Composition, cured product, method for producing the cured product, and additives

Abstract

The main problem addressed by the present disclosure is to provide a composition having an excellent balance between curability and the heat resistance of a cured product. The present disclosure solves the problem by providing a composition that includes a compound represented by general formula (A1), a metal inactivating agent, and a curable component. The metal inactivating agent preferably includes at least one of a benzotriazole compound, a hydrazide compound, a salicylic acid compound, and a triazine compound. (See the specification for R101, R102, R103, R104, n, a1, and X in the formula.)

Description

[Technical Field]

[0001] This disclosure relates to compositions, cured products, methods for producing cured products, and additives. [Background technology]

[0002] Printed circuit boards have insulating films, such as solder resist films, formed on them for wiring protection. Solder resist films require improved heat resistance due to contact with solder, light irradiation from a light source, and thermal history caused by heat generation. Patent Document 1 describes the use of a curable composition containing a compound having a phenol skeleton and an amide bond, such as N'1,N'12-bis(2-hydroxybenzoyl)dodecanedihydrazide, which is known as a metal deactivator. The same document states that the curable composition described in the document can form a solder resist film with excellent heat resistance. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2019-191303 [Overview of the project]

[0004] However, curable compositions containing metal deactivators, such as those described in Patent Document 1, have drawbacks, such as the inability to obtain sufficiently heat-resistant cured products, and the possibility of color changes in the cured products under high-temperature conditions. Furthermore, the inventors considered using a conventionally known antioxidant in combination with a metal deactivator to improve heat resistance, but encountered problems such as insufficient heat resistance and insufficient curing properties.

[0005] This disclosure has been made in view of the above-mentioned problems, and its main objective is to provide a composition that has an excellent balance between curability and the heat resistance of the cured product.

[0006] As a result of diligent research to solve the above problems, the present inventors have found that by using a compound with a specific structure in which a phenolic hydroxyl group is protected by a protecting group as an antioxidant, in combination with a metal deactivator, excellent curability can be achieved and a cured product with excellent heat resistance can be obtained. Based on these findings, the inventors have completed the present invention.

[0007] In other words, this disclosure provides a composition comprising a compound represented by the following general formula (A1) (hereinafter sometimes referred to as compound A), a metal deactivator, and a curable component.

[0008] [ka]

[0009] (In the formula, R 101 This represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or an unsubstituted or substituted silyl group having 0 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, an unsubstituted or substituted heterocyclic-containing group, or an unsubstituted or substituted silyl group are replaced by a divalent group selected from group I below. R 102 and R 103 Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted. R 104represents a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, or an unsubstituted or substituted heterocyclic ring-containing group having 2 to 40 carbon atoms, or represents a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, or an unsubstituted or substituted heterocyclic ring-containing group are replaced by a divalent group selected from the following Group I, R 104 When there are a plurality of 104 Rs, the plurality of Rs R 104 may be bonded to each other to form a benzene ring or a naphthalene ring, 104 When there are a plurality of Rs, the plurality of Rs may be the same or different from each other, n represents an integer from 1 to 10, a1 represents an integer from 0 to 2, When n is from 2 to 10, the plurality of 101 Rs, 102 Rs, 103 Rs, 104 Rs and a1 may be the same or different from each other. X represents an n-valent group. )

[0010] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 230 -, -NR 230 -CO-, -CO-NR 230 -, -NR 230 -COO-, -OCO-NR 230 - or -SiR 230 R 231 -. R 230 and R 231 each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 40 carbon atoms. According to the present disclosure, the above composition has an excellent balance between curability and heat resistance of the cured product.

[0011] In this disclosure, R 101 However, the methylene group at the oxygen atom end of the group selected from unsubstituted or substituted aliphatic hydrocarbon groups, unsubstituted or substituted aromatic hydrocarbon-containing groups, and unsubstituted or substituted heterocyclic-containing groups is -COO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR from group I. 230 -, -NR 230 -CO-, -CO-NR 230 -, -NR 230 -COO- and -SiR 230 R 231 It is preferable that the group has 1 to 40 carbon atoms replaced by a divalent group selected from the above, or that it is a silyl group having 0 to 40 carbon atoms that is unsubstituted or substituted. 101 However, because it is the aforementioned base, it has an excellent balance between curability and the heat resistance of the cured product.

[0012] In this disclosure, it is preferable that the metal deactivator comprises at least one of a benzotriazole compound, a hydrazide compound, a salicylic acid compound, and a triazine compound. This is because the composition exhibits an even better balance between curability and the heat resistance of the cured product.

[0013] In this disclosure, it is preferable that the content of the metal deactivator is 5 parts by mass or more and 90 parts by mass or less in a total of 100 parts by mass of the compound represented by the general formula (A1) and the metal deactivator. This is because the balance between curability and the heat resistance of the cured product is further improved when the content of the metal deactivator is within the above range.

[0014] In this disclosure, it is preferable that the total content of the compound represented by the general formula (A1) and the metal deactivator is 0.01 parts by mass or more and 10 parts by mass or less in 100 parts by mass of the total of the compound represented by the general formula (A1), the metal deactivator, and the curable component. This is because having the total content of the compound represented by the general formula (A1) and the metal deactivator within the above range results in an even better balance between curability and the heat resistance of the cured product.

[0015] In this disclosure, it is preferable that the curable component includes both a radical polymerizable compound and a thermosetting compound. This is because including both a radical polymerizable compound and a thermosetting compound in the curable component results in an even better balance between curability and the heat resistance of the cured product.

[0016] The compositions disclosed herein are preferable for use as solder resists, as this provides particularly high technical significance for the effects of the present invention, namely, excellent heat resistance and curability.

[0017] This disclosure provides a cured product obtained by curing the above-described composition.

[0018] According to this disclosure, because the above-described composition is used, the product has excellent heat resistance.

[0019] This disclosure provides a method for producing a cured product, comprising a curing step for curing the above-described composition.

[0020] According to this disclosure, since the above-described composition is used, a cured product with excellent heat resistance can be easily obtained.

[0021] This disclosure provides an additive comprising a compound represented by the following general formula (A1) and a metal deactivator.

[0022] [ka]

[0023] (In the formula, R 101This represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or an unsubstituted or substituted silyl group having 0 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, an unsubstituted or substituted heterocyclic-containing group, or an unsubstituted or substituted silyl group are replaced by a divalent group selected from group I below. R 102 and R 103 Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted. R 104 This represents a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an aliphatic hydrocarbon group having 1 to 40 carbon atoms that is unsubstituted or substituted, an aromatic hydrocarbon-containing group having 6 to 40 carbon atoms that is unsubstituted or substituted, or a heterocyclic-containing group having 2 to 40 carbon atoms that is unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an aromatic hydrocarbon-containing group having an unsubstituted or substituted, or a heterocyclic-containing group having an unsubstituted or substituted are replaced by a divalent group selected from group I below. R 104 If multiple R 104 These elements may also be bonded together to form a benzene ring or a naphthalene ring. R 104 If multiple R 104 These may be the same or different. n represents an integer between 1 and 10. a1 represents an integer between 0 and 2. If n is between 2 and 10, there are multiple R 101 , R 102 , R 103 , R104 And a1 may be the same or they may be different. X represents an n-valence base. Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 230 -, -NR 230 -CO-, -CO-NR 230 -, -NR 230 -COO-, -OCO-NR 230 - or -SiR 230 R 231 -. R 230 and R 231 Each of these independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 40 carbon atoms.

[0024] According to this disclosure, since the compound represented by the above general formula (A1) and a metal deactivator are included, by adding them to a composition containing a curable component, it becomes possible to easily form a composition with an excellent balance between curability and the heat resistance of the cured product. [Modes for carrying out the invention]

[0025] This disclosure relates to compositions and cured products thereof, as well as methods for producing the cured products thereof, and additives added to the compositions. The compositions, cured products, methods for producing cured products, and additives of this disclosure will be described in detail below.

[0026] A. Composition First, the composition of this disclosure will be described. The composition disclosed herein is characterized in that it contains a compound represented by the following general formula (A1), a metal deactivator, and a curable component.

[0027] [ka]

[0028] (In the formula, R 101This represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or an unsubstituted or substituted silyl group having 0 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, an unsubstituted or substituted heterocyclic-containing group, or an unsubstituted or substituted silyl group are replaced by a divalent group selected from group I below. R 102 and R 103 Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted. R 104 This represents a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an aliphatic hydrocarbon group having 1 to 40 carbon atoms that is unsubstituted or substituted, an aromatic hydrocarbon-containing group having 6 to 40 carbon atoms that is unsubstituted or substituted, or a heterocyclic-containing group having 2 to 40 carbon atoms that is unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an aromatic hydrocarbon-containing group having an unsubstituted or substituted, or a heterocyclic-containing group having an unsubstituted or substituted are replaced by a divalent group selected from group I below. R 104 If multiple R 104 These elements may also be bonded together to form a benzene ring or a naphthalene ring. R 104 If multiple R 104 These may be the same or different. n represents an integer between 1 and 10. a1 represents an integer between 0 and 2. If n is between 2 and 10, there are multiple R 101 , R 102 , R 103 , R104 And a1 may be the same or they may be different. X represents an n-valence base. Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 230 -, -NR 230 -CO-, -CO-NR 230 -, -NR 230 -COO-, -OCO-NR 230 - or -SiR 230 R 231 -. R 230 and R 231 Each of these independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 40 carbon atoms.

[0029] According to this disclosure, by using compound A, which is a compound represented by the above general formula (A1), and a metal deactivator in combination, the above composition has an excellent balance of curability and heat resistance of the cured product. The reason why the above composition exhibits an excellent balance between curability and the heat resistance of the cured product when compound A and the metal deactivator are used in combination is not entirely clear, but it can be inferred as follows.

[0030] In other words, compound A has a structure in which the phenolic hydroxyl group is protected, and the protecting group R 101 By eliminating the compound, a phenolic hydroxyl group can be generated. Compound A (hereinafter sometimes referred to as compound A') with the generated phenolic hydroxyl group exhibits antioxidant properties through its ability to scavenge peroxyl radicals, thereby improving the heat resistance of the above composition and its cured product. Furthermore, compound A has a phenolic hydroxyl group that protects the R group. 101Because it has a structure protected by this, for example, it can suppress the inhibition of curing of the curable component compared to those containing antioxidants having phenolic hydroxyl groups. As a result, the above composition has excellent sensitivity to curing reactions, resulting in fewer curing defects and making it possible to obtain a cured product with high crosslink density. The resulting cured product has a high crosslink density, which suppresses the penetration of oxygen into the cured product, and as a result, suppresses oxidative degradation of the curable component and its polymers in high-temperature environments. Consequently, the above cured product has excellent heat resistance. Metal deactivators can, for example, capture metal ions present in or transferred to a composition. Therefore, the generation of peroxy radicals from hydroperoxides generated by heat and light during processing or use due to the catalytic effect of metal ions can be suppressed. Furthermore, the protective group R from compound A due to the catalytic effect of metal ions can be suppressed. 101 This effectively suppresses the detachment of the material. Thus, by using compound A and a metal deactivator in combination, it becomes possible to efficiently prevent oxygen intrusion, capture peroxyl radicals, and suppress the generation of peroxyl radicals, which are essential for achieving excellent curability. As a result, the above composition exhibits an excellent balance between curability and the heat resistance of the cured product.

[0031] The composition disclosed herein comprises compound A, a metal deactivator, and a curable component. The components of the composition of this disclosure will be described in detail below.

[0032] 1. Compound A Compound A is a compound represented by the general formula (A1) above. R in general formula (A1) 101 , R 102 , R 103 and R 104 (Hereinafter, R 101 It may be referred to as such.) an aliphatic hydrocarbon group represented by (hereinafter collectively referred to as "R 101Also called an "aliphatic hydrocarbon group represented by, etc." ) may consist only of hydrogen atoms and carbon atoms and may not contain aromatic hydrocarbon rings or heterocycles. The hydrocarbon group has 1 to 40 carbon atoms. The hydrocarbon group may be unsubstituted or may have substituents. R 101 Examples of aliphatic hydrocarbon groups represented by the above include alkyl groups having 1 to 40 carbon atoms, alkenyl groups having 2 to 40 carbon atoms, cycloalkyl groups having 3 to 40 carbon atoms, cycloalkylalkyl groups having 4 to 40 carbon atoms, and groups in which one or more hydrogen atoms of these groups are substituted by substituents described later.

[0033] R 101 The alkyl groups having 1 to 40 carbon atoms, as represented by the symbols, can consist only of hydrogen atoms and carbon atoms. The alkyl groups having 1 to 40 carbon atoms may be linear or branched. Examples of linear alkyl groups include methyl, ethyl, propyl, butyl, amyl, hexyl, and heptyl. Examples of branched alkyl groups include iso-propyl, sec-butyl, tert-butyl, iso-butyl, iso-pentyl, tert-pentyl, 2-hexyl, 3-hexyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, and tert-octyl.

[0034] R 101 As alkenyl groups having 2 to 40 carbon atoms, represented by the symbols, groups consisting only of hydrogen atoms and carbon atoms can be used. Alkenyl groups having 2 to 40 carbon atoms may be straight-chain alkenyl groups or branched alkenyl groups. Examples include vinyl, ethylene, 2-propenyl, 3-butenyl, 2-butenyl, 4-pentenyl, 3-pentenyl, and 4-dodecenyl. Examples of branched alkenyl groups include 4,8,12-tetradecatrienylenylally.

[0035] R 101As the cycloalkyl group having 3 to 40 carbon atoms, represented by the above, a group consisting only of hydrogen atoms and carbon atoms can be used. The cycloalkyl group having 3 to 40 carbon atoms may be a saturated monocyclic alkyl group or a saturated polycyclic alkyl group. One or more hydrogen atoms in the cycloalkyl group having 3 to 40 carbon atoms may be substituted with alkyl groups. Examples of saturated monocyclic cycloalkyl groups having 3 to 40 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl. Examples of saturated polycyclic alkyl groups include adamantyl, decahydronaphthyl, octahydropentalene, and bicyclo[1.1.1]pentanyl. Examples of alkyl groups that substitute hydrogen atoms in the ring of saturated monocyclic alkyl groups or saturated polycyclic alkyl groups include the above R 101 Examples of alkyl groups having 1 to 40 carbon atoms, as exemplified by the examples shown, include groups similar to those listed above. Examples of groups in which one or more hydrogen atoms in the ring of a saturated polycyclic alkyl group are substituted with an alkyl group include the bornyl group.

[0036] R 101 A cycloalkylalkyl group having 4 to 40 carbon atoms, as expressed by the terms above, refers to a group having 4 to 40 carbon atoms in which the hydrogen atoms of the alkyl group are substituted with a cycloalkyl group. The cycloalkyl group in a cycloalkylalkyl group having 4 to 40 carbon atoms may be a saturated monocyclic alkyl group or a saturated polycyclic alkyl group. Examples of saturated monocyclic alkylalkyl groups having 4 to 40 carbon atoms include cyclopropylmethyl, 2-cyclobutylethyl, and 3-cyclopentylpropyl. Examples of saturated polycyclic alkylalkyl groups having 4 to 40 carbon atoms include 3-3-adamantylpropyl and decahydronaphthylpropyl.

[0037] In this disclosure, the number of carbon atoms in a group refers to the number of carbon atoms in the group after a substituent has replaced a hydrogen atom in the group. For example, if a hydrogen atom in an alkyl group with 1 to 40 carbon atoms is substituted, the number of carbon atoms 1 to 40 refers to the number of carbon atoms after the hydrogen atom has been replaced, and not to the number of carbon atoms before the hydrogen atom was replaced. Furthermore, if the definition of a given symbol in this disclosure includes both a group with a given number of carbon atoms (e.g., an aliphatic hydrocarbon group) and a similar group (e.g., an aliphatic hydrocarbon group) in which the methylene group is replaced by another divalent group, the range of carbon atoms for the latter shall be the same as the range of carbon atoms for the former. Therefore, "R 101 The candidate for "a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, an unsubstituted or substituted heterocyclic-containing group, or an unsubstituted or substituted silyl group are replaced by a divalent group selected from Group I" is defined as "a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I" This refers to a group with 0, an unsubstituted or substituted aromatic hydrocarbon containing methylene groups with 6 to 40 carbon atoms in which one or more methylene groups are replaced by a divalent group selected from group I, a heterocyclic containing group with 2 to 40 carbon atoms in which one or more methylene groups are replaced by a divalent group selected from group I, or a silyl group with 1 to 40 carbon atoms in which one or more methylene groups are replaced by a divalent group selected from group I. Similarly, "R 104The candidate for "」 is a group having 1 to 40 carbon atoms in which one or more of the methylene groups in an aliphatic hydrocarbon group which may be unsubstituted or have a substituent, an aromatic hydrocarbon-containing group which may be unsubstituted or have a substituent, or a heterocyclic-containing group which may be unsubstituted or have a substituent are replaced by a divalent group selected from Group I", which refers to "a group having 1 to 40 carbon atoms in which one or more of the methylene groups in an aliphatic hydrocarbon group which may be unsubstituted or have a substituent are replaced by a divalent group selected from Group I, a group having 6 to 40 carbon atoms in which one or more of the methylene groups in an aromatic hydrocarbon-containing group which may be unsubstituted or have a substituent are replaced by a divalent group selected from Group I, or a group having 2 to 40 carbon atoms in which one or more of the methylene groups in a heterocyclic-containing group which may be unsubstituted or have a substituent are replaced by a divalent group selected from Group I".

[0038] The above-mentioned R 101 and R 104 (hereinafter, may be referred to as R 104 etc.).) The aromatic hydrocarbon-containing group having 6 to 40 carbon atoms represented by (hereinafter, collectively referred to as "the aromatic hydrocarbon-containing group represented by R 104 etc.") may include an aromatic hydrocarbon ring consisting only of hydrogen atoms and carbon atoms and not include a heterocyclic ring. The aromatic hydrocarbon-containing group may be unsubstituted or may have a substituent. Examples of the aromatic hydrocarbon-containing group having 6 to 40 carbon atoms include an aryl group having 6 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, a group in which a hydrogen atom of an aliphatic hydrocarbon group is substituted by an aryl group, and a group in which one or more hydrogen atoms of these groups are substituted by a substituent described later, etc. Regarding the aliphatic hydrocarbon group in which a hydrogen atom is substituted by an aryl group, those satisfying a predetermined number of carbon atoms among the aliphatic hydrocarbon groups represented by R 101 etc. are included.

[0039] The above-mentioned R 104Examples of the aryl group having 6 to 40 carbon atoms represented by etc. can be a group having aromaticity. The above aryl group may have a monocyclic structure or may have a condensed ring structure. Further, the above aryl group may be one in which a monocyclic aryl group and a monocyclic aryl group are linked, may be one in which a monocyclic aryl group and a condensed ring aryl group are linked, or may be one in which a condensed ring aryl group and a condensed ring aryl group are linked. Examples of the linking group for linking two aryl groups include a single bond and a carbonyl group. The hydrogen atom in the above aryl group may be substituted with an unsubstituted or substituted aliphatic hydrocarbon group. Examples of the aryl group having a monocyclic structure include phenyl, biphenyl, and benzophenone (benzoylphenyl). Examples of the aryl group having a condensed ring structure include naphthyl, anthracenyl, phenanthryl, and pyrenyl. Examples of the unsubstituted or substituted aliphatic hydrocarbon group that substitutes the hydrogen atom in the above aryl group are the same as those exemplified for the unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms represented by etc. The unsubstituted or substituted aliphatic hydrocarbon group that substitutes the hydrogen atom in the above aryl group is preferably an unsubstituted alkyl group having 1 to 4 carbon atoms or a group in which all hydrogen atoms in an alkyl group having 1 to 4 carbon atoms are substituted with halogen atoms. In this specification, examples of the halogen atom include those described later as the halogen atom represented by R 101 Examples of the unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms represented by etc. are the same groups as those exemplified above. The unsubstituted or substituted aliphatic hydrocarbon group that substitutes the hydrogen atom in the above aryl group is preferably an unsubstituted alkyl group having 1 to 4 carbon atoms or a group in which all hydrogen atoms in an alkyl group having 1 to 4 carbon atoms are substituted with halogen atoms. In this specification, examples of the halogen atom include those described later as the halogen atom represented by R 104 Examples of the halogen atom described later as the halogen atom represented by are included.

[0040] The above R 104 Examples of the arylalkyl group having 7 to 40 carbon atoms represented by etc. are such that one or more hydrogen atoms in the alkyl group represented by R 101 etc. are R 104Examples include groups substituted with aryl groups represented by the above. Examples of arylalkyl groups having 7 to 40 carbon atoms include benzyl, fluorenyl, indenyl, 9-fluorenylmethyl, α-methylbenzyl, α,α-dimethylbenzyl, phenylethyl and naphthylpropyl groups, and groups in which the hydrogen atoms in these groups are substituted with aliphatic hydrocarbon groups that are unsubstituted or substituted. Examples of unsubstituted or substituted aliphatic hydrocarbon groups that substitute the alkyl group in the arylalkyl group and the hydrogen atoms in the arylalkyl group include the above R 101 Examples of aliphatic hydrocarbon groups having 1 to 40 carbon atoms, represented by the same groups as those exemplified, include those similar to those mentioned above.

[0041] The above R 104 Heterocyclic groups with 2 to 40 carbon atoms, represented by the same names (hereinafter collectively referred to as "R") 104 As a heterocyclic ring-containing group (also referred to as "a heterocyclic ring-containing group represented by, etc."), any group containing a heterocyclic ring that includes atoms other than hydrogen and carbon atoms can be used. The above heterocyclic ring-containing group may be unsubstituted or may have substituents. Examples of the heterocyclic groups mentioned above include heterocyclic groups such as tetrahydrofuran, dioxolanyl, tetrahydropyranyl, morpholylfuran, thiophene, methylthiophene, hexylthiophene, benzothiophene, pyrrole, pyrrolidine, imidazole, imidazolidine, imidazoline, pyrazole, pyrazolidine, piperidine, and piperazine; groups in which the hydrogen atoms in these heterocyclic groups are substituted with unsubstituted or substituted aliphatic hydrocarbon groups; groups in which one or more hydrogen atoms of the aliphatic hydrocarbon group are substituted with the above heterocyclic groups; and groups in which one or more hydrogen atoms of these groups are substituted with substituents described later. Examples of the above aliphatic hydrocarbon groups include the above R 101Examples of aliphatic hydrocarbon groups having 1 to 40 carbon atoms, represented by the symbols, etc., that satisfy the number of carbon atoms of a heterocyclic group. In this specification, "2 to 40" in "heterocyclic group having 2 to 40 carbon atoms" refers to the number of carbon atoms of the "heterocyclic group," not the "heterocyclic group."

[0042] R 101 The silyl group having 0 to 40 carbon atoms, represented by , may be unsubstituted or substituted. Examples of the above silyl group include a silyl group in which the hydrogen atoms are unsubstituted, a substituted silyl group in which the hydrogen atoms are substituted with other substituents, and a group in which one or more of the hydrogen atoms of these groups are substituted with substituents described later. Examples of the above-mentioned substituted silyl groups include monoalkylsilyl groups such as monomethylsilyl groups, monoarylsilyl groups such as monophenylsilyl groups, dialkylsilyl groups such as diethylsilyl groups, diarylsilyl groups such as diphenylsilyl groups, trialkylsilyl groups such as trimethylsilyl groups, triarylsilyl groups such as triphenylsilyl groups, monoalkyldiarylsilyl groups such as methyldiphenylsilyl groups, dialkylmonoarylsilyl groups such as dimethylphenylsilyl groups, trialkoxysilyl groups such as trimethoxysilyl groups and triethoxysilyl groups, and alkylalkoxysilyl groups having both alkyl and alkoxy groups.

[0043] R 104 Examples of halogen atoms represented by this formula include fluorine, chlorine, bromine, and iodine atoms.

[0044] In a group in which two or more methylene groups of the above-mentioned aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group are replaced by divalent groups selected from group I, the multiple divalent groups may be the same or different from each other, but the multiple divalent groups shall not be adjacent to each other.

[0045] R 101"A group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, an unsubstituted or substituted heterocyclic-containing group, or an unsubstituted or substituted silyl group are replaced by a divalent group selected from group I" and R 104 The following explains the "groups having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, or an unsubstituted or substituted heterocyclic-containing group are replaced by a divalent group selected from group I" represented by . Among the above groups having 1 to 40 carbon atoms, the unsubstituted or substituted aliphatic hydrocarbon group is R 101 Examples of unsubstituted or substituted aliphatic hydrocarbon groups represented by the above include those similar to the groups listed above, as well as groups in which the methylene group in the group is substituted with a divalent group selected from group I, which is suitable for achieving the above number of carbon atoms. Furthermore, examples of unsubstituted or substituted aromatic hydrocarbon-containing groups, unsubstituted or substituted heterocyclic-containing groups, and unsubstituted or substituted silyl groups among the above groups with 1 to 40 carbon atoms include R 104 Examples of unsubstituted or substituted aromatic hydrocarbon-containing groups, unsubstituted or substituted heterocyclic-containing groups, and unsubstituted or substituted silyl groups, as shown above, include those similar to the groups listed above, as well as groups in which the methylene group in the group is substituted with a divalent group selected from group I, which is suitable for achieving the above number of carbon atoms.

[0046] In the case where the aliphatic hydrocarbon group is an alkyl group, examples of groups in which one or more methylene groups of the above aliphatic hydrocarbon group are replaced with a divalent group selected from group I include, for example, a group in which the methylene group at the benzene ring end of the alkyl group is replaced with -O-, i.e., an alkoxy group. Also, benzene ring bond-OR 101 As a group represented by R 101A group in which the methylene group at the -O- end is replaced with -CO-O-, i.e., a group represented as -O-CO-OR (where R is R 101 This represents the group obtained by removing the methylene group at the oxygen atom end. Other forms such as ) can also be used. Furthermore, the above divalent groups are selected such that no oxygen atoms are adjacent to each other. For example, "-OR 101 The R 101 If the methylene group at the -O- terminal is replaced with a divalent group selected from group I above, then -O- and -OCO- cannot be selected as the divalent group. For example, -COO-, -CO-, -CS-, -S-, -SO-, -SO2-, and -NR are available. 230 -, -NR 230 -CO-, -CO-NR 230 -, -NR 230 -COO- or -SiR 230 R 231 - will be selected. In this disclosure, the divalent groups that replace the methylene groups are typically selected so as not to be adjacent to each other. That is, the methylene groups that are replaced by divalent groups are selected so as not to be adjacent to each other. R in group I above 230 and R 231 The unsubstituted aliphatic hydrocarbon group having 1 to 40 carbon atoms used is the above R 101 Among the aliphatic hydrocarbon groups used in the above applications, groups in which hydrogen atoms are not substituted with substituents can be used.

[0047] Aliphatic hydrocarbon groups, aromatic hydrocarbon-containing groups, heterocyclic-containing groups, silyl groups, and groups in which one or more methylene groups are replaced by divalent groups selected from the above group I, as described by general formula (A1), etc., substituents that substitute hydrogen atoms in these groups, more specifically, alkyl groups, alkenyl groups, cycloalkyl groups, cycloalkylalkyl groups, aryl groups, arylalkyl groups, heterocyclic-containing groups, and silyl groups, and hydrogen atoms in groups in which one or more methylene groups are replaced by divalent groups selected from the above group I Substituents that replace one or more of the following include, for example, ethylenically unsaturated groups such as vinyl, allyl, acrylic, and methacrylic; halogen atoms such as fluorine, chlorine, bromine, and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, Acyl groups such as carbamoyl; acyloxy groups such as acetyloxy and benzoyloxy; amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroyl Substituted amino groups such as amino, carbamoylamino, N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, sulfamoylamino, N,N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, and phenylsulfonylamino;Examples include sulfonamide groups, sulfonyl groups, carboxyl groups, cyano groups, sulfo groups, hydroxyl groups, nitro groups, mercapto groups, imide groups, carbamoyl groups, sulfonamide groups, phosphonic acid groups, phosphate groups, or salts of carboxyl groups, sulfo groups, phosphonic acid groups, or phosphate groups. In other words, examples of the substituents include ethylenically unsaturated groups, halogen atoms, acyl groups, acyloxy groups, substituted amino groups, sulfonamide groups, sulfonyl groups, carboxyl groups, cyano groups, sulfo groups, hydroxyl groups, nitro groups, mercapto groups, imide groups, carbamoyl groups, sulfonamide groups, phosphonic acid groups, phosphate groups, or salts of carboxyl groups, sulfo groups, phosphonic acid groups, or phosphate groups.

[0048] In the above general formula (A1), R 101 From the viewpoint of facilitating removal by heat treatment, it is preferable that the group is an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, or an unsubstituted or substituted heterocyclic-containing group in which the methylene group at the oxygen atom end is replaced with a divalent group selected from the above group I, resulting in a group having 1 to 40 carbon atoms or an unsubstituted or substituted silyl group having 0 to 40 carbon atoms. 101Preferably, the carbon atoms are: a group having 1 to 40 carbon atoms in which the methylene group at the oxygen atom-side end of an unsubstituted or substituted aliphatic hydrocarbon group is substituted with the divalent group; a group having 6 to 40 carbon atoms in which the methylene group at the oxygen atom-side end of an unsubstituted or substituted aromatic hydrocarbon-containing group is substituted with the divalent group (the oxygen atom-side end is bonded to the divalent group); a group having 2 to 40 carbon atoms in which the methylene group at the oxygen atom-side end of an unsubstituted or substituted heterocyclic-containing group is substituted with the divalent group (the oxygen atom-side end is bonded to the divalent group); or an unsubstituted or substituted silyl group having 0 to 40 carbon atoms, among which, Preferably, the group is a carbon-1 to carbon-40 group in which the methylene group at the oxygen-side terminal of an unsubstituted or substituted aliphatic hydrocarbon group is substituted with -CO-O-, and in particular, it is a carbon-1 to carbon-40 group in which the methylene group at the oxygen-side terminal of an unsubstituted or substituted alkyl group is substituted with -CO-O-, and among these, it is particularly preferable that the group is a carbon-1 to carbon-40 group in which the methylene group at the oxygen-side terminal of an unsubstituted or substituted alkyl group is bonded to -CO-O-, i.e., a group represented by -CO-O-R'' (where R'' is an unsubstituted or substituted alkyl group having 1 to 39 carbon atoms). In this disclosure, the above-mentioned R'' is preferably an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, more preferably an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms, particularly preferably an unsubstituted alkyl group having 1 to 8 carbon atoms, more preferably an unsubstituted alkyl group having 3 to 6 carbon atoms, and more preferably iso-propyl, n-butyl, sec-butyl, tert-butyl, iso-butyl, n-pentyl, iso-pentyl, tert-pentyl, and more preferably n-butyl, sec-butyl, tert-butyl, iso-butyl, tert-butyl, i.e., R 101 However, it is preferable that the group is represented by -CO-O-C4H9, and in particular that R'' is tert-butyl, that is, R 101 However, it is preferable that it be a -CO-O-tert-butyl group. The above R 101 However, because of the above-mentioned group, compound A undergoes heat treatment R 102 This is because it makes it easier to control the detachment.

[0049] Protecting group R contained in compound A above 101 The temperature at which the material is desorbed by heat treatment is set appropriately according to the intended use of the composition, but for example, it can be 80°C to 300°C, preferably 100°C to 290°C, particularly preferably 120°C to 280°C, and especially preferably 150°C to 250°C, and preferably 180°C to 240°C. This is because it provides an even better balance between curability and the heat resistance of the cured product. The desorption temperature can be defined as the temperature at which a 5% mass loss in thermal analysis is observed. As a measurement method, for example, using an STA (Differential Thermogravimetric Analysis System), the thermal loss of a sample of approximately 5 mg is measured when heated in a nitrogen atmosphere of 200 mL / min, with a starting temperature of 30°C, an ending temperature of 500°C, and a heating rate of 10°C / min. The desorption temperature can then be defined as the temperature at which the sample weight has decreased by 5 mass compared to the sample weight at 30°C. For differential thermogravimetric simultaneous measurement, the STA7000 (manufactured by Hitachi High-Tech Science Co., Ltd.) can be used.

[0050] In the above general formula (A1), R 101 From the viewpoint of facilitating detachment by light irradiation, photo-leaving protecting groups such as o-nitrobenzyl groups can also be used. Note that the above R 101 If the protecting group is a photoleaving protecting group, then the protecting group R 101 The wavelength of light that is detached from compound A can include, for example, a wavelength of 365 nm, more specifically, a wavelength of 250 nm to 450 nm, and preferably a wavelength of 280 nm to 380 nm. Compounds A to R 101The integrated amount of light irradiated to desorb is, for example, 1,000 mJ / cm². 2 More than 10,000mJ / cm 2 It can be set as follows: 1,000 mJ / cm² 2 Super 5,000mJ / cm 2 Preferably, it is 2,000 mJ / cm². 2 More than 4,000mJ / cm 2 The following is more preferable, as it results in a better balance between curability and the heat resistance of the cured product.

[0051] In the above general formula (A1), R 102 and R 103 Each of these is independently preferably a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, or a group in which one or more hydrogen atoms of the alkyl group are single-layer substituted with the above-mentioned substituents; that is, each is independently preferably a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 40 carbon atoms, and among these, it is especially preferable that each is a hydrogen atom or an unsubstituted alkyl group having 1 to 40 carbon atoms. Also, R 102 and R 103 Preferably, at least one of them is an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted, and among them, R 102 and R 103 Each of these independently is an alkyl group having 1 to 40 carbon atoms, or a group in which one or more hydrogen atoms of the alkyl group are single-layer substituted with the above-mentioned substituents, that is, R 102 and R 103 It is preferable that both are unsubstituted or substituted alkyl groups having 1 to 40 carbon atoms, and in particular, it is preferable that they are unsubstituted alkyl groups having 1 to 40 carbon atoms. Among them, R 102 and R 103Each of these is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, particularly preferably an alkyl group having 2 to 6 carbon atoms, and more preferably an alkyl group having 4 carbon atoms represented by -C4H9, and most preferably a tert-butyl group. 102 and R 103 Because the above group is R, compound A has a protecting group R 101 This is because the antioxidant capacity changes significantly before and after the elimination of compound A. Furthermore, compound A suppresses the occurrence of curing inhibition. Consequently, the balance between curability and the heat resistance of the cured product is further improved. Moreover, synthesis becomes easier.

[0052] The above R 104 Preferably, the halogen atom or an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted. 104 Because the above group is R, compound A has a protecting group R 101 This is because the antioxidant capacity changes significantly before and after the elimination of compound A. Furthermore, compound A suppresses the occurrence of curing inhibition. Consequently, the balance between curability and the heat resistance of the cured product is further improved. Moreover, synthesis becomes easier.

[0053] The above a1 is an integer between 0 and 2, preferably between 0 and 1, and preferably 0. This is because the above composition has an even better balance between curability and the heat resistance of the cured product.

[0054] The above value of n is an integer between 1 and 10, preferably between 1 and 6, and more preferably between 1 and 4, and particularly preferably between 2 and 4. This is because when n is within the above range, the above composition has an even better balance of curability and the heat resistance of the cured product.

[0055] The above X represents an n-valent atom or group. Such X can be any group that provides the desired curability and heat resistance of the cured product. For example, substituents that substitute for the group represented by X and the alkoxy group described in International Publication No. 2014 / 021023, or the group represented by X in general formula (1) of Japanese Patent Application Publication No. 2018-150301 can also be used. More specifically, X above refers to: direct bond; hydrogen atom; halogen atom; cyano group; hydroxyl group; nitro group; carboxyl group; nitrogen atom; oxygen atom; sulfur atom; phosphorus atom; the group represented by (II-a) below; the group represented by (II-b) below; >C=O; >NR 53 ;-OR 53 ;-SR 53 ;-NR 53 R 54 Examples include: an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms with the same valency as n; an aromatic hydrocarbon-containing group having 6 to 40 carbon atoms with the same valency as n with the same valency as n with the same valency as n; a heterocyclic-containing group having 2 to 40 carbon atoms with the same valency as n with the same valency as n with the same valency as n with the same valency as n; or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group having the same valency as n are replaced by a divalent group selected from group I below; a group having 6 to 40 carbon atoms in which one or more methylene groups in an aromatic hydrocarbon-containing group having the same valency as n with the same valency as n are replaced by a divalent group selected from group I below; or a group having 2 to 40 carbon atoms in a heterocyclic-containing group having the same valency as n with the same valency as n are replaced by a divalent group selected from group I below.

[0056] R 53 and R 54Each of these independently represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, or an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms; or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from group I below; a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from group I below; or a group having 2 to 40 carbon atoms in an unsubstituted or substituted heterocyclic-containing group is replaced by a divalent group selected from group I below.

[0057] n is 3 when X is a nitrogen atom, a phosphorus atom, a group represented by (II-a) below, or a group represented by (II-b) below. X is a direct bond, an oxygen atom, a sulfur atom, >C=O, -NH-CO-, -CO-NH-, or >NR 53 If so, n is 2. X is a hydrogen atom, halogen atom, cyano group, hydroxyl group, nitro group, carboxyl group, -OR 53 , -SR 53 or -NR 53 R 54 In this case, n is 1. X may also form a ring together with the benzene ring to which it is bonded.

[0058] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 230 -, -NR 230 -CO-, -CO-NR 230 -, -NR 230 -COO-, -OCO-NR 230 - or -SiR 230 R 231 -. R 230 and R 231 Each of these independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.

[0059] [ka]

[0060] (In the formula, * indicates a joining point.)

[0061] Examples of aliphatic hydrocarbon groups having the same valency as n represented by X in general formula (A1), aromatic hydrocarbon-containing groups having the same valency as n, heterocyclic-containing groups having the same valency as n, and groups in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group are replaced by divalent groups selected from group I include, for example, R 101 Etc. or R 104 Examples include aliphatic hydrocarbon groups, aromatic hydrocarbon-containing groups, and heterocyclic-containing groups represented by the above, as well as groups in which one or more methylene groups in an aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group are replaced by a divalent group selected from group I below, and which have n-1 hydrogen atoms removed from the above-mentioned groups and satisfy a predetermined number of carbon atoms. R 53 and R 54 Examples of aliphatic hydrocarbon groups, aromatic hydrocarbon-containing groups, and heterocyclic-containing groups represented by , and groups in which one or more methylene groups in the above aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group are replaced by a divalent group selected from group I include, for example, R 101 Etc. or R 104 Examples include aliphatic hydrocarbon groups, aromatic hydrocarbon-containing groups, and heterocyclic-containing groups represented by the above, as well as groups in which one or more methylene groups in an aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group are replaced by a divalent group selected from Group I, provided that the group satisfies the specified number of carbon atoms. Furthermore, in group I, R 230 and R 231 The content of the unsubstituted aliphatic hydrocarbon group with 1 to 20 carbon atoms represented by R 101 R in group I used in the above, etc. 230 , R 231 It can be used as a similar base.

[0062] In general formula (A1), X is preferably an aliphatic hydrocarbon group having 1 to 40 carbon atoms and having the same valency as n when n is 2 to 10; an aromatic hydrocarbon-containing group having 6 to 40 carbon atoms and having the same valency as n and having the same valency as n and having the same valency as n and having the same valency as n and having the same valency as n and having the same valency as n and having the same valency as n and having the same valency as n and having the same valency as n, in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group are replaced with a divalent group selected from the group consisting of Group I above (the number of carbon atoms in the groups in which the methylene groups of the aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, and heterocyclic-containing group are replaced is 1 to 40, 6 to 40, and 2 to 40, respectively). In particular, X is preferably an aliphatic hydrocarbon group having 2 to 30 carbon atoms and having the same valence as n, either unsubstituted or substituted; an aromatic hydrocarbon-containing group having 6 to 30 carbon atoms and having the same valence as n, either unsubstituted or substituted; a heterocyclic-containing group having 3 to 30 carbon atoms and having the same valence as n, either unsubstituted or substituted; or a group having 2 to 30 carbon atoms in which one or more methylene groups in an aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group having the same valence as n are replaced with a divalent group selected from the group consisting of -O-, -COO-, -OCO-, and -CO- (the number of carbon atoms in the groups in which the methylene groups of the aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, and heterocyclic-containing group are substituted is 2 to 30, 6 to 30, and 2 to 30, respectively).In particular, X is preferably an aliphatic hydrocarbon group having 10 to 25 carbon atoms and having the same valency as n, either unsubstituted or substituted; a heterocyclic group having 4 to 25 carbon atoms and having the same valency as n, either unsubstituted or substituted; or a group having 4 to 25 carbon atoms in which one or more methylene groups in the aliphatic hydrocarbon group or heterocyclic group having the same valency as n are replaced with divalent groups selected from the group consisting of -O-, -COO-, -OCO-, and -CO- (the number of carbon atoms in the methylene-substituted groups of the aliphatic hydrocarbon group and the heterocyclic group is 10 to 25 and 4 to 25, respectively). In particular, it is preferable that the composition has a valence equal to n and is an unsubstituted or substituted aliphatic hydrocarbon group having 14 to 22 carbon atoms; that it has a valence equal to n and is an unsubstituted or substituted heterocyclic group having 5 to 22 carbon atoms; or that the composition has a valence equal to n and is an unsubstituted or substituted aliphatic hydrocarbon group or heterocyclic group having 5 to 22 carbon atoms in which one or more methylene groups are replaced with divalent groups selected from the group consisting of -O-, -COO-, -OCO-, and -CO- (the number of carbon atoms in the methylene-substituted groups of the aliphatic hydrocarbon group and the heterocyclic group is 14 to 22 and 5 to 22, respectively). This is because it provides an even better balance between the curability of the composition and the heat resistance of the resulting cured product. In this disclosure, (1) when n is 2, it is preferable that X in general formula (A1) is a substituent represented by the following general formula (101) or a group selected from the following group 1. (2) when n is 3, it is preferable that X in general formula (A1) is a group selected from the following group 2. (3) when n is 4, it is preferable that X in general formula (A1) is a group selected from the following group 3. (4) when n is 5, it is preferable that X in general formula (A1) is a group selected from the following group 4. (5) when n is 6, it is preferable that X in general formula (A1) is a group selected from the following group 5. (6) when n is 1, it is preferable that X in general formula (A1) is a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from the above group I. This is because the above composition offers an even better balance between curability and the heat resistance of the cured product.

[0063] [ka]

[0064] (In the formula, Y 111 and Y 115 Each of these independently represents a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, either unsubstituted or substituted, or a group having 1 to 8 carbon atoms in which one or more methylene groups in the unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from group I above. Y 112 and Y 114 These are -O-, -CO-, -CO-O-, -O-CO-, and -NR, respectively, independently. 213 -,-CO-NR 213 - or -NR 213 It represents a group represented by -CO-, R 213This represents a group having 1 to 40 carbon atoms in which one or more of the hydrogen atoms, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, or a methylene group in an unsubstituted or substituted aliphatic hydrocarbon group is replaced by a divalent group selected from the above group I. Y 113 -CR 214 R 215 -, -NR 216 - represents a group represented by the following general formula (103), a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms that is unsubstituted or substituted, a divalent aromatic hydrocarbon-containing group having 6 to 40 carbon atoms that is unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from the above group I, or a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from the above group I. R 214 and R 215 Each of these independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms. R 216 This represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I above, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from Group I above, or a group having 2 to 40 carbon atoms in an unsubstituted or substituted heterocyclic-containing group are replaced by a divalent group selected from Group I above. * indicates a connection point.

[0065] [ka]

[0066] (In the formula, Y 119 and Y 120 Each of these independently represents a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms that is either unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from the above group I. * indicates a connection point.

[0067] [ka]

[0068] (In the formula, R 31 This represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, or an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I above, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from Group I above, or a group having 2 to 40 carbon atoms in an unsubstituted or substituted heterocyclic-containing group is replaced by a divalent group selected from Group I above. * indicates a connection point.

[0069] [ka]

[0070] (In the formula, R 32This represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I above, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from Group I above, or a group having 2 to 40 carbon atoms in an unsubstituted or substituted heterocyclic-containing group is replaced by a divalent group selected from Group I above, and the group contains two or more R 32 If there are two or more R 32 They may be the same, or they may be different. Z 11 These are, independently, direct bonds, -O-, -S-, >CO, -CO-O-, -O-CO-, -SO2-, -SS-, -SO-, >NR 63 ,-PR 63 - represents a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms that is unsubstituted or substituted, a divalent aromatic hydrocarbon-containing group having 6 to 40 carbon atoms that is unsubstituted or substituted, a divalent heterocyclic-containing group having 2 to 40 carbon atoms that is unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I above, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from Group I above, or a group having 2 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted heterocyclic-containing group are replaced by a divalent group selected from Group I above. R 63This represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, or an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I above, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from Group I above, or a group having 2 to 40 carbon atoms in an unsubstituted or substituted heterocyclic-containing group is replaced by a divalent group selected from Group I above. * indicates a connection point.

[0071] [ka]

[0072] (In the formula, R 32 R in group 2 above 32 It represents the same group, and has two or more R groups. 32 If there are two or more R 32 They may be the same, or they may be different. Z 11 Z in group 2 above 11 It represents groups within the same range as the group represented by , * indicates a connection point.

[0073] [ka]

[0074] (In the formula, Z 10 , Z 11 , Z 12 , Z 13 and Z 14 Each of the groups represented by the above group 2 is independently Z 11 It represents groups within the same range as the group represented by , * indicates a connection point.

[0075] [ka]

[0076] (In the above formula, Z 10 , Z 11 , Z 12 , Z 13 , Z 14 and Z 15 Each of the groups represented by the above group 2 is independently Z 11 It represents groups within the same range as the group represented by , * indicates a connection point.

[0077] Note Y 111 , Y 113 , Y 115 , Y 119 , Y 120 and Z 11 The aliphatic hydrocarbon groups represented by are unsubstituted or substituted divalent aliphatic hydrocarbon groups and groups in which the methylene group in the aliphatic hydrocarbon group is replaced with a divalent group selected from group I (hereinafter also referred to as "divalent aliphatic hydrocarbon groups, etc."). 101 Examples include groups obtained by removing one hydrogen atom from an unsubstituted or substituted aliphatic hydrocarbon group used in the following applications, which satisfy the specified number of carbon atoms. 113 and Z 11 As for the unsubstituted or substituted divalent aromatic hydrocarbon-containing groups represented by and the groups in which the methylene group in the aromatic hydrocarbon-containing group is replaced with a divalent group selected from group I, R 104 Examples include groups obtained by removing one hydrogen atom from an unsubstituted or substituted aromatic hydrocarbon-containing group used in the like, which satisfy the specified number of carbon atoms. 11 As for the heterocyclic group having an unsubstituted or substituted divalent heterocyclic group represented by and the group in which the methylene group in the heterocyclic group is replaced with a divalent group selected from group I, R 104Examples include groups obtained by removing one hydrogen atom from an unsubstituted or substituted heterocyclic group used in applications such as the above, which satisfy a predetermined number of carbon atoms. Y 111 , Y 113 , Y 115 , Y 119 and Y 120 As the unsubstituted or substituted divalent aliphatic hydrocarbon group represented by , an unsubstituted or substituted alkylene group obtained by removing one hydrogen atom from an unsubstituted or substituted alkyl group can be used. Y in equation (101) above 111 and Y 115 They may be the same or they may be different. Y in equation (103) above 119 and Y 120 They may be the same or they may be different. R 213 , R 216 , R 217 , R 31 , R 32 and R 63 As for aliphatic hydrocarbon groups that are unsubstituted or substituted, represented by R, and aliphatic hydrocarbon groups in which the methylene group in the aliphatic hydrocarbon group is replaced with a divalent group selected from group I, 101 This can be equivalent to an unsubstituted or substituted aliphatic hydrocarbon group represented by, for example, etc. R 213 , R 216 , R 217 , R 31 , R 32 and R 63 As for aromatic hydrocarbon-containing groups that are unsubstituted or substituted, represented by R, and groups in which the methylene group in the aromatic hydrocarbon-containing group is replaced with a divalent group selected from group I, the aromatic hydrocarbon-containing group is R 104 The content of an aromatic hydrocarbon-containing group, which is either unsubstituted or substituted, can be the same as that of an aromatic hydrocarbon-containing group represented by, for example. R 213 , R 216 , R 217 , R 31 , R32 and R 63 As for heterocyclic groups that are unsubstituted or substituted, and heterocyclic groups in which the methylene group in the heterocyclic group is replaced with a divalent group selected from group I, R 104 This can be equivalent to a heterocyclic group containing unsubstituted or substituted elements, as represented by the terms "etc." R 214 and R 215 A alkyl group having 1 to 8 carbon atoms, represented by R 214 and R 215 As for aryl groups with 6 to 20 carbon atoms and arylalkyl groups with 7 to 20 carbon atoms represented by R, 101 Etc. or R 104 The content can be the same as alkyl groups, aryl groups, and arylalkyl groups used in the above applications that satisfy a predetermined number of carbon atoms. Multiple Zs included in each of the formulas in groups 2 and 3 above 11 The same applies to the Z included in each of the equations in group 4 above. 10 ~Z 14 and Z included in each of the formulas in group 5 above 10 ~Z 15 They may be the same or they may be different.

[0078] In this disclosure, when n is 2, it is preferable that X is a group represented by the above general formula (101). This is because the balance between the curability of the above composition and the heat resistance of the resulting cured product is further improved. In the above general formula (101), Y 111 and Y 115 Each of these is preferably an unsubstituted or substituted divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, and more preferably an unsubstituted or substituted divalent aliphatic hydrocarbon group having 1 to 3 carbon atoms, and particularly preferably an unsubstituted alkylene group having 1 to 3 carbon atoms. This is because it provides an even better balance between the curability of the composition and the heat resistance of the resulting cured product. In the above general formula (101), Y 112 and Y 114Each of these is preferably independently -O-, -CO-, -CO-O-, or -O-CO-, and among these, -CO-O- or -O-CO- is preferred. This is because it results in an even better balance between the curability of the above composition and the heat resistance of the resulting cured product. In the above general formula (101), Y 113 Preferably, is a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms that is unsubstituted or substituted, a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted divalent aliphatic hydrocarbon group are replaced with a divalent group selected from the above group I, or a group represented by the above general formula (103). In particular, is a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms that is unsubstituted or substituted, a group having 1 to 20 carbon atoms in which one or more methylene groups in an unsubstituted or substituted divalent aliphatic hydrocarbon group are replaced with a divalent group selected from the above group I, or a group represented by the above general formula (103). In particular, is a group having 1 to 20 carbon atoms in which one or more methylene groups in an unsubstituted or substituted divalent aliphatic hydrocarbon group are replaced with a divalent group selected from the above group I, or a group represented by the above general formula (103). In particular, is a group represented by the above general formula (103). This is because the balance between the curability of the above composition and the heat resistance of the resulting cured product becomes even better.

[0079] In the above general formula (103), Y 119 and Y 120Preferably, each of these is independently a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in the unsubstituted or substituted divalent aliphatic hydrocarbon group are replaced with a divalent group selected from the above group I. In particular, it is preferable that the group is a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, especially a divalent aliphatic hydrocarbon group having 1 to 10 carbon atoms, especially a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, and especially a linear or branched alkylene group having 2 to 5 carbon atoms. This is because the balance between the curability of the above composition and the heat resistance of the resulting cured product is further improved.

[0080] In this disclosure, when n is 3, X is preferably a group represented by general formula (II-2), a group represented by general formula (II-3), or a group represented by general formula (II-6) in group 2, and is particularly preferably a group represented by general formula (II-6). This is because the balance between the curability of the composition and the heat resistance of the resulting cured product is further improved.

[0081] The group represented by general formula (II-2), the group represented by general formula (II-3), and Z in general formula (II-6) 11 Preferably, the group is a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms that is directly bonded or unsubstituted or substituted; more preferably, it is a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms that is directly bonded or substituted; particularly preferably, it is an alkylene group having 1 to 10 carbon atoms that is directly bonded or substituted; and most preferably, it is an alkylene group having 1 to 5 carbon atoms that is directly bonded or unsubstituted. This is because it provides an even better balance between the curability of the composition and the heat resistance of the resulting cured product. Multiple Zs contained in the group represented by general formula (II-2), the group represented by general formula (II-3), and the group represented by general formula (II-6) 11 They may be the same or they may be different.

[0082] In particular, in this disclosure, the three Zs in the base represented by general formula (II-2) 11 Preferably, at least one of these groups is directly bonded and at least one is a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms and being either unsubstituted or substituted; more preferably, at least one is directly bonded and at least one is a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms and being either unsubstituted or substituted; particularly preferably, at least one is directly bonded and at least one is an alkylene group having 1 to 10 carbon atoms and being either unsubstituted or substituted; and most preferably, at least one is directly bonded and at least one is an unsubstituted alkylene group having 1 to 5 carbon atoms. This is because it provides an even better balance between the curability of the composition and the heat resistance of the resulting cured product. Furthermore, Z in the group represented by general formula (II-3) and the group represented by (II-6) 11 Preferably, all of these are divalent aliphatic hydrocarbon groups having 1 to 40 carbon atoms, either unsubstituted or substituted; more preferably, they are divalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms, either unsubstituted or substituted; particularly preferably, they are alkylene groups having 1 to 10 carbon atoms, either unsubstituted or substituted; and most preferably, they are unsubstituted alkyl groups having 1 to 5 carbon atoms. This is because it provides an even better balance between the curability of the composition and the heat resistance of the resulting cured product.

[0083] R in the group represented by general formula (II-2) 32Preferably, the component is a hydrogen atom or an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted; more preferably, it is a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms, either unsubstituted or substituted; and especially preferably, it is a hydrogen atom. This is because it provides an even better balance between the curability of the composition and the heat resistance of the resulting cured product.

[0084] In this disclosure, when n is 4, X is preferably a group represented by general formula (III-1) in group 3. In general formula (III-1), Z 11 Preferably, the group is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in the unsubstituted or substituted aliphatic hydrocarbon group are replaced with a divalent group selected from Group I above. In particular, it is preferable that the group is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a group having 1 to 20 carbon atoms in which one or more methylene groups in the unsubstituted or substituted aliphatic hydrocarbon group are replaced with a divalent group selected from Group I above. In particular, it is preferable that one or more methylene groups in an unsubstituted or substituted alkylene group are replaced with a divalent group selected from Group I above, and more preferably, one or more methylene groups in an unsubstituted alkylene group are replaced with -O-, -COO-, -OCO-, or -CO-, and more preferably, one of the methylene groups in an alkylene group having 2 to 5 carbon atoms is replaced with -O-CO- or -CO-O-, and more preferably, one of the methylene groups in an alkylene group having 2 to 5 carbon atoms is replaced with -O-CO- or -CO-O-. This is because the balance between the curability of the above composition and the heat resistance of the resulting cured product is further improved. In each n, since X is the group described above, compound A has a protecting group R 101 This is because the antioxidant capacity changes significantly before and after the elimination of the compound. As a result, the above composition has an excellent balance between curability and the heat resistance of the cured product.

[0085] The bonding position of the above X with the benzene ring may be any position capable of bonding within the benzene ring. For example, for the bonding position of the above R 101 -O-, it is preferably in the para position with respect to the bonding position. Since the above bonding position is the above position, the above Compound A will have a large change in antioxidant ability before and after the elimination of the protecting group R 101 . As a result, the above composition will be excellent in the balance between curability and heat resistance of the cured product.

[0086] Specific examples of Compound A include, specifically, compounds specifically described in International Publication No. 2014 / 021023 and the like.

[0087] The method for producing the above Compound A is not particularly limited as long as it can obtain the desired structure. For example, it can be the same method as described in International Publication No. 2014 / 021023.

[0088] As the type of the above Compound A, there may be only one type in the composition, or there may be two or more types.

[0089] The content of the above Compound A may be any as long as the desired curability and heat resistance of the cured product can be obtained, and it can be appropriately set according to the use and the like of the above composition. The content of the above Compound A is preferably, for example, 0.01 part by mass or more and 20 parts by mass or less, more preferably 0.05 part by mass or more and 10 parts by mass or less, and particularly preferably 0.1 part by mass or more and 5 parts by mass or less, per 100 parts by mass of the solid content of the above composition. Since the above content is within the above range, the above composition will be even more excellent in the balance between curability and heat resistance of the cured product. Note that the solid content includes all components other than the solvent.

[0090] The content of compound A varies depending on the content of the solvent, etc., but for example, it is preferably 0.001 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the composition, more preferably 0.005 parts by mass or more and 10 parts by mass or less, and particularly preferably 0.01 parts by mass or more and 5 parts by mass or less. This is because the composition has an even better balance between curability and the heat resistance of the cured product when the content is within the above range.

[0091] The content of compound A is preferably 0.01 parts by mass or more and 20 parts by mass or less in 100 parts by mass of the total of compound A, metal deactivator and curable component, more preferably 0.05 parts by mass or more and 10 parts by mass or less, particularly preferably 0.1 parts by mass or more and 5 parts by mass or less, and especially preferably 0.5 parts by mass or more and 3 parts by mass or less. This is because the above composition has an even better balance between curability and the heat resistance of the cured product when the content of compound A is within the above range.

[0092] The total content of compound A and the metal deactivator is preferably 0.01 parts by mass or more and 10 parts by mass or less per 100 parts by mass of the total of compound A, the metal deactivator, and the curable component, more preferably 0.1 parts by mass or more and 5 parts by mass or less, and particularly preferably 0.5 parts by mass or more and 3 parts by mass or less. This is because the above composition has an even better balance between curability and the heat resistance of the cured product when the total content of compound A and the metal deactivator is within the above range.

[0093] The total content of compound A, metal deactivator, and curable component is preferably 10 parts by mass or more, preferably 30 parts by mass or more, and preferably 40 parts by mass or more, per 100 parts by mass of solids. This is because, when the total content of compound A, metal deactivator, and curable component is within the above range, the composition has an even better balance of curability and heat resistance of the cured product. The upper limit of the total content of compound A, metal deactivator, and curable component can be appropriately set depending on the application of the composition of this disclosure, but it can be 99 parts by mass or less, preferably 90 parts by mass or less, particularly preferably 80 parts by mass or less, and especially preferably 70 parts by mass or less. This is because, when the content is within the above range, the composition has an even better balance of curability and heat resistance of the cured product.

[0094] The total content of compound A, metal deactivator, and curable component is preferably 50 parts by mass or more, preferably 70 parts by mass or more, and preferably 90 parts by mass or more, per 100 parts by mass of solid content excluding filler, when the composition contains a filler. This is because the composition has an even better balance of curability and heat resistance of the cured product when the total content of compound A, metal deactivator, and curable component is within the above range. The upper limit of the total content of compound A, metal deactivator, and curable component can be set as appropriate depending on the application of the composition of this disclosure, but it can be 99 parts by mass or less, preferably 98 parts by mass or less, and particularly preferably 96 parts by mass or less. This is because the composition has an even better balance of curability and heat resistance of the cured product when the content is within the above range.

[0095] 2. Metal deactivator The above-mentioned metal deactivator can capture metal ions by chelating them, thereby improving the heat resistance of the cured product. The metal ions to be captured here can be any ions that can improve the curability and heat resistance of the composition by capturing them, and examples include alkali metal ions such as sodium and potassium, copper ions, and iron ions. Such metal deactivators can be known metal deactivators, including, for example, benzotriazole compounds, hydrazide compounds, salicylic acid compounds and triazine compounds, oxalic acid compounds, imidazole compounds, phosphite compounds, guanidine compounds, and the like. In this disclosure, it is preferable that the metal deactivator comprises at least one of a benzotriazole compound, a hydrazide compound, a salicylic acid compound, and a triazine compound. This is because the above composition offers a better balance between curability and the heat resistance of the cured product.

[0096] In this disclosure, the metal deactivator is included as a component different from compound A, and typically, with the exception of hydrazide compounds, compounds that do not have a phenolic hydroxyl group protected by a protecting group are used. More specifically, as benzotriazole compounds, salicylic acid compounds, triazine compounds, oxalic acid compounds, imidazole compounds, phosphite compounds, and guanidine compounds used as metal deactivators, compounds that do not have a phenolic hydroxyl group protected by a protecting group are typically used. Furthermore, in this disclosure, hydrazide compounds as metal deactivators may include a portion in which a phenolic hydroxyl group is protected by a protecting group, and compounds having a hydrazine structure are not considered to be compound A.

[0097] Examples of the benzotriazole compounds mentioned above include compounds having a benzotriazole ring, and for example, compounds having both a benzotriazole ring and a hydrazine structure are also considered benzotriazole compounds. In this disclosure, it is preferable that the benzotriazole compound is a compound represented by the following general formula (B1). This is because the above composition has a better balance of curability and heat resistance of the cured product.

[0098] [ka]

[0099] (In the formula, R 1 This represents a hydrogen atom, a hydroxyl group, an unsubstituted or silyl hydrocarbon group with 1 to 20 carbon atoms, or a silyl group with 0 to 20 carbon atoms. R 2 This represents a hydrocarbon group having 1 to 20 carbon atoms, either unsubstituted or with substituents. nb1 represents an integer between 0 and 4.

[0100] R 1 and R 2 The hydrocarbon group used is R 101 Examples include those listed as aliphatic hydrocarbon groups or aromatic hydrocarbon-containing groups used in the above, which satisfy the specified number of carbon atoms. 2 Examples of substituents in hydrocarbon groups having substituents used in this context include R 101 The groups listed above are examples of substituents that can substitute for hydrogen atoms in aliphatic hydrocarbon groups used in applications such as the above. R 1 As the silyl group used to substitute hydrogen atoms in the hydrocarbon group, a silyl group having 0 to 20 carbon atoms can be used. 1 Used in, or R 1 As for the silyl group used to substitute hydrogen atoms in the hydrocarbon group, R 101 Examples of silyl groups used in the above include those that satisfy the specified number of carbon atoms.

[0101] In this disclosure, R 1 However, it is preferable that the hydrocarbon group is substituted with a hydrogen atom, a hydroxyl group, or a silyl group having 1 to 20 carbon atoms. This is because the above composition has a better balance of curability and the heat resistance of the cured product. 1However, in the case of a hydrocarbon group substituted with a silyl group having 1 to 20 carbon atoms, the number of carbon atoms referred to here refers to the number of atoms including the carbon atoms of the silyl group in the hydrocarbon group substituted with the silyl group. 1 However, in the case of a hydrocarbon group substituted with a silyl group having 1 to 20 carbon atoms, a substituted silyl group is preferred, particularly -SiR 117 t (OR 118 ) 3-t The group represented by (R 117 and R 118 Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. t represents an integer from 0 to 3. Preferably, -SiR 117 t (OR 118 ) 3-t It is preferable that the value of t in the middle is 0 or 1, and more preferably that t is 0, i.e., -Si(OR 117 )3 is preferable. This is because the above composition has a better balance of curability and heat resistance of the cured product. Furthermore, R 117 , R 118 However, each of these is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably an alkyl group having 1 to 2 carbon atoms. This is because the above composition has a superior balance of curability and the heat resistance of the cured product. In this disclosure, R 2 However, it is preferable that the hydrogen atom or an unsubstituted hydrocarbon group having 1 to 20 carbon atoms be a hydrogen atom. This is because the above composition has a better balance of curability and the heat resistance of the cured product.

[0102] Examples of the above-mentioned benzotriazole compounds include benzotriazole and toltriazole. Examples of commercially available benzotriazole compounds include X12-1214A manufactured by Shin-Etsu Silicone Co., Ltd.

[0103] The hydrazide compound is a reaction product of a hydrazine compound and an oxo acid, and examples thereof include compounds having a hydrazine structure (-CO-NH-NH-CO-). The hydrazide compound is usually a compound having no benzotriazole ring and further has no salicylic acid structure represented by formula (B3a) described later. In the present disclosure, among others, it is preferable that the hydrazide compound is a compound having a hydrazine structure and a phenolic hydroxyl group, and among others, it is preferable that the compound is represented by the following general formula (B2). This is because the composition is excellent in the balance between curability and heat resistance of the cured product.

[0104]

Chemical formula

[0105] (In the formula, R 3 , R 4 , R 5 and R 6 each independently represents a hydrogen atom or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, R 7 and R 8 each independently represents a hydrocarbon group having 1 to 40 carbon atoms which is unsubstituted or substituted with a substituent, R 9 and R 10Each of these independently consists of a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, an unsubstituted or substituted silyl group having 0 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in an unsubstituted or substituted aliphatic hydrocarbon group where one or more methylene groups are replaced by a divalent group selected from the following groups I-B2, or an unsubstituted group. Alternatively, it represents a group having 6 to 40 carbon atoms in which one or more methylene groups in a substituted aromatic hydrocarbon-containing group are replaced with a divalent group selected from groups I-B2 below; a group having 2 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted heterocyclic-containing group are replaced with a divalent group selected from groups I-B2 below; or a group having 0 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted silyl group are replaced with a divalent group selected from groups I-B2 below. Group I―B2: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 230-B2 -, -NR 230-B2 -CO-, -CO-NR 230-B2 -, -NR 230 -COO-, -OCO-NR 230-B2 - or -SiR 230-B2 R 231-B2 -. R 230-B2 and R 231-B2 Each of these independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 40 carbon atoms.

[0106] R 3 , R 4 , R 5 and R 6 The aliphatic hydrocarbon group used is R 101 Among the aliphatic hydrocarbon groups listed as unsubstituted or substituted for those used in the above, any group that satisfies the specified number of carbon atoms can be used. R 7 and R 8The hydrocarbon group used is a divalent group. Such R 7 and R 8 The hydrocarbon group used is R 101 Etc. or R 104 Examples include aliphatic hydrocarbon groups and aromatic hydrocarbon-containing groups used in the above applications, from which one hydrogen atom has been removed, that satisfy the required number of carbon atoms. R 9 and R 10 For aliphatic hydrocarbon groups, aromatic hydrocarbon-containing groups, heterocyclic-containing groups, and silyl groups used in R 101 Etc. or R 104 Any group similar to those listed as unsubstituted or substituted aliphatic hydrocarbon groups, unsubstituted or substituted aromatic hydrocarbon-containing groups, unsubstituted or substituted heterocyclic-containing groups, or silyl groups, that satisfy the specified number of carbon atoms can be used. R 9 and R 10 For groups used in which an aliphatic hydrocarbon group, an aromatic hydrocarbon-containing group, a heterocyclic-containing group, or a methylene group in a silyl group is replaced with a divalent group selected from group I-B2, R 101 Etc. or R 104 The same groups as those listed above can be used as unsubstituted or substituted aliphatic hydrocarbon groups, aromatic hydrocarbon-containing groups, heterocyclic-containing groups, or silyl groups in which the methylene group is replaced with a divalent group selected from group I. In a group in which two or more methylene groups of the above-mentioned aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group are replaced by divalent groups selected from the above-mentioned groups I-B2, the multiple such divalent groups may be the same or different from each other, but the divalent groups shall not be adjacent to each other. R 230-B2 and R 231-B2 The aliphatic hydrocarbon group used is R 101 Among the unsubstituted aliphatic hydrocarbon groups used in the above, any group that satisfies the specified number of carbon atoms can be used.

[0107] The above R 3 , R 4 , R 5 and R 6 Each of these is independently preferably a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, or a group in which one or more hydrogen atoms of the alkyl group are single-layer substituted with the above-mentioned substituents; that is, each of these is independently preferably a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 40 carbon atoms, more preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 40 carbon atoms, more preferably an alkyl group having 1 to 40 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, particularly preferably an alkyl group having 2 to 6 carbon atoms, and more preferably an alkyl group having 4 carbon atoms represented by -C4H9, and most preferably a tert-butyl group. 3 , R 4 , R 5 and R 6 However, because it is the aforementioned base, the above composition has a better balance of curability and the heat resistance of the cured product. The above R 7 and R 8 Each of these is preferably an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, and more preferably an unsubstituted or substituted alkylene group having 1 to 40 carbon atoms, particularly preferably an unsubstituted or substituted alkylene group having 1 to 10 carbon atoms, and more preferably an unsubstituted or substituted alkylene group having 1 to 5 carbon atoms, and more preferably an unsubstituted alkylene group having 1 to 5 carbon atoms such as a methylene group, ethylene group, propylene group, butylene group, or pentyl group. This is because the above composition has a superior balance of curability and heat resistance of the cured product. R 9 and R 10Preferably, each of these groups is independently a group in which one or more of a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, or a methylene group in an unsubstituted or substituted aliphatic hydrocarbon group is replaced by a divalent group selected from the above groups I-B2. In particular, it is preferable that the hydrogen atom or the methylene group at the oxygen atom end of the unsubstituted or substituted aliphatic hydrocarbon group is replaced by a divalent group selected from the above groups I-B2, and especially, a group having 1 to 40 carbon atoms in which the methylene group at the oxygen atom end of an unsubstituted or substituted alkyl group is replaced by -CO-O-, i.e., -CO-O-R'' -B2 (R'' -B2 It is preferable that the group is represented by an unsubstituted or substituted alkyl group having 1 to 39 carbon atoms. This is because the above composition has a better balance of curability and heat resistance of the cured product. R 9 and R 10 In this context, -CO-O-R'' is used independently. -B2 The base represented by R is 101 The -CO-O-R'' used in the above can be the same as those listed as preferably used groups. Specifically, R 9 and R 10 -CO-O-R'' used in -B2 Preferably, the group is a -CO-O-tert-butyl group. This is because the above composition has a superior balance of curability and heat resistance of the cured product.

[0108] Examples of the above-mentioned hydrazide compounds include N,N'-bis((3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl))propionohydrazide. Examples of commercially available hydrazide compounds include CDA-10 manufactured by ADEKA Corporation, and "Qunox" (registered trademark) manufactured by Mitsui Toatsu Fine Co., Ltd.

[0109] Examples of the salicylic acid compounds mentioned above include compounds having the following structure B3a (where * indicates a bonding site) as a structure derived from salicylic acid. Furthermore, the salicylic acid compounds mentioned above are typically compounds that do not have a benzotriazole ring. In this disclosure, it is preferable that the salicylic acid compound is a compound represented by the following general formulas (B3-1) and (B3-2). This is because the above composition has a superior balance of curability and heat resistance of the cured product.

[0110] [ka]

[0111] [ka]

[0112] (In the formula, R 11 (This represents an aliphatic hydrocarbon group having a hydrogen atom or 1 to 40 carbon atoms, either unsubstituted or substituted.)

[0113] R 11 The aliphatic hydrocarbon group used is R 101 Among the aliphatic hydrocarbon groups listed as unsubstituted or substituted for those used in the above, any group that satisfies the specified number of carbon atoms can be used.

[0114] In this disclosure, R 11 However, it is preferable that the atom is a hydrogen atom or an unsubstituted or substituted alkyl group having 1 to 40 carbon atoms, and more preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, and especially preferably a hydrogen atom. This is because the above composition has a better balance of curability and the heat resistance of the cured product.

[0115] [ka]

[0116] (In the formula, R 12 (This represents a hydrocarbon group with 1 to 40 carbon atoms, either unsubstituted or substituted.)

[0117] R 12 The hydrocarbon group used is a divalent group. Such R 12 The hydrocarbon group used is R 101 Examples include aliphatic hydrocarbon groups used in the above applications and aromatic hydrocarbon-containing groups that are either unsubstituted or substituted, from which one hydrogen atom has been removed, and which satisfy the specified number of carbon atoms.

[0118] In this disclosure, R 12 However, it is preferable that the aliphatic hydrocarbon group has 1 to 40 carbon atoms and is either unsubstituted or substituted, and more preferably that it is an unsubstituted alkylene group having 1 to 40 carbon atoms, particularly preferably an unsubstituted alkylene group having 2 to 20 carbon atoms, particularly preferably an unsubstituted alkylene group having 5 to 15 carbon atoms, and particularly preferably an unsubstituted alkylene group having 7 to 13 carbon atoms. This is because the above composition has a better balance between curability and the heat resistance of the cured product.

[0119] Examples of the salicylic acid compounds mentioned above include 3-(N-salicyloyl)amino-1,2,4-triazole, decamethylenedicarboxylic acid disalicyloylhydrazide, and salicylidene salicyloylhydrazine. Examples of commercially available salicylic acid compounds include ADEKA CDA-1 and ADEKA CDA-6S manufactured by ADEKA Corporation, and Chel-180 manufactured by BASF.

[0120] Examples of the above-mentioned triazine compounds include compounds having a triazine ring. The triazine compounds used are typically those that do not have a benzotriazole ring, a hydrazine structure, or the structure represented by formula (B3a) above. In this disclosure, the triazine compound is preferably a compound represented by the following general formula (B4). This is because the above composition has a better balance of curability and heat resistance of the cured product.

[0121] [ka]

[0122] (In the formula, R 14 This indicates a single bond or a linking group. R 13-1 , R 13-2 , R 13-3 and R 13-4 Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. R 15-1 and R 15-2 Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, or a methoxy group. R 16 This includes hydrogen atoms, C1-C4 alkyl groups, hydroxyl groups, methoxy groups, or -SiR 17 s (OR 18 ) 3-s This indicates the group represented by [the symbol]. R 17 and R 18 Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. nb4 represents an integer between 0 and 16. s represents an integer between 0 and 3.

[0123] R 13-1 , R 13-2 , R 13-3 and R 13-4 , R 15-1 and R 15-2 , R 16 R 17 and R 18 The alkyl groups used are, independently, R 101 Examples of alkyl groups used in the above include those that satisfy the specified number of carbon atoms. R 14 Examples of linking groups used include unsubstituted or substituted hydrocarbon groups with 1 to 40 divalent carbon atoms, carbonyl groups, ether bonds, ester bonds, carbonate groups, amide groups, thioether groups, amino groups, and groups formed by linking multiple such groups. As for divalent hydrocarbon groups with 1 to 40 carbon atoms, R 101 Examples include aliphatic hydrocarbon groups used in the above applications and aromatic hydrocarbon-containing groups that are either unsubstituted or substituted, from which one hydrogen atom has been removed, and which satisfy the specified number of carbon atoms. Examples of carbonyl groups, ether bonds, ester bonds, carbonate groups, amide groups, thioether groups, amino groups, and groups formed by linking multiple of these groups include -CO-, -O-CO-O-, -COO-, -O-, -CONH-, -S-, -NH-, and groups formed by linking one or more of these groups with one or more divalent hydrocarbon groups.

[0124] In this disclosure, the above R 13-1 , R 13-2 , R 13-3 and R 13-4 However, each is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and more preferably a hydrogen atom. This is because the above composition has a superior balance of curability and the heat resistance of the cured product. Note, R 13-1 , R 13-2 , R 13-3 and R 13-4 The groups may be the same or different, but it is preferable that they be the same. This is because the above composition has a better balance of curability and the heat resistance of the cured product. In this disclosure, the above R 15-1 and R 15-2 However, each is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and more preferably a hydrogen atom. This is because the above composition has a superior balance of curability and the heat resistance of the cured product. Note that if nb4 is 2 or more, multiple R15-1 These may be the same group or different groups. Similarly, if nb4 is 2 or more, multiple R 15-2 These may be the same group or different groups. In this disclosure, the above R 16 However, hydrogen atoms, hydroxyl groups, methoxy groups, or -SiR 17 s (OR 18 ) 3-s It is preferable that the group is represented by , and among them, a hydroxyl group or -SiR 17 s (OR 18 ) 3-s This is preferable because the above composition offers an even better balance between curability and the heat resistance of the cured product. In this disclosure, R 16 -SiR used in 17 s (OR 18 ) 3-s It is preferable that the value of s in the expression is 0 or 1, and more preferably that s is 0, i.e., -Si(OR 17 )3 is preferable. This is because the above composition has a superior balance of curability and heat resistance of the cured product. In this disclosure, R 17 , R 18 However, each of these is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably an alkyl group having 1 to 2 carbon atoms. This is because the above composition has a superior balance of curability and the heat resistance of the cured product. Linking group R 14 Preferably, the group is a divalent hydrocarbon group, and more preferably, a divalent aliphatic hydrocarbon group, and in particular, an alkylene group, which is an alkyl group from which one hydrogen atom has been removed from an alkyl group. Linking group R 14 However, if it is a divalent hydrocarbon group, R 14The number of carbon atoms in is preferably 2 or more, and preferably 3 or more. A group linked to is preferred, and -S-;-NH-; or -CH2CH2-S- is particularly preferred. This is because the above composition has a better balance of curability and heat resistance of the cured product.

[0125] In this disclosure, nb4 is preferably an integer between 1 and 8, more preferably an integer between 1 and 6, and particularly preferably an integer between 1 and 3. This is because the above composition has a better balance of curability and heat resistance of the cured product.

[0126] Specifically, the triazine compound described in Japanese Patent Publication No. 2020-70391 as a triazine-based adhesive (D) can be used. Examples of commercially available triazine compounds include those with the trade names "VD-3," "VD-4," and "VD-5" (all manufactured by Shikoku Chemicals Co., Ltd.).

[0127] Examples of the oxalic acid compounds mentioned above include compounds having a structure derived from oxalic acid (for example, -CO-CO-).

[0128] As the oxalic acid compound mentioned above, for example, those described as oxalic acid derivatives in Japanese Patent Publication No. 6266964 can be used.

[0129] Examples of the oxalic acid compounds mentioned above include oxalo-bis-1,2-hydroxybenzylidenehydrazide (N,N'-bis(2-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethylcarbonyloxy)ethyl)oxamide, oxalic acid anilide, and N-(2-ethylphenyl)-N'-(2-ethoxyphenyl)oxalic acid diamide. Examples of commercially available oxalic acid compounds include Eastman Inhibitor, OABH from Eastman Kodak and Naugard XL-1 from Uniroyal Chemicals.

[0130] Examples of the above-mentioned imidazole compounds include 4,4'-methylenebis(2-undecyl-5-methylimidazole) and bis[(N-methyl)imidazole-2-yl]carbinol octyl ether.

[0131] Examples of the above-mentioned phosphite compounds include tris(2-tert-butyl-5-methyl-4-thio-5'-tert-butyl-4'-hydroxy-2-methylphenyl)phenylphosphite and tris[2-tert-butyl-4-thio(2'-methyl-4'-hydroxy-5'-tert-butyl)phenyl-5-methyl]phenylphosphite.

[0132] Examples of the above guanidine compounds include guanidine hydrochloride, guanidine nitrate, guanidine carbonate, guanidine phosphate, and guanidine sulfamate as guanidine salts.

[0133] The content of the metal deactivator is preferably 5 parts by mass or more and 90 parts by mass or less, more preferably 10 parts by mass or more and 80 parts by mass or less, particularly preferably 15 parts by mass or more and 60 parts by mass or less, and more preferably 20 parts by mass or more and 50 parts by mass or less, based on 100 parts by mass of the total of compound A and the metal deactivator. This is because the composition has an even better balance of curability and heat resistance of the cured product when the content is within the above range.

[0134] The amount of the metal deactivator can be set appropriately depending on the intended use of the composition, as long as it provides the desired curability and heat resistance of the cured product. The content of the above-mentioned metal deactivator is preferably, for example, 0.01 parts by mass or more and 20 parts by mass per 100 parts by mass of solid content of the above composition, more preferably 0.05 parts by mass or more and 10 parts by mass, and particularly preferably 0.1 parts by mass or more and 5 parts by mass. This is because the above-mentioned content within the above range results in a more excellent balance between curability and the heat resistance of the cured product of the above composition. The term "solids" refers to all components except the solvent.

[0135] The content of the above-mentioned metal deactivator varies depending on the content of the solvent, etc., but for example, it is preferably 0.001 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the composition, more preferably 0.005 parts by mass or more and 10 parts by mass or less, and particularly preferably 0.01 parts by mass or more and 5 parts by mass or less. This is because the above-mentioned content is within the above range, resulting in a better balance between curability and the heat resistance of the cured product of the composition.

[0136] The content of the above-mentioned metal deactivator is preferably 0.01 parts by mass or more and 20 parts by mass or less in 100 parts by mass of the total of compound A, the metal deactivator, and the curable component, more preferably 0.05 parts by mass or more and 10 parts by mass or less, particularly preferably 0.1 parts by mass or more and 5 parts by mass or less, and especially preferably 0.5 parts by mass or more and 3 parts by mass or less. This is because the above-mentioned composition has an even better balance between curability and the heat resistance of the cured product when the content of compound A is within the above range.

[0137] 3.Curing component The above-mentioned curable component consists of a curable compound. Furthermore, the curable component is included in the composition as a component other than compound A and the metal deactivator, and compounds A and metal deactivators that are polymerizable are not included in the curable component. Therefore, compounds A that contain alkenyl groups, etc., do not fall under the category of curable component in this disclosure. As the curable compound mentioned above, a compound capable of forming a high molecular weight by bonding two or more curable compounds can be used. Examples include radical polymerizable compounds that can be directly bonded to each other to achieve high molecular weight, and thermosetting compounds that can be heated to achieve high molecular weight. In this disclosure, it is preferable that the curable component includes a radical polymerizable compound, as this further enhances the effect of obtaining a composition with an excellent balance between curability and the heat resistance of the cured product. Furthermore, in this disclosure, it is also preferable that the curable component includes both a radical polymerizable compound and a thermosetting compound. This is because the above composition has an excellent balance between curability and the heat resistance of the cured product.

[0138] The above-mentioned radical polymerizable compound may be any compound capable of radical polymerization. Examples of the above-mentioned radical polymerizable compound include compounds having ethylenically unsaturated groups such as acrylic groups, methacrylic groups, and vinyl groups. In the compositions of this disclosure, as compounds having one or more ethylenically unsaturated groups, monofunctional compounds having one ethylenically unsaturated group and polyfunctional compounds having two or more ethylenically unsaturated groups can be used. Known compounds can be used as the above-mentioned radical polymerizable compound, for example, radical polymerizable compounds described in International Publication No. 2018 / 012383 and radical polymerizable organic substances described in International Publication No. 2014 / 021023 can be used.

[0139] As the radical polymerizable compound mentioned above, it is preferable to use a compound having an acidic group such as a carboxyl group and an ethylenically unsaturated group, from the viewpoint of being able to impart alkali developability. Examples of compounds having an acidic group such as a carboxyl group and an ethylenically unsaturated group include unsaturated carboxylic acids such as acrylic acid and methacrylic acid, and carboxyl group-containing resins.

[0140] Examples of carboxyl group-containing resins that can be used include the carboxyl group-containing photosensitive resin described in Japanese Patent Publication No. 2016-180880, the carboxyl group-containing resin described in International Publication No. 2016 / 208187, the carboxyl group-containing resin described in Japanese Patent Publication No. 2017-11453, the carboxyl group-containing resin described in Japanese Patent Publication No. 2018-53215, the polymer containing structural units having carboxyl groups described in Japanese Patent Publication No. 2016-151744, and the [A] copolymer described in Japanese Patent Publication No. 2005-234362. Examples of the carboxyl group-containing resins mentioned above include epoxy acrylate resins obtained by reacting a cresol novolac type epoxy resin with acrylic acid or methacrylic acid; acid-modified unsaturated epoxy ester resins obtained by reacting a polyfunctional epoxy compound with an unsaturated carboxylic acid and then with a polybasic acid or its anhydride; and unsaturated modified acrylic resins obtained by introducing ethylenically unsaturated groups into an acrylic resin having a structural unit obtained by polymerizing a compound selected from acrylic acid and methacrylic acid by reacting it with an epoxy compound containing ethylenically unsaturated groups.

[0141] The above-mentioned polyfunctional epoxy compound may be any compound having at least two epoxy groups in one molecule. Examples of such polyfunctional epoxy compounds include bisphenol-type epoxy resins such as bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, and bisphenol AD-type epoxy resin; biphenyl-type epoxy resin, naphthalene-type epoxy resin, dicyclopentadiene-type epoxy resin, rubber-modified epoxy resins such as silicone-modified epoxy resin; ε-caprolactone-modified epoxy resin; phenol novolac-type epoxy resins such as bisphenol A-type, bisphenol F-type, and bisphenol AD-type; cresol novolac-type epoxy resins such as o-cresol novolac-type; cyclic aliphatic polyfunctional epoxy resin; glycidyl ester-type polyfunctional epoxy resin; glycidylamine-type polyfunctional epoxy resin; heterocyclic polyfunctional epoxy resin; bisphenol-modified novolac-type epoxy resin; polyfunctionally modified novolac-type epoxy resin; and condensate-type epoxy resins of phenols and aromatic aldehydes having phenolic hydroxyl groups. Furthermore, resins into which halogen atoms such as Br and Cl have been introduced can also be used. The polyfunctional epoxy compound may be a glycidyl-type epoxy compound having a glycidyl group, or it may be an epoxy compound having a cycloalkene oxide structure. These polyfunctional epoxy compounds may be used individually or in combination of two or more.

[0142] Examples of the unsaturated carboxylic acids mentioned above include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and cinnamic acid. Among these unsaturated monocarboxylic acids, acrylic acid or methacrylic acid is preferred. This is because the above composition has an even better balance between curability and the heat resistance of the cured product. The method for reacting a polyfunctional epoxy compound with an unsaturated monocarboxylic acid is not particularly limited; for example, the reaction can be carried out by heating the polyfunctional epoxy compound and the unsaturated monocarboxylic acid in a suitable solvent.

[0143] Both polysaturated and unsaturated polybasic acids or their anhydrides can be used as the above-mentioned polybasic acids. Examples of the polybasic acids mentioned above include succinic acid, maleic acid, adipic acid, citric acid, phthalic acid, tetrahydrophthalic acid, 3-methyltetrahydrophthalic acid, 4-methyltetrahydrophthalic acid, 3-ethyltetrahydrophthalic acid, 4-ethyltetrahydrophthalic acid, hexahydrophthalic acid, 3-methylhexahydrophthalic acid, 4-methylhexahydrophthalic acid, 3-ethylhexahydrophthalic acid, 4-ethylhexahydrophthalic acid, methyltetrahydrophthalic acid, methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, methylendomethylenetetrahydrophthalic acid, trimellitic acid, pyromellitic acid, and diglycolic acid. Examples of the polybasic acid anhydrides mentioned above include the anhydrides of the polybasic acids mentioned above.

[0144] Examples of the epoxy compounds containing the ethylenically unsaturated group mentioned above include glycidyl methacrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, and 3,4-epoxycyclohexylmethyl (meth)acrylate.

[0145] Note that the (meth)acrylic group includes both the acrylic group and the methacrylic group. Furthermore, (meth)acrylate includes both acrylate and methacrylate.

[0146] Commercially available carboxyl group-containing resins can be used. Examples of such commercially available carboxyl group-containing resins include ZAR-2000, ZFR-1122, FLX-2089, ZCR-1601H, CCR-1171H, CCR-1235, CCR-1291H, CCR-1307H, CCR-1309H (all manufactured by Nippon Kayaku Co., Ltd.), Cyclomer P(ACA)Z-250 (manufactured by Daicel Chemical Industries, Ltd.), Lipoxy SP-4621, SPC-1000, SPC-3000, PR-300CP (manufactured by Showa Polymer Co., Ltd.), and the like.

[0147] The acid value of the carboxyl group-containing resin described above should be a value that allows for the formation of a cured product with excellent durability. For example, it is preferably 40 mg KOH / g or more and 150 mg KOH / g or less, and more preferably 50 mg KOH / g or more and 130 mg KOH / g or less. This is because, when the acid value of the carboxyl group-containing resin is within the above range, the above composition easily forms a cured product with excellent durability. Furthermore, the above composition is easy to pattern.

[0148] The weight-average molecular weight of the carboxyl group-containing resin can be any weight that yields a cured product with excellent durability, but a weight-average molecular weight of 1,000 or more can be used. The weight-average molecular weight of the carboxyl group-containing resin is preferably, for example, 2,000 to 150,000, and more preferably 5,000 to 100,000, from the viewpoint of facilitating patterning. This is because, when the average molecular weight of the carboxyl group-containing resin is within the above range, the composition can easily form a cured product with excellent durability. Furthermore, the composition is easy to pattern. The weight-average molecular weight Mw of the above-mentioned carboxyl group-containing resin can be obtained, for example, by using HLC-8120GPC manufactured by Tosoh Corporation, with N-methylpyrrolidone with 0.01 mol / liter of lithium bromide added as the elution solvent, and using polystyrene standards for calibration curves with Mw 377,400, 210,500, 96,000, 50,400, 20,650, 10,850, 5,460, 2,930, 1,300, and 580 (all from Polymer Laboratories' Easi PS-2 series) and Mw 1,090,000 (manufactured by Tosoh Corporation), and measuring with two TSK-GEL ALPHA-M columns (manufactured by Tosoh Corporation). The measurement temperature can be 40°C and the flow rate can be 1.0 mL / min.

[0149] The content of the radical polymerizable compound having the carboxyl group described above can be any compound capable of forming a cured product with excellent durability. For example, it is preferably 1 to 90 parts by mass, more preferably 20 to 80 parts by mass, and preferably 30 to 70 parts by mass per 100 parts by mass of solid content of the composition. This is because the composition can easily form a cured product with excellent curability and heat resistance. Furthermore, it is because the composition can easily form patterns.

[0150] Among the radical polymerizable compounds described above, those without a carboxyl group (hereinafter sometimes referred to as compounds without a carboxyl group) may also be used. As a compound without a carboxyl group, for example, a compound represented by the following general formula (1) can be preferably used. This is because using such a compound results in a better balance between curability and the heat resistance of the cured product of the composition of this disclosure.

[0151] [ka]

[0152] (In the formula, R 111 This represents a hydrogen atom or a methyl group. X 1This represents an aliphatic hydrocarbon group having 1 to 40 carbon atoms and having the same valence as n1, either unsubstituted or substituted; an aromatic hydrocarbon-containing group having 6 to 40 carbon atoms and having the same valence as n1, either unsubstituted or substituted; a heterocyclic-containing group having 2 to 40 carbon atoms and having the same valence as n1, either unsubstituted or substituted; or a group having 1 to 40 carbon atoms in which one or more methylene groups in an aliphatic hydrocarbon group having the same valence as n1 are replaced by a divalent group selected from Group I above; a group having 6 to 40 carbon atoms in an aromatic hydrocarbon-containing group having the same valence as n1, either unsubstituted or substituted, either replaced by a divalent group selected from Group I above; or a group having 2 to 40 carbon atoms in a heterocyclic-containing group having the same valence as n1, either unsubstituted or substituted, either replaced by a divalent group selected from Group I above. n1 represents an integer between 1 and 10.

[0153] X 1 An aliphatic hydrocarbon group represented by having the same valency as n1, either unsubstituted or substituted; an aromatic hydrocarbon-containing group having the same valency as n1, either unsubstituted or substituted; and a heterocyclic-containing group having the same valency as n1, either unsubstituted or substituted. Examples of groups in which one or more methylene groups in the above-mentioned aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group are replaced by divalent groups selected from group I include groups similar to X in the above-mentioned general formula (A1).

[0154] From the viewpoint of achieving superior curability of the composition, n1 is preferably an integer between 2 and 8, more preferably an integer between 3 and 7, and particularly preferably an integer between 4 and 6. This is because the effect of achieving superior heat resistance in the resulting cured product can be more effectively demonstrated. In this disclosure, X in general formula (1) 1Preferably, the group is an aliphatic hydrocarbon group, or a group in which one or more methylene groups in an aliphatic hydrocarbon group are replaced with a divalent group selected from the above group I, and more preferably, the group is in which one or more methylene groups in an aliphatic hydrocarbon group are replaced with a divalent group selected from -O-, -COO-, and -CO-, and in particular, the group is in which one or more methylene groups in an aliphatic hydrocarbon group are replaced with a divalent group selected from -O-. This is because the effect of having a better heat resistance in the resulting cured product can be exhibited more effectively. In this disclosure, X in general formula (1) 1 When the group is an aliphatic hydrocarbon group, or a group in which one or more methylene groups in an aliphatic hydrocarbon group are replaced with a divalent group selected from group I above, it is preferable that the aliphatic hydrocarbon group used is an alkyl group from which n1-1 hydrogen atoms have been removed. This is because the effect of having better heat resistance in the resulting cured product can be exhibited more effectively. In this disclosure, X in general formula (1) 1 If is an aliphatic hydrocarbon group, or a group in which one or more methylene groups in an aliphatic hydrocarbon group are replaced by a divalent group selected from group I above, then X 1 The number of carbon atoms is preferably 2 to 30, more preferably 4 to 20, and especially preferably 6 to 15. This is because the effect of having better heat resistance in the resulting cured product can be more effectively exhibited.

[0155] The above-mentioned compounds that do not have a carboxyl group can be any compounds that have one or more ethylenically unsaturated groups and do not have a carboxyl group. Examples include compounds obtained by adding an α,β-unsaturated carboxylic acid to a polyhydric alcohol, and compounds obtained by adding an α,β-unsaturated carboxylic acid to a glycidyl group-containing compound. For such compounds, for example, those described in (D) Reactive Diluents in Japanese Patent Publication No. 2018-053215 can be used. Specifically, the compounds that do not have the above-mentioned carboxyl group include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, isobutyl acrylate, n-octyl acrylate, isooctyl acrylate, isononyl acrylate, stearyl acrylate, methoxyethyl acrylate, dimethylaminoethyl acrylate, zinc acrylate, 1,4-butanediol diacrylate, neopentyl glycol diacrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, butyl methacrylate, tert-butyl methacrylate, cyclohexyl methacrylate, and 1,4-butanediol diacrylate. Examples include methacrylate, neopentyl glycol dimethacrylate, trimethylolpropane trimethacrylate, polyethylene glycol di(meth)acrylate, isocyanurate di(meth)acrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate, bisphenol A diglycidyl ether (meth)acrylate, bisphenol F diglycidyl ether (meth)acrylate, bisphenol Z diglycidyl ether (meth)acrylate, and tripropylene glycol di(meth)acrylate. As radical polymerizable compounds that do not have the carboxyl group mentioned above, (meth)acrylates having a phosphate ester structure such as mono(2-acryloyloxyethyl) acid phosphate can also be used. As radical polymerizable compounds that do not have the carboxyl group mentioned above, urethane acrylates, polyester acrylates, and epoxy acrylates can also be used. As commercially available products of such urethane acrylates, polyester acrylates, and epoxy acrylates, for example, those described in Japanese Patent Application Publication No. 2018-53215 can be used.

[0156] Among the compounds that do not have a carboxyl group, those that are liquid at room temperature (25°C) may be used as a diluent for dissolving the carboxyl group-containing resin, etc.

[0157] When the above-mentioned radical polymerizable component contains a compound having an acidic group such as a carboxyl group as a radical polymerizable compound, it is preferable to use a compound having an acidic group and a compound without an acidic group in combination. For example, when the above-mentioned radical polymerizable component contains a compound having a carboxyl group as a radical polymerizable compound, it is preferable to use a compound having a carboxyl group and a compound without a carboxyl group in combination. This is because it results in an excellent balance between the curability of the composition, the heat resistance of the cured product, and the alkali developability.

[0158] When the above curable component includes both compounds having acidic groups such as carboxyl groups and compounds not having acidic groups such as carboxyl groups as radical polymerizable compounds, the content of the radical polymerizable compounds not having acidic groups is preferably 1 to 90 parts by mass, more preferably 5 to 40 parts by mass, and particularly preferably 10 to 25 parts by mass, per 100 parts by mass of the total of the radical polymerizable compounds having acidic groups and the radical polymerizable compounds not having acidic groups. This is because the above composition will have excellent curability and the resulting cured product will have excellent heat resistance. Furthermore, this will allow for easier pattern formation with the above composition.

[0159] The content of the radical polymerizable component in the composition of the present invention is preferably 10 parts by mass or more and 80 parts by mass, more preferably 20 parts by mass or more and 70 parts by mass, more preferably 30 parts by mass or more and 60 parts by mass, and particularly preferably 40 parts by mass or more and 50 parts by mass, per 100 parts by mass of solid content of the composition. This is because the composition will have excellent curability and the resulting cured product will have excellent heat resistance. In this specification, thermosetting compounds do not include compounds having radical polymerizability, and compounds that have thermosetting properties but also radical polymerizability are not considered thermosetting compounds but are included in radical polymerizable compounds.

[0160] As the thermosetting compound mentioned above, compounds other than those that undergo high molecular weight conversion by radicals can be used. Furthermore, it is preferable that the thermosetting compound is one that can undergo high molecular weight conversion at temperatures of 25°C or higher, because it makes it easier to set the curing conditions. Examples of the above-mentioned thermosetting compounds include phenolic resins, urea resins, amino resins, epoxy compounds such as polyfunctional epoxy compounds, cyclic ether compounds such as polyfunctional oxetane compounds, unsaturated polyester resins, benzoguanamine derivatives, isocyanate compounds, blocked isocyanate compounds, maleimide compounds, benzoxazine compounds, oxazoline compounds, carbodiimide compounds, cyclocarbonate compounds, polyfunctional oxetane compounds, and cyclic thioether compounds such as episulfide resins. As the polyfunctional epoxy compound described above, the same one used as an example for forming the carboxyl group-containing resin can be used. As a commercially available product of the polyfunctional epoxy compound described above, for example, the one described in Japanese Patent Application Publication No. 2018-53215 can be used. As the above-mentioned isocyanate compound, blocked isocyanate compound, polyfunctional oxetane compound, and episulfide resin, for example, compounds having an isocyanate group or a blocked isocyanate group as described in Japanese Patent Application Publication No. 2017-111453, polyfunctional oxetane compounds, and resins in which the oxygen atoms of the epoxy groups of a novolac-type epoxy resin are replaced with sulfur atoms can be used. As the above-mentioned amino resin, for example, melamine derivatives, benzoguanamine derivatives, etc., described in Japanese Patent Publication No. 2017-111453 can be used. In this disclosure, the thermosetting compound preferably includes cyclic ether compounds, cyclic thioether compounds, etc., and more preferably includes cyclic ether compounds, and more preferably includes epoxy compounds, and more preferably includes polyfunctional epoxy compounds. This is because the above composition has an excellent balance between curability and the heat resistance of the cured product.

[0161] The content of the thermosetting compound in the composition of the present invention is preferably 1 to 50 parts by mass, more preferably 5 to 40 parts by mass, and particularly preferably 8 to 20 parts by mass, per 100 parts by mass of solid content of the composition. This is because the composition will have excellent curability and the resulting cured product will have excellent heat resistance. The content of the thermosetting compound in the composition of the present invention is preferably 5 to 60 parts by mass, more preferably 10 to 40 parts by mass, and particularly preferably 15 to 30 parts by mass, based on 100 parts by mass of the total of the radical polymerizable component and the thermosetting compound. This is because the above composition has excellent curability and the resulting cured product has excellent heat resistance.

[0162] The content of the curable component in the composition of this disclosure is set appropriately according to the intended use of the composition. Preferably, the content of the curable component is 5 parts by mass or more per 100 parts by mass of solid content of the composition, more preferably 20 parts by mass or more, and particularly preferably 30 parts by mass or more and 99 parts by mass or less. This is because the composition has an excellent balance between curability and the heat resistance of the cured product when the content is within the above range. The term "solids" refers to all components except the solvent. The content of the curable component varies depending on the content of the solvent, etc., but for example, it is preferably 1 part by mass or more and 99 parts by mass per 100 parts by mass of the composition, more preferably 10 parts by mass or more and 90 parts by mass, and particularly preferably 30 parts by mass or more and 80 parts by mass. This is because the composition has an excellent balance between curability and the heat resistance of the cured product when the content is within the above range. The content of the curable component is preferably 60 parts by mass or more, in a total of 100 parts by mass of compound A, the metal deactivator, and the curable component, and more preferably 90 parts by mass or more and 99.5 parts by mass or less, and particularly preferably 95 parts by mass or more and 99 parts by mass or less. This is because the composition has an excellent balance between curability and the heat resistance of the cured product when the content of the curable component is within the above range.

[0163] 4.Curing catalyst The above composition may include a curing catalyst in addition to the curing component. The curing catalyst can be any catalyst that promotes the curing reaction of the curable component and facilitates the formation of a high molecular weight material in which two or more curable compounds are bonded together. It can be appropriately selected depending on the type of curable component, the intended use of the composition, etc. If the curing catalyst contains a radical polymerization initiator, each curing component may also contain a radical polymerization initiator.

[0164] As radical polymerization initiators, for example, photoradical polymerization initiators of acetophenone compounds, benzyl compounds, benzophenone compounds, thioxanthone compounds, and oxime ester compounds described in International Publication No. 2018 / 012383, etc., as well as thermal radical polymerization initiators such as azo compounds, peroxides, and persulfates, can be used. In addition, as radical polymerization initiators, acetophenone compounds, benzyl compounds, benzophenone compounds, thioxanthone compounds, bisimidazole compounds, acridine compounds, acylphosphine compounds, etc., described in International Publication No. 2017 / 170493, International Publication No. 2019 / 013112, etc., can also be used.

[0165] The content of the radical polymerization initiator in the composition of this disclosure may be any amount that provides the desired curability. For example, it is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, per 100 parts by mass of the radical polymerizable compound included as a curable component. This is because a composition with an excellent balance between curability and the heat resistance of the cured product can be obtained by having the above content within the above range.

[0166] When the curing catalyst contains a thermosetting compound as a curing component, such as a polyfunctional epoxy compound, a cyclic ether compound such as a polyfunctional oxetane compound, or a cyclic thioether compound having multiple cyclic thioether groups such as an episulfide resin, it is preferable to include a thermosetting agent capable of forming a high molecular weight of the above thermosetting compound. This is because the above composition has an even better balance between curability and the heat resistance of the cured product.

[0167] Examples of the above-mentioned thermosetting agents include melamine derivatives, imidazole derivatives, amine compounds such as dicyandiamide, hydrazine compounds, phosphorus compounds, S-triazine derivatives, polymercaptans, acid anhydrides, phenolic resins, and carboxylic acid compounds.

[0168] Examples of such thermosetting agents and commercially available products thereof include those described as thermosetting catalysts, etc., in Japanese Patent Publication No. 2017-111453.

[0169] Furthermore, as melamine derivatives, those listed as thermosetting components in Japanese Patent Publication No. 2017-111453 can be used. Specifically, examples of melamine derivatives include methylolmelamine compounds, methylolbenzoguanamine compounds, methylol glycoluryl compounds, methylolurea compounds, alkoxymethylated melamine compounds, alkoxymethylated benzoguanamine compounds, alkoxymethylated glycoluryl compounds, and alkoxymethylated urea compounds. The type of alkoxymethyl group is not particularly limited and can be, for example, a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, a butoxymethyl group, etc. In this disclosure, the melamine derivative is preferably an alkoxyalkylated melamine compound. This is because the composition has an excellent balance of curability and heat resistance of the cured product. Examples of commercially available melamine derivatives include Nikalac Mx-750, Mx-032, Mx-270, Mx-280, Mx-290, Mx-706, Mx-708, Mx-40, Mx-31, Ms-11, Mw-30, Mw-30HM, Mw-390, Mw-100LM, and Mw-750LM (all manufactured by Sanwa Chemical Co., Ltd.).

[0170] In this disclosure, the thermosetting agent is preferably an amine compound, and among these, melamine derivatives, dicyandiamides, etc. This is because the above compositions have an excellent balance between curability and the heat resistance of the cured product.

[0171] The content of the above-mentioned thermosetting agent can be any amount that provides the desired curability. For example, it can be 0.1 parts by mass or more and 50 parts by mass or less per 100 parts by mass of the total thermosetting composition described above, and more preferably 0.1 parts by mass or more and 50 parts by mass or less per 100 parts by mass of the total cyclic ether compound and cyclic thioether compound described above. This is because a composition with an excellent balance between curability and the heat resistance of the cured product can be obtained by having the content of the above-mentioned thermosetting agent within the above range.

[0172] In the present invention, the preferred amount of curing catalyst is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 10 parts by mass or less, per 100 parts by mass of the curable component. This is because a composition with an excellent balance between curability and the heat resistance of the cured product can be obtained by having the curing catalyst content within the above range.

[0173] 5. Solvent The compositions disclosed herein may include compound A, a metal deactivator, and a solvent for dispersing or dissolving the curable component. The above solvent can be in liquid form at room temperature (25°C) and atmospheric pressure. The solvent described above is capable of dispersing or dissolving each component in the composition, such as compound A, the metal deactivator, and the curing component. Therefore, even when liquid at room temperature (25°C) and atmospheric pressure, compound A, the metal deactivator, and the curing component are not contained in the solvent. Any of the solvents that can be used is water, an organic solvent, or a mixture thereof.

[0174] As organic solvents, known solvents can be used, such as carbonates like propylene carbonate; ketones like methyl ethyl ketone; ether solvents like ethyl ether; ester solvents like methyl acetate; alcohol solvents like methanol and ethanol; ether ester solvents like propylene glycol-1-monomethyl ether-2-acetate; BTX solvents like benzene; and aliphatic hydrocarbon solvents like hexane. As organic solvents, for example, solvents that can dissolve or disperse each component in a curable composition, as described in International Publication No. 2018 / 012383, and organic solvents, as described in International Publication No. 2014 / 021023, can also be used.

[0175] The solvent content in the composition of this disclosure should be such that a composition with an excellent balance of curability and heat resistance of the cured product is obtained. The solvent content can be 1 part by mass or more and 99 parts by mass or less per 100 parts by mass of the composition, and more preferably 10 parts by mass or more and 50 parts by mass or less, and more preferably 20 parts by mass or more and 45 parts by mass or less. This is because the solvent content being within the above range makes it easy to adjust the coating properties and other aspects of the composition.

[0176] 6. Filler The above composition preferably includes a filler in addition to compound A, a metal deactivator, a curable component, a curing catalyst, and a solvent. The inclusion of a filler improves the composition's properties, such as insulation, making it suitable for use as a solder resist in printed circuit boards and the like. More specifically, the above-mentioned fillers can be those used in solder resists, and can include inorganic and organic fillers. As the inorganic fillers mentioned above, those incorporated into sealing materials such as silicone resin compositions and epoxy resin compositions can be used. Examples include silicas such as fused silica, fused spherical silica, crystalline silica, colloidal silica, fumed silica, and silica gel; metal oxides such as alumina, iron oxide, titanium oxide, and antimony trioxide; ceramics such as silicon nitride, aluminum nitride, boron nitride, and silicon carbide; minerals such as mica and montmorillonite; metal hydroxides such as aluminum hydroxide and magnesium hydroxide, or those modified by organic modification treatment; metal carbonates such as calcium carbonate, calcium silicate, magnesium carbonate, and barium carbonate; metal salts such as barium sulfate, or those modified by organic modification treatment; pigments such as metal borate and carbon black; and carbon fibers, graphite, whiskers, kaolin, talc, glass fibers, glass beads, glass microspheres, silica glass, layered clay minerals, clay, silicon carbide, quartz, aluminum, and zinc. Examples of the above-mentioned organic fillers include acrylic beads, polymer microparticles, transparent resin beads, wood powder, pulp, and cotton chips. In this disclosure, the inorganic filler is preferably silicas, metal oxides, metal salts, or talc, and particularly preferably crystalline silica, talc, barium sulfate, or titanium oxide. This is because the above compositions result in cured products with excellent heat resistance.

[0177] The average particle size of the filler described above can be any size that provides the desired durability and varies depending on the application of the composition. For example, in the case of solder resist applications, it is preferable to have a particle size of 10 nm to 100 μm. This is because the composition results in a cured product with excellent heat resistance. Furthermore, the laser diffraction / scattering method can be used as the method for measuring the average particle size described above. Specifically, a laser diffraction particle size distribution analyzer (such as the SALD-2000J manufactured by Shimadzu Corporation) can be used. The average particle size can be defined as the particle size (median diameter) at which the cumulative particle size distribution reaches 50% from the finest particle side, based on the number of particles.

[0178] The content of the filler is preferably, for example, 5 to 500 parts by mass per 100 parts by mass of the curable component, more preferably 5 to 200 parts by mass, and more preferably 10 to 150 parts by mass. This is because a composition with an excellent balance between curability and the heat resistance of the cured product can be obtained by having the filler content within the above range. Furthermore, it facilitates the formation of a cured product with excellent durability, making it easy to use, for example, in solder resists. The content of the filler is preferably, for example, 1 to 90 parts by mass per 100 parts by mass of solid content of the composition, more preferably 5 to 70 parts by mass, more preferably 10 to 60 parts by mass, and more preferably 20 to 40 parts by mass. This is because a composition with an excellent balance of curability and heat resistance of the cured product can be obtained by having the content within the above range. Furthermore, it becomes easier to form a cured product with excellent durability, making it easy to use, for example, in solder resists.

[0179] 7. Other ingredients In addition to compound A, a metal deactivator, a curable component, a curing catalyst, a solvent, and a filler, the above composition may optionally contain other components. Other components can be selected depending on the intended use of the composition, and examples include: benzotriazole, triazine, and benzoate-based ultraviolet absorbers; phenol-based and phosphorus-based antioxidants; antistatic agents consisting of cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, etc.; flame retardants such as halogen compounds, phosphate ester compounds, phosphate amide compounds, fluororesins or metal oxides, (poly)melamine phosphate, and (poly)piperazine phosphate; lubricants of hydrocarbon, fatty acid, aliphatic alcohol, aliphatic ester, aliphatic amide, or metal soap types; colorants such as dyes, pigments, and carbon black; crystallizing agents such as nucleating agents and crystallization accelerators; rubber elasticity imparting agents such as silane coupling agents and flexible polymers; and sensitizers. Other components mentioned above may include organic polymers as resin components other than the curable components described above. Such organic polymers may include those listed as organic polymers in International Publication No. 2014 / 021023.

[0180] The total content of other components in the composition of this disclosure may be 30 parts by mass or less per 100 parts by mass of the composition.

[0181] 8. Other The method for producing the above composition is any method that allows the above components to be blended in the desired amounts, and may be a method in which the above components are added and mixed simultaneously, or a method in which the components are added sequentially and mixed.

[0182] The above composition is preferably used in applications where curability and heat resistance of the cured product are required, such as thermosetting paints, photocurable paints or varnishes, thermosetting adhesives, photocurable adhesives, printed circuit boards, or color filters in liquid crystal display panels for color displays such as color televisions, PC monitors, personal digital assistants, and digital cameras, color filters for CCD image sensors, photospacers, black column spacers, electrode materials for plasma display panels, touch panels, touch sensors, powder coatings, printing inks, printing plates, adhesives, dental compositions, resins for stereolithography, gel coats, photoresists for electronics, electroplating resists, etching resists, both liquid and dry films, solder resists, and for manufacturing color filters for various display applications, or for manufacturing plasma display panels, electroluminescent display devices, and LCDs. It can be used in a variety of applications, including resists for forming structures in manufacturing processes, compositions for encapsulating electrical and electronic components, solder resists, magnetic recording materials, micro-mechanical components, waveguides, optical switches, plating masks, etching masks, color test systems, glass fiber cable coatings, stencils for screen printing, materials for manufacturing three-dimensional objects by stereolithography, holographic recording materials, image recording materials, micro-electronic circuits, decolorizing materials, decolorizing materials for image recording materials, decolorizing materials for image recording materials using microcapsules, photoresist materials for printed circuit boards, photoresist materials for UV and visible laser direct imaging systems, photoresist materials used for dielectric layer formation in sequential lamination of printed circuit boards, photoresist materials or protective films for 3D mounting, and there are no particular limitations on its use. In this disclosure, the material is particularly suitable for use in color filters, photospacers, black column spacers, electrode materials, photoresists, solder resists, overcoats, insulating films, black matrices, partition materials, and the like. This is because it can more effectively demonstrate the effect of having an excellent balance between curability and the heat resistance of the cured product. Furthermore, these components can be preferably used for forming parts in electronic equipment used in transportation equipment such as automobiles and aircraft, where long-term heat resistance is required. This is because they can more effectively demonstrate the excellent balance between curability and the heat resistance of the cured product.

[0183] B. Cured product Next, the cured product of this disclosure will be described. The cured product of this disclosure is formed by curing the above-described composition.

[0184] According to this disclosure, because the above-described composition is used, the product has excellent heat resistance.

[0185] The cured product of this disclosure uses the above-described composition. The above cured product includes a high molecular weight material formed by the curable component contained in the above composition. The contents of such compositions can be the same as those described in section "A. Composition" above, so a detailed explanation is omitted here.

[0186] Compound A contained in the above cured product has a phenolic hydroxyl group protected by group R 101 Even if protected by the protective group R 101 It may also be a case where a phenolic hydroxyl group has been generated by the elimination of a phenolic hydroxyl group. In this disclosure, from the viewpoint of making the cured product have excellent heat resistance, compound A has a protecting group R 101 It is preferable that a phenolic hydroxyl group is generated by the elimination of a phenolic hydroxyl group.

[0187] The planar shape of the cured product can be appropriately set according to the intended use of the product, for example, it can be a pattern such as a dot pattern or a line pattern.

[0188] The uses of the above-mentioned cured product may be the same as those described in section "A. Composition" above.

[0189] The method for producing the cured product is not particularly limited as long as it is a method that can form a high molecular weight product using the curable component in the composition. As an example of such a manufacturing method, the manufacturing method described in section C. Method for manufacturing cured products, which will be discussed later, can be used.

[0190] C. Method for manufacturing cured products Next, a method for producing the cured product of this disclosure will be described. The method for producing the cured product of this disclosure is characterized in that it includes a curing step for curing the above-described composition.

[0191] According to this disclosure, since the above-described composition is used, a cured product with excellent heat resistance can be easily obtained.

[0192] 1.Curing process The curing step in this disclosure is a step of curing the above-mentioned composition. As a method for curing the above composition, a method of forming a high molecular weight material with a curable component can be used.

[0193] As a curing method in this process, for example, one method is to use a curing catalyst together with a curable component in the above composition. In the curing method described above, if the curing catalyst includes a photopolymerization initiator such as a photoradical polymerization initiator or a photocationic polymerization initiator, it is preferable to use a method in which the curable components are cured by irradiating the composition with light. This is because the curing of the composition is facilitated by this curing method. The light irradiated onto the composition preferably includes light with a wavelength of 300 nm to 450 nm. This is because using light of the above wavelength facilitates the curing of the composition. As the light source for the above-mentioned light irradiation, for example, light-emitting diodes (LEDs), ultra-high pressure mercury, mercury vapor arcs, carbon arcs, xenon arcs, etc., can be preferably used. This is because using the above light source facilitates the curing of the composition. The light used for irradiation may be laser light. The laser light may include light with a wavelength of 340-430 nm. As a light source for laser light, those that emit light in the visible to infrared region, such as argon ion lasers, helium-neon lasers, YAG lasers, and semiconductor lasers, can also be used. Furthermore, when using these lasers, the above composition may include a sensitizing dye that absorbs the visible to infrared region.

[0194] In the curing method described above, when the curing catalyst includes a thermal polymerization initiator such as a thermal radical polymerization initiator or a thermal cationic polymerization initiator, when the curing catalyst includes a thermosetting agent, or when the curable component includes a thermosetting compound, it is preferable to perform a heat treatment on the composition to cure the curable components together. This is because the heat treatment facilitates the curing of the composition. The heating temperature should be such that the above composition can be stably cured, preferably 60°C or higher, and more preferably 100°C to 300°C. This is because the curing of the composition is facilitated at this heating temperature. The heating time can range from 10 seconds to approximately 3 hours. This is because the composition hardens easily within these heating times.

[0195] The curing method described above may consist solely of curing the curable component by light irradiation, solely of curing the curable component by heating, or a combination of both. When using both methods, for example, light irradiation and heating may be performed simultaneously, or sequentially.

[0196] 2. Desorption process The manufacturing method of this disclosure has the above-described curing step, but from the viewpoint of obtaining a cured product with excellent heat resistance, the protecting group R is removed from compound A. 101 It is preferable to have a desorption step for detaching the component.

[0197] Protective base R in this process 101 Methods for removing the compound include, for example, heat treatment of compound A, and light irradiation treatment of compound A. In this process, the above-mentioned protective group R 101 However, if the methylene group at the oxygen atom end of an unsubstituted or substituted aliphatic hydrocarbon group, an unsubstituted or substituted aromatic hydrocarbon-containing group, an unsubstituted or substituted heterocyclic-containing group, or an unsubstituted or substituted silyl group is a group having 1 to 40 carbon atoms in which the methylene group is replaced with a divalent group selected from group I, the removal method is preferably a method of heat treatment of compound A. Protecting group R 101 Because it is easy to detach. In this process, the above-mentioned protective group R 101 However, in the case of a photo-leaving protecting group such as an o-nitrobenzyl group, the method of removal is preferably a photo-irradiation method. The above protecting group R 101 Because it is easy to detach.

[0198] A method for heat-treating compound A is, for example, removing the protecting group R from compound A contained in the composition or its cured product. 101 Any method that can remove the compound is acceptable. For example, one method is to heat the composition or its cured product on a hot plate, in an oven, etc. The heating temperature for compound A above is for the protecting group R 101 The heating temperature can be set to a temperature above the temperature at which the protecting group R is removed. Specifically, the heating temperature is preferably 80°C to 300°C, preferably 100°C to 290°C, more preferably 120°C to 280°C, particularly preferably 150°C to 250°C, and most preferably 180°C to 240°C. With the above heating temperature, the protecting group R is removed from compound A. 101 Because it is easy to detach. Furthermore, the above heating temperature is determined when the above composition contains an acid catalyst, a base catalyst, etc., by protecting group R 101The desorption temperature can be kept below the desorption temperature observed when the substance is used alone. The above heating temperature may be the same as that described in section "1. Compound A" of "A. Composition" above. The heating time can be between 5 minutes and 3 hours.

[0199] As a method for treating compound A with light, for example, a method of irradiating the composition or its cured product with light can be used. The wavelength of light irradiated onto the composition or cured product may be the same as that described in section "1. Compound A" of "A. Composition" above. As the light source for the above-mentioned light irradiation, the light source described in "1. Curing Process" above can be used. The integrated light amount for compound A is the protecting group R 101 The integrated light intensity can be set to a level above the amount at which desorption occurs. The above integrated light intensity (integrated light intensity at wavelengths of 300 nm to 430 nm) is 1,000 mJ / cm². 2 More than 10,000mJ / cm 2 Preferably, the following, and in particular, 1,000 mJ / cm² 2 Super 5,000mJ / cm 2 Preferably, the following, and especially 2,000 mJ / cm² 2 More than 4,000mJ / cm 2 The following is more preferable: With the above integrated light intensity, the protecting group R from compound A 101 Because it is easy to detach. The above-mentioned cumulative light quantity can be, for example, the same as that described in section "1. Compound A" of "A. Composition" above.

[0200] The timing of this process can be any time that it allows for the acquisition of a cured product with the desired heat resistance. For example, if the above implementation timing is a process in which the main process is irradiated with light, and the curing method in the above curing process is a method in which the composition is irradiated with light and the curable components are cured together, then the above implementation timing may be performed simultaneously with the above curing process. Furthermore, regarding the timing of the above implementation, if this process involves heat treatment and the curing method in the above curing process involves irradiating the composition with light to cure the curable components together, it is preferable that the above implementation takes place after the light irradiation treatment that cures the curable components together. This is because it results in excellent process passability. If this step is a heat treatment step, and the curing method in the curing step is a method of curing the curable components by applying heat treatment to the composition, the timing of this step may be performed simultaneously with the heat treatment for curing the curable components in the curing step or the post-bake step described later.

[0201] 3. Other processes The above method for producing the cured product may include, as necessary, other steps in addition to the curing step and the desorption step. Other steps mentioned above include a developing step to remove uncured portions from the coating film of the composition after the curing step to obtain a patterned cured product, a post-bake step to heat-treat the cured product after the curing step, a pre-bake step to heat-treat the composition before the curing step to remove solvents from the composition, and a step to form a coating film of the composition before the curing step.

[0202] One method for removing the uncured portion in the above development process is to apply an alkaline developer to the uncured portion. As the alkaline developer mentioned above, commonly used alkaline developers such as tetramethylammonium hydroxide (TMAH) aqueous solution, potassium hydroxide aqueous solution, or sodium hydroxide aqueous solution can be used. The development process described above can be performed after the curing process described above. The heating conditions in the post-bake process described above can be any conditions that improve the strength of the hardened product obtained in the curing process, for example, they can be 100°C to 200°C for 20 to 90 minutes. The heating conditions in the pre-baking process described above can be any conditions necessary to remove the solvent from the composition, for example, 70°C to 150°C for 10 to 60 minutes. In the process of forming the above-mentioned coating film, known methods such as spin coaters, roll coaters, bar coaters, die coaters, curtain coaters, various printing methods, and dipping can be used to apply the composition. The above coating can be formed on a substrate. The above-mentioned substrate can be appropriately set according to the intended use of the cured product, and examples include soda glass, quartz glass, semiconductor substrates, metals, paper, plastics, and the like. Furthermore, the cured product may be used either after being formed on the substrate and then peeled off from the substrate, or transferred from the substrate to another adherend.

[0203] 3. Others The cured product produced by the above manufacturing method and its uses may be the same as those described in section "A. Composition" above.

[0204] D. Additives Next, the additives of this disclosure will be described. The additives of this disclosure include a compound represented by the above general formula (A1) and a metal deactivator.

[0205] According to this disclosure, since the compound represented by the above general formula (A1) and a metal deactivator are included, by adding them to a composition containing a curable component, it becomes possible to easily form a composition with an excellent balance between curability and the heat resistance of the cured product.

[0206] The additive of this disclosure comprises compound A and a metal deactivator.

[0207] 1. Compound A and metal deactivator The total content of compound A and the metal deactivator in the additive of this disclosure may be 100 parts by mass per 100 parts by mass of the solid content of the additive, that is, the solid content of the additive may consist only of compound A and the metal deactivator. Furthermore, the total content of compound A and the metal deactivator may be less than 100 parts by mass per 100 parts by mass of solid content of the additive, meaning that the additive may be a composition containing other components besides compound A and the metal deactivator, for example, more than 20 parts by mass and 99.99 parts by mass or less. This is because having the above content within the above range makes it easier to form compositions with even better curability and heat resistance of the cured product. In this disclosure, from the viewpoint of facilitating the formation of compositions with even better curability and heat resistance of the cured product, the lower limit of the total content of compound A and the metal deactivator is preferably 50 parts by mass or more per 100 parts by mass of the solid content of the additive, more preferably 70 parts by mass or more, and particularly preferably 90 parts by mass or more. This is because having the above content within the above range makes it easy to form compositions with an excellent balance between curability and heat resistance of the cured product. Furthermore, from the viewpoint of facilitating particle size control of the additive, the upper limit of the total content of compound A and the metal deactivator is preferably 99 parts by mass or less per 100 parts by mass of the solid content of the additive, more preferably 95 parts by mass or less, and particularly preferably 90 parts by mass or less. This is because having the above content within the above range makes it easy to form compositions with an excellent balance between curability and heat resistance of the cured product.

[0208] Furthermore, the same provisions as those described in sections "1. Compound A" and "2. Metal Deactivator" of "A. Composition" above may be used for Compound A and the metal deactivator. The content of compound A in the total of 100 parts by mass of compound A and the metal deactivator may be the same as that described in section "A. Composition" above.

[0209] 2. Solvent The above additive may contain a solvent in addition to compound A and the metal deactivator. The solvent mentioned above can be any solvent capable of dispersing or dissolving each component in the additive, and can be the same as described in section "A. Composition" above. Furthermore, the content of the additive can be between 1 and 99 parts by mass per 100 parts by mass of the above-mentioned additive.

[0210] 3. Other ingredients The above-mentioned additive may also contain other components besides compound A, the metal deactivator, and the solvent. Other ingredients mentioned above include those listed in section 5, "Other Ingredients," of section A, "Composition," above. The content of the above-mentioned other components can be appropriately set depending on the application of the additive, but for example, it can be 50 parts by mass or less per 100 parts by mass of the additive, and preferably 10 parts by mass or less. This is because the above-mentioned additive makes it easy to increase the content ratio of compound A and the metal deactivator, and makes it easier to form a composition with even better curability and heat resistance of the cured product.

[0211] 4. Others The properties of the above-mentioned additive can be appropriately determined depending on the method of addition to the composition, etc. For example, it can be in the form of a liquid, powder, pellet, etc., in which compound A and a metal deactivator, etc. are dispersed or dissolved in a solvent. The method for producing the above additive can be any method that allows compound A and a metal deactivator to be included in the desired proportions.

[0212] Applications of the above-mentioned additives include their addition to compositions requiring heat resistance, and it is preferable that they be added to compositions containing curable components, and in particular, it is preferable that the curable component contains a radical polymerizable compound. The uses of the above composition can be, specifically, the same as those described in section "A. Composition" above.

[0213] This disclosure is not limited to the embodiments described above. The embodiments described above are illustrative, and any configuration that is substantially identical to the technical idea described in the claims of this disclosure and achieves similar effects is included within the technical scope of this disclosure. [Examples]

[0214] The present disclosure will be described in more detail below with reference to examples, but the present disclosure is not limited to these examples.

[0215] [Manufacturing Example A1-1] 0.01 mol of a phenol compound (represented by formula (C1-1) below), 0.05 mol of di-tert-butyl dicarbonate, and 30 g of pyridine were mixed. Under a nitrogen atmosphere, at room temperature, 0.025 mol of 4-dimethylaminopyridine was added, and the mixture was stirred at 60°C for 3 hours to obtain the reaction solution. After cooling to room temperature, the reaction solution was poured into 150 g of deionized water, and 200 g of chloroform was added to separate the oil and water. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and 100 g of methanol was added to the residue to perform crystallization. The obtained white powdery crystals were dried under reduced pressure at 60°C for 3 hours to obtain the target product (represented by general formula (A1-1) below). The fact that the obtained white powdery crystals are the target product was confirmed. 1 Confirmed by 1H-NMR.

[0216] [Manufacturing Examples A1-2 and A1-3] The compounds represented by formulas (A1-2) to (A1-3) below were synthesized in the same manner as in Production Example A1-1, except that formulas (C1-2) to (C1-3) below were used as phenol compounds. The obtained white powdery crystals were the target product. 1 Confirmed by 1H-NMR.

[0217] [ka]

[0218] [ka]

[0219] [Examples 1-10 and Comparative Examples 1-8] According to the formulations described in Tables 1 to 4 below, compound A, a metal deactivator, an antioxidant, a curing component, a curing catalyst, a filler, and a solvent were stirred in a defoaming stirrer at an initial temperature of 25°C for 3 minutes to obtain the composition. Furthermore, the following materials were used for each component. Note that the amounts listed in the table represent the mass parts of each component.

[0220] (Compound A) A-1: Compound represented by the above formula (A1-1), manufactured in manufacturing example A1-1. A-2: Compound represented by formula (A1-2) above, manufactured in manufacturing example A1-2. A-3: Compound represented by formula (A1-3) above, manufactured in manufacturing example A1-3.

[0221] (metal deactivator) B-1: Compound represented by the following formula (B-1) (benzotriazole compound) B-2: Compound represented by the following formula (B-2) (benzotriazole compound) B-3: Compound represented by the following formula (B-3) (hydrazide compound) B-4: VD-5 (triazine compound) manufactured by Shikoku Chemicals, Inc. B-5: X12-1214A (benzotriazole compound) manufactured by Shin-Etsu Silicone Co., Ltd.

[0222] [ka]

[0223] (Antioxidant) C-1: Compound represented by the above formula (C1-1) C-2: Compound represented by the above formula (C1-2) C-3: Compound represented by the above formula (C1-3)

[0224] (Curing component: Polymerizable compound (radical polymerizable compound)) D1-1: Carboxyl group-containing epoxy acrylate resin (radical polymerizable compound, carboxyl group-containing resin, acid value of solids 100 mg KOH / g, solids concentration 67.2% by mass, CCR-1711H manufactured by Nippon Kayaku Co., Ltd., epoxy acrylate obtained by reacting acrylic acid with a carboxyl group-containing cresol novolac type epoxy resin) D1-2: Compound represented by the following formula (D1-2) (radical polymerizable compound, compound without a carboxyl group, DPHA, manufactured by Nippon Kayaku Co., Ltd.)

[0225] (Curing component: Thermosetting compound (epoxy compound)) D2-1: Compound represented by the following formula (D2-1) (thermosetting compound, EPPN-201 manufactured by Nippon Kayaku Co., Ltd., novolac-type epoxy resin) D2-2: ADEKA EP-4100 (Bisphenol A type epoxy resin, epoxy equivalent 190)

[0226] [ka] [ka]

[0227] (Curing catalyst: radical polymerization initiator) E-1: Irgacure 184 (a compound represented by the following formula (E-1), a radical polymerization initiator, manufactured by BASF, an acetophenone compound) E-2: Irgacure 907 (a compound represented by the following formula (E-2), a radical polymerization initiator, manufactured by BASF, an acetophenone compound) E-3: Irgacure TPO (a compound represented by the following formula (E-3), a radical polymerization initiator, manufactured by BASF, an acylphosphine oxide compound) E-4: Irgacure OXE02 (a compound represented by the following formula (E-4), a radical polymerization initiator, manufactured by BASF, an oxime ester compound)

[0228] [ka]

[0229] (Curing catalyst: thermosetting agent) F-1: Melamine derivative (Nicalac MW-390, manufactured by Sanwa Chemical, alkoxyalkylated melamine compound) F-2: Dicyandiamide (DICY)

[0230] (Filler) G-1: Titanium dioxide (TIPAQUE CR-80 manufactured by Ishihara Sangyo Co., Ltd., titanium dioxide particles surface-treated with Al and Si, average particle size (D50) of 0.25 μm) G-2: Silica (SO-E5 manufactured by Admatex, silicon dioxide particles, average particle size (D50) of 1.3~1.7 μm)

[0231] (solvent) H-1: Propylene glycol monomethyl ether acetate (PGMEA)

[0232] [evaluation] The heat resistance and curability of the obtained examples and comparative compositions were evaluated by the following method.

[0233] 1. Heat resistance evaluation (1) Preparation of evaluation samples Each composition obtained in the examples and comparative examples was applied to a 1.6 mm thick FR-4 copper-clad laminate so that the cured film thickness was 20 μm, and then dried at 80°C for 30 minutes. Next, using a high-pressure mercury lamp, 500 mJ / cm² was measured. 2 Ultraviolet exposure was performed using the integrated light intensity (integrated light intensity of light with wavelengths of 320nm to 400nm). Next, the samples were heated at 150°C for 60 minutes to obtain evaluation samples.

[0234] (2) Heat resistance evaluation The evaluation sample was subjected to 1,000 mJ / cm³. 2After additional UV exposure with the integrated light intensity (integrated light intensity of wavelengths 320nm to 400nm), the samples were subjected to a heat treatment (heat test) in a 200°C oven for 90 minutes. The b* values ​​before and after heating were determined using a colorimeter. The change in b* values ​​(Δb*) before and after the heat test was evaluated according to the following criteria. ++:Δb* is less than 5 +:Δb* is 5 or greater and less than 10 -:Δb* is 10 or greater Furthermore, a smaller Δb* indicates superior heat resistance.

[0235] 2. Curing performance evaluation (1) Preparation of evaluation samples The compositions of the examples and comparative examples were applied to a glass substrate to a cured film thickness of 20 μm, and then dried at 80°C for 30 minutes. Subsequently, exposure was performed using a high-pressure mercury lamp through a photomask (mask aperture 30 μm) (exposure gap 300 μm, exposure dose 500 mJ / cm²). 2 (Integrated light intensity of light with wavelengths of 320nm to 400nm). After developing with a 1.0% by mass aqueous sodium carbonate solution for 60 seconds, the samples were thoroughly washed with water, and post-baked in a clean oven at 150°C for 60 minutes to fix the patterns and obtain evaluation samples.

[0236] (2) Evaluation of hardening properties The patterns of the obtained evaluation samples were observed with an optical microscope, and the line width of the portion corresponding to the mask opening was measured. +: The resulting line width is 30 μm or greater. -: The resulting line width is less than 30 μm. Furthermore, the wider the pattern width of the cured material is compared to the set line width, the better the curing performance can be judged to be.

[0237] [Table 1]

[0238] [Table 2]

[0239] [Table 3]

[0240] [Table 4]

[0241] The results shown in Tables 1-4 confirm that the compositions of the examples exhibit excellent curability and heat resistance. As shown in Comparative Examples 4-6, when an antioxidant having a phenolic hydroxyl group other than compound A is used, the curability is inferior even when a metal deactivator is included. Furthermore, a comparison between Comparative Example 4 and Comparative Example 8 shows that when an antioxidant other than compound A is included, the heat resistance improvement effect due to the inclusion of a metal deactivator is not obtained. On the other hand, as can be seen from a comparison between Comparative Example 2 and Example 1, in the present invention, curability is obtained and a significant heat resistance improvement effect can be obtained by having a metal deactivator in the presence of the compound of formula (A1). A comparison of Comparative Examples 1, 2, 7 and Example 2 also shows that in the present invention, the heat resistance is synergistically improved by using the compound of formula (A1) and a metal deactivator in combination. [Industrial applicability]

[0242] This disclosure offers the advantage of providing a composition with an excellent balance between curability and the heat resistance of the cured product.

Claims

1. A compound represented by the following general formula (A1), Metal deactivators and A hardening component, Radical polymerization initiator and Thermosetting agent and Inorganic fillers and, Includes, The metal deactivator comprises at least one of a benzotriazole compound, a hydrazide compound, a salicylic acid compound, and a triazine compound represented by the following general formula (B1). The hydrazide compound is a compound represented by the following general formula (B2), The salicylic acid compound is a compound represented by the following general formula (B3-1) or (B3-2), The aforementioned triazine compound is a compound represented by the following general formula (B4), The curing component includes a radical polymerizable compound and a thermosetting compound. Radical polymerizable compounds include compounds having a carboxyl group and an ethylenically unsaturated group, and compounds not having a carboxyl group. The thermosetting compound is one or more selected from cyclic ether compounds and cyclic thioether compounds. The aforementioned thermosetting agent comprises one or more selected from melamine derivatives, dicyandiamides, hydrazine compounds, S-triazine derivatives, polymercaptans, acid anhydrides, and phenolic resins, and contributes to the formation of high molecular weight thermosetting compounds. composition. 【Chemistry 1】 (In the formula, R １０１ This represents a group with 1 to 40 carbon atoms in which the methylene group at the oxygen atom end of an unsubstituted or substituted aliphatic hydrocarbon group is substituted with -CO-O-. R １０２ and R １０３ Each of these independently represents an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted. R １０４ This represents a halogen atom, cyano group, hydroxyl group, nitro group, carboxyl group, methyl group, ethyl group, propyl group, and isopropyl group. n represents an integer between 2 and 4. a1 represents an integer of 0 or 1, There are multiple R １０１ , R １０２ , R １０３ , R １０４ And a1 may be the same or they may be different. X represents an aliphatic hydrocarbon group having 10 to 40 carbon atoms, either unsubstituted or substituted, with the same valency as n; an aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, either unsubstituted or substituted, with the same valency as n; a heterocyclic-containing group having 4 to 40 carbon atoms, either unsubstituted or substituted, with the same valency as n; or a group having 4 to 40 carbon atoms in which one or more methylene groups in an aliphatic hydrocarbon group, aromatic hydrocarbon-containing group, or heterocyclic-containing group having the same valency as n, are replaced by a divalent group selected from group I below. Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO ２ -, -NR ２３０ -, -NR ２３０ -CO-, -CO-NR ２３０ -, -NR ２３０ -COO-, -OCO-NR ２３０ - or -SiR ２３０ R ２３１ -. However, R ２３０ and R ２３１ each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group. (1) When n is 2, X in general formula (A1) is a substituent represented by the following general formula (101) or a group selected from group 1 below; (2) When n is 3, X in general formula (A1) is a group selected from group 2 below; (3) When n is 4, X in general formula (A1) is a group selected from group 3 below. 【Chemistry 2】 (In the formula, Y 111 and Y 115 each independently represent a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms that is either unsubstituted or substituted, or a group having 1 to 8 carbon atoms in which one or more methylene groups in the unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from the above group I.) Y 112 and Y 114 each independently represent a group represented by -O-, -CO-, -CO-O-, -O-CO-, -NR 213-, -CO-NR 213-, or -NR 213-CO-, R 213 represents a group having 1 to 40 carbon atoms in which one or more of the hydrogen atoms, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, or a methylene group in an unsubstituted or substituted aliphatic hydrocarbon group is replaced by a divalent group selected from the above group I. Y 113 represents -CR 214 R 215-, -NR 216-, a group represented by the following general formula (103), a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms and being unsubstituted or substituted, a divalent aromatic hydrocarbon-containing group having 6 to 40 carbon atoms and being unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from the above group I, or a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from the above group I. R214 and R215 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms. R 216 represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from Group I, or a group having 2 to 40 carbon atoms in an unsubstituted or substituted heterocyclic-containing group in which one or more methylene groups are replaced by a divalent group selected from Group I. * indicates a connection point. 【Transformation 3】 (In the formula, Y 119 and Y 120 each independently represent a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms that is either unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in the unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from the above group I.) * indicates a connection point. 【Chemistry 4】 (In the formula, R 31 represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, or an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from the above group I, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from the above group I, or a group having 2 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted heterocyclic-containing group are replaced by a divalent group selected from the above group I.) * indicates a connection point. 【Transformation 5】 (In the formula, R 32 represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from the above group I, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from the above group I, or a group having 2 to 40 carbon atoms in an unsubstituted or substituted heterocyclic-containing group in which one or more methylene groups are replaced by a divalent group selected from the above group I, and if there are two or more R 32 in the group, the two or more R 32 may be the same or different.) Z 11 is independently -O-, -S-, >CO, -CO-O-, -O-CO-, -SO 2-, -SS-, -SO-, >NR 63, -PR 63 - represents a divalent aliphatic hydrocarbon group having 1 to 40 carbon atoms that is unsubstituted or substituted, a divalent aromatic hydrocarbon-containing group having 6 to 40 carbon atoms that is unsubstituted or substituted, a divalent heterocyclic-containing group having 2 to 40 carbon atoms that is unsubstituted or substituted, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I above, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from Group I above, or a group having 2 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted heterocyclic-containing group are replaced by a divalent group selected from Group I above. R 63 represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, or an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aliphatic hydrocarbon group are replaced by a divalent group selected from Group I, a group having 6 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted aromatic hydrocarbon-containing group are replaced by a divalent group selected from Group I, or a group having 2 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted heterocyclic-containing group are replaced by a divalent group selected from Group I. * indicates a connection point. 【Transformation 6】 (In the formula, R 32 represents the same group as R 32 in group 2 above, and if there are two or more R 32s in the group, the two or more R 32s may be the same or different.) Z 11 represents the same range of groups as the group represented by Z 11 in group 2 above. * indicates a connection point. 【Transformation 7】 (In the formula, R1 represents a hydrogen atom, a hydroxyl group, an unsubstituted or silyl hydrocarbon group having 1 to 20 carbon atoms, or a silyl group having 0 to 20 carbon atoms.) R2 represents a hydrocarbon group having 1 to 20 carbon atoms, either unsubstituted or substituted. nb1 represents an integer between 0 and 4. 【Transformation 8】 (In the formula, R3, R4, R5, and R6 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted.) R7 and R8 each independently represent unsubstituted or substituted hydrocarbon groups having 1 to 40 carbon atoms. R9 and R10 are, independently, a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon-containing group having 6 to 40 carbon atoms, an unsubstituted or substituted heterocyclic-containing group having 2 to 40 carbon atoms, an unsubstituted or substituted silyl group having 0 to 40 carbon atoms, or a group having 1 to 40 carbon atoms in an unsubstituted or substituted aliphatic hydrocarbon group where one or more methylene groups are replaced by a divalent group selected from the following group I-B2, or an unsubstituted group. Alternatively, it represents a group having 6 to 40 carbon atoms in which one or more methylene groups in a substituted aromatic hydrocarbon-containing group are replaced with a divalent group selected from groups I-B2 below; a group having 2 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted heterocyclic-containing group are replaced with a divalent group selected from groups I-B2 below; or a group having 0 to 40 carbon atoms in which one or more methylene groups in an unsubstituted or substituted silyl group are replaced with a divalent group selected from groups I-B2 below. Group I-B2: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR230-B2-, -NR230-B2-CO-, -CO-NR230-B2-, -NR230-COO-, -OCO-NR230-B2-, or -SiR230-B2R231-B2-. R230-B2 and R231-B2 each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 40 carbon atoms. 【Chemistry 9】 (In the formula, R 11 represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 40 carbon atoms, either unsubstituted or substituted.) 【Chemistry 10】 (In the formula, R 12 represents an unsubstituted or substituted hydrocarbon group having 1 to 40 carbon atoms.) 【Chemistry 11】 (In the formula, R 14 represents a single bond or a linking group.) The linking group is an aliphatic hydrocarbon group, carbonyl group, ether bond, ester bond, carbonate group, amide group, thioether group, amino group, or a group formed by linking multiple such groups, all having 1 to 40 divalent carbon atoms and being either unsubstituted or substituted. R 13-1, R 13-2, R 13-3, and R 13-4 each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. R 15-1 and R 15-2 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, or a methoxy group. R 16 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a methoxy group, or a group represented as -SiR 17 s (OR 18) 3-s. R17 and R18 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. nb4 represents an integer between 0 and 16. s represents an integer between 0 and 3.

2. The composition according to claim 1, wherein the content of the metal deactivator is 5 parts by mass or more and 90 parts by mass or less in a total of 100 parts by mass of the compound represented by the general formula (A1) and the metal deactivator.

3. The composition according to claim 1 or 2, wherein the total content of the compound represented by the general formula (A1) and the metal deactivator is 0.01 parts by mass or more and 10 parts by mass or less in 100 parts by mass of the total of the compound represented by the general formula (A1), the metal deactivator and the curable component.

4. A composition according to any one of claims 1 to 3, for use as solder resist.

5. A cured product of the composition according to any one of claims 1 to 4.

6. A method for producing a cured product, comprising a curing step for curing the composition according to any one of claims 1 to 4.

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