WO2020240993A1 - Composition de résine et film de résine - Google Patents

Composition de résine et film de résine Download PDF

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Publication number
WO2020240993A1
WO2020240993A1 PCT/JP2020/011356 JP2020011356W WO2020240993A1 WO 2020240993 A1 WO2020240993 A1 WO 2020240993A1 JP 2020011356 W JP2020011356 W JP 2020011356W WO 2020240993 A1 WO2020240993 A1 WO 2020240993A1
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Prior art keywords
polymer
meth
resin composition
acrylate
mass
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PCT/JP2020/011356
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English (en)
Japanese (ja)
Inventor
健宏 木下
恭章 川口
将行 小林
俊亮 林
正偉 周
Original Assignee
昭和電工株式会社
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Application filed by 昭和電工株式会社 filed Critical 昭和電工株式会社
Priority to CN202080037012.5A priority Critical patent/CN113853394A/zh
Priority to CN202311653995.7A priority patent/CN117467065A/zh
Priority to KR1020217036896A priority patent/KR102645527B1/ko
Priority to JP2021522649A priority patent/JP7367761B2/ja
Publication of WO2020240993A1 publication Critical patent/WO2020240993A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/302—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and two or more oxygen atoms in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • 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
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides

Definitions

  • the present invention relates to resin compositions and resin films.
  • the present application claims priority based on Japanese Patent Application No. 2019-101097 filed in Japan on May 30, 2019, the contents of which are incorporated herein by reference.
  • a resin film has been used for the protective film, interlayer insulating film, and flattening film of electronic components such as TFT (thin-film-transistor) type liquid crystal display elements, magnetic head elements, integrated circuit elements, and solid-state image sensors.
  • TFT thin-film-transistor
  • a transparent conductive film such as indium tin oxide (ITO) is usually formed on an interlayer insulating film formed by using a photosensitive resin composition, and a liquid crystal alignment film is formed on the transparent conductive film. ing. Therefore, the interlayer insulating film of the liquid crystal display element is exposed to high temperature conditions in the step of forming the transparent electrode film on the interlayer insulating film. Therefore, as the material of the resin film used as the interlayer insulating film of the liquid crystal display element, a photosensitive resin composition capable of forming a resin film having good transparency and developability and excellent heat resistance is used.
  • Patent Document 1 describes a photosensitive resin composition containing a copolymer containing a repeating unit derived from a hydroxyphenyl (meth) acrylate and a repeating unit derived from a blocked isocyanate group-containing unsaturated compound.
  • a resin film obtained by coating on top and drying is disclosed.
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a resin composition capable of forming a resin film having excellent transparency, developability, and heat resistance. Another object of the present invention is to provide a resin film having excellent transparency, developability and heat resistance, which is made of a cured product of the resin composition of the present invention.
  • the present inventor has diligently studied to solve the above problems. As a result, by curing the resin composition containing the polymer (A) having at least a structural unit derived from hydroxyphenyl (meth) acrylate and a structural unit derived from phenylenedi (meth) acrylate, transparency, developability, We have found that a resin film having excellent heat resistance can be obtained, and have conceived the present invention. That is, the present invention relates to the following matters.
  • a resin composition comprising a polymer (A) having at least a structural unit derived from hydroxyphenyl (meth) acrylate and a structural unit derived from phenylenedi (meth) acrylate.
  • the total content of the structural unit derived from the hydroxyphenyl (meth) acrylate and the structural unit derived from the phenylenedi (meth) acrylate in the polymer (A) is 40 to 100 mol%.
  • the total content of the structural unit derived from the hydroxyphenyl (meth) acrylate and the structural unit derived from the phenylenedi (meth) acrylate in the polymer (A) is 50 to 90 mol%.
  • the resin composition according to [3], wherein the content of the structural unit derived from the monomer having a hydroxyalkyl group and an ethylenically unsaturated group is 1 to 20 mol%.
  • the resin composition of the present embodiment contains the polymer (A).
  • the resin composition of the present embodiment may contain a photosensitive component (B) and / or a thermosetting resin (C) together with the polymer (A).
  • the polymer (A) contained in the resin composition of the present embodiment has at least a structural unit derived from hydroxyphenyl (meth) acrylate and a structural unit derived from phenylenedi (meth) acrylate. If necessary, the polymer (A) may contain a monomer unit having a hydroxyalkyl group and an ethylenically unsaturated group, or a structural unit derived from other monomers.
  • "(meth) acrylate” means at least one selected from methacrylate and acrylate.
  • alkali solubility is imparted by the polymer (A) having a structural unit derived from hydroxyphenyl (meth) acrylate.
  • the structural unit derived from hydroxyphenyl (meth) acrylate include a structural unit derived from o-hydroxyphenyl (meth) acrylate, a structural unit derived from m-hydroxyphenyl (meth) acrylate, and p-hydroxyphenyl ( Examples thereof include structural units derived from meta) acrylate.
  • the polymer (A) may have only one type of structural units derived from these hydroxyphenyl (meth) acrylates having different bonding positions of substituents, or may have two or more types.
  • a structural unit derived from hydroxyphenyl (meth) acrylate from the viewpoint of developability when the resin composition of the present embodiment is used as the photosensitive resin composition and reactivity when synthesizing the polymer (A).
  • a structural unit derived from p-hydroxyphenyl (meth) acrylate is preferable.
  • the content of the structural unit derived from hydroxyphenyl (meth) acrylate in the polymer (A) is preferably 39.5 to 99.95 mol%, and preferably 44.5 to 94.9 mol%. More preferably, it is 49.6 to 89.8 mol%.
  • the content of the structural unit is 39.5 mol% or more, the resin composition has even more excellent alkali solubility and can form a resin film having a good pattern shape.
  • the content of the structural unit is 99.95 mol% or less, the content of the structural unit derived from phenylenedi (meth) acrylate can be sufficiently secured, so that even more excellent heat resistance can be obtained.
  • the polymer (A) since the polymer (A) has a structural unit derived from phenylenedi (meth) acrylate, the degree of polymerization of the polymer (A) is high, and the polymer has a high purity. It becomes a coalescence (A). Therefore, the resin film obtained by curing the resin composition of the present embodiment has good heat resistance.
  • the structural unit derived from phenylenedi (meth) acrylate include a structural unit derived from 1,2-phenylenedi (meth) acrylate, a structural unit derived from 1,3-phenylenedi (meth) acrylate, and 1 , 4-Constituent units derived from phenylenedi (meth) acrylate.
  • the polymer (A) may have only one type of structural unit derived from these phenylenedi (meth) acrylates having different bonding positions of substituents, or may have two or more types.
  • 1,4-phenylenedi (meth) acrylate is particularly preferable from the viewpoint of reactivity when synthesizing the polymer (A).
  • the content of the constituent unit derived from phenylenedi (meth) acrylate in the polymer (A) is preferably 0.05 to 0.5 mol%, and preferably 0.1 to 0.45 mol%. More preferably, it is 0.15 to 0.4 mol%. If necessary, it may be 0.15 to 0.25 mol%, 0.25 to 0.4 mol%, or the like.
  • the content of the structural unit is 0.05 mol% or more, the resin composition has even better heat resistance in the resin film obtained by curing the resin composition.
  • the content of the structural unit is 0.5 mol% or less, the content of the structural unit derived from hydroxyphenyl (meth) acrylate can be sufficiently secured, so that a resin composition capable of forming a resin film having a good pattern shape can be formed. It becomes a thing.
  • the structural unit derived from acrylate) is preferably 99.99: 0.01 to 99.00: 1.00, and more preferably 99.95: 0.05 to 99.50: 0.50. preferable.
  • the resin composition has even more excellent alkali solubility and can form a resin film having a good pattern shape. Become.
  • the molar ratio of the constituent unit derived from the phenylenedi (meth) acrylate is 0.01 or more, the effect of improving the heat resistance of the resin film made of the cured product of the resin composition becomes remarkable.
  • the total content of the structural unit derived from the hydroxyphenyl (meth) acrylate and the structural unit derived from the phenylenedi (meth) acrylate in the polymer (A) is preferably 40 to 100 mol%, preferably 50 to 50 to 100 mol%. It is more preferably 90 mol%, further preferably 60 to 85 mol%. If necessary, it may be 60 to 70 mol% or 70 to 85 mol%. When the total content of the constituent units is 40 mol% or more, the resin composition has even more excellent alkali solubility and can form a resin film having a good pattern shape.
  • a hydroxyalkyl group and an ethylenically unsaturated group can be obtained because a polymer having particularly high polymer purity can be obtained and a resin film having good properties such as transparency, heat resistance, and developability can be obtained. It is preferable to include a structural unit derived from a monomer having.
  • hydroxyalkyl group in the structural unit derived from the monomer having the hydroxyalkyl group and the ethylenically unsaturated group a hydroxyalkyl group having 1 to 8 carbon atoms is preferable, and a hydroxyalkyl group having 2 to 6 carbon atoms is more preferable. Specific examples thereof include a hydroxyethyl group, a hydroxypropyl group and a hydroxybutyl group.
  • Specific examples of the structural unit derived from the monomer having a hydroxyalkyl group and an ethylenically unsaturated group include hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 3-hydroxypropyl (meth) acrylate.
  • the polymer (A) may have only one type of structural unit derived from these monomers having a hydroxyalkyl group and an ethylenically unsaturated group, or may have two or more types.
  • 2-hydroxyethyl (meth) is particularly good in availability of the monomer and polymerizability when synthesizing the polymer (A).
  • Constituent units derived from acrylates and / or constituent units derived from 2,3-dihydroxypropyl (meth) acrylates are preferred.
  • the polymer (A) has a structural unit derived from a monomer having a hydroxyalkyl group and an ethylenically unsaturated group, the structural unit derived from the hydroxyphenyl (meth) acrylate and the pheni in the polymer (A).
  • the total content of the constituent units derived from the range (meth) acrylate is preferably 50 to 90 mol%, more preferably 60 to 85 mol%. If necessary, it may be 60 to 70 mol% or 70 to 85 mol%.
  • the resin composition has even more excellent alkali solubility and can form a resin film having a good pattern shape.
  • the content of the structural unit derived from the monomer having a hydroxyalkyl group and an ethylenically unsaturated group in the polymer (A) is preferably 1 to 20 mol%, more preferably 5 to 15 mol%. .. If necessary, it may be 5 to 10 mol% or 10 to 15 mol%.
  • the total content of the structural units is 1 mol% or more, the polymer purity is high and the resin composition has good developability, which is preferable.
  • the total content of the structural units is 20 mol% or less, the contents of the structural unit derived from the hydroxyphenyl (meth) acrylate and the structural unit derived from the phenylenedi (meth) acrylate are relatively increased. It is preferable because good heat resistance can be ensured.
  • the polymer (A) is other than the above three types in order to adjust transparency, heat resistance, adhesion, chemical resistance, electrical properties, refractive index, coatability, developability, storage stability, mechanical strength, etc. It may contain a structural unit derived from another ethylenically unsaturated group-containing monomer.
  • Examples of the constituent units derived from other ethylenically unsaturated group-containing monomers include styrene compounds such as styrene, methylstyrene, and methoxystyrene; methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and 2-.
  • Alkyl (meth) acrylates such as ethylhexyl (meth) acrylate and n-stearyl (meth) acrylate; glycidyl (meth) acrylate, glycidyl ⁇ -ethylacrylate, (meth) acrylic acid-3,4-epoxybutyl, vinyl glycidyl ether.
  • the polymer (A) may contain only one type of structural unit derived from other ethylenically unsaturated group-containing monomers, or may contain two or more types.
  • a configuration derived from one or more selected from styrene compounds, alkyl (meth) acrylates, and glycidyl (meth) acrylates from the viewpoint of adjusting alkali developability, a configuration derived from one or more selected from styrene compounds, alkyl (meth) acrylates, and glycidyl (meth) acrylates. It preferably contains a unit, particularly preferably a structural unit derived from one or more selected from styrene, methyl (meth) acrylate, and glycidyl (meth) acrylate.
  • the content of the structural unit derived from the other ethylenically unsaturated group-containing monomer in the polymer (A) is preferably 5 to 45 mol%, more preferably 10 to 30 mol%.
  • the mass average molecular weight Mw of the polymer (A) is preferably 1500 to 20000, more preferably 3000 to 10000, and even more preferably 5000 to 8000. If necessary, it may be 5000 to 6500, 6500 to 8000, or the like.
  • a flat coating film can be obtained by applying the resin composition containing the polymer (A).
  • the resin composition has excellent developability and a good pattern shape can be obtained.
  • it is a resin composition that can obtain a resin film having good heat resistance. Further, when the mass average molecular weight is 20000 or less, the resin composition has good sensitivity and the pattern shape after development becomes good.
  • the molecular weight distribution (Mw / Mn) of the polymer (A) is preferably 1.1 to 5.0, more preferably 1.1 to 4.0, and 1.1 to 2.5. It is more preferable to have. If necessary, it may be 1.1 to 1.8, 1.8 to 2.5, or the like. When the molecular weight distribution is within the above range, a good pattern can be formed by exposing and developing the resin composition.
  • the method for producing the polymer (A) is not particularly limited, but for example, a monomer which is a raw material of the polymer (A) is used by a polymerization method such as radical polymerization, cationic polymerization, anionic polymerization, or coordination anionic polymerization.
  • a polymerization method such as radical polymerization, cationic polymerization, anionic polymerization, or coordination anionic polymerization.
  • a polymerization initiator is added to a solution obtained by mixing a monomer as a raw material of the polymer (A) with a solvent inert to the polymerization reaction at a concentration of 10 to 50% by mass, and the temperature is 70 to 120 ° C. It is preferable to use a method of radical polymerization by reacting at temperature for 5 to 10 hours.
  • the content (molar ratio) of the constituent units derived from each monomer of the polymer (A) corresponds to the molar ratio of the monomer as the raw material of the polymer (A). Therefore, by adjusting the type and molar ratio of the monomer as the raw material of the polymer (A), the polymer (A) containing a predetermined structural unit in a predetermined content (molar ratio) can be obtained.
  • Examples of the polymerization initiator used in producing the polymer (A) include 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2-butyronitrile), and 2,2.
  • Azo-based initiators such as'-azobisisobutyronitrile, dimethyl-2,2'-azobisisobutyrate, and 1,1'-azobis (cyclohexane-1-carbonitrile); benzoyl peroxide, laurylper Organic peroxides such as oxides, octanoyl peroxides, acetyl peroxides, di-t-butyl peroxides, t-butyl cumyl peroxides, dicumyl peroxides, t-butyl peroxyacetates, and t-butyl peroxybenzoates. Things can be mentioned.
  • the amount of the polymerization initiator used in producing the polymer (A) is preferably 1 to 15 parts by mass, preferably 1 to 13 parts by mass, based on 100 parts by mass of the total amount of the monomers which are the raw materials of the polymer (A). Is more preferable, and 2 to 10 parts by mass is further preferable. If necessary, it may be 1 to 5 parts by mass, 5 to 8 parts by mass, 8 to 12 parts by mass, or the like.
  • Solvents used in producing the polymer (A) include methanol, ethanol, 1-propanol, isopropyl alcohol, butanol, ethylene glycol, acetone, methyl ethyl ketone, methyl isobutyl ketone, tetrahydrofuran, dioxane, toluene, xylene, ethyl acetate, and the like.
  • a chain transfer agent may be used for the purpose of adjusting the molecular weight.
  • the chain transfer agent include alkyl mercaptans such as octyl mercaptan, nonyl mercaptan, decyl mercaptan, and dodecyl mercaptan.
  • the resin composition of the present embodiment may contain a photosensitive component (B), if necessary.
  • the resin composition of the present embodiment can be used as a photosensitive resin composition by containing the photosensitive component (B).
  • the photosensitive component (B) may be a component having photosensitivity and is not particularly limited, but it is preferable to use a quinonediazide group-containing compound.
  • the quinonediazide group-containing compound suppresses alkali solubility in the unexposed portion of the coating film formed by applying the resin composition. Further, the quinonediazide group-containing compound generates a carboxylic acid in the exposed portion of the coating film formed by applying the resin composition to improve the alkali solubility of the coating film and enable the formation of a positive pattern.
  • quinonediazide group-containing compound for example, a condensate of a hydroxy group-containing compound having a phenolic hydroxyl group or an alcoholic hydroxyl group and 1,2-naphthoquinonediazide sulfonic acid halide is a preferable example.
  • 1,2-naphthoquinone diazide sulfonic acid ester of 2,3,4-trihydroxybenzophenone 1,2-naphthoquinone diazido sulfonic acid ester of 2,2', 4,4'-tetrahydroxybenzophenone, 2 , 3,4,4'-Tetrahydroxy-3'-methoxybenzophenone 1,2-naphthoquinone diazidosulfonic acid ester, 2,4,6,3', 4', 5'-hexahydroxybenzophenone 1,2- Naftquinone diazide sulfonic acid ester, 1,2-naphthoquinone diazido sulfonic acid ester of 2-methyl-2- (2,4-dihydroxyphenyl) -4- (4-hydroxyphenyl) -7-hydroxychroman, 2- [bis ⁇ (5-Isopropyl-4-hydroxy-2-methyl) phenyl ⁇ methyl] 1,2-nap
  • quinonediazide group-containing compound 1- [1- (4-hydroxyphenyl) isopropyl] -4- [1,1-bis (4-hydroxyphenyl) ethyl] benzene-1,2 because of its high photosensitivity. It is preferable to use -naphthoquinone diazide-5-sulfonic acid ester.
  • the content of the photosensitive component (B) is preferably 5 to 60 parts by mass and more preferably 10 to 50 parts by mass with respect to 100 parts by mass of the polymer (A). If necessary, it may be 10 to 15 parts by mass, 15 to 25 parts by mass, 25 to 35 parts by mass, 35 to 50 parts by mass, or the like. When the content of the photosensitive component (B) is 5 parts by mass or more, better developability can be obtained. Further, when the content of the photosensitive component (B) is 60 parts by mass or less, the transparency, insulating property, flatness and the like of the coating film made of the resin composition become better.
  • thermosetting resin (C) The resin composition of the present embodiment may contain a thermosetting resin (C), if necessary.
  • the thermosetting resin (C) is used as a cross-linking component for cross-linking the resin composition.
  • thermosetting resin (C) examples include methylated melamine resin, methylolated melamine resin, methylolated urea resin, methylolated benzoguanamine resin, alkoxyalkylated melamine resin, alkoxyalkylated urea resin, and alkoxyalkylated benzoguanamine resin.
  • examples thereof include methylolated phenol resins, alkoxyalkylated phenol resins, epoxy compounds, aziridine compounds, cyanate compounds, isocyanate compounds, oxazoline compounds, acid anhydride group-containing compounds, and formyl group-containing compounds.
  • thermosetting resins (C) nitrogen-containing compounds such as alkoxyalkylated urea resin and alkoxyalkylated melamine resin, and / or epoxy compounds are preferable in that they provide a resin composition having excellent stability.
  • These thermosetting resins (C) may be used alone or in combination of two or more.
  • the content of the thermosetting resin (C) is preferably 1 to 20 parts by mass, more preferably 5 to 15 parts by mass with respect to 100 parts by mass of the polymer (A). If necessary, it may be 5 to 10 parts by mass, 10 to 15 parts by mass, or the like.
  • the content of the thermosetting resin (C) is 1 part by mass or more, the heat resistance, chemical resistance, insulating property, etc. of the resin film formed by applying the resin composition are further improved. Further, when the content of the thermosetting resin (C) is 20 parts by mass or less, the developability of the resin composition becomes even better.
  • the resin composition of the present invention contains, if necessary, a solvent and an ultraviolet absorber.
  • Sensitives, sensitizers, plasticizers, thickeners, dispersants, defoamers, surfactants, adhesion aids, thermosetting acid-producing compounds, colorants and other other ingredients Good.
  • the solvent a solvent that dissolves each component uniformly and does not react with each component contained in the resin composition.
  • the solvent the same solvent as those exemplified as the solvent used in producing the polymer (A) described above can be mentioned.
  • diethylene glycol ethyl methyl ether, diethylene glycol dimethyl ether, propylene glycol monomethyl ether, purpyrene glycol monomethyl ether acetate, methyl-3-methoxypropionate, methyl methoxypropionate, and ethyl ethoxypropionate are contained in the resin composition.
  • a high boiling point solvent such as N-methylpyrrolidone, ⁇ -butyrolactone, N, N-dimethylacetamide is used. It may be used together.
  • the solvent is preferably used in the range of 100 to 4000 parts by mass and 200 to 1000 parts by mass with respect to a total of 100 parts by mass of the components other than the solvent in the resin composition. Is more preferable.
  • the resin film of the present embodiment is made of a cured product of the resin composition of the present embodiment.
  • the resin film of the present embodiment is formed by applying at least one of light and heat to the resin composition of the present embodiment to cure the resin composition.
  • a resin film containing a polymer (A), a photosensitive component (B), and a thermosetting resin (C) is used, and a resin film having a predetermined pattern shape such as an interlayer insulating film is used.
  • a resin film having a predetermined pattern shape such as an interlayer insulating film is used.
  • the following steps (1) to (7) can be formed in this order.
  • the steps (4) and (6) are arbitrary steps and may be performed as needed.
  • Step (1) A resin composition is applied onto the substrate so that the thickness after curing (thickness of the resin film) becomes a desired thickness.
  • Step (2) A coating film is formed by baking (pre-baking) a substrate coated with the resin composition.
  • Step (3) A part of the coating film made of the resin composition is exposed by irradiating it with active light rays or radiation.
  • Step (4) The substrate having the coating film after exposure is post-heated.
  • Step (5) The coating film after exposure is developed with a developing solution.
  • Step (6) The entire surface of the developed coating film is exposed.
  • Step (7) The substrate having the developed coating film is heated to thermoset (post-bake) the coating film.
  • the substrate used in the step (1) can be selected according to the application of the resin film.
  • a semiconductor substrate such as a silicon wafer, a ceramic substrate, a glass substrate, a metal substrate, a resin substrate, or the like is used.
  • a method for applying the resin composition a known method can be used.
  • examples of the method for applying the resin composition include a spray method, a roll coating method, a rotary coating method, and a bar coating method.
  • the thickness of the resin composition applied can be, for example, such that the thickness after curing (thickness of the resin film) is 0.1 to 30 ⁇ m.
  • Step (2) is performed to evaporate the solvent in the resin composition applied on the substrate.
  • the temperature and time of the prebake can be appropriately determined according to the type and content ratio of each component in the resin composition, the thickness of the applied resin composition, and the like. It is appropriate to heat the prebake at a temperature of 60 to 130 ° C. for 30 seconds to 15 minutes, for example.
  • the film thickness at the time of completion of prebaking is preferably in the range of, for example, 1 to 6 ⁇ m.
  • the coating film made of the resin composition formed through the steps (1) and (2) is exposed to active light or radiation through a mask having a predetermined pattern.
  • active light beam or radiation include g-ray (wavelength 436 nm), i-ray (wavelength 365 nm), KrF excimer laser, ArF excimer laser, X-ray, electron beam and the like.
  • the light source of active light or radiation include a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a chemical lamp, an excimer laser generator, and the like.
  • the exposure energy is generally 10 mJ / cm 2 to 1000 mJ / cm 2 , and preferably 20 mJ / cm 2 to 500 mJ / cm 2 energy.
  • a region developed by the developing solution and a region not developed by the developing solution are formed on the coating film on the substrate.
  • the exposed portion becomes a region developed by an aqueous developer.
  • step (4) for example, heating is performed at a temperature of 70 to 130 ° C. for several seconds to several minutes, and then heating is performed as necessary.
  • step (5) the exposed coating film is developed with a developing solution.
  • the region of the coating film that is developed by the developer is dissolved, and the region that is not developed by the developer remains on the substrate.
  • a coating film having a desired pattern shape is formed.
  • Examples of the developing solution used in the step (5) include sodium hydroxide, potassium hydroxide, sodium silicate, sodium metasilicate, ammonia, ethylamine, n-propylamine, diethylamine, diethylaminoethanol, di-n-propylamine, and the like.
  • An aqueous developer such as an aqueous solution of an alkali (basic compound) such as -diazabicyclo [4,3,0] -none-5-ene can be used.
  • an aqueous solution obtained by adding an appropriate amount of a water-soluble organic solvent such as methanol or ethanol and / or a surfactant to the above alkaline aqueous solution may be used.
  • step (5) as a developing method, a liquid filling method, a dipping method, a rocking dipping method, a shower method, or the like can be appropriately used.
  • the developing time can be appropriately determined depending on the composition of the resin composition, the type of developing solution, and the like.
  • the developing time can be, for example, 30 to 120 seconds.
  • it is preferable to perform a rinsing treatment by, for example, running water washing on the coating film patterned in a desired pattern shape.
  • Step (6) is performed as needed.
  • the photosensitive component (B) remaining in the patterned coating film can be decomposed.
  • the light transmittance of the coating film is improved.
  • the exposure energy in the case of full-scale exposure is preferably 100 to 1000 mJ / cm 2 .
  • the developed coating film is heated by a hot plate, an oven, or the like to thermoset (post-bake) the developed coating film.
  • the temperature of the post-bake is preferably 120 to 250 ° C. in order to thermoset the developed coating film.
  • the post-baking time is appropriately determined according to the type of heating equipment and the like. For example, when the treatment of heating the substrate having the developed coating film on the hot plate is performed, it is appropriate to carry out the treatment for 5 to 30 minutes. For example, when heat-treating a substrate having a developed coating film in an oven, it is appropriate to carry out the heat treatment for 30 to 90 minutes.
  • the resin film formed on the substrate in this way is made of a cured product of the resin composition of the present embodiment, it is excellent in insulating properties, transparency, and heat resistance. Therefore, the resin film of the present embodiment is a flattening film, an interlayer insulating film, a protective film in electronic components such as an organic electroluminescence (EL) display device, a liquid crystal display device, a magnetic head element, an integrated circuit element, and a solid-state imaging device. It can be used for various purposes such as microlenses. In particular, the resin film of the present embodiment is suitable for the flattening film and the interlayer insulating film of the organic EL display device and the liquid crystal display device.
  • EL organic electroluminescence
  • the resin film of the present embodiment when the resin composition of the present embodiment contains a colorant, the resin film of the present embodiment composed of the cured product has excellent insulating properties and heat resistance, and also has good color reproducibility. Therefore, the resin film of the present embodiment is a black PDL (Pixel Defining Layer), a black matrix, in electronic components such as an organic electroluminescence (EL) display device, a liquid crystal display device, a magnetic head element, an integrated circuit element, and a solid-state imaging device. It can be used as a material for color filters, black column spacers, and the like.
  • EL organic electroluminescence
  • the mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the obtained polymer [A-1] were measured by the methods shown below.
  • the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-1] was 7,100, and the molecular weight distribution (Mw / Mn) was 1.9.
  • the polymer purity of the polymer [A-1] was calculated from the area percentage of the polymer component excluding the residual monomer by gel permission chromatography (GPC). As a result, the polymer purity was 90%.
  • the mass average molecular weight (Mw) and the molecular weight distribution (Mw / Mn) of the obtained polymer [A-2] were measured by the same method as that of the polymer [A-1].
  • the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-2] was 6,800, and the molecular weight distribution (Mw / Mn) was 1.9.
  • the polymer purity of the polymer [A-2] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 91%.
  • the mass average molecular weight (Mw) and the molecular weight distribution (Mw / Mn) of the obtained polymer [A-3] were measured by the same method as that of the polymer [A-1].
  • the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-3] was 6,900, and the molecular weight distribution (Mw / Mn) was 2.0.
  • the polymer purity of the polymer [A-3] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 90%.
  • the mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the obtained polymer [A-4] were measured by the same method as that of the polymer [A-1].
  • the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-4] was 6,700, and the molecular weight distribution (Mw / Mn) was 1.9.
  • the polymer purity of the polymer [A-4] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 92%.
  • the mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the obtained polymer [A-5] were measured by the same method as that of the polymer [A-1].
  • the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-5] was 7,100, and the molecular weight distribution (Mw / Mn) was 2.0.
  • the polymer purity of the polymer [A-5] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 95%.
  • the mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the obtained polymer [A-6] were measured by the same method as that of the polymer [A-1].
  • Mw polystyrene-equivalent mass average molecular weight
  • Mw / Mn molecular weight distribution
  • the polymer purity of the polymer [A-6] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 91%.
  • the mass average molecular weight (Mw) and the molecular weight distribution (Mw / Mn) of the obtained polymer [A-7] were measured by the same method as that of the polymer [A-1].
  • the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-7] was 6,900, and the molecular weight distribution (Mw / Mn) was 1.9.
  • the polymer purity of the polymer [A-7] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 92%.
  • the mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the obtained polymer [A-8] were measured by the same method as that of the polymer [A-1].
  • the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-8] was 6,900, and the molecular weight distribution (Mw / Mn) was 1.8.
  • the polymer purity of the polymer [A-8] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 92%.
  • the mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the obtained polymer [A-10] were measured by the same method as that of the polymer [A-1].
  • Mw polystyrene-equivalent mass average molecular weight
  • Mw / Mn molecular weight distribution
  • the polymer purity of the polymer [A-10] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 88%.
  • the mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the obtained polymer [A-11] were measured by the same method as that of the polymer [A-1].
  • the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-11] was 7,100, and the molecular weight distribution (Mw / Mn) was 2.0.
  • the polymer purity of the polymer [A-11] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 89%.
  • Polymer [A-12] As the polymer [A-12], a hydroxystyrene polymer (trade name: Marukalinker MS-2 (manufactured by Maruzen Petrochemical Co., Ltd.)) was used. The mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the polymer [A-12] were measured by the same method as that of the polymer [A-1]. As a result, the polystyrene-equivalent mass average molecular weight (Mw) of the polymer [A-12] was 6,700, and the molecular weight distribution (Mw / Mn) was 2.0. Moreover, the polymer purity of the polymer [A-12] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 90%.
  • Marukalinker MS-2 manufactured by Maruzen Petrochemical Co., Ltd.
  • Polymer [A-13] A polymer [A-13] was obtained in the same manner as in Example 1 except that 1,4-phenylenedi methacrylate was not used.
  • the mass average molecular weight (Mw) and molecular weight distribution (Mw / Mn) of the obtained polymer [A-13] were measured by the same method as that of the polymer [A-1].
  • Mw mass average molecular weight
  • Mw / Mn molecular weight distribution
  • the polymer purity of the polymer [A-13] was calculated by the same method as that of the polymer [A-1]. As a result, the polymer purity was 87%.
  • Tables 1 and 2 show the molar ratio, mass average molecular weight (Mw), molecular weight distribution (Mw / Mn), and polymer purity of the monomers used as raw materials for the polymers [A-1] to [A-13].
  • the polymer purity of the polymers [A-1] to [A-13] was evaluated based on the criteria shown below. ⁇ : 92% or more ⁇ : 88-91% ⁇ : 87% or less
  • Example 1 100 parts by mass of a polymer solution (35% by mass concentration) containing the polymer [A-1] obtained by the above synthesis method and 1- [1- (4-hydroxyphenyl) isopropyl]-which is a photosensitive component.
  • a mixture of 2.10 parts by mass of Nicarac MW-30) manufactured by Waka Chemical Co., Ltd. was mixed with 80 parts by mass of methyl-3-methoxypropionate as a solvent and dissolved.
  • the obtained solution was filtered using a 0.2 ⁇ m membrane filter to prepare the photosensitive resin composition of Example 1.
  • Example 2 to 11 A polymer containing the polymers [A-2] to [A-11] obtained by the above synthesis method instead of 100 parts by mass of a polymer solution (35% by mass concentration) containing the polymer [A-1].
  • the photosensitive resin compositions of Examples 2 to 11 were prepared in the same manner as in Example 1 except that the solution (35% by mass concentration) was used.
  • Comparative Example 1 Instead of 100 parts by mass of the polymer solution (35% by mass) containing the polymer [A-1], 35% by mass of the polymer [A-12] using methyl-3-methoxypropionate as a solvent is contained.
  • the photosensitive resin composition of Comparative Example 1 was prepared in the same manner as in Example 1 except that the polymer solution was used.
  • Comparative Example 2 instead of 100 parts by mass of the polymer solution (35% by mass) containing the polymer [A-1], the polymer solution (35% by mass) containing the polymer [A-13] obtained by the above synthesis method ) was used, and the photosensitive resin composition of Comparative Example 2 was prepared in the same manner as in Example 1.
  • the photosensitive resin composition was applied onto a glass substrate so that the thickness after curing was 2.6 ⁇ m.
  • the glass substrate coated with the photosensitive resin composition was dried (prebaked) on a hot plate at a temperature of 110 ° C. for 90 seconds to form a coating film.
  • the dried coating film was irradiated with g-rays (436 nm) as active rays or radiation with an exposure energy of 200 mJ / cm 2 using an ultra-high pressure mercury lamp as a light source, and the entire surface was exposed.
  • the glass substrate having the coating film after exposure was placed in an oven, heated at 200 ° C. for 30 minutes, and heat-cured (post-baked) to obtain a resin film.
  • a spectrophotometer (UV-1650PC (manufactured by Shimadzu Corporation) was used to obtain a minimum transmittance of a wavelength of 400 to 800 nm, and the glass substrate was used as a blank. It was measured and evaluated according to the criteria shown below. ⁇ (Good): 95% or more ⁇ (Yes): 90-94% ⁇ (impossible): 89% or less
  • ⁇ Heat-resistant transparency> The glass substrate having the resin film used for the above evaluation of ⁇ transparency> was heat-treated again in air at 230 ° C. for 2 hours and further at 250 ° C. for 1 hour. Then, using a spectrophotometer (UV-1650PC (manufactured by Shimadzu Corporation)), the minimum transmittance at a wavelength of 400 to 800 nm was measured using a glass substrate as a blank, and evaluated according to the following criteria. ⁇ (Good): 93% or more ⁇ (Yes): 90-92% ⁇ (impossible): 89% or less
  • ⁇ Heat decomposition property> The film thickness of the glass substrate having the resin film used for the evaluation of the above ⁇ heat-resistant transparency> was measured. Then, the glass substrate having the resin film used for the evaluation of the above ⁇ heat-resistant transparency> was reheated by heating at 200 ° C. for 30 minutes. Then, the film thickness of the glass substrate having the resin film after reheating was measured, and the film thickness reduction rate of the resin film due to reheating was calculated using this, and evaluated according to the following criteria. ⁇ (Good): 10% or less ⁇ (Yes): 11 to 15% ⁇ (impossible): 16% or more
  • the photosensitive resin composition was applied onto the silicon wafer substrate so that the thickness after curing was 2.6 ⁇ m.
  • the silicon wafer substrate coated with the photosensitive resin composition was dried (prebaked) on a hot plate at a temperature of 110 ° C. for 90 seconds to form a coating film.
  • the dried coating film was irradiated with active light rays or g-rays (435 nm) as a light source with an exposure energy of 200 mJ / cm 2 using an ultra-high pressure mercury lamp as a light source, and the entire surface was exposed through a positive pattern mask.
  • the substrate having the coating film after exposure is immersed in a 2.38% tetramethylammonium hydroxide aqueous solution which is a developing solution to develop the coating film, and the coating film per unit time is developed from the development time of the 2.6 ⁇ m coating film.
  • the dissolution rate (nm / s) of the above was calculated and evaluated according to the criteria shown below. ⁇ (Good): 151-500 nm / s ⁇ (possible): 101-150 nm / s ⁇ (impossible): 100 nm / s or less
  • the photosensitive resin compositions of Examples 1 to 11 are all evaluated as ⁇ (good) or ⁇ (possible) in terms of transparency, heat-resistant transparency, heat-resistant decomposition, and alkali dissolution rate. )Met.
  • 7, 8, and Example 9 containing [A-9] which has a large number of constituent units derived from phenylenedi (meth) acrylate, was evaluated for transparency, heat-resistant transparency, heat-resistant decomposition, and alkali dissolution rate. It was good).
  • the photosensitive resin composition of Comparative Example 1 containing the polymer [A-12] containing no structural unit derived from hydroxyphenyl (meth) acrylate and a structural unit derived from phenylenedi (meth) acrylate is heat-resistant and transparent.
  • the evaluation of sex was ⁇ (impossible), and the heat resistance was insufficient.
  • the photosensitive resin composition of Comparative Example 2 containing the polymer [A-13] containing no structural unit derived from phenylenedi (meth) acrylate had a heat resistance evaluation of ⁇ (impossible), and was heat resistant. Was inadequate.
  • a resin composition capable of forming a resin film having excellent developability, transparency and heat resistance.
  • the resin film obtained by the present invention can be used for various purposes such as a flattening film, an interlayer insulating film, a protective film, and a microlens used in an organic EL display device and a liquid crystal display device.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition de résine contenant un polymère (A) qui comprend au moins une unité constitutive dérivée de (méth)acrylate d'hydroxyphényle et une unité constitutive dérivée de di(méth)acrylate de phénylène.
PCT/JP2020/011356 2019-05-30 2020-03-16 Composition de résine et film de résine WO2020240993A1 (fr)

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CN202080037012.5A CN113853394A (zh) 2019-05-30 2020-03-16 树脂组合物及树脂膜
CN202311653995.7A CN117467065A (zh) 2019-05-30 2020-03-16 树脂组合物及树脂膜
KR1020217036896A KR102645527B1 (ko) 2019-05-30 2020-03-16 수지 조성물 및 수지막
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Publication number Priority date Publication date Assignee Title
WO2023013128A1 (fr) * 2021-08-04 2023-02-09 日本化薬株式会社 Composition de résine contenant un composé durcissable de poids moléculaire élevé

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007033517A (ja) * 2005-07-22 2007-02-08 Showa Highpolymer Co Ltd 感光性の樹脂組成物
JP2007204448A (ja) * 2006-02-03 2007-08-16 Showa Highpolymer Co Ltd ヒドロキシフェニル（メタ）アクリレート組成物及びその製造方法
JP2012067059A (ja) * 2010-09-27 2012-04-05 Showa Denko Kk 二価フェノール類モノ（メタ）アクリレートを製造する方法
WO2013015055A1 (fr) * 2011-07-25 2013-01-31 昭和電工株式会社 Procédé de production d'un mono(méth)acrylate de diol aromatique
JP2015215453A (ja) * 2014-05-09 2015-12-03 日立化成株式会社 ネガ型感光性樹脂組成物、接着シート、接着剤パターン、接着剤層付半導体ウェハ及び半導体装置

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4204106B2 (ja) * 1998-08-12 2009-01-07 三菱レイヨン株式会社 被覆材組成物
CN104870499B (zh) * 2012-12-14 2016-11-23 昭和电工株式会社 共聚物、含有该共聚物的感光性树脂组合物及树脂膜
JP6451627B2 (ja) * 2014-03-11 2019-01-16 三菱ケミカル株式会社 活性エネルギー線硬化性樹脂組成物及び自動車ヘッドランプレンズ

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007033517A (ja) * 2005-07-22 2007-02-08 Showa Highpolymer Co Ltd 感光性の樹脂組成物
JP2007204448A (ja) * 2006-02-03 2007-08-16 Showa Highpolymer Co Ltd ヒドロキシフェニル（メタ）アクリレート組成物及びその製造方法
JP2012067059A (ja) * 2010-09-27 2012-04-05 Showa Denko Kk 二価フェノール類モノ（メタ）アクリレートを製造する方法
WO2013015055A1 (fr) * 2011-07-25 2013-01-31 昭和電工株式会社 Procédé de production d'un mono(méth)acrylate de diol aromatique
JP2015215453A (ja) * 2014-05-09 2015-12-03 日立化成株式会社 ネガ型感光性樹脂組成物、接着シート、接着剤パターン、接着剤層付半導体ウェハ及び半導体装置

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023013128A1 (fr) * 2021-08-04 2023-02-09 日本化薬株式会社 Composition de résine contenant un composé durcissable de poids moléculaire élevé

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KR102645527B1 (ko) 2024-03-11
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