forming a photosensitive layer on a substrate using the photosensitive element described in [5] above; exposing and developing the photosensitive layer to form a resist pattern; and hardening the resist pattern to form a permanent resist.
  • the present disclosure provides a photosensitive resin composition for a permanent resist that can form a permanent resist with excellent crack resistance and excellent developability, as well as a photosensitive element, a printed wiring board, and a method for manufacturing a printed wiring board that use the photosensitive resin composition.
  • FIG. 1 is a cross-sectional view that illustrates a photosensitive element according to this embodiment.
  • the term “layer” includes not only structures with shapes formed over the entire surface when observed in a plan view, but also structures with shapes formed on a portion of the surface.
  • the term “process” includes not only independent processes, but also processes that cannot be clearly distinguished from other processes, as long as the intended purpose of the process is achieved.
  • a numerical range indicated using “ ⁇ ” indicates a range that includes the numerical values described before and after " ⁇ " as the minimum and maximum values, respectively.
  • the upper or lower limit of a numerical range of a certain stage may be replaced with the upper or lower limit of a numerical range of another stage.
  • the upper or lower limit of the numerical range may be replaced with a value shown in an example.
  • “A or B” may include either A or B, or may include both.
  • the materials exemplified below may be used alone or in combination of two or more types.
  • the content of each component in the composition means the total amount of those multiple substances present in the composition, unless otherwise specified.
  • solids refers to the non-volatile content excluding volatile substances such as water and diluents contained in the photosensitive resin composition, and refers to the components that remain without evaporating or vaporizing when the resin composition is dried, and includes components that are liquid, syrup-like, or waxy at room temperature (25°C, the same applies below).
  • the photosensitive resin composition contains (A) an acid-modified vinyl group-containing resin, (B) an epoxy compound, (C) a photopolymerization initiator, (D) a photopolymerizable compound, and (F) an inorganic filler, in which the equivalent ratio (epoxy group/carboxy group equivalent ratio, molar ratio) of the epoxy group contained in the epoxy compound (B) to the carboxy group contained in the acid-modified vinyl group-containing resin (A) is 1.25 to 7.50, and the inorganic filler (F) contains a silica filler having a vinyl group derived from a vinylsilane compound.
  • the photosensitive resin composition according to this embodiment is a negative photosensitive resin composition, and a cured product of the photosensitive resin composition can be used as a permanent resist.
  • the present inventors have discovered that when the epoxy group/carboxy group equivalent ratio is 1.25 or more, the epoxy group derived from the epoxy compound is present in greater numbers than the carboxy group derived from the acid-modified vinyl group-containing resin, and the elasticity of the permanent resist formed thereby tends to improve, and therefore the crack resistance of the permanent resist can be improved.
  • the solubility of the cured product formed in a developer tends to decrease, and the developability tends to decrease.
  • the silica filler having a vinyl group derived from a vinylsilane compound is more likely to be developed by bonding with functional groups such as vinyl groups contained in the acid-modified vinyl group-containing resin, photopolymerizable compound, etc. in the photosensitive resin composition than other silica fillers, and therefore even if the epoxy group/carboxy group equivalent ratio is high, it is possible to suppress the solubility of the cured product formed in a developer from decreasing, and the developability can be improved. This has led to the completion of the present invention.
  • the photosensitive resin composition according to this embodiment can form a permanent resist with excellent crack resistance, and can reduce the generation of residues after development, so it also has excellent developability.
  • the photosensitive resin composition according to this embodiment can form a permanent resist with excellent flowability and excellent adhesion to copper substrates.
  • the photosensitive resin composition according to this embodiment is also excellent in the performance required of a photosensitive resin composition used in the manufacture of printed wiring boards, such as resolution, electrical insulation, solder heat resistance, solvent resistance, acid resistance, and alkali resistance. Each component contained in the photosensitive resin composition according to this embodiment will be described in detail below.
  • the photosensitive resin composition according to the present embodiment contains an acid-modified vinyl group-containing resin as component (A).
  • the acid-modified vinyl group-containing resin is not particularly limited as long as it has a vinyl bond, which is a photopolymerizable ethylenically unsaturated bond, and an alkali-soluble acidic group.
  • Examples of the group having an ethylenically unsaturated bond contained in component (A) include a vinyl group, an allyl group, a propargyl group, a butenyl group, an ethynyl group, a phenylethynyl group, a maleimide group, a nadiimide group, and a (meth)acryloyl group.
  • a (meth)acryloyl group may be used.
  • Examples of the acidic group contained in component (A) include a carboxy group, a sulfo group, and a phenolic hydroxyl group. Among these, from the viewpoint of resolution, a carboxy group may be used.
  • the (A) component may be an acid-modified vinyl group-containing epoxy derivative obtained by reacting (a) an epoxy resin (hereinafter sometimes referred to as "(a) component") with (b) an ethylenically unsaturated group-containing organic acid (hereinafter sometimes referred to as "(b) component”) to obtain a resin (A') (hereinafter sometimes referred to as "(A') component”), with (c) a saturated or unsaturated group-containing polybasic acid anhydride (hereinafter sometimes referred to as "(c) component").
  • Acid-modified epoxy (meth)acrylate is a resin obtained by acid-modifying epoxy (meth)acrylate, which is a reaction product of components (a) and (b), with component (c).
  • acid-modified epoxy (meth)acrylate for example, an addition reaction product obtained by adding a saturated or unsaturated polybasic acid anhydride to an ester obtained by reacting an epoxy resin with a vinyl group-containing monocarboxylic acid can be used.
  • Examples of the (A) component include an acid-modified vinyl group-containing resin (A1) (hereinafter, sometimes referred to as “component (A1)”) obtained by using a bisphenol novolac type epoxy resin (a1) (hereinafter, sometimes referred to as “epoxy resin (a1)”) as the (a) component, and an acid-modified vinyl group-containing resin (A2) (hereinafter, sometimes referred to as “component (A2)”) obtained by using an epoxy resin (a2) other than epoxy resin (a1) (hereinafter, sometimes referred to as “epoxy resin (a2)”) as the (a) component.
  • component (A1)) obtained by using a bisphenol novolac type epoxy resin (a1) (hereinafter, sometimes referred to as “epoxy resin (a1)") as the (a) component
  • component (A2)) an acid-modified vinyl group-containing resin obtained by using an epoxy resin (a2) other than epoxy resin (a1) (hereinafter, sometimes referred to as "epoxy resin (a2)) as
  • Epoxy resin (a1) The epoxy resin (a1) may be, for example, an epoxy resin having a structural unit represented by the following formula (I) or (II).
  • the epoxy resin (a1) may be an epoxy resin having a structural unit represented by formula (I).
  • R 11 represents a hydrogen atom or a methyl group, and a plurality of R 11 may be the same or different.
  • Y 1 and Y 2 each independently represent a hydrogen atom or a glycidyl group, and at least one of Y 1 and Y 2 is a glycidyl group.
  • R 11 may be a hydrogen atom, and Y 1 and Y 2 may be a glycidyl group.
  • the number of structural units represented by formula (I) in epoxy resin (a1) is 1 or more, and may be 10 to 100, 15 to 80, or 15 to 70. If the number of structural units is within the above range, it becomes easier to improve heat resistance and electrical insulation.
  • the number of structural units indicates an integer value in a single molecule, and indicates a rational number that is an average value in an aggregate of multiple types of molecules (the same applies below).
  • R 12 represents a hydrogen atom or a methyl group, and a plurality of R 12 may be the same or different.
  • Y 3 and Y 4 each independently represent a hydrogen atom or a glycidyl group, and at least one of Y 3 and Y 4 is a glycidyl group.
  • R 12 may be a hydrogen atom, and Y 3 and Y 4 may be a glycidyl group.
  • the number of structural units represented by formula (II) in the epoxy resin (a1) is 1 or more, and may be 10 to 100, 15 to 80, or 15 to 70. If the number of structural units is within the above range, it becomes easier to improve heat resistance and electrical insulation.
  • an epoxy resin in which R 12 is a hydrogen atom and Y 3 and Y 4 are glycidyl groups is commercially available as the EXA-7376 series (trade name, manufactured by DIC Corporation).
  • an epoxy resin in which R 12 is a methyl group and Y 3 and Y 4 are glycidyl groups is commercially available as the EPON SU8 series (trade name, manufactured by Mitsubishi Chemical Corporation).
  • the epoxy resin (a2) is not particularly limited as long as it is an epoxy resin different from the epoxy resin (a1), and may be at least one selected from the group consisting of novolac type epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, triphenolmethane type epoxy resins, and biphenyl type epoxy resins.
  • the epoxy resin (a2) may be, for example, a bisphenol A type epoxy resin or a bisphenol F type epoxy resin having a structural unit represented by the following formula (III).
  • the epoxy resin having such a structural unit may be, for example, a bisphenol A type epoxy resin or a bisphenol F type epoxy resin represented by the following formula (III').
  • R13 represents a hydrogen atom or a methyl group, and a plurality of R13s may be the same or different, and Y5 represents a hydrogen atom or a glycidyl group.
  • n2 represents a number of 1 or more, and when n2 is 2 or more, a plurality of Y5s may be the same or different, and at least one Y5 is a glycidyl group.
  • R 13 may be a hydrogen atom.
  • Y 5 may be a glycidyl group.
  • n 2 represents 1 or more, but may be 10 to 100, 10 to 80, or 15 to 60. When n 2 is within the above range, it becomes easier to improve the linearity and heat resistance of the resist pattern contour.
  • a bisphenol A type epoxy resin or a bisphenol F type epoxy resin in which Y5 in formula (III) is a glycidyl group can be obtained, for example, by reacting a hydroxyl group ( -OY5 ) of a bisphenol A type epoxy resin or a bisphenol F type epoxy resin in which Y5 in formula (III) is a hydrogen atom with epichlorohydrin.
  • the reaction may be carried out in a polar organic solvent such as dimethylformamide, dimethylacetamide, or dimethylsulfoxide in the presence of an alkali metal hydroxide at a reaction temperature of 50 to 120°C. If the reaction temperature is within the above range, the reaction will not slow down too much and side reactions can be suppressed.
  • a polar organic solvent such as dimethylformamide, dimethylacetamide, or dimethylsulfoxide
  • bisphenol A type epoxy resin or bisphenol F type epoxy resin represented by formula (III') for example, jER807, jER815, jER825, jER827, jER828, jER834, jER1001, jER1004, jER1007 and jER1009 (all of which are product names manufactured by Mitsubishi Chemical Corporation), DER-330, DER-301 and DER-361 (all of which are product names manufactured by Dow Chemical Company), YD-8125, YDF-170, YDF-175S, YDF-2001, YDF-2004 and YDF-8170 (all of which are product names manufactured by Nippon Steel Chemical & Material Co., Ltd.) are commercially available.
  • (Ethylenically unsaturated group-containing organic acid (b)) examples include acrylic acid, acrylic acid derivatives such as dimers of acrylic acid, methacrylic acid, ⁇ -furfurylacrylic acid, ⁇ -styrylacrylic acid, cinnamic acid, crotonic acid, and ⁇ -cyanocinnamic acid, half-ester compounds which are reaction products of hydroxyl group-containing acrylates and dibasic acid anhydrides, and half-ester compounds which are reaction products of vinyl group-containing monoglycidyl ethers or vinyl group-containing monoglycidyl esters and dibasic acid anhydrides.
  • the component (b) can be used alone or in combination of two or more.
  • the semi-ester compound can be obtained, for example, by reacting a hydroxyl group-containing acrylate, a vinyl group-containing monoglycidyl ether, or a vinyl group-containing monoglycidyl ester with a dibasic acid anhydride in an equimolar ratio.
  • hydroxyl group-containing acrylates, vinyl group-containing monoglycidyl ethers, and vinyl group-containing monoglycidyl esters examples include hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate, polyethylene glycol monoacrylate, polyethylene glycol monomethacrylate, trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentaacrylate, pentaerythritol pentamethacrylate, glycidyl acrylate, and glycidyl methacrylate.
  • dibasic acid anhydrides examples include succinic anhydride, maleic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, methyltetrahydrophthalic anhydride, ethyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, ethylhexahydrophthalic anhydride, and itaconic anhydride.
  • the reaction may be carried out in a ratio such that 0.6 to 1.05 equivalents of component (b) are reacted per 1 equivalent of the epoxy groups in component (a), or in a ratio such that 0.8 to 1.0 equivalents of component (b) are reacted.
  • the photopolymerizability is improved, that is, the photosensitivity is increased, making it easier to improve the resolution.
  • Component (a) and component (b) can be dissolved in an organic solvent and reacted.
  • organic solvents include ketones such as methyl ethyl ketone and cyclohexanone; aromatic hydrocarbons such as toluene, xylene, and tetramethylbenzene; glycol ethers such as methyl cellosolve, butyl cellosolve, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol diethyl ether, and triethylene glycol monoethyl ether; esters such as ethyl acetate, butyl acetate, butyl cellosolve acetate, and carbitol acetate; aliphatic hydrocarbons such as octane and decane; and petroleum-based solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, and solvent
  • a catalyst may be used to promote the reaction between component (a) and component (b).
  • catalysts include triethylamine, benzylmethylamine, methyltriethylammonium chloride, benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltrimethylammonium iodide, and triphenylphosphine.
  • the catalyst may be used alone or in combination of two or more.
  • the amount of the catalyst used may be 0.01 to 10 parts by mass, 0.05 to 2 parts by mass, or 0.1 to 1 part by mass, per 100 parts by mass of the total of the (a) component and the (b) component.
  • a polymerization inhibitor may be used to prevent polymerization during the reaction.
  • examples of polymerization inhibitors include hydroquinone, methylhydroquinone, hydroquinone monomethyl ether, catechol, and pyrogallol.
  • the polymerization inhibitor may be used alone or in combination of two or more. From the viewpoint of storage stability, the amount of the polymerization inhibitor used may be 0.01 to 1 part by mass, 0.02 to 0.8 parts by mass, or 0.04 to 0.5 parts by mass per 100 parts by mass of the total of the (a) component and the (b) component.
  • the reaction temperature between components (a) and (b) may be 60 to 150°C, 80 to 120°C, or 90 to 110°C from the viewpoint of productivity.
  • Component (A') which is obtained by reacting components (a) and (b), is presumed to have hydroxyl groups formed by a ring-opening addition reaction between the epoxy groups of component (a) and the carboxyl groups of component (b). It is presumed that by further reacting component (A') with component (c), an acid-modified vinyl group-containing epoxy resin can be obtained in which the hydroxyl groups of component (A') (including the hydroxyl groups originally present in component (a)) and the acid anhydride groups of component (c) are semi-esterified.
  • (c)) Polybasic Acid Anhydride
  • the (c) component examples include succinic anhydride, maleic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, methyltetrahydrophthalic anhydride, ethyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, ethylhexahydrophthalic anhydride, and itaconic anhydride.
  • tetrahydrophthalic anhydride may be used from the viewpoint of resolution.
  • the (c) component may be used alone or in combination of two or more.
  • the reaction temperature between component (A') and component (c) may be 50 to 150°C, 60 to 120°C, or 70 to 100°C from the viewpoint of productivity.
  • component (a) may be used in combination with, for example, a hydrogenated bisphenol A type epoxy resin, or a styrene-maleic acid resin such as a hydroxyethyl (meth)acrylate modified styrene-maleic anhydride copolymer.
  • a hydrogenated bisphenol A type epoxy resin or a styrene-maleic acid resin such as a hydroxyethyl (meth)acrylate modified styrene-maleic anhydride copolymer.
  • component (A') In the reaction between component (A') and component (c), for example, the acid value of component (A) can be adjusted by reacting 0.1 to 1.0 equivalents of component (c) with 1 equivalent of hydroxyl groups in component (A').
  • the acid value of the (A) component may be 30 to 150 mgKOH/g or 40 to 120 mgKOH/g.
  • the acid value of the (A) component may be 30 mgKOH/g or more, the photosensitive resin composition tends to have excellent solubility in a dilute alkaline solution.
  • the acid value of the (A) component may be 35 mgKOH/g or more or 40 mgKOH/g or more.
  • the acid value of the (A) component is 150 mgKOH/g or less, the electrical properties of the permanent resist are easily improved.
  • the acid value of the (A) component may be 120 mgKOH/g or less, 100 mgKOH/g or less, 90 mgKOH/g or less, 80 mgKOH/g or less, 70 mgKOH/g or less, 60 mgKOH/g or less, or 50 mgKOH/g or less.
  • Vf indicates the titration volume (mL) of 0.1 N KOH aqueous solution
  • Wp indicates the measured mass (g) of the solution of component (A)
  • I indicates the proportion (mass%) of non-volatile matter in the measured solution of component (A).
  • the weight average molecular weight (Mw) of component (A) may be 3,000 to 30,000, 4,000 to 25,000, or 5,000 to 18,000 from the viewpoints of resolution, heat resistance, and electrical insulation.
  • Mw can be measured by gel permeation chromatography (GPC). Mw can be measured, for example, under the GPC conditions below, and the value converted using the calibration curve of standard polystyrene can be used as Mw.
  • the calibration curve can be created using a 5-sample set ("PStQuick MP-H" and "PStQuick B", manufactured by Tosoh Corporation) as standard polystyrene.
  • GPC device High-speed GPC device "HCL-8320GPC" (manufactured by Tosoh Corporation)
  • Detector Differential refractometer or UV detector (manufactured by Tosoh Corporation)
  • Eluent Tetrahydrofuran (THF) Measurement temperature: 40°C Flow rate: 0.35 mL/min Sample concentration: 10 mg/5 mL THF Injection volume: 20 ⁇ L
  • the content of component (A) in the photosensitive resin composition may be 10% by mass or more, 15% by mass or more, or 20% by mass or more, and may be 80% by mass or less, 70% by mass or less, 50% by mass or less, or 40% by mass or less, based on the total solid content of the photosensitive resin composition, from the viewpoint of improving the heat resistance, electrical properties, and chemical resistance of the permanent resist. From the same viewpoint, the content of component (A) may be 10% by mass to 80% by mass, 15% by mass to 70% by mass, 20% by mass to 50% by mass, or 20% by mass to 40% by mass.
  • the total content of the (A1) component and the (A2) component in the (A) component may be 80 to 100 mass%, 90 to 100 mass%, 95 to 100 mass%, or 100 mass% based on the total amount of the (A) component, from the viewpoint of improving solder heat resistance.
  • the (A1) component or the (A2) component is used alone, it can also be appropriately selected from the above range.
  • the mass ratio (A1/A2) may be 20/80 to 90/10, 20/80 to 80/20, or 30/70 to 70/30 from the viewpoint of improving solder heat resistance.
  • the photosensitive resin composition according to this embodiment contains an epoxy compound as component (B).
  • component (B) a compound having two or more epoxy groups can be used, and examples of the component (B) include a carboxy group contained in component (A) and an epoxy compound that is cured by heat or ultraviolet light.
  • the photosensitive resin composition according to this embodiment can form a permanent resist that is excellent in heat resistance, adhesion, and chemical resistance.
  • the component (B) may be used alone or in combination of two or more.
  • component (B) examples include bisphenol A type epoxy resins, bisphenol F type epoxy resins, hydrogenated bisphenol A type epoxy resins, brominated bisphenol A type epoxy resins, novolac type epoxy resins, bisphenol S type epoxy resins, biphenyl type epoxy resins, heterocyclic epoxy resins such as triglycidyl isocyanurate, and bixylenol type epoxy resins.
  • the epoxy equivalent of component (B) may be 100 g/eq or more, 130 g/eq or more, or 150 g/eq or more.
  • the epoxy equivalent of component (B) may be 450 g/eq or less, 400 g/eq or less, or 380 g/eq or less.
  • the epoxy equivalent of component (B) may be 100 g/eq to 450 g/eq, 130 g/eq to 400 g/eq, or 150 g/eq to 380 g/eq.
  • the epoxy equivalent can be measured according to JIS K 7236.
  • the content of component (B) in the photosensitive resin composition may be 2 mass% or more, 4 mass% or more, or 6 mass% or more, based on the total solid content of the photosensitive resin composition, from the viewpoint of crack resistance.
  • the content of component (B) may be 40 mass% or less, or 35 mass% or less.
  • the content of component (B) may be 2 to 40 mass%, 4 to 40 mass%, or 6 to 35 mass%.
  • the equivalent ratio of the epoxy groups contained in component (B) to the carboxy groups contained in component (A) is 1.25 to 7.50.
  • the equivalent ratio may be 1.50 or more, 1.75 or more, 1.95 or more, 2.00 or more, 2.20 or more, 2.40 or more, 2.50 or more, 3.00 or more, 3.50 or more, or 4.00 or more, and may be 7.40 or less, 7.30 or less, 7.20 or less, 7.10 or less, 7.00 or less, 6.75 or less, 6.50 or less, or 6.00 or less.
  • the equivalent ratio may be 2.00 to 7.50, 2.00 to 7.00, 2.50 to 7.00, or 4.00 to 7.00.
  • the content of the (B) component in the photosensitive resin composition is 1.25 to 7.50 equivalents of the epoxy group contained in the (B) component per equivalent of the carboxy group contained in the (A) component, but it may be 1.50 equivalents or more, 1.75 equivalents or more, 1.95 equivalents or more, 2.00 equivalents or more, 2.20 equivalents or more, 2.40 equivalents or more, 2.50 equivalents or more, 3.00 equivalents or more, 3.50 equivalents or more, or 4.00 equivalents or more, or 7.40 equivalents or less, 7.30 equivalents or less, 7.20 equivalents or less, 7.10 equivalents or less, 7.00 equivalents or less, 6.75 equivalents or less, 6.50 equivalents or less, or 6.00 equivalents or less.
  • the equivalent ratio of epoxy groups to carboxy groups can be calculated by the following formula.
  • Amount of carboxyl group (mmol) number of parts of component (A) ⁇ acid value of component (A) (mg KOH/g)/KOH molecular weight
  • Amount of epoxy group (mmol) number of parts of component (B)/epoxy equivalent of component (B) (g/eq) ⁇ 1000
  • Equivalent ratio (molar ratio) of epoxy group/carboxy group amount of epoxy group (mmol)/amount of carboxy group (mmol)
  • the photosensitive resin composition according to the present embodiment contains a photopolymerization initiator as the (C) component.
  • the (C) component is not particularly limited as long as it can polymerize the (D) component, which is a photopolymerizable compound.
  • Examples of the (C) component include an alkylphenone-based photopolymerization initiator, an acylphosphine oxide-based photopolymerization initiator, a compound having a thioxanthone skeleton, and a titanocene-based photopolymerization initiator.
  • an alkylphenone-based photopolymerization initiator a compound having a thioxanthone skeleton, or an acylphosphine oxide-based photopolymerization initiator may be used.
  • the (C) component may be used alone or in combination of two or more.
  • alkylphenone photopolymerization initiators include benzophenone, N,N,N',N'-tetraalkyl-4,4'-diaminobenzophenone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanone, 4,4'-bis(dimethylamino)benzophenone (Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4-methoxy-4'-dimethylaminobenzophenone.
  • benzophenone N,N,N',N'-tetraalkyl-4,4'-diaminobenzophenone
  • 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 2-methyl-1-[4-(methylthio)phenyl]-2
  • acylphosphine oxide photopolymerization initiators include (2,6-dimethoxybenzoyl)-2,4,4-pentylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, ethyl-2,4,6-trimethylbenzoylphenylphosphinenate, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, (2,5-dihydroxyphenyl)diphenylphosphine oxide, (p-hydroxyphenyl)diphenylphosphine oxide, bis(p-hydroxyphenyl)phenylphosphine oxide, tris(p-hydroxyphenyl)phosphine oxide, and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide.
  • Examples of compounds having a thioxanthone skeleton include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and dodecylthioxanthone.
  • the content of component (C) in the photosensitive resin composition is not particularly limited, but may be 0.2 to 15 mass%, 0.4 to 5 mass%, or 0.6 to 1 mass% based on the total solid content of the photosensitive resin composition. If the content of component (C) is 0.2 mass% or more, the exposed area is less likely to dissolve during development, and if it is 15 mass% or less, it is easier to suppress a decrease in heat resistance.
  • the photosensitive resin composition according to the present embodiment contains a photopolymerizable compound as component (D).
  • the component (D) is not particularly limited as long as it is a compound having a functional group exhibiting photopolymerizability.
  • the functional group exhibiting photopolymerizability include ethylenically unsaturated groups such as vinyl groups, allyl groups, propargyl groups, butenyl groups, ethynyl groups, phenylethynyl groups, maleimide groups, nadiimide groups, and (meth)acryloyl groups.
  • the component (D) may contain a compound having a (meth)acryloyl group.
  • Examples of the (D) component include hydroxyalkyl (meth)acrylate compounds such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; mono- or di-(meth)acrylate compounds of glycols such as ethylene glycol, methoxytetraethylene glycol, and polyethylene glycol; (meth)acrylamide compounds such as N,N-dimethyl (meth)acrylamide and N-methylol (meth)acrylamide; aminoalkyl (meth)acrylate compounds such as N,N-dimethylaminoethyl (meth)acrylate; hexanediol, trimethylolpropane, pentaerythritol, ditrimethylolpropane, and the like.
  • hydroxyalkyl (meth)acrylate compounds such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate
  • mono- or di-(meth)acrylate compounds of glycols
  • Examples of the (D) component include polyhydric alcohols such as propane, dipentaerythritol, and tris-hydroxyethyl isocyanurate, or polyhydric (meth)acrylate compounds of their ethylene oxide or propylene oxide adducts; (meth)acrylate compounds of ethylene oxide or propylene oxide adducts of phenolic compounds such as phenoxyethyl (meth)acrylate and polyethoxy di(meth)acrylate of bisphenol A; (meth)acrylate compounds of glycidyl ethers such as glycerin diglycidyl ether, trimethylolpropane triglycidyl ether, and triglycidyl isocyanurate; and melamine (meth)acrylate.
  • One type of component (D) can be used alone, or two or more types can be used in combination.
  • the content of component (D) in the photosensitive resin composition may be 0.1 to 10 mass%, 0.5 to 8 mass%, or 2 to 7 mass% based on the total solid content in the photosensitive resin composition. If the content of component (D) is 0.1 mass% or more, the exposed area is less likely to dissolve during development, and if it is 10 mass% or less, it is easier to improve heat resistance.
  • the photosensitive resin composition according to the present embodiment may further contain a pigment as component (E).
  • a pigment that develops a desired color when concealing wiring or the like can be used.
  • component (E) for example, known colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, carbon black, and naphthalene black can be mentioned.
  • component (E) one type can be used alone or two or more types can be used in combination.
  • the content of component (E) may be 2 to 30 mass %, 2.5 to 20 mass %, or 2.5 to 10 mass % based on the total solid content in the photosensitive resin composition, from the viewpoint of further concealing the wiring.
  • the photosensitive resin composition according to this embodiment contains an inorganic filler as component (F) for the purpose of improving the properties such as adhesion and hardness of the permanent resist.
  • component (F) include silica, alumina, zirconia, talc, aluminum hydroxide, calcium carbonate, barium sulfate, calcium sulfate, zinc oxide, magnesium titanate, and carbon.
  • the component (F) can be used alone or in combination of two or more.
  • the (F) component contains a silica filler having a vinyl group derived from a vinylsilane compound (hereinafter, sometimes referred to as a "vinyl group-containing silica filler") from the viewpoints of crack resistance, developability, and resolution.
  • the vinyl group-containing silica filler can be obtained by surface treating silica particles with a vinylsilane compound. The surface treatment can be carried out, for example, by adding a solution of the vinylsilane compound to the silica particles and stirring them.
  • the vinylsilane compound is not particularly limited as long as it is a silane compound having one or more vinyl groups bonded to a silicon atom.
  • the number of vinyl groups bonded to a silicon atom may be two or three.
  • the vinylsilane compound may have an alkoxy group, an acetoxy group, an alkyl group, etc., as a group other than the vinyl group bonded to the silicon atom.
  • Examples of the vinylsilane compound include vinylalkoxysilane and acetoxysilane in which the alkoxy group in the vinylalkoxysilane is replaced with an acetoxy group.
  • the vinylalkoxysilane is not particularly limited as long as it is a silane compound having a vinyl group bonded to a silicon atom and an alkoxy group bonded to a silicon atom.
  • the number of alkoxy groups bonded to the silicon atom may be two or three.
  • these alkoxy groups may be the same or different.
  • the number of carbon atoms of the alkoxy group bonded to the silicon atom may be 1 to 10, 1 to 6, 1 to 5, 1 to 4, or 1 to 3.
  • the vinylalkoxysilane may have an alkyl group bonded to the silicon atom. When the vinylalkoxysilane has an alkyl group bonded to the silicon atom, the number of carbon atoms of the alkyl group may be 1 to 10, 1 to 6, 1 to 5, 1 to 4, or 1 to 3.
  • vinyl alkoxysilanes examples include vinyl trialkoxysilanes having three alkoxy groups bonded to silicon atoms, such as vinyl trimethoxysilane, vinyl triethoxysilane, and vinyl triisopropoxysilane; vinyl dialkoxysilanes having two alkoxy groups bonded to silicon atoms, such as vinyl dimethoxysilane, vinyl diethoxysilane, and vinyl diisopropoxysilane; and vinyl alkoxysilanes having one alkoxy group bonded to silicon atoms, such as vinyl monomethoxysilane, vinyl monoethoxysilane, and vinyl monoisopropoxysilane. These vinyl alkoxysilanes may be used alone or in combination of two or more.
  • vinylacetoxysilanes examples include vinyltriacetoxysilane, vinyldiacetoxysilane, and vinylmonoacetoxysilane.
  • the (F) component may contain barium sulfate from the viewpoints of solder heat resistance, crack resistance, and pressure cooker resistance (PCT resistance).
  • the (F) component may contain alumina from the viewpoint of improving the aggregation prevention effect.
  • the average particle size of component (F) may be 0.1 to 20 ⁇ m, 0.1 to 10 ⁇ m, 0.1 to 5 ⁇ m, or 0.1 to 1 ⁇ m. If the average particle size is 20 ⁇ m or less, the deterioration of the insulating reliability of the permanent resist can be further suppressed.
  • the content of the (F) component may be 10 to 80 mass%, 15 to 70 mass%, 20 to 60 mass%, 25 to 50 mass%, or 30 to 45 mass% based on the total solid content of the photosensitive resin composition.
  • the content of the (F) component may be 10 mass% or more, 15 mass% or more, 20 mass% or more, 25 mass% or more, or 30 mass% or more, and may be 80 mass% or less, 70 mass% or less, 60 mass% or less, 50 mass% or less, or 45 mass% or less.
  • the content of the vinyl group-containing silica filler may be 5 to 60 mass%, 15 to 55 mass%, 20 to 50 mass%, or 25 to 45 mass%, based on the total solid content of the photosensitive resin composition.
  • the content of the vinyl group-containing silica filler may be 5 mass% or more, 15 mass% or more, 20 mass% or more, or 25 mass% or more, and may be 60 mass% or less, 55 mass% or less, 50 mass% or less, or 45 mass% or less.
  • the content of the vinyl group-containing silica filler in component (F) may be 50% by mass to 100% by mass, 55% by mass to 100% by mass, 60% by mass to 100% by mass, or 65% by mass to 100% by mass based on the total amount of component (F) from the viewpoints of developability, resolution, and crack resistance.
  • the content of barium sulfate may be 5 to 30 mass%, 5 to 25 mass%, or 5 to 20 mass% based on the total solid content of the photosensitive resin composition. If the content of barium sulfate is within the above range, the solder heat resistance and PCT resistance can be further improved.
  • the photosensitive resin composition according to the present embodiment may further contain a curing agent as component (G).
  • a curing agent examples include a compound that cures by itself with heat, ultraviolet light, or the like, or a compound that cures by reacting with a carboxyl group or a hydroxyl group of component (A) with heat, ultraviolet light, or the like.
  • Examples of the (G) component include thermosetting compounds such as melamine compounds and oxazoline compounds.
  • Examples of the melamine compounds include triaminotriazine, hexamethoxymelamine, and hexabutoxylated melamine.
  • the (G) component can be used alone or in combination of two or more types.
  • component (G) When component (G) is used, its content may be 2 to 40 mass%, 3 to 30 mass%, or 5 to 20 mass% based on the total solid content of the photosensitive resin composition. When the content of component (G) is within the above range, the heat resistance of the formed permanent resist can be further improved while maintaining better developability.
  • the photosensitive resin composition according to this embodiment may be used in combination with a curing accelerator to accelerate the curing of component (D) in order to further improve the properties of the permanent resist, such as heat resistance, adhesion, and chemical resistance.
  • the curing accelerator examples include imidazole derivatives such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 2-phenylimidazole, and 2-phenyl-4-methyl-5-hydroxymethylimidazole; guanamines such as acetoguanamine and benzoguanamine; polyamines such as diaminodiphenylmethane, m-phenylenediamine, m-xylylenediamine, diaminodiphenylsulfone, dicyandiamide, urea, urea derivatives, melamine, and polybasic hydrazides; organic acid salts or epoxy adducts thereof; amine complexes of boron trifluoride; and triazine derivatives such as ethyldiamino-S-triazine, 2,4-diamino-S-triazine, and 2,4-diamino-6
  • a curing accelerator When a curing accelerator is used, its content may be 0.01 to 20 mass % or 0.1 to 10 mass % based on the total solid content of the photosensitive resin composition from the viewpoint of improving reliability.
  • the photosensitive resin composition according to this embodiment may further contain an elastomer as component (H).
  • Component (H) may be used when the photosensitive resin composition according to this embodiment is used for a semiconductor package substrate.
  • thermoplastic elastomers such as styrene-based elastomers, olefin-based elastomers, urethane-based elastomers, polyester-based elastomers, polyamide-based elastomers, acrylic-based elastomers, and silicone-based elastomers.
  • Thermoplastic elastomers are composed of hard segment components that contribute to heat resistance and strength, and soft segment components that contribute to flexibility and toughness.
  • the (H) component can be used alone or in combination of two or more types.
  • urethane-based elastomer a compound composed of a hard segment formed from a low molecular weight (short chain) diol and a diisocyanate, and a soft segment formed from a high molecular weight (long chain) diol and a diisocyanate can be used.
  • low molecular weight diols include ethylene glycol, propylene glycol, 1,4-butanediol, and bisphenol A.
  • high molecular weight diols examples include polypropylene glycol, polytetramethylene oxide, poly(1,4-butylene adipate), poly(ethylene-1,4-butylene adipate), polycaprolactone, poly(1,6-hexylene carbonate), and poly(1,6-hexylene-neopentylene adipate).
  • the number average molecular weight (Mn) of the low molecular weight diol may be 48 to 500.
  • the Mn of the high molecular weight diol may be 500 to 10,000.
  • Examples of commercially available urethane elastomers include PANDEX T-2185 and T-2983N (manufactured by DIC Corporation), and Miractoran E790 (manufactured by Nippon Miractoran Co., Ltd.).
  • polyester-based elastomers compounds obtained by polycondensation of dicarboxylic acids or their derivatives with diol compounds or their derivatives can be used.
  • dicarboxylic acids include aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, and naphthalenedicarboxylic acid, and aromatic dicarboxylic acids in which the hydrogen atoms of the aromatic nuclei are substituted with methyl groups, ethyl groups, phenyl groups, and the like; aliphatic dicarboxylic acids having 2 to 20 carbon atoms such as adipic acid, sebacic acid, and dodecanedicarboxylic acid; and alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid.
  • diol compounds include aliphatic or alicyclic diols such as ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,10-decanediol, and 1,4-cyclohexanediol, as well as dihydric phenols represented by the following formula (IV):
  • Y represents an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 4 to 8 carbon atoms, an ether group, a thioether group, a sulfonyl group, or a single bond
  • R1 and R2 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 12 carbon atoms
  • l and m each independently represent an integer of 0 to 4
  • p is 0 or 1.
  • the alkylene group and cycloalkylene group may be linear or branched, and may be substituted with a halogen atom, an alkyl group, an aryl group, an aralkyl group, an amino group, an amide group, an alkoxy group, or the like.
  • dihydric phenol represented by formula (IV) examples include bisphenol A, bis-(4-hydroxyphenyl)methane, bis-(4-hydroxy-3-methylphenyl)propane, and resorcinol. These compounds can be used alone or in combination of two or more.
  • polyester elastomers multiblock copolymers in which aromatic polyester (e.g., polybutylene terephthalate) parts are the hard segment components and aliphatic polyester (e.g., polytetramethylene glycol) parts are the soft segment components.
  • aromatic polyester e.g., polybutylene terephthalate
  • aliphatic polyester e.g., polytetramethylene glycol
  • polyester elastomers There are various grades of polyester elastomers depending on the type, ratio, and molecular weight of the hard and soft segments.
  • polyester elastomers include, for example, Hytrel (manufactured by DuPont-Toray Industries, Inc., "Hytrel” is a registered trademark), Pelprene (manufactured by Toyobo Co., Ltd., “Pelprene” is a registered trademark), and Espel (manufactured by Showa Denko Materials KK, "Espel” is a registered trademark).
  • the acrylic elastomer may be a compound containing an acrylic acid ester-based structural unit as the main component.
  • acrylic acid esters include ethyl acrylate, butyl acrylate, methoxyethyl acrylate, and ethoxyethyl acrylate.
  • the acrylic elastomer may be a compound obtained by copolymerizing an acrylic acid ester with acrylonitrile, or may be a compound obtained by further copolymerizing a monomer having a functional group that serves as a crosslinking point. Examples of monomers having a functional group include glycidyl methacrylate and allyl glycidyl ether.
  • acrylic elastomers examples include acrylonitrile-butyl acrylate copolymer, acrylonitrile-butyl acrylate-ethyl acrylate copolymer, and acrylonitrile-butyl acrylate-glycidyl methacrylate copolymer.
  • a rubber-modified epoxy resin may be used as an elastomer other than the thermoplastic elastomer.
  • the rubber-modified epoxy resin may be obtained, for example, by modifying a part or all of the epoxy groups of the above-mentioned bisphenol F type epoxy resin, bisphenol A type epoxy resin, salicylaldehyde type epoxy resin, phenol novolac type epoxy resin, or cresol novolac type epoxy resin with a butadiene-acrylonitrile rubber modified at both ends with a carboxyl group, a silicone rubber modified at both ends with an amino group, or the like.
  • elastomers from the viewpoint of shear adhesion, a butadiene-acrylonitrile copolymer modified at both ends with a carboxyl group, or Espel (manufactured by Showa Denko Materials Co., Ltd., Espel 1612, 1620), a polyester-based elastomer having hydroxyl groups, may be used.
  • the content of component (H) may be 2 to 40 parts by weight, 4 to 30 parts by weight, 10 to 25 parts by weight, or 15 to 22 parts by weight, per 100 parts by weight of component (A).
  • the photosensitive resin composition according to the present embodiment may be mixed with a diluent such as an organic solvent to adjust the viscosity, if necessary.
  • a diluent such as an organic solvent
  • the organic solvent include ketones such as methyl ethyl ketone and cyclohexanone, aromatic hydrocarbons such as toluene, xylene, and tetramethylbenzene, glycol ethers such as methyl cellosolve, butyl cellosolve, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol diethyl ether, and triethylene glycol monoethyl ether, esters such as ethyl acetate, butyl acetate, butyl cellosolve acetate, and carbitol acetate, aliphatic hydrocarbons such as octane and decane
  • the content of the diluent in the photosensitive resin composition may be 10 to 50% by mass, 20 to 40% by mass, or 25 to 35% by mass.
  • the photosensitive resin composition according to this embodiment may further contain various additives as necessary.
  • additives include polymerization inhibitors such as hydroquinone, methylhydroquinone, hydroquinone monomethyl ether, catechol, and pyrogallol; thickeners such as bentone and montmorillonite; silicone-based, fluorine-based, or vinyl resin-based defoamers; silane coupling agents; and flame retardants such as brominated epoxy compounds, acid-modified brominated epoxy compounds, antimony compounds, phosphate compounds of phosphorus compounds, aromatic condensed phosphate esters, and halogen-containing condensed phosphate esters.
  • the photosensitive resin composition according to this embodiment can be prepared by uniformly mixing the above-mentioned components using a roll mill, bead mill, or the like.
  • the photosensitive element according to the present embodiment includes a support film and a photosensitive layer containing the above-mentioned photosensitive resin composition.
  • Fig. 1 is a cross-sectional view showing a schematic diagram of the photosensitive element according to the present embodiment. As shown in Fig. 1, the photosensitive element 1 includes a support film 10 and a photosensitive layer 20 formed on the support film 10.
  • the photosensitive element 1 can be produced, for example, by applying the photosensitive resin composition according to this embodiment onto a support film 10 by a known method such as reverse roll coating, gravure roll coating, comma coating, or curtain coating, and then drying the coating to form a photosensitive layer 20.
  • the support film examples include polyester films such as polyethylene terephthalate and polybutylene terephthalate, and polyolefin films such as polypropylene and polyethylene.
  • the thickness of the support film may be, for example, 5 to 100 ⁇ m.
  • the thickness of the photosensitive layer may be, for example, 10 to 50 ⁇ m, 15 to 40 ⁇ m, or 20 to 30 ⁇ m.
  • the coating film can be dried using hot air drying, far infrared rays, or near infrared rays.
  • the drying temperature may be 60 to 120°C, 70 to 110°C, or 80 to 100°C.
  • the drying time may be 1 to 60 minutes, 2 to 30 minutes, or 5 to 20 minutes.
  • the photosensitive layer 20 may further include a protective film 30 covering the photosensitive layer 20.
  • the photosensitive element 1 may also have the protective film 30 laminated on the surface of the photosensitive layer 20 opposite the surface that contacts the support film 10.
  • the protective film 30 may be, for example, a polymer film such as polyethylene or polypropylene.
  • the protective film may be the same film as the support film, or may be a different film.
  • the printed wiring board according to the present embodiment includes a permanent resist including a cured product of the photosensitive resin composition according to the present embodiment. Since the printed wiring board according to the present embodiment includes a permanent resist including a cured product of the photosensitive resin composition according to the present embodiment, the occurrence of cracks in the permanent resist can be reduced.
  • the method for manufacturing a printed wiring board includes the steps of forming a photosensitive layer on a substrate using the above-mentioned photosensitive resin composition or the above-mentioned photosensitive element, exposing and developing the photosensitive layer to form a resist pattern, and curing the resist pattern to form a permanent resist. An example of each step is described below.
  • a metal-clad laminate such as a copper-clad laminate is prepared as a substrate, and a photosensitive layer is formed on the substrate.
  • the photosensitive resin composition may be applied to the substrate by a method such as screen printing, spraying, roll coating, curtain coating, or electrostatic coating, and the formed coating film may be dried at 60 to 110°C to form a photosensitive layer.
  • the thickness of the coating film may be 10 to 200 ⁇ m, 15 to 150 ⁇ m, 20 to 100 ⁇ m, or 23 to 50 ⁇ m.
  • the photosensitive layer may be formed by thermally laminating the photosensitive layer of the photosensitive element onto the substrate using a laminator.
  • a negative mask is brought into contact with the photosensitive layer directly or through a transparent film such as a support film, and the layer is exposed to active light, and then the unexposed areas are dissolved and removed with a developer to form a resist pattern.
  • active light include electron beams, ultraviolet rays, and X-rays, and preferably ultraviolet rays.
  • Examples of light sources that can be used include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, and halogen lamps.
  • the exposure dose may be 10 to 2000 mJ/cm 2 , 100 to 1500 mJ/cm 2 , or 300 to 1000 mJ/cm 2.
  • Examples of development methods include dipping and spraying. Examples of development methods that can be used include alkaline aqueous solutions of potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, tetramethylammonium hydroxide, and the like.
  • the formed resist pattern is subjected to at least one of post-exposure and post-heating to sufficiently harden it to form a permanent resist.
  • the exposure dose of the post-exposure may be 100 to 5000 mJ/cm 2 , 500 to 2000 mJ/cm 2 , or 700 to 1500 mJ/cm 2 .
  • the heating temperature of the post-heating may be 100 to 200° C., 120 to 180° C., or 135 to 165° C.
  • the heating time of the post-heating may be 5 minutes to 12 hours, 10 minutes to 6 hours, or 30 minutes to 2 hours.
  • the thickness of the permanent resist may be 10 to 50 ⁇ m, 15 to 40 ⁇ m, or 20 to 30 ⁇ m.
  • the permanent resist according to this embodiment can be used as an interlayer insulating layer or a surface protective layer of a semiconductor element.
  • a semiconductor element having an interlayer insulating layer or a surface protective layer formed from a cured film of the above-mentioned photosensitive resin composition, and an electronic device including the semiconductor element can be produced.
  • the semiconductor element may be, for example, a memory, a package, etc. having a multilayer wiring structure, a rewiring structure, etc.
  • Examples of electronic devices include mobile phones, smartphones, tablet terminals, personal computers, and hard disk suspensions.
  • Photosensitive resin composition The components were mixed according to the amounts shown in Tables 1 and 2 and kneaded in a three-roll mill. Carbitol acetate was then added so that the solids concentration was 70% by mass to obtain a photosensitive resin composition.
  • Tables 1 and 2 show the parts by mass of the solids of components (A) to (F) based on the total solids content of the photosensitive resin composition.
  • A-1 Acid-modified vinyl group-containing resin obtained in Synthesis Example 1
  • A-2 An acid-modified vinyl group-containing resin (acid value: 42.4 mg KOH/ g ) obtained by acrylate of the glycidyl group of a novolac epoxy resin (product name: UE-EXP-3165; manufactured by DIC Corporation) having a structure in which R 13 is a hydrogen atom and Y 5 is a glycidyl group in the formula (III'), and modifying the hydroxyl group with tetrahydrophthalic anhydride.
  • B-1 Bisphenol A type epoxy resin (product name: YD-8125; manufactured by Nippon Steel Chemical & Material Co., Ltd.; epoxy equivalent: 173 g/eq)
  • B-2 Novolac-type multifunctional epoxy resin (product name: RE-306; manufactured by Nippon Kayaku Co., Ltd.; epoxy equivalent: 270 g/eq)
  • B-3 Bisphenol A type novolac epoxy resin (product name: jER157S70; manufactured by Mitsubishi Chemical Corporation; epoxy equivalent: 210 g/eq)
  • B-4 Bisphenol F type epoxy resin (product name: EXA-9580; manufactured by DIC Corporation; epoxy equivalent: 360 g/eq)
  • B-5 tetrafunctional epoxy resin (product name: jER1031S; manufactured by Mitsubishi Chemical Corporation; epoxy equivalent: 200 g/eq)
  • C-1 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanone (trade name: Irgacure 907; manufactured by BASF)
  • F-1 Barium sulfate particles (product name: B34; manufactured by Sakai Chemical Industry Co., Ltd.; average particle size: 0.3 ⁇ m)
  • F-2 Silica filler having a vinyl group derived from a vinylsilane compound, obtained by adding 1 g of 1 mass% vinyltrimethoxysilane (product name: KBM-1003; manufactured by Shin-Etsu Silicone Co., Ltd.) to 100 g of untreated silica particles (product name: SO-C2; manufactured by Admattex Co., Ltd., average particle size: 0.5 ⁇ m) and stirring at 80 ° C. for 30 minutes.
  • F-3 Silica filler having an epoxy group, obtained in the same manner as F-2, except that vinyltrimethoxysilane was changed to 3-glycidoxypropyltrimethoxysilane (product name: KBM-403; manufactured by Shin-Etsu Silicone Co., Ltd.).
  • F-4 Silica filler having an epoxy group, obtained in the same manner as F-2, except that vinyltrimethoxysilane was changed to 3-glycidoxypropyltrimethoxysilane (product name: KBM-403; manufactured by Shin-Etsu Silicone Co., Ltd.).
  • F-5 Silica filler having a phenylamino group obtained in the same manner as F-2, except that vinyltrimethoxysilane was changed to N-phenyl-3-aminopropyltrimethoxysilane (product name: KBM-573; manufactured by Shin-Etsu Silicone Co., Ltd.)
  • F-6 Untreated silica particles (product name: SO-C2; manufactured by Admattex Co., Ltd., average particle size: 0.5 ⁇ m)
  • the equivalent ratio of epoxy groups in component (B) to carboxy groups in component (A) was 1.50.
  • the photosensitive resin composition was used to carry out the evaluations under the conditions shown below. The results are shown in Tables 1 and 2.
  • Test Piece 1 The photosensitive resin compositions of the examples and comparative examples were applied to a copper-clad laminate substrate having a thickness of 0.6 mm (a copper-clad laminate substrate having copper foil arranged on a glass epoxy material, manufactured by Showa Denko Materials Co., Ltd., product name: MCL-E-67) by screen printing so that the thickness after drying was 35 ⁇ m, and then dried at 80 ° C. for 20 minutes using a hot air circulation dryer to form a photosensitive layer. Next, a negative mask having a predetermined pattern was attached to the obtained photosensitive layer, and exposed to an exposure amount of 600 mJ / cm 2 using an ultraviolet exposure device.
  • a copper-clad laminate substrate having a thickness of 0.6 mm a copper-clad laminate substrate having copper foil arranged on a glass epoxy material, manufactured by Showa Denko Materials Co., Ltd., product name: MCL-E-67
  • the layer was spray-developed with a 1 mass % aqueous sodium carbonate solution at a pressure of 1.765 ⁇ 10 5 Pa for 60 seconds, and the unexposed portion was dissolved and developed.
  • the layer was exposed to an exposure amount of 1000 mJ / cm 2 using an ultraviolet exposure device and heated at 150 ° C. for 1 hour to prepare a test piece 1 having a permanent resist.
  • Crack resistance A temperature cycle test was carried out on the test piece 1, with one cycle consisting of 30 minutes at -65°C and 30 minutes at 150°C. The permanent resist was observed visually and with an optical microscope at the 1000th, 2000th and 3000th cycles, and the crack resistance was evaluated according to the following criteria. S: No cracks were observed after 3000 cycles. A: No cracks were observed after 2000 cycles, but cracks were observed after 3000 cycles. B: No cracks were observed after 1000 cycles, but cracks were observed after 2000 cycles. C: Cracks were observed after 1000 cycles.
  • the photosensitive resin compositions of the examples and comparative examples were applied to a copper-clad laminate substrate (manufactured by Showa Denko Materials Co., Ltd., product name: MCL-E-67) by screen printing so that the thickness after drying was 15 ⁇ m, and then dried at 75 ° C. for 30 minutes using a hot air circulation dryer to form a photosensitive layer.
  • the obtained photosensitive layer was irradiated with ultraviolet light at an integrated exposure dose of 100 mJ / cm 2 through a negative mask having a 1 ⁇ 1 cm square area dotted with light non-transmitting parts of 80 ⁇ m in diameter.
  • test piece 2 was spray-developed with a 1 mass % aqueous sodium carbonate solution at a pressure of 1.8 kgf / cm 2 for 60 seconds, and the unexposed parts were dissolved and developed to prepare test piece 2. Thereafter, the opening of test piece 2 was observed at 10,000 times using an SEM (manufactured by High Technologies Corporation, model number: S4200, field emission scanning electron microscope), and the developability was evaluated based on the remaining state of the resist residue according to the following criteria. S: 0 residues were found in one visual field. A: There was 1 or more but less than 5 residues in one visual field. B: There were 5 or more but less than 10 residues in one visual field. C: 10 or more residues were found in one visual field.
  • Test piece 3 having a cured film on which an opening pattern of a predetermined size was formed was prepared in the same manner as in Test piece 1, except that a negative mask having an opening pattern of a predetermined size (opening diameter size: 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 150, 200 ⁇ m) was used as the negative mask.
  • Test piece 3 was observed using an optical microscope, and the resolution was evaluated according to the following criteria.
  • C The minimum mask opening diameter exceeded 55 ⁇ m.
  • solder heat resistance A water-soluble flux was applied to the test piece 1, and the test piece was immersed for 10 seconds in a solder bath at 265° C. This constitutes one cycle, and after six cycles were repeated, the appearance of the permanent resist was visually observed and the solder heat resistance was evaluated according to the following criteria.
  • C Six or more lifts or blisters of the coating film occurred within a 30 cm x 30 cm area of the permanent resist.
  • the test piece 1 was immersed in a 10% by weight aqueous hydrochloric acid solution at room temperature for 30 minutes, and after checking whether there was any abnormality in the appearance of the permanent resist, a peeling test was performed using cellophane tape. Acid resistance was evaluated according to the following criteria. A: The appearance of the permanent resist was normal and no peeling occurred. B: Only a slight change occurred in the appearance of the permanent resist. C: The appearance of the permanent resist was abnormal or peeling occurred.
  • Test piece 1 was immersed in a 5% by mass aqueous solution of sodium hydroxide at room temperature for 30 minutes, and after checking whether there was any abnormality in the appearance of the permanent resist, a peeling test was performed using cellophane tape. The alkali resistance was evaluated according to the following criteria. A: The appearance of the permanent resist was normal and no peeling occurred. B: Only a slight change occurred in the appearance of the permanent resist. C: The appearance of the permanent resist was abnormal or peeling occurred.
  • Tables 1 and 2 confirm that the photosensitive resin compositions of the examples can form permanent resists with excellent crack resistance and have excellent developability.
  • Each photosensitive resin composition was diluted with methyl ethyl ketone, coated on a polyethylene terephthalate (PET) film, and dried at 90° C. for 10 minutes to form a photosensitive layer having a thickness of 25 ⁇ m.
  • PET polyethylene terephthalate
  • a PET film was attached as a protective film onto the photosensitive layer to prepare a photosensitive element.
  • the photosensitive layer of the photosensitive element was used to evaluate crack resistance, developability, resolution, solder heat resistance, solvent resistance, acid resistance, alkali resistance, and electrical insulation, and the results obtained were similar to those obtained when the photosensitive resin composition shown in Tables 1 and 2 was used.
  • the test specimens using the photosensitive layer were prepared in the same manner as test specimens 1 to 4 above, except that the protective film was peeled off from the photosensitive element, the photosensitive layer of the photosensitive element was thermally laminated onto the substrate, and then the support film was peeled off to form the photosensitive layer on the substrate.

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PCT/JP2022/037335 2022-10-05 2022-10-05 感光性樹脂組成物、感光性エレメント、プリント配線板及びプリント配線板の製造方法 Ceased WO2024075229A1 (ja)

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US18/859,679 US20250258430A1 (en) 2022-10-05 2022-10-05 Photosensitive resin composition, photosensitive element, printed wiring board, and method for producing printed wiring board
KR1020257005438A KR20250087516A (ko) 2022-10-05 2022-10-05 감광성 수지 조성물, 감광성 엘리먼트, 프린트 배선판 및 프린트 배선판의 제조 방법
CN202280095381.9A CN119096198A (zh) 2022-10-05 2022-10-05 感光性树脂组合物、感光性元件、印刷线路板及印刷线路板的制造方法
TW112135469A TW202417522A (zh) 2022-10-05 2023-09-18 感光性樹脂組成物、感光性元件、印刷配線板及印刷配線板之製造方法

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Citations (5)

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Publication number Priority date Publication date Assignee Title
JP2004217869A (ja) * 2003-01-17 2004-08-05 Dainippon Ink & Chem Inc エポキシ樹脂組成物、エポキシ樹脂硬化剤
JP2015013950A (ja) * 2013-07-05 2015-01-22 ナガセケムテックス株式会社 エポキシ樹脂組成物
JP2019144681A (ja) * 2018-02-16 2019-08-29 東洋インキＳｃホールディングス株式会社 タッチパネルデバイス、及びタッチパネル
JP2022025366A (ja) * 2020-07-29 2022-02-10 太陽インキ製造株式会社 ドライフィルム、ドライフィルムセット、その硬化物および電子部品
JP2022107466A (ja) * 2021-01-08 2022-07-21 互応化学工業株式会社 感光性樹脂組成物、ドライフィルム、硬化物及びプリント配線板

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JP4240885B2 (ja) 2001-12-28 2009-03-18 日立化成工業株式会社 フレキシブル配線板の保護膜を形成する方法
JP2011240930A (ja) 2010-05-14 2011-12-01 Three M Innovative Properties Co 包装袋

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004217869A (ja) * 2003-01-17 2004-08-05 Dainippon Ink & Chem Inc エポキシ樹脂組成物、エポキシ樹脂硬化剤
JP2015013950A (ja) * 2013-07-05 2015-01-22 ナガセケムテックス株式会社 エポキシ樹脂組成物
JP2019144681A (ja) * 2018-02-16 2019-08-29 東洋インキＳｃホールディングス株式会社 タッチパネルデバイス、及びタッチパネル
JP2022025366A (ja) * 2020-07-29 2022-02-10 太陽インキ製造株式会社 ドライフィルム、ドライフィルムセット、その硬化物および電子部品
JP2022107466A (ja) * 2021-01-08 2022-07-21 互応化学工業株式会社 感光性樹脂組成物、ドライフィルム、硬化物及びプリント配線板

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