Compound, composition, cured product, and method for producing the cured product

Abstract

The object of the present invention is to provide a compound capable of forming a radical polymerization initiator having an excellent balance between sensitivity, electrical properties, and solubility.　The present invention is a compound represented by general formula (A) and a radical polymerization initiator containing said compound. In the formula, one or more of R11, R12, R13, R14, R15, R16, and R17 is a group having a hydroxyl group, and one or more of R11, R12, R13, R14, R15, R16, and R17 is an oxime-ester-containing group. R11 is preferably an oxime-ester-containing group, and at least one of R11, R12, R13, and R16 is preferably a hydroxyl-group-containing group.

Description

[Technical Field]

[0001] The present invention relates to a compound capable of forming a radical polymerization initiator excellent in sensitivity, electrical properties and solubility. [Background technology]

[0002] 2. Description of the Related Art In display devices such as liquid crystal display devices and organic EL display devices, spacers are used to maintain the distance between the upper and lower substrates of a cell.

[0003] As the spacer, a columnar spacer (hereinafter sometimes referred to as a column spacer) formed by applying a photosensitive composition to a substrate, exposing it through a predetermined mask, and then developing it is known. In recent years, a black column spacer (BCS) has been used, which integrates a column spacer and a black matrix into a single module and has light-blocking properties (Patent Document 1). However, the cured products of conventional photosensitive compositions have poor electrical properties, and when such compositions are used as spacers to form display devices, display defects may occur. In response to this, Patent Document 2 describes that the deterioration of electrical properties can be suppressed by using a compound having a hydroxyl group as a radical polymerization initiator. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2017-53942 [Patent Document 2] International Publication No. 2019 / 088055 Summary of the Invention

[0005] However, when a compound having a hydroxyl group is used as a radical polymerization initiator, its solubility in organic solvents is insufficient, which causes problems such as a long preparation time for the photosensitive composition and a decrease in dispersion stability.

[0006] The present invention has been made in view of the above problems, and a main object of the present invention is to provide a compound capable of forming a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0007] As a result of intensive investigations to solve the above problems, the present inventors have found that an oxime ester compound having an indole skeleton and a hydroxyl group can form a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility, and have completed the present invention.

[0008] That is, the present invention is a compound represented by the following general formula (A) (hereinafter, sometimes referred to as compound A).

[0009] [ka] (In the formula, R 11 , R 12 , R 14 , R 15 , R 16 and R 17 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 20 , -COR 20 , -OCOR 20 , -COOR 20 , -SR 20 , -SOR 20 , -SO2R 20 , -NR 21 R 22 , -NR 21 COR 22 , -CONR 21 R 22 , a group represented by the following general formula (1), 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 replaced by a divalent group selected from the following group I: R 13 represents a first aryl group which is 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 an unsubstituted or substituted aryl group having 7 to 30 carbon atoms in which one or more hydrogen atoms in the aromatic hydrocarbon ring are substituted with a group represented by the following general formula (1), or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group, the above heterocycle-containing group, or the above first aryl group are substituted with a divalent group selected from the following group I: R 20 , R 21 and R 22 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 20 , R 21 or R 22 When there are multiple, they may be the same or different, R 11 and R 12 , R 14 and R 15 , R 15 and R 16 and R 16 and R 17 may be bonded to form a ring, 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, the heterocycle-containing group having the above-mentioned substituent, and the first aryl group is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, or -SOH; R 11 , R 12 , R14 , R 15 , R 16 and R 17 At least one of the groups represented by the general formula (1) is a group represented by R 13 is the first aryl group, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the groups has a hydroxyl group.)

[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, -COOH, or -SOH; n represents 0 or 1; * indicates the point of attachment.)

[0011] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 30 -, -NR 30 -CO-, -CO-NR 30 -, -NR 30 -COO-, -OCO-NR 30 -or-SiR 30 R 31 -. R 30 and R 31 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 30 or R 31 When there are multiple, they may be the same or different.

[0012] In the present invention, R 11 is preferably a group represented by the above general formula (1), because the compound A can form a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0013] In the present invention, the group having a hydroxyl group is R 11 , R 12 and R 13 It is preferable that the compound A is at least one of the above, because the compound A can form a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0014] In the present invention, R 11 is a group represented by the above general formula (1), and R 11 is a group having a hydroxyl group, and R 1 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group or the aromatic hydrocarbon ring-containing group are substituted with a divalent group selected from Group I above, and R 2 is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 13is 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 of the aromatic hydrocarbon ring-containing group are substituted with a divalent group selected from Group I. This is because Compound A can form a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0015] In the present invention, R 11 is a group represented by the above general formula (1), and R 12 is a group having a hydroxyl group, and R 1 and R 2 are each independently an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 12 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from Group I above, and R 13 is preferably an aromatic hydrocarbon ring-containing group having a substituent 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 Compound A can form a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0016] In the present invention, R 11 is a group represented by the above general formula (1), and R 13 is a group having a hydroxyl group, and R 1 and R 2 are each independently an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 13is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a heterocycle-containing group having 2 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon ring-containing group, or heterocycle-containing group have been replaced with a divalent group selected from Group I. This is because Compound A can form a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0017] In the present invention, the bonding position of the hydroxyl group in the hydroxyl group-containing group is preferably the terminal of the hydroxyl group-containing group, because this enables compound A to form a radical polymerization initiator with an excellent balance of sensitivity, electrical properties, and solubility.

[0018] The present invention is a radical polymerization initiator containing the compound A. By including the compound A, the radical polymerization initiator of the present invention has an excellent balance of sensitivity, electrical properties, and solubility.

[0019] The present invention is a composition containing the above-mentioned compound A and a radically polymerizable compound. The composition of the present invention contains the compound A and a radically polymerizable compound, and therefore has excellent dispersion stability, requires a short preparation time, and can easily form a cured product with excellent electrical properties.

[0020] The present invention relates to a cured product of the above composition. The cured product of the present invention has excellent electrical properties because it uses the above composition.

[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 excellent electrical properties can be easily obtained. DETAILED DESCRIPTION OF THE INVENTION

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

[0023] A. Compound First, the compound of the present invention will be described. The compound of the present invention is a compound (compound A) represented by the following general formula (A).

[0024] [ka] (In the formula, R 11 , R 12 , R 14 , R 15 , R 16 and R 17 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, -OR 20 , -COR 20 , -OCOR 20 , -COOR 20 , -SR 20 , -SOR 20 , -SO2R 20 , -NR 21 R 22 , -NR 21 COR 22 , -CONR 21 R 22 , a group represented by the following general formula (1), 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 replaced by a divalent group selected from the following group I: R 13represents a first aryl group which is 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 an unsubstituted or substituted aryl group having 7 to 30 carbon atoms in which one or more hydrogen atoms in the aromatic hydrocarbon ring are substituted with a group represented by the following general formula (1), or a group in which one or more methylene groups in the above aliphatic hydrocarbon group, the above aromatic hydrocarbon ring-containing group, the above heterocycle-containing group, or the above first aryl group are substituted with a divalent group selected from the following group I: R 20 , R 21 and R 22 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 20 , R 21 or R 22 When there are multiple, they may be the same or different, R 11 and R 12 , R 14 and R 15 , R 15 and R 16 and R 16 and R 17 may be bonded to form a ring, 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, the heterocycle-containing group having the above-mentioned substituent, and the first aryl group is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, or -SOH; R 11 , R 12 , R 14 , R 15 , R16 and R 17 At least one of the groups represented by the general formula (1) is a group represented by R 13 is the first aryl group, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the groups has a hydroxyl group.)

[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 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, -COOH, or -SOH; n represents 0 or 1; * indicates the point of attachment.)

[0026] Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR 30 -, -NR 30 -CO-, -CO-NR 30 -, -NR 30 -COO-, -OCO-NR 30 -or-SiR 30 R 31 -. R 30 and R 31 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 30 or R 31 When there are multiple, they may be the same or different.

[0027] The compound A has an indole ring and a hydroxyl group, and therefore can form a radical polymerization initiator that has an excellent balance of sensitivity, electrical properties, and solubility. Here, excellent sensitivity means that the photosensitive composition has excellent curing properties, and that the photosensitive composition can be sufficiently cured even with a small amount of exposure. "Excellent electrical properties" means that the photosensitive composition has little effect on the electrical properties of a member adjacent to the cured product thereof. For example, when the adjacent member is a liquid crystal composition containing a liquid crystal material, this means that there is little decrease in the voltage holding ratio (VHR) of the liquid crystal composition. "Excellent solubility" means excellent solubility in organic solvents.

[0028] The reason why the compound A having the above structure and the like exhibits the above-mentioned effects is presumed to be as follows.

[0029] The compound A has the above structure and thus absorbs light having wavelengths shorter than visible light, for example, light having a wavelength of 400 nm or shorter, including the i-line (365 nm), but its light absorption efficiency is relatively low. For example, the structure of the compound A tends to have a higher transmittance of light having wavelengths shorter than visible light, compared to a structure having a carbazole ring, an oxime ester group, and a hydroxyl group-containing group. Therefore, when a coating film of a photosensitive composition containing the compound A is exposed to light, the compound A present on the opposite side of the coating film from the exposed surface can also easily absorb the exposure light. In other words, when the compound A is used, radicals can be efficiently generated even at a deep location in the thickness direction of the coating film. For these reasons, the compound A has excellent sensitivity.

[0030] Furthermore, since the compound A has a hydroxyl group in addition to the indole ring and the oxime ester group, the decomposition product also has a hydroxyl group. Furthermore, since the decomposition product has a hydroxyl group, it has low affinity with liquid crystal materials, which generally exhibit hydrophobicity. For example, even when the cured product is used as a spacer in a liquid crystal layer, migration into the liquid crystal layer, which causes a decrease in the voltage holding ratio of the liquid crystal composition, is suppressed. Therefore, the compound A has excellent electrical properties.

[0031] Furthermore, the compound A has an indole ring having a structure in which two rings are fused as the aromatic ring to which the oxime ester group represented by general formula (1) is bonded. This indole ring has two aromatic rings and is less planar. Therefore, compared with a compound having a carbazole ring, for example, the intermolecular force between the aromatic rings of the compound A is weaker, and the compound A exhibits less aggregation. As a result, the compound A exhibits excellent solubility in organic solvents. Furthermore, the reduced aggregation results in excellent light absorption efficiency during exposure. As described above, compound A has the above structure, and is therefore a compound capable of forming a radical polymerization initiator excellent in sensitivity, electrical properties, and solubility.

[0032] The above compound A will be described in detail below. In the above compound A, R 11 , R 12 , R 14 , R 15 , R 16 and R 17 at least one of the groups represented by the general formula (1) above or 13 is the first aryl group. In the above compound A, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the groups has a hydroxyl group.

[0033] 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.

[0034] 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, -COOH, or -SOH.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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 unsubstituted aromatic hydrocarbon ring-containing groups include aryl groups having 6 to 20 carbon atoms and arylalkyl groups having 7 to 20 carbon atoms. Examples of the substituted aromatic hydrocarbon ring-containing groups include groups in which one or more hydrogen atoms in the unsubstituted aromatic hydrocarbon ring-containing 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, -COOH, or -SOH.

[0040] 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. Examples of the linking group linking two aromatic hydrocarbon rings include a single bond, a sulfide group (-S-), and a carbonyl group. Examples of the aryl group having a monocyclic structure include phenyl, tolyl, xylyl, ethylphenyl, and 2,4,6-trimethylphenyl. Examples of the aryl group having a fused ring structure include naphthyl, anthracenyl, phenanthryl, and pyrenyl. Examples of the aryl group having two monocyclic aromatic hydrocarbon rings linked together include biphenyl, diphenyl sulfide, and benzoylphenyl.

[0041] 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.

[0042] 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. Furthermore, the "2 to 20 carbon atoms" in the heterocyclic ring-containing group having 2 to 20 carbon atoms refers to the total number of carbon atoms in the heterocyclic ring-containing group.

[0043] 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 substituted heterocycle-containing group include groups in which one or more hydrogen atoms in the unsubstituted heterocycle-containing group are 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, -COOH, or -SOH.

[0044] 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.

[0045] The first aryl group in the above general formula (A) is an unsubstituted or substituted aryl group having 7 to 30 carbon atoms, in which one or more hydrogen atoms in the aromatic hydrocarbon ring are substituted with a group represented by the above general formula (1). Here, the substituted aryl group in which one or more hydrogen atoms in the aromatic hydrocarbon ring are substituted with a group represented by the general formula (1) above refers to an aryl group in which one or more hydrogen atoms in the aromatic hydrocarbon ring are substituted with a group represented by the general formula (1) above, i.e., a group in which one or more hydrogen atoms in the aromatic hydrocarbon ring are substituted with a group represented by the general formula (1) above, and one or more other hydrogen atoms are further substituted with a substituent other than the group represented by the general formula (1). Examples of the substituent in the first aryl group other than the group represented by general formula (1) include a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, -COOH, or -SO2H. More specifically, such a first aryl group includes a group in which one hydrogen atom in a monocyclic aryl group such as phenyl or tolyl is substituted with a group represented by the above general formula (1).

[0046] In the general formula (A), the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group, the heterocyclic ring-containing group, or the first aryl 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. The same applies to the aliphatic hydrocarbon group, the aromatic hydrocarbon ring-containing group, or the heterocyclic ring-containing group in the general formula (1) in which one or more methylene groups have been replaced with a divalent group selected from Group I.

[0047] In the present invention, when a hydrogen atom in the 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, when a hydrogen atom in the alkyl group having 1 to 20 carbon atoms is substituted, 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 in the alkyl group is replaced with the divalent group, not the number of carbon atoms before the replacement.

[0048] In the above general formula (A), R 11 and R 12 , R 14 and R 15 , R 15 and R 16 and R 16 and R 17 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.

[0049] In the above compound A, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the groups has a hydroxyl group. The above-mentioned group having a hydroxyl group includes a hydroxyl group and a group having a hydroxyl group as a substituent (hereinafter, sometimes referred to as a "substituted hydroxyl group-containing group").

[0050] R 11 , R 12 , R 14 , R 15 , R 16 and R 17 When R is a hydroxyl group, 11 , R 12 , R 14, R 15 , R 16 and R 17 -OR 20 and R 20 is a hydrogen atom.

[0051] R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 When R is a substituted hydroxyl group-containing group, 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 is an aliphatic hydrocarbon group having a substituent of 1 to 20 carbon atoms, an aromatic hydrocarbon ring-containing group having a substituent of 6 to 20 carbon atoms, or a heterocycle-containing group having a substituent of 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 Group I above, and contains a hydroxyl group as a substituent substituting one or more hydrogen atoms in the aliphatic hydrocarbon group having a substituent, the aromatic hydrocarbon ring-containing group having a substituent, or the heterocycle-containing group having a substituent, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 But, -OR 20 , -COR 20 , -OCOR 20 , -COOR 20 , -SR 20 , -SOR 20 , -SO2R 20 , -NR 21 R 22 , -NR 21 COR 22 , -CONR 21 R 22 or a group represented by the above general formula (1), R 20 , R21 , R 22 , R 1 and R 2 is an aliphatic hydrocarbon group having a substituent of 1 to 20 carbon atoms, an aromatic hydrocarbon ring-containing group having a substituent of 6 to 20 carbon atoms, or a heterocycle-containing group having a substituent of 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 Group I above, and which contains a hydroxyl group as a substituent substituting one or more hydrogen atoms in the substituted aliphatic hydrocarbon group, the substituted aromatic hydrocarbon ring-containing group, or the substituted heterocycle-containing group.

[0052] The number of groups having a hydroxyl group, i.e., R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 The number of groups having a hydroxyl group may be from 1 to 7, and can be appropriately set depending on the application of the compound A, the required electrical properties, ease of synthesis, and the like. The number of groups having a hydroxyl group is preferably from 1 to 5, more preferably from 1 to 3, even more preferably from 1 to 2, and particularly preferably 1. This is because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0053] In the above general formula (A), R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the groups has a hydroxyl group. R 11 , R 12 , R 13 and R 16 At least one of R is preferably a group having a hydroxyl group,11 , R 12 and R 13 It is more preferable that at least one of R is a group having a hydroxyl group, and particularly R 11 and R 13 It is preferable that at least one of the groups is a group having a hydroxyl group, because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0054] The number of hydroxyl groups contained in the group having one hydroxyl group may be any number that provides desired sensitivity, electrical properties, and solubility, but is preferably from 1 to 10, more preferably from 1 to 5, and particularly preferably from 1 to 2. This is because compound A can be more easily made into a radical polymerization initiator that has an excellent balance of sensitivity, electrical properties, and solubility.

[0055] The type of hydroxyl group contained in the hydroxyl group-containing group may be any as long as it provides the desired sensitivity, electrical properties, and solubility, but is preferably an alcoholic hydroxyl group bonded to a carbon atom of a chain hydrocarbon, or a phenolic hydroxyl group bonded directly to a carbon atom of an aromatic hydrocarbon ring, and more preferably an alcoholic hydroxyl group, because this makes it easier to make the compound A into a radical polymerization initiator with an excellent balance of sensitivity, electrical properties, and solubility.

[0056] When the group having a hydroxyl group is a substituted hydroxyl group-containing group, the bonding position of the hydroxyl group is preferably the terminal of the substituted hydroxyl group-containing group, because this makes it easier to make the compound A into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. The bonding position of the hydroxyl group at the terminal of the substituted hydroxyl group-containing group means that the hydroxyl group is bonded to the position farthest from the indole ring. The position farthest from the indole ring is the position where the number of atoms between the indole ring and the atom to which the hydroxyl group is bonded is the greatest. The number of atoms between the indole ring and the atom to which the hydroxyl group is bonded refers to the minimum number of atoms connecting them, and for example, the compound represented by formula (2-1) described in the examples below has one atom, the compound represented by formula (3-2) has three atoms, and the compound represented by formula (3-9) has four atoms.

[0057] The number of hydroxyl groups in the compound A may be 1 or more, but is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 2, and particularly preferably 1. This is because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0058] In the above compound A, R 11 , R 12 , R 14 , R 15 , R 16 and R 17 at least one of the groups represented by the general formula (1) above or 13 is the first aryl group. That is, in the above compound A, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the above is a group represented by the general formula (1) or a group having a group represented by the general formula (1) (hereinafter, these groups may be collectively referred to as an oxime ester-containing group).

[0059] The number of the oxime ester-containing groups in the compound A may be from 1 to 7, and can be appropriately set depending on the application of the compound A, the required electrical properties, ease of synthesis, and the like. The number of the oxime ester-containing groups is preferably from 1 to 5, more preferably from 1 to 3, even more preferably from 1 to 2, and particularly preferably 1. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0060] In the above general formula (A), R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the groups is an oxime ester-containing group. R 11 and R 13 Preferably, at least one of R is an oxime ester-containing group, and at least R 11 is preferably an oxime ester-containing group, and particularly R 11 Preferably, only the oxime ester-containing group is present, because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. In addition, R 13 is an oxime ester-containing group, R 13 is a first aryl group.

[0061] The compound A may be R 11 is a group represented by general formula (1), and R 11 , R 12 , R 13 and R 16 Preferably, one or more of R 11 is a group represented by general formula (1), and R 11 , R 12 , R 13 and R 16 It is more preferable that only one of R 11 is a group represented by general formula (1), and R 11 Compounds in which only R has a hydroxyl group 11 is a group represented by general formula (1), and R 12 Compounds in which only R has a hydroxyl group 11 is a group represented by general formula (1), and R 13 Compounds in which only R has a hydroxyl group, and 11 is a group represented by general formula (1), and R16 More preferred are compounds in which only R has a hydroxyl group. 11 is a group represented by general formula (1), and R 11 Compounds in which only R has a hydroxyl group 11 is a group represented by general formula (1), and R 12 Compounds in which only R has a hydroxyl group, and 11 is a group represented by general formula (1), and R 13 Compounds in which only R has a hydroxyl group are preferred, and particularly compounds in which R 11 is a group represented by general formula (1), and R 11 Compounds in which only R has a hydroxyl group, and 11 is a group represented by general formula (1), and R 13 A compound in which only R has a hydroxyl group is preferred, 11 is a group represented by general formula (1), and R 11 A compound in which only one of the groups has a hydroxyl group is most preferred, because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0062] When the group represented by the general formula (1) is a group other than a group having a hydroxyl group, R 1 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, 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, and particularly preferably an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0063] When the group represented by the general formula (1) is a group other than a group having a hydroxyl group, R 1The unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) 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 compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0064] When the group represented by the general formula (1) is a group other than a group having a hydroxyl group, R 2 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, still 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 compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0065] When the group represented by the general formula (1) is a group other than a group having a hydroxyl group, R 1 and R 2 The combination of is preferably each independently an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. In addition, R 1 and R 2 When the group represented by the general formula (1) is a group other than a group having a hydroxyl group, R 1 and R 2 The preferred groups are the same as those described above.

[0066] When the group represented by the general formula (1) is a group having a hydroxyl group, R 1 and R 2 At least one of R is a group having a hydroxyl group. 1is preferably a group having a hydroxyl group, because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0067] R 1 is a group having a hydroxyl group, R 1 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group or the aromatic hydrocarbon ring-containing group have been replaced with a divalent group selected from Group I above. 1 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent have been substituted with a divalent group selected from Group I. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. In addition, R 1 is a group having a hydroxyl group as a substituent, the "group having a hydroxyl group as a substituent" may have a group other than a hydroxyl group as a substituent, but preferably has no group other than a hydroxyl group as a substituent, because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0068] R 1 is a group having a hydroxyl group, the "aliphatic hydrocarbon group" in the aliphatic hydrocarbon group having a substituent having 1 to 20 carbon atoms 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 or branched alkyl group having 3 to 7 carbon atoms. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0069] R 1 is a group having a hydroxyl group, the "aromatic hydrocarbon ring-containing group" in the aromatic hydrocarbon ring-containing group having a substituent of 6 to 20 carbon atoms is preferably an aryl group having a monocyclic structure or a structure in which aromatic hydrocarbon rings are linked, more preferably an aryl group having a monocyclic structure of 6 to 15 carbon atoms and an aryl group having a structure in which aromatic hydrocarbon rings are linked and having 12 to 18 carbon atoms, and particularly preferably an aryl group having a monocyclic structure of 8 to 12 carbon atoms and an aryl group having a structure in which aromatic hydrocarbon rings are linked. This is because compound A can be easily made into a radical polymerization initiator with an excellent balance of sensitivity, electrical properties, and solubility. The linking group linking the aromatic hydrocarbon rings used in the aryl group having 6 to 20 carbon atoms having a structure in which aromatic hydrocarbon rings are linked is preferably a sulfide group or a carbonyl group, more preferably a sulfide group, because this makes it easier to make the compound A into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0070] R 1 is a group having a hydroxyl group, the divalent group selected from Group I substituting the methylene group in the group in which one or more methylene groups in an aromatic hydrocarbon ring-containing group having a substituent of 6 to 20 carbon atoms are replaced with a divalent group selected from Group I above is preferably -O-, -COO-, -OCO-, -CO-, or -S-, more preferably -O- or -S-, and particularly preferably -O-. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0071] When the group represented by the general formula (1) is a group having a hydroxyl group, R 2 The preferred structure is the same as that when the group represented by the above general formula (1) is a group other than a group having a hydroxyl group.

[0072] In the group represented by general formula (1), n ​​is preferably 0 or 1. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0073] As described above, in the compound A, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of R is a group having a hydroxyl group. 11 , R 12 , R 13 and R 16 It is preferable that at least one of the groups is a group having a hydroxyl group, because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0074] R 11 is a group having a hydroxyl group, R 11 is preferably a group represented by the above general formula (1). In this case, the preferred structure is the same as that given as the preferred structure when the group represented by the above general formula (1) is a group having a hydroxyl group. That is, in the present invention, R 11 is a group represented by general formula (1), and R 1 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group or the aromatic hydrocarbon ring-containing group have been substituted with a divalent group selected from Group I. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0075] R 11 is a group other than a group having a hydroxyl group, R 11is preferably a group represented by the above general formula (1). In this case, the preferred structure is the same as that exemplified as the preferred structure when the group represented by the above general formula (1) is a group other than a group having a hydroxyl group. This is because the above compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0076] R 12 is a group having a hydroxyl group, R 12 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group or the aromatic hydrocarbon ring-containing group have been replaced with a divalent group selected from Group I above. 12 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent have been substituted with a divalent group selected from the above group I. This is because the above compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. In addition, R 12 is a group having a hydroxyl group as a substituent, the "group having a hydroxyl group as a substituent" may have a group other than a hydroxyl group as a substituent, but preferably has no group other than a hydroxyl group as a substituent, because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0077] R 12is a group having a hydroxyl group, the "aliphatic hydrocarbon group" in the aliphatic hydrocarbon group having a hydroxyl group as a substituent of 1 to 20 carbon atoms is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, still more preferably a linear or branched alkyl group having 1 to 8 carbon atoms, and particularly preferably a linear or branched alkyl group having 1 to 5 carbon atoms. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0078] R 12 is a group having a hydroxyl group, in which one or more methylene groups in an aliphatic hydrocarbon group having 1 to 20 carbon atoms and a hydroxyl group as a substituent are replaced with a divalent group selected from Group I above, the divalent group selected from Group I above substituting the methylene group is preferably -O-, -COO-, -OCO-, -CO-, or -S-, and particularly preferably -O- or -COO-. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0079] R 12 is a group other than a group having a hydroxyl group, R 12 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. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0080] R 13 is a group having a hydroxyl group, R 13is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a heterocyclic ring-containing group having 2 to 20 carbon atoms and having a hydroxyl group as a substituent, 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 Group I below. 13 is preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms and having a hydroxyl group as a substituent, an aromatic hydrocarbon ring-containing group having 6 to 12 carbon atoms and having a hydroxyl group as a substituent, a heterocyclic ring-containing group having 2 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aromatic hydrocarbon ring-containing group or the heterocyclic ring-containing group have been replaced with a divalent group selected from Group I. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0081] R 13 is a group having a hydroxyl group, the "aliphatic hydrocarbon group" in the aliphatic hydrocarbon group having a hydroxyl group as a substituent of 1 to 20 carbon atoms is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, and particularly preferably a linear or branched alkyl group having 1 to 5 carbon atoms. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. In addition, R 13 is an aliphatic hydrocarbon group having a hydroxyl group as a substituent, the "aliphatic hydrocarbon group having a hydroxyl group as a substituent" may have a group other than a hydroxyl group as a substituent, but preferably has no group other than a hydroxyl group as a substituent, because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0082] R 13is a group having a hydroxyl group, the "aromatic hydrocarbon ring-containing group" in the aromatic hydrocarbon ring-containing group having a hydroxyl group as a substituent of 6 to 20 carbon atoms is preferably an aryl group having a monocyclic structure or a structure in which aromatic hydrocarbon rings are linked and having 6 to 20 carbon atoms, and particularly preferably an aryl group having a monocyclic structure of 6 to 15 carbon atoms or an aryl group having a structure in which aromatic hydrocarbon rings are linked and having 12 to 18 carbon atoms. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. The linking group linking the aromatic hydrocarbon rings in the aryl group having 6 to 20 carbon atoms having a structure in which the aromatic hydrocarbon rings are linked is preferably a sulfide group or a carbonyl group, more preferably a carbonyl group, because this makes it easier to make the compound A into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. In addition, R 13 is an aromatic hydrocarbon ring-containing group having a hydroxyl group as a substituent, the "aromatic hydrocarbon ring-containing group having a hydroxyl group as a substituent" may have a group other than a hydroxyl group as a substituent. In the present invention, when the "aromatic hydrocarbon ring-containing group having a hydroxyl group as a substituent" is an aryl group having a monocyclic structure and 6 to 15 carbon atoms, it preferably has a group other than a hydroxyl group as a substituent, and more preferably has a nitro group. Furthermore, when the "aromatic hydrocarbon ring-containing group having a hydroxyl group as a substituent" is an aryl group having 12 to 18 carbon atoms and a structure in which aromatic hydrocarbon rings are linked, it preferably does not have a group other than a hydroxyl group as a substituent. This is because the above compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0083] R 13is a group having a hydroxyl group, in which one or more methylene groups in an aromatic hydrocarbon ring-containing group having a hydroxyl group as a substituent of 6 to 20 carbon atoms are replaced with a divalent group selected from Group I above, the divalent group selected from Group I above substituting the methylene group is preferably -O-, -COO-, -OCO-, -CO-, or -S-, and particularly preferably -O- or -CO-. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0084] R 13 is a group having a hydroxyl group, the "heterocycle" in the heterocycle-containing group having a hydroxyl group as a substituent having 2 to 20 carbon atoms is preferably a thienyl group, a furyl group, a pyrrole group, or an imidazole group, and particularly preferably a thienyl group. This is because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. The number of carbon atoms in the heterocycle-containing group having a hydroxyl group as a substituent having 2 to 20 carbon atoms is preferably 3 to 10, and more preferably 4 to 8. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0085] R 13 is a group having a hydroxyl group, in which one or more methylene groups in a heterocycle-containing group having a hydroxyl group as a substituent of 2 to 20 carbon atoms are replaced with a divalent group selected from Group I above, the divalent group selected from Group I above substituting the methylene group is preferably -O-, -COO-, -OCO-, -CO- or -S-, particularly preferably -O-. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties and solubility.

[0086] R 13 is a group other than a group having a hydroxyl group, R 13is preferably an unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms, a first aryl group, or a group in which one or more methylene groups in the aromatic hydrocarbon ring-containing group or the first aryl group have been replaced with a divalent group selected from Group I, and 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. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0087] R 13 When is a group other than a group having a hydroxyl group, the "aromatic hydrocarbon ring-containing group" in the unsubstituted or substituted aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms is preferably an aryl group having a monocyclic structure having a substituent having 6 to 15 carbon atoms or an aryl group having a structure in which unsubstituted aromatic hydrocarbon rings having 6 to 20 carbon atoms are linked, more preferably an unsubstituted aryl group having 12 to 18 carbon atoms and a structure in which aromatic hydrocarbon rings are linked, and particularly preferably an aryl group having 12 to 15 carbon atoms and a structure in which aromatic hydrocarbon rings are linked. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. The linking group linking the aromatic hydrocarbon rings in the aryl group having 6 to 20 carbon atoms having a structure in which the aromatic hydrocarbon rings are linked is preferably a sulfide group or a carbonyl group, more preferably a carbonyl group, because this makes it easier to make the compound A into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. In addition, R 13 However, the substituent of the monocyclic aryl group having a substituent of 6 to 15 carbon atoms is preferably a nitro group, because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0088] R 13is a group other than a group having a hydroxyl group, in which one or more methylene groups in an aromatic hydrocarbon ring-containing group having a substituent of 6 to 20 carbon atoms are replaced with a divalent group selected from Group I above, and the divalent group selected from Group I above substituting the methylene group is preferably -O-, -COO-, -OCO-, -CO- or -S-, particularly preferably -CO-. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties and solubility.

[0089] R 16 is a group having a hydroxyl group, R 16 represents a hydroxyl group, an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or -SR 20 The above R 20 is preferably an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group or the aromatic hydrocarbon ring-containing group have been substituted with a divalent group selected from Group I. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility. In addition, R 16 is a group having a hydroxyl group as a substituent, the "group having a hydroxyl group as a substituent" may have a group other than a hydroxyl group as a substituent, but preferably has no group other than a hydroxyl group as a substituent, because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0090] R 16is a group having a hydroxyl group, the "aliphatic hydrocarbon group" in the aliphatic hydrocarbon group having a substituent having 1 to 20 carbon atoms 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, and particularly preferably a linear or branched alkyl group having 2 to 5 carbon atoms. This is because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0091] R 16 is a group having a hydroxyl group, in which one or more methylene groups in an aliphatic hydrocarbon group having 1 to 20 carbon atoms and a hydroxyl group as a substituent are replaced with a divalent group selected from Group I above, the divalent group selected from Group I above substituting the methylene group is preferably -O-, -COO-, -OCO-, -CO- or -S-, particularly preferably -O-. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties and solubility.

[0092] R 16 is a group having a hydroxyl group, the "aromatic hydrocarbon ring-containing group" in the aromatic hydrocarbon ring-containing group having a hydroxyl group as a substituent of 6 to 20 carbon atoms is preferably an aryl group having a monocyclic structure or a structure in which aromatic hydrocarbon rings are linked and having 6 to 20 carbon atoms, more preferably an aryl group having a monocyclic structure and having 6 to 15 carbon atoms, and particularly preferably an aryl group having a monocyclic structure and having 6 to 10 carbon atoms. This is because the compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0093] R 16is a group having a hydroxyl group, in which one or more methylene groups in an aromatic hydrocarbon ring-containing group having a hydroxyl group as a substituent of 6 to 20 carbon atoms are replaced with a divalent group selected from Group I above, the divalent group selected from Group I above substituting the methylene group is preferably -O-, -COO-, -OCO-, -CO- or -S-, particularly preferably -S-. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties and solubility.

[0094] R 16 is a group other than a group having a hydroxyl group, R 16 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. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0095] R 14 , R 15 , R 17 is a group other than a group having a hydroxyl group, R 14 , R 15 , R 17 are each independently preferably a hydrogen atom, a halogen atom, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom, a halogen atom, or an unsubstituted alkyl group having 1 to 4 carbon atoms, and particularly preferably a hydrogen atom or a halogen atom. This is because compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0096] The compound A is R 11 is a group represented by the above general formula (1), and R 11 is a group having a hydroxyl group, R 1is an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group or the aromatic hydrocarbon ring-containing group are substituted with a divalent group selected from Group I above, and R 2 is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 13 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 of the aromatic hydrocarbon ring-containing group are substituted with a divalent group selected from Group I. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0097] The compound A is R 11 is a group represented by the above general formula (1), and R 12 is a group having a hydroxyl group, R 1 and R 2 are each independently an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 12 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from Group I above, and R 13 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 Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0098] The compound A is R 11 is a group represented by the above general formula (1), and R 13 is a group having a hydroxyl group, R 1 and R 2are each independently an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 13 is preferably an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a heterocyclic group having 2 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group, aromatic hydrocarbon ring-containing group, or heterocyclic group are substituted with a divalent group selected from Group I. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0099] The compound A is R 11 is a group represented by the above general formula (1), and R 16 is a group having a hydroxyl group, R 1 and R 2 are each independently an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, and 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 above, and R 16 is a hydroxyl group, an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or -SR 20 The above R 20 is preferably an aromatic hydrocarbon ring-containing group having 6 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group or the aromatic hydrocarbon ring-containing group have been substituted with a divalent group selected from Group I. This is because Compound A can be easily made into a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0100] The molecular weight of the compound A can be set depending on the application of the compound A. The molecular weight of the compound A is, for example, preferably from 250 to 2000, more preferably from 300 to 2000, and particularly preferably from 350 to 1000. This is because the compound A can be easily used as a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

[0101] The method for producing the compound A is not particularly limited as long as it can produce the compound A having the above structure, and for example, the method described in Japanese Patent No. 4223071 can be used. Specifically, the compound A can be produced by the following reaction scheme. First, an indole compound is reacted with an acid chloride in the presence of aluminum chloride to obtain an acylated compound. Next, the acylated compound is reacted with hydroxylamine hydrochloride to obtain an oxime compound. Next, the oxime compound is reacted with an acid anhydride or an acid chloride to obtain compound A.

[0102] [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 (A) above.

[0103] The above manufacturing method is 12 ~R 17 In this example, an indole compound in which at least one of R has a hydroxyl group is used, but compound A can also be produced by a method in which an indole compound without a hydroxyl group is used to obtain a compound without a hydroxyl group in a similar manner, and then an alkyl group or the like having a hydroxyl group is introduced according to a standard method. 1 Compound A can also be produced by a method in which an acylated compound is obtained by reacting an acid chloride in which the group is a group having a hydroxyl group.

[0104] The above reaction scheme shows a method for producing compound A when n in general formula (A) is 0. Compound A in which n in general formula (A) is 1 can be produced by the same method as the above-mentioned production method, except that instead of reacting an acyl compound with hydroxylamine hydrochloride to obtain an oxime compound, an acyl compound is reacted with a nitrite ester in the presence of hydrochloric acid to obtain an oxime compound.

[0105] The compound A generates radicals. The method for generating radicals from the compound A may be any method generally used for radical generators, and specific examples thereof include a method of irradiating with energy rays, a method of heat treatment, and a method of performing these methods simultaneously or sequentially.

[0106] 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 200 nm to 450 nm, and more preferably have a maximum spectrum in the wavelength range of 300 nm to 400 nm, because radicals can be effectively generated from the compound A.

[0107] 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.).

[0108] 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 2More than 2000mJ / cm 2 The following is preferred because it allows radicals to be generated effectively from the compound A.

[0109] The heating temperature in the heat treatment is, for example, preferably 70° C. or higher and 450° C. or lower, and more preferably 150° C. or higher and 300° C. or lower. The heating time in the heat treatment is, for example, preferably 1 minute or higher and 100 minutes or lower, because this allows radicals to be generated effectively from the compound A.

[0110] The compound A may be used, for example, in any application that generates radicals, such as a radical polymerization initiator that polymerizes radically polymerizable compounds together by radicals, and is particularly preferably a photoradical polymerization initiator that generates radicals upon irradiation with energy rays.

[0111] The radical polymerization initiator can be used, for example, in a curable composition containing a radically polymerizable compound.

[0112] 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 as a solder resist, a circuit-forming resist, a bump resist, or the like, for use in semiconductor packages, and as a composition for forming insulating members in electronic substrate circuits.

[0113] From the viewpoint of more effectively exhibiting the effect of an excellent balance of sensitivity, electrical properties, and solubility, the compound A is preferably used for components that come into contact with a liquid crystal material, such as an alignment layer, a spacer for a liquid crystal layer, an insulating film, an overcoat layer, a sealant that seals the periphery of a liquid crystal layer, a color filter, or a black matrix, and particularly preferably for use as a spacer for a liquid crystal layer. By using the compound A, for example, a liquid crystal layer spacer characterized by having a cured product of a composition containing the compound A, a liquid crystal display device characterized by including the liquid crystal layer spacer, etc. can be obtained. The liquid crystal layer spacers can also be used as black column spacers that also function as a black matrix.

[0114] B. Radical polymerization initiator Next, the radical polymerization initiator of the present invention will be described. The radical polymerization initiator of the present invention is characterized by containing the compound A described above.

[0115] By including the compound A, the radical polymerization initiator of the present invention has an excellent balance of, for example, sensitivity, electrical properties, and solubility.

[0116] The content of compound A in the radical polymerization initiator of the present invention may be any content that can impart the desired radical generating ability, and can be appropriately set depending on the application of the radical polymerization initiator. The content of compound A in the radical polymerization initiator can be 100 parts by mass per 100 parts by mass of the radical polymerization initiator, i.e., the radical polymerization initiator can consist solely of compound A. Alternatively, the content of compound A in the radical polymerization initiator of the present invention can be less than 100 parts by mass per 100 parts by mass of the radical polymerization initiator, i.e., the radical polymerization initiator can be a composition containing compound A and other components. In this case, the content of compound A can be, for example, more than 30 parts by mass, and preferably 50 parts by mass or more. This is because the radical polymerization initiator has an excellent balance of sensitivity, electrical properties, and solubility. In the present invention, unless otherwise specified, the contents are based on mass.

[0117] The radical polymerization initiator may contain only one type of compound A, or two or more types. The number of types may be, for example, two or more and five or less. Furthermore, the radical polymerization initiator of the present invention may contain a radical polymerization initiator other than compound A.

[0118] The above-mentioned compound A is the same as that described in the section "A. Compound."

[0119] As the other components, any component that does not inhibit the function as a radical polymerization initiator can be used, and examples thereof include the solvents described in "3. Solvent" in "C. Composition" below, and the components described in the section "4. Other Components."

[0120] 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, a method of mixing the compound A and other components using an extruder or the like and then molding the mixture into pellets can be mentioned as a production method. The radical polymerization initiator may be in the form of a solution in which the compound A is dispersed or dissolved in a solvent.

[0121] C. Composition Next, the composition of the present invention will be described. The composition of the present invention is characterized by containing the above-mentioned compound A and a radically polymerizable compound.

[0122] The composition of the present invention contains the above-mentioned compound A and a radically polymerizable compound, and therefore has excellent dispersion stability, can be prepared in a short time, and can easily form a cured product with excellent electrical properties.

[0123] 1. Compound A The content of the compound A 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 compound A in the composition of the present invention can be, for example, from 0.001 to less than 30 parts by mass, and preferably from 0.005 to 10 parts by mass, per 100 parts by mass of the solid content of the composition, because the composition can more effectively exhibit the effects of dispersion stability, a short preparation time, and the ease of forming a cured product with excellent electrical properties. The solid content includes all components other than the solvent.

[0124] The content of the compound A is preferably 0.1 to 50 parts by mass, more preferably 1 to 30 parts by mass, and particularly preferably 5 to 20 parts by mass, relative to 100 parts by mass of the radical polymerizable compound, because the composition can more effectively exhibit the effects of dispersion stability, a short preparation speed, and the ability to easily form a cured product with excellent electrical properties.

[0125] The composition may contain only one type of compound A, or two or more types of compounds A. For example, the number of types of compounds A may be two or more and five or less.

[0126] The above-mentioned compound A is the same as that described in the section "A. Compound."

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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. This is because, when the content is within the above range, the composition has excellent curability.

[0131] 3. Solvent The composition may contain a solvent in addition to the compound A and the radical polymerizable compound. The solvent is liquid at room temperature (25°C) and atmospheric pressure and is capable of dispersing or dissolving compound A, the radical polymerizable compound, and other components described below. Therefore, even if the solvent is liquid at room temperature (25°C) and atmospheric pressure, compound A and the radical polymerizable compound are not included in the solvent.

[0132] 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 compound A and the radical polymerizable compound.

[0133] 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, because the use of such a solvent makes it easy for the composition to have excellent dispersion stability.

[0134] 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.

[0135] 4.Other The composition may contain other components as needed in addition to the compound A, the radical polymerizable compound, and the 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 those described in JP 2005-234362 A as copolymers [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 additives is appropriately selected depending on the purpose of use and is not particularly limited, but for example, 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, because the composition can more effectively exhibit the effects of dispersion stability, short preparation speed, and the ease of forming a cured product with excellent electrical properties.

[0136] 5. 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. Compound" above.

[0137] D. 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.

[0138] The cured product of the present invention has excellent electrical properties because it uses the above-mentioned composition. The cured product is a cured product of the above-mentioned composition, and contains a polymer of the radically polymerizable compound contained in the composition. The above composition is the same as that described in the section "C. Composition" above.

[0139] The shape of the cured product in plan view can be appropriately set depending on the application of the cured product, and can be, for example, a pattern such as a dot shape or a line shape.

[0140] The uses of the cured product are the same as those described in the section "A. Compounds" above.

[0141] 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 "E. Production method of cured product" below.

[0142] E. 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.

[0143] 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 excellent electrical properties.

[0144] 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 compound A. The method for generating radicals from the compound A may be any method that can generate a desired amount of radicals from the compound A, 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 methods of irradiating with energy rays and methods of heat treatment include the same methods as those described in the section "A. Compound" above.

[0145] 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 compound A, and the radical polymerizable compound can be effectively cured. The composition is the same as that described in the section "C. Composition" above.

[0146] 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 compound A 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.

[0147] 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 at any time after the curing step.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 3.Other The cured product produced by the above production method and its uses are the same as those described in the section "D. Cured product" above.

[0152] 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]

[0153] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0154] [Example 1] 30 mmol of indole, 33 mmol of potassium carbonate, 33 mmol of 4-fluoronitrobenzene, and DMSO were placed in a reaction vessel under a nitrogen atmosphere and stirred at 150° C. Purification was then carried out to obtain N-nitrophenylindole. Next, 36 mmol of aluminum chloride and ethane dichloride were charged into a reaction vessel, and 30 mmol of the obtained N-nitrophenylindole and then 36 mmol of 4-fluoro-O-toluic acid chloride were charged and stirred. Then, purification was carried out to obtain an acylated product. Next, ethylene glycol, 20 mmol of the obtained acylated compound, and 40 mmol of potassium carbonate were charged into a reaction vessel and reacted at 100° C. Then, purification was carried out to obtain an acylated compound having a hydroxy group. Next, 20 mmol of the obtained acyl compound having a hydroxy group, 40 mmol of hydroxylamine hydrochloride, and 25.0 g of pyridine were charged into a reaction vessel and stirred at 100° C. Then, purification was carried out to obtain an oxime compound. Next, 10 mmol of the obtained oxime compound and dimethylformamide were charged into a reaction vessel, and 11 mmol of triethylamine and 11 mmol of acetyl chloride were added dropwise thereto, followed by stirring. Purification was then carried out to obtain a compound represented by the following formula (1-1). The compound obtained is the target compound. 1 The product was confirmed by H-NMR and mass spectrometry (MARDI-TOF-MS). MS[M+1] + m / z:474

[0155] [Example 2] A compound represented by the following formula (1-2) was obtained in the same manner as in Example 1, except that 4-(chloromethyl)benzoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:474

[0156] [Example 3] An acylated product was obtained in the same manner as in Example 1, except that 4-fluorobenzophenone was used instead of 4-nitrofluorobenzene and 4-chlorobutyryl chloride was used instead of 4-fluoro-O-toluic acid chloride. Next, 120 mmol of sodium formate, 1.5 mmol of tetrabutylammonium bromide, and dimethylformamide were charged into a reaction vessel and stirred at 100° C. Then, purification was carried out to obtain an acylated product having a hydroxy group. Next, the resulting acyl derivative having a hydroxy group was used to obtain a compound represented by the following formula (1-3) in the same manner as in Example 1. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:441

[0157] [Example 4] 20 mmol of the acyl compound obtained in Example 3 and dimethylformamide in an amount three times the theoretical yield were charged into a reaction vessel, and while stirring at 5°C under a nitrogen atmosphere, 20 mmol of 35% hydrochloric acid and 30 mmol of isobutyl nitrite were slowly added dropwise and stirred. Purification was then carried out to obtain an oxime compound. Next, using the obtained oxime compound, a compound represented by the following formula (1-4) was obtained in the same manner as in Example 1. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:455

[0158] [Example 5] A compound represented by the following formula (1-5) was obtained in the same manner as in Example 1, except that fluorobenzene was used instead of 4-nitrofluorobenzene and mercaptoethanol was used instead of diethylene glycol. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] +m / z:445

[0159] [Example 6] A compound represented by the following formula (1-6) was obtained in the same manner as in Example 1, except that fluorobenzene was used instead of 4-nitrofluorobenzene and 4-hydroxythiophenol was used instead of diethylene glycol. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:493

[0160] [Example 7] An acylated product was obtained in the same manner as in Example 1, except that indole-2-carboxylic acid was used instead of indole and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Next, the obtained acylated product was used in the same manner as in Example 4 to obtain a compound represented by the following formula (2-1). The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:466

[0161] [Example 8] 20 mmol of indole-2-methanol, ethylene glycol, and 1 ml of concentrated sulfuric acid were charged into a reaction vessel and stirred at 120° C. Purification was then carried out to obtain 2-(propoxymethyl)indole. Next, an acylated product was obtained in the same manner as in Example 1, except that octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride, and then a compound represented by the following formula (2-2) was obtained in the same manner as in Example 4. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:510

[0162] [Example 9] The compound represented by the following formula (2-3) was obtained in the same manner as in Example 8, except that indole-2-carboxylic acid was used instead of indole-2-methanol. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:524

[0163] [Example 10] An acylated product was obtained in the same manner as in Example 1, except that 3-bromo-1-propanol was used instead of 4-fluoronitrobenzene and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, a compound represented by the following formula (3-1) was obtained in the same manner as in Example 4. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:373

[0164] [Example 11] The compound represented by the following formula (3-2) was obtained in the same manner as in Example 10, except that 5-fluoro-2-nitrophenol was used instead of 3-bromo-1-propanol. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:452

[0165] [Example 12] The compound represented by the following formula (3-3) was obtained in the same manner as in Example 8, except that N-(3-hydroxy-4-nitrophenyl)indole obtained in Example 11 was used instead of indole-2-methanol. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:496

[0166] [Example 13] The acylated product was obtained in the same manner as in Example 1, except that 2-(4-fluorophenyl)ethanol was used instead of 4-fluoronitrobenzene and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, the compound represented by the following formula (3-4) was obtained in the same manner as in Example 4. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:435

[0167] [Example 14] The acylated product was obtained in the same manner as in Example 1, except that 2-(4-chlorophenyl)-2-methylpropanol was used instead of 4-fluoronitrobenzene and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, the compound represented by the following formula (3-5) was obtained in the same manner as in Example 4. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:463

[0168] [Example 15] The acylated product was obtained in the same manner as in Example 1, except that 2-methylindole was used instead of indole, 4-chlorophenoxyethanol was used instead of 4-fluoronitrobenzene, and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, the compound represented by the following formula (3-6) was obtained in the same manner as in Example 4. MS[M+1] + m / z:465

[0169] [Example 16] The acylated product was obtained in the same manner as in Example 1, except that 4-chlorophenoxy-2-propanol was used instead of 4-fluoronitrobenzene and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, the compound represented by the following formula (3-7) was obtained in the same manner as in Example 4. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:465

[0170] [Example 17] The acylated product was obtained in the same manner as in Example 1, except that 4-fluoro-4'-hydroxybenzophenone was used instead of 4-fluoronitrobenzene and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. The compound represented by the following formula (3-8) was then obtained in the same manner as in Examples 4 and 8. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:555

[0171] [Example 18] The acylated product was obtained in the same manner as in Example 1, except that 5-bromo-2-thiophenemethanol was used instead of 4-fluoronitrobenzene and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, the compound represented by the following formula (3-9) was obtained in the same manner as in Example 4. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:427

[0172] [Example 19] An acylated product was obtained in the same manner as in Example 1, except that 2,5-dibromothiophene was used instead of 4-fluoronitrobenzene and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, a compound represented by the following formula (3-10) was obtained in the same manner as in Examples 4 and 8. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:457

[0173] [Example 20] The acylated product was obtained in the same manner as in Example 1, except that 5-hydroxyindole was used instead of indole and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, the compound represented by the following formula (4-1) was obtained in the same manner as in Example 4. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:382

[0174] [Example 21] An acyl compound having a hydroxyl group was obtained in the same manner as in Example 1, except that 5-hydroxyindole was used instead of indole and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, a compound represented by the following formula (4-2) was obtained in the same manner as in Examples 4 and 8. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:426

[0175] [Example 22] The acylated compound was obtained in the same manner as in Examples 1 and 6, except that 5-fluoroindole was used instead of indole and octanoyl chloride was used instead of 4-fluoro-O-toluic acid chloride. Then, the compound represented by the following formula (4-3) was obtained in the same manner as in Example 4. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:490

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[0180] [Example 23] A compound represented by the following formula (1-7) was obtained in the same manner as in Example 1, except that propionyl chloride was used instead of acetyl chloride. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:488

[0181] [Example 24] A compound represented by the following formula (1-8) was obtained in the same manner as in Example 1, except that propylene glycol was used instead of ethylene glycol. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:488

[0182] [Example 25] A compound represented by the following formula (1-9) was obtained in the same manner as in Example 1, except that 6-methylindole was used instead of indole. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:488

[0183] [Example 26] A compound represented by the following formula (1-10) was obtained in the same manner as in Example 1, except that 5-methylindole was used instead of indole. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:488

[0184] [Example 27] A compound represented by the following formula (1-11) was obtained in the same manner as in Example 1, except that 5-fluoroindole was used instead of indole. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:492

[0185] [Example 28] A compound represented by the following formula (1-12) was obtained in the same manner as in Example 1, except that 5-cyanoindole was used instead of indole. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:499

[0186] [Example 29] A compound represented by the following formula (1-13) was obtained in the same manner as in Example 1, except that 5-dimethylaminoindole was used instead of indole. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:517

[0187] [Example 30] A compound represented by the following formula (1-14) was obtained in the same manner as in Example 3, except that benzoyl chloride was used instead of acetyl chloride. The compound obtained is the target compound. 1The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:503

[0188] [Example 31] A compound represented by the following formula (1-15) was obtained in the same manner as in Example 3, except that 1,4-difluorobenzene was used instead of 4-chlorobenzophenone. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:355

[0189] [Example 32] A compound represented by the following formula (1-16) was obtained in the same manner as in Example 3, except that 5-fluoro-2-nitrotoluene was used instead of 4-chlorobenzophenone. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:396

[0190] [Example 33] A compound represented by the following formula (1-17) was obtained in the same manner as in Example 3, except that 5-fluoro-2-nitroanisole was used instead of 4-chlorobenzophenone. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:412

[0191] [Example 34] A compound represented by the following formula (1-18) was obtained in the same manner as in Example 3, except that 5-nitroindole was used instead of indole. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:486

[0192] [Example 35] A compound represented by the following formula (1-19) was obtained in the same manner as in Example 3, except that 5-methoxyindole was used instead of indole. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:471

[0193] [Example 36] A compound represented by the following formula (2-4) was obtained in the same manner as in Example 1, except that 2-(4-fluorophenyl)indole was used instead of indole. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:474

[0194] [Example 37] The compound represented by the following formula (3-11) was obtained in the same manner as in Example 16, except that 3-cyclohexylpropanoyl chloride was used instead of octanoyl chloride. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:477

[0195] [Example 38] The compound represented by the following formula (3-12) was obtained in the same manner as in Example 16, except that phenylacetyl chloride was used instead of octanoyl chloride. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:457

[0196] [Example 39] The compound represented by the following formula (3-13) was obtained in the same manner as in Example 16, except that 2-thienylacetyl chloride was used instead of octanoyl chloride. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:463

[0197] [Example 40] The compound represented by the following formula (3-14) was obtained in the same manner as in Example 16, except that ethyl glutaryl chloride was used instead of octanoyl chloride. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry. MS[M+1] + m / z:453

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[0202] [Production Example 1] Preparation of Polymer B-1 Having Hydrophilic Groups 184 g of 1,1-bis[4-(2,3-epoxypropyloxy)phenyl]indane, 58 g of acrylic acid, 0.26 g of 2,6-di-tert-butyl-p-cresol, 0.11 g of tetra-n-butylammonium bromide, and 105 g of PGMEA were placed in a reaction vessel and stirred for 16 hours at 120° C. The reaction solution was cooled to room temperature, and 160 g of PGMEA, 59 g of biphthalic anhydride, and 0.24 g of tetra-n-butylammonium bromide were added, followed by stirring at 120° C. for 4 hours. Further, 20 g of tetrahydrophthalic anhydride was added, and the mixture was stirred at 120°C for 4 hours, at 100°C for 3 hours, at 80°C for 4 hours, at 60°C for 6 hours, and at 40°C for 11 hours. Then, 128 g of PGMEA was added, and a polymer B-1 having a hydrophilic group was obtained as a PGMEA solution (Mw=5000, Mn=2100, acid value (solid content) 92.7 mgKOH / g, solid content 44.5% by mass).

[0203] [Production Example 2] Preparation of Carbon Black Dispersion D-1 Carbon black dispersion D-1 was prepared by mixing 15 parts by mass of MA100 (manufactured by Mitsubishi Chemical Corporation) as carbon black, 11.25 parts by mass of BYK161 (manufactured by BYK) as a dispersant (solid content concentration: 40% by mass), and 73.75 parts by mass of PGMEA as a solvent and processing the mixture in a bead mill.

[0204] [Production Example 3] Synthesis of Comparative Compound A'1 A comparative compound A'1 represented by the following formula (A'1) was obtained. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry.

[0205] [Production Example 4] Synthesis of Comparative Compound A'2 A comparative compound A'2 represented by the following formula (A'2) was obtained. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry.

[0206] [Production Example 5] Synthesis of Comparative Compound A'3 A comparative compound A'3 represented by the following formula (A'3) was obtained. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry.

[0207] [Production Example 6] Synthesis of Comparative Compound A'4 A comparative compound A'4 represented by the following formula (A'4) was obtained. The compound obtained is the target compound. 1 The results were confirmed by H-NMR and mass spectrometry.

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[0209] 1. Sensitivity The radical polymerization initiators of the following Examples and Comparative Examples were subjected to sensitivity evaluation using evaluation compositions. A composition for evaluation was prepared to have the composition shown below, and then the composition for evaluation was applied to a glass substrate (100 mm x 100 mm) using a spin coater and pre-baked at 90°C for 100 seconds. Next, using a mirror projection aligner (product name: TME-150RTO, manufactured by Topcon Corporation), the coating film was irradiated with ultraviolet light through a negative mask having a 30 μm line pattern formed thereon, with an exposure gap of 150 μm. The exposure doses were 25, 50, 75, and 100 mJ / cm 2 There are four stages: Thereafter, a developer consisting of a 0.04 mass % aqueous potassium hydroxide solution was discharged onto the substrate at 23° C., thereby performing shower development. The development time was set to 1.5 times the break time (BT), which is the time required for the unexposed area to completely dissolve. Thereafter, post-baking was carried out at 230° C. for 30 minutes. The thickness of the coating film after post-baking was 3.0 μm. The width (line width) of the pattern at 30 μm after post-baking was measured and used as an index of sensitivity characteristics for evaluation. The results are shown in Tables 2 and 3 below. <Evaluation criteria> ++: The exposure dose at which the line width becomes 30 μm or more is 25 mJ / cm 2 less than +: The exposure dose at which the line width is 30 μm or more is 25 mJ / cm 2 More than 50mJ / cm 2 less than - : The exposure dose for a line width of 30 μm or more is 50 mJ / cm 2 More than 100mJ / cm 2 less than --: The exposure dose for a line width of 30 μm or more is 100 mJ / cm 2 End It can be determined that the sensitivity is better when the exposure dose required to achieve a predetermined line width is smaller.

[0210] (Radical polymerization initiator) Examples 1 to 22: Compound A (obtained in Examples 1 to 22) Comparative Example 1: Compound represented by the above formula (A'1) (obtained in Production Example 3) Comparative Example 2: Compound represented by the above formula (A'2) (obtained in Production Example 4) Comparative Example 3: Compound represented by the above formula (A'3) (obtained in Production Example 5) Comparative Example 4: Compound represented by the above formula (A'4) (obtained in Production Example 6) Comparative Example 5: Compound represented by the above formula (A'5) (photoradical polymerization initiator, IRGACURE OXE-01 manufactured by BASF) Comparative Example 6: Compound represented by the above formula (A'6) (photoradical polymerization initiator, IRGACURE OXE-02 manufactured by BASF) Examples 23 to 40: Compound A (obtained in Examples 23 to 40)

[0211] (Method of producing the composition for evaluation) The radical polymerization initiators of the above Examples and Comparative Examples, radical polymerizable compounds, pigment dispersions, coupling agents, and solvents were mixed according to the formulations in Table 1 below to prepare compositions for evaluation. The numbers in the table represent parts by mass. The components used in the table are as follows:

[0212] (Radical polymerizable compound) B1: Polymer obtained in Production Example 1 above (radical polymerizable compound having a hydrophilic group) B2: SPC-3000 (radical polymerizable compound having a hydrophilic group; manufactured by Showa Denko K.K., solid content 42.7%, PGMEA solution) C1: Kayarad DPHA (a radical polymerizable compound (multifunctional acrylate) without hydrophilic groups; manufactured by Nippon Kayaku Co., Ltd.)

[0213] (pigment dispersion) D1: Carbon black pigment dispersion (obtained in Production Example 2 above)

[0214] (Silane coupling agents, solvents) E1: KBE-403 (silane coupling agent, manufactured by Shin-Etsu Chemical Co., Ltd.) F1: Propylene glycol-1-monomethyl ether-2-acetate (solvent)

[0215] [Table 1]

[0216] 2. Electrical characteristics The evaluation composition prepared in the same manner as in "1. Sensitivity Evaluation" was applied to a glass substrate (100 mm x 100 mm) using a spin coater, and pre-baked at 90°C for 100 seconds. Next, a proximity exposure device (product name: TME-150RAK-12, manufactured by Topcon Corporation) was used to irradiate the coating with ultraviolet light at a dose of 200 mJ / cm without using a mask. 2 Irradiated with. Thereafter, post-baking was carried out at 230° C. for 30 minutes. The thickness of the coating film after post-baking was 3.0 μm. One part by weight of the post-baked coating was mixed with 40 parts by weight of ADEKA's liquid crystal "RS-182" and stored at 120°C for 1 hour. The mixture was then removed to room temperature and allowed to stand, after which the supernatant was collected. The VHR (voltage holding ratio) of the collected liquid crystal composition was compared before and after mixing the liquid crystal with the coating, and the VHR holding ratio was calculated using the following formula and evaluated according to the following criteria. The results are shown in Tables 2 and 3 below. The evaluation was carried out by injecting the liquid crystal composition into a TN cell for liquid crystal evaluation (cell thickness 5 μm, electrode area 8 mm × 8 mm, alignment film JALS2096), and measuring the VHR using a VHR-1A (manufactured by Toyo Corporation) (measurement conditions: pulse voltage width 60 μs, frame period 16.7 ms, pulse height ±5 V, measurement temperature 60°C). VHR retention rate (%) = {(VHR of liquid crystal "RS-182" before mixing with coating film) - (VHR of liquid crystal composition obtained by mixing with coating film)} / (VHR of liquid crystal "RS-182" before mixing with coating film) × 100 <Evaluation criteria> ++:VHR retention rate over 96.0% +: VHR retention rate is 93.0% or more but less than 96.0% - : VHR retention rate is less than 93.0% It can be determined that the higher the VHR retention rate, the better the electrical properties.

[0217] 3.Solubility evaluation The solubility of the above-mentioned radical polymerization initiators in propylene glycol monomethyl ether (PGMEA) at 25°C was evaluated, and the concentration (mass%) of the radical polymerization initiator soluble in PGMEA was measured. Evaluation was then performed according to the following criteria. The results are shown in Tables 2 and 3 below. <Evaluation criteria> +: 5% by mass or more -: Less than 5% by mass The higher the soluble concentration, the better the solubility.

[0218] [Table 2]

[0219] [Table 3]

[0220] From Tables 2 and 3, it was confirmed that the compounds of the examples have an excellent balance of sensitivity, electrical properties, and solubility. From these findings, it was confirmed that the compound A is useful for components that come into contact with liquid crystal materials, such as spacers in a liquid crystal layer. [Industrial Applicability]

[0221] According to the present invention, it is possible to provide a compound capable of forming a radical polymerization initiator having an excellent balance of sensitivity, electrical properties, and solubility.

Claims

1. A compound represented by the following general formula (A): 【Chemical 1】 (In the formula, R １１ is a group represented by the following general formula (1): R １２ , R １４ , R １５ , R １６ and R １７ each independently represents a hydrogen atom or an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, at least one of R 11 and R 13 is a group having a hydroxyl group; When R 13 is a group having a hydroxyl group, R 13 represents an aryl group having a monocyclic structure and 6 to 15 carbon atoms, which has a hydroxyl group as a substituent and optionally further has a nitro group as a substituent, or an aryl group having 12 to 18 carbon atoms linked to an aromatic hydrocarbon ring; When R 13 is a group other than a group having a hydroxyl group, R 13 represents a monocyclic aryl group having 6 to 15 carbon atoms and having a nitro group as a substituent, or an unsubstituted aryl group having 12 to 18 carbon atoms and linked to an aromatic hydrocarbon ring; In the aryl group having 12 to 18 carbon atoms to which the aromatic hydrocarbon rings are linked, the linking group linking the aromatic hydrocarbon rings is a sulfide group or a carbonyl group. 【Chemistry 2】 (In the formula, R １ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group have been replaced with a divalent group selected from the following Group I: R ２ represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a group in which one or more methylene groups in the aliphatic hydrocarbon group have been 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 substituent is a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, —COOH, or —SO ２ H, n represents 0 or 1; * indicates the bonding site.) Group I: -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO ２ -, -NR ３０ -, -NR ３０ -CO-, -CO-NR ３０ -, -NR ３０ -COO-, -OCO-NR ３０ -or-SiR ３０ R ３１ -. R ３０ and R ３１ each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms; R ３０ or R ３１ When there are multiple, they may be the same or different.

2. R １１ is a group represented by the general formula (1), and R １１ is a group having a hydroxyl group, R １ is an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a hydroxyl group as a substituent, or a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from Group I, R ２ is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R １３ is a monocyclic aryl group having 6 to 15 carbon atoms and having a nitro group as a substituent, or an unsubstituted aryl group having 12 to 18 carbon atoms and an aromatic hydrocarbon ring linked thereto.

3. R １１ is a group represented by the general formula (1), and R １３ is a group having a hydroxyl group, R １ and R ２ are each independently an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R １３ is a monocyclic aryl group having 6 to 15 carbon atoms, or an aryl group having 12 to 18 carbon atoms linked to an aromatic hydrocarbon ring, which has a hydroxyl group as a substituent and a nitro group as a substituent.

4. The compound according to any one of claims 1 to 3, wherein the bonding position of the hydroxyl group in the hydroxyl group-containing group is a terminal of the hydroxyl group-containing group.

5. A radical polymerization initiator comprising the compound according to any one of claims 1 to 4.

6. A compound according to any one of claims 1 to 4, a radical polymerizable compound; A composition comprising:

7. A cured product of the composition according to claim 6.

8. A method for producing a cured product, comprising a polymerization step of polymerizing radically polymerizable compounds in the composition according to claim 6 .

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