Radical polymerization initiator, composition, cured product, and method for producing the cured product

Abstract

A purpose of the present invention is to provide a radical polymerization initiator that has excellently stable sensitivity.　The present invention is a radical polymerization initiator including a compound represented by the following general formula (A), and an acid component, wherein the acid component content is 1 ppm to 400 ppm in relation to the total of the compound represented by general formula (A) and the acid component. (A represents a C6-20 aromatic ring group, R31 represents an oxime ester group, R32 represents a radical-generating group other than an oxime ester group, R33 represents a C1-20 unsubstituted or substituted aliphatic hydrocarbon group or a C6-20 unsubstituted or substituted aromatic hydrocarbon ring-including group, a represents an integer 1-20, b represents an integer 0-20, and c represents an integer 0-20.)

Description

[Technical Field]

[0001] The present invention relates to a radical polymerization initiator having excellent sensitivity and storage stability. [Background technology]

[0002] Known photosensitive compositions include photocurable compositions prepared by adding a photopolymerization initiator to a polymerizable compound having an ethylenically unsaturated bond. Such photocurable compositions can be cured by irradiation with energy rays (light), and are therefore used in photocurable inks, photosensitive printing plates, various photoresists, and the like.

[0003] As the photopolymerization initiator used in the photosensitive composition, the following Patent Documents 1 to 7 propose the use of an oxime ester compound. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] US Patent Application Publication No. 2004 / 170924 [Patent Document 2] US Patent Application Publication No. 2007 / 270522 [Patent Document 3] US Patent Application Publication No. 2009 / 292039 [Patent Document 4] US Patent Application Publication No. 2011 / 129778 [Patent Document 5] EP2407456A1 [Patent Document 6] EP2433927A1 [Patent Document 7] Special Publication No. 2013-543875 Summary of the Invention

[0005] However, when the oxime ester compounds described in Patent Documents 1 to 7 are used as radical polymerization initiators, there is a problem that the sensitivity may be unstable.

[0006] The present invention has been made in view of the above problems, and has as its main object to provide a radical polymerization initiator having excellent stability of sensitivity.

[0007] As a result of intensive investigations to solve the above problems, the present inventors have found that a radical polymerization initiator containing an oxime ester compound and a predetermined amount of an acid component has excellent stability of sensitivity, and have thus completed the present invention.

[0008] That is, the present invention provides a radical polymerization initiator comprising a compound represented by the following general formula (A) and an acid component, wherein the content of the acid component is 1 ppm or more and 400 ppm or less in the total of the compound represented by the general formula (A) and the acid component:

[0009] [ka] (In the formula, A represents an aromatic ring group having 6 to 20 carbon atoms, R 31 represents a group represented by the following general formula (1): R 32 represents a radical-generating group other than that represented by the general formula (1), an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom is substituted with a radical-generating group other than that represented by the general formula (1), an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms in which a hydrogen atom is substituted with a radical-generating group other than that represented by the general formula (1), an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms in which a hydrogen atom is substituted with a radical-generating group other than that represented by the general formula (1), or a group in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon ring-containing group or heterocycle-containing group are substituted with a divalent group selected from the following group I: R 33represents a halogen atom, a nitro group, a cyano group, -OR 34 , -COR 34 , -OCOR 34 , -COOR 34 , -SR 34 , -SOR 34 , -SO2R 34 , -NR 35 R 36 , -NR 35 COR 36 , -CONR 35 R 36 an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group or the above heterocycle-containing group are replaced by a divalent group selected from the following Group I: R 34 , R 35 and R 36 each independently represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon ring-containing group, or heterocyclic ring-containing group have been replaced with a divalent group selected from the following Group I; R 34 , R 35 or R 36 When there are multiple, they may be the same or different, the substituent substituting one or more hydrogen atoms in the aliphatic hydrocarbon group having the above-mentioned substituent, the aromatic hydrocarbon ring-containing group having the above-mentioned substituent, and the heterocycle-containing group having the above-mentioned substituent is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, or -COOH; a represents an integer from 1 to 20; b represents an integer of 0 to 20; c represents an integer from 0 to 20; The sum of a, b and c is 20 or less.)

[0010] [ka] (In the formula, R 1 represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group, or the above heterocycle-containing group are substituted with a divalent group selected from the following Group I: R 2 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group, or the above heterocyclic ring-containing group are replaced with a divalent group selected from the following Group I: the substituent substituting one or more hydrogen atoms in the aliphatic hydrocarbon group having the above-mentioned substituent, the aromatic hydrocarbon ring-containing group having the above-mentioned substituent, and the heterocycle-containing group having the above-mentioned substituent is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, or -COOH; n represents 0 or 1; * indicates the point of attachment.) Group I: -O-, -COO-, -OCO-, -CO-, -CO-CO-, -CO-CO-O-, -CS-, -S-, -SO-, -SO2-, -NR 40 -, -NR 40 -CO-, -CO-NR 40 -, -NR 40 -COO-, -OCO-NR 40 -or-SiR 40 R 41 -. R 40 and R 41each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 40 or R 41 When there are multiple, they may be the same or different.

[0011] The radical polymerization initiator of the present invention has excellent stability of sensitivity by containing the compound having the above structure and a predetermined amount of an acid component.

[0012] In the present invention, the acid component is preferably an organic acid, because this allows the radical polymerization initiator to have better stability in sensitivity.

[0013] In the present invention, the compound represented by the general formula (A) is preferably a compound represented by the following formula (A1), because this provides the radical polymerization initiator with better sensitivity stability.

[0014] [ka] (In the formula, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each independently a hydrogen atom, R in the above general formula (A), 31 and R in the above general formula (A). 32 or a group represented by R in the above general formula (A) 33 is a group represented by R 11 and R 12 , R 12 and R 13 , R 14 and R 15 , R 15 and R 16 or R 16 and R 17 may be bonded to each other to form a ring, R 11 , R 12 , R 13 , R 14 , R15 , R 16 and R 17 At least one of the R 31 is a group represented by

[0015] In the above general formula (A1), R 11 is R in the above general formula (A). 31 This is because the radical polymerization initiator has better stability in sensitivity.

[0016] In the above general formula (A1), R 13 and R 16 is R in the above general formula (A). 33 This is because the radical polymerization initiator has better stability in sensitivity.

[0017] In the above general formula (A1), R 13 is R in the above general formula (A). 33 and R 13 R used in 33 is preferably an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or a group in which one or more methylene groups in the aromatic hydrocarbon ring-containing group have been substituted with a divalent group selected from Group I. This is because the radical polymerization initiator has better stability of sensitivity.

[0018] In the present invention, the content of the compound represented by the general formula (A) is preferably 90 parts by mass or more in 100 parts by mass of the radical polymerization initiator, because this makes the radical polymerization initiator more excellent in sensitivity stability.

[0019] The present invention is a composition containing the above radical polymerization initiator and a radically polymerizable compound. The composition of the present invention contains the radical polymerization initiator, and thus has excellent stability of sensitivity.

[0020] The present invention relates to a cured product of the above composition. The cured product of the present invention uses the above composition, and therefore the durability and other properties of the cured product can be easily adjusted.

[0021] The present invention is a method for producing a cured product, which comprises a polymerization step of polymerizing radically polymerizable compounds in the composition. According to the method for producing a cured product of the present invention, the above composition is used in the polymerization step, so that a cured product having desired durability and the like can be easily obtained. DETAILED DESCRIPTION OF THE INVENTION

[0022] The present invention relates to a radical polymerization initiator, a composition, a cured product, and a method for producing the cured product. The radical polymerization initiator, composition, cured product, and method for producing the cured product of the present invention will be described in detail below.

[0023] A. Radical polymerization initiator First, the radical polymerization initiator of the present invention will be described. The radical polymerization initiator of the present invention is a radical polymerization initiator containing a compound represented by the following general formula (A) (compound A) and an acid component, characterized in that the content of the acid component is 1 ppm or more and 400 ppm or less in the total of the compound represented by the general formula (A) and the acid component:

[0024] [ka] (In the formula, A represents an aromatic ring group having 6 to 20 carbon atoms, R 31 represents a group represented by the following general formula (1): R 32represents a radical-generating group other than that represented by the general formula (1), an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom is substituted with a radical-generating group other than that represented by the general formula (1), an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms in which a hydrogen atom is substituted with a radical-generating group other than that represented by the general formula (1), an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms in which a hydrogen atom is substituted with a radical-generating group other than that represented by the general formula (1), or a group in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon ring-containing group or heterocycle-containing group are substituted with a divalent group selected from the following group I: R 33 represents a halogen atom, a nitro group, a cyano group, -OR 34 , -COR 34 , -OCOR 34 , -COOR 34 , -SR 34 , -SOR 34 , -SO2R 34 , -NR 35 R 36 , -NR 35 COR 36 , -CONR 35 R 36 an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group or the above heterocycle-containing group are replaced by a divalent group selected from the following Group I: R 34 , R 35 and R 36each independently represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon ring-containing group, or heterocyclic ring-containing group have been replaced with a divalent group selected from the following Group I; R 34 , R 35 or R 36 When there are multiple, they may be the same or different, the substituent substituting one or more hydrogen atoms in the aliphatic hydrocarbon group having the above-mentioned substituent, the aromatic hydrocarbon ring-containing group having the above-mentioned substituent, and the heterocycle-containing group having the above-mentioned substituent is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, or -COOH; a represents an integer from 1 to 20; b represents an integer of 0 to 20; c represents an integer from 0 to 20; The sum of a, b and c is 20 or less.)

[0025] [ka] (In the formula, R 1 represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group, or the above heterocycle-containing group are substituted with a divalent group selected from the following Group I: R 2represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group, or the above heterocyclic ring-containing group are replaced with a divalent group selected from the following Group I: the substituent substituting one or more hydrogen atoms in the aliphatic hydrocarbon group having the above-mentioned substituent, the aromatic hydrocarbon ring-containing group having the above-mentioned substituent, and the heterocycle-containing group having the above-mentioned substituent is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, or -COOH; n represents 0 or 1; * indicates the point of attachment.) Group I: -O-, -COO-, -OCO-, -CO-, -CO-CO-, -CO-CO-O-, -CS-, -S-, -SO-, -SO2-, -NR'-, -NR'-CO-, -CO-NR'-, -NR'-COO-, -OCO-NR'- or -SiR'R"-. R' and R" each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and when there are multiple R' or R", they may be the same or different.

[0026] The reason why the radical polymerization initiator of the present invention exhibits the above-mentioned effects by containing a predetermined amount of an acid component together with the compound A is presumed to be as follows.

[0027] The radical polymerization initiator can prevent the group represented by general formula (1) from being decomposed by the acid component during storage by containing a predetermined amount of the acid component used together with compound A. As a result, the radical polymerization initiator can generate a predetermined amount of radicals at a desired timing, and exhibits excellent stability of sensitivity. Furthermore, when the radical polymerization initiator contains a predetermined amount of an acid component together with the compound A, the dissolution rate with each component of the curable composition is improved, making it easier to prepare the curable composition.

[0028] The radical polymerization initiator of the present invention contains compound A and an acid component. Each component of the radical polymerization initiator of the present invention will be described in detail below.

[0029] 1. Compound A The compound A has an oxime ester group, which is a group represented by the general formula (1), and specifically, R 31 is a group represented by the above general formula (1).

[0030] Examples of the halogen atom in the general formula (A) and the general formula (1) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0031] The aliphatic hydrocarbon group having 1 to 20 carbon atoms in the general formula (A) and the general formula (1) is a hydrocarbon group that does not contain an aromatic hydrocarbon ring or a heterocyclic ring, and may have a substituent. The substituted aliphatic hydrocarbon group is a group having a structure in which one or more hydrogen atoms in the aliphatic hydrocarbon group are substituted with a substituent. Examples of unsubstituted aliphatic hydrocarbon groups include alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and cycloalkylalkyl groups having 4 to 20 carbon atoms. Examples of the substituted aliphatic hydrocarbon groups include groups in which one or more hydrogen atoms in the unsubstituted aliphatic hydrocarbon groups have been substituted with a substituent, and examples of the substituent include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, and -COOH.

[0032] The alkyl group having 1 to 20 carbon atoms may be linear or branched. Examples of linear alkyl groups include methyl, ethyl, propyl, butyl, iso-amyl, tert-amyl, hexyl, heptyl, and octyl. 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, iso-octyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, hebrotadecyl, and octadecyl.

[0033] The alkenyl group having 2 to 20 carbon atoms may be linear or branched. It may be a terminal alkenyl group having an unsaturated bond at the terminal, or an internal alkenyl group having an internal unsaturated bond. Examples of terminal alkenyl groups include vinyl, allyl, 2-methyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl. Examples of internal alkenyl groups include 2-butenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3-undecenyl, 4-dodecenyl, and 4,8,12-tetradecatrienyl allyl.

[0034] Examples of the cycloalkyl group having 3 to 20 carbon atoms include saturated monocyclic alkyl groups having 3 to 20 carbon atoms, saturated polycyclic alkyl groups having 3 to 20 carbon atoms, and groups having 4 to 20 carbon atoms in which one or more hydrogen atoms in the ring of these groups have been substituted with an alkyl group. Examples of the saturated monocyclic alkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl. Examples of the saturated polycyclic alkyl group include adamantyl, decahydronaphthyl, octahydropentalene, and bicyclo[1.1.1]pentanyl. Examples of the alkyl group substituting a hydrogen atom in the ring of a saturated monocyclic or saturated polycyclic alkyl group include the groups exemplified above as the alkyl group having 1 to 20 carbon atoms. Examples of the group in which one or more hydrogen atoms in the ring of a saturated polycyclic alkyl group have been substituted with an alkyl group include a bornyl group.

[0035] The cycloalkylalkyl group having 4 to 20 carbon atoms means a group having 4 to 20 carbon atoms in which a hydrogen atom of an alkyl group is substituted with a cycloalkyl group. The cycloalkyl group in the cycloalkylalkyl group may be monocyclic or polycyclic. Examples of cycloalkylalkyl groups having 4 to 20 carbon atoms and a monocyclic cycloalkyl group include cyclopropylmethyl, 2-cyclobutylethyl, 3-cyclopentylpropyl, 4-cyclohexylbutyl, cycloheptylmethyl, cyclooctylmethyl, 2-cyclononylethyl, and 2-cyclodecylethyl. Examples of cycloalkylalkyl groups having 4 to 20 carbon atoms and a polycyclic cycloalkyl group include 3-3-adamantylpropyl and decahydronaphthylpropyl.

[0036] The aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms in the general formula (A) and the general formula (1) is a hydrocarbon group that contains an aromatic hydrocarbon ring but does not contain a heterocycle, and may have an aliphatic hydrocarbon group or may have a substituent. The substituted aromatic hydrocarbon ring-containing group is a group having a structure in which one or more hydrogen atoms in the aromatic hydrocarbon ring-containing group are substituted with a substituent. Examples of the unsubstituted aromatic hydrocarbon ring-containing group include an aryl group having 6 to 20 carbon atoms and an arylalkyl group having 7 to 20 carbon atoms. Examples of the substituted aromatic hydrocarbon ring-containing group include groups in which one or more hydrogen atoms in the unsubstituted aromatic hydrocarbon ring-containing group have been substituted with a substituent, and examples of the substituent include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, and -COOH.

[0037] The aryl group having 6 to 20 carbon atoms may have a monocyclic structure, a fused ring structure, or a structure in which two aromatic hydrocarbon rings are linked together. The aryl group in which two aromatic hydrocarbon rings are linked may be one in which two aromatic hydrocarbon rings of a monocyclic structure are linked, one in which an aromatic hydrocarbon ring of a monocyclic structure and an aromatic hydrocarbon ring of a fused ring structure are linked, or one in which an aromatic hydrocarbon ring of a fused ring structure and an aromatic hydrocarbon ring of a fused ring structure are linked. The linking group connecting two aromatic hydrocarbon rings may be any group that can impart aromaticity to the aryl group as a whole, and examples thereof include a single bond, a sulfide group (-S-), and a carbonyl group. Examples of aryl groups having a monocyclic structure include phenyl, tolyl, xylyl, ethylphenyl, and 2,4,6-trimethylphenyl. Examples of aryl groups having a fused ring structure include naphthyl, anthracenyl, phenanthryl, and pyrenyl. Examples of aryl groups having two monocyclic aromatic hydrocarbon rings linked together include biphenyl, diphenyl sulfide, and benzoylphenyl.

[0038] The arylalkyl group having 7 to 20 carbon atoms means a group in which one or more hydrogen atoms in an alkyl group are substituted with an aryl group. Examples of the arylalkyl group having 7 to 20 carbon atoms include benzyl, fluorenyl, indenyl, 9-fluorenylmethyl, α-methylbenzyl, α,α-dimethylbenzyl, phenylethyl, and naphthylpropyl groups.

[0039] The heterocycle-containing group having 2 to 20 carbon atoms in the general formula (A) and the general formula (1) is a hydrocarbon group containing a heterocycle, and may have an aromatic hydrocarbon ring-containing group or an aliphatic hydrocarbon group, or may have a substituent. The heterocycle-containing group having a substituent is a group having a structure in which one or more hydrogen atoms in the heterocycle-containing group are substituted with a substituent.

[0040] Examples of the unsubstituted heterocycle-containing group include heterocyclic groups such as a pyridyl group, a quinolyl group, a thiazolyl group, a tetrahydrofuran group, a dioxolanyl group, a tetrahydropyranyl group, a morpholylfuran group, a methylthiophene group, a hexylthiophene group, a benzothiophene group, a pyrrole group, a pyrrolidine group, an imidazole group, an imidazolidine group, an imidazoline group, a pyrazole group, a pyrazolidine group, a piperidine group, a piperazine group, a pyrimidyl group, a furyl group, a thienyl group, a benzoxazol-2-yl group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, and a morphonyl group, as well as groups in which one or more hydrogen atoms of an alkyl group are substituted with a heterocycle. Furthermore, examples of the heterocycle-containing group having a substituent include groups in which one or more hydrogen atoms in the unsubstituted heterocycle-containing group have been substituted with a substituent, and examples of the substituent include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, and -COOH.

[0041] Furthermore, the unsubstituted heterocycle-containing group may be a group in which a heterocycle and an aromatic hydrocarbon ring of a monocyclic structure are linked together, or a group in which a heterocycle and an aromatic hydrocarbon ring of a fused ring structure are linked together. Examples of the linking group linking two aromatic hydrocarbon rings include a single bond and a carbonyl group. Examples of the heterocycle-containing group in which a heterocycle and an aromatic hydrocarbon ring of a monocyclic structure are linked together include benzothiophene.

[0042] In the general formula (A) and the general formula (1), the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group, or the heterocyclic ring-containing group in which one or more methylene groups have been replaced with a divalent group selected from Group I does not have a structure in which multiple divalent groups are adjacent to each other. The multiple divalent groups may be the same or different.

[0043] In the present invention, when a hydrogen atom in a group is substituted with a substituent, the number of carbon atoms in the group refers to the number of carbon atoms in the group after the substitution. For example, in the case of a group in which a hydrogen atom of an alkyl group having 1 to 20 carbon atoms is substituted with a substituent, the number of carbon atoms of 1 to 20 refers to the number of carbon atoms after the hydrogen atom is substituted, not the number of carbon atoms before the hydrogen atom is substituted. In the present invention, the number of carbon atoms in a group in which a methylene group in a group with a predetermined number of carbon atoms is replaced with a divalent group defines the number of carbon atoms in the group after the substitution. For example, in the case of a group in which a methylene group in an alkyl group having 1 to 20 carbon atoms is replaced with a divalent group, the term "1 to 20 carbon atoms" refers to the number of carbon atoms after the methylene group is replaced with the divalent group, not the number of carbon atoms before the substitution.

[0044] The aromatic ring group having 6 to 20 carbon atoms represented by A in the above general formula (A) (hereinafter, may be referred to as aromatic ring group A) means a structure containing an aromatic ring and having 6 to 20 carbon atoms, and contains at least either an aromatic hydrocarbon ring or an aromatic heterocycle. Furthermore, the "6 to 20 carbon atoms" in the aromatic ring group A having 6 to 20 carbon atoms refers to the number of carbon atoms forming the ring skeleton of the aromatic ring contained in the aromatic ring group. Furthermore, when the aromatic ring group has a linking structure, it refers to the total number of carbon atoms forming the ring skeleton of the aromatic ring. For example, a tolyl group, an indole ring group, and a diphenyl sulfide group are aromatic ring groups having 6, 8, and 12 carbon atoms, respectively. The aromatic ring contained in the aromatic ring group A may have a monocyclic structure or a polycyclic structure. In the case of a polycyclic structure, it may be a fused ring structure, or may be a structure in which an aromatic ring of a monocyclic structure and an aromatic ring of a monocyclic structure are linked together, or may be a structure in which aromatic rings are linked together, such as a structure in which an aromatic ring of a monocyclic structure and an aromatic ring of a fused ring structure are linked together, or a structure in which aromatic rings are linked together, such as a structure in which an aromatic ring of a fused ring structure and an aromatic ring of a fused ring structure are linked together. The linking group that links the aromatic rings may be any group that can make the aryl group as a whole aromatic, and examples thereof include a single bond, a sulfide group (-S-), and a carbonyl group. In the present invention, the aromatic ring group A preferably has a polycyclic structure, because this allows the radical polymerization initiator to more effectively exhibit the effect of excellent stability of sensitivity.

[0045] The aromatic hydrocarbon ring means a structure containing an aromatic hydrocarbon ring but not a heterocycle, and examples thereof include single ring structures or condensed ring structures such as a cyclobutadiene ring, a benzene ring, a cyclooctatetraene ring, a cyclotetradecaheptaene ring, a cyclooctadecanonaene ring, a naphthalene ring, and an anthracene ring, as well as linked structures such as a triphenylamine structure, a diphenyl sulfide structure, and a fluorene ring. In the present invention, the aromatic hydrocarbon ring is preferably a polycyclic structure, and more preferably a linked structure or a fused ring structure. The linking structure is preferably a diphenyl sulfide structure in which the linking group is a sulfide group, because this allows the radical polymerization initiator to more effectively exhibit the effect of excellent stability of sensitivity. The fused ring structure may be one in which two or more ring structures are fused, but one in which two to four ring structures are fused is preferred, one in which two to three ring structures are fused is more preferred, and one in which three ring structures are fused is particularly preferred, and among these, a fluorene ring is particularly preferred, because this allows the radical polymerization initiator to more effectively exhibit the effect of excellent sensitivity stability.

[0046] The aromatic heterocycle means a structure containing an aromatic heterocycle, and examples thereof include a monocyclic structure or a fused ring structure such as a furan ring, a thiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a carbazole ring, and an indole ring. In the present invention, the aromatic heterocycle preferably has a polycyclic structure, and more preferably a fused ring structure, because the radical polymerization initiator can more effectively exhibit the effect of excellent sensitivity stability. The fused ring structure may be one in which two or more ring structures are fused, but one in which two to four ring structures are fused is preferred, one in which two to three ring structures are fused is preferred, and one in which two ring structures are fused is preferred, because this allows the radical polymerization initiator to more effectively exhibit the effect of excellent sensitivity stability. The condensed structure of two rings is preferably an indole ring, because this allows the radical polymerization initiator to more effectively exhibit the effect of excellent stability of sensitivity. The three condensed ring structures are preferably carbazole rings, because this allows the radical polymerization initiator to more effectively exhibit the effect of excellent stability of sensitivity.

[0047] In the general formula (A), a represents an integer of 1 to 19. When a is an integer of 2 or more, a plurality of R 31 may be the same or different. In the general formula (A), b represents an integer of 0 to 19. When b is an integer of 2 or more, a plurality of R 32 may be the same or different. In the general formula (A), c represents an integer of 0 to 19. When c is an integer of 2 or more, a plurality of R 33 may be the same or different. In the general formula (A), a+b+c is 20 or less, provided that a+b+c is the upper limit of the number of bonds that can be made in the aromatic ring group A. a may be any number that provides desired stability of sensitivity, and is preferably 1 to 3, more preferably 1 or 2, and most preferably 1. When a is in the above range, the radical polymerization initiator can effectively exhibit the effect of excellent stability of sensitivity. b may be any number that provides desired stability of sensitivity, and is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 to 1. When b is in the above-mentioned range, the radical polymerization initiator can effectively exhibit the effect of excellent stability of sensitivity. c may be any number that provides desired stability of sensitivity, and is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 to 1. When c is in the above-mentioned range, the radical polymerization initiator can effectively exhibit the effect of excellent stability of sensitivity.

[0048] The group represented by the general formula (1) is a group that bonds to the aromatic ring group A, and bonds by substituting a hydrogen atom that is bonded to an atom that constitutes the ring structure of the aromatic ring in the aromatic ring group. R used in the above general formula (1) 1 R is preferably an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or the aliphatic hydrocarbon group in which one or more methylene groups have been substituted with a group represented by Group I above, more preferably an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or the aliphatic hydrocarbon group in which one or more methylene groups have been substituted with a group represented by Group I above, and particularly preferably an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. 1 is the above group, the radical polymerization initiator can effectively exhibit the effect of excellent stability of sensitivity.

[0049] Above R 1The unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms used in the present invention is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, more preferably a linear or branched alkyl group having 2 to 10 carbon atoms, still more preferably a linear or branched alkyl group having 4 to 8 carbon atoms, and particularly preferably a linear alkyl group having 4 to 8 carbon atoms. This is because the radical polymerization initiator can effectively exhibit the effect of excellent sensitivity stability.

[0050] R used in the above general formula (1) 2 The radical polymerization initiator is preferably an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a linear or branched alkyl group having 1 to 20 carbon atoms, even more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, and particularly preferably a linear alkyl group having 1 to 3 carbon atoms. This is because the radical polymerization initiator can effectively exhibit the effect of excellent sensitivity stability.

[0051] In the general formula (A), the radical generating group other than the general formula (1) means a radical generating group that does not have an oxime ester group, and examples thereof include groups represented by the following general formulae (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg), and (IVh). The radical generating group other than the one represented by the general formula (1) is a group that is bonded to the aromatic ring group A, and is bonded by substituting a hydrogen atom that is bonded to an atom that constitutes the ring structure of the aromatic ring in the aromatic ring group.

[0052] [ka] (In the formula, R 51 is OR 81 , N.R. 82 R 83 or an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, R 52 and R 53 are each independently R 81 OR81 represents R 52 and R 53 may be bonded to form a ring, R 55 , R 56 , R 58 , R 59 , R 61 , R 62 , R 64 , R 65 , R 71 and R 73 represents an unsubstituted or substituted aryl group having 6 to 20 carbon atoms, R 54 , R 57 , R 60 , R 63 , R 66 , R 67 and R 72 each independently represents an unsubstituted or substituted arylene group having 6 to 20 carbon atoms or a single bond, R 68 represents an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, R 69 and R 70 are each independently R 81 OR 81 represents R 81 , R 82 and R 83 each independently represents a hydrogen atom or an unsubstituted or substituted hydrocarbon group having 1 to 20 carbon atoms, * represents a bond.)

[0053] The hydrocarbon group having 1 to 20 carbon atoms used in the above general formulae (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg) and (IVh) includes an aliphatic hydrocarbon group having 1 to 20 carbon atoms and an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms. The arylene group having 6 to 20 carbon atoms used in the above general formulae (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg) and (IVh) includes a divalent group in which one hydrogen atom has been removed from an aryl group having 6 to 20 carbon atoms. R used in the above general formulas (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg) and (IVh) 52 and R 53 The ring formed by bonding may be a monocyclic ring or a condensed ring. Examples of the monocyclic ring include monocyclic cycloalkanes such as cyclopentane, cyclohexane, and cyclopentene, monocyclic aromatic rings such as benzene, and monocyclic heterocyclic rings such as pyrrolidine, pyrrole, piperazine, morpholine, thiomorpholine, tetrahydropyridine, lactone rings, and lactam rings. Examples of the condensed ring include naphthalene and anthracene. The aliphatic hydrocarbon groups having 1 to 20 carbon atoms, aromatic hydrocarbon ring-containing groups having 6 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, and heterocyclic ring-containing groups having 2 to 20 carbon atoms used in the above general formulae (IVa), (IVb), (IVc), (IVd), (IVe), (IVf), (IVg), and (IVh) can be the same as those used in general formula (A) and the above general formula (1). Furthermore, in the heterocycle-containing group having a substituent, the aryl group having a substituent, the arylene group having a substituent, and the hydrocarbon group having a substituent, examples of the substituent substituting one or more hydrogen atoms in the heterocycle-containing group, the aryl group, the arylene group, and the hydrocarbon group include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, and -COOH.

[0054] In the present invention, the compound A is preferably a compound represented by the following general formula (A1) or (A2), and more preferably a compound represented by the following general formula (A1), because this provides the radical polymerization initiator with better sensitivity stability.

[0055] [ka] (In the formula, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each independently a hydrogen atom, R in the above general formula (A), 31 and R in the above general formula (A). 32 or a group represented by R in the above general formula (A) 33 is a group represented by R 11 and R 12 , R 12 and R 13 , R 14 and R 15 , R 15 and R 16 or R 16 and R 17 may be bonded to each other to form a ring, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the R 31 is a group represented by

[0056] R 11 and R 12 , R 12 and R 13 , R 14 and R 15 , R 15 and R 16 or R 16 and R 17 However, the ring formed by bonding to each other may be a monocyclic ring or a condensed ring. Examples of the monocyclic ring include monocyclic cycloalkanes such as cyclopentane, cyclohexane, and cyclopentene, monocyclic aromatic rings such as benzene, and monocyclic heterocyclic rings such as pyrrolidine, pyrrole, piperazine, morpholine, thiomorpholine, tetrahydropyridine, lactone rings, and lactam rings. Examples of the condensed ring include naphthalene and anthracene.

[0057] [ka] (In the formula, R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 and R 28 are each independently a hydrogen atom, R in the above general formula (A), 31 and R in the above general formula (A). 32 or a group represented by R in the above general formula (A) 33 is a group represented by R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 or R 27 and R 28 may be bonded to each other to form a ring, X 1 is a single bond, no bond, oxygen atom, sulfur atom, selenium atom, CR 41 R 42 , CO, NR 43 or PR 44 and X 2 is an oxygen atom, a sulfur atom, a selenium atom, a CR 41 R 42 , CO, NR 43 or PR 44 and R 41 , R 42 , R 43 and R 44 are each independently a hydrogen atom, R in the above general formula (A), 31 and R in the above general formula (A). 32 or a group represented by R in the above general formula (A) 33 is a group represented by

[0058] R 21 and R 22 , R22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 or R 27 and R 28 However, the ring formed by bonding together is R 11 and R 12 The ring formed by bonding of the above may be the same as those exemplified above.

[0059] In the present invention, R in the above general formula (A1) 11 is R in the above general formula (A). 31 That is, it is preferable that R in the above general formula (A1) 11 is preferably a group represented by the above general formula (1), because this makes the radical polymerization initiator more stable in sensitivity.

[0060] In addition, R in the above general formula (A1) 13 and R 16 is R in the above general formula (A). 33 That is, it is preferable that R in the above general formula (A1) 13 and R 16 At least one of the following is a halogen atom, a nitro group, a cyano group, -OR 34 , -COR 34 , -OCOR 34 , -COOR 34 , -SR 34 , -SOR 34 , -SO2R 34 , -NR 35 R 36 , -NR 35 COR 36 , -CONR 35 R 36, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, an unsubstituted or substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group, or the above heterocyclic ring-containing group are replaced by a divalent group selected from the following Group I, R 34 , R 35 and R 36 each independently represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon ring-containing group, or heterocyclic ring-containing group have been replaced with a divalent group selected from the following Group I; R 34 , R 35 or R 36 When a plurality of groups are present, they may be the same or different, and the substituent substituting one or more hydrogen atoms in the aliphatic hydrocarbon group having the above substituent, the aromatic hydrocarbon ring-containing group having the above substituent, and the heterocycle-containing group having the above substituent is preferably a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, or -COOH, because this provides the radical polymerization initiator with better sensitivity stability.

[0061] In the present invention, R 13 is R in the above general formula (A). 33 It is preferable that R 13 R used in 33 is preferably an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or a group in which one or more methylene groups in the aromatic hydrocarbon ring-containing group have been replaced with a divalent group selected from Group I above. 13 When the radical polymerization initiator has the above structure, the sensitivity stability of the radical polymerization initiator is improved.

[0062] R 13 The "aromatic hydrocarbon ring-containing group" in the unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms used in R is preferably an aryl group having 6 to 20 carbon atoms and a monocyclic structure or a structure in which aromatic hydrocarbon rings are linked, more preferably an aryl group having 12 to 18 carbon atoms and a structure in which aromatic hydrocarbon rings are linked, particularly preferably an aryl group having 12 to 15 carbon atoms and a structure in which aromatic hydrocarbon rings are linked, and among these, an aryl group having 12 to 15 carbon atoms and a structure in which aromatic hydrocarbon rings are linked via a carbonyl group is particularly preferred. 13 When the radical polymerization initiator has the above structure, the sensitivity stability of the radical polymerization initiator is improved.

[0063] R 16 represents a hydrogen atom or R in the above general formula (A). 33 However, it is preferably a hydrogen atom or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, and particularly preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom. When R16 has the above structure, the radical polymerization initiator has better stability of sensitivity.

[0064] R 11 , R 13 and R 16 is the group described above, R 12 , R 14 , R 15 and R 17 represents a hydrogen atom or R in the above general formula (A). 33 However, it is preferably a hydrogen atom or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, particularly preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom.12 , R 14 , R 15 and R 17 When the radical polymerization initiator has the above structure, the sensitivity stability of the radical polymerization initiator is improved.

[0065] In the present invention, R in the above general formula (A1) 11 is a group represented by the general formula (1), and R 13 But R 33 and R 13 R used in 33 is an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or a group in which one or more methylene groups in the aromatic hydrocarbon ring-containing group are substituted with a divalent group selected from Group I above, and R 12 , R 14 , R 15 , R 16 and R 17 is more preferably a hydrogen atom, because the radical polymerization initiator has better stability of sensitivity.

[0066] Preferable specific examples of the compound represented by the general formula (A1) include those exemplified in WO 2015 / 152153 and the like.

[0067] Of the compounds represented by the above general formula (A2), preferred compounds include, for example, compounds represented by the following general formulae (A21), (A22) and (A23).

[0068] [ka] (In the formula, R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 41 , R 42 and R 43is the same as in general formula (A2) above.

[0069] As the compound represented by the above general formula (A2), compounds described in WO 2008 / 078678, JP 2011-132215 A, etc. can be used.

[0070] The compound represented by the general formula (A) can be produced by known methods described in WO 2015 / 152153, WO 2008 / 078678, JP 2011-132215, and the like. For example, among the compounds represented by the above general formula (A1) (compound A1), a compound in which n in the above general formula (1) is 0 can be produced by the following method in accordance with the reaction formula shown in Example 1 below. Specifically, ketone body 1 is reacted with a halide to obtain ketone body 2, and ketone body 2 is reacted with hydroxylamine hydrochloride to obtain oxime compound 3. Subsequently, the oxime compound 3 is reacted with acid anhydride 4, acid chloride 4', or carboxylate 4", thereby producing the above compound A1. Compound A1, where n is 1 in the above general formula (1), can also be produced in accordance with the reaction scheme shown in Example 2 below, similar to compound A1, where n is 0.

[0071] [ka] (In the formula, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 is the same as in general formula (A1) above.

[0072] [ka] (In the formula, R 11 , R 12 , R 13 , R 14 , R 15, R 16 and R 17 is the same as in general formula (A1) above.

[0073] The content of the compound A is preferably 70 parts by mass or more, more preferably 80 parts by mass or more, and particularly preferably 90 parts by mass or more, per 100 parts by mass of the radical polymerization initiator, because this provides the radical polymerization initiator with better sensitivity stability.

[0074] The content of the compound A is preferably 70 parts by mass or more, more preferably 80 parts by mass or more, and particularly preferably 90 parts by mass or more, per 100 parts by mass of the solid content of the radical polymerization initiator, because this provides the radical polymerization initiator with better sensitivity stability. The solid content refers to the total of all components other than the solvent (water and organic solvent).

[0075] 2. Acid component The acid component is contained as a component other than the compound A, and is a proton (H + ) can be provided. Therefore, the compound A having an acidic group such as a carboxyl group is not included in the acid component.

[0076] As such an acid component, either an organic acid having a carbon atom or an inorganic acid having no carbon atom can be used. In the present invention, the acid component is preferably an organic acid, because the type of the acid component is within the above range, and the radical polymerization initiator has better stability of sensitivity.

[0077] The normality of the acid component may be 1N, such as acetic acid, or 2N or higher, such as oxalic acid. In the present invention, the normality of the acid component is preferably 1 or more and 3 or less, more preferably 1 or more and 2 or less, and more preferably 1. When the normality is within the above range, the radical polymerization initiator becomes more excellent in sensitivity stability.

[0078] The molecular weight of the acid component is preferably 250 or less, more preferably 200 or less, and particularly preferably from 50 to 100. This is because the radical polymerization initiator has better stability of sensitivity.

[0079] The acid group of the acid component is preferably a carboxy group, a sulfonic acid group, a phosphoric acid group, a nitric acid group, or a boric acid group, and is particularly preferably a carboxy group, because this provides the radical polymerization initiator with better sensitivity stability.

[0080] Examples of organic acids include aliphatic monocarboxylic acids having 1 to 18 carbon atoms, such as formic acid, acetic acid, propionic acid, butyric acid, and lactic acid; aliphatic dicarboxylic acids having 1 to 12 carbon atoms, such as oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, and adipic acid; aromatic carboxylic acids, such as benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, and salicylic acid; and sulfonic acids having 1 to 20 carbon atoms, such as methanesulfonic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, and trifluoromethanesulfonic acid. Examples of inorganic acids include hydrochloric acid, hydrobromic acid, sulfuric acid, sulfurous acid, phosphoric acid, phosphorous acid, polyphosphoric acid, nitric acid, boric acid, and perchloric acid.

[0081] In the present invention, the organic acid is more preferably an aliphatic monocarboxylic acid having 1 to 18 carbon atoms or an aliphatic dicarboxylic acid having 1 to 12 carbon atoms, of which an aliphatic monocarboxylic acid having 1 to 18 carbon atoms is more preferable, and particularly an aliphatic monocarboxylic acid having 1 to 10 carbon atoms is more preferable, and particularly an aliphatic monocarboxylic acid having 1 to 5 carbon atoms is more preferable, and particularly an aliphatic monocarboxylic acid having 2 to 4 carbon atoms is more preferable, and particularly acetic acid is preferable, because this provides the radical polymerization initiator with better sensitivity stability.

[0082] The organic acids and inorganic acids may be used alone or in combination of two or more.

[0083] The content of the acid component in the total of the compound A and the acid component is from 1 ppm to 400 ppm, more preferably from 3 ppm to 200 ppm, and particularly preferably from 5 ppm to 30 ppm, because this provides the radical polymerization initiator with better sensitivity stability. The content of the acid component is based on mass. The content of the acid component can be determined by ion chromatography.

[0084] The content of the acid component in the radical polymerization initiator is preferably 1 ppm or more and 400 ppm or less, more preferably 3 ppm or more and 200 ppm or less, and particularly preferably 5 ppm or more and 30 ppm or less, because this makes the radical polymerization initiator more excellent in sensitivity stability. The content of the acid component is based on mass.

[0085] 3. Solvent The radical polymerization initiator contains compound A and an acid component, and may contain a solvent as needed. The solvent is liquid at room temperature (25°C) and atmospheric pressure and is capable of dispersing or dissolving compound A, the acid component, and other components described below. Therefore, even if the solvent is liquid at room temperature (25°C) and atmospheric pressure, compound A and the acid component are not included in the solvent. Examples of the solvent include water and organic solvents described in "3. Solvent" in "B. Composition" below. The content of the solvent may be any amount as long as the desired stability of sensitivity is obtained, and can be 1 part by mass or more and 99 parts by mass or less per 100 parts by mass of the radical polymerization initiator.

[0086] The radical polymerization initiator may contain water as needed, provided that the desired stability of sensitivity can be obtained. The content of water is preferably 5% by mass or less, more preferably 1% by mass or less, particularly preferably 0.5% by mass or less, and even more preferably 0.1% by mass or less, based on the total of compound A, the acid component, and water. When the content of water is within the above range, the radical polymerization initiator has better stability of sensitivity. The lower limit of the water content is not particularly limited as long as the desired stability of sensitivity is obtained, but it can be set to 0.01% by mass or more from the viewpoint of ease of preparation and storage of the radical polymerization initiator. The water content can be measured by the Karl Fischer method.

[0087] 4. Other ingredients The radical polymerization initiator contains compound A and an acid component, and may contain a solvent, but may also contain other components as necessary. Examples of such other components include the components described in the section "4. Other Components" under "B. Composition" below. The other components may include compounds having a structure other than that of Compound A as radical-generating compounds.

[0088] 5. Radical polymerization initiator The radical polymerization initiator generates radicals. The method for generating radicals from the radical polymerization initiator may be any method commonly used for radical generators, and specific examples include a method of irradiating with energy rays, a method of heat treatment, a method of performing these methods simultaneously or sequentially, etc. That is, the radical polymerization initiator may be a photoradical polymerization initiator that generates radicals by irradiation with energy rays, or a thermal radical polymerization initiator that generates radicals by heat treatment.

[0089] Examples of the energy rays include g-rays (436 nm), h-rays (405 nm), i-rays (365 nm), visible light, ultraviolet rays, far ultraviolet rays, X-rays, and charged particle rays. In the present invention, the energy rays used for generating radicals preferably have a maximum spectrum in the wavelength range of 300 nm to 400 nm within the wavelength range of 200 nm to 450 nm, and more preferably have a maximum spectrum in the wavelength range of 340 nm to 380 nm, because this allows radicals to be generated effectively from the radical polymerization initiator.

[0090] Examples of light sources for the energy rays include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, metal halogen lamps, electron beam irradiation devices, X-ray irradiation devices, and lasers (argon lasers, dye lasers, nitrogen lasers, light-emitting diodes (LEDs), helium-cadmium lasers, etc.).

[0091] The exposure dose of the energy ray is not particularly limited as long as it can generate a desired amount of radicals, and can be appropriately determined depending on the application of the compound A. The exposure dose is 5 mJ / cm 2 More than 2000mJ / cm 2 The following are preferred because they allow radicals to be generated effectively from the radical polymerization initiator.

[0092] The heating temperature in the heat treatment is, for example, preferably 70° C. or more and 450° C. or less, and more preferably 150° C. or more and 300° C. or less. The heating time in the heat treatment is, for example, preferably 1 minute or more and 100 minutes or less, because this allows radicals to be generated effectively from the radical polymerization initiator.

[0093] The radical polymerization initiator may be in the form of a powder or pellets. When the radical polymerization initiator is in the form of pellets, for example, an example of a method for producing the radical polymerization initiator is to mix the compound A, the acid component, and other components using an extruder or the like, and then mold the mixture into pellets. The radical polymerization initiator may be in the form of a solution in which the compound A and the acid component are dispersed or dissolved in a solvent.

[0094] The radical polymerization initiator can be used, for example, in a curable composition containing a radically polymerizable compound.

[0095] Applications of the curable compositions include, for example, photocurable paints or varnishes, photocurable adhesives, printed circuit boards, color filters in color display liquid crystal display elements for color televisions, PC monitors, personal digital assistants, digital cameras, etc., electrode materials for plasma display panels, powder coatings, printing inks, printing plates, adhesives, dental compositions, gel coats, photoresists for electronics, electroplating resists, etching resists, both liquid and dry films, solder resists, resists for producing color filters for various display applications or for forming structures in the manufacturing process of plasma display panels, electroluminescent displays, and LCDs, and resists for encapsulating electrical and electronic components. The present invention can be used for a variety of applications, including, but not limited to, compositions for producing three-dimensional objects by stereolithography, magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etching masks, color test systems, glass fiber cable coatings, screen printing stencils, materials for producing three-dimensional objects by stereolithography, holographic recording materials, image recording materials, fine electronic circuits, bleaching materials, bleaching materials for image recording materials, bleaching materials for image recording materials using microcapsules, photoresist materials for printed wiring boards, photoresist materials for UV and visible laser direct imaging systems, and photoresist materials or protective films used to form dielectric layers in the sequential lamination of printed circuit boards. Further, examples of applications of the curable composition include compositions for forming optical components such as color filters, partition materials, and insulating films used in organic electroluminescence (organic EL) displays, quantum dot (QD) displays, and micro light-emitting diode (μLED) displays. The curable composition can be used in a variety of applications, including polymerizable liquid crystal coating compositions, conductive pastes, and curable ink compositions such as UV-curable inks. The curable composition can be used in a variety of applications, including compositions for forming insulating members in electronic substrate circuits, such as solder resists used in semiconductor packages, resists for forming circuits, and resists for bumps.

[0096] B. Composition Next, the composition of the present invention will be described. The composition of the present invention is characterized by containing the above-mentioned radical polymerization initiator and a radical polymerizable compound.

[0097] The composition of the present invention contains the radical polymerization initiator, and thus has excellent stability of sensitivity.

[0098] 1. Radical polymerization initiator The content of the radical polymerization initiator in the composition of the present invention is not particularly limited as long as it can impart the desired curability and the like to the composition. The content of the radical polymerization initiator in the composition of the present invention can be, for example, 0.001 parts by mass or more and less than 30 parts by mass, and preferably 0.005 parts by mass or more and 10 parts by mass or less, per 100 parts by mass of the solid content of the composition, because this provides the composition with more excellent sensitivity stability. The solid content includes all components other than the solvent.

[0099] The content of the radical polymerization initiator is preferably from 0.1 to 50 parts by mass, more preferably from 1 to 30 parts by mass, and particularly preferably from 5 to 20 parts by mass, relative to 100 parts by mass of the radical polymerizable compound, because this provides the composition with more excellent sensitivity stability.

[0100] The above-mentioned radical polymerization initiator is the same as that described in the section "A. Radical polymerization initiator."

[0101] 2. Radical polymerizable compounds The radically polymerizable compound may be any compound capable of radical polymerization, and examples thereof include compounds having an ethylenically unsaturated double bond such as an acrylic group, a methacrylic group, or a vinyl group. The radical polymerizable compound has one or more radical polymerizable groups, and may be either a monofunctional compound having one radical polymerizable group or a polyfunctional compound having two or more radical polymerizable groups.

[0102] The radically polymerizable compound may be either a compound having an acid value or a compound having no acid value. Examples of compounds having the above acid value include acrylate compounds and methacrylate compounds having a carboxy group such as methacrylic acid and acrylic acid. Examples of the compound having the above acid value include a polymer containing a structural unit having a carboxy group and a structural unit having an ethylenically unsaturated group. Examples of the compound having no acid value include urethane acrylate resin, urethane methacrylate resin, epoxy acrylate resin, epoxy methacrylate resin, acrylate compounds and methacrylate compounds having no carboxy group, such as 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate.

[0103] The radical polymerizable compounds can be used alone or in combination of two or more. For example, a compound having an ethylenically unsaturated group and an acid value and a compound having an ethylenically unsaturated group and no acid value can be used in combination as the radical polymerizable compound. When two or more kinds of radical polymerizable compounds are used in combination, they may be copolymerized in advance and used as a copolymer. More specifically, such radical polymerizable compounds include the radical polymerizable compounds described in JP 2016-176009 A and polymerizable compounds having a radical polymerizable group described in WO 2019 / 088055 A. Examples of polymers that include a structural unit having a carboxyl group and a structural unit having an ethylenically unsaturated group include polymers that include a structural unit having a carboxyl group [A] as described in JP 2016-151744 A, which include a structural unit having a (meth)acryloyl group as a structural unit (A2) having a crosslinkable group, and polymers that include a structural unit having a methacryloyl group or an acryloyl group as a structural unit (U2) among polymers having a hydrophilic group (2) as described in WO 2019 / 088055 A.

[0104] The content of the radical polymerizable compound is not particularly limited as long as it can produce a desired cured product, but for example, it can be from 1 to 50 parts by mass, preferably from 5 to 40 parts by mass, more preferably from 8 to 30 parts by mass, and particularly preferably from 10 to 20 parts by mass, per 100 parts by mass of the solid content of the composition, because this gives the composition excellent curability.

[0105] 3. Solvent The composition may contain a solvent in addition to the radical polymerization initiator and the radical polymerizable compound. The solvent is a liquid at room temperature (25°C) and atmospheric pressure, and is capable of dispersing or dissolving the radical polymerization initiator, the radical polymerizable compound, and other components described below. Therefore, even if the solvent is a liquid at room temperature (25°C) and atmospheric pressure, the radical polymerization initiator and the radical polymerizable compound are not included in the solvent.

[0106] The solvent may be either water or an organic solvent. In the present invention, the solvent is preferably an organic solvent, since it is easy to dissolve or disperse the radical polymerization initiator and the radical polymerizable compound.

[0107] Examples of the organic solvent include carbonates such as propylene carbonate and diethyl carbonate; ketones such as acetone and 2-heptanone; ether esters such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol-1-monomethyl ether-2-acetate, dipropylene glycol monomethyl ether acetate, 3-methoxybutyl ether acetate, and ethoxyethyl ether propionate; polyhydric alcohols such as ethylene glycol, propylene glycol, propylene glycol monoacetate, and dipropylene glycol; cyclic ethers such as dioxane; esters such as ethyl formate and 3-methyl-3-methoxybutyl acetate; aromatic hydrocarbons such as toluene and xylene; and lactones such as γ-caprolactone and δ-caprolactone. In the present invention, the organic solvent preferably contains an ether ester, since this makes it easy to prepare a composition with excellent dispersion stability.

[0108] The content of the solvent can be 1 part by mass or more and 99 parts by mass or less in 100 parts by mass of the composition.

[0109] 4.Other The composition may contain other components as needed in addition to the radical polymerization initiator, radical polymerizable compound, and solvent. Examples of the other components include polymerizable compounds, polymers having hydrophilic groups, colorants, inorganic compounds, organic polymers other than polymers having hydrophilic groups, chain transfer agents, sensitizers, surfactants, silane coupling agents, melamine, colorants, dispersants for dispersing inorganic compounds, etc. Examples of the other components include those described as other components in WO 2019 / 088055. Examples of polymers having hydrophilic groups that can be used include copolymers [A] described in JP 2005-234362 A, which are copolymers of (a1) unsaturated carboxylic acids and / or unsaturated carboxylic anhydrides, (a2) epoxy group-containing unsaturated compounds, and (a3) ​​other unsaturated compounds; polymers containing structural units having carboxyl groups [A] described in JP 2016-151744 A; and polymers having hydrophilic groups (2) described in WO 2019 / 088055 A that do not contain structural units having radical polymerizable groups such as methacryloyl groups or acryloyl groups. The content of the above additives is appropriately selected depending on the purpose of use and is not particularly limited, but for example, it can be 50 parts by mass or less in total, and preferably 30 parts by mass or less, per 100 parts by mass of the solid content of the composition.

[0110] 4. Composition The composition may be produced by any known mixing method as long as it is capable of mixing the components to the desired content. The composition can be used, for example, as a photocurable composition that is cured by irradiation with light. Specific uses are the same as those described in the section "A. Radical polymerization initiator" above.

[0111] C. Cured product Next, the cured product of the present invention will be described. The cured product of the present invention is a cured product of the above-described composition.

[0112] The cured product of the present invention uses the above-mentioned composition, and therefore the durability and other properties can be easily adjusted. The above composition is the same as that described in the section "B. Composition" above.

[0113] The uses of the cured product are the same as those described in the section "A. Radical polymerization initiator."

[0114] The method for producing the cured product is not particularly limited as long as it is a method that can form a cured product of the composition into a desired shape. Examples of such a production method include the production method described in the section "D. Production method of cured product" below.

[0115] D. Manufacturing method of cured product Next, the method for producing the cured product of the present invention will be described. The method for producing a cured product of the present invention is characterized by having a polymerization step of polymerizing radically polymerizable compounds in the above-mentioned composition.

[0116] The method for producing a cured product of the present invention uses the above-described composition in the polymerization step, and therefore can easily produce a cured product with desired durability and the like.

[0117] 1. Polymerization process The polymerization step in the present invention is a step of curing the above-mentioned composition. The method for curing the composition may be any method that can polymerize radically polymerizable compounds together to cure the composition, and examples thereof include a method in which radicals are generated from the radical polymerization initiator. The method for generating radicals from the radical polymerization initiator may be any method that can generate a desired amount of radicals from the radical polymerization initiator, and examples thereof include a method of irradiating with energy rays, a method of heat treatment, and a method of performing these simultaneously or sequentially. Examples of such a method of irradiating with energy rays, a method of heat treatment, etc. include the same methods as those described in the section "A. Radical Polymerization Initiator" above.

[0118] In this step, the method for generating the radicals preferably includes a method of irradiating with energy rays, because radicals can be effectively generated from the radical polymerization initiator and the radical polymerizable compound can be effectively cured. The composition is the same as that described in the section "B. Composition" above.

[0119] 2. Other processes The method for producing a cured product of the present invention may include other steps in addition to the polymerization step, if necessary. Examples of the other steps include a development step in which unpolymerized portions in the coating film of the composition are removed after the polymerization step to obtain a patterned cured product; a post-baking step in which the cured product is heat-treated after the polymerization step; a pre-baking step in which the composition is heat-treated to remove the solvent in the composition before the polymerization step; and a step in which a coating film of the composition is formed before the polymerization step. In the present invention, the other steps preferably include a post-baking step, because this allows the radicals generated from the radical polymerization initiator to be effectively diffused, and as a result, it becomes easy to form a cured product in which the polymerization of the radical polymerizable compound has progressed sufficiently.

[0120] As a method for removing the unpolymerized portions in the development step, for example, a method of applying a developer such as an alkaline developer to the unpolymerized portions can be mentioned. As the alkaline developer, those generally used as alkaline developers such as an aqueous solution of tetramethylammonium hydroxide (TMAH), an aqueous solution of potassium hydroxide, an aqueous solution of potassium carbonate, etc. can be used. As the developer, a solvent developer such as propylene glycol monomethyl ether acetate (PEGMEA) or cyclohexanone that is generally used can be used. The developing method using the developer may be any method that can bring the developer into contact with the area to be developed, and known methods such as showering, spraying, and immersion can be used. The developing step may be carried out after the curing step.

[0121] The heating conditions in the post-baking step may be any conditions that can improve the strength of the cured product obtained in the curing step, and may be, for example, 200° C. or higher and 250° C. or lower for 20 to 90 minutes.

[0122] The heating conditions in the pre-baking step may be any conditions that can remove the solvent in the composition, and may be, for example, at 70° C. or higher and 150° C. or lower for 30 to 300 seconds.

[0123] In the step of forming the coating film, the composition can be applied by any known method such as using a spin coater, roll coater, bar coater, die coater, curtain coater, various types of printing, or dipping. The coating film can be formed on a substrate. The substrate can be appropriately selected depending on the intended use of the cured product, and examples thereof include soda glass, quartz glass, semiconductor substrates, wiring substrates, metals, paper, plastics, and the like. Furthermore, after the cured product is formed on a substrate, it may be peeled off from the substrate and used, or may be transferred from the substrate to another adherend and used.

[0124] 3.Other The cured product produced by the above production method and its uses are the same as those described in the section "C. Cured product" above.

[0125] The present invention is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any configuration that is substantially identical to the technical idea described in the claims of the present invention and that provides similar effects is included within the technical scope of the present invention. [Example]

[0126] EXAMPLES The present invention will be explained in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples.

[0127] [Manufacturing Examples 1 to 7] Compounds No. 1, No. 3, No. 5, No. 71, No. 73, No. 77, and No. 131 shown below were synthesized as Compound A by the method described in WO 2015 / 152153. 1 The results of H-NMR measurement are shown in Table 1.

[0128] [ka]

[0129] [Table 1]

[0130] [Manufacturing Examples 8-62] Compounds A-1 to A-55 shown below were synthesized as Compound A by the method described in WO 2015 / 152153. 1 The results of H-NMR measurement are shown in Table 2.

[0131] [ka]

[0132] [ka]

[0133] [ka]

[0134] [ka]

[0135] [ka]

[0136] [Table 2]

[0137] [Production Example 63] Production of blue pigment dispersion A blue pigment dispersion was prepared by dispersing DISPERBYK-161 (12.5 parts by mass; manufactured by BYK Japan) as a dispersant and Pigment Blue 15:6 (15 parts by mass) as a colorant in PGMEA (72.5 parts by mass) using a bead mill.

[0138] [Examples 1 to 67, Comparative Examples 1 to 8] Radical polymerization initiators were prepared by adjusting the acid component for Compound A produced in Production Examples 1 to 62 so as to obtain the formulations shown in Tables 4 to 6. The content of the acid component was quantified by ion chromatography.

[0139] 1. Evaluation of storage stability of Compound A The radical polymerization initiators prepared in the Examples and Comparative Examples were sealed in screw tubes together with air and stored at 60°C for one week. The purity before and after storage was analyzed by high performance liquid chromatography to calculate the decomposition rate, and the stability was evaluated according to the following criteria. The results are shown in Tables 4 to 6. +: Decomposition rate is less than 1% -: Decomposition rate is 1% or more The decomposition rate is expressed as ("mass content of compound A during the initiation of radical polymerization before storage" - "mass content of compound A in the radical polymerization initiator after storage") / "mass content of compound A during the initiation of radical polymerization before storage" x 100 (%). The smaller the decomposition rate, the better the storage stability.

[0140] 2. Evaluation of sensitivity stability Using the radical polymerization initiators prepared in the Examples and Comparative Examples, compositions were prepared by mixing the components according to the formulations shown in Table 3. The values ​​in Table 3 indicate parts by mass. The components in the table are as follows: A-1: Radical polymerization initiators prepared in Examples 1 to 67 and Comparative Examples 1 to 8 B-1: SPC-3000 (polymer having hydrophilic groups; manufactured by Showa Denko K.K., solid content 42.7%, PGMEA solution) C-1: Kayarad DPHA (polymerizable compound (multifunctional acrylate); manufactured by Nippon Kayaku Co., Ltd.) D-1: Blue pigment dispersion (blue pigment dispersion produced in Production Example 9) E-1: KBE-403 (coupling agent, manufactured by Shin-Etsu Chemical Co., Ltd.) F-1: Propylene glycol-1-monomethyl ether-2-acetate (solvent)

[0141] [Table 3]

[0142] Each composition was spin-coated onto a glass substrate, pre-baked at 90°C for 120 seconds using a hot plate, and then cooled at 23°C for 60 seconds. Thereafter, the coating was exposed to light through a photomask (mask opening 30 μm) using an ultra-high pressure mercury lamp (exposure gap 100 μm, exposure dose 40 mJ / cm). 2 After development using a 0.04% by mass KOH aqueous solution as the developer, the resist was thoroughly rinsed with water and post-baked in a clean oven at 230°C for 20 minutes to fix the pattern. The resulting pattern was observed under an electron microscope, and the line width of the portion corresponding to the mask opening was measured. The sensitivity evaluation was carried out according to the following criteria for the radical polymerization initiator immediately after preparation and for the radical polymerization initiator that had been sealed in a screw tube together with air and stored at 60°C for one week. The results are shown in Tables 2 to 4. +: No difference before and after storage (line width change rate is less than ±10%) -: Differences were observed before and after storage (change in line width was more than ±10%) The smaller the change in line width before and after storage, the more stable the sensitivity can be determined to be. It was also confirmed that the radical polymerization initiators of the examples could be easily and uniformly dissolved or dispersed when mixed with the components of the compositions used for evaluation.

[0143] 3. Moisture content measurement The water content (mass %) in the radical polymerization initiators prepared in the examples and comparative examples was measured using a Karl Fischer moisture meter. The results are shown in Tables 4 to 6. The water content (mass %) shown in the table indicates the water content in the total of compound A, acid component, and water.

[0144] 4. Solubility evaluation of compound A 0.4 g of the radical polymerization initiator prepared in each of the Examples and Comparative Examples and 9.6 g of PGMEA were weighed into a screw tube, and the time required for dissolution was visually confirmed while stirring with a stirrer in an environment at 25°C, and the solubility was evaluated according to the following criteria. The results are shown in Table 7. +: Dissolution time less than 20 seconds -: Dissolving time is 20 seconds or more

[0145] [Table 4]

[0146] [Table 5]

[0147] [Table 6]

[0148] [Table 7]

[0149] From the results shown in Tables 4 to 7, it was confirmed that the radical polymerization initiators of the examples had excellent sensitivity stability. In addition, the radical polymerization initiators of the examples also had excellent storage stability and good solubility in solvents. [Industrial Applicability]

[0150] According to the present invention, a radical polymerization initiator having excellent stability in sensitivity can be provided.

Claims

1. A compound represented by the following general formula (A1), An acid component, A radical polymerization initiator comprising: The radical polymerization initiator, wherein the content of the acid component is 1 ppm or more and 400 ppm or less in the total of the compound represented by general formula (A1) and the acid component. 【Chemistry 1】 (In the formula, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 each independently represent a hydrogen atom, a group represented by the following general formula (1), a radical generating group other than the general formula (1), an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which a hydrogen atom is substituted with a radical generating group other than the general formula (1), an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms in which a hydrogen atom is substituted with a radical generating group other than the general formula (1), an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms in which a hydrogen atom is substituted with a radical generating group other than the general formula (1), or a group in which one or more methylene groups in the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group or the heterocycle-containing group are substituted with a divalent group selected from the following group I, or a halogen atom, a nitro group, a cyano group, -OR 34 , —COR 34 , —OCOR 34 , —COOR 34 , —SR 34 , —SOR 34 , —SO 2 R 34 , —NR 35 R 36 , —NR 35 COR 36 , —CONR 35 R 36 represent an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group or the heterocycle-containing group are replaced with a divalent group selected from the following Group I: R 34 , R 35 and R 36 each independently represent a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group or the heterocyclic ring-containing group have been replaced with a divalent group selected from the following Group I; when a plurality of R 34 , R 35 or R 36 are present, they may be the same or different, the substituent substituting one or more hydrogen atoms in the substituted aliphatic hydrocarbon group, the substituted aromatic hydrocarbon ring-containing group, and the substituted heterocycle-containing group is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, or —COOH; R 11 and R 12 , R 12 and R 13 , R 14 and R 15 , R 15 and R 16 , or R 16 and R 17 may be bonded to each other to form a ring; At least one of R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 is a group represented by the following general formula (1): 【Chemistry 2】 (In the formula, R １ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group, or the heterocycle-containing group have been replaced with a divalent group selected from the following Group I: R ２ represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group, or the heterocycle-containing group have been replaced with a divalent group selected from the following Group I: the substituent substituting one or more hydrogen atoms in the substituted aliphatic hydrocarbon group, the substituted aromatic hydrocarbon ring-containing group, and the substituted heterocycle-containing group is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, or —COOH; n represents 0 or 1; * indicates the bonding site.) Group I: -O-, -COO-, -OCO-, -CO-, -CO-CO-, -CO-CO-O-, -CS-, -S-, -SO-, -SO ２ -, -NR'-, -NR'-CO-, -CO-NR'-, -NR'-COO-, -OCO-NR'- or -SiR'R". R' and R" each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and when there are multiple R' or R", they may be the same or different.

2. The radical polymerization initiator according to claim 1, wherein the acid component is an organic acid.

3. R １１ The radical polymerization initiator according to claim 1, wherein

4. R １３ and R １６ one or more of the above represent a halogen atom, a nitro group, a cyano group, —OR 34 , —COR 34 , —OCOR 34 , —COOR 34 , —SR 34 , —SOR 34 , —SO 2 R 34 , —NR 35 R 36 , —NR 35 COR 36 , —CONR 35 R 36 , an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, an unsubstituted or substituted heterocycle-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon ring-containing group or heterocycle-containing group are replaced with a divalent group selected from the following Group I: R 34 , R 35 and R 36 each independently represent a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or an unsubstituted or substituted heterocyclic ring-containing group having 2 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group or the heterocyclic ring-containing group have been replaced with a divalent group selected from the following Group I; when a plurality of R 34 , R 35 or R 36 are present, they may be the same or different, The radical polymerization initiator according to claim 1, wherein a substituent substituting one or more hydrogen atoms in the substituted aliphatic hydrocarbon group, the substituted aromatic hydrocarbon ring-containing group, and the substituted heterocycle-containing group is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, or —COOH.

5. R １３ is an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, or a group in which one or more methylene groups in the aromatic hydrocarbon ring-containing group are substituted with a divalent group selected from Group I.

6. The radical polymerization initiator according to any one of claims 1 to 5, wherein the content of the compound represented by general formula (A1) is 90 parts by mass or more per 100 parts by mass of the radical polymerization initiator.

7. The radical polymerization initiator according to any one of claims 1 to 6, a radical polymerizable compound; A composition comprising:

8. A cured product of the composition according to claim 7.

9. A method for producing a cured product, comprising a polymerization step of polymerizing radically polymerizable compounds in the composition according to claim 7 .

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