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WO2001022165A1 - Compositions a base de resine photosensibles, element photosensible contenant ces compositions, procede de production d'un motif de reserve et procede de production de carte a circuit imprime - Google Patents

Compositions a base de resine photosensibles, element photosensible contenant ces compositions, procede de production d'un motif de reserve et procede de production de carte a circuit imprime Download PDF

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Publication number
WO2001022165A1
WO2001022165A1 PCT/JP2000/006353 JP0006353W WO0122165A1 WO 2001022165 A1 WO2001022165 A1 WO 2001022165A1 JP 0006353 W JP0006353 W JP 0006353W WO 0122165 A1 WO0122165 A1 WO 0122165A1
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WO
WIPO (PCT)
Prior art keywords
group
resin composition
photosensitive resin
carbon atoms
component
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Ceased
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PCT/JP2000/006353
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English (en)
Japanese (ja)
Inventor
Takahiro Hidaka
Michiko Natori
Yasuharu Murakami
Yukiko Muramatsu
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Resonac Corp
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Hitachi Chemical Co Ltd
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Priority to JP2001525474A priority Critical patent/JP3765272B2/ja
Priority to AU73150/00A priority patent/AU7315000A/en
Publication of WO2001022165A1 publication Critical patent/WO2001022165A1/fr
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
    • G03F7/038—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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

Definitions

  • the present invention relates to a photosensitive resin composition, a photosensitive element using the same, a method for producing a resist pattern, and a method for producing a printed wiring board. Background technology
  • the printed wiring board is formed by laminating the photosensitive element on a copper substrate, exposing it to a pattern, removing the cured part with a developing solution, performing etching or plating, forming a pattern, and then curing. It is manufactured by a method that removes the part from the substrate.
  • a photosensitive resin composition having a high sensitivity and a low bathing stain is desired, and these characteristics depend on the type and amount of the photoinitiator used. Is what you do.
  • High-sensitivity photoinitiators are described in German Patent No. 2,027,467, European Patent Publication No. 11,787, European Patent Publication No. 220, Although described in Patent Publication No. 5889 and Japanese Patent Application Laid-Open No. 6-69631, these tend to have plating bath contaminating properties.
  • a highly sensitive photosensitive resin composition obtained by combining 2,4,5-triene diimidazo monomer, a photoinitiator with low plating bath contamination, and a hydrogen-donating compound is disclosed in US Pat. Although it is described in the specification of No. 3,479,185, if the required sensitivity is adjusted, increasing the amount of 2,4,5-triphenylimidazol-l-mer will increase the resist.
  • an object of the present invention is to provide a photosensitive resin composition which is excellent in resolution, adhesion, sensitivity, peeling properties and the like, and has low plating bath contamination. Another object is resolution, adhesion, sensitivity, release properties, low with bath fouling is to provide an excellent photosensitive element workability and productivity and the like: Another object is resolved An object of the present invention is to provide a method for producing a resist pattern excellent in properties, adhesion, sensitivity, peeling properties, low-contamination bath contamination, workability, and productivity. Still another object is to provide a method for producing a printed wiring board which is excellent in resolution, adhesion, sensitivity, peeling properties, low plating bath contamination, workability, and productivity.
  • a photosensitive resin composition comprises (A) a binder polymer, (B 1) a photopolymerizable compound having at least one polymerizable cyclic ether group in a molecule, and (C 1) a photoacid generator.
  • a photosensitive resin composition is provided.
  • (A) a binder polymer, (B 2) a photopolymerizable compound having at least one polymerizable ethylenically unsaturated group in a molecule, and (C 1) a photoacid generator Resin composition containing Things are provided.
  • a photosensitive resin composition comprising a photopolymerizable compound having a polymerizable ethylenically unsaturated group and (C 2) a radical polymerization initiator is provided.
  • a photosensitive element in which a resist layer comprising the photosensitive resin composition according to the present invention is formed on a support.
  • a method for manufacturing a resist pattern comprising the following steps:
  • i i a step of irradiating with an actinic ray through a mask pattern or directly drawing and exposing a laser, and photo-curing the resist layer in an exposed portion;
  • a method for manufacturing a printed wiring board comprising the following steps:
  • a photosensitive element having a resist layer comprising the photosensitive resin composition according to the present invention formed on a support, a circuit element having a layer to be processed on a surface, a circuit forming substrate; Laminating so as to be in close contact with the surface of the layer to be processed of the forming substrate;
  • i i a step of irradiating with an actinic ray through a mask pattern or directly drawing and exposing a laser, and photo-curing the resist layer in an exposed portion;
  • FIG. 1 is a schematic view showing one embodiment of a photosensitive element.
  • FIG. 2 is a schematic view showing steps of a method for manufacturing a resist pattern.
  • 3 and 4 are schematic views showing steps of a method for manufacturing a printed wiring board.
  • BEST MODE FOR CARRYING OUT THE INVENTION hereinafter, embodiments of the present invention will be described in detail.
  • (meth) acrylic acid means acrylic acid and its corresponding methacrylic acid
  • (meth) acrylate means acrylate and its corresponding methacrylate
  • (meth) acryloyl group means It means an acryloyl group and its corresponding methacryloyl group.
  • the photosensitive resin composition according to the present invention has three independent features.
  • the first feature is that it comprises (A) a binder polymer, (B 1) a photopolymerizable compound having at least one polymerizable cyclic ether group in a molecule, and (C 1) a photoacid generator. It is to become.
  • the second feature is that it contains (A) a binder polymer, (B 2) a photopolymerizable compound having at least one polymerizable ethylenically unsaturated group in a molecule, and (C 1) a photoacid generator. It is becoming.
  • the third feature is that (A) a binder polymer, (B 1) a photopolymerizable compound having at least one polymerizable cyclic ether group in a molecule, and (B 2) at least one polymerizable compound in a molecule.
  • the first feature it is possible to provide a photosensitive resin composition having excellent resolution, adhesion, sensitivity, and peeling properties, and having low plating bath contamination.
  • adhesion, sensitivity, A photosensitive resin composition having excellent chemical resistance and flexibility and low plating bath contamination can be provided.
  • a photosensitive resin composition having excellent resolution, sensitivity, pattern shape, and release characteristics can be provided.
  • the component (B 1) functions as a plasticizer for radical polymerization and softens the system, resulting in a resin composition having a particularly good shape, and promotes radical polymerization. Since the crosslink density does not increase, the effect of shortening the stripping time of the cured product is obtained.
  • the radical generated from the (C 1) component contributes to the radical polymerization.
  • a resin composition is obtained.
  • cationic polymerization occurs together with radical polymerization, and a resin composition having particularly excellent sensitivity can be obtained.
  • binder polymer as the component (A) examples include an acrylic resin, a styrene resin, an epoxy resin, an amide resin, an amide epoxy resin, an alkyd resin, and a phenol resin.
  • Acrylic resins are preferred from the viewpoint that they can be developed with an alkaline aqueous solution. These can be used alone or in combination of two or more. Further, if necessary, these binder polymers may have a photosensitive group.
  • the binder polymer can be produced, for example, by radically polymerizing a polymerizable monomer.
  • polymerizable monomer examples include, for example, a polymerizable styrene derivative having a substituted mono- or aromatic ring such as styrene, vinyltoluene and hexamethylstyrene, acrylamide such as diacetone acrylamide, acrylonitrile, and vinyl.
  • Vinyl alcohols such as n-butyl ether Ester of coal, alkyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, dimethylaminoethyl (meth) acrylate, getylaminoethyl (meth) acrylate, (meth) acrylic acid Glycidyl ester, 2,2,2-Trifluoroethyl (meth) acrylate, 2,2,3,3-Tetrafluoropropyl (meth) acrylate, (meth) acrylic acid, ⁇ -bromo (meth) acrylic acid, (Meth) acrylic acid, / 3-furyl (meth) acrylic acid, 3-styrylyl (meth) acrylic acid, maleic acid, maleic anhydride, monomethyl maleate, monoethyl maleate, monoisopropyl maleate, etc. Acid monoester, fumaric acid, cinnamate, ⁇ - Examples include anookeic acid, it
  • alkyl (meth) acrylate examples include those represented by the general formula (3):
  • R 6 represents a hydrogen atom or a methyl group
  • R 7 represents an alkyl group having 1 to 12 carbon atoms
  • Examples of the alkyl group having 1 to 12 carbon atoms represented by R 7 in the general formula (3) include a methyl group, an ethyl group, a propyl group, a butyl group, a benzyl group, a hexyl group, a heptyl group, Examples thereof include an octyl group, a nonyl group, a decyl group, a pendecyl group, a dodecyl group, and structural isomers thereof.
  • Examples of the monomer represented by the general formula (3) include (meth) acrylic acid methyl ester, (meth) acrylic acid ethyl ester, (meth) acrylic acid propyl ester, (meth) acrylic acid butyl ester, Pentyl (meth) acrylate, hexyl (meth) acrylate Steryl, heptyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl ester (meth) acrylate, (meta) And the like.) Decenyl acrylate, dodecyl (meth) acrylate, and the like.
  • the binder polymer as the component (A) in the present invention preferably contains a carboxyl group from the viewpoint that it can be developed with an alkaline aqueous solution, that is, it can be developed with an alkaline solution.
  • a polymerizable monomer having a carboxyl group And other polymerizable monomers by radical polymerization for example, a polymerizable monomer having a carboxyl group And other polymerizable monomers by radical polymerization.
  • the binder polymer of the component (A) preferably contains styrene and Z or a styrene derivative as a polymerizable monomer.
  • styrene and a styrene or styrene derivative are contained as a copolymer component, it is preferable to contain 0.1 to 30% by weight, and 1 to 28% by weight, in order to improve both adhesion and peeling properties. %, More preferably 1.5 to 27% by weight. If this content is less than 0.1% by weight, the adhesion tends to be poor, and if it exceeds 30% by weight, the peeled pieces tend to be large and the peeling time tends to be long.
  • the binder polymer of the component (A) is alkali-developable, and from that viewpoint, the acid value is preferably 30 to 50 OmgKOH / g, and 100 to 50 OmgKOH / g. g, more preferably 100 to 400 mgKOH / g, and most preferably 100 to 200 mgKOH / g.
  • the acid value is less than 30 mgKOH / g, the development time tends to be long, and when it exceeds 50 OmgKOH / g, the developer resistance of the photocured resist tends to decrease.
  • the weight average molecular weight of the binder polymer (A) is 20.000 to 300.000. , 0 0 0 It is preferably 30, 00 00-: L 50, 00 0, and more preferably 40, 00 0-: L 0 0, 00 0. New When the weight average molecular weight is less than 200,000, the developer resistance tends to decrease, and when it exceeds 300,000, the development time tends to be long.
  • binder polymers When two or more of these binder polymers are used in combination, examples of the combination include two or more binder polymers composed of different copolymer components, two or more binder polymers having different weight average molecular weights, Examples include two or more types of binder polymers having different dispersities. Further, a polymer having a multimode molecular weight distribution described in Japanese Patent Application Laid-Open No. 11-327137, the disclosure of which is incorporated by reference, can also be used.
  • This component (B 1) is used in the photosensitive resin composition of the present invention having the first feature and the third feature. By including this component, the sensitivity, pattern shape, and the like of the resin composition can be improved.
  • the photopolymerizable compound having at least one polymerizable cyclic ether group in the molecule (B 1) is not particularly limited as long as it has at least one polymerizable cyclic ether group in the molecule.
  • Compounds having a cationically polymerizable cyclic ether group in the molecule can be used. Specific examples include an oxetane compound and an epoxy compound. By using these, the sensitivity, release characteristics, and pattern shape of the photosensitive resin composition are further improved. These are used alone or in combination of two or more.
  • the oxetane compound is not particularly limited as long as it has an oxetane ring in the molecule, a compound having one oxetane ring, a compound having two oxetane rings, a compound having three oxetane rings, Examples include compounds having four oxetane rings. These are used alone or in combination of two or more.
  • Examples of the compound having one oxetane ring include alkyloxane, such as oxetane, 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, and 3,3-dimethyloxetane; Methyl-3-methoxymethyloxetane, 3,3-di (trifluoromethyl) perfluoroxetane, 2-chloromethyloxetane, 3,3-bis (chloromethyl) oxetane, and the general formula (1) :
  • R ′ and R 2 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl having 6 to 18 carbon atoms.
  • the hydrogen atom of the oxetane ring may be substituted with a halogen atom such as fluorine. These are used alone or in combination of two or more.
  • R ′ is hydrogen It is preferably an atom, an alkyl group having 1 to 20 carbon atoms, an aryl group, a 6 to 18 carbon atom aryl group or a group containing a heterocyclic ring. More preferably, it is an alkyl group having 1 to 5 carbon atoms.
  • R 2 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkylcarbonyl group having 2 to 10 carbon atoms, and a carbon atom having 1 to 20 carbon atoms. Is preferably an alkoxycarbonyl group or an N-alkyl group having 2 to 10 carbon atoms, and more preferably a hydrogen atom.
  • halogen atom in the general formula (1) examples include fluorine, chlorine, bromine, iodine, and astatine.
  • Examples of the alkyl group having 1 to 20 carbon atoms in the general formula (1) include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
  • pentyl group isopentyl group, neopentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, pendecyl group, dodecyl group, tridecyl group, tetradecyl group, pendecyl group, hexadecyl group, heptyl group
  • Examples thereof include a decyl group, an octadecyl group, a nonadecyl group, an icosyl group, and structural isomers thereof.
  • Examples of the cycloalkyl group having 3 to 10 carbon atoms in the general formula (1) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.
  • Examples of the aryl group having 6 to 18 carbon atoms in the general formula (1) include a phenyl group, a tolyl group, a xylyl group, a biphenyl group, a naphthyl group, an anthryl group and a phenanthryl group. May be substituted with a halogen atom, an amino group, a nitro group, a cyano group, a mercapto group, an aryl group, an alkyl group having 1 to 20 carbon atoms, or the like.
  • Examples of the alkylamino group having 1 to 10 carbon atoms in the general formula (1) include a methylamino group, an ethylamino group, a propylamino group, and an isopropylamino group.
  • dialkylamino group having 2 to 20 carbon atoms in the general formula (1) examples include, for example, dimethylamino, getylamino, dipropylamino, And a diisopropylamino group.
  • alkyl mercapto group having 1 to 10 carbon atoms in the general formula (1) examples include a methyl mercapto group, an ethyl mercapto group, and a propyl mercapto group.
  • Examples of the hydroxyalkyl group having 1 to 20 carbon atoms in the general formula (1) include a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxyisopropyl group, and a hydroxybutyl group.
  • Examples of the carboxyalkyl group having 1 to 10 carbon atoms in the alkyl group in the general formula (1) include a carboxymethyl group, a carboxyethyl group, a carboxypropyl group, and a carboxybutyl group.
  • Examples of the acryl group having 1 to 10 carbon atoms in the alkyl group in the general formula (1) include a formyl group, an acetyl group, a propionyl group, a butyryl group, an isoptyryl group, a valeryl group, an isovaleryl group, and a vivaloyl group. Are listed.
  • Examples of the alkoxy group having 1 to 20 carbon atoms in the general formula (1) include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group.
  • Examples of the alkoxycarbonyl group having 1 to 20 carbon atoms in the general formula (1) include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, and a butoxycarbonyl group.
  • alkylcarbonyl group having 2 to 10 carbon atoms in the general formula (1) examples include an ethylcarbonyl group, a propylcarbonyl group, a butylcarbonyl group and the like.
  • the alkenyl group having 2 to 10 carbon atoms in the general formula (1) includes, for example, 1-propenyl group, 2-propenyl group, 2-methyl-1-propenyl group, 2-methyl_2 —Propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group and the like.
  • examples of the N-alkyl group having 2 to 10 carbon atoms include an ethylcarbamoyl group, a propyl group, and a propyl group. And a butylcarbamoyl group and a pentylcarbamoyl group.
  • examples of the group containing a heterocyclic ring in the general formula (1) that is, a group derived from a heterocyclic compound include a furyl group, a phenyl group, a pyrrolyl group, a thiazolyl group, an indolyl group, and a quinolyl group.
  • R ] ethyl group
  • Examples of the compound having two oxetane rings include a compound represented by the following general formula (2):
  • R 3 represents a divalent organic group, and R 4 and R 5 each independently have the same meaning as R ′ in the general formula (1)
  • examples of the divalent organic group include a linear or branched alkylene group having 120 carbon atoms, and a linear or branched poly (alkylene group having 16 carbon atoms in the alkylene group).
  • examples of the linear or branched alkylene group having 120 carbon atoms include an ethylene group, a propylene group, and a butylene group.
  • examples of the linear or branched poly (alkylenoxy) group having 16 carbon atoms in the alkylene group include a poly (ethyleneoxy) group and a poly (propylenoxy) group.
  • examples of the linear or branched unsaturated hydrocarbon group include an ethenylene group, a propenylene group, a methyl probenylene group, a butenylene group and the like.
  • examples of the divalent organic group in the general formula (2) include groups represented by the following general formulas or formulas (4) and (16). (Four)
  • R s has the same meaning as R ′ in the general formula (1)
  • n is a natural number from 1 to 10 and may be a mixture of compounds having different values of m
  • R9 is an oxygen atom, a sulfur atom, an alkylene having 1 to 6 carbon atoms, or
  • R ′ e has the same meaning as R ′ in the general formula (1)
  • R ′ 2 has the same meaning as R ′ in general formula (1), and 2 to 4 naphthalene rings may be substituted.
  • R 13 has the same meaning as R ′ in formula (1), and may have 2 to 4 substituents on the naphthalene ring
  • n is a natural number from 1 to 10 and may be a mixture of compounds having different values of n
  • Preferred compounds among the compounds having two oxetane rings include, for example, compounds represented by the following formulas (17) to (21).
  • the compound having three or four oxetane rings includes, for example, a compound represented by the general formula (22):
  • R ′ has the same meaning as R ′ in the general formula (1), and R 15 represents a branched alkylene group having 1 to 12 carbon atoms or a branched poly (alkyleneoxy) group.
  • J is 3 or 4
  • R 1 is as defined as R 1 in the general formula (1)
  • R 3 is as defined the R 3 in the formula (2)
  • R 15 is the one general formula Is the same as R 15 in (22)
  • j is the same as j in the general formula (22).
  • R 1 is as defined as R 1 in the general formula (1)
  • R 3 is as defined the R 3 in the formula (2)
  • R 15 is the one general formula Is the same as R 15 in (22)
  • R '"' is an alkyl group having 16 carbon atoms
  • Examples of the branched poly (alkyleneoxy) group in the above general formula (22) include the general formula (26):
  • Preferred compounds among the compounds having 3 or 4 oxetane rings include, for example, the following formula (27):
  • aromatic ring in the above oxetane compound may have a substituent, and examples of such a substituent include those exemplified for R 1 in the general formula (1).
  • substituents include those exemplified for R 1 in the general formula (1).
  • each of the plurality of substituents may be the same or different.
  • oxetane compound for example, a compound having 1 to 4 oxenine rings having a high molecular weight of about 1,000 to 5,000 can be used.
  • a polymer containing oxetane a polymer having an oxetane ring in a side chain described in K. Sato, A. Kameyama and T. Nishikubo, Macromolecules, 25, 1198 (1992), the disclosure of which is incorporated by reference. Can be used as well.
  • the epoxy compound preferably used as the component (B1) is not particularly limited as long as it has an epoxy group in the molecule, and examples thereof include compounds represented by the following formula. These are used alone or in combination of two or more.
  • epoxy compounds include the following formula:
  • This component (II) is used in the photosensitive resin composition of the present invention having the second and third characteristics, and is also preferably used in the photosensitive resin composition of the present invention having the first characteristic. Can be. By including this component, the sensitivity of the photosensitive resin composition according to the present invention can be further increased.
  • a radical polymerizable compound is preferably used as the photopolymerizable compound having at least one polymerizable ethylenically unsaturated group in the molecule of the component (B 2).
  • G a compound obtained by reacting a / 3-unsaturated carboxylic acid, 2,2-bis (4-((methyl) acryloxypolyethoxy) phenyl) propane, 2,2-bis (4-1 (( Bisphenol A (meta) acrylate compounds such as (meth) acryloxypolypropoxy) phenyl) propane, 2,2-bis (4-((meth) acryloxypolyethoxypolypropoxy) phenyl) propane, glycidyl Compounds obtained by reacting ⁇ , / 3-unsaturated carboxylic acids with group-containing compounds, urethane monomers such as (meth) acrylate compounds having urethane bonds , Nonylphenyldioxylene (meth) acrylate, archloro-1 / 3-hydroxypropyl-1- ⁇ '— (meth) acryloyloxetyl- ⁇ -phthalate,) 3-hydroxyethyl-1) 3' — (meta) ) Acryloyloxyshe
  • a bisphenol-based (meth) acrylate compound or a (meth) acrylate compound having a urethane bond may be contained as an essential component. preferable. These are used alone or in combination of two or more.
  • Examples of the compound obtained by reacting the above polyhydric alcohol with ⁇ -unsaturated carboxylic acid include polyethylene glycol di (meth) acrylate having 2 to 14 ethylene groups and the number of propylene groups. Is 2 to 14, polypropylene glycol di (meth) acrylate, trimethylolpropanedi (meth) acrylate, trimethylolpropanetri (meth) acrylate, trimethylolpropaneethoxylate (meth) acrylate, Trimethylolpropane triethoxytri (meth) acrylate, trimethylolpropanetriethoxytri (meth) Acrylate, trimethylolpropane tetraethoxytri (meth) acrylate, trimethylolpropanepentaethoxytri (meth) acrylate, tetramethylolmethanetri (meth) acrylate, tetramethylolmethanetetra (meth) acrylate, dipenty
  • Examples of the ⁇ , 3-unsaturated carboxylic acid include (meth) acrylic acid.
  • Examples of the 2,2-bis (4-((meth) acryloxypolyethoxy) phenyl) propane include, for example, 2,2-bis (4-((meth) acryloxydiethoxy) phenyl) propane , 2,2-bis (4-((meth) acryloxytriethoxy) phenyl) propane, 2,2-bis (4-((meth) acryloxytetraethoxy) phenyl) propane, 2,2- Bis (4-((meth) acryloxypheneethoxy) phenyl) propane, 2,2-bis (4-((meth) acryloxyhexaethoxy) phenyl) propane, 2,2-bis (4-(((meth) acryloxyheptae) Toloxy) phenyl) propane, 2,2-bis (4-((meth) acryloxyctaethoxy) phenyl) propane, 2,2-bis (4-(((meth) acryloxynonaethoxy)) Nyl) propane, 2,2-bis (4-((
  • Examples of the 2,2-bis (4-((meth) acryloxypolyethoxypolypropoxy) phenyl) propane include, for example, 2,2-bis (4-1 ((meth) acryloxydiethoxyoctapropoxy). ) Phenyl) pu bread, 2,2-bis (4-((meth) acryloxytetraethoxyte trapropoxy) phenyl) propane, 2,2-bis (4-((meta) Acryloxyhexaethoxyhexapropoxy) phenyl) propane and the like. These are used alone or in combination of two or more.
  • glycidyl group-containing compound for example, trimethylolpropane triglycidyl ether tertri (meth) acrylate, 2,2-bis (4- (meth) acryloxy-2-hydroxypropyloxy) phenyl and the like can be mentioned.
  • trimethylolpropane triglycidyl ether tertri (meth) acrylate, 2,2-bis (4- (meth) acryloxy-2-hydroxypropyloxy) phenyl and the like can be mentioned.
  • urethane monomer examples include, for example, an acrylic monomer having an OH group at the i3 position (mean), isophorone diisocyanate, 2,6-toluenediisocyanate, 2,4-toluenediisocyanate, 1,6 Addition reaction product with diisocyanate compounds such as hexamethylene diisocyanate, tris ((meth) acryloxytetraethylene glycol isocyanate) hexamethylene isocyanurate, E ⁇ modified urethane resin (Meth) acrylate, P ⁇ modified urethane (meth) acrylate, E ⁇ , P ⁇ modified urethane (meth) acrylate, and the like.
  • E O denotes ethylene oxide
  • the compound modified with E O has a block structure of an ethylene oxide group.
  • P O represents propylene oxide
  • the compound modified with P O has a block structure of a propylene oxide group.
  • E O-modified urethane (meth) acrylate P ⁇ -modified urethane (meth) acrylate and E O, PO-modified urethane (meth) acrylate, for example, the general formula (28):
  • R ′ 7 and R IS each independently represent a hydrogen atom or a methyl group
  • X 1 and X 2 each independently represent an ethylene oxide group or a propylene oxide group
  • Z has 2 to 2 carbon atoms.
  • two or more X ′ and two or more X 2 may be the same or different, and X 1 and X 2 are two alkylene oxide groups (ethylene Oxoxide group and propylene oxide group), two kinds of X 1 and two kinds of X 2 may exist at random or may exist in blocks.
  • Examples of the EO-modified urethane (meth) acrylate represented by the general formula (28) include Shin Nakamura Chemical Co., Ltd. product name U A-11.
  • E ⁇ , P ⁇ modified urethane (meth) acrylate examples include Shin Nakamura Chemical Co., Ltd. product name U A-13.
  • alkyl (meth) acrylate examples include methyl (meth) acrylate, methyl (meth) acrylate, butyl (meth) acrylate, and 2-methylhexyl (meth) acrylate. No.
  • This component (C 1) is used in the photosensitive resin composition of the present invention having the first feature and the second feature. By including this component, the sensitivity and resolution of the photosensitive resin composition according to the present invention can be further increased.
  • the photoacid generator of the component (C1) is not particularly limited as long as it is a compound that generates an acid (electron pair acceptor) by light.
  • a cation that generates a carbocation by light or heat What is used as a polymerization initiator can be used.
  • a rhododium salt compound, a sulfonium salt compound, an ammonium salt compound, a phosphonium salt compound, an arsonium salt compound, a stibonium salt compound, an oxonium chloride compound, a selenodium salt compound, a stannonium salt compound And the like and preferably a rhododium salt compound, a sulfonium salt compound or an ammonium chloride compound.
  • a rhododium salt compound, a sulfonium salt compound, an ammonium chloride compound are used alone or in combination of two or more.
  • sodium salts examples include, but are not limited to, diphenyl pentafluorobenzene, difluorohexafluorophosphinate, diphenyl pentafluorohexaphosphate, and 4′-butyl phenylphenyl.
  • sulfonium salt examples include triphenylsulfonium tetrafluoroporate, triphenylsulfoniumhexafluorophosphinate, triphenylsulfoniumhexafluoroantimonate, and triphenylsulfoniumhexafluorate. Loarsenate, triphenylsulfonium triflate and the like. These are used alone or in combination of two or more.
  • This component (C 2) is used in the photosensitive resin composition of the present invention having the third feature. It is also preferably used for the photosensitive resin composition of the present invention having the first feature and the second feature. That is, the photosensitive resin composition of the present invention having the first feature and the second feature includes a photoacid generator as an essential component as the component (C 1), and a radical polymerization initiator as the component (C 2). It is preferable to use an initiator that generates cations and radicals by light or heat. By including this component, the sensitivity of the photosensitive resin composition according to the present invention can be further increased.
  • Examples of the (C 2) radical polymerization initiator include benzophenone,
  • 2,4,5—triarylimidazole dimers include, for example, 2,2′-bis (2-chlorophenyl) -1,4,4 ′, 5,5′—tetraphenylbisimidazole, 2,2'-bis (2,4-dichloromouth phenyl) 1-4,4 ', 5,5'-tetraphenylbisimidazole, 2,2'-bis (2,3-dichloromouth phenyl) 1-4, 4 ', 5, 5'-tetraphenylbisimidazole, 2, 2'-bis (2-cyclophenyl) -1,4 ', 5,5'-tetrakis (m-methoxy) phenylbisimidazole, 2,2' —Bis (2,3-dichloromouth phenol) 1-4,4 ′, 5,5 ′ —Tetrakis (m-methoxy) phenirubiimidazole, 2,2′-Bis (2,4-dichlor
  • the (C 2) radical polymerization initiator includes, as sensitizers, for example, 7-amino-14-methylcoumarin, 7-dimethylamino-14-methylcoumarin, 7-ethylamino-4-methylcoumarin, and 7-methylamido.
  • a thioxanthone derivative such as methyl thioxanthone and isopropyl thioxanthone, anthracene, pyrene and phenothiazine can be used in combination as a sensitizer. These are used alone or in combination of two or more.
  • the amount of the component (A) is 100 parts by weight of the total of the components (A) and (B) ((B1) component + (B2) component), When used as a photosensitive element, it is at least 40 parts by weight from the viewpoint of coating properties, preferably at most 80 parts by weight, more preferably at least 45 to 60 parts by weight from the viewpoint of sensitivity.
  • the amount of the component (B) (the component (B1) + the component (B2)) is, for the same reason as described above, based on 100 parts by weight of the total amount of the components (A) and (B). It is preferably 20 to 60 parts by weight, more preferably 40 to 55 parts by weight.
  • the component (B1) is at least 5% by weight from the viewpoint of the peeling time, preferably 95% by weight or less, and more preferably 5 to 80% by weight from the viewpoint of sensitivity. More preferably, it is particularly preferably from 10 to 50% by weight.
  • the component (B 2) is present in the component (B) in an amount of 5% by weight or more from the viewpoint of sensitivity. Yes, it is preferably 95% by weight or less, more preferably 20 to 95% by weight, and particularly preferably 50 to 90% by weight from the viewpoint of the peeling time.
  • the amount of component (C) (component (C 1) + component (C 2)) should be at least 1 part by weight from the viewpoint of sensitivity, based on 100 parts by weight of the total of components (A) and (B). From the viewpoint of resolution, the amount is preferably 10 parts by weight or less, more preferably 2 to 6 parts by weight.
  • the component (C 1) in the component (C) is preferably at least 10% by weight from the viewpoint of resolution and release characteristics, and is preferably at most 80% by weight from the viewpoint of sensitivity, and is preferably from 10 to 50% by weight. Is more preferable, and particularly preferably 10 to 40% by weight.
  • the component (C 2) in the component (C) is preferably at least 20% by weight from the viewpoint of fine wire adhesion, and preferably at most 90% by weight from the viewpoint of resolution and sensitivity, and 50 to 90% by weight. %, More preferably 60 to 90% by weight.
  • the photosensitive resin composition containing the above components may contain a dye such as malachite green, a photochromic agent such as tribromophenylsulfone or leucocrystalline violet, a thermochromic inhibitor, Plasticizers such as toluenesulfone amide, pigments, fillers, defoamers, flame retardants, stabilizers, adhesion promoters, leveling agents, release accelerators, antioxidants, fragrances, imaging agents, thermal crosslinking An agent or the like can be contained in an amount of about 0.01 to 20 parts by weight each based on 100 parts by weight of the total of the components (A) and (B). These are used alone or in combination of two or more.
  • the photosensitive resin composition according to the present invention may contain, as necessary, methanol, ethanol, acetone, methyl ethyl ketone, methyl sorb, ethyl sorb, toluene, N, N-dimethylformamide, propylene. It can be dissolved in a solvent such as glycol monomethyl ether or a mixed solvent thereof and applied as a solution having a solid content of about 30 to 60% by weight. Its use is not particularly limited, but copper, copper-based alloy, iron, iron-based alloy, etc. It is preferable to apply it as a liquid resist on the metal surface and dry it, and then use a protective film if necessary, or use it in the form of a photosensitive element.
  • the thickness of the photosensitive resin composition layer to be applied varies depending on the application, but is preferably about 1 to 100 m in thickness after drying.
  • the protective film may be a polymer film such as polyethylene or polypropylene.
  • a photosensitive element according to the present invention that is, a resist layer comprising a photosensitive resin composition having any one of the first, second, and third features of the present invention described above is formed on a support.
  • the resulting photosensitive element will be described with reference to the drawings.
  • FIG. 1 schematically shows an embodiment of the photosensitive element.
  • the photosensitive element 1 includes a support 11 and a resist layer (photosensitive resin composition layer) formed thereon. 1) and 2 are included.
  • the support 11 for example, a polymer film of polyethylene terephthalate, polypropylene, polyethylene, polyester, or the like can be preferably used.
  • the method for forming the resist layer 12 on the support 11 is not particularly limited, but it can be preferably obtained by applying and drying a photosensitive resin composition.
  • the application can be performed by a known method such as, for example, one night in the mouth, one night in the comma, one night in the graviaco, one night in the air, one night in the die, one night in the barco, and the like.
  • Drying can be performed at about 70 to 150 ° (: about 5 to 30 minutes.
  • the amount of the remaining organic solvent in the resist layer 12 is determined by the amount of the organic solvent diffusion in a later step. From the viewpoint of prevention, the content is preferably 2% by weight or less.
  • the thickness of the polymer film of the support 11 is preferably 1 to 100 m.
  • One of these polymer films may serve as a support for the resist layer, and the other may serve as a protective film for the resist layer, and may be laminated on both sides of the resist layer.
  • a protective film a resist layer and a support It is preferable to select a film having a smaller adhesive force between the resist layer and the protective film than the adhesive force of the film, and a film having a low fish eye is preferable.
  • the photosensitive element has an intermediate layer and a protective layer such as a cushion layer, an adhesive layer, a light absorbing layer, and a gas barrier layer in addition to the resist layer, the support, and the protective film. May be.
  • a protective layer such as a cushion layer, an adhesive layer, a light absorbing layer, and a gas barrier layer in addition to the resist layer, the support, and the protective film. May be.
  • the photosensitive element is stored, for example, as it is or by further laminating a protective film on the surface of the resist layer and winding it around a cylindrical core.
  • the support is wound so that the support is on the outside.
  • On the end surface of the roll-shaped photosensitive element roll it is preferable to install an end separation from the viewpoint of protection of the end surface, and it is preferable to install a moisture-proof end surface separation from the viewpoint of edge-proof fusion.
  • As a packing method it is preferable to wrap in a black sheet having small moisture permeability.
  • Examples of the core include plastics such as polyethylene resin, polypropylene resin, polystyrene resin, polyvinyl chloride resin, and ABS resin (acrylonitrile-butadiene-styrene copolymer).
  • plastics such as polyethylene resin, polypropylene resin, polystyrene resin, polyvinyl chloride resin, and ABS resin (acrylonitrile-butadiene-styrene copolymer).
  • step (i) the above-described photosensitive element 1 is placed on the circuit forming substrate 2 and the resist layer 12 is brought into close contact with the surface of the circuit forming substrate 2.
  • the protective film Prior to lamination, if a protective film is present on the resist layer 12 of the photosensitive element 1, the protective film is removed.
  • the circuit forming substrate 2 is coated with about 0.1 to 1 MPa (1 to: L 0 kgf / cm 2). ( Approximately 2 ).
  • the substrate 2 for circuit formation A layer provided with a metal layer (not shown), which is a metal layer, is used.
  • the surface of the substrate 2 on which the photosensitive element 1 is laminated is usually a metal surface, but there is no particular limitation.
  • actinic rays are radiated imagewise onto the resist layer 12 through the mask pattern 3, and the resist in the exposed area is exposed.
  • Layer 12 is light cured.
  • the mask pattern 3 may be a negative type or a positive type, and a commonly used mask pattern can be used.
  • the light source of the actinic ray a known light source, for example, a carbon arc lamp, a mercury vapor arc lamp, a high-pressure mercury lamp, a xenon lamp, or the like that effectively emits ultraviolet light or visible light is used. Further, direct laser exposure can be performed without using a mask pattern.
  • the resist layer in the unexposed portion is selectively removed by development to form a resist pattern 121 as shown in FIG. 2 (C).
  • the exposure in the step (ii) can be performed in the presence of the support 11 as long as light irradiation on the resist layer 12 is not hindered.
  • the support 1 Remove one.
  • the development is performed by removing unexposed portions by jet development using a developer such as an alkaline aqueous solution, an aqueous developer, or an organic solvent, or dry development.
  • the above-mentioned alkaline aqueous solution can be preferably used, for example, a dilute solution of 0.1 to 5% by weight of sodium carbonate, a dilute solution of 0.1 to 5% by weight of potassium carbonate, and a dilute solution of 0.1 to 5% by weight of sodium hydroxide. Dilute solutions are examples.
  • the pH of this alkaline aqueous solution is preferably in the range of 9 to 11, and the temperature is adjusted according to the developability of the photosensitive resin composition layer.
  • a surfactant, an antifoaming agent, an organic solvent and the like may be mixed in the alkaline aqueous solution.
  • Examples of the development method include a dive method, a spray method, brushing, and slapping.
  • the laser formed by heating at about 60 to 250 ° C. or exposure at about 0.2 to 10 J / cm 2 as necessary.
  • the distaste pattern may be further cured.
  • FIGS. 3 and 4 schematically show the steps as an embodiment.
  • the steps up to the formation of the resist pattern include a step (i) of laminating the photosensitive element 1 on the circuit forming substrate 2, an exposure step (ii), and a development step (ih). This is the same as described in.
  • a circuit forming substrate 2 having a thin work layer 21 made of copper or the like on its surface is used.
  • FIG. 3 shows a circuit forming process by a subtractive method using etching
  • FIG. 4 shows a circuit forming process by a semi-additive method using plating.
  • the process target layer of the circuit forming substrate 2 is formed by using the formed resist pattern 121 as a mask, as shown in FIG. 3B.
  • a cupric chloride solution, a ferric chloride solution, an alkali etching solution, or the like can be used for etching the work layer 21 made of a metal surface.
  • plating methods include copper plating, solder plating, nickel plating, and gold plating.
  • the resist pattern 121 remaining on the substrate 2 is peeled off with, for example, a more alkaline aqueous solution than the alkaline aqueous solution used for development.
  • the printed wiring board 4 on which the circuit 211 is formed is obtained.
  • the processed layer 21 is also removed by, for example, a quick etching method.
  • the strong alkaline aqueous solution include 1 to 10% by weight water
  • An aqueous solution of sodium oxide, an aqueous solution of 1 to 10% by weight of potassium hydroxide, and the like are used.
  • Examples of the peeling method include an immersion method and a spray method. Further, the printed wiring board on which the resist pattern is formed may be a multilayer printed wiring board or may have a small diameter through hole. Next, the present invention will be described in more detail with reference to examples. Examples 1-20 and Comparative Examples 1-3
  • the photosensitive element was obtained by uniformly coating the film on a polyethylene terephthalate film and drying it in a hot air convection dryer at 100 ° C. for 10 minutes.
  • the thickness of the photosensitive resin composition layer (resist layer) was 2.
  • the copper surface of a copper-clad laminate (manufactured by Hitachi Chemical Co., Ltd., trade name: MCL-E_61), which is a glass epoxy material with copper foil (thickness 35 ⁇ m) laminated on both sides, is equivalent to Polished using a polishing machine with a brush (made by Sankei Co., Ltd.), washed with water, dried in an air stream, and heated the obtained copper-clad laminate to 80 ° C.
  • the photosensitive resin composition layer was laminated while being heated to 110 ° C.
  • the polyethylene terephthalate film was peeled off, and unexposed portions were removed by spraying a 1% by weight aqueous solution of sodium carbonate at 30 ° C. for 20 seconds.
  • the photosensitivity of the photosensitive resin composition was evaluated by measuring the number of step tablets of the obtained resist pattern (that is, the photocured film formed on the copper-clad laminate).
  • the light sensitivity is indicated by the number of steps on the step evening bullet, and the higher the number of steps on the step evening bullet, the higher the light sensitivity.
  • the pattern after development was observed, and the resolution (; m) was determined from the line width (m) remaining as line-and-space. Further, the film was cured at an exposure dose 6 0 mJ / cm z is impregnated with 3% N A_ ⁇ _H solution was measured the time required for peeling.
  • Tables 6 to 9 show the above evaluation results.
  • Example 6 7 8 9 10 11 12 Sensitivity (ST / 41) 27 26 26 26 26 25 25 Resolution (m) 25 20 20 20 18 20 22 Peeling time (sec) 37 18 32 26 36 40 47 Table 8
  • the components shown in Table 10 were blended to obtain a solution of the photosensitive resin composition.
  • the components shown in Table 11 were dissolved in the obtained solution of the photosensitive resin composition to obtain a solution of the photosensitive resin composition.
  • a photosensitive element was obtained in the same manner as in the above example using this photosensitive resin composition solution.
  • the thickness of the obtained photosensitive resin composition layer (resist layer) was 30 / xm.
  • the pattern after development was observed, and the resolution (im) was determined from the line width (/ m) remaining as line 'and' space. Furthermore, the pattern of a 30-zm-wide line was observed using SEM, and the pattern shape was evaluated.
  • the resist pattern is preferably rectangular.
  • the peel time was measured as follows. The sample irradiated with an exposure amount (21 steps / 41) corresponding to each sensitivity was developed with a 1% by weight aqueous solution of sodium carbonate. After standing for 1 day and night, the 3 wt% sodium hydroxide solution was kept at 45 ° C and stirred with a stirrer to measure the time (sec) of immersion and the start of peeling. Note that the stripping time is preferably shorter.
  • Table 12 shows the evaluation results of Examples 21 to 24 and Comparative Example 4. Table 12

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  • General Physics & Mathematics (AREA)
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Abstract

Cette invention a trait à une composition à base de résine photosensible comprenant, (A), un polymère liant, (B1), un composé photopolymérisable possédant au moins un groupe éther cyclique polymérisable par molécule et, (C1), un générateur de photoacide. Elle concerne également une composition à base de résine photosensible comprenant, (A), un polymère liant, (B2), un composé photopolymérisable possédant au moins un groupe insaturé éthyléniquement polymérisable par molécule et, (C1), un générateur de photoacide. Elle porte, de surcroît, sur une composition à base de résine photosensible comprenant, (A), un polymère liant, (B1), un composé photopolymérisable possédant au moins un groupe éther cyclique polymérisable par molécule, (B2), un composé photopolymérisable possédant au moins un groupe insaturé éthyléniquement polymérisable par molécule et, (C2), un initiateur de polymérisation radicalaire.
PCT/JP2000/006353 1999-09-17 2000-09-18 Compositions a base de resine photosensibles, element photosensible contenant ces compositions, procede de production d'un motif de reserve et procede de production de carte a circuit imprime Ceased WO2001022165A1 (fr)

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JP2001525474A JP3765272B2 (ja) 1999-09-17 2000-09-18 感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの製造法及びプリント配線板の製造法
AU73150/00A AU7315000A (en) 1999-09-17 2000-09-18 Photosensitive resin compositions, photosensitive element containing the same, process for producing resist pattern, and process for producing printed circuit board

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JP26386399 1999-09-17
JP11/263863 1999-09-17
JP11/313180 1999-11-04
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JP2006153984A (ja) * 2004-11-25 2006-06-15 Tokyo Ohka Kogyo Co Ltd 感光性樹脂組成物、およびこれを用いた感光性ドライフィルム
JP2007071995A (ja) * 2005-09-05 2007-03-22 Tokyo Ohka Kogyo Co Ltd 感光性樹脂組成物
WO2007145309A1 (fr) * 2006-06-16 2007-12-21 Cmet Inc. Composition de résine pour stéréolithographie
JP2008045035A (ja) * 2006-08-16 2008-02-28 Az Electronic Materials Kk 印刷用硬化性樹脂組成物およびそれを用いたパターン形成方法
JP2009134255A (ja) * 2007-10-31 2009-06-18 Sekisui Chem Co Ltd マイクロパターン形成用材料、マイクロパターン複合材及びその製造方法並びに微小３次元構造基板の製造方法
JP2009221370A (ja) * 2008-03-17 2009-10-01 Sekisui Chem Co Ltd マイクロパターン複合材、微小３次元構造体の製造方法及びマイクロパターン形成用硬化性組成物
JP5007668B2 (ja) * 2005-04-12 2012-08-22 コニカミノルタエムジー株式会社 活性光線硬化型組成物、活性光線硬化型インクジェットインク、画像形成方法及びインクジェット記録装置
JP5383196B2 (ja) * 2006-09-19 2014-01-08 新日鉄住金化学株式会社 熱重合性樹脂組成物
WO2017170879A1 (fr) * 2016-03-31 2017-10-05 株式会社Adeka Composition durcissable, procédé de fabrication d'un produit durci, et produit durci obtenu
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WO2017170882A1 (fr) * 2016-03-30 2017-10-05 株式会社Adeka Composition durcissable, procédé de production de produit durci et produit durci associé
JPWO2017170880A1 (ja) * 2016-03-30 2019-02-14 株式会社Adeka 硬化性組成物、硬化物の製造方法、およびその硬化物
JP2019521118A (ja) * 2016-07-13 2019-07-25 常州強力先端電子材料有限公司Ｃｈａｎｇｚｈｏｕ Ｔｒｏｎｌｙ Ａｄｖａｎｃｅｄ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ Ｃｏ．，Ｌｔｄ． 多官能オキセタン系化合物およびその製造方法
WO2020243898A1 (fr) * 2019-06-04 2020-12-10 Showa Denko Materials Co. Ltd Procédé de formation de film durci
CN114509914A (zh) * 2020-11-16 2022-05-17 常州强力先端电子材料有限公司 光固化组合物、光学膜及其制备方法和光学产品

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JP2002341537A (ja) * 2001-05-21 2002-11-27 Jsr Corp めっき造形物製造用ネガ型感放射線性樹脂組成物およびめっき造形物の製造方法
JP2006153984A (ja) * 2004-11-25 2006-06-15 Tokyo Ohka Kogyo Co Ltd 感光性樹脂組成物、およびこれを用いた感光性ドライフィルム
US7662541B2 (en) 2004-11-25 2010-02-16 Tokyo Ohka Kogyo Co., Ltd. Photosensitive resin composition and photosensitive dry film by the use thereof
JP5007668B2 (ja) * 2005-04-12 2012-08-22 コニカミノルタエムジー株式会社 活性光線硬化型組成物、活性光線硬化型インクジェットインク、画像形成方法及びインクジェット記録装置
JP2007071995A (ja) * 2005-09-05 2007-03-22 Tokyo Ohka Kogyo Co Ltd 感光性樹脂組成物
EP2033982A4 (fr) * 2006-06-16 2012-02-29 Cmet Inc Composition de résine pour stéréolithographie
WO2007145309A1 (fr) * 2006-06-16 2007-12-21 Cmet Inc. Composition de résine pour stéréolithographie
JP2007332294A (ja) * 2006-06-16 2007-12-27 Cmet Inc 光学的立体造形用樹脂組成物
US8293448B2 (en) 2006-06-16 2012-10-23 Cmet Inc. Resin composition for stereolithography
CN101466767B (zh) * 2006-06-16 2011-12-07 Cmet公司 立体光刻造型用树脂组合物
JP2008045035A (ja) * 2006-08-16 2008-02-28 Az Electronic Materials Kk 印刷用硬化性樹脂組成物およびそれを用いたパターン形成方法
JP5383196B2 (ja) * 2006-09-19 2014-01-08 新日鉄住金化学株式会社 熱重合性樹脂組成物
JP2009134255A (ja) * 2007-10-31 2009-06-18 Sekisui Chem Co Ltd マイクロパターン形成用材料、マイクロパターン複合材及びその製造方法並びに微小３次元構造基板の製造方法
JP2009221370A (ja) * 2008-03-17 2009-10-01 Sekisui Chem Co Ltd マイクロパターン複合材、微小３次元構造体の製造方法及びマイクロパターン形成用硬化性組成物
KR102272147B1 (ko) 2016-03-30 2021-07-01 가부시키가이샤 아데카 경화성 조성물, 경화물의 제조 방법, 및 그 경화물
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WO2017170881A1 (fr) * 2016-03-30 2017-10-05 株式会社Adeka Composition durcissable, procédé de production de produit durci et produit durci ainsi obtenu
WO2017170882A1 (fr) * 2016-03-30 2017-10-05 株式会社Adeka Composition durcissable, procédé de production de produit durci et produit durci associé
KR20180128926A (ko) * 2016-03-30 2018-12-04 가부시키가이샤 아데카 경화성 조성물, 경화물의 제조 방법, 및 그 경화물
JPWO2017170881A1 (ja) * 2016-03-30 2019-02-07 株式会社Adeka 硬化性組成物、硬化物の製造方法、およびその硬化物
JPWO2017170880A1 (ja) * 2016-03-30 2019-02-14 株式会社Adeka 硬化性組成物、硬化物の製造方法、およびその硬化物
WO2017170879A1 (fr) * 2016-03-31 2017-10-05 株式会社Adeka Composition durcissable, procédé de fabrication d'un produit durci, et produit durci obtenu
JPWO2017170879A1 (ja) * 2016-03-31 2019-02-14 株式会社Adeka 硬化性組成物、硬化物の製造方法、およびその硬化物
JP2019521118A (ja) * 2016-07-13 2019-07-25 常州強力先端電子材料有限公司Ｃｈａｎｇｚｈｏｕ Ｔｒｏｎｌｙ Ａｄｖａｎｃｅｄ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ Ｃｏ．，Ｌｔｄ． 多官能オキセタン系化合物およびその製造方法
US10906882B2 (en) 2016-07-13 2021-02-02 Changzhou Tronly Advanced Electronic Materials Co., Ltd. Polyfunctional oxetane-based compound and production method thereof
US11555022B2 (en) 2016-07-13 2023-01-17 Changzhou Tronly New Electronic Materials Co., Ltd. Polyfunctional oxetane-based compound and production method thereof
WO2020243898A1 (fr) * 2019-06-04 2020-12-10 Showa Denko Materials Co. Ltd Procédé de formation de film durci
CN114509914A (zh) * 2020-11-16 2022-05-17 常州强力先端电子材料有限公司 光固化组合物、光学膜及其制备方法和光学产品
WO2022100753A1 (fr) * 2020-11-16 2022-05-19 常州强力先端电子材料有限公司 Composition photodurcissable, film optique et son procédé de préparation, et produit optique

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