Resins having acidic groups and polymerizable unsaturated groups, curable resin compositions, cured products, insulating materials, and resist members.

Abstract

To provide a resin capable of giving a cured product high in adhesion and excellent in low elastic modulus and low dielectric characteristics.SOLUTION: The resin having an acid group and a polymerizable unsaturated group uses an epoxy resin (A), an unsaturated monobasic acid (B), and a polybasic acid anhydride (C) as essential raw materials. It is preferable that the epoxy resin (A) is obtained by reacting a reaction product of 1.5-8 moles of an aromatic vinyl compound based on 1 mole of dihydroxybiphenyl with epihalohydrin.SELECTED DRAWING: None

Description

[Technical Field] 【0001】 The present invention relates to a resin having acidic groups and polymerizable unsaturated groups, a curable resin composition, a cured product, an insulating material, and a resist member. [Background technology] 【0002】 Traditionally, solder resist has been widely used as a material to prevent solder from adhering to areas other than the mounting area when soldering electronic components onto printed circuit boards, and to form a coating that semi-permanently prevents oxidation and corrosion of the wiring. One technique for forming such solder resist patterns is the photoresist method, which can accurately form fine patterns. Among these, the alkali-developable liquid photoresist method has become the mainstream, particularly due to environmental considerations. 【0003】 Furthermore, in order to achieve higher density, printed circuit boards are constantly becoming smaller, more multilayered, and single-board, and the mounting method is also shifting towards surface mount technology (SMT). As a result, there is an increasing demand for solder resist films to be finer, have high Tg (high heat resistance), high resolution, high precision, and high reliability. In addition, to achieve high reliability, solder resist films must also have excellent adhesion to adjacent materials (copper foil, etc.), low elastic modulus (internal stress relaxation), and low dielectric properties (low dielectric constant, low dielectric loss tangent). 【0004】 Conventionally, as an alkali-soluble photosensitive resin used in alkali-developable liquid photoresist methods, a reaction product (acid pendant type epoxy acrylate) obtained by reacting a novolac-type epoxy resin with an unsaturated monocarboxylic acid and further adding a polybasic acid anhydride has been widely used (see, for example, Patent Document 1). 【0005】 Furthermore, as an epoxy resin usable in the aforementioned photoresist method, Patent Document 2 discloses an epoxy resin obtained by condensing dihydroxynaphthalene and epihalohydrin. Furthermore, as epoxy compounds that serve as raw materials for the epoxy resin, Patent Document 3 describes an alkoxysilyl epoxy compound having at least one alkoxysilyl group and at least two epoxy groups, Patent Document 4 describes a monoallyl monoglycidyl ether compound having a biphenyl skeleton, and Patent Document 5 describes an epoxy-substituted isocyanurate obtained by epoxidizing an olefin-substituted isocyanurate. [Prior art documents] [Patent Documents] 【0006】 [Patent Document 1] Special Publication No. 1-54390 [Patent Document 2] Patent No. 3062822 [Patent Document 3] Special Publication No. 2014-531473 [Patent Document 4] International Publication No. 2011 / 078060 [Patent Document 5] Japanese Patent Publication No. 2012-25688 [Overview of the Initiative] [Problems that the invention aims to solve] 【0007】 However, conventional epoxy resins described in the above-mentioned patent documents, etc., and cured products made from curable resin compositions containing reaction products of epoxy resin, unsaturated monocarboxylic acid, and polybasic acid anhydride, are inferior in terms of adhesion to adjacent members (such as copper foil), low elastic modulus (internal stress relaxation), and low dielectric properties (low dielectric constant, low dielectric loss tangent), and there is room for improvement. 【0008】 Therefore, the object of the present invention is to solve the problems of the above-mentioned prior art and to provide a resin that can produce a cured product with high adhesion, low elastic modulus, and excellent low dielectric properties, and a curable resin composition containing such a resin. Furthermore, a further objective of the present invention is to provide a cured product, an insulating material, and a resist member that exhibit high adhesion, low elastic modulus, and excellent low dielectric properties. [Means for solving the problem] 【0009】 As a result of diligent research to solve the above problems, the present inventors have found that by incorporating a resin having acidic groups and polymerizable unsaturated groups, obtained by reacting an epoxy resin (A) having a specific structure with an unsaturated monobasic acid (B) and a polybasic acid anhydride (C), into a curable resin composition, the adhesion, low modulus of elasticity, and low dielectric properties of the cured product obtained by curing such a curable resin composition are improved, leading to the completion of the present invention. In other words, the gist of the present invention that solves the above problems is as follows. 【0010】 [1] A resin having acidic groups and polymerizable unsaturated groups, wherein epoxy resin (A), unsaturated monobasic acid (B), and polybasic acid anhydride (C) are essential raw materials. The epoxy resin (A) is obtained by reacting 1 mole of dihydroxybiphenyl with 1.5 to 8 moles of an aromatic vinyl compound and an epihalohydrin, and is a resin having acidic groups and polymerizable unsaturated groups, represented by the following general formula (1). 【0011】 [ka] (However, in the general formula (1) above, R1 and R2 each independently represent hydrogen or an α-methylbenzyl group, and G represents a glycidyl group. p and q each independently represent a number from 0 to 4, and p+q has an average value of 1.5 to 8. Also, n represents a number from 0 to 5.) 【0012】 [2] A curable resin composition characterized by comprising the resin having the acid group and polymerizable unsaturated group described in [1] above. 【0013】 [3] The curable resin composition according to [1] or [2], further comprising a photopolymerization initiator. 【0014】 [4] The curable resin composition according to any one of [1] to [3], further comprising a resin (D) having acid groups and polymerizable unsaturated groups other than the resin having acid groups and polymerizable unsaturated groups. 【0015】 [5] A curable resin composition according to any one of [1] to [4], further comprising a curing agent. 【0016】 [6] A cured product characterized by being obtained by curing any one of the curable resin compositions described in [2] to [5] above. 【0017】 [7] An insulating material characterized by comprising any one of the curable resin compositions described in [2] to [5] above. 【0018】 [8] A resist member characterized by comprising the curable resin composition described in any one of [2] to [5] above. [Effects of the Invention] 【0019】 According to the present invention, it is possible to provide a resin having acid groups and polymerizable unsaturated groups that can produce a cured product with high adhesion, low elastic modulus, and excellent low dielectric properties, and a curable resin composition containing such a resin having acid groups and polymerizable unsaturated groups. Furthermore, according to the present invention, it is possible to provide cured products, insulating materials, and resist members that have high adhesion, low elastic modulus, and excellent low dielectric properties. [Modes for carrying out the invention] 【0020】 The resin, curable resin composition, cured product, insulating material, and resist member having acidic groups and polymerizable unsaturated groups of the present invention will be described in detail below based on embodiments thereof. 【0021】 (Explanation of terms) Unless otherwise specified in this specification, the following definitions of terms apply. 【0022】 In this specification, examples of "aryl group" include phenyl group, naphthyl group, phenalenyl group, phenantrenyl group, anthryl group, azulenyl group, indenyl group, indanyl group, tetralinyl group, and the like. Furthermore, the hydrogen atoms of the aromatic ring in the "aryl group" may be substituted with, for example, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a halogen atom. 【0023】 In this specification, "aralkyl group" refers to, for example, a benzyl group, a diphenylmethyl group, a biphenyl group, a naphthylmethyl group, and the like. 【0024】 In this specification, "alkyl group" refers to, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an isohexyl group, an (n-)heptyl group, an (n-)octyl group, an (n-)nonyl group, an (n-)decyl group, an (n-)undecyl group, an (n-)dodecyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, or a cyclononyl group. 【0025】 In this specification, examples of "alkoxy group (alkyloxy group)" include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, pentyloxy group, hexyloxy group, 2-ethylhexyloxy group, octyloxy group, nonyloxy group, and the like. 【0026】 In this specification, "halogen atoms" include, for example, fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, and the like. 【0027】 In this specification, examples of "alkylene group" include methylene group, ethylene group, propylene group, 1-methylmethylene group, 1,1-dimethylmethylene group, 1-methylethylene group, 1,1-dimethylethylene group, 1,2-dimethylethylene group, propylene group, butylene group, 1-methylpropylene group, 2-methylpropylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, undecylene group, dodecylene group, and the like. 【0028】 In this specification, "monovalent hydrocarbon group" refers, for example, to the alkyl group described above, and one or more -CH2- in the alkyl group may be substituted with -O- or -S- so as not to be adjacent to each other, or one or more -CH2-CH2- in the alkyl group may be substituted with -CH=CH- so as not to be adjacent to each other. 【0029】 In this specification, "divalent hydrocarbon group" refers, for example, to the alkylene group described above. In the alkylene group, one or more -CH2- groups may be substituted with -O- or -S- groups such that they are not adjacent to each other, or one or more -CH2-CH2- groups may be substituted with -CH=CH- groups such that they are not adjacent to each other. 【0030】 In this specification, "(meth)acrylate" means acrylate and / or methacrylate. In this specification, "(meth)acryloyl" means acryloyl and / or methacryloyl. Furthermore, in this specification, "(meth)acrylic" means acrylic and / or methacrylic. 【0031】 <Resin having acidic groups and polymerizable unsaturated groups> The resin having acidic groups and polymerizable unsaturated groups in this embodiment is characterized by using an epoxy resin (A) having a specific structure, an unsaturated monobasic acid (B), and a polybasic acid anhydride (C) as essential raw materials. In other words, the resin having acidic groups and polymerizable unsaturated groups in this embodiment is a reaction product of an epoxy resin (A) having a specific structure, an unsaturated monobasic acid (B), and a polybasic acid anhydride (C). When the resin having acidic groups and polymerizable unsaturated groups of this embodiment is blended into a curable resin composition, and the cured product obtained by curing the curable resin composition has high adhesion, low elastic modulus, and excellent low dielectric properties. 【0032】 Examples of acid groups in the resin having the aforementioned acid group and polymerizable unsaturated group include carboxyl groups, sulfonic acid groups, and phosphoric acid groups. Among these, carboxyl groups are preferred as acid groups because they exhibit excellent alkali developability. 【0033】 Examples of polymerizable unsaturated groups in the resin having the acid group and polymerizable unsaturated group include (meth)acryloyl group, allyl group, isopropenyl group, 1-propenyl group, styryl group, styrylmethyl group, maleimide group, vinyl ether group, and the like. 【0034】 (Epoxy resin (A)) The present invention provides an epoxy resin as an essential raw material, which is obtained by reacting 1 mole of dihydroxybiphenyl with 1.5 to 8 moles of an aromatic vinyl compound and an epihalohydrin, and is characterized by being represented by the following general formula (1). 【0035】 [ka] However, in the general formula (1) above, R1 and R2 each independently represent hydrogen or an α-methylbenzyl group, and G represents a glycidyl group. p and q each independently represent a number from 0 to 4, and p+q has an average value of 1.5 to 8. Also, n represents a number from 0 to 5. A cured product using a resin having acidic groups and polymerizable unsaturated groups, with the aforementioned epoxy resin (A) as an essential raw material, exhibits high adhesion, low elastic modulus (internal stress relaxation), and low dielectric properties (low dielectric constant, low dielectric loss tangent), making it extremely useful in the fields of insulating materials and resist components. 【0036】 The epoxy resin (A) is represented by the above general formula (1). Here, R1 and R2 in the above general formula (1) are substituents that independently represent hydrogen or an α-methylbenzyl group. Furthermore, from the viewpoint of low hygroscopicity and low dielectric properties, substituents of an α-methylbenzyl group are preferred. Note that in the above general formula (1), R1 and R2 may be the same or different, and even if there are multiple R1 or R2, they may be the same or different. 【0037】 In the general formula (1) above, p and q each independently represent numbers from 0 to 4, and p+q has an average value of 1.5 to 8. Furthermore, it is preferable that p and q each independently represent numbers from 1.5 to 7, and more preferably from 1.8 to 6. When p and q are within the above range, a good balance of reactivity, high adhesion, low modulus of elasticity, and low dielectric properties is obtained, which is preferable. 【0038】 In the above general formula (1), n ​​represents a number between 0 and 5, preferably between 0 and 4 as the average value (number mean), and more preferably between 0 and 3. When n is within the above range, it is preferable because it has low viscosity and excellent moldability. 【0039】 Epoxy resin (A) is obtained by reacting 1 mole of dihydroxybiphenyl with 1.5 to 8 moles of an aromatic vinyl compound as an intermediate (precursor). The epoxy resin can then be produced by reacting the reaction product with an epihalohydrin. Furthermore, the substituents represented by α-methylbenzyl groups, R1 and R2 in the above general formula (1), are groups derived from aromatic vinyl compounds (e.g., styrene). As the epihalohydrin, it is preferable to use a compound selected from epichlorohydrin, epifluorohydrin, epibromohydrin, epiiodohydrin, or a mixture thereof, with epichlorohydrin being preferred. 【0040】 The reactant that serves as an intermediate (precursor) to epoxy resin (A) is preferably represented by the following general formula (2). In the following general formula (2), R1, R2, p, and q are the same as R1, R2, p, and q in the above general formula (1). 【0041】 [ka] 【0042】 The reactant represented by the general formula (2) above may consist mainly of a single compound, or it may be a mixture of components in which R1 and R2 are different, as well as p and q are different. 【0043】 The aforementioned reaction product can be produced by reacting dihydroxybiphenyl with an aromatic vinyl compound. The amount of aromatic vinyl compound reacted with 1 mole of dihydroxybiphenyl is in the range of 1.5 to 8 moles, preferably 1.5 to 7 moles, and more preferably 1.8 to 6 moles. By reacting at the aforementioned mixing ratio, compared to cases where the amount of aromatic vinyl compound reacted is below the aforementioned range, the cured product obtained using the epoxy resin containing the aforementioned reaction product can have an extended crosslinking distance, a lower thermal modulus, and is useful for internal stress relaxation. Furthermore, while normally extending the crosslinking distance reduces the crosslinking density, which tends to lower the glass transition temperature (Tg) and reduce heat resistance, in the present invention, a high Tg (high heat resistance) can be maintained, exhibiting effects that were previously unpredictable and are therefore useful. 【0044】 On the other hand, the amount of reactant used when reacting dihydroxybiphenyl with an aromatic vinyl compound roughly corresponds to the desired number of substituted moles (the number of moles of substituents per mole of dihydroxybiphenyl), so the amount to be used should be determined accordingly. It is also possible to use reaction conditions in which one of the reactants remains unreacted, but even in this case, the amount of aromatic vinyl compound used per mole of dihydroxybiphenyl should be in the range of 1.5 to 8 moles. If one of the reactants remains unreacted, it is desirable to separate it, but if it is a small amount, it is acceptable to leave it as is. Furthermore, if more than 8 moles of aromatic vinyl compound are used, unreacted aromatic vinyl compound may remain, or polymers of aromatic vinyl compound may be formed, which can reduce the heat resistance and flame retardancy of the epoxy resin. 【0045】 Examples of the dihydroxybiphenyls that can be used include 4,4'-dihydroxybiphenyl, 2,2'-dihydroxybiphenyl, and 2,4'-dihydroxybiphenyl, and 4,4'-dihydroxybiphenyl is preferred from the viewpoint of having excellent heat resistance. 【0046】 Examples of the aromatic vinyl compound include styrene, styrene derivatives (p-dimethylsilylstyrene, p-vinylphenylmethyl sulfide, p-hexynylstyrene, p-methoxystyrene, pt-butyldimethylsiloxystyrene, o-methylstyrene, p-methylstyrene, pt-butylstyrene, α-methylstyrene, etc.), vinylnaphthalene, vinylanthracene, 1,1-diphenylethylene, etc., and from the viewpoint of excellent internal stress relaxation properties (low modulus of elasticity at high temperatures), styrene and α-methylstyrene are preferred, with styrene being more preferred. 【0047】 As for the aromatic vinyl compound, the styrene content is preferably 60% by mass or more, and more preferably 80% by mass or more. A styrene content of 60% by mass or more is preferable because it improves heat resistance and internal stress relaxation (low modulus of elasticity at high temperatures). 【0048】 Furthermore, it is hypothesized that using an aromatic vinyl compound with a bulky structure, such as α-methylstyrene, increases molecular rigidity, suppresses molecular motion, and allows for a greater improvement in the glass transition temperature (Tg). 【0049】 The reaction between the dihydroxybiphenyl and the aromatic vinyl compound can be carried out using a reaction method that includes an acid catalyst. This reaction yields the reaction product in which the benzene ring of the dihydroxybiphenyl is substituted with the substituent (such as an α-methylbenzyl group). After the reaction between the dihydroxybiphenyl and the aromatic vinyl compound is complete, the catalyst or unreacted components can be removed as needed, and the next epoxidation reaction can be carried out. However, if the epoxidation reaction is not inhibited, it is not necessary to remove unreacted components or neutralizable components such as acid catalysts. Furthermore, if these components are removed in the purification process such as washing or distillation performed after the epoxidation reaction, or if they are acceptable to be included in the epoxy resin, they are not required to be removed. Examples of the acid catalysts include inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid; organic acids such as methanesulfonic acid, p-toluenesulfonic acid, and oxalic acid; and Lewis acids such as boron trifluoride, anhydrous aluminum chloride, and zinc chloride. Solid acid catalysts having strong acids such as sulfonyl groups can also be used. These acid catalysts can be used individually or in combination of two or more types. 【0050】 The epoxy resin of the present invention is obtained by first obtaining the reactant represented by the above general formula (2) as an intermediate (precursor), and then reacting the reactant with an epihalohydrin. 【0051】 In the reaction between the reactant and the epihalohydrin, it is preferable to add 0.8 to 1.5 equivalents of an alkali metal hydroxide, such as sodium hydroxide or potassium hydroxide, per equivalent of hydroxyl groups in the reactant, and more preferably 0.85 to 1.2 equivalents. Within this range, the amount of residual hydrolyzable chlorine can be reduced, which is preferable. The alkali metal hydroxide can be used in aqueous solution, alcohol solution, or solid state. 【0052】 In the above reaction, it is preferable to use an excess amount of epihalohydrin relative to the reactant. Typically, 1.5 to 15 equivalents of epihalohydrin are used per equivalent of hydroxyl groups in the reactant, but preferably in the range of 1.5 to 8 equivalents. Within this range, production efficiency can be increased, the formation of high molecular weight epoxy resins can be suppressed, viscosity increases can be suppressed, and workability can be improved. 【0053】 The reaction temperature is preferably 120°C or lower, more preferably 100°C or lower, and even more preferably 85°C or lower, as this allows for a reduction in the amount of hydrolyzable chlorine and enables higher purity. 【0054】 During the reaction, polar solvents such as quaternary ammonium salts, dimethyl sulfoxides, or diglyme may be used. Examples of quaternary ammonium salts include tetramethylammonium chloride, tetrabutylammonium chloride, and benzyltriethylammonium chloride, and the amount added is preferably in the range of 0.1 to 2% by mass relative to the reactant. Within this range, the effect of adding the quaternary ammonium salt is sufficiently obtained, the generation of hydrolyzable chlorine can be suppressed, and high purity can be achieved. Furthermore, the amount added of the polar solvent is preferably in the range of 10 to 200% by mass relative to the reactant. Within this range, the effect of the addition is sufficiently obtained without reducing volume efficiency, and it is economically preferable. 【0055】 After the reaction is complete, excess epihalohydrin and solvent are removed by distillation, the residue is dissolved in a solvent such as toluene or methyl isobutyl ketone, filtered, washed with water to remove inorganic salts and residual solvent, and then the solvent is removed by distillation to obtain an epoxy resin. 【0056】 Furthermore, the resulting epoxy resin is further subjected to a re-cyclization reaction by adding 1 to 30 times the amount of alkali metal hydroxide, such as sodium hydroxide or potassium hydroxide, relative to the remaining hydrolyzable chlorine. The reaction temperature at this time is usually 100°C or lower, preferably 90°C or lower. 【0057】 The epoxy equivalent of the epoxy resin is preferably 200 to 600 g / equivalent, more preferably 220 to 500 g / equivalent, and even more preferably 240 to 400 g / equivalent. When the epoxy equivalent of the epoxy resin is within the above range, the generation of secondary hydroxyl groups generated when the epoxy resin reacts with the curing agent is suppressed, and the heat resistance, low moisture absorption, low dielectric properties (especially low dielectric tangent), and reflow resistance due to adhesion properties, etc. of the obtained cured product are also excellent, so it is preferable. The measurement of the epoxy equivalent here is based on JIS K7236. 【0058】 The melt viscosity of the epoxy resin is preferably 10 dPa·s or less, more preferably 0.01 to 5 dPa·s, and even more preferably 0.05 to 3 dPa·s. When the melt viscosity of the epoxy resin is within the above range, it is preferable because it has low viscosity, excellent fluidity and workability, and thus the moldability of the obtained cured product is also excellent. The melt viscosity here is measured with an ICI viscometer in accordance with ASTM D4287. 【0059】 The softening point of the epoxy resin is preferably 30 to 200 °C, more preferably 50 to 150 °C. When the softening point of the epoxy resin is within the above range, it is preferable because it has excellent moldability. The softening point here is measured based on JIS K7234 (ring and ball method). 【0060】 The epoxy resin (A) preferably contains an epoxy resin represented by the above general formula (1) and is an epoxy resin having the epoxy resin as the main component (50% by mass or more). Similarly, the reactant serving as an intermediate of the epoxy resin of the present invention preferably contains the reactant represented by the above general formula (2) and has the reactant as the main component (50% by mass or more). 【0061】 (Unsaturated monobasic acid (B)) The unsaturated monobasic acid (B) is one of the essential raw materials for the resin having the acid group and the polymerizable unsaturated group. The unsaturated monobasic acid (B) is preferably a compound having both an acid group and a polymerizable unsaturated group in one molecule. Examples of the acid group include a carboxyl group, a sulfonic acid group, a phosphoric acid group, and the like. Examples of the polymerizable unsaturated group include a (meth)acryloyl group, an allyl group, an isopropenyl group, a 1-propenyl group, and the like. 【0062】 Examples of the unsaturated monobasic acid (B) include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, α-cyanocinnamic acid, β-styrylacrylic acid, and β-furfurylacrylic acid. Esters, acid halides, and acid anhydrides of the unsaturated monobasic acid can also be used. These unsaturated monobasic acids (B) can be used individually or in combination of two or more. Among these, acrylic acid and methacrylic acid are preferred because they yield a resin having acid groups and polymerizable unsaturated groups that can form a cured product with excellent alkali developability, heat resistance, adhesion, and elongation. The unsaturated monobasic acid (B) is defined by the following general formula (3): 【0063】 [ka] [In the above general formula (3), X 31 X represents an alkylene chain, polyoxyalkylene chain, (poly)ester chain, aromatic hydrocarbon chain, or (poly)carbonate chain having 1 to 10 carbon atoms. 31 The hydrogen atoms in the structure may be substituted with halogen atoms or alkoxy groups, Y 31 This is a hydrogen atom or a methyl group. Compounds represented by [ ] can also be used. 【0064】 Examples of the polyoxyalkylene chains include polyoxyethylene chains and polyoxypropylene chains. 【0065】 Examples of the (poly)ester chain include the following general formula (3-1): 【0066】 [ka] [In the above general formula (3-1), R 311 and R 312 This represents an alkylene group with 1 to 10 carbon atoms, n 311 represents an integer from 1 to 5. Examples include (poly)ester chains represented by ]. 【0067】 Examples of the aromatic hydrocarbon chains include phenylene chains, naphthylene chains, biphenylene chains, phenylnaphthylene chains, or binaphthylene chains. Hydrocarbon chains having aromatic rings such as benzene rings, naphthalene rings, anthracene rings, and phenanthrene rings as partial structures can also be used. 【0068】 The (poly)carbonate chain mentioned above is, for example, the following general formula (3-2): 【0069】 [ka] [In the above general formula (3-2), R 321 This represents an alkylene group with 1 to 10 carbon atoms, n 321 represents an integer from 1 to 5. An example is a (poly)carbonate chain represented by ]. 【0070】 The molecular weight of the compound represented by the above general formula (3) is preferably in the range of 100 to 500, and more preferably in the range of 150 to 400. 【0071】 (Polybasic acid anhydride (C)) The polybasic acid anhydride (C) is one of the essential raw materials for the resin having the acid group and polymerizable unsaturated group. Examples of the polybasic acid anhydride (C) include aliphatic polybasic acid anhydride, alicyclic polybasic acid anhydride, aromatic polybasic acid anhydride, acid halogen of aliphatic polybasic acid anhydride, acid halogen of alicyclic polybasic acid anhydride, and acid halogen of aromatic polybasic acid anhydride. 【0072】 Examples of the aliphatic polybasic acid anhydride include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, citraconic acid, itaconic acid, glutaconic acid, and acid anhydrides of 1,2,3,4-butanetetracarboxylic acid. Furthermore, the aliphatic polybasic acid anhydride may have either linear or branched aliphatic hydrocarbon groups, and may also have unsaturated bonds in its structure. 【0073】 In this invention, the alicyclic polybasic acid anhydride is defined as one in which the acid anhydride group is bonded to an alicyclic structure, and the presence or absence of aromatic rings in other structural parts is irrelevant. Examples of the alicyclic polybasic acid anhydride include 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, and acid anhydrides of 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic acid. 【0074】 Examples of the aforementioned aromatic polybasic acid anhydrides include phthalic acid, trimellitic acid, pyromellitic acid, naphthalenedicarboxylic acid, naphthalentricarboxylic acid, naphthalenetetracarboxylic acid, biphenyldicarboxylic acid, biphenyltricarboxylic acid, biphenyltetracarboxylic acid, and benzophenonetetracarboxylic acid. 【0075】 The polybasic acid anhydride (C) may be used alone or in combination of two or more. Among these, tetrahydrophthalic anhydride, succinic anhydride, and cyclohexanedicarboxylic acid anhydride are preferred from the viewpoint of more effectively improving photosensitivity, developability, adhesion, low modulus of elasticity, and low dielectric properties. 【0076】 (Method for producing resins having acidic groups and polymerizable unsaturated groups) The method for producing the resin having acidic groups and polymerizable unsaturated groups in this embodiment is not particularly limited and may be produced by any method. In producing the resin having acidic groups and polymerizable unsaturated groups, the process may be carried out in an organic solvent as needed, and a basic catalyst may also be used as needed. 【0077】 The method for producing the resin having the acidic group and polymerizable unsaturated group is not particularly limited, as long as it uses epoxy resin (A), unsaturated monobasic acid (B), and polybasic acid anhydride (C) as essential reaction raw materials. For example, the resin having the acidic group and polymerizable unsaturated group may be produced by reacting all the reaction raw materials at once, or by reacting the reaction raw materials sequentially. Among these, the method of first reacting the epoxy resin (A) with the unsaturated monobasic acid (B), and then reacting with the polybasic acid anhydride (C) is preferred because the reaction is easy to control. This reaction can be carried out, for example, by reacting the epoxy resin (A) with the unsaturated monobasic acid (B) in the presence of a basic catalyst at a temperature range of 100 to 150°C, then adding the polybasic acid anhydride (C) to the reaction system and reacting at a temperature range of 80 to 140°C. 【0078】 In this embodiment, the reaction ratio of the epoxy resin (A) to the unsaturated monobasic acid (B) is preferably in the range of 0.9 to 1.1 moles of unsaturated monobasic acid (B) per mole of epoxy groups in the epoxy resin (A). Furthermore, the reaction ratio of the polybasic acid anhydride (C) is preferably in the range of 0.2 to 1.1 moles per mole of epoxy groups in the epoxy resin (A). 【0079】 Examples of the aforementioned organic solvents include hydrocarbon solvents such as toluene, xylene, heptane, hexane, and mineral spirits; ketone solvents such as methyl ethyl ketone, acetone, dimethylformamide, methyl isobutyl ketone, cyclohexanone, and dimethylacetamide; cyclic ether solvents such as tetrahydrofuran and dioxolane; ester solvents such as methyl acetate, ethyl acetate, and butyl acetate; aromatic solvents such as toluene, xylene, and solvent naphtha; alicyclic solvents such as cyclohexane and methylcyclohexane; and carbitol, cellosolve, methanol, ethanol, propanol, isopropanol, butanol, and cyclohexanone. Examples of organic solvents include alcohol solvents such as propylene glycol monomethyl ether; ether solvents such as propyl ether, methyl cellosolve, cellosolve, butyl cellosolve, and methyl carbitol; glycol ether solvents such as alkylene glycol monoalkyl ether, dialkylene glycol monoalkyl ether, and dialkylene glycol monoalkyl ether acetate; vegetable oils such as soybean oil, linseed oil, rapeseed oil, and safflower oil; and methoxypropanol, cyclohexanone, methyl cellosolve, diethylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate. These organic solvents may be used individually or in combination of two or more. 【0080】 Furthermore, commercially available organic solvents can also be used, such as ENEOS Corporation's "Spindle Oil No. 1", "Solvent No. 3", "Solvent No. 4", "Solvent No. 5", "Solvent No. 6", "Naphthezol H", "Alken 56NT", "AF Solvent No. 4", "AF Solvent No. 5", "AF Solvent No. 6", "AF Solvent No. 7", Mitsubishi Chemical Corporation's "Diadol 13", "Dialen 168"; Nissan Chemical Corporation's "F Oxocol", "F Oxocol 180"; Idemitsu Kosan Co., Ltd.'s "Supersol LA35", "Supersol LA38"; ExxonMobil Examples include Chemical's "Exsol D80," "Exsol D110," "Exsol D120," "Exsol D130," "Exsol D160," "Exsol D100K," "Exsol D120K," "Exsol D130K," "Exsol D280," "Exsol D300," and "Exsol D320." In this embodiment, the amount of organic solvent used is preferably in the range of 0.1 to 5 times the total mass of the reaction raw materials, as this results in good reaction efficiency. 【0081】 Examples of the basic catalyst include N-methylmorpholine, pyridine, N,N-dimethyl-4-aminopyridine, 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1,4-diazabicyclo[2.2.2]octane (DABCO), tri-n-butylamine or dimethylbenzylamine, butylamine, octylamine, monoethanolamine, diethanolamine, triethanolamine, Amine compounds such as imidazole, 1-methylimidazole, 2,4-dimethylimidazole, 1,4-diethylimidazole, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-(N-phenyl)aminopropyltrimethoxysilane, 3-(2-aminoethyl)aminopropyltrimethoxysilane, 3-(2-aminoethyl)aminopropylmethyldimethoxysilane, tetramethylammonium hydroxide, etc.; trioctylmethylammonium Examples include quaternary ammonium salts such as muchlorides and trioctylmethylammonium acetate; phosphines such as trimethylphosphine, tributylphosphine, and triphenylphosphine; phosphonium salts such as tetramethylphosphonium chloride, tetraethylphosphonium chloride, tetrapropylphosphonium chloride, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, trimethyl(2-hydroxylpropyl)phosphonium chloride, triphenylphosphonium chloride, and benzylphosphonium chloride; organotin compounds such as dibutyltin dilaurate, octyltin trilaurate, octyltin diacetate, dioctyltin diacetate, dioctyltin dianeodecanoate, dibutyltin diacetate, tin octoate, and 1,1,3,3-tetrabutyl-1,3-dodecanoyldistanoxane; organometallic compounds such as zinc octoate and bismuth octoate; inorganic tin compounds such as tin octanoate; and inorganic metal compounds. Alkaline earth metal hydroxides, alkali metal carbonates, and alkali metal hydroxides can also be used. The basic catalyst may be used alone or in combination of two or more types. Furthermore, the amount of basic catalyst added is preferably in the range of 0.001 to 5 parts by mass per 100 parts by mass of the total reaction raw materials. 【0082】 The acid value of the resin having acidic groups and polymerizable unsaturated groups in this embodiment is preferably in the range of 30 to 150 mg KOH / g, and more preferably in the range of 40 to 120 mg KOH / g, from the viewpoint of more effectively improving photosensitivity, developability, adhesion, low modulus of elasticity, and low dielectric properties. In this disclosure, the acid value of the resin having acidic groups and polymerizable unsaturated groups in this embodiment is the value measured by the neutralization titration method of JIS 0070 (1992). 【0083】 <Curable resin composition> The curable resin composition of this embodiment is characterized by containing a resin having the above-mentioned acid group and polymerizable unsaturated group. By curing the curable resin composition of this embodiment, it is possible to obtain a cured product with high heat resistance, high adhesion, and low elastic modulus. 【0084】 (Photopolymerization initiator) The curable resin composition of this embodiment preferably further contains a photopolymerization initiator. The inclusion of a photopolymerization initiator in the curable resin composition facilitates the initiation of the photo-induced curing reaction (polymerization). The photopolymerization initiator may be used alone or in combination of two or more types. 【0085】 The aforementioned photopolymerization initiator can be selected and used appropriately depending on the type of active energy ray to be irradiated. It may also be used in combination with photosensitizers such as amine compounds, urea compounds, sulfur-containing compounds, phosphorus-containing compounds, chlorine-containing compounds, and nitrile compounds. Furthermore, the photopolymerization initiator is preferably a radical polymerization initiator. Specific examples of such photopolymerization initiators include alkylphenone-based photopolymerization initiators such as 1-hydroxycyclohexylphenyl-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone, and 1,2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone; acylphosphine oxide-based photopolymerization initiators such as 2,4,6-trimethylbenzoyl-diphenylphosphine oxide; and intramolecular hydrogen abstraction type photopolymerization initiators such as benzophenone compounds. 【0086】 Furthermore, specific examples of the photopolymerization initiator include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, thioxanthones and thioxanthone derivatives, 2,2'-dimethoxy-1,2-diphenylethane-1-one, diphenyl(2,4,6-trimethoxybenzoyl)phosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, and the like. 【0087】 Examples of commercially available photopolymerization initiators include "Omnirad-1173", "Omnirad-184", "Omnirad-127", "Omnirad-2959", "Omnirad-369", "Omnirad-379", "Omnirad-907", "Omnirad-4265", "Omnirad-1000", "Omnirad-651", "Omnirad-TPO", "Omnirad-819", "Omnirad-2022", "Omnirad-2100", "Omnirad-754", "Omnirad-784", "Omnirad-500", "Om Examples include "nirad-81" (manufactured by IGM), "KayaCure-DETX", "KayaCure-MBP", "KayaCure-DMBI", "KayaCure-EPA", "KayaCure-OA" (manufactured by Nippon Kayaku Co., Ltd.), "ByCure-10", "ByCure-55" (manufactured by Stauffa Chemical), "Trigonal P1" (manufactured by Akzo), "Sandoz 1000" (manufactured by Sandoz), "Deep" (manufactured by Apjohn), "Quantacure-PDO", "Quantacure-ITX", "Quantacure-EPD" (manufactured by Ward Blenkinsop), and "Runtecure-1104" (manufactured by Runtec). 【0088】 When using the aforementioned photopolymerization initiator, the content of the photopolymerization initiator in the curable resin composition of this embodiment is preferably 0.1 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the resin having acidic groups and polymerizable unsaturated groups. 【0089】 (Resin(D) having acid groups and polymerizable unsaturated groups other than the aforementioned resin having acid groups and polymerizable unsaturated groups) The curable resin composition of this embodiment may further contain a resin (D) having acid groups and polymerizable unsaturated groups other than the resin having acid groups and polymerizable unsaturated groups described above (i.e., the reaction product of epoxy resin (A), unsaturated monobasic acid (B), and polybasic acid anhydride (C)) (hereinafter sometimes simply referred to as "resin (D)"). 【0090】 Examples of acidic groups in resin (D) include carboxyl groups, sulfonic acid groups, and phosphoric acid groups. Among these, carboxyl groups are preferred as acidic groups because they exhibit excellent alkali developability. Examples of polymerizable unsaturated groups in resin (D) include (meth)acryloyl groups, allyl groups, isopropenyl groups, 1-propenyl groups, styryl groups, styrylmethyl groups, maleimide groups, and vinyl ether groups. 【0091】 Examples of the aforementioned resin (D) include the following [1] to [6]: [1] Epoxy resin having acid groups and polymerizable unsaturated groups (D1), [2] Urethane resin having acidic groups and polymerizable unsaturated groups (D2) [3] Acrylic resin (D3) having acidic groups and polymerizable unsaturated groups, [4] Amidoimide resin having acid groups and polymerizable unsaturated groups (D4), [5] Acrylamide resin having acidic groups and polymerizable unsaturated groups (D5), [6] Ester resin having acidic groups and polymerizable unsaturated groups (D6), Examples include resins such as the following. The epoxy resin (D1) to the ester resin (D6) will be described below in order. 【0092】 --Epoxy resin (D1) having acidic groups and polymerizable unsaturated groups-- Examples of the epoxy resin (D1) having acidic groups and polymerizable unsaturated groups include epoxy (meth)acrylate resins having acidic groups, which require epoxy resin (d1-1), unsaturated monobasic acid (d1-2), and polybasic acid anhydride (d1-3) as essential reaction raw materials, and epoxy (meth)acrylate resins having acidic groups and urethane bonds, which require epoxy resin (d1-1), unsaturated monobasic acid (d1-2), polybasic acid anhydride (d1-3), polyisocyanate compound (d1-4), and (meth)acrylate compound (d1-5) having hydroxyl groups as reaction raw materials. 【0093】 The epoxy resin (d1-1) is not particularly limited in its specific structure, as long as it has multiple epoxy groups in the resin. Examples of the epoxy resin (d1-1) include bisphenol type epoxy resin, hydrogenated bisphenol type epoxy resin, biphenol type epoxy resin, hydrogenated biphenol 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, cresol novolac type epoxy resin, bisphenol novolac type epoxy resin, naphthol novolac type epoxy resin, naphthol-phenol copolymer novolac type epoxy resin, naphthol-cresol copolymer novolac type epoxy resin, phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene-phenol addition reaction type epoxy resin, biphenyl aralkyl type epoxy resin, fluorene type epoxy resin, xanthene type epoxy resin, dihydroxybenzene type epoxy resin, trihydroxybenzene type epoxy resin, oxazolidone type epoxy resin, and the like. These epoxy resins may be used individually or in combination of two or more types. 【0094】 Examples of the bisphenol-type epoxy resins include bisphenol A type epoxy resin, bisphenol AP type epoxy resin, bisphenol B type epoxy resin, bisphenol BP type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, and bisphenol S type epoxy resin. Examples of the hydrogenated bisphenol type epoxy resins include hydrogenated bisphenol A type epoxy resin, hydrogenated bisphenol B type epoxy resin, hydrogenated bisphenol E type epoxy resin, hydrogenated bisphenol F type epoxy resin, and hydrogenated bisphenol S type epoxy resin. Examples of the biphenol-type epoxy resins include 4,4'-biphenol-type epoxy resin, 2,2'-biphenol-type epoxy resin, tetramethyl-4,4'-biphenol-type epoxy resin, and tetramethyl-2,2'-biphenol-type epoxy resin. Examples of the hydrogenated biphenol type epoxy resin include hydrogenated 4,4'-biphenol type epoxy resin, hydrogenated 2,2'-biphenol type epoxy resin, hydrogenated tetramethyl-4,4'-biphenol type epoxy resin, hydrogenated tetramethyl-2,2'-biphenol type epoxy resin, and the like. The epoxy resin (b1-1) may be used alone or in combination of two or more. 【0095】 Examples of the unsaturated monobasic acid (d1-2) include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, α-cyanocinnamic acid, β-styrylacrylic acid, β-furfurylacrylic acid, and the like. Further, acid halides and esterified products of the unsaturated monobasic acid can also be used. Furthermore, as the unsaturated monobasic acid (d1-2), the following general formula (4): 【0096】 【Chemical formula】 [In the above general formula (4), X 41 represents an alkylene chain having 1 to 10 carbon atoms, a polyoxyalkylene chain, a (poly)ester chain, an aromatic hydrocarbon chain, or a (poly)carbonate chain, and a hydrogen atom in the structure of X 41 may be substituted with a halogen atom or an alkoxy group, and Y 41 is a hydrogen atom or a methyl group. Compounds represented by ] can also be used. 【0097】 Examples of the polyoxyalkylene chain include a polyoxyethylene chain, a polyoxypropylene chain, and the like. 【0098】 Examples of the (poly)ester chain include the following general formula (5): 【0099】 【Chemical formula】 [In the above general formula (5), R 51 and R 52 each represent an alkylene group having 1 to 10 carbon atoms, and n51 represents an integer from 1 to 5. Examples include (poly)ester chains represented by ]. 【0100】 Examples of the aromatic hydrocarbon chains include phenylene chains, naphthylene chains, biphenylene chains, phenylnaphthylene chains, or binaphthylene chains. Hydrocarbon chains having aromatic rings such as benzene rings, naphthalene rings, anthracene rings, and phenanthrene rings as partial structures can also be used. 【0101】 Examples of the (poly)carbonate chain include the following general formula (6): 【0102】 [ka] [In the above general formula (6), R 61 This represents an alkylene group with 1 to 10 carbon atoms, n 61 represents an integer from 1 to 5. An example is a (poly)carbonate chain represented by ]. 【0103】 The molecular weight of the compound represented by the above general formula (4) is preferably in the range of 100 to 500, and more preferably in the range of 150 to 400. 【0104】 The aforementioned unsaturated monobasic acids (d1-2) may be used individually or in combination of two or more. 【0105】 Examples of the polybasic acid anhydrides (d1-3) include aliphatic polybasic acid anhydrides, alicyclic polybasic acid anhydrides, aromatic polybasic acid anhydrides, acid halides of aliphatic polybasic acid anhydrides, acid halides of alicyclic polybasic acid anhydrides, and acid halides of aromatic polybasic acid anhydrides. 【0106】 Examples of the aliphatic polybasic acid anhydride include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, citraconic acid, itaconic acid, glutaconic acid, and acid anhydrides of 1,2,3,4-butanetetracarboxylic acid. Furthermore, the aliphatic polybasic acid anhydride may have either linear or branched aliphatic hydrocarbon groups, and may also have unsaturated bonds in its structure. 【0107】 In this invention, the alicyclic polybasic acid anhydride is defined as one in which the acid anhydride group is bonded to an alicyclic structure, and the presence or absence of aromatic rings in other structural parts is irrelevant. Examples of the alicyclic polybasic acid anhydride include 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, and acid anhydrides of 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic acid. 【0108】 Examples of the aforementioned aromatic polybasic acid anhydrides include phthalic acid, trimellitic acid, pyromellitic acid, naphthalenedicarboxylic acid, naphthalentricarboxylic acid, naphthalenetetracarboxylic acid, biphenyldicarboxylic acid, biphenyltricarboxylic acid, biphenyltetracarboxylic acid, and benzophenonetetracarboxylic acid. 【0109】 The polybasic acid anhydrides (d1-3) may be used individually or in combination of two or more. Among these, tetrahydrophthalic anhydride, succinic anhydride, and cyclohexanedicarboxylic acid anhydride are preferred from the viewpoint of more effectively improving photosensitivity, developability, heat resistance, adhesion, and elongation. 【0110】 Examples of the polyisocyanate compounds (d1-4) include aliphatic diisocyanate compounds such as butane diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,4,4-trimethylhexamethylene diisocyanate; alicyclic diisocyanate compounds such as norbornane diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, and hydrogenated diphenylmethane diisocyanate; aromatic diisocyanate compounds such as tolylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, 4,4'-diisocyanato-3,3'-dimethylbiphenyl, and o-tolidine diisocyanate; and the following general formula (7): 【0111】 [ka] [In the above general formula (7), R 72 and R 73 Each of these independently represents either a hydrogen atom or a monovalent hydrocarbon group having 1 to 6 carbon atoms, and R 71 Each of these independently represents an alkyl group with 1 to 4 carbon atoms, and k 71 n is an integer between 0 and 3, and n 71 is an integer greater than or equal to 1. Examples include polymethylene polyphenyl polyisocyanates having a repeating structure represented by ]; isocyanurate modified versions, biuret modified versions, allophanate modified versions, etc. The polyisocyanate compounds (d1-4) may be used individually or in combination of two or more. 【0112】 Examples of the hydroxyl group-containing (meth)acrylate compounds (d1-5) include hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, trimethylolpropane (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol (meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol (meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ditrimethylolpropane (meth)acrylate, ditrimethylolpropane di(meth)acrylate, and ditrimethylolpropane tri(meth)acrylate. Furthermore, polyoxyalkylene modified compounds, in which polyoxyalkylene chains such as polyoxyethylene chains, polyoxypropylene chains, and polyoxytetramethylene chains are introduced into the molecular structure of the various hydroxyl group-containing (meth)acrylate compounds, and lactone modified compounds, in which a polylactone structure is introduced into the molecular structure of the various hydroxyl group-containing (meth)acrylate compounds, can also be used. Among these, those with a molecular weight of 1,000 or less are preferred from the viewpoint of more effectively improving light sensitivity, developability, heat resistance, adhesion, and elongation. Furthermore, if the (meth)acrylate compound (d1-5) having a hydroxyl group is an oxyalkylene modified or lactone modified, it is preferable that its weight-average molecular weight (Mw) is 1,000 or less. The hydroxyl group-containing (meth)acrylate compounds (d1-5) may be used individually or in combination of two or more. 【0113】 The method for producing the epoxy resin (D1) having the acidic group and polymerizable unsaturated group is not particularly limited and can be any method. In producing the epoxy resin (D1) having the acidic group and polymerizable unsaturated group, the process may be carried out in an organic solvent as needed, and a basic catalyst may also be used as needed. 【0114】 The method for producing the epoxy resin (D1) having the acid group and polymerizable unsaturated group is not particularly limited, as long as the epoxy resin (d1-1), unsaturated monobasic acid (d1-2), and polybasic acid anhydride (d1-3) are essential reaction raw materials, or as long as the epoxy resin (d1-1), unsaturated monobasic acid (d1-2), polybasic acid anhydride (d1-3), polyisocyanate compound (d1-4), and (meth)acrylate compound (d1-5) having a hydroxyl group are used as reaction raw materials. For example, the epoxy resin (D1) may be produced by reacting all the reaction raw materials at once, or by reacting the reaction raw materials sequentially. Among these, the method of reacting the epoxy resin (d1-1) with the unsaturated monobasic acid (d1-2) first, and then with the polybasic acid anhydride (d1-3), is preferred because the reaction can be easily controlled. This reaction can be carried out, for example, by reacting an epoxy resin (d1-1) with an unsaturated monobasic acid (d1-2) in the presence of a basic catalyst at a temperature range of 100 to 150°C, then adding a polybasic acid anhydride (d1-3) to the reaction system and reacting at a temperature range of 80 to 140°C. 【0115】 The reaction ratio of the epoxy resin (d1-1) to the unsaturated monobasic acid (d1-2) is preferably in the range of 0.9 to 1.1 moles of unsaturated monobasic acid (d1-2) per mole of epoxy groups in the epoxy resin (d1-1). Furthermore, the reaction ratio of the polybasic anhydride (d1-3) is preferably in the range of 0.2 to 1.0 moles per mole of epoxy groups in the epoxy resin (d1-1). 【0116】 The organic solvent can be the same as the organic solvent described in the section above for "resins having acidic groups and polymerizable unsaturated groups," and the organic solvent may be used alone or in combination of two or more types. 【0117】 The amount of the aforementioned organic solvent used is preferably in the range of 0.1 to 5 times the total mass of the reaction raw materials, as this results in good reaction efficiency. 【0118】 The basic catalyst can be the same as the basic catalyst described in the section above for "resins having acidic groups and polymerizable unsaturated groups," and the basic catalyst may be used alone or in combination of two or more types. Furthermore, the amount of basic catalyst added is preferably in the range of 0.001 to 5 parts by mass per 100 parts by mass of the total reaction raw materials. 【0119】 The acid value of the epoxy resin (D1) having the acid group and polymerizable unsaturated group is preferably in the range of 30 to 150 mg KOH / g, and more preferably in the range of 40 to 120 mg KOH / g, from the viewpoint of more effectively improving photosensitivity, developability, heat resistance, adhesion, and elongation. In this disclosure, the acid value of the epoxy resin (D1) having the acid group and polymerizable unsaturated group is the value measured by the neutralization titration method of JIS 0070 (1992). 【0120】 --Urethane resin (D2) having acidic groups and polymerizable unsaturated groups-- The urethane resin (D2) having the acid group and polymerizable unsaturated group is, for example, a resin obtained by reacting a polyisocyanate compound (d1-4), a hydroxyl group-containing (meth)acrylate compound (d1-5), a carboxyl group-containing polyol compound (d2-1), and, if necessary, a polybasic acid anhydride (d1-3) and a polyol compound other than the carboxyl group-containing polyol compound (d2-2); polyisocyanate compound (d1-4) and hydroxyl group-containing Examples include resins obtained by reacting (meth)acrylate compounds (d1-5) with polybasic acid anhydrides (d1-3) and polyol compounds other than carboxyl group-containing polyol compounds (d2-1) (d2-2); or resins obtained by reacting epoxy resin (d1-1) with unsaturated monobasic acid (d1-2), polybasic acid anhydrides (d1-3), polyisocyanate compounds (d1-4), and hydroxyl group-containing (meth)acrylate compounds (d1-5). 【0121】 Examples of the carboxyl group-containing polyol compound (d2-1) include 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, and 2,2-dimethylolvaleric acid. The carboxyl group-containing polyol compound can be used alone or in combination of two or more types. 【0122】 Examples of polyol compounds other than the carboxyl group-containing polyol compound (d2-1) (d2-2) include aliphatic polyol compounds such as ethylene glycol, propylene glycol, butanediol, hexanediol, glycerin, trimethylolpropane, ditrimethylolpropane, pentaerythritol, and dipentaerythritol; aromatic polyol compounds such as biphenol and bisphenol; (poly)oxyalkylene modified compounds obtained by introducing (poly)oxyalkylene chains such as (poly)oxyethylene chains, (poly)oxypropylene chains, and (poly)oxytetramethylene chains into the molecular structure of the various polyol compounds; and lactone modified compounds obtained by introducing (poly)lactone structures into the molecular structure of the various polyol compounds. The polyol compounds other than the carboxyl group-containing polyol compound can be used alone or in combination of two or more types. 【0123】 The method for producing the urethane resin (D2) having the acid group and polymerizable unsaturated group is not particularly limited and can be any method. The production of the urethane resin having the acid group and polymerizable unsaturated bond may be carried out in an organic solvent as needed, and a basic catalyst may also be used as needed. 【0124】 The organic solvent can be the same as the organic solvent described in the section above for "resins having acidic groups and polymerizable unsaturated groups," and the organic solvent can be used alone or in combination of two or more types. Furthermore, the basic catalyst can be the same as the basic catalyst described in the section above for "resins having acidic groups and polymerizable unsaturated groups," and the basic catalyst can be used alone or in combination of two or more types. 【0125】 --Acrylic resin (D3) having acidic groups and polymerizable unsaturated groups-- Examples of the acrylic resin (D3) having the acid group and polymerizable unsaturated group include a reaction product obtained by introducing a (meth)acryloyl group by further reacting an acrylic resin intermediate obtained by polymerizing an acrylic resin intermediate having a reactive functional group such as a hydroxyl group, carboxyl group, isocyanate group, or glycidyl group with a (meth)acrylate compound (β) having a reactive functional group that can react with these functional groups, or a resin obtained by reacting a polybasic acid anhydride (d1-3) with the hydroxyl group in the reaction product. 【0126】 The acrylic resin intermediate may be copolymerized with other polymerizable unsaturated group-containing compounds as needed, in addition to the (meth)acrylate compound (α). Examples of such other polymerizable unsaturated group-containing compounds include alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate; alicyclic structure-containing (meth)acrylates such as cyclohexyl (meth)acrylate, isobolonyl (meth)acrylate, and dicyclopentanyl (meth)acrylate; aromatic ring-containing (meth)acrylates such as phenyl (meth)acrylate, benzyl (meth)acrylate, and phenoxyethyl acrylate; silyl group-containing (meth)acrylates such as 3-methacryloxypropyltrimethoxysilane; and styrene derivatives such as styrene, α-methylstyrene, and chlorostyrene. The aforementioned other polymerizable unsaturated group-containing compounds can be used individually or in combination of two or more. 【0127】 The (meth)acrylate compound (β) is not particularly limited as long as it can react with the reactive functional group of the (meth)acrylate compound (α), but from the viewpoint of reactivity, the following combinations are preferred. That is, when a hydroxyl group-containing (meth)acrylate is used as the (meth)acrylate compound (α), it is preferable to use an isocyanate group-containing (meth)acrylate as the (meth)acrylate compound (β). When a carboxyl group-containing (meth)acrylate is used as the (meth)acrylate compound (α), it is preferable to use a glycidyl group-containing (meth)acrylate as the (meth)acrylate compound (β). When an isocyanate group-containing (meth)acrylate is used as the (meth)acrylate compound (α), it is preferable to use a hydroxyl group-containing (meth)acrylate as the (meth)acrylate compound (β). When a glycidyl group-containing (meth)acrylate is used as the (meth)acrylate compound (α), it is preferable to use a carboxyl group-containing (meth)acrylate as the (meth)acrylate compound (β). The (meth)acrylate compound (β) can be used alone or in combination of two or more types. 【0128】 The method for producing the acrylic resin (D3) having the acidic group and polymerizable unsaturated group is not particularly limited and can be any method. The production of the acrylic resin (D3) having the acidic group and polymerizable unsaturated group may be carried out in an organic solvent if necessary, and a basic catalyst may also be used if necessary. The organic solvent can be the same as the organic solvent described in the section above for "resins having acidic groups and polymerizable unsaturated groups," and the organic solvent can be used alone or in combination of two or more types. As the basic catalyst, the same basic catalyst as described in the section above, "Resin having acidic groups and polymerizable unsaturated groups," can be used, and the basic catalyst can be used alone or in combination of two or more types. 【0129】 The acid value of the acrylic resin (D3) having the acid group and polymerizable unsaturated group is preferably in the range of 30 to 150 mg KOH / g, and more preferably in the range of 40 to 120 mg KOH / g, from the viewpoint of more effectively improving photosensitivity, developability, heat resistance, adhesion, and elongation. 【0130】 --Amido-imide resin (D4) having acidic groups and polymerizable unsaturated groups-- Examples of the amide-imide resin (D4) having the acid group and polymerizable unsaturated group include those obtained by reacting an amide-imide resin (d4-1) having an acid group and / or an acid anhydride group with a (meth)acrylate compound (d1-5) having a hydroxyl group and / or an epoxy group having a compound having one or more reactive functional groups selected from the group consisting of a hydroxyl group, a carboxyl group, an isocyanate group, a glycidyl group, and an acid anhydride group. The compound having the reactive functional group may or may not have a (meth)acryloyl group. 【0131】 The amide-imide resin (d4-1) having acid groups and / or acid anhydride groups may have only one of them, or both. From the viewpoint of reactivity and reaction control with (meth)acrylate compounds (d1-5) having hydroxyl groups or epoxy compounds having (meth)acryloyl groups, it is preferable that the amide-imide resin (d4-1) has acid anhydride groups, and more preferably that it has both acid groups and acid anhydride groups. The solid content acid value of the amide-imide resin (d4-1) is preferably in the range of 60 to 350 mgKOH / g when measured under neutral conditions, i.e., conditions in which the acid anhydride groups are not ring-opened. On the other hand, it is preferable that the measured value is in the range of 61 to 360 mgKOH / g when measured under conditions in which the acid anhydride groups are ring-opened, such as in the presence of water. 【0132】 Furthermore, the amide-imide resin (d4-1) can also be used in combination with polybasic acids as reaction raw materials, in addition to polyisocyanate compounds (d1-4) and polybasic acid anhydrides (d1-3), if necessary. 【0133】 As the aforementioned polybasic acid, any compound having two or more carboxyl groups in one molecule can be used. For example, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, citraconic acid, itaconic acid, glutaconic acid, 1,2,3,4-butanetetracarboxylic acid, cyclohexanetricarboxylic acid, cyclohexanetetracarboxylic acid, bicyclo[2.2.1]heptane-2,3 Examples of polybasic acids include dicarboxylic acids, methylbicyclo[2.2.1]heptane-2,3-dicarboxylic acid, 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic acid, trimellitic acid, pyromellitic acid, naphthalenedicarboxylic acid, naphthalentricarboxylic acid, naphthalenetetracarboxylic acid, biphenyldicarboxylic acid, biphenyltricarboxylic acid, biphenyltetracarboxylic acid, benzophenonetetracarboxylic acid, and the like. In addition, as the polybasic acid, for example, a copolymer of a conjugated diene vinyl monomer and acrylonitrile having a carboxyl group in its molecule can also be used. The aforementioned polybasic acids can be used individually or in combination of two or more. 【0134】 The (meth)acrylate compound having the epoxy group is not particularly limited in terms of its specific structure as long as it has a (meth)acryloyl group and an epoxy group in its molecular structure, and a wide variety of compounds can be used. Examples include glycidyl group-containing (meth)acrylate monomers such as glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, and epoxycyclohexylmethyl (meth)acrylate, as well as mono(meth)acrylates of diglycidyl ether compounds such as hydroxybenzene diglycidyl ether, dihydroxynaphthalene diglycidyl ether, biphenol diglycidyl ether, and bisphenol diglycidyl ether. The (meth)acrylate compounds having the epoxy group can be used alone or in combination of two or more. 【0135】 Furthermore, the specific structure or manufacturing method of the amide-imide resin (d4-1) having the acid group and / or acid anhydride group is not particularly limited, and general amide-imide resins can be widely used. The amide-imide resin (d4-1) in this embodiment is preferably obtained using a polyisocyanate compound (d1-4) and a polybasic acid anhydride (d1-3) as reaction raw materials. 【0136】 Furthermore, as the polyisocyanate compound (d1-4), a resin composition having acidic groups with high solvent solubility and polymerizable unsaturated groups can be obtained, so alicyclic diisocyanate compounds or modified thereof, aliphatic diisocyanate compounds or modified thereof are preferred, and alicyclic diisocyanate or its isocyanurate modified, aliphatic diisocyanate or its isocyanurate modified are more preferred. Preferably, the total mass ratio of alicyclic diisocyanate compounds or their modified counterparts to aliphatic diisocyanate compounds or their modified counterparts in the total mass of the polyisocyanate compounds (d1-4) is 70% by mass or more, and more preferably 90% by mass or more. Furthermore, when using an alicyclic diisocyanate compound or a modified version thereof in combination with an aliphatic diisocyanate compound or a modified version thereof, it is preferable that the mass ratio of the two (alicyclic diisocyanate compound or modified version thereof / aliphatic diisocyanate compound or modified version thereof) is in the range of 30 / 70 to 70 / 30. 【0137】 The method for producing the amide-imide resin (D4) having the acidic group and polymerizable unsaturated group is not particularly limited and can be any method. In producing the amide-imide resin (D4) having the acidic group and polymerizable unsaturated group, the process may be carried out in an organic solvent as needed, and a basic catalyst may also be used as needed. As the basic catalyst, the same basic catalyst as described in the section above, "Resin having acidic groups and polymerizable unsaturated groups," can be used, and the basic catalyst can be used alone or in combination of two or more types. Furthermore, the organic solvent can be the same as the organic solvent described in the section above for "resins having acidic groups and polymerizable unsaturated groups," and the organic solvent can be used alone or in combination of two or more types. 【0138】 The amide-imide resin (D4) having acid groups and polymerizable unsaturated groups can be used in combination with other reaction materials in addition to the reaction materials of amide-imide resin (d4-1) having acid groups and / or acid anhydride groups, hydroxyl group-containing (meth)acrylate compounds (d1-5), and / or epoxy group-containing (meth)acrylate compounds (d4-2), depending on the desired resin performance. In this case, it is preferable that the total mass ratio of the components (d4-1) to (d4-2) in the total mass of the reaction materials for the resin (D4) having acid groups and polymerizable unsaturated groups be 80% by mass or more, and more preferably 90% by mass or more. 【0139】 The method for producing the amide-imide resin (D4) having acidic groups and polymerizable unsaturated groups is not particularly limited and can be any method. For example, it may be produced by reacting all the reaction materials, including the amide-imide resin (d4-1) and the hydroxyl group-containing (meth)acrylate compound (d1-5) and / or the epoxy group-containing (meth)acrylate compound (d4-2), all at once, or by reacting the reaction materials sequentially. For example, the reaction between the amide-imide resin (d4-1) and the hydroxyl group-containing (meth)acrylate compound (d1-5) can be carried out by heating and stirring under temperature conditions of about 80 to 140°C in the presence of a suitable basic catalyst. In the production of the amide-imide resin (D4) having acidic groups and polymerizable unsaturated groups, it may be carried out in an organic solvent as needed, and a basic catalyst or an acidic catalyst may be used as needed. 【0140】 The basic catalyst can be the same as the acidic catalyst and basic catalyst described in the section above, "Resin having acidic groups and polymerizable unsaturated groups," and these can be used individually or in combination of two or more. Examples of the acidic catalysts include inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid; organic acids such as methanesulfonic acid, p-toluenesulfonic acid, and oxalic acid; and Lewis acids such as boron trifluoride, anhydrous aluminum chloride, and zinc chloride. Solid acid catalysts having strong acids such as sulfonyl groups can also be used. These acidic catalysts can be used individually or in combination of two or more types. 【0141】 The acid value of the amide-imide resin (D4) having the acid group and polymerizable unsaturated group is preferably in the range of 30 to 150 mg KOH / g, and more preferably in the range of 40 to 120 mg KOH / g, from the viewpoint of more effectively improving photosensitivity, developability, heat resistance, adhesion, and elongation. 【0142】 --Acrylamide resin (D5) having acidic groups and polymerizable unsaturated groups-- Examples of the acrylamide resin (D5) having the acid group and polymerizable unsaturated group include a resin obtained by reacting a phenolic hydroxyl group-containing compound (d5-1), an alkylene carbonate (d5-2a) or alkylene oxide (d5-2b), an N-alkoxyalkyl (meth)acrylamide compound (d5-3), a polybasic acid anhydride (d1-3), and optionally an unsaturated monobasic acid (d1-2) as reaction raw materials. 【0143】 The phenolic hydroxyl group-containing compound (d5-1) refers to a compound having at least one phenolic hydroxyl group in its molecule. Examples of phenolic hydroxyl group-containing compounds (d5-1) include compounds represented by any of the following general formulas (8.1) to (8.5), reaction products using an aromatic polyhydroxy compound (d5-4) and a compound represented by any of the following general formulas (9.1) to (9.5) as essential reaction raw materials, or novolac-type phenolic resins using one or more aromatic polyhydroxy compounds (d5-4) or other compounds (d5-5) having one phenolic hydroxyl group in their molecule as reaction raw materials. 【0144】 [ka] [In the above general formulas (8.1) to (8.5), R 81 ~R 84 and R 87 Each of these independently represents one of the following: an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group, or a halogen atom. 85 and R 86 Each of these independently represents a hydrogen atom or a methyl group, and j 81 ~j 84 and j 87 Each of these independently represents an integer of 0 or 1 or more, preferably an integer between 0 and 3, and more preferably 0 or 1. 81 ~k 84 and k 87 Each of these independently represents an integer of 1 or greater, preferably 2 or 3. 【0145】 Furthermore, the positions of substituents on the aromatic rings in the above general formulas (8.1) to (8.5) are arbitrary. For example, in the naphthalene ring of general formula (8.2), the substituent may substitute for any hydrogen atom on the ring; in general formula (8.3), it may substitute for any hydrogen atom on the benzene ring present in one biphenyl molecule; in general formula (8.4), it may substitute for any hydrogen atom on the benzene ring present in one aralkyl molecule; and in general formula (8.5), it may substitute for any hydrogen atom on the benzene ring present in one molecule. The number of substituents in one molecule is j. 81 ~j 84 , j 87 and k 81 ~k 84 , k 87 This indicates that... 【0146】 [ka] [In the above general formulas (9.1) to (9.5), h 91 represents 0 or 1, R 91 ~R 96 Each of these independently represents one of the following: a monovalent aliphatic hydrocarbon group, an alkoxy group, a halogen atom, an aryl group, an aryloxy group, or an aralkyl group, k 91 ~k 96 Each of these independently represents either 0 or an integer from 1 to 4, and Z 91 ~Z 96 Each of these independently represents one of the following: a vinyl group, a halomethyl group, a hydroxymethyl group, or an alkyloxymethyl group, Y 91 n represents one of the following: an alkylene group with 1 to 4 carbon atoms, an oxygen atom, a sulfur atom, or a carbonyl group. 91 [This represents an integer between 1 and 4.] The compounds represented by the above general formulas (9.1) to (9.5) can be used individually or in combination of two or more. 【0147】 Examples of the aromatic polyhydroxy compounds (d5-4) include dihydroxybenzene, trihydroxybenzene, tetrahydroxybenzene, dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxyanthracene, trihydroxyanthracene, tetrahydroxyanthracene, biphenol, tetrahydroxybiphenyl, bisphenol, and compounds having one or more substituents on these aromatic nuclei. Furthermore, examples of substituents on the aromatic nucleus include monovalent aliphatic hydrocarbon groups such as methyl, ethyl, vinyl, propyl, butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, and nonyl groups; alkoxy groups such as methoxy, ethoxy, propyloxy, and butoxy groups; halogen atoms such as fluorine, chlorine, and bromine atoms; phenyl, naphthyl, and anthryl groups, and aryl groups on which these aromatic nuclei are substituted with the aliphatic hydrocarbon groups, alkoxy groups, halogen atoms, etc.; phenyloxy and naphthyloxy groups, and aryloxy groups on which these aromatic nuclei are substituted with the aliphatic hydrocarbon groups, alkoxy groups, halogen atoms, etc.; phenylmethyl, phenylethyl, naphthylmethyl, naphthylethyl groups, and aralkyl groups on which these aromatic nuclei are substituted with the aliphatic hydrocarbon groups, alkoxy groups, halogen atoms, etc. These aromatic polyhydroxy compounds can be used individually or in combination of two or more. Among these, compounds that do not contain halogens are preferred because they yield resins having acidic groups and polymerizable unsaturated groups with high insulating reliability. 【0148】 Examples of the novolac-type phenolic resin include resins obtained by reacting one or more compounds having one phenolic hydroxyl group in their molecule with an aldehyde compound under acidic catalyst conditions. 【0149】 The aforementioned compounds having one phenolic hydroxyl group in the molecule (d5-5) can be any aromatic compound having one hydroxyl group on the aromatic nucleus. Examples include phenol or phenol compounds having one or more substituents on the aromatic nucleus of phenol, naphthol or naphthol compounds having one or more substituents on the aromatic nucleus of naphthol, anthracenol or anthracenol compounds having one or more substituents on the aromatic nucleus of anthracenol, etc. Examples of substituents on the aromatic nucleus include monovalent aliphatic hydrocarbon groups, alkoxy groups, halogen atoms, aryl groups, aryloxy groups, aralkyl groups, etc., with specific examples of each being as described above. These compounds having one phenolic hydroxyl group can be used individually or in combination of two or more. 【0150】 Examples of the aldehyde compounds include formaldehyde; alkyl aldehydes such as acetaldehyde, propylaldehyde, butyraldehyde, isobutyraldehyde, pentylaldehyde, and hexylaldehyde; hydroxybenzaldehydes such as salicylaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 2-hydroxy-4-methylbenzaldehyde, 2,4-dihydroxybenzaldehyde, and 3,4-dihydroxybenzaldehyde; and 2-hydroxy-3-methoxybenzaldehyde and 3-hydroxy-4-methoxybenzaldehyde. Examples include aldehydes, benzaldehydes having both a hydroxyl group and an alkoxy group, such as 4-hydroxy-3-methoxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, and 4-hydroxy-3,5-dimethoxybenzaldehyde; alkoxybenzaldehydes such as methoxybenzaldehyde and ethoxybenzaldehyde; hydroxynaphthaldehydes such as 1-hydroxy-2-naphthaldehyde, 2-hydroxy-1-naphthaldehyde, and 6-hydroxy-2-naphthaldehyde; and halogenated benzaldehydes such as bromobenzaldehyde. 【0151】 Examples of the alkylene carbonate (d5-2a) include ethylene carbonate, propylene carbonate, butylene carbonate, and pentylene carbonate. Among these, ethylene carbonate or propylene carbonate is preferred from the viewpoint of the resin composition exhibiting higher photosensitivity and developability, and the resulting cured product (cured coating film) exhibiting superior heat resistance, adhesion, and elongation. The alkylene carbonate can be used alone or in combination of two or more types. 【0152】 Examples of the alkylene oxide (d5-2b) include ethylene oxide, propylene oxide, butylene oxide, and pentylene oxide. Among these, ethylene oxide or propylene oxide is preferred from the viewpoint of the resin composition exhibiting higher photosensitivity and developability, and the resulting cured product (cured coating) exhibiting superior heat resistance, adhesion, and elongation. The alkylene oxide can be used alone or in combination of two or more types. 【0153】 Examples of the N-alkoxyalkyl(meth)acrylamide compound (d5-3) include N-methoxymethyl(meth)acrylamide, N-ethoxymethyl(meth)acrylamide, N-butoxymethyl(meth)acrylamide, N-methoxyethyl(meth)acrylamide, N-ethoxyethyl(meth)acrylamide, and N-butoxyethyl(meth)acrylamide. Among these, N-methoxymethyl(meth)acrylamide is preferred from the viewpoint of the resin composition exhibiting higher photosensitivity and developability, and the resulting cured product (cured coating film) exhibiting superior heat resistance, adhesion, and elongation. The N-alkoxyalkyl(meth)acrylamide compound (d5-3) can be used alone or in combination of two or more types. 【0154】 When the N-alkoxyalkyl(meth)acrylamide compound (d5-3) is used as a reaction raw material for an acrylamide resin (D5) having an acid group and a polymerizable unsaturated group, the equivalent ratio of the N-alkoxyalkyl(meth)acrylamide compound (d5-3) to the polybasic acid anhydride (d1-3) [(d5-3) / (d1-3)] is preferably in the range of 0.2 to 7, and more preferably in the range of 0.25 to 6.7, from the viewpoint of the resin composition exhibiting higher photosensitivity and developability, and the resulting cured product (cured coating film) exhibiting better heat resistance, adhesion, and elongation. 【0155】 The method for producing the acrylamide resin (D5) having the acid group and polymerizable unsaturated group is not particularly limited and can be produced by any method. For example, it may be produced by reacting all the reaction materials at once, or by reacting the reaction materials sequentially. In particular, a method is preferred in which the reaction is easily controlled, in which a phenolic hydroxyl group-containing compound (d5-1) is first reacted with an alkylene carbonate (d5-2a) or alkylene oxide (d5-2b) (for example, in the presence of a basic catalyst and at a temperature range of 100 to 200°C), then an unsaturated monobasic acid (d1-2) and / or an N-alkoxyalkyl (meth)acrylamide compound (d2-3b) is reacted (for example, in the presence of an acidic catalyst and at a temperature range of 80 to 140°C), and finally a polybasic acid anhydride (d1-3) is reacted (for example, at a temperature range of 80 to 140°C). 【0156】 The acrylamide resin (D5) having the acid group and polymerizable unsaturated group is a resin obtained from the above reaction raw materials. For example, the acrylamide resin (D5) may be a resin having a resin structure in which structural units are repeatedly formed from structural units (I) represented by the following general formula (10.1) and structural units (II) represented by the following general formula (10.2), or a resin having a resin structure in which structural units are repeatedly formed from structural units (III) represented by the following formula (10.3) and structural units (IV) represented by the following formula (10.4). 【0157】 [ka] [In the above formula (10.1) or (10.2), R b2 and R b8 Each of these independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 4 carbon atoms, and R b3 and R b9 Each of these independently represents one of the following: a hydrogen atom, a hydrocarbon group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom. 1 and n 2 Each of them independently represents either 1 or 2, R b4 and R b10 Each of these independently represents a methylene group or a structural part represented by one of the following general formulas (11.1) to (11.5), and R b5 and R b6 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, however, R b5 and R b6 These may be linked together to form a saturated or unsaturated ring, R b11 R represents a divalent hydrocarbon group with 1 to 12 carbon atoms. b12 R represents a hydrogen atom or a methyl group. b1 and R b7 Each of them independently, R b3 and R b9 The group represented by, or the structural part (I) represented by formula (10.1) or the structural part (II) represented by formula (10.2), is marked with an asterisk (*) in R b4 or R b10 It is a connection point that is linked via [a certain mechanism]. 【0158】 [ka] [In the above general formula (10.3) or (10.4), R b2 and R b8 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, and R b3 and R b9 Each of these independently represents one of the following: a hydrogen atom, a hydrocarbon group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom. 3 and n4 Each independently represents 1 or 2, R b4 and R b10 Each independently represents a methylene group or a structural moiety represented by any of the following formulas (11.1) to (11.5), R b5 and R b6 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, provided that R b5 and R b6 may be linked to form a saturated or unsaturated ring, R b11 represents a divalent hydrocarbon group having 1 to 12 carbon atoms, R b12 represents a hydrogen atom or a methyl group, R b1 and R b7 Each independently represents the group represented by the above R b3 and the above R b9 or a structural moiety (III) represented by the general formula (10.3) or a structural moiety (IV) represented by the general formula (10.4) is a bonding point where the R b4 or R b10 marked with * is linked through.] 【0159】 【Chemical formula】 [In the above general formulas (11.1) to (11.5), h 91 represents 0 or 1, R 91 to R 96 Each independently represents any one of a monovalent aliphatic hydrocarbon group, an alkoxy group, a halogen atom, an aryl group or an aralkyl group, n 91 to n 96 Each independently represents 0 or an integer of 1 to 4, Y 91 represents any one of an alkylene group having 1 to 4 carbon atoms, an oxygen atom, a sulfur atom or a carbonyl group, n 91 represents an integer of 1 to 4, R 111 to R 116 Each independently represents a hydrogen atom or a methyl group, and W represents the following formula (12.1) or (12.2).] 【0160】 【Chemical formula】 [In the above formula (12.1) or (12.2), R 121 and R 124 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms, and R 122 and R 123 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, provided that R 122 and R 123 may be linked to form a saturated or unsaturated ring, and R 125 represents a divalent hydrocarbon group having 1 to 12 carbon atoms, and R 126 represents a hydrogen atom or a methyl group.] 【0161】 From the viewpoint that the acid value of the acrylamide resin (D5) having the acid group and the polymerizable unsaturated group enables the resin composition to exhibit higher photosensitivity and developability, and the resulting cured product (cured coating film) exhibits more excellent heat resistance, adhesion and elongation, the range of 30 to 150 mgKOH / g is preferable, and the range of 40 to 120 mgKOH / g is more preferable. 【0162】 --Ester resin (D6) having an acid group and a polymerizable unsaturated group-- Examples of the ester resin (D6) having the acid group and the polymerizable unsaturated group include resins obtained by reacting a phenolic hydroxyl group-containing compound (d5-1), an alkylene oxide (d5-2b) or an alkylene carbonate (d5-2a), an unsaturated monobasic acid (d1-2), and a polybasic acid anhydride (d1-3). 【0163】 As the alkylene oxide (d5-2b), the same ones as those exemplified above as the alkylene oxide (d5-2b) can be used. Among these, ethylene oxide or propylene oxide is preferable from the viewpoint of more effectively improving photosensitivity, developability, heat resistance, adhesion and elongation. The alkylene oxide (d5-2b) can be used alone or in combination of two or more kinds. 【0164】 As the alkylene carbonate (d5-2a) mentioned above, the same type as the example alkylene carbonate (d5-2a) described above can be used. Among these, ethylene carbonate or propylene carbonate is preferred from the viewpoint of more effectively improving light sensitivity, developability, heat resistance, adhesion, and elongation. The alkylene carbonate (d5-2a) can be used alone or in combination of two or more types. 【0165】 The method for producing the ester resin (D6) having the acidic group and polymerizable unsaturated group is not particularly limited and may be used by any method. The production of the ester resin having the acidic group and polymerizable unsaturated group may be carried out in an organic solvent as needed, and a basic catalyst and an acidic catalyst may be used as needed. 【0166】 The organic solvent can be the same as those exemplified above, and the organic solvent can be used alone or in combination of two or more. The basic catalyst can be the same as those exemplified above, and the basic catalyst can be used alone or in combination of two or more. The acidic catalyst can be the same as those exemplified above, and the acidic catalyst can be used alone or in combination of two or more. 【0167】 (Compounds having polymerizable unsaturated groups) The curable resin composition of this embodiment may further contain a compound having a polymerizable unsaturated group. Such a compound having a polymerizable unsaturated group is typically a compound that does not have an acid group. 【0168】 Examples of compounds having the polymerizable unsaturated group include (meth)acrylate compounds, specifically aliphatic mono(meth)acrylate compounds such as methyl(meth)acrylate, ethyl(meth)acrylate, propyl(meth)acrylate, butyl(meth)acrylate, pentyl(meth)acrylate, hexyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, and octyl(meth)acrylate; and alicyclic compounds such as cyclohexyl(meth)acrylate, isobornyl(meth)acrylate, and adamantylmono(meth)acrylate. Mono(meth)acrylate compounds; heterocyclic mono(meth)acrylate compounds such as glycidyl(meth)acrylate and tetrahydrofurfuryl acrylate; benzyl(meth)acrylate, phenyl(meth)acrylate, phenylbenzyl(meth)acrylate, phenoxy(meth)acrylate, phenoxyethyl(meth)acrylate, phenoxyethoxyethyl(meth)acrylate, 2-hydroxy-3-phenoxypropyl(meth)acrylate, phenoxybenzyl(meth)acrylate, benzylbenzyl(meth)acrylate, phenoxy Mono(meth)acrylate compounds such as aromatic mono(meth)acrylate compounds like phenoxyethyl (meth)acrylate: (Poly)oxyalkylene-modified mono(meth)acrylate compounds obtained by introducing polyoxyalkylene chains such as (poly)oxyethylene chains, (poly)oxypropylene chains, and (poly)oxytetramethylene chains into the molecular structure of the various mono(meth)acrylate monomers; lactone-modified mono(meth)acrylate compounds obtained by introducing a (poly)lactone structure into the molecular structure of the various mono(meth)acrylate compounds; ethylene glycol di( Aliphatic di(meth)acrylate compounds such as meth)acrylate, propylene glycol di(meth)acrylate, butanediol di(meth)acrylate, hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate; alicyclic di(meth)acrylate compounds such as 1,4-cyclohexanedimethanol di(meth)acrylate, norbornane di(meth)acrylate, norbornane dimethanol di(meth)acrylate, dicyclopentanyl di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate;Aromatic di(meth)acrylate compounds such as biphenol di(meth)acrylate and bisphenol di(meth)acrylate; polyoxyalkylene-modified di(meth)acrylate compounds in which (poly)oxyalkylene chains such as (poly)oxyethylene chains, (poly)oxypropylene chains, and (poly)oxytetramethylene chains are introduced into the molecular structure of the above di(meth)acrylate compounds; lactone-modified di(meth)acrylate compounds in which a (poly)lactone structure is introduced into the molecular structure of the above di(meth)acrylate compounds; aliphatic tri(meth)acrylate compounds such as trimethylolpropane tri(meth)acrylate and glycerin tri(meth)acrylate; (poly)oxyalkylene-modified di(meth)acrylate compounds in which (poly)oxyalkylene chains such as (poly)oxyethylene chains, (poly)oxypropylene chains, and (poly)oxytetramethylene chains are introduced into the molecular structure of the above aliphatic tri(meth)acrylate compounds )Oxyalkylene-modified tri(meth)acrylate compounds; lactone-modified tri(meth)acrylate compounds in which a (poly)lactone structure is introduced into the molecular structure of the aliphatic tri(meth)acrylate compound; tetrafunctional or more aliphatic poly(meth)acrylate compounds such as pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, and dipentaerythritol hexa(meth)acrylate; tetrafunctional or more (poly)oxyalkylene-modified poly(meth)acrylate compounds in which a (poly)oxyalkylene chain such as a (poly)oxyethylene chain, a (poly)oxypropylene chain, or a (poly)oxytetramethylene chain is introduced into the molecular structure of the aliphatic poly(meth)acrylate compound; tetrafunctional or more 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;Hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, trimethylolpropane (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol (meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol (meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate (meth)acrylate compounds having hydroxyl groups, such as dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ditrimethylolpropane(meth)acrylate, ditrimethylolpropanedi(meth)acrylate, and ditrimethylolpropanetri(meth)acrylate; (poly)oxyethylene chains, (poly)oxypropylene chains, and (poly)oxytetraacrylates in the molecular structure of the said hydroxyl group-containing (meth)acrylate compounds; Examples include (poly)oxyalkylene modified compounds into which (poly)oxyalkylene chains such as ethylene chains have been introduced; lactone modified compounds into which a (poly)lactone structure has been introduced into the molecular structure of the hydroxyl group-containing (meth)acrylate compound; (meth)acrylate compounds having an isocyanate group such as 2-acryloyloxyethyl isocyanate, 2-methacryloyloxyethyl isocyanate, and 1,1-bis(acryloyloxymethyl)ethyl isocyanate; (meth)acrylate monomers having a glycidyl group such as glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, and epoxycyclohexylmethyl (meth)acrylate; and (meth)acrylate compounds having an epoxy group such as mono(meth)acrylates of diglycidyl ether compounds of droxybenzene diglycidyl ether, dihydroxynaphthalene diglycidyl ether, biphenol diglycidyl ether, and bisphenol diglycidyl ether. The aforementioned polymerizable unsaturated compound may be used alone or in combination of two or more compounds. 【0169】 (Hardening agent) The curable resin composition of this embodiment preferably further contains a curing agent. The curability of the curable resin composition is improved by the inclusion of a curing agent. Examples of the curing agent include epoxy resins and other curing agents (amine curing agents, acid anhydride curing agents, phenol resin curing agents, etc.), but epoxy resins are preferred among these. 【0170】 The epoxy resin is not particularly limited, but is preferably a curable resin that contains two or more epoxy groups in its molecule and can be cured by forming a crosslinked network with the epoxy groups. The epoxy resin is not particularly limited, but may include novolac-type epoxy resins such as phenol novolac-type epoxy resins, cresol novolac-type epoxy resins, α-naphthol novolac-type epoxy resins, β-naphthol novolac-type epoxy resins, bisphenol A novolac-type epoxy resins, and biphenyl novolac-type epoxy resins. Aralkyl epoxy resins such as phenol aralkyl epoxy resins, naphthol aralkyl epoxy resins, and phenol biphenyl aralkyl epoxy resins; Bisphenol-type epoxy resins such as bisphenol A type epoxy resin, bisphenol AP type epoxy resin, bisphenol AF type epoxy resin, bisphenol B type epoxy resin, bisphenol BP type epoxy resin, bisphenol C type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and tetrabromobisphenol A type epoxy resin; Biphenyl-type epoxy resins, tetramethylbiphenyl-type epoxy resins, and epoxy resins having a biphenyl skeleton and a diglycidyloxybenzene skeleton, etc. Naphthalene-type epoxy resin; Binaphthol-type epoxy resin; Binaphthyl-type epoxy resin; Dicyclopentadiene-type epoxy resins, such as dicyclopentadienephenol-type epoxy resins; Glycidylamine-type epoxy resins such as tetraglycidyldiaminodiphenylmethane-type epoxy resins, triglycidyl-p-aminophenol-type epoxy resins, and diaminodiphenylsulfone-type glycidylamine-type epoxy resins; Diglycidyl ester type epoxy resins such as 2,6-naphthalenedicarboxylic acid diglycidyl ester type epoxy resins and hexahydrophthalic anhydride glycidyl ester type epoxy resins; Examples include benzopyran-type epoxy resins such as dibenzopyran, hexamethyldibenzopyran, and 7-phenylhexamethyldibenzopyran. Of these epoxy resins, so-called glycidyl ether type epoxy resins obtained by epoxidizing phenol compounds are preferred, and among these, novolac type epoxy resins, aralkyl type epoxy resins, and dicyclopentadiene type epoxy resins are more preferred from the viewpoint of dielectric properties. The above epoxy resins may be used individually or in combination of two or more types. 【0171】 The epoxy equivalent of the epoxy resin is preferably 120 to 400 g / eq, and more preferably 150 to 300 g / eq. A epoxy equivalent of 120 g / eq or more is preferred because it results in superior dielectric properties of the resulting cured product, while a epoxy equivalent of 400 g / eq or less is preferred because it provides an excellent balance between heat resistance and dielectric loss tangent of the resulting cured product. 【0172】 The softening point of the epoxy resin is preferably 20 to 200°C, and more preferably 40 to 150°C, from the viewpoint of improving light sensitivity, developability, heat resistance, adhesion, and elastic modulus in a balanced manner. 【0173】 The amine curing agent is not particularly limited, but examples include aliphatic amines such as diethylenetriamine (DTA), triethylenetetramine (TTA), tetraethylenepentamine (TEPA), diproprendiamine (DPDA), diethylaminopropylamine (DEAPA), N-aminoethylpiperazine, mensendiamine (MDA), isophoronediamine (IPDA), 1,3-bisaminomethylcyclohexane (1,3-BAC), piperidine, N,N,-dimethylpiperazine, and triethylenediamine; and aromatic amines such as m-xylenediamine (XDA), methanephenylenediamine (MPDA), diaminodiphenylmethane (DDM), diaminodiphenylsulfone (DDS), benzylmethylamine, 2-(dimethylaminomethyl)phenol, and 2,4,6-tris(dimethylaminomethyl)phenol. 【0174】 Examples of the acid anhydride curing agents include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenonetetracarboxylic anhydride, ethylene glycol bistrimellitate, glycerol trimellitate, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, methylbutenyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, succinic anhydride, and methylcyclohexendicarboxylic anhydride. 【0175】 Examples of the phenol resin curing agents include phenol novolac resin, cresol novolac resin, naphthol novolac resin, bisphenol novolac resin, biphenyl novolac resin, dicyclopentadiene-phenol addition type resin, phenol aralkyl resin, naphthol aralkyl resin, triphenolmethane type resin, tetraphenolethane type resin, aminotriazine modified phenol resin, and the like. The other curing agents mentioned above may be used individually or in combination of two or more. 【0176】 When using the curing agent described above, the curable resin composition of this embodiment preferably contains 10 to 40 parts by mass of the curing agent per 100 parts by mass of the resin having the acid group and polymerizable unsaturated group. If the amount is 10 parts by mass or more, the heat resistance and curability can be further improved, and if it is 40 parts by mass or less, a lower dielectric loss tangent and higher flexibility can be achieved. 【0177】 (Optional addition ingredient) The curable resin composition of this embodiment may further contain optional additives, as long as they do not deviate from the purpose. Examples of optional additives include curing accelerators, other resins, organic solvents, polymerization inhibitors, antioxidants, flame retardants, fillers, pigments, defoamers, viscosity modifiers, leveling agents, UV stabilizers, and storage stabilizers. 【0178】 --Curing accelerator-- The curing accelerator is not particularly limited, but examples include phosphorus-based curing accelerators, amine-based curing accelerators, imidazole-based curing accelerators, guanidine-based curing accelerators, urea-based curing accelerators, etc. The curing accelerator may be used alone or in combination of two or more types. 【0179】 Examples of the phosphorus-based curing accelerators include organophosphine compounds such as triphenylphosphine, tributylphosphine, triparathylphosphine, diphenylcyclohexylphosphine, and tricyclohexylphosphine; organophosphine compounds such as trimethylphosphine and triethylphosphine; and phosphonium salts such as ethyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, butylphosphonium tetraphenylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylphosphinetriphenylborane, tetraphenylphosphonium thiocyanate, tetraphenylphosphonium dicyanamide, butylphenylphosphonium dicyanamide, and tetrabutylphosphonium decanoate. 【0180】 Examples of the amine-based curing accelerators include triethylamine, tributylamine, N,N-dimethyl-4-aminopyridine (DMAP), 2,4,6-tris(dimethylaminomethyl)phenol, 1,8-diazabicyclo[5,4,0]-undecene-7 (DBU), and 1,5-diazabicyclo[4,3,0]-nonene-5 (DBN). 【0181】 The imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, and 1-cyanoethyl-2-ethyl-4-methylimidazole. Examples include ethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5 hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, and 2-methylimidazoline. 【0182】 Examples of the guanidine-based curing accelerators include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]deca-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]deca-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-butylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, and 1-phenylbiguanide. 【0183】 Examples of the urea-based curing accelerator include 3-phenyl-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, chlorophenylurea, 3-(4-chlorophenyl)-1,1-dimethylurea, and 3-(3,4-dichlorophenyl)-1,1-dimethylurea. 【0184】 Of the curing accelerators mentioned above, it is preferable to use 2-ethyl-4-methylimidazole or N,N-dimethyl-4-aminopyridine (DMAP). 【0185】 When using the curing accelerator, the content of the curing accelerator in the curable resin composition of this embodiment is preferably 0.01 to 5 parts by mass per 100 parts by mass of the resin having the acid group and polymerizable unsaturated group. If the content of the curing accelerator is 0.01 parts by mass or more, the curability can be more reliably improved. On the other hand, if the content of the curing accelerator is 5 parts by mass or less, the insulation reliability can be maintained at a sufficiently good level. From a similar viewpoint, the content of the curing accelerator is more preferably 0.1 parts by mass or more, and more preferably 5 parts by mass or less, per 100 parts by mass of the resin having the acid group and polymerizable unsaturated group. 【0186】 --Other resins-- The aforementioned other resins are not particularly limited, but include maleimide resins, polyphenylene ether resins, polyimide resins, cyanate ester resins, benzoxazine resins, triazine-containing cresol novolac resins, cyanate ester resins, styrene-maleic anhydride resins, allyl group-containing resins such as diallylbisphenol and triallyl isocyanurate, polyphosphate esters, and phosphate ester-carbonate copolymers. These other resins may be used individually or in combination of two or more. 【0187】 When using the aforementioned other resins, it is preferable that the content of the other resins in the curable resin composition of this embodiment is 50% by mass or less of the total. 【0188】 --Organic Solvents-- The organic solvent may have the function of adjusting the viscosity of the curable resin composition. Specific examples of organic solvents are not particularly limited, but include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ether solvents such as diethyl ether and tetrahydrofuran; ester solvents such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, and carbitol acetate; carbitols such as cellosolve and butyl carbitol; aromatic hydrocarbons such as toluene, xylene, ethylbenzene, mesitylene, 1,2,3-trimethylbenzene, and 1,2,4-trimethylbenzene; and amide solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone. The organic solvent may be used alone or in combination of two or more types. 【0189】 When using the aforementioned organic solvent, the content of the organic solvent in the curable resin composition of this embodiment is preferably 90% by mass or less, more preferably 10 to 90% by mass, and even more preferably 20 to 80% by mass, based on the total amount (100% by mass) of the curable resin composition. An organic solvent content of 10% by mass or more is preferable because it provides excellent handling properties. On the other hand, an organic solvent content of 90% by mass or less is preferable from an economic standpoint. 【0190】 --Polymerization inhibitor-- The polymerization inhibitor is not particularly limited, but may include p-methoxyphenol (methoquinone), p-methoxycresol, 4-methoxy-1-naphthol, 4,4'-dialkoxy-2,2'-bi-1-naphthol, 3-(N-salicyroyl)amino-1,2,4-triazole, N'1,N'12-bis(2-hydroxybenzoyl)dodecanedihydrazide, styrene-phenol, N-isopropyl-N'-phenylbenzene-1,4-diamine, 6-ethoxy-2,2,4- Phenolic compounds such as trimethyl-1,2-dihydroquinoline; quinone compounds such as hydroquinone, methylhydroquinone, p-benzoquinone, methyl-p-benzoquinone, 2,5-diphenylbenzoquinone, 2-hydroxy-1,4-naphthoquinone, anthraquinone, and diphenoquinone; melamine, p-phenylenediamine, 4-aminodiphenylamine, N,N'-diphenyl-p-phenylenediamine, Ni-propyl-N'-phenyl-p-phenylenediamine, N-(1.Amine compounds such as 3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, diphenylamine, 4,4'-dicumyl-diphenylamine, 4,4'-dioctyl-diphenylamine, poly(2,2,4-trimethyl-1,2-dihydroquinoline), styrene-diphenylamine, reaction products of styrene-diphenylamine and 2,4,4-trimethylpentene, reaction products of diphenylamine and 2,4,4-trimethylpentene; phenothiazine, distearylthiodipropionate, 2,2-bis({[3-(dodecyl Thioether compounds such as ruthio)propionyl]oxy}methyl)-1,3-propanediyl=bis[3-(dodecylthio)propionate], ditridecane-1-yl=3,3'-sulfandiyldipropanoate; N-nitrosodiphenylamine, N-nitrosophenylnaphthylamine, p-nitrosophenol, nitrosobenzene, p-nitrosodiphenylamine, α-nitroso-β-naphthol, N,N-dimethylp-nitrosoaniline, p-nitrosodiphenylamine, p-nitronedimethylamine, p-nitrone -N,N-diethylamine, N-nitrosoethanolamine, N-nitrosodi-n-butylamine, N-nitroso-Nn-butyl-4-butanolamine, N-nitroso-diisopropanolamine, N-nitroso-N-ethyl-4-butanolamine, 5-nitroso-8-hydroxyquinoline, N-nitrosomorpholine, N-nitroso-N-phenylhydroxylamine ammonium salt, nitrosobenzene, N-nitroso-N-methyl-p-toluenesulfonamide, N-nitroso-N-ethylurethane, N-nitroso-Nn Nitroso compounds such as propyl urethane, 1-nitroso-2-naphthol, 2-nitroso-1-naphthol, 1-nitroso-2-naphthol-3,6-sulfonate sodium, 2-nitroso-1-naphthol-4-sulfonate sodium, 2-nitroso-5-methylaminophenol hydrochloride, 2-nitroso-5-methylaminophenol hydrochloride; esters of phosphoric acid and octadecane-1-ol, triphenyl phosphite, 3,9-dioctadecane-1-yl-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5] Phosphate compounds such as undecane, trisnonylphenyl phosphite, phosphite-(1-methylethylidene)-di-4,1-phenylenetetra-C12-15-alkyl ester, 2-ethylhexyl=diphenyl=phosphite, diphenylisodecyl phosphite, triisodecyl=phosphite, and tris(2,4-di-tert-butylphenyl) phosphite; bis(dimethyldithiocarbamato-κ(2)S,S')zinc, and diethyldithiocarbamate zinc Examples include zinc compounds such as zinc dibutyldithiocarbamate; nickel compounds such as bis(N,N-dibutylcarbamodithioato-S,S')nickel; and sulfur compounds such as 1,3-dihydro-2H-benzimidazole-2-thione, 4,6-bis(octylthiomethyl)-o-cresol, 2-methyl-4,6-bis[(octan-1-ylsulfanyl)methyl]phenol, dilaurylthiodipropionate, and 3,3'-distearyl thiodipropionate. The polymerization inhibitors may be used individually or in combination of two or more. 【0191】 --Antioxidant-- The antioxidant is not particularly limited, but compounds similar to those exemplified as polymerization inhibitors can be used. The antioxidant may be used alone or in combination of two or more. 【0192】 Examples of commercially available polymerization inhibitors and antioxidants include "Q-1300" and "Q-1301" manufactured by Wako Pure Chemical Industries, Ltd., and "Sumiriser BBM-S" and "Sumiriser GA-80" manufactured by Sumitomo Chemical Co., Ltd. 【0193】 --Flame retardant-- The aforementioned flame retardant is not particularly limited, but examples include inorganic phosphorus-based flame retardants, organophosphorus-based flame retardants, halogen-based flame retardants, etc. The flame retardant may be used alone or in combination of two or more types. 【0194】 The inorganic phosphorus-based flame retardant is not particularly limited, but examples include red phosphorus; ammonium phosphates such as monoammonium phosphate, diammonium phosphate, triammonium phosphate, and polyammonium phosphate; and phosphate amides. 【0195】 The organophosphorus flame retardants mentioned above are not particularly limited, but include methyl acid phosphate, ethyl acid phosphate, isopropyl acid phosphate, dibutyl phosphate, monobutyl phosphate, butoxyethyl acid phosphate, 2-ethylhexyl acid phosphate, bis(2-ethylhexyl) phosphate, monoisodecyl acid phosphate, lauryl acid phosphate, tridecyl acid phosphate, and stearyl acid phosphate. Phosphate esters such as isostearyl acid phosphate, oleyl acid phosphate, butyl pyrophosphate, tetracosyl acid phosphate, ethylene glycol acid phosphate, and (2-hydroxyethyl) methacrylate acid phosphate; diphenylphosphine such as 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and diphenylphosphine oxide; and 10-(2,5-dihydroxyphenyl)-10H-9-oxa Phosphorus-containing phenols such as -10-phosphaphenanthrene-10-oxide, 10-(1,4-dioxynaphthalene)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, diphenylphosphinnylhydroquinone, diphenylphosphenyl-1,4-dioxynaphthalene, 1,4-cyclooctylenephosphinnyl-1,4-phenyldiol, and 1,5-cyclooctylenephosphinnyl-1,4-phenyldiol; 9,10-dihydro-9-oxa-10-phos Examples include cyclic phosphorus compounds such as phaphenanthrene-10-oxide, 10-(2,5-dihydrooxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, and 10-(2,7-dihydrooxynaphthyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide; and compounds obtained by reacting the aforementioned phosphate esters, diphenylphosphine, or phosphorus-containing phenols with epoxy resins, aldehyde compounds, or phenolic compounds. 【0196】 The halogenated flame retardant is not particularly limited, but examples include brominated polystyrene, bis(pentabromophenyl)ethane, tetrabromobisphenol A bis(dibromopropyl ether), 1,2-bis(tetrabromophthalimide), 2,4,6-tris(2,4,6-tribromophenoxy)-1,3,5-triazine, and tetrabromophthalic acid. 【0197】 When using the aforementioned flame retardant, the amount of flame retardant used in the resin composition of this embodiment is preferably 0.1 to 50 parts by mass per 100 parts by mass of the resin having the acid group and polymerizable unsaturated group. If the flame retardant content is 0.1 parts by mass or more, flame retardancy can be imparted more reliably. On the other hand, if the flame retardant content is 50 parts by mass or less, flame retardancy can be imparted while maintaining dielectric properties. From a similar viewpoint, the flame retardant content is more preferably 1 part by mass or more, and more preferably 30 parts by mass or less, per 100 parts by mass of the resin having the acid group and polymerizable unsaturated group. 【0198】 <Filler> Examples of fillers include organic fillers and inorganic fillers. Organic fillers have functions such as improving elongation and improving mechanical strength. Inorganic fillers have functions such as reducing the coefficient of thermal expansion and providing flame retardancy. The above-mentioned fillers may be used individually or in combination of two or more types. 【0199】 The aforementioned organic filler is not particularly limited, but examples include polyamide particles. 【0200】 The inorganic filler is not particularly limited, but examples include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, zirconium tungstate phosphate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, carbon black, etc. Of these, silica is preferred. In this case, amorphous silica, fused silica, crystalline silica, synthetic silica, hollow silica, etc. can be used as silica. 【0201】 Furthermore, the filler may be surface-treated as needed. In this case, there are no particular limitations on the surface treatment agents that can be used, but aminosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, silane coupling agents, organosilazane compounds, titanate coupling agents, etc. Specific examples of surface treatment agents include 3-glycidoxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, hexamethyldisilazane, etc. The above-mentioned fillers may be used individually or in combination of two or more types. 【0202】 When using the filler described above, the amount of filler used in the curable resin composition of this embodiment is preferably 0.5 to 95 parts by mass per 100 parts by mass of the resin having the acid group and polymerizable unsaturated group. If the filler content is 0.5 parts by mass or more, the effect of the filler can be sufficiently imparted. On the other hand, if the filler content is 95 parts by mass or less, deterioration of moldability due to increased viscosity of the compound can be suppressed. From a similar viewpoint, the filler content is more preferably 5 parts by mass or more, and more preferably 80 parts by mass or less, per 100 parts by mass of the resin having the acid group and polymerizable unsaturated group. 【0203】 The method for producing the curable resin composition of this embodiment is not particularly limited, and it can be produced by kneading the various components described above using a kneader such as a roll. 【0204】 <Cured product> The cured product of this embodiment is characterized by being obtained by curing the above-described curable resin composition. The cured product of this embodiment has high heat resistance, high adhesion, and excellent dielectric properties, and can function suitably as an insulating material or a resist member. The cured product of this embodiment is preferably obtained by curing a curable resin composition by irradiating it with active energy rays. 【0205】 Examples of the active energy rays include ionizing radiation such as ultraviolet rays, electron beams, alpha rays, beta rays, and gamma rays. When ultraviolet rays are used as the active energy rays, irradiation may be carried out under an inert gas atmosphere such as nitrogen gas, or under an air atmosphere, in order to efficiently carry out the curing reaction by ultraviolet rays. 【0206】 Specific sources of ultraviolet light include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, gallium lamps, metal halide lamps, and other ultraviolet lamps, as well as sunlight and LEDs. Among these, ultraviolet lamps are generally used from the standpoint of practicality and economic efficiency. 【0207】 The integrated light quantity of the active energy rays is not particularly limited, but is preferably 0.1 to 50 kJ / m 2 and more preferably 0.5 to 10 kJ / m 2 . When the integrated light quantity is within the above range, generation or suppression of uncured portions can be sufficiently achieved. Note that irradiation of the active energy rays may be performed in one step or may be divided into two or more steps. 【0208】 Also, as another method for obtaining a cured product by subjecting the curable resin composition to a curing reaction, for example, heat curing may be mentioned. The heating temperature during heat curing is not particularly limited, but is 100 to 300 °C, and the heating time is preferably 1 to 24 hours. 【0209】 Applications in which the curable resin composition or cured product of the present embodiment is used include insulating materials for circuit boards such as printed wiring board materials, resin compositions for flexible wiring boards, interlayer insulating materials for build-up boards, adhesive films for build-up, resin casting materials, adhesives, semiconductor encapsulation materials, semiconductor devices, prepregs, conductive pastes, build-up films, build-up boards, fiber reinforced composite materials, molded products obtained by curing the above composite materials, and the like. Among these various applications, in the applications of printed wiring board materials, insulating materials for circuit boards, and adhesive films for build-up, they can be used as insulating materials for so-called substrates with built-in electronic components in which passive components such as capacitors and active components such as IC chips are embedded in the substrate. Furthermore, among the above, taking advantage of the characteristics that the cured product has excellent heat resistance, adhesion, and low dielectric characteristics, the curable resin composition or cured product of the present embodiment can be suitably applied to semiconductor encapsulation materials, semiconductor devices, prepregs, flexible wiring boards, circuit boards, and build-up films, build-up boards, multilayer printed wiring boards, fiber reinforced composite materials, and molded products obtained by curing the above composite materials. 【0210】 <Insulating Material> The insulating material of this embodiment is characterized by comprising the curable resin composition described above. Furthermore, it is preferable that the insulating material of this embodiment is obtained by curing the curable resin composition described above by irradiation with active energy rays. The insulating material of this embodiment exhibits excellent heat resistance, adhesion, and elongation. 【0211】 Examples of insulating materials include the interlayer insulating material for build-up substrates, insulating materials for circuit boards such as build-up adhesive films, insulating materials for circuit boards, and insulating materials for substrates for embedding electronic components. For example, a method for manufacturing a build-up substrate from the above-mentioned curable resin composition is a method consisting of the following three steps. The first step is to apply the curable resin composition, which is appropriately blended with rubber, fillers, etc., to a circuit board with a circuit formed on it using a spray coating method, a curtain coating method, etc., and then cure it. The second step is to then drill holes such as predetermined through-holes as needed, treat the surface with a roughening agent, wash the surface with hot water to form irregularities, and then plate it with a metal such as copper. The third step is to repeat these operations sequentially as desired to alternately build up and form a resin insulating layer and a conductor layer of a predetermined circuit pattern. It is preferable to drill the through-holes after the formation of the outermost resin insulating layer. The first step can be carried out not only by the solution coating method described above, but also by laminating a build-up film that has been pre-coated to a desired thickness and dried. Furthermore, the build-up substrate of the present invention can also be manufactured by forming a roughened surface and omitting the plating process by heating and pressing a resin-coated copper foil, on which the resin composition has been semi-cured, onto a wiring board on which a circuit has been formed, at 170-250°C. 【0212】 <Resist material> The resist member of this embodiment is characterized by being made of the curable resin composition described above. The resist member can be obtained, for example, by coating the curable resin composition described above onto a substrate, drying it in a suitable temperature range of about 60 to 100°C, exposing it with active energy rays through a photomask on which a desired pattern has been formed, developing the unexposed areas with an alkaline aqueous solution, and further heating and curing it in a temperature range of about 140 to 180°C. The resist member (resist film) of this embodiment has excellent heat resistance, adhesion, and dielectric properties. [Examples] 【0213】 The present invention will be described in more detail below with reference to examples, but the present invention is not limited in any way to the following examples. 【0214】 (Synthesis Example 1: Synthesis of Styrene-Modified Phenolic Resin (1)) In a flask equipped with a thermometer, dropping funnel, condenser, fractionation column, nitrogen gas inlet tube, and stirrer, 186.2 parts by mass (1.0 mol) of 4,4'-dihydroxybiphenyl and 208.3 parts by mass of toluene were charged, and 4.2 parts by mass of p-toluenesulfonic acid were added. The temperature was raised to 110°C. 416.6 parts by mass (4.0 mol) of styrene were added dropwise over 2 hours, and the reaction was continued at 110°C for 2 hours. After the reaction was complete, the temperature was lowered to 80°C and neutralized with an aqueous NaOH solution. Toluene was removed under reduced pressure and heating to obtain 542.5 g of styrene-modified phenolic resin (1). The obtained styrene-modified phenolic resin (1) was solid in appearance, and its hydroxyl group equivalent was 316 g / equivalent. 【0215】 (Synthesis Example 2 [Synthesis of epoxy resin (A-1)]) In a flask equipped with a thermometer, dropping funnel, condenser, fractionation column, nitrogen gas inlet tube, and stirrer, 316.0 parts by mass of styrene-modified phenol resin (1) obtained in Synthesis Example 1 (1.0 equivalent of hydroxyl groups), 740.0 parts by mass of epichlorohydrin (8.0 equivalents), and 158.0 parts by mass of n-butanol were charged and dissolved while purging with nitrogen gas. After raising the temperature to 60°C, 220.0 parts by mass of 20% sodium hydroxide aqueous solution (1.1 equivalents) was added dropwise over 5 hours. Stirring was then continued under the same conditions for 0.5 hours. Subsequently, the unreacted epichlorohydrin was removed by vacuum distillation. 744.0 parts by mass of methyl isobutyl ketone was added to the resulting crude epoxy resin and dissolved. Furthermore, 5.0 parts by mass of a 20% sodium hydroxide aqueous solution was added to this solution and reacted at 80°C for 2 hours. The mixture was then washed three times with 372.0 parts by mass of water until the pH of the washing solution became neutral. Next, the system was dehydrated by azeotrope, and after microfiltration, the solvent was removed under reduced pressure to obtain 334.9 parts by mass of epoxy resin (A-1). The melt viscosity of the obtained epoxy resin (A-1) (measurement method: ICI viscometer, measurement temperature: 150°C) was 1.1 dPa·s, the softening point was 72°C, and the epoxy equivalent was 384 g / equivalent. 【0216】 (Synthesis Example 3: Synthesis of Styrene-Modified Phenolic Resin (2)) The same procedure as in Synthesis Example 1 was followed, except that the amount of styrene was changed to 208.3 parts by mass (2.0 moles), to obtain 374.8 parts by mass of styrene-modified phenolic resin (2). The obtained styrene-modified phenolic resin (2) was solid in appearance, and its hydroxyl group equivalent was 187 g / equivalent. 【0217】 (Synthesis Example 4 [Synthesis of epoxy resin (A-2)]) In a flask equipped with a thermometer, dropping funnel, condenser, fractionation tube, nitrogen gas inlet tube, and stirrer, 187.0 parts by mass of styrene-modified phenol resin (2) obtained in Synthesis Example 3 (1.0 equivalent of hydroxyl groups), 740.0 parts by mass of epichlorohydrin (8.0 equivalents), and 158.0 parts by mass of n-butanol were charged and dissolved while purging with nitrogen gas. After raising the temperature to 60°C, 220.0 parts by mass of 20% sodium hydroxide aqueous solution (1.1 equivalents) was added dropwise over 5 hours. Stirring was then continued under the same conditions for 0.5 hours. Subsequently, the unreacted epichlorohydrin was removed by vacuum distillation. 486.0 parts by mass of methyl isobutyl ketone was added to the resulting crude epoxy resin and dissolved. Furthermore, 5.0 parts by mass of a 20% sodium hydroxide aqueous solution was added to this solution and reacted at 80°C for 2 hours. The mixture was then washed three times with 243.0 parts by mass of water until the pH of the washing solution became neutral. Next, the system was dehydrated by azeotrope, and after microfiltration, the solvent was removed under reduced pressure to obtain 228.4 parts by mass of epoxy resin (A-2). The melt viscosity of the obtained epoxy resin (2) (measurement method: ICI viscometer, measurement temperature: 150°C) was 0.7 dPa·s, the softening point was 107°C, and the epoxy equivalent was 267 g / equivalent. 【0218】 (Synthesis Example 5 [Synthesis of epoxy resin (3)]) The same procedure as in Synthesis Example 1 was followed, except that the amount of styrene was changed to 104.2 parts by mass (1.0 mol), to obtain 278.4 parts by mass of phenol resin (3). The hydroxyl group equivalent of the obtained styrene-modified phenol resin (3) was 145 g / equivalent. In a flask equipped with a thermometer, dropping funnel, condenser, fractionation tube, nitrogen gas inlet tube, and stirrer, 145.0 parts by mass of the obtained styrene-modified phenolic resin (3) (1.0 equivalent of hydroxyl groups), 740.0 parts by mass of epichlorohydrin (8.0 equivalents), and 158.0 parts by mass of n-butanol were charged and dissolved while purging with nitrogen gas. After raising the temperature to 60°C, 220.0 parts by mass of 20% sodium hydroxide aqueous solution (1.1 equivalents) was added dropwise over 5 hours. Stirring was then continued under the same conditions for 0.5 hours. Subsequently, the unreacted epichlorohydrin was removed by vacuum distillation. 402.0 parts by mass of methyl isobutyl ketone was added to the resulting crude epoxy resin and dissolved. Furthermore, 5.0 parts by mass of a 20% sodium hydroxide aqueous solution was added to this solution and reacted at 80°C for 2 hours. The mixture was then washed three times with 201.0 parts by mass of water until the pH of the washing solution became neutral. Next, the system was dehydrated by azeotrope, and after microfiltration, the solvent was removed under reduced pressure to obtain 192.9 parts by mass of epoxy resin (3). The melt viscosity of the obtained epoxy resin (3) (measurement method: ICI viscometer, measurement temperature: 150°C) was 0.3 dPa·s, the softening point was 109°C, and the epoxy equivalent was 231 g / equivalent. 【0219】 (Synthesis Example 6: Synthesis of a resin (D-1) having acidic groups and polymerizable unsaturated groups) In a flask equipped with a thermometer, stirrer, and reflux condenser, 123 parts by mass of diethylene glycol monoethyl ether acetate was added, and 214 parts by mass of orthocresol novolac type epoxy resin "EPICLON N-680" (manufactured by DIC Corporation, softening point 86°C, epoxy equivalent: 214 g / eq) was dissolved. After adding 0.9 parts by mass of dibutylhydroxytoluene and 0.2 parts by mass of methoquinone, 72 parts by mass of acrylic acid and 1.4 parts by mass of triphenylphosphine were added, and the reaction was carried out at 120°C for 10 hours while blowing in air. Next, 72 parts by mass of diethylene glycol monoethyl ether acetate and 76 parts by mass of tetrahydrophthalic anhydride were added, and the reaction was carried out at 110°C for 3 hours to obtain a resin (D-1) having acidic groups and polymerizable unsaturated groups. The nonvolatile content of this resin (D-1) having acidic groups and polymerizable unsaturated groups was 65% by mass, and the solid content acid value was 80 mgKOH / g. The acid value was measured based on the neutralization titration method specified in JIS K 0070 (1992). 【0220】 (Example 1: Resin having acidic groups and polymerizable unsaturated groups (B-1)) In a flask equipped with a thermometer, stirrer, and reflux condenser, 195.4 parts by mass of diethylene glycol monoethyl ether acetate was added, and 384 parts by mass of epoxy resin (A-1) obtained in Synthesis Example 2 were dissolved. After adding 1.1 parts by mass of dibutylhydroxytoluene and 0.2 parts by mass of methoquinone, 72 parts by mass of acrylic acid and 2.3 parts by mass of triphenylphosphine were added, and the reaction was carried out at 120°C for 10 hours while blowing in air. Next, 115.6 parts by mass of diethylene glycol monoethyl ether acetate and 121.6 parts by mass of tetrahydrophthalic anhydride were added, and the reaction was carried out at 110°C for 3 hours to obtain resin (B-1) having acidic groups and polymerizable unsaturated groups. The nonvolatile content of this resin (B-1) having acidic groups and polymerizable unsaturated groups was 65% by mass, and the solid content acid value was 80 mgKOH / g. 【0221】 (Example 2: Resin having acidic groups and polymerizable unsaturated groups (B-2)) In a flask equipped with a thermometer, stirrer, and reflux condenser, 145.3 parts by mass of diethylene glycol monoethyl ether acetate was added, and 267 parts by mass of epoxy resin (A-2) obtained in Synthesis Example 4 were dissolved. After adding 0.8 parts by mass of dibutylhydroxytoluene and 0.2 parts by mass of methoquinone, 72 parts by mass of acrylic acid and 1.7 parts by mass of triphenylphosphine were added, and the reaction was carried out at 120°C for 12 hours while blowing in air. Next, 86.4 parts by mass of diethylene glycol monoethyl ether acetate and 91.2 parts by mass of tetrahydrophthalic anhydride were added, and the reaction was carried out at 110°C for 3 hours to obtain resin (B-2) having acidic groups and polymerizable unsaturated groups. The nonvolatile content of this resin (B-2) having acidic groups and polymerizable unsaturated groups was 65% by mass, and the solid content acid value was 81 mgKOH / g. 【0222】 (Comparative Example 1: Resin having acidic groups and polymerizable unsaturated groups (C-1)) In a flask equipped with a thermometer, stirrer, and reflux condenser, 129.9 parts by mass of diethylene glycol monoethyl ether acetate was added, and 231 parts by mass of epoxy resin (3) obtained in Synthesis Example 5 were dissolved. After adding 0.8 parts by mass of dibutylhydroxytoluene and 0.2 parts by mass of methoquinone, 72 parts by mass of acrylic acid and 1.5 parts by mass of triphenylphosphine were added, and the reaction was carried out at 120°C for 13 hours while blowing in air. Next, 76.7 parts by mass of diethylene glycol monoethyl ether acetate and 80.6 parts by mass of tetrahydrophthalic anhydride were added, and the reaction was carried out at 110°C for 3 hours to obtain resin (C-1) having acidic groups and polymerizable unsaturated groups. The nonvolatile content of this resin (C-1) having acidic groups and polymerizable unsaturated groups was 65% by mass, and the solid content acid value was 80 mgKOH / g. 【0223】 (Examples 3-8, Comparative Examples 2-3) The components listed in Tables 1 and 2 below were mixed to obtain curable resin compositions (1), (2), (3), (C1), and (C2). The following tests were performed on these curable resin compositions. 【0224】 [Evaluation of alkaline developability] The curable resin compositions obtained in each of the examples and comparative examples were applied onto a glass substrate using an applicator so as to have a film thickness of 50 μm, and then dried at 80°C for 50 minutes, 60 minutes, 70 minutes, 80 minutes, 90 minutes, 100 minutes, and 110 minutes respectively to prepare samples with different drying times. These were developed with a 1% by mass aqueous sodium carbonate solution (alkaline aqueous solution) at 30°C for 180 seconds, and the drying time at 80°C of the samples with no residue remaining on the substrate was evaluated as the drying control width (minutes). The longer the drying control width (minutes), the higher the developability. 【0225】 [Elasticity evaluation method] The evaluation of elasticity was performed by measuring the elastic modulus through a tensile test. The curable resin compositions obtained in each of the examples and comparative examples were applied onto a copper foil (manufactured by Furukawa Electric Co., Ltd., electrolytic copper foil "F2-WS" 18 μm) using an applicator so as to have a film thickness of 50 μm, and dried at 80°C for 30 minutes. Next, after irradiating ultraviolet rays of 10 kJ / m 2 using a metal halide lamp, it was heated at 160°C for 1 hour to obtain a cured coating film. Next, the cured coating film was peeled off from the copper foil to obtain a cured product (test piece 1). 【0226】 [Tensile test] The test piece 1 was cut into a size of 10 mm × 80 mm, and a tensile test of the test piece was performed under the following measurement conditions using a precision universal testing machine Autograph "AG-IS" manufactured by Shimadzu Corporation. The elastic modulus (MPa) until the test piece broke was measured and evaluated according to the following criteria. 【0227】 Measurement conditions: temperature 23°C, humidity 50%, distance between gauge marks 20 mm, distance between fulcrums 20 mm, tensile speed 10 mm / min 【0228】 [Dielectric constant measurement method] The curable resin compositions obtained in each of the examples and comparative examples were applied onto a glass substrate using an applicator so as to have a film thickness of 50 μm, and dried at 80°C for 30 minutes. Next, after irradiating ultraviolet rays of 10 kJ / m 2After irradiation with ultraviolet light, the material was heated at 160°C for 1 hour to obtain a cured coating. Next, the cured coating was peeled off the glass substrate to obtain a cured product. Then, the product was stored in a room at 23°C and 50% humidity for 24 hours to obtain a test specimen, and the dielectric constant of the test specimen at 1 GHz was measured using the cavity resonance method with an Agilent Technologies Network Analyzer E8362C. 【0229】 [Method for measuring dielectric loss tangent] The curable resin compositions obtained in each example and comparative example were applied to a glass substrate to a thickness of 50 μm using an applicator and dried at 80°C for 30 minutes. Then, a metal halide lamp was used to measure 10 kJ / m³. 2 After irradiation with ultraviolet light, the material was heated at 160°C for 1 hour to obtain a cured coating. Next, the cured coating was peeled off the glass substrate to obtain a cured product. Then, a test specimen was stored in a room at 23°C and 50% humidity for 24 hours, and the dielectric loss tangent of the test specimen at 1 GHz was measured using the cavity resonance method with an Agilent Technologies, Inc. Network Analyzer E8362C. 【0230】 [Method for evaluating adhesion] Adhesion was evaluated by measuring the peel strength. 【0231】 <Preparation of Test Specimen 2> The curable resin compositions obtained in the examples and comparative examples were applied to copper foil (Furukawa Sangyo Co., Ltd., electrolytic copper foil "F2-WS" 18 μm) using a 50 μm applicator, and then dried at 80°C / 30 min, with a metal halide lamp curing at 10 kJ / m². 2 After irradiating with ultraviolet light, the specimen was heated at 160°C for 1 hour to obtain specimen 2. 【0232】 <Method for measuring peel strength> The aforementioned test piece 2 was cut to a size of 1 cm in width and 12 cm in length, and the 90° peel strength was measured using a peel tester (A&D Tensilon, manufactured by A&D Corporation, peel speed 50 mm / min). 【0233】 The measurement conditions for peel strength are as follows: Measuring instrument: "A&D Tensilon" manufactured by A&D Corporation. Test specimen: 1 cm wide, 12 cm long. Peel test machine. Test speed: 50 mm / min Conditions: Temperature 23℃, humidity 50% 【0234】 [Table 1] 【0235】 [Table 2] 【0236】 The following were used in Tables 1 and 2. Hardener: DIC Corporation, product name "EPICLON N-680" Organic solvent: Diethylene glycol monoethyl ether acetate Photopolymerization initiator: Omnirad-907, manufactured by IGM Resins. 【0237】 From the results in Tables 1 and 2, it can be seen that the cured products obtained by curing the curable resin compositions of Examples 3 to 8, which use resins having acid groups and polymerizable unsaturated groups according to the present invention, have a lower elastic modulus, exhibit lower dielectric properties, and have higher adhesion compared to the cured products of Comparative Examples 2 and 3, which use conventional resins having acid groups and polymerizable unsaturated groups. [Industrial applicability] 【0238】 The resin, curable resin composition, and cured product having acidic groups and polymerizable unsaturated groups of the present invention can be used as insulating materials, resist members, and the like.

Claims

[Claim 1] An epoxy resin (A), an unsaturated monobasic acid (B), and a polybasic acid anhydride (C) are essential raw materials, and the resin has acidic groups and polymerizable unsaturated groups. The epoxy resin (A) is obtained by reacting 1 mole of dihydroxybiphenyl with 1.5 to 8 moles of styrene to a reaction product and an epihalohydrin, and is a resin having acidic groups and polymerizable unsaturated groups, represented by the following general formula (1). 【Chemistry 1】 (However, in the above general formula (1), R １ and R ２ (where 'p' represents an α-methylbenzyl group, and 'G' represents a glycidyl group. p and q independently represent numbers from 0 to 4, and p + q has an average value of 1.5 to 8. Also, n represents a number from 0 to 5.) [Claim 2] A curable resin composition characterized by comprising a resin having an acid group and a polymerizable unsaturated group as described in claim 1. [Claim 3] Furthermore, the curable resin composition according to claim 2, comprising a photopolymerization initiator. [Claim 4] Furthermore, the curable resin composition according to claim 2, further comprising a resin (D) having acid groups and polymerizable unsaturated groups other than the resin having acid groups and polymerizable unsaturated groups. [Claim 5] Furthermore, the curable resin composition according to claim 2, further comprising a curing agent. [Claim 6] A cured product characterized by being obtained by curing a curable resin composition according to any one of claims 2 to 5. [Claim 7] An insulating material characterized by comprising the curable resin composition described in any one of claims 2 to 5. [Claim 8] A resist member characterized by comprising the curable resin composition described in any one of claims 2 to 5.

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