WO2018230144A1 - 酸基含有（メタ）アクリレート樹脂及びソルダーレジスト用樹脂材料 - Google Patents

酸基含有（メタ）アクリレート樹脂及びソルダーレジスト用樹脂材料 Download PDF

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WO2018230144A1
WO2018230144A1 PCT/JP2018/015821 JP2018015821W WO2018230144A1 WO 2018230144 A1 WO2018230144 A1 WO 2018230144A1 JP 2018015821 W JP2018015821 W JP 2018015821W WO 2018230144 A1 WO2018230144 A1 WO 2018230144A1
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meth
acid
acrylate
group
resin
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PCT/JP2018/015821
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English (en)
French (fr)
Japanese (ja)
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駿介 山田
裕美子 中村
亀山　裕史
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Dic株式会社
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Priority to KR1020197031313A priority Critical patent/KR102425174B1/ko
Priority to JP2019506531A priority patent/JP6579412B2/ja
Priority to CN201880038705.9A priority patent/CN110753712B/zh
Publication of WO2018230144A1 publication Critical patent/WO2018230144A1/ja

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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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/14—Polyamide-imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/285—Permanent coating compositions
    • H05K3/287—Photosensitive compositions

Definitions

  • the present invention provides an acid group-containing (meth) acrylate resin having high heat resistance and high elongation in a cured product, a curable resin composition containing the resin, an insulating material comprising the curable resin composition, a resin material for solder resist, and The present invention relates to a resist member.
  • solder resist resin materials As a resin material for a solder resist for a printed wiring board, an acid group-containing epoxy acrylate resin obtained by reacting an acid anhydride after an epoxy resin is acrylated with acrylic acid is widely used. Performance requirements for solder resist resin materials include curing with a small amount of exposure, excellent alkali developability, excellent heat resistance and strength, flexibility, elongation, dielectric properties, substrate adhesion, etc. in cured products, etc. There are various things.
  • Patent Document 1 As a conventionally known resin material for solder resist, an acid group-containing epoxy acrylate resin obtained by reacting a novolak-type epoxy resin with acrylic acid and tetrahydrophthalic anhydride is known (see Patent Document 1 below).
  • the acid group-containing epoxy acrylate resin described in Patent Document 1 has characteristics such as high heat resistance in a cured product due to the novolac type epoxy resin that is a reaction raw material, it is not sufficient for the recent market demand. .
  • the elongation of the cured product is very low, there is a problem that the cured product is easily cracked and has poor reliability.
  • the problem to be solved by the present invention is to provide an acid group-containing (meth) acrylate resin having high heat resistance and high elongation in a cured product, a curable resin composition containing the same, and an insulation comprising the curable resin composition.
  • the object is to provide a material, a resin material for solder resist, and a resist member.
  • the present inventors have reacted an amidoimide resin with a hydroxy (meth) acrylate and a (meth) acryloyl group-containing epoxy compound to introduce a (meth) acryloyl group,
  • the acid group-containing (meth) acrylate resin obtained by reacting the carboxylic acid anhydride was found to have very high heat resistance and elongation in the cured product, and the present invention was completed.
  • the present invention relates to an amidoimide resin (A) having an acid group or an acid anhydride group, a hydroxy (meth) acrylate compound (B), a (meth) acryloyl group-containing epoxy compound (C), and a polycarboxylic acid anhydride (D ) As an essential reaction raw material.
  • the present invention further relates to a curable resin composition containing the acid group-containing (meth) acrylate resin and a photopolymerization initiator.
  • the present invention further relates to a cured product of the curable resin composition.
  • the present invention further relates to an insulating material comprising the curable resin composition.
  • the present invention further relates to a solder resist resin material comprising the curable resin composition.
  • the present invention further relates to a resist member made of the resin material for solder resist.
  • an acid group-containing (meth) acrylate resin having high heat resistance and high elongation in a cured product a curable resin composition containing the resin, an insulating material comprising the curable resin composition, and a resin for a solder resist Materials and resist members can be provided.
  • FIG. 1 is a GPC chart of the acid group-containing (meth) acrylate resin (1) obtained in Example 1.
  • FIG. 1 is a GPC chart of the acid group-containing (meth) acrylate resin (1) obtained in Example 1.
  • the acid group-containing (meth) acrylate resin of the present invention includes an amideimide resin (A) having an acid group or an acid anhydride group, a hydroxy (meth) acrylate compound (B), a (meth) acryloyl group-containing epoxy compound (C), and The polycarboxylic anhydride (D) is used as an essential reaction raw material.
  • the (meth) acrylate resin refers to a resin having an acryloyl group, a methacryloyl group, or both in the molecule.
  • the (meth) acryloyl group means one or both of an acryloyl group and a methacryloyl group, and (meth) acrylate is a general term for acrylate and methacrylate.
  • the amidoimide resin (A) having an acid group or an acid anhydride group may have only one of an acid group or an acid anhydride group, or may have both.
  • an acid anhydride group it is preferable to have an acid anhydride group. It preferably has both a group and an acid anhydride group.
  • the acid value of the amideimide resin (A) is preferably in the range of 60 to 350 mgKOH / g under neutral conditions, that is, under conditions where the acid anhydride group is not ring-opened.
  • the measured value under the condition where the acid anhydride group is opened, such as in the presence of water is preferably in the range of 61 to 360 mgKOH / g.
  • the specific structure and production method of the amideimide resin (A) are not particularly limited, and general amideimide resins and the like can be widely used. Specifically, what uses polyisocyanate compound (a1) and polycarboxylic acid or its acid anhydride (a2) as a reaction raw material is mentioned.
  • polyisocyanate compound (a1) examples include aliphatic diisocyanate compounds such as butane diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,4,4-trimethylhexamethylene diisocyanate; norbornane diisocyanate, isophorone Cycloaliphatic diisocyanate compounds such as diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate; tolylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, 4,4′-diisocyanate Aromatic dimers such as -3,3'-dimethylbiphenyl and o-tolidine diisocyanate Isocyanate compounds; polymethylene polyphenyl
  • R 1 is independently a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms.
  • R 2 is each independently an alkyl group having 1 to 4 carbon atoms, or a bonding point that is linked to the structural moiety represented by the structural formula (1) via a methylene group marked with *.
  • l is 0 or an integer of 1 to 3
  • m is an integer of 1 or more.
  • the alicyclic diisocyanate compound or a modified product thereof is preferable, and an alicyclic diisocyanate or an isocyanurate modified product thereof is preferable in that it becomes an acid group-containing (meth) acrylate resin having high solvent solubility.
  • the said aliphatic diisocyanate compound or its modified body is preferable at the point used as an acid group containing (meth) acrylate resin with the very high elongation in hardened
  • the ratio of the total mass of the alicyclic diisocyanate compound or a modified product thereof and the aliphatic diisocyanate compound or the modified product with respect to the total mass of the polyisocyanate compound (a1) is 70% by mass or more, It is preferable that it is 90 mass% or more.
  • the mass ratio of the two is preferably in the range of 30/70 to 70/30.
  • the polycarboxylic acid or its acid anhydride (a2) is not particularly limited as long as it is a compound having a plurality of carboxy groups in its molecular structure or its acid anhydride, and a wide variety of compounds can be used. Moreover, polycarboxylic acid or its acid anhydride (a2) may each be used independently, and may use 2 or more types together.
  • the amidoimide resin (A) it is necessary that both a carboxy group and an acid anhydride group exist in the system.
  • a compound having both a carboxy group and an acid anhydride group may be used, or a compound having a carboxy group and a compound having an acid anhydride group may be used in combination.
  • polycarboxylic acid or its acid anhydride (a2) examples include, for example, an aliphatic polycarboxylic acid compound or its acid anhydride, an alicyclic polycarboxylic acid compound or its acid anhydride, and an aromatic polycarboxylic acid compound. Or the acid anhydride etc. are mentioned.
  • the aliphatic polycarboxylic acid compound or the acid anhydride thereof the aliphatic hydrocarbon group may be either a straight chain type or a branched type, and may have an unsaturated bond in the structure.
  • Examples of the aliphatic polycarboxylic acid compound or its acid anhydride include, for example, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid.
  • Examples thereof include acids, citraconic acid, itaconic acid, glutaconic acid, 1,2,3,4-butanetetracarboxylic acid, and acid anhydrides thereof.
  • the alicyclic polycarboxylic acid compound or anhydride thereof is a compound in which a carboxy group or an acid anhydride group is bonded to an alicyclic structure. The presence or absence of an aromatic ring at any other structural site is not questioned.
  • Examples of the alicyclic polycarboxylic acid compound or its anhydride include, for example, tetrahydrophthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, cyclohexanetricarboxylic acid, cyclohexanetetracarboxylic acid, bicyclo [2.2.1 ] Heptane-2,3-dicarboxylic acid, methylbicyclo [2.2.1] heptane-2,3-dicarboxylic acid, 4- (2,5-dioxotetrahydrofuran-3-yl) -1,2,3 Examples thereof include 4-tetrahydronaphthalene-1,2-dicarboxylic acid and acid anhydrides thereof.
  • aromatic polycarboxylic acid compound or acid anhydride thereof examples include, for example, phthalic acid, trimellitic acid, pyromellitic acid, naphthalene dicarboxylic acid, naphthalene tricarboxylic acid, naphthalene tetracarboxylic acid, biphenyl dicarboxylic acid, biphenyl tricarboxylic acid , Biphenyltetracarboxylic acid, benzophenonetetracarboxylic acid and the like.
  • the alicyclic polycarboxylic acid compound or its acid anhydride, or the aromatic polycarboxylic acid compound or its acid anhydride is preferable because it becomes an acid group-containing (meth) acrylate resin having particularly high heat resistance.
  • the said amideimide resin (A) can be manufactured efficiently, it is preferable to use the tricarboxylic acid anhydride which has both a carboxy group and an acid anhydride group in molecular structure, and a cyclohexane tricarboxylic acid anhydride or trimellit is used. It is particularly preferable to use an acid anhydride.
  • the ratio of the total amount of the alicyclic tricarboxylic acid anhydride and the aromatic tricarboxylic acid anhydride to the total mass of the polycarboxylic acid or acid anhydride (a2) is preferably 70% by mass or more, 90 It is preferable that it is mass% or more.
  • the amide-imide resin (A) uses the polyisocyanate compound (a1) and the polycarboxylic acid or acid anhydride (a2) as a reaction raw material, the reaction other than these depending on the desired resin performance You may use a raw material together.
  • the polyisocyanate compound (a1) and the polycarboxylic acid or acid anhydride (a2) thereof with respect to the total reaction raw material mass of the amideimide resin (A) The ratio of the total mass is preferably 90% by mass or more, and preferably 95% by mass or more.
  • the production method is not particularly limited, and any method is used. It may be manufactured. For example, it can be produced by the same method as a general amideimide resin. Specifically, 0.8 to 1.2 mol of the polycarboxylic acid or acid anhydride (a2) is used at about 120 to 180 ° C. with respect to 1 mol of the isocyanate group of the polyisocyanate compound (a1). A method of stirring and mixing under the following temperature conditions is mentioned.
  • the reaction may be performed in an organic solvent as necessary.
  • the selection of the organic solvent to be used is appropriately selected depending on the reaction raw material and the solubility of the acid group-containing (meth) acrylate resin that is the product, reaction temperature conditions, etc., for example, methyl ethyl ketone, acetone, dimethylformamide, methyl isobutyl ketone, Examples include methoxypropanol, cyclohexanone, methyl cellosolve, dialkylene glycol monoalkyl ether acetate, dialkylene glycol acetate and the like. These may be used alone or as a mixed solvent of two or more.
  • the amount of the organic solvent used is preferably in the range of about 0.1 to 5 times the total mass of the reaction raw materials because the reaction efficiency is good.
  • the hydroxy (meth) acrylate compound (B) is not particularly limited as long as it has a hydroxyl group and a (meth) acryloyl group in the molecular structure, and a wide variety of compounds can be used. Moreover, the said hydroxy (meth) acrylate compound (B) may be used independently, respectively and may use 2 or more types together. Among these, a monohydroxy (meth) acrylate compound is preferable because the reaction can be easily controlled.
  • (Poly) oxyalkylene-modified products in which (poly) oxyalkylene chains are introduced; lactone-modified products in which (poly) lactone structures are introduced into the molecular structures of the various hydroxy (meth) acrylate compounds, and the like. That. These may be used alone or in combination of two or more. Especially, since it becomes an acid group containing (meth) acrylate resin excellent in the balance of the heat resistance and elongation in hardened
  • the (meth) acryloyl group-containing epoxy compound (C) has a (meth) acryloyl group and an epoxy group in the molecular structure
  • other specific structures are not particularly limited, and a wide variety of compounds should be used. Can do.
  • the said (meth) acryloyl group containing epoxy compound (C) may be used independently, respectively and may use 2 or more types together. Among these, a monoepoxy compound is preferable because the reaction can be easily controlled.
  • Examples thereof include glycidyl group-containing (meth) acrylate monomers such as glycidyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether, and epoxycyclohexylmethyl (meth) acrylate; dihydroxybenzene diglycidyl ether, dihydroxy And mono (meth) acrylates of diglycidyl ether compounds such as naphthalene diglycidyl ether, biphenol diglycidyl ether, and bisphenol diglycidyl ether.
  • glycidyl group-containing (meth) acrylate monomers such as glycidyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether, and epoxycyclohexylmethyl (meth) acrylate
  • dihydroxybenzene diglycidyl ether dihydroxy And mono (meth) acrylates of diglycidyl ether compounds such as
  • the glycidyl group-containing (meth) acrylate monomer is preferable because the acid group-containing (meth) acrylate resin is excellent in the balance between heat resistance and elongation in the cured product.
  • the molecular weight is preferably 500 or less.
  • the ratio of the glycidyl group-containing (meth) acrylate monomer to the total mass of the (meth) acryloyl group-containing epoxy compound (C) is preferably 70% by mass or more, and more preferably 90% by mass or more.
  • polycarboxylic acid anhydride (D) examples include acid anhydrides of the compounds exemplified as the polycarboxylic acid or acid anhydride (a2). Moreover, the said polycarboxylic acid anhydride (D) may be used independently, respectively, and may use 2 or more types together. Among them, since it becomes an acid group-containing (meth) acrylate compound having excellent developability in addition to heat resistance and elongation in the cured product, the aliphatic polycarboxylic acid anhydride or the alicyclic polycarboxylic acid anhydride is An aliphatic dicarboxylic acid anhydride or an alicyclic dicarboxylic acid anhydride is more preferable.
  • the acid group-containing (meth) acrylate resin of the present invention comprises an amide-imide resin (A) having the acid group or acid anhydride group, a hydroxy (meth) acrylate compound (B), (meta )
  • A amide-imide resin
  • B hydroxy (meth) acrylate compound
  • D polycarboxylic acid anhydride
  • other reaction raw materials may be used in combination.
  • the ratio of the total mass of the components (A) to (D) to the total mass of the reaction raw material of the acid group-containing (meth) acrylate resin is 80% by mass or more. It is preferable that it is 90 mass% or more.
  • the method for producing the acid group-containing (meth) acrylate resin is not particularly limited, and may be produced by any method. For example, it may be produced by a method in which all of the reaction raw materials are reacted together, or may be produced by a method in which the reaction raw materials are reacted sequentially. Among them, since the control of the reaction is easy, the amideimide resin (A) and the hydroxy (meth) acrylate compound (B) are reacted (step 1), and the product of step 1 and the (meth) acryloyl group are contained.
  • the epoxy compound (C) is preferably reacted (Step 2), and the product of Step 2 is preferably reacted with the polycarboxylic acid anhydride (D).
  • the amideimide resin (A) in reaction of the said amideimide resin (A) and the said hydroxy (meth) acrylate compound (B), mainly the acid group or acid anhydride group in the said amideimide resin (A), and hydroxy (meth).
  • the hydroxy group in the acrylate compound (B) is reacted. Since the hydroxy (meth) acrylate compound (B) is particularly excellent in reactivity with an acid anhydride group, as described above, the amideimide resin (A) preferably has an acid anhydride group.
  • the reaction ratio between the amideimide resin (A) and the hydroxy (meth) acrylate compound (B) is based on the total of acid groups and acid anhydride groups in the amideimide resin (A).
  • the content of the acid anhydride group in the amideimide resin (A) is the difference between the above-described two acid value measurement values, that is, the acid value under the condition where the acid anhydride group is opened, and the acid anhydride. It can be calculated from the difference from the acid value under conditions where the physical group is not ring-opened.
  • the reaction of the amideimide resin (A) and the hydroxy (meth) acrylate compound (B) can be performed, for example, by heating and stirring under a temperature condition of about 90 to 140 ° C. in the presence of a suitable esterification catalyst. it can.
  • esterification catalyst examples include phosphorus compounds such as trimethylphosphine, tributylphosphine, and triphenylphosphine, amine compounds such as triethylamine, tributylamine, and dimethylbenzylamine, 2-methylimidazole, 2-heptadecylimidazole, 2-ethyl- Examples thereof include imidazole compounds such as 4-methylimidazole, 1-benzyl-2-methylimidazole, and 1-isobutyl-2-methylimidazole. These may be used alone or in combination of two or more.
  • the amount of the catalyst added is preferably in the range of 0.001 to 5 parts by mass with respect to the total mass of the reaction raw materials.
  • the reaction may be performed in an organic solvent as necessary.
  • the selection of the organic solvent to be used is appropriately selected depending on the reaction raw material and the solubility of the acid group-containing (meth) acrylate resin that is the product, reaction temperature conditions, etc., for example, methyl ethyl ketone, acetone, dimethylformamide, methyl isobutyl ketone, Examples include methoxypropanol, cyclohexanone, methyl cellosolve, dialkylene glycol monoalkyl ether acetate, dialkylene glycol acetate and the like. These may be used alone or as a mixed solvent of two or more. In the case where the production of the amideimide resin (A) and Step 1 are continuously performed, the reaction may be continued as it is in the organic solvent used in the production of the amideimide resin (A).
  • the (meth) acryloyl group-containing epoxy compound (C) mainly reacts with the carboxy group in the product of Step 1.
  • the reaction ratio is preferably such that the (meth) acryloyl group-containing epoxy compound (C) is used in the range of 0.5 to 1.2 mol with respect to the carboxy group in the product of Step 1, from 0.9 to It is more preferable to use in the range of 1.1 mol.
  • the reaction in step 2 can be performed, for example, by heating and stirring under a temperature condition of about 90 to 140 ° C. in the presence of a suitable esterification catalyst. When step 1 and step 2 are continuously performed, the esterification catalyst may not be added or may be added as appropriate. Moreover, you may perform reaction in an organic solvent as needed.
  • the polycarboxylic anhydride (D) mainly reacts with a hydroxyl group in the product of Step 2.
  • the product of Step 2 for example, there are hydroxyl groups generated by ring opening of the epoxy group in the (meth) acryloyl group-containing epoxy compound (C).
  • the reaction rate of the polycarboxylic acid anhydride (D) is preferably adjusted so that the acid value of the acid group-containing (meth) acrylate resin as the final product is about 50 to 100 mgKOH / g.
  • the reaction in step 3 can be performed, for example, by heating and stirring under a temperature condition of about 90 to 140 ° C. in the presence of a suitable esterification catalyst.
  • the esterification catalyst may not be added or may be added as appropriate.
  • the acid value of the acid group-containing (meth) acrylate resin thus obtained is an acid group-containing (meth) acrylate resin that is excellent in developability and the like in addition to heat resistance and elongation in the cured product, 50
  • the range is preferably from 100 to 100 mgKOH / g, more preferably from 60 to 90 mgKOH / g.
  • the acid value of the acid group-containing (meth) acrylate resin is a value measured by a neutralization titration method of JIS K 0070 (1992).
  • the (meth) acryloyl group equivalent of the acid group-containing (meth) acrylate resin is preferably in the range of 250 to 750 g / equivalent, and more preferably in the range of 300 to 700 g / equivalent.
  • the mass average molecular weight (Mw) of the acid group-containing (meth) acrylate resin is preferably in the range of 1,000 to 10,000.
  • the molecular weight of the acid group-containing (meth) acrylate resin is a value measured by GPC measured under the following conditions.
  • Measuring device “HLC-8220 GPC” manufactured by Tosoh Corporation Column: Guard column “HXL-L” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + Tosoh Corporation “TSK-GEL G3000HXL” + “TSK-GEL G4000HXL” manufactured by Tosoh Corporation Detector: RI (differential refractometer) Data processing: “GPC-8020 Model II version 4.10” manufactured by Tosoh Corporation Measurement conditions: Column temperature 40 ° C Developing solvent Tetrahydrofuran Flow rate 1.0 ml / min Standard: The following monodisperse polystyrene having a known molecular weight was used according to the measurement manual of “GPC-8020 model II version 4.10”.
  • the acid group-containing (meth) acrylate resin of the present invention has a polymerizable (meth) acryloyl group in the molecular structure, for example, it can be used as a curable resin composition by adding a photopolymerization initiator. Can do.
  • the photopolymerization initiator may be selected and used according to the type of active energy ray to be irradiated. Moreover, you may use together with photosensitizers, such as an amine compound, a urea compound, a sulfur-containing compound, a phosphorus-containing compound, a chlorine-containing compound, a nitrile compound.
  • photosensitizers such as an amine compound, a urea compound, a sulfur-containing compound, a phosphorus-containing compound, a chlorine-containing compound, a nitrile compound.
  • photopolymerization initiator examples include, for example, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, 2- (dimethylamino) Alkylphenone photopolymerization initiators such as -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone; 2,4,6-trimethylbenzoyl-diphenyl- Examples include acylphosphine oxide photopolymerization initiators such as phosphine oxide; intramolecular hydrogen abstraction type photopolymerization initiators such as benzophenone compounds. These may be used alone or in combination of two or more.
  • the addition amount of the photopolymerization initiator is preferably in the range of 0.05 to 15% by mass, for example, in the range of 0.1 to 10% by mass with respect to the total of components other than the solvent of the curable resin composition. It is more preferable that
  • the curable resin composition of the present invention may contain a resin component other than the acid group-containing (meth) acrylate resin of the present invention.
  • the resin component is obtained, for example, by reacting an epoxy resin such as a bisphenol type epoxy resin or a novolak type epoxy resin with (meth) acrylic acid, dicarboxylic acid anhydride, and unsaturated monocarboxylic acid anhydride as required.
  • an epoxy resin such as a bisphenol type epoxy resin or a novolak type epoxy resin
  • acrylic acid, dicarboxylic acid anhydride dicarboxylic acid anhydride
  • unsaturated monocarboxylic acid anhydride unsaturated monocarboxylic acid anhydride
  • Examples of the (meth) acrylate monomer include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl ( Aliphatic mono (meth) acrylate compounds such as meth) acrylate and octyl (meth) acrylate; alicyclic mono (meth) acrylate compounds such as cyclohexyl (meth) acrylate, isobornyl (meth) acrylate and adamantyl mono (meth) acrylate; Heterocyclic mono (meth) acrylate compounds such as glycidyl (meth) acrylate and tetrahydrofurfuryl acrylate; benzyl (meth) acrylate, phenyl (meth) acrylate,
  • Aliphatic di (meth) acrylate compounds such as ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, butanediol di (meth) acrylate, hexanediol di (meth) acrylate and neopentyl glycol di (meth) acrylate 1,4-cyclohexanedimethanol di (meth) acrylate, norbornane di (meth) acrylate, norbornane dimethanol di (meth) acrylate, dicyclopentanyl di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate
  • alicyclic di (meth) acrylate compounds aromatic di (meth) acrylate compounds such as biphenol di (meth) acrylate and bisphenol di (meth) acrylate;
  • Aliphatic tri (meth) acrylate compounds such as trimethylolpropane tri (meth) acrylate and glycerin tri (meth) acrylate; (poly) oxyethylene chain in the molecular structure of the aliphatic tri (meth) acrylate compound, (poly) (Poly) oxyalkylene-modified tri (meth) acrylate compound introduced with (poly) oxyalkylene chain such as oxypropylene chain and (poly) oxytetramethylene chain; in the molecular structure of the aliphatic tri (meth) acrylate compound ( A lactone-modified tri (meth) acrylate compound having a poly) lactone structure;
  • Tetra- or higher functional aliphatic poly (meth) acrylate compounds such as pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate; (Poly) oxyalkylene-modified poly (meth) having 4 or more functionalities in which (poly) oxyethylene chain, (poly) oxypropylene chain, (poly) oxytetramethylene chain, or other (poly) oxyalkylene chain is introduced into the molecular structure Acrylate compounds; tetrafunctional or higher functional lactone-modified poly (meth) acrylate compounds in which a (poly) lactone structure is introduced into the molecular structure of the aliphatic poly (meth) acrylate compound.
  • the curable resin composition of the present invention may contain an organic solvent for the purpose of adjusting the coating viscosity.
  • the kind and addition amount are appropriately adjusted according to the desired performance. Generally, it is used in the range of 10 to 90% by mass with respect to the total of the curable resin composition.
  • Specific examples of the solvent include, for example, ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone; cyclic ether solvents such as tetrahydrofuran and dioxolane; esters such as methyl acetate, ethyl acetate and butyl acetate; aromatics such as toluene and xylene.
  • Solvents include cycloaliphatic, methylcyclohexane and other alicyclic solvents; carbitol, cellosolve, methanol, isopropanol, butanol, propylene glycol monomethyl ether and other alcohol solvents; alkylene glycol monoalkyl ether, dialkylene glycol monoalkyl ether, dialkylene glycol mono Examples include glycol ether solvents such as alkyl ether acetates. These may be used alone or in combination of two or more.
  • the curable resin composition of the present invention may contain various additives such as inorganic fine particles and polymer fine particles, pigments, antifoaming agents, viscosity modifiers, leveling agents, flame retardants, and storage stabilizers. .
  • the acid group-containing (meth) acrylate resin of the present invention is characterized by high heat resistance and elongation in a cured product. Furthermore, it has the characteristics which are excellent also in the developability evaluated by photosensitivity, a dry management width, etc., the base-material adhesiveness in hardened
  • thin film display applications such as LCD and OELD can be suitably used for thin film transistor protective films, liquid crystal color filter protective films, color filter pigment resists, black matrix resists, spacers, and the like.
  • the resin material for solder resist of the present invention includes, for example, each component such as a curing agent, a curing accelerator, and an organic solvent in addition to the acid group-containing (meth) acrylate resin, the photopolymerization initiator, and various additives. Become.
  • the curing agent is not particularly limited as long as it has a functional group capable of reacting with a carboxy group in the acid group-containing (meth) acrylate resin, and examples thereof include an epoxy resin.
  • examples of the epoxy resin used here include bisphenol type epoxy resin, phenylene ether type epoxy resin, naphthylene ether type epoxy resin, biphenyl type epoxy resin, triphenylmethane type epoxy resin, phenol novolac type epoxy resin, and cresol novolac type epoxy resin.
  • Bisphenol novolac type epoxy resin, naphthol novolak type epoxy resin, naphthol-phenol co-condensed novolac type epoxy resin, naphthol-cresol co-condensed novolac type epoxy resin, phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene-phenol Examples include addition reaction type epoxy resins. These may be used alone or in combination of two or more. Among these epoxy resins, phenolic novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol novolac type epoxy resin, naphthol novolac type epoxy resin, naphthol-phenol co-condensed novolak type epoxy resin because of excellent heat resistance in cured products.
  • Novolak type epoxy resins such as naphthol-cresol co-condensed novolak type epoxy resins are preferable, and those having a softening point in the range of 50 to 120 ° C. are particularly preferable.
  • the curing accelerator accelerates the curing reaction of the curing agent.
  • a phosphorus compound, a tertiary amine, an imidazole, an organic acid metal salt, a Lewis acid examples include amine complex salts. These may be used alone or in combination of two or more.
  • the addition amount of the curing accelerator is, for example, in the range of 1 to 10 parts by mass with respect to 100 parts by mass of the curing agent.
  • the organic solvent is not particularly limited as long as it can dissolve various components such as the acid group-containing (meth) acrylate resin and the curing agent.
  • methyl ethyl ketone, acetone, dimethylformamide, methyl isobutyl ketone, methoxypropanol examples include cyclohexanone, methyl cellosolve, diethylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate.
  • the method of obtaining a resist member using the solder resist resin material of the present invention is, for example, by applying the solder resist resin material on a substrate and evaporating and drying the organic solvent in a temperature range of about 60 to 100 ° C. Thereafter, there is a method in which a non-exposed portion is exposed with an ultraviolet solution or an electron beam through a photomask having a desired pattern formed, and an unexposed portion is developed with an alkaline aqueous solution, and further heated and cured in a temperature range of about 140 to 180 ° C. .
  • the acid value of the acid group-containing (meth) acrylate resin was measured by the neutralization titration method of JIS K 0070 (1992).
  • the molecular weight of the acid group-containing (meth) acrylate resin was measured by GPC under the following conditions.
  • Measuring device “HLC-8220 GPC” manufactured by Tosoh Corporation Column: Guard column “HXL-L” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + Tosoh Corporation “TSK-GEL G3000HXL” + “TSK-GEL G4000HXL” manufactured by Tosoh Corporation Detector: RI (differential refractometer) Data processing: “GPC-8020 Model II version 4.10” manufactured by Tosoh Corporation Measurement conditions: Column temperature 40 ° C Developing solvent Tetrahydrofuran Flow rate 1.0 ml / min Standard: The following monodisperse polystyrene having a known molecular weight was used according to the measurement manual of “GPC-8020 model II version 4.10”.
  • Example 1 Production of Acid Group-Containing (Meth) acrylate Resin (1)
  • a flask equipped with a thermometer, a stirrer, and a reflux condenser 449.7 parts by mass of diethylene glycol monomethyl ether acetate and an isocyanurate modified form of isophorone diisocyanate ( EVONIK's “VESTANAT T-1890 / 100”, isocyanate group content 17.2% by mass) 175.5 parts by mass, trimellitic anhydride 142.6 parts by mass, and dibutylhydroxytoluene 1.4 parts by mass are dissolved. I let you.
  • the acid group-containing (meth) acrylate resin (1) had a solid content acid value of 80 mg KOH / g, an acryloyl group equivalent of 485 g / equivalent, and a weight average molecular weight (Mw) of 5,200.
  • a GPC chart of the acid group-containing (meth) acrylate resin (1) is shown in FIG.
  • the acid group-containing (meth) acrylate resin (2) had a solid content acid value of 80 mg KOH / g, an acryloyl group equivalent of 445 g / equivalent, and a weight average molecular weight (Mw) of 4,700.
  • the acid group-containing (meth) acrylate resin (3) had a solid content acid value of 80 mg KOH / g, an acryloyl group equivalent of 415 g / equivalent, and a weight average molecular weight (Mw) of 4,980.
  • Example 4 Production of Acid Group-Containing (Meth) acrylate Resin (4)
  • a flask equipped with a thermometer, a stirrer, and a reflux condenser 300.2 parts by mass of diethylene glycol monomethyl ether acetate and a nurate-modified product of hexamethylene diisocyanate (DIC Corporation “Bernock DN901S” (isocyanate group content 23.5% by mass) 197.9 parts by mass, trimellitic anhydride 219.7 parts by mass, and dibutylhydroxytoluene 1.8 parts by mass were dissolved. It was made to react at 160 degreeC under nitrogen atmosphere for 5 hours, and it confirmed that isocyanate group content was 0.1 mass% or less.
  • the acid group-containing (meth) acrylate resin (4) had a solid content acid value of 80 mg KOH / g, an acryloyl group equivalent of 416 g / equivalent, and a weight average molecular weight (Mw) of 4,350.
  • Example 5 Production of acid group-containing (meth) acrylate resin (5)
  • 299.8 parts by mass of diethylene glycol monomethyl ether acetate 232.8 parts by mass of isophorone diisocyanate
  • Trimellitic anhydride 302.0 parts by mass and dibutylhydroxytoluene 1.8 parts by mass were added and dissolved. It was made to react at 160 degreeC under nitrogen atmosphere for 5 hours, and it confirmed that isocyanate group content was 0.1 mass% or less.
  • the acid group-containing (meth) acrylate resin (5) had a solid content acid value of 80 mg KOH / g, an acryloyl group equivalent of 603 g / equivalent, and a weight average molecular weight (Mw) of 1,780.
  • Example 6 Production of Acid Group-Containing (Meth) acrylate Resin (6)
  • a flask equipped with a thermometer, a stirrer, and a reflux condenser 1422.7 parts by mass of diethylene glycol monomethyl ether acetate and an isocyanurate modified form of isophorone diisocyanate ( EVONIK "VESTANAT T-1890 / 100", isocyanate group content 17.2% by mass) 753.2 parts by mass and cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride 644.2 parts by mass
  • 6.5 parts by mass of dibutylhydroxytoluene was added and dissolved.
  • Methoquinone 1.3 parts by mass, pentaerythritol polyacrylate mixture (“Aronix M-306” manufactured by Toagosei Co., Ltd., pentaerythritol triacrylate content about 67%, hydroxyl value 159.7 mg KOH / g) 189.2 parts by mass, tri 12.9 parts by mass of phenylphosphine was added and reacted at 110 ° C. for 5 hours while blowing air.
  • pentaerythritol polyacrylate mixture (“Aronix M-306” manufactured by Toagosei Co., Ltd., pentaerythritol triacrylate content about 67%, hydroxyl value 159.7 mg KOH / g) 189.2 parts by mass
  • tri 12.9 parts by mass of phenylphosphine was added and reacted at 110 ° C. for 5 hours while blowing air.
  • the acid group-containing (meth) acrylate resin (6) had a solid content acid value of 80 mgKOH / g, an acryloyl group equivalent of 434 g / equivalent, and a weight average molecular weight (Mw) of 5,600.
  • Example 7 Production of Acid Group-Containing (Meth) acrylate Resin (7)
  • a flask equipped with a thermometer, a stirrer, and a reflux condenser 449.7 parts by mass of diethylene glycol monomethyl ether acetate and an isocyanurate modified form of isophorone diisocyanate (EVONIK) “VESTANAT T-1890 / 100” manufactured by the company, isocyanate group content 17.2% by mass) 170.5 parts by mass, trimellitic anhydride 138.5 parts by mass, and dibutylhydroxytoluene 1.4 parts by mass were dissolved. It was.
  • EVONIK isocyanurate modified form of isophorone diisocyanate
  • the acid group-containing (meth) acrylate resin (7) had a solid content acid value of 80 mg KOH / g, an acryloyl group equivalent of 500 g / equivalent, and a weight average molecular weight (Mw) of 4,040.
  • Examples 8 to 14 and Comparative Example 2 A curable resin composition was prepared in the following manner, and various evaluation tests were performed. The results are shown in Table 1.
  • curable resin composition 100 parts by mass of the acid group-containing (meth) acrylate resin (solid content conversion) obtained above, 24 parts by mass of “EPICLON N-680” (cresol novolac type epoxy resin) manufactured by DIC Corporation, A curable resin composition containing 5 parts by mass of “Irgacure 907” [2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one] manufactured by BASF and 13 parts by mass of diethylene glycol monomethyl ether acetate I got a thing.
  • the curable resin composition was apply

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