Classifications

• • 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
  • C08F290/08—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 side groups
  • C08F290/14—Polymers provided for in subclass C08G
• • 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
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
  • H10K59/10—OLED displays
  • H10K59/12—Active-matrix OLED [AMOLED] displays
  • H10K59/122—Pixel-defining structures or layers, e.g. banks

Definitions

• the present invention relates to a novel reactive polycarboxylic acid compound (A), an active energy ray-curable resin composition containing the compound, and a cured product thereof.
• A novel reactive polycarboxylic acid compound
• the present invention relates to a novel reactive polycarboxylic acid compound suitable as a resist material that can also be used as a material for display devices such as organic EL display elements, an active energy ray-curable resin composition containing the compound, and a cured product thereof.
• Organic EL display elements which utilize the electroluminescence of organic compounds, have many features, such as being self-luminous and not dependent on viewing angle, having a fast response speed, and being able to be made thin and lightweight, and are being actively developed for use in image display devices.
• Photolithography pattern formation technology is used to produce components of display devices such as organic EL displays, such as partition walls and planarizing layers, and active energy ray-curable resin compositions are used.
• the present invention aims to provide an active energy ray-curable resin composition that can be patterned by photolithography and has low outgassing, as well as a cured product thereof.
• n represents an average value and is a number from 0 to 10.
• G represents a glycidyl group.
• the active energy ray-curable resin composition containing the reactive polycarboxylic acid compound (A) of the present invention has excellent developability, can be patterned by photolithography, and can provide a cured resin product with low outgassing.
• the reactive polycarboxylic acid compound (A) of the present invention can be obtained by reacting an epoxy resin (a) having a structure represented by the following formula (1) with a carboxylic acid compound (b) having both a polymerizable ethylenically unsaturated group and a carboxy group in one molecule to obtain a reactive epoxy carboxylate compound (c), followed by reaction with a polybasic acid anhydride (d) represented by the following formula (2):
• n represents the average value and is a number between 0 and 10.
• G represents a glycidyl group.
• the epoxy resin (a) used in the present invention is an epoxy resin represented by formula (1) above.
• Epoxy resins represented by formula (1) are generally available under various trade names, including EOCN-102S, EOCN-103S, EOCN-104S, and EOCN-1020 manufactured by Nippon Kayaku Co., Ltd.; Epicron N-660, Epicron N-665, Epicron N-670, Epicron N-673, Epicron N-680, Epicron N-690, Epicron N-695, Epicron N-665-EXP, and Epicron N-672-EXP manufactured by DIC Corporation; and YDCN-700-7, YDCN-700-10, YDCN-704, and YDCN-704A manufactured by Nippon Steel Chemical & Material Co., Ltd.
• a carboxylic acid compound (b) having both a polymerizable ethylenically unsaturated group and a carboxy group in one molecule (hereinafter also referred to simply as “carboxylic acid compound (b)”) is reacted to impart reactivity to actinic rays.
• carboxylic acid compound (b) having both a polymerizable ethylenically unsaturated group and a carboxy group in one molecule
• the total amount of carboxylic acid compound (b) is 90 to 120 equivalent percent per equivalent of epoxy resin (a). This range allows for production under relatively stable conditions. If the amount of carboxylic acid compound charged is greater than this, excess carboxylic acid compound (b) and compound (c) will remain, which is undesirable.
• the amount of catalyst used is 0.1 to 10 parts by mass based on the total amount of reactants, i.e., the epoxy compound (a), the reactive epoxy carboxylate compound (c) obtained from the carboxylic acid compound (b), and the polybasic acid anhydride (d), and optionally solvents and other components.
• the reaction temperature is 60 to 150°C, and the reaction time is preferably 5 to 60 hours.
• catalysts that can be used include triethylamine, benzyldimethylamine, triethylammonium chloride, benzyltrimethylammonium bromide, benzyltrimethylammonium iodide, triphenylphosphine, triphenylstibine, methyltriphenylstibine, chromium octanoate, and zirconium octanoate.
• the reactive compound (B) can be used alone or in a mixed organic solvent.
• the reactive compound (B) when used as a curable resin composition, it can be used directly as a composition, which is preferable.
• This acid addition reaction is completed when the acid value of the reaction product reaches a range of plus or minus 10% of the set acid value, while sampling is performed as needed.
• the preferred molecular weight range of the reactive polycarboxylic acid compound (A) thus obtained is a weight average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography) of 500 to 50,000, more preferably 1,000 to 30,000, and particularly preferably 1,000 to 10,000.
• the toughness of the cured product will not be sufficient, and if it is too large, the viscosity will be too high, making coating difficult.
• Acrylates that can be used include monofunctional (meth)acrylates, polyfunctional (meth)acrylates, as well as epoxy acrylates, polyester acrylates, urethane acrylates, etc.
• Examples of monofunctional (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, lauryl (meth)acrylate, polyethylene glycol (meth)acrylate, polyethylene glycol (meth)acrylate monomethyl ether, phenylethyl (meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, and tetrahydrofurfuryl (meth)acrylate.
• Multifunctional (meth)acrylates include butanediol di(meth)acrylate, hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, nonanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene di(meth)acrylate, polyethylene glycol di(meth)acrylate, tris(meth)acryloyloxyethyl isocyanurate, polypropylene glycol di(meth)acrylate, adipic acid epoxy di(meth)acrylate, bisphenol ethylene oxide di(meth)acrylate, hydrogenated bisphenol ethylene oxide di(meth)acrylate, bisphenol di(meth)acrylate acrylate, di(meth)acrylate of an ⁇ -caprolactone adduct of neopen glycol hydroxypivalate, poly(meth)acrylate of a reaction product of dipentaerythritol and
• Usable vinyl compounds include vinyl ethers, styrenes, and other vinyl compounds.
• vinyl ethers include ethyl vinyl ether, propyl vinyl ether, hydroxyethyl vinyl ether, and ethylene glycol divinyl ether.
• styrenes include styrene, methyl styrene, and ethyl styrene.
• Other vinyl compounds include triallyl isocyanurate and trimethallyl isocyanurate.
• reactive oligomers include urethane acrylates, which have both a functional group sensitive to active energy rays and a urethane bond in the same molecule; polyester acrylates, which similarly have both a functional group sensitive to active energy rays and an ester bond in the same molecule; epoxy acrylates, which are derived from epoxy resins and have both a functional group sensitive to active energy rays in the same molecule; and reactive oligomers in which these bonds are used in combination.
• the cationic reactive monomer is a compound that generally has an epoxy group.
• glycidyl (meth)acrylate methyl glycidyl ether, ethyl glycidyl ether, butyl glycidyl ether, bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (e.g., "Cyracure UVR-6110" manufactured by Union Carbide), 3,4-epoxycyclohexylethyl-3,4-epoxycyclohexanecarboxylate, vinylcyclohexene dioxide (e.g., "ELR-4206” manufactured by Union Carbide), limonene dioxide (e.g., "Celloxide 3000” manufactured by Daicel Chemical Industries, Ltd.), and acetone.
• ERR-4206 manufactured by Union Carbide
• limonene dioxide e.g.
• epoxy groups include 3,4-epoxycyclohexene dioxide, 3,4-epoxy-4-methylcyclohexyl-2-propylene oxide, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-m-dioxane, bis(3,4-epoxycyclohexyl)adipate (such as Union Carbide's "Cyracure UVR-6128"), bis(3,4-epoxycyclohexylmethyl)adipate, bis(3,4-epoxycyclohexyl)ether, bis(3,4-epoxycyclohexylmethyl)ether, and bis(3,4-epoxycyclohexyl)diethylsiloxane.
• 3,4-epoxycyclohexene dioxide 3,4-epoxy-4-methylcyclohexyl-2-propylene oxide
• radical-curing acrylates are most preferred as the reactive compound (B).
• the reactive compound (B) In the case of cationic types, the carboxylic acid and epoxy group react, making it necessary to use a two-part mixture.
• the active energy ray-curable resin composition of the present invention can be obtained by mixing the reactive polycarboxylic acid compound (A) of the present invention with another reactive compound (B). Other components may be added as appropriate depending on the intended use.
• the active energy ray-curable resin composition of the present invention contains 97 to 5 parts by mass, preferably 87 to 10 parts by mass, of a reactive polycarboxylic acid compound (A), and 3 to 95 parts by mass, more preferably 3 to 90 parts by mass, of another reactive compound (B). If necessary, the composition may contain 0 to 80 parts by mass of other components.
• other components can be added to the composition in an amount of up to 70 parts by weight.
• these other components include photopolymerization initiators, other additives, coloring materials, thermosetting catalysts, and volatile solvents added to adjust viscosity for purposes such as coatability.
• the active energy ray-curable resin composition of the present invention may further contain a photopolymerization initiator, preferably a radical photopolymerization initiator or a cationic photopolymerization initiator.
• a photopolymerization initiator preferably a radical photopolymerization initiator or a cationic photopolymerization initiator.
• the radical photopolymerization initiator include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether; acetophenones such as acetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 2-hydroxy-2-methyl-phenylpropan-1-one, diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, and 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-
• examples of cationic photopolymerization initiators include diazonium salts of Lewis acids, iodonium salts of Lewis acids, sulfonium salts of Lewis acids, phosphonium salts of Lewis acids, other halides, triazine-based initiators, borate-based initiators, and other photoacid generators.
• diazonium salts of Lewis acids include p-methoxyphenyldiazonium fluorophosphonate and N,N-diethylaminophenyldiazonium hexafluorophosphonate (e.g., San-Aid SI-60L/SI-80L/SI-100L manufactured by Sanshin Chemical Industry Co., Ltd.).
• iodonium salts of Lewis acids include diphenyliodonium hexafluorophosphonate and diphenyliodonium hexafluoroantimonate.
• sulfonium salts of Lewis acids include triphenylsulfonium hexafluorophosphonate (e.g., Cyracure UVI-6990 manufactured by Union Carbide) and triphenylsulfonium hexafluoroantimonate (e.g., Cyracure UVI-6974 manufactured by Union Carbide).
• phosphonium salts of Lewis acids include triphenylphosphonium hexafluoroantimonate.
• halides include 2,2,2-trichloro-[1-4'-(dimethylethyl)phenyl]ethanone (e.g., Trigonal PI manufactured by AKZO Corporation), 2,2-dichloro-1-4-(phenoxyphenyl)ethanone (e.g., Sandray 1000 manufactured by Sandoz Corporation), and ⁇ , ⁇ , ⁇ -tribromomethylphenyl sulfone (e.g., BMPS manufactured by Seitetsu Kagaku Co., Ltd.).
• 2,2,2-trichloro-[1-4'-(dimethylethyl)phenyl]ethanone e.g., Trigonal PI manufactured by AKZO Corporation
• 2,2-dichloro-1-4-(phenoxyphenyl)ethanone e.g., Sandray 1000 manufactured by Sandoz Corporation
• ⁇ , ⁇ , ⁇ -tribromomethylphenyl sulfone e.g., BMPS manufactured by Seitetsu Kag
• triazine initiators examples include 2,4,6-tris(trichloromethyl)-triazine, 2,4-trichloromethyl-(4'-methoxyphenyl)-6-triazine (e.g., Triazine A manufactured by Panchim Corporation), 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine (e.g., Triazine PMS manufactured by Panchim Corporation), and 2,4-trichloromethyl-(pipronyl)-6-triazine (e.g., Triazine PMS manufactured by Panchim Corporation).
• 2,4,6-tris(trichloromethyl)-triazine examples include 2,4,6-tris(trichloromethyl)-triazine, 2,4-trichloromethyl-(4'-methoxyphenyl)-6-triazine (e.g., Triazine A manufactured by Panchim Corporation), 2,4-trichloromethyl-(4'-
• Triazine PP manufactured by Panchim 2,4-trichloromethyl-(4'-methoxynaphthyl)-6-triazine
• Triazine B manufactured by Panchim, etc. 2,4-trichloromethyl-(4'-methoxynaphthyl)-6-triazine
• 2[2'(5-methylfuryl)ethylidene]-4,6-bis(trichloromethyl)-s-triazine manufactured by Sanwa Chemical Co., Ltd., etc.
• 2(2'-furylethylidene)-4,6-bis(trichloromethyl)-s-triazine manufactured by Sanwa Chemical Co., Ltd.
• Borate-based photopolymerization initiators include NK-3876 and NK-3881 manufactured by Nippon Kanko Dyes Co., Ltd.
• Other photoacid generators include 9-phenylacridine, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2-biimidazole (e.g., Biimidazole manufactured by Kurogane Chemical Co., Ltd.), 2,2-azobis(2-amino-propane) dihydrochloride (e.g., V50 manufactured by Wako Pure Chemical Industries, Ltd.), 2,2-azobis[2-(imidazolin-2yl)propane]dihydrochloride, Examples include [eta-5-2-4-(cyclopentadecyl)(1,2,3,4,5,6,eta)-(methylethyl)-benzene]iron(II) hexafluorophosphonate (e.g., Irgacur
• azo-based initiators such as azobisisobutyronitrile
• heat-sensitive peroxide-based radical initiators such as benzoyl peroxide
• radical and cationic photopolymerization initiators may be used in combination.
• One type of photopolymerization initiator can be used alone, or two or more types can be used in combination.
• radical photopolymerization initiators are particularly preferred, taking into consideration the properties of the reactive polycarboxylic acid compound (A) of the present invention.
• the active energy ray-curable resin composition of the present invention may contain a coloring pigment.
• coloring pigments that can be used include extender pigments that are not intended for coloring purposes. Examples include talc, barium sulfate, calcium carbonate, magnesium carbonate, barium titanate, aluminum hydroxide, silica, clay, and carbon black.
• the active energy ray-curable resin composition of the present invention may contain other additives as needed.
• additives include thermosetting catalysts such as melamine, thixotropy-imparting agents such as Aerosil, silicone-based and fluorine-based leveling agents and defoamers, polymerization inhibitors such as hydroquinone and hydroquinone monomethyl ether, stabilizers, and antioxidants.
• resins that do not react with active energy rays can also be used, such as other epoxy resins, phenolic resins, urethane resins, polyester resins, ketone-formaldehyde resins, cresol resins, xylene resins, diallyl phthalate resins, styrene resins, guanamine resins, natural and synthetic rubbers, acrylic resins, polyolefin resins, and modified versions of these. These are preferably used in amounts up to 40 parts by mass in the resin composition.
• a volatile solvent can be added to the resin composition in an amount of up to 50 parts by weight, and more preferably up to 35 parts by weight, to adjust the viscosity.
• the active energy ray-curable resin composition of the present invention is easily cured by active energy rays.
• active energy rays include electromagnetic waves such as ultraviolet rays, visible light, infrared rays, X-rays, gamma rays, and laser beams, and particle beams such as alpha rays, beta rays, and electron beams.
• ultraviolet rays, laser beams, visible light, and electron beams are preferred.
• the display device material is a material used in display elements such as liquid crystal display devices, organic EL devices, and electronic paper. Specific applications include spacers, protective films, planarizing films, interlayer insulating films, and partition materials. Of these, the display device according to one embodiment of the present invention is preferably an organic EL device.
• the present invention also includes a cured product obtained by irradiating the above-mentioned curable resin composition with active energy rays, and also includes a multilayer material having a layer of the cured product.
• the unreacted reactive polycarboxylic acid compound (A) as an alkaline water-developable resist material composition, taking advantage of its characteristic of being soluble in alkaline aqueous solutions.
• the active energy ray-curable resin composition which is the resist material composition of the present invention, can be used with a variety of materials that can be patterned. For example, it is particularly useful as a solder resist material and an interlayer insulating material for build-up construction methods. It can also be used as an optical waveguide in electrical, electronic, and optical substrates such as printed wiring boards, optoelectronic boards, and optical boards.
• Particularly suitable applications include photosensitive films, photosensitive films with supports, insulating resin sheets such as prepregs, circuit boards (for laminates, multilayer printed wiring boards, etc.), solder resists, underfill materials, die bonding materials, semiconductor encapsulants, hole filling resins, component embedding resins, color resists, color filters, black matrices, and a wide range of other applications requiring resin compositions.
• insulating resin sheets such as prepregs, circuit boards (for laminates, multilayer printed wiring boards, etc.), solder resists, underfill materials, die bonding materials, semiconductor encapsulants, hole filling resins, component embedding resins, color resists, color filters, black matrices, and a wide range of other applications requiring resin compositions.
• the resin composition can be suitably used in resin compositions for insulating layers of multilayer printed wiring boards (multilayer printed wiring boards in which the insulating layer is a cured product of a photosensitive resin composition), resin compositions for interlayer insulating layers (multilayer printed wiring boards in which the interlayer insulating layer is a cured product of a photosensitive resin composition), and resin compositions for plating (multilayer printed wiring boards in which plating is formed on a cured product of a photosensitive resin composition).
• Patterning using the active energy ray-curable resin composition of the present invention can be carried out, for example, as follows:
• a coating film can be formed by applying the curable resin composition of the present invention to a substrate in a film thickness of 0.1 to 200 ⁇ m by a method such as screen printing, spraying, roll coating, electrostatic coating, curtain coating, or spin coating, and drying the coating film at a temperature of typically 50 to 110°C, preferably 60 to 100°C.
• the coating film is irradiated directly or indirectly with high-energy rays such as ultraviolet rays through a photomask having an exposure pattern formed thereon, typically at an intensity of about 10 to 2000 mJ/ cm2 , and the desired pattern can be obtained using a developer described below, for example, by spraying, vibration immersion, paddle coating, brushing, or the like.
• high-energy rays such as ultraviolet rays
• a photomask having an exposure pattern formed thereon, typically at an intensity of about 10 to 2000 mJ/ cm2
• the desired pattern can be obtained using a developer described below, for example, by spraying, vibration immersion, paddle coating, brushing, or the like.
• the alkaline aqueous solution used for the above development can be an inorganic alkaline aqueous solution such as potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium phosphate, or potassium phosphate, or an organic alkaline aqueous solution such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, monoethanolamine, diethanolamine, or triethanolamine.
• This aqueous solution can further contain an organic solvent, buffer, complexing agent, dye, or pigment.
• the reactive polycarboxylic acid compound (A) of the present invention can exhibit good developability despite having a relatively high molecular weight.
• any of a variety of coating methods can be used, including gravure and other intaglio printing methods, flexographic and other relief printing methods, silkscreen and other stencil printing methods, offset and other planographic printing methods, and methods using a roll coater, knife coater, die coater, curtain coater, spin coater, etc.
• the cured product of the active energy ray-curable resin composition of the present invention refers to the product obtained by irradiating the active energy ray-curable resin composition of the present invention with active energy rays and curing it.
• Synthesis Example 1 Synthesis of reactive epoxy carboxylate compound (c) 218 g of cresol novolac epoxy resin EOCN-104S (manufactured by Nippon Kayaku Co., Ltd., softening point 92°C, epoxy equivalent 218 g/eq.) and 72.0 g of acrylic acid (AA) as carboxylic acid compound (b) were added. 1.25 g of triphenylphosphine as a catalyst and propylene glycol monomethyl ether monoacetate as a solvent were added so that the solid content was 70 mass%, and the mixture was reacted at 100°C for 24 hours to obtain a reactive epoxy carboxylate compound (c) solution.
• Example 1-1 Preparation of reactive polycarboxylic acid compound (A-1) To 50.0 g of the reactive epoxy carboxylate compound (c) solution obtained in Synthesis Example 1, 2.61 g of maleic anhydride as the polybasic acid anhydride (d) and propylene glycol monomethyl ether monoacetate as a solvent were added so that the solid content was 50%, and an acid addition reaction was carried out at 100°C to obtain a reactive polycarboxylic acid compound (A-1) solution with a solid acid value of 38.0 mg KOH/g. The solid acid value (mg KOH/g) was measured as a solution and converted to a value based on the solid content.
• Example 1-2 Preparation of reactive polycarboxylic acid compound (A-2) To 50.0 g of the reactive epoxy carboxylate compound (c) solution obtained in Synthesis Example 1, 4.08 g of maleic anhydride as the polybasic acid anhydride (d) and propylene glycol monomethyl ether monoacetate as a solvent were added so that the solid content was 50%, and an acid addition reaction was carried out at 100°C to obtain a reactive polycarboxylic acid compound (A-2) solution with a solid acid value of 60.0 mg KOH/g. The solid acid value (mg KOH/g) was measured as a solution and converted to a value based on the solid content.
• Example 1-3 Preparation of reactive polycarboxylic acid compound (A-3) To 50.0 g of the reactive epoxy carboxylate compound (c) solution obtained in Synthesis Example 1, 7.19 g of maleic anhydride as the polybasic acid anhydride (d) and propylene glycol monomethyl ether monoacetate as a solvent were added so that the solid content was 50%, and an acid addition reaction was carried out at 100°C to obtain a reactive polycarboxylic acid compound (A-3) solution with a solid acid value of 98.0 mg KOH/g. The solid acid value (mg KOH/g) was measured as a solution and converted to a value based on the solid content.
• Example 3 and Comparative Example 3 Preparation of resin composition and evaluation of developability, evaluation of outgassing amount 2.00 g of the reactive polycarboxylic acid compound (A) obtained in Examples 1-1 to 1-3 and Comparative Example 1-1, 0.67 g of DPHA (trade name: dipentaerythritol hexaacrylate manufactured by Nippon Kayaku Co., Ltd.) as another reactive compound (B), 0.08 g of Irgacure 184 (manufactured by BASF) as a photopolymerization initiator, and 1.63 g of propylene glycol monomethyl ether monoacetate as a concentration adjusting solvent were added and dispersed uniformly to obtain a resin composition.
• DPHA trade name: dipentaerythritol hexaacrylate manufactured by Nippon Kayaku Co., Ltd.
• Irgacure 184 manufactured by BASF
• Outgassing amount evaluation (abbreviation in the table: outgassing)
• the photosensitive resin composition was applied to rolled copper foil BHY-82F-HA-V2 (manufactured by JX Nippon Mining & Metals Corporation) with an applicator to a thickness of 10 ⁇ m, and the coating was dried in a hot air dryer at 80°C for 30 minutes, after which it was irradiated with ultraviolet light at 500 mJ/ cm2 using an ultraviolet irradiator (manufactured by GS YUASA: CS 30L-1).
• the copper foil was then removed with iron(III) chloride 45° Baume (manufactured by Junsei Chemical Co., Ltd.) to obtain a cured product.
• Thermal desorption GC-MS revealed that polybasic acid anhydride (d) was generated as outgassing from reactive polycarboxylic acid compound (A).
• the peak area of the peak assigned to polybasic acid anhydride (d) was determined using P&T-GC and used as an index of the amount of outgassing (Area/mg).
• the effective carbon number was calculated from the type and number of functional groups in Table 2, which was compiled based on the following reference: (Reference: Yoshio Umezawa, Tsuguro Sawada, Hiroshi Nakamura, eds.; “Latest Separation, Purification, and Detection Methods,” NTS (1997), p. 35).
• the active energy ray-curable resin composition using the reactive polycarboxylic acid compound (A) of the present invention has a smaller amount of outgassing per acid value and is also excellent in developability, compared to the comparative resin composition.

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