Compound, photoacid generator, acid-reactive composition, and acid generation method

Abstract

The present invention provides: a compound represented by general formula (1); a photoacid generator and an acid-reactive composition which contain the compound; and an acid generation method using the compound.　In formula (1), Ar11 to Ar13 each represent an aromatic hydrocarbon ring group having a specific substituent; R13 represents a condensed polycyclic aromatic hydrocarbon ring group or a condensed polycyclic aromatic heterocyclic group which may have a specific substituent, a group having an aromatic ketone skeleton, or a group having a conjugated bonding group with an aromatic hydrocarbon ring group or the like; R11 and R12 each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; Z11 represents an oxygen atom or the like; m1 and p1 are each 0 or 1 (however, m1 is 0 in cases where n1 is 0); n1 is an integer of 0-4; X11 represents a boron atom or the like; and Y11 represents an organic onium cation. However, in cases where R13 is a specific group such as a condensed polycyclic aromatic heterocyclic group and the hetero atom is a bond to Z11, forms wherein m1 = n1 = 0 and forms wherein m1 = 1 are excluded.

Description

Compound, photoacid generator, acid-reactive composition, acid generation method

[0001] The present invention relates to a compound, a photoacid generator, an acid-reactive composition, and an acid generation method.

[0002] Methods for initiating and promoting various reactions with an acid catalyst have been studied and developed. For example, cationic polymerization has advantages such as little volume shrinkage and no oxygen inhibition, and is a widely used industrial curing mode. In particular, photo cationic polymerization that generates active species by irradiation with UV light (ultraviolet rays) has high storage stability of the polymerizable composition before curing and does not require a heating furnace or the like when curing, so it is highly convenient. To take advantage of these conveniences, the polymerizable composition and the photoacid generator used therein are required to have high thermal latency and high sensitivity to UV light. However, thermal latency and UV sensitivity often trade off, and it is difficult to achieve both. Also, although the UV sensitivity can be improved to some extent while maintaining the thermal latency by increasing the absorption wavelength of the counter cation forming the photoacid generator, there is a problem that the coloring of the polymer (cured product) becomes strong and the applications are limited.

[0003] Also, for cationic polymerization, it is required that the acidity of the Bronsted acid or Lewis acid, which is the active species, is high. Commonly used counter anions (active species after UV irradiation) forming the photoacid generator are PF ６ － , SbF ６ － , B(C ６ F ５ ) ４ － However, PF ６ － has a slightly low acidity, and the amount of catalyst may increase in some cases. SbF ６ － has restrictions in terms of regulations. B(C ６ F ５ ) ４ －Although it has high acidity and there are no legal regulations, the heat resistance of the cured product may be low. To overcome these drawbacks, compounds containing various counter anions are being investigated. For example, Patent Document 1 describes a compound represented by a specific formula that generates Lewis acid upon irradiation with ultraviolet light. For example, a compound having an ate complex of a carbonate, ether, or carbamate with a triarylborane or triarylarane as a counter anion is described as a general formula. Non-Patent Document 1, although relating to a cationic polymerization catalyst for isobutene rather than a photoacid generator, describes a compound having a chemical structure similar to the compound described in Patent Document 1, namely [RCO ２ H {B(C ６ F ５ ) ３} １，２ ] (where R is an alkyl or aryl group) is formally described, and [Me ４ N] [MeCO ２ {B(C ６ F ５ ) ３}] and [Me ４ N] [MeCO ２ {B(C ６ F ５ ) ３} ２ Only the following two types are specifically described.

[0004] International Publication No. 2013 / 142956

[0005] Canadian Journal of Chemistry 2006, 84, 225.

[0006] As mentioned above, various photoacid generators have been investigated, but a photoacid generator possessing both excellent thermal potential and high UV sensitivity has not yet been found. Against this backdrop, the development of a photoacid generator that combines excellent thermal potential and high UV sensitivity is desired.

[0007] The present invention aims to provide a compound possessing excellent thermal latent properties and high UV sensitivity, and a photoacid generator containing this compound. Furthermore, the present invention aims to provide an acid-reactive composition containing the above compound, and a method for generating acid using the above compound.

[0008] The inventors of this invention, contrary to the conventional development trend which has mainly focused on research and development of organic onium cations, diligently pursued research on the counter-anion moiety of photoacid generators. As a result, they found that by forming an ate complex with a carboxylate or alkoxide of a specific structure into which a photosensitizer that promotes the photoreaction is introduced, and a group 13 element with three aromatic hydrocarbon ring groups substituted, and by latently incorporating the anion of the group 13 element with three aromatic hydrocarbon ring groups substituted within this ate complex, it is possible to achieve both excellent thermal latent properties and high UV sensitivity. This invention was completed after further research based on this finding.

[0009] In other words, the above problems of the present invention are solved by the following means: <1> A compound represented by the following general formula (1). In general formula (1), Ar １１ ~Ar １３ Each independently represents an aromatic hydrocarbon ring group having at least one halogen group and one C1-C4 alkyl group containing a fluorine atom as substituents, R １３ R represents a condensed polycyclic aromatic hydrocarbon ring group or a condensed polycyclic aromatic heterocyclic ring group having at least one substituent selected from a benzyl group, an alkoxy group, a C1-C20 alkyl group which may have a branched or cyclic structure, an aliphatic heterocyclic group, a halogeno group, a hydroxyl group, a sulfo group, a nitro group, an aromatic hydrocarbon ring group, and an aromatic heterocyclic ring group; a group having an aromatic ketone skeleton; or a group having an aromatic hydrocarbon ring group or an aromatic heterocyclic ring group and a conjugated bond group which forms a continuous conjugated system with the aromatic hydrocarbon ring group or aromatic heterocyclic ring group. １１ and R １２ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Z １１ represents an oxygen atom or a sulfur atom, m1 represents 0 or 1, if n1 is 0, then m1 represents 0, n1 represents an integer from 0 to 4, p1 represents 0 or 1, X １１ Y represents a boron atom, an aluminum atom, a gallium atom, or an indium atom.１１ represents an organic onium cation. However, R １３ However, R is a group having a condensed polycyclic aromatic heterocyclic group, an aromatic ketone skeleton, or an aromatic heterocyclic group and a conjugated bond group that forms a continuous conjugated system with the aromatic heterocyclic group, １３ One of the bonds between the heteroatoms that make up the Z １１ In the case of representing a coupling with, the modes in which m1 = n1 = 0 and m1 = 1 are excluded.

[0010] <2> R in general formula (1) １３ The compound described in <1>, wherein the substituent may be a fused polycyclic aromatic hydrocarbon ring group or a fused polycyclic aromatic heterocyclic ring group, or a group represented by any of the general formulas (3) to (6-2) described later. <3> Y in general formula (1) １１ The compound according to <1> or <2>, wherein the organic onium cation represented by is selected from sulfonium cation, iodonium cation, ammonium cation, phosphonium cation and pyridinium cation. <4> In general formula (1), Y １１ The organic onium cation represented by is one of the general formulas (7) to (11) described later, and is a compound according to any one of <1> to <3>. <5> R in general formula (1) １３ However, it is a group represented by one of the general formulas (3) to (6-2) described later, X １１ is a boron atom, and Ar １１ ~Ar １３ A compound described in any one of <1> to <4>, wherein the group is the same. <6> In general formula (1), Y １１ However, the compound is one of the compounds described in any one of <1> to <5>, which is a group represented by general formula (7) or (8) described later. <7> R in general formula (1) １３However, the compound is one of the compounds described in <1> to <6>, which is a group represented by the general formula (4), (5-1), or (5-2) described later. <8> R in general formula (4) ４１ ga-S-CH ２ -CH ２ It is an alkylene group containing - or an alkenylene group containing -S-CH=CH-, Ar ４１ A compound according to any one of <2> to <7>, wherein is a phenyl group which may have substituents. <9> Ar in general formula (5-1) ５１１ and Ar ５１２ , and Ar in general formula (5-2) ５２１ and Ar ５２２ The compound according to any one of <2> to <8>, wherein each is independently a phenyl group or a monocyclic aromatic heterocyclic group which may have substituents.

[0011] <10> The compound represented by general formula (1) is the compound described in <1>, which is represented by the following general formula (1'). In general formula (1'), Ar １１’ ~Ar １３’ Each independently represents a halogen group and a phenyl group having at least one C1-C4 alkyl group containing a fluorine atom as substituents, and Ar １１’ ~Ar １３’ These are the same group, R １３’ X represents a group represented by the general formula (4'), (5'-1), or (5'-2) described later, １１’ represents a boron atom, Y １１’ R represents a group represented by the general formula (7) or (8) described later, １１ , R １２ Z １１ m1, n1, and p1 are the same as those in general formula (1).

[0012] <11> The compound according to any one of <1> to <10>, wherein p1 is 1. <12> A photoacid generator containing the compound according to any one of <1> to <11>. <13> An acid-reactive composition containing the compound according to any one of <1> to <11> and an acid-reactive compound. <14> The acid-reactive composition according to <13>, wherein the acid-reactive compound is a compound having one or more groups selected from epoxy groups, oxetane groups, alkoxysilyl groups, and vinyl groups. <15> The acid-reactive composition according to <13> or <14>, wherein the acid-reactive composition is a resist composition. <16> An acid generation method comprising irradiating the compound according to any one of <1> to <11> with an active energy ray.

[0013] The present invention can provide a compound possessing excellent thermal latent properties and high UV sensitivity, and a photoacid generator containing this compound. Furthermore, the present invention can provide an acid-reactive composition containing the above compound, and a method for generating acid using the above compound. The above and other features and advantages of the present invention will become clearer from the following description.

[0014] In this invention, when describing content, reaction conditions, etc., by indicating numerical ranges, if the upper and lower limits of the numerical range are described separately, either upper or lower limit can be appropriately combined to form a specific numerical range. On the other hand, when multiple numerical ranges represented by "~" are set and described, the upper and lower limits forming the numerical range are not limited to the specific combinations written before and after "~" as a specific numerical range, but can be a numerical range formed by appropriately combining the upper and lower limits of each numerical range. In this invention, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits.

[0015] In this invention, the term "compound" includes not only the compound itself, but also its salts and ions. Furthermore, it includes derivatives in which parts have been altered, such as by introducing substituents, to the extent that the effects of the present invention are not impaired.

[0016] In this invention, substituents, linking groups, etc. (hereinafter referred to as substituents, etc.) that are not specified as substituted or unsubstituted may have appropriate substituents. Therefore, in this invention, even when simply referred to as a YYY group, this YYY group includes not only an unsubstituted form but also a form with substituents. The same applies to compounds that are not specified as substituted or unsubstituted. Preferred substituents include, for example, groups selected from substituent Z described later. In this invention, when there are multiple substituents, etc. indicated by a specific symbol, or when multiple substituents, etc. are specified simultaneously, it means that each substituent, etc. may be the same as or different from the others. Furthermore, even if not specifically stated, when multiple substituents, etc. are adjacent, they may be linked to each other or fused to form a ring. In this invention, when the number of carbon atoms of a group is specified, this number of carbon atoms refers to the number of carbon atoms of the group itself, unless otherwise specified in this invention. In other words, if this group has a further substituent (excluding groups such as branched alkyl groups, where the further substituent can be interpreted as a single group), it means the number of carbon atoms when counting without including the carbon atoms of the substituent.

[0017] [[Compound represented by general formula (1)]] The compound represented by the following general formula (1) (in this invention, it may be referred to as "the compound of the present invention" or "compound (1)") exhibits excellent thermal potential and high UV sensitivity, and upon irradiation with active energy rays, it can remove acids, specifically X １１ (Ar １１ ) (Ar １２ ) (Ar １３ ) can be generated. Therefore, the compound of the present invention functions effectively as a photoacid generator that combines excellent thermal potential and high UV sensitivity, and can be suitably used as a photoacid generator that possesses the above-mentioned excellent properties.

[0018]

[0019] [Ar １１ ~Ar １３ In general formula (1), Ar １１ ~Ar１３ Each of these independently represents an aromatic hydrocarbon ring group having at least one halogen group and one C1-C4 alkyl group containing a fluorine atom as substituents. １１ ~Ar １３ The aromatic hydrocarbon ring group constituting the compound is not particularly limited and can be any hydrocarbon group that exhibits so-called aromaticity as a whole, and may include an aliphatic hydrocarbon ring. The aromatic hydrocarbon ring group may be a monocyclic aromatic hydrocarbon ring group or a polycyclic aromatic hydrocarbon ring group (also called a "condensed polycyclic aromatic hydrocarbon ring group"), but a monocyclic aromatic hydrocarbon ring group is preferred. An example of a monocyclic aromatic hydrocarbon ring group is the phenyl group. An example of a condensed polycyclic aromatic hydrocarbon ring group is a monovalent group obtained by removing one arbitrary hydrogen atom from a ring formed by the condensation of multiple monocyclic aromatic hydrocarbon rings and / or monocyclic aliphatic hydrocarbon rings, and includes, for example, a monovalent group obtained by removing one arbitrary hydrogen atom from an aromatic hydrocarbon (acene) ring having a structure in which benzene rings are condensed in a straight line. The number of condensed rings is not particularly limited and can be, for example, 2 to 5. Examples of such condensed polycyclic aromatic hydrocarbon ring groups include monovalent groups obtained by removing one arbitrary hydrogen atom from a condensed polycyclic aromatic hydrocarbon ring made of acenes such as naphthalene, anthracene, and pentacene; monovalent groups obtained by removing one arbitrary hydrogen atom from a condensed polycyclic aromatic hydrocarbon ring made of chrysene, pyrene, triphenylene, benzopyrene, coronene, etc.; and monovalent groups obtained by removing one arbitrary hydrogen atom from a condensed polycyclic aromatic hydrocarbon ring made of fluorene.

[0020] Ar １１ ~Ar １３ The halogen group to be substituted on the aromatic hydrocarbon ring group constituting the compound is not particularly limited, and examples include halogen atoms, among which fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc., are preferred, and fluorine atoms are more preferred in terms of the catalytic activity of the acid generated from the compound of the present invention.

[0021] Ar １１ ~Ar １３The C1-C4 alkyl group (C1-C4 fluoroalkyl group) containing a fluorine atom which substitutes the aromatic hydrocarbon ring group constituting [it] is not particularly limited, and may be an alkyl group in which all hydrogen atoms are substituted with fluorine atoms (perfluoroalkyl group), or may be an alkyl group in which some hydrogen atoms are substituted with fluorine atoms. The position where the fluorine atom substitutes is not particularly limited, and can be an appropriate position with respect to the carbon atom bonded to X １１ and can be an appropriate position with respect to the carbon atom bonded to it. The carbon chain structure of the fluoroalkyl group is not particularly limited, and may be any of a straight-chain structure, a branched structure, and a cyclic structure.

[0022] The number of halogeno groups and / or fluoroalkyl groups substituting the aromatic hydrocarbon ring group is not particularly limited, and can be appropriately determined within the range of 1 or more and not more than the total number of hydrogen atoms possessed by the aromatic hydrocarbon ring group. For example, when the aromatic hydrocarbon ring group is a phenyl group, it can be 1 to 5, and from the viewpoint of the catalytic activity of the acid generated from the compound of the present invention, 5 is preferable. Incidentally, the position where the halogeno group and / or fluoroalkyl group substitutes is not particularly limited, and can be an appropriate position with respect to the ring-constituting carbon atom bonded to X １１ and can be an appropriate position with respect to the ring-constituting carbon atom bonded to it. For example, when the aromatic hydrocarbon ring group is a phenyl group, it may be any of the 2nd to 6th positions with respect to the ring-constituting carbon atom bonded to X １１ and can be an appropriate position with respect to the ring-constituting carbon atom bonded to it.

[0023] As the aromatic hydrocarbon ring group having the above-mentioned substituent that can be taken as Ar １１ to Ar １３ , a phenyl group having at least one of a halogeno group and the above alkyl group as a substituent is preferable, a phenyl group having at least one halogeno group as a substituent, and a phenyl group having at least one C1-C4 perfluoroalkyl group as a substituent are more preferable, and from the viewpoint of the catalytic activity of the acid generated from the compound of the present invention, a phenyl group having 5 halogeno groups as a substituent is even more preferable, and a phenyl group having 5 fluorine atoms as a substituent (pentafluorophenyl group) is particularly preferable. As Ar １１ to Ar １３ , the aromatic hydrocarbon ring groups having the above-mentioned substituent that can be taken respectively may be different from each other, but are preferably the same.

[0024] [R １３ In the general formula (1), R １３ takes any one of the following groups A to C. <Group A> As a substituent, a benzyl group (C ６ H ５ CH ２ -), an alkoxy group, an alkyl group having 1 to 20 carbon atoms which may have a branched or cyclic structure, an aliphatic heterocyclic group, a halogeno group, a hydroxy group, a sulfo group, a nitro group, an aromatic hydrocarbon ring group and an aromatic heterocyclic group, and may have at least one group selected from the group consisting of a condensed polycyclic aromatic hydrocarbon ring group or a condensed polycyclic aromatic heterocyclic group <Group B> A group having an aromatic ketone skeleton <Group C> A group having an aromatic hydrocarbon ring group or an aromatic heterocyclic group and a conjugated bond group forming a conjugated system continuous with this group

[0025] <Group A> In the description of Group A, the condensed polycyclic aromatic hydrocarbon ring group and the condensed polycyclic aromatic heterocyclic group constituting Group A that R １３ can take as R may be simply referred to as a "condensed polycyclic group" together. The condensed polycyclic aromatic hydrocarbon ring group constituting Group A that R １３ can take as R is not particularly limited, and examples thereof include the above-described condensed polycyclic aromatic hydrocarbon ring groups described as the aromatic hydrocarbon ring groups constituting Ar １１ to Ar １３ . Among them, as the condensed polycyclic aromatic hydrocarbon ring group constituting Group A, a monovalent group obtained by removing any one hydrogen atom from a condensed polycyclic aromatic hydrocarbon ring composed of acene, a monovalent group obtained by removing any one hydrogen atom from a condensed polycyclic aromatic hydrocarbon ring composed of chrysene, pyrene, triphenylene, benzopyrene, coronene, etc. are preferable, and a monovalent group obtained by removing any one hydrogen atom from a condensed polycyclic aromatic hydrocarbon ring composed of acene is more preferable. R １３The fused polycyclic aromatic heterocyclic group that constitutes group A is not particularly limited, and only groups that contain at least one heteroatom (for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, etc.) as ring constituent atoms and exhibit so-called aromaticity as a whole are acceptable. It may also contain an aromatic hydrocarbon ring (benzene ring), an aliphatic hydrocarbon ring, or an aliphatic heterocyclic ring. However, if this fused polycyclic aromatic heterocyclic group also corresponds to group B described later, it will be referred to as group B instead of group A. The monocyclic aromatic heterocyclic ring constituting the fused polycyclic aromatic heterocyclic group is not particularly limited, but it is preferably a five-membered ring or a six-membered ring. Examples of such monocyclic aromatic heterocyclic rings include five-membered rings such as furan, thiophene, pyrrole, oxazole, thiazole, imidazole, and pyrazole, and six-membered rings such as pyridine, pyrazine, and pyrimidine. The number of monocyclic rings (number of fused rings) constituting the fused polycyclic aromatic heterocyclic group is not particularly limited and can be, for example, two to five. Examples of such fused polycyclic aromatic heterocyclic groups include monovalent groups obtained by removing one arbitrary hydrogen atom from fused polycyclic aromatic heterocyclic rings such as benzofuran, benzothiophene, indole, carbazole, quinoline, acridine, and benzimidazole.

[0026] R １３ A preferred condensed polycyclic group is a condensed polycyclic aromatic hydrocarbon ring group, which can constitute group A.

[0027] Substituents Z that may be present on the condensed polycyclic group Ｒ１３ This will be explained. Substituent Z Ｒ１３ The alkoxy group, which is one of these groups, is not particularly limited and is, for example, the same as the alkoxy group in substituent Z described later. Substituent Z Ｒ１３ One of these is an alkyl group having 1 to 20 carbon atoms, which is not particularly limited and is the same as the alkyl group in substituent Z described later. The carbon chain structure of the alkyl group as substituent is not particularly limited and is preferably a linear structure, but may have a branched or cyclic structure. In the present invention, the cyclic structure is not particularly limited and includes condensed polycyclic structures such as spiro rings and crosslinked ring structures in addition to monocyclic structures. Substituent Z Ｒ１３One of these is an aliphatic heterocyclic group, which is not particularly limited and is the same as the heterocyclic group in substituent Z described later that corresponds to an aliphatic heterocyclic group. Substituent Z Ｒ１３ One of them is the halogen group, which is not particularly limited, Ar １１ ~Ar １３ This is the same as the halogen group that substitutes for the aromatic hydrocarbon ring group that constitutes it. Substituent Z Ｒ１３ One of them is an aromatic hydrocarbon ring group, which is not particularly limited, Ar １１ ~Ar １３ It is the same as the aromatic hydrocarbon ring group that constitutes it. Substituent Z Ｒ１３ One of these is an aromatic heterocyclic group, which is not particularly limited. It is sufficient if it contains at least one heteroatom (for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, etc.) as a ring constituent atom and exhibits so-called aromaticity as a whole. It may also include an aromatic hydrocarbon ring (benzene ring), an aliphatic hydrocarbon ring, or an aliphatic heterocycle. The aromatic heterocyclic group may be a monocyclic aromatic heterocyclic group or a fused polycyclic aromatic heterocyclic group. The monocyclic aromatic heterocyclic group is a monovalent group obtained by removing one arbitrary hydrogen atom from a monocyclic aromatic heterocycle, and the monocyclic aromatic heterocycle is R １３ As explained in the section on monocyclic aromatic heterocyclic rings that constitute the fused polycyclic aromatic heterocyclic group A, which can be taken as such, R is a possible example. １３ As explained in the section on the fused polycyclic aromatic heterocyclic groups that constitute group A, which can be taken as such, in this invention, when a group, ring, etc. represented by a specific symbol is the same as a group, ring, etc. represented by another symbol, or as explained for a group, ring, etc. represented by another symbol, it means that the basic structure of the group, ring, etc. is the same, and differences in valency are not considered.

[0028] Substituent Z Ｒ１３ Among the above, alkoxy groups, alkyl groups, and halogen groups are preferred, with alkoxy groups and halogen groups being more preferred.

[0029] The substituent Z of the above condensed polycyclic group Ｒ１３The number is not particularly limited and can be appropriately determined within the range of one or more, and less than or equal to the total number of hydrogen atoms in the condensed polycyclic group, for example, it can be 1 to 3. Also, the substituent Z Ｒ１３ The position of the fused polycyclic group to which is substituted is not particularly limited, Z １１ The position can be appropriate for the ring-forming atom that bonds with it, for example, it can be any of positions 2 to 5.

[0030] R １３ As for the group A that can be used, the preferred substituent Z is one that has good thermal potential and UV sensitivity. Ｒ１３ It is preferable that the ring group is a condensed polycyclic aromatic hydrocarbon ring group having one or more of these elements.

[0031] <Group B> R １３ The group B that can be used is a group having an aromatic ketone skeleton. Groups having an aromatic ketone skeleton include both groups consisting solely of an aromatic ketone skeleton and groups having an aromatic ketone skeleton and a residual group. The aromatic ring constituting the aromatic ketone skeleton is not particularly limited and includes aromatic hydrocarbon rings and aromatic heterocycles. In terms of thermal latentness and UV sensitivity, it is preferable to include at least an aromatic hydrocarbon ring. The aromatic hydrocarbon ring and aromatic heterocycle are not particularly limited and the substituent Z may be present on the condensed polycyclic group constituting group A. Ｒ１３ The rings are the same as those that form the aromatic hydrocarbon ring group and aromatic heterocyclic ring described above. However, the above aromatic ring means a ring bonded to a carbonyl group constituting the aromatic ketone skeleton, and in one embodiment of the present invention, it is not interpreted as a fused ring with a ring containing a carbonyl group (ketone group) constituting the aromatic ketone skeleton. The above aromatic ring is preferably an aromatic hydrocarbon ring, and preferably a monocyclic aromatic hydrocarbon ring.

[0032] The remaining groups are groups having an aromatic ketone skeleton and Z １１ Depending on the manner of bonding, the terminal group or Z １１ A linking group to the above aromatic ring is an example. That is, the remaining group is a group having an aromatic ketone skeleton and Z １１ In the configuration in which they are bonded, they become terminal groups, and the group having an aromatic ketone skeleton is located outside the aromatic ring Z １１In the embodiment where it is bonded with, it becomes a linking group. In the present invention, R １３ etc. Z １１ Z １１ The phrase "combining with, etc." is explained for convenience by assuming that m1 is 1 in general formula (1), but R １１ and R １２ This includes forms in which the group is bonded to a carbon atom having a bond (in the form where m1 is 0 and n1 is 1), a carbonyl carbon atom (in the form where both m1 and n1 are 0), or an ether oxygen atom (in the form where m1, n1, and p1 are 0). The remaining group (terminal group) is not particularly limited as long as it is a group that can bond to the carbonyl group of the aromatic ketone skeleton, for example, each group selected from substituent Z described later, preferably terminal groups in a group represented by any of the general formulas (3) to (6-2) described later, for example, residues obtained by excluding the ring group having a bond * and the carbonyl group in each formula. The terminal group may be an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, for example, R in general formula (3) described later ３１ A preferred aromatic hydrocarbon ring group or aromatic heterocyclic group may have substituents that can be taken as such.

[0033] The linking group is the carbonyl group of the aromatic ketone skeleton and Z １１ The linking group is not particularly limited as long as it can bond with the other group, for example, a divalent group obtained by further removing any hydrogen atom etc. from each group selected from substituent Z described later. This linking group may bond with the ring constituent atoms of the aromatic ring constituting the aromatic ketone skeleton to form a fused ring with the aromatic ring. Specifically as a linking group, R of the group represented by general formula (4) described later ４１ Examples include: In a group having an aromatic ketone skeleton, if the terminal group or linking group has an aromatic ring, the aromatic ring constituting the aromatic ketone skeleton is Z １１ The aromatic ring bonded to Z can be interpreted as either the aromatic ring attached to Z or the aromatic ring possessed by the terminal group or linking group, but in the present invention, Z is usually used. １１ The aromatic ring bonded to it is interpreted as an aromatic ring that constitutes the aromatic ketone skeleton.

[0034] Groups having an aromatic ketone skeleton are Z １１ The above-described bonding configuration can be adopted for the aromatic ring and Z that constitute the aromatic ketone skeleton. １１ A configuration in which the carbonyl group of the aromatic ketone skeleton and Z are bonded together. １１ In a configuration in which the two are bonded, the linking group constituting the group having an aromatic ketone skeleton and Z １１ A configuration in which the aromatic ring constituting the aromatic ketone skeleton and Z are bonded is preferred. １１ In a configuration in which the two are bonded, the linking group constituting the group having an aromatic ketone skeleton and Z １１ A configuration in which the two are combined is more preferable.

[0035] A group having an aromatic ketone skeleton may have substituents on the aromatic ring and the remaining group constituting the aromatic ketone skeleton. The substituents that a group having an aromatic ketone skeleton may have are not particularly limited and include each group selected from substituent Z described later, and specifically include substituents that may be present on the group represented by each sign in any of the general formulas (3) to (6-2) described later.

[0036] The group having an aromatic ketone skeleton is preferably a group represented by any of the following general formulas (3) to (6-2), more preferably a group represented by the following general formulas (4), (5-1), or (5-2), in that it can achieve a high level of both thermal potential and UV sensitivity, and even more preferably a group represented by the following general formulas (4'), (5'-1), or (5'-2).

[0037] In general formula (3), Ar ３１ Ar represents an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents. ３１ The rings forming the aromatic hydrocarbon ring group and the aromatic heterocyclic ring are not particularly limited, and the substituent Z may be present in the condensed polycyclic group constituting group A. Ｒ１３ These are the same rings that form aromatic hydrocarbon ring groups and aromatic heterocyclic ring groups as described above. However, Ar ３１As such, an aromatic hydrocarbon ring group is preferred, and a monocyclic aromatic hydrocarbon ring group (phenyl group) is more preferred. In the present invention, when the term "phenyl group" is used for a ring group represented by a specific symbol, it is used as a term to mean a benzene ring having a valency that is compatible with the ring group represented by that specific symbol. Therefore, for example, Ar ３１ The above phenyl group that can be used as means a benzene ring group. ３１ The substituents that the aromatic hydrocarbon ring group and aromatic heterocyclic group constituting the compound may each have are not particularly limited, and include, for example, each group selected from substituent Z described later, among which alkoxy groups, halogen atoms, alkyl groups, etc., are preferred.

[0038] In general formula (3), R ３１ This includes an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, a C1-C10 alkyl group which may have a branched or cyclic structure, an aliphatic heterocyclic group, a hydroxyl group, an alkoxy group, a sulfo group, a nitro group, a carboxyl group, or -SO ２ -Ar ３２ The group represented by (Ar ３２ ) represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents.

[0039] R ３１ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, and for example, including substituents, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents (as mentioned above, valency is not considered; the same applies hereafter). R ３１ The alkyl group having 1 to 10 carbon atoms that may have a branched or cyclic structure is not particularly limited, for example, except for the number of carbon atoms, １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３ It is the same as an alkyl group having 1 to 20 carbon atoms. ３１ The number of carbon atoms in the alkyl group that can be used is 1 to 10, and preferably 1 to 6.

[0040] R ３１ The aliphatic heterocyclic group that can be used as is not particularly limited, and for example, a group corresponding to the aliphatic heterocyclic group among the heterocyclic groups in substituent Z described later can be cited. ３１ The alkoxy group that can be used is not particularly limited, and is, for example, the same as the alkoxy group in substituent Z described later. ３１ It can be taken as -SO ２ -Ar ３２ The base represented by Ar is not particularly limited. ３２ R is an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents, which can be taken as -SO ２ -Ar ３２ Examples of groups represented by this include the arylsulfonyl group in substituent Z, which will be described later.

[0041] R ３１ Among the above groups, aromatic hydrocarbon ring groups or aromatic heterocyclic ring groups, which may have substituents, are preferred.

[0042] In general formula (3), R ３２ and R ３３ Each of these independently represents an alkyl or alkoxy group having 1 to 5 carbon atoms. ３２ and R ３３ The alkyl group that can be used is not particularly limited; for example, other than the number of carbon atoms, R １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３ It is the same as an alkyl group having 1 to 20 carbon atoms. ３２ and R ３３ The alkoxy group that can be used is the same as the alkoxy group in substituent Z described later. ３２ and R ３３ The number of carbon atoms in each of the alkyl and alkoxy groups that can be taken as such is preferably 1 to 5, and more preferably 1 or 2. ３２ and R ３３ They may be the same or different from one another.

[0043] In general formula (3), R ３１ and R ３２ and R ３３ These two elements may be the same or different from each other. ３１ and R ３２ and R ３３ The preferred combinations with are not particularly limited, for example, R ３１ A ring group or heterocyclic aromatic hydrocarbon group which may have substituents, and R ３２ and R ３３ Examples include combinations with alkyl groups and / or alkoxy groups. In general formula (3), R ３１ ~R ３３ Two or three of these may be connected to each other to form a ring structure.

[0044] In general formula (3), *- represents Ar ３１ The carbon atoms that make up the ring structure and Z in the general formula (1) above １１ This represents a coupling that joins two things together.

[0045] Examples of compounds (1) having a group represented by general formula (3) include the following compounds, but the present invention is not limited to these compounds. In the following compounds, Me represents a methyl group.

[0046] In general formula (4), Ar ４１ Ar represents an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents. ４１ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, and includes substituents, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, but Ar ４１ A phenyl group which may have substituents is preferred.

[0047] In general formula (4), R ４１R represents an alkylene group having 1 to 10 carbon atoms that may have substituents, or an alkenylene group having 2 to 10 carbon atoms that may have substituents, and which may have an ether group (-O-), a sulfide group (-S-), or a carbonyl group (-CO-) in its molecular chain. ４１ The number of carbon atoms in the alkylene group (excluding the carbonyl carbons if a carbonyl group is present) is preferably 1 to 6, more preferably 1 to 3, and the lower limit in each range can be set to 2. ４１ The number of carbon atoms in the alkenylene group (excluding the number of carbonyl carbons if a carbonyl group is present) is preferably 2 to 6, and more preferably 2 or 3. ４１ The carbon chain structure of the alkylene group and alkenylene group that can be used is not particularly limited and may be a linear, branched, or cyclic structure. The alkylene group or alkenylene group is Ar in general formula (4). ４１ It bonds with the ring constituent atoms, Ar ４１ It forms a fused ring with the other group. The alkenylene group may have multiple C-C double bonds.

[0048] The total number of ether groups, sulfide groups, and carbonyl groups in the alkylene group and alkenylene group can be one or two. The ether groups, sulfide groups, and carbonyl groups may be located inside or at the ends of the carbon chain structure of the alkylene group and alkenylene group, and it is preferable that they be located at the ends. ４１ It is more preferable that it is bonded to a ring constituent atom. ４１ The alkylene and alkenylene groups that can be used are preferably alkylene or alkenylene groups that do not have an ether group, a sulfide group, or a carbonyl group, or alkylene or alkenylene groups that have an ether group or a sulfide group, and more preferably alkylene groups that have a sulfide group. Examples of alkylene or alkenylene groups that have a sulfide group include -S-alkylene group- or -S-alkenylene group-, and -S-CH ２ -CH ２Preferably, an alkylene group containing - or an alkenylene group containing -S-CH=CH- is preferred, and -S-CH ２ -CH ２ More preferably, an alkylene group with a total of 2 to 6 carbon atoms including - or an alkenylene group with a total of 2 to 6 carbon atoms including -S-CH=CH-. ２ -CH ２ The alkylene group containing - is preferably an alkylene group with a total of 2 or 3 carbon atoms, -S-CH ２ -CH ２ - Groups are more preferred. As for alkenylene groups containing -S-CH=CH-, alkenylene groups with a total of 2 or 3 carbon atoms are preferred.

[0049] The group represented by general formula (4) is Ar ４１ and R ４１ Examples include groups obtained by appropriately combining and a carbonyl group, and the above preferred Ar ４１ and preferred R ４１ A group combining and a carbonyl group is preferred, Ar ４１ A phenyl group which may have substituents, and R ４１ as -S-CH ２ -CH ２ A more preferable group is one that contains an alkylene group with - or an alkenylene group containing -S-CH=CH- combined with a carbonyl group.

[0050] In general formula (4), *- represents the above Ar ４１ As shown, in the present invention, Ar ４１ or R ４１ The carbon atoms that make up and Z in the above general formula (1) １１ This represents a coupling that joins two things. ４１ In particular, the above-mentioned -S-alkylene group-, -S-alkenylene group-, -S-CH ２ -CH ２ When an alkylene group containing -, an alkenylene group containing -S-CH=CH-, etc., has a bond*, the position of the bond is not particularly limited, and for example, in each alkylene group or alkenylene group, it may be a carbon atom adjacent to the sulfur atom or any other carbon atom. ４１ It can be taken as -S-CH２ -CH ２ For alkylene groups containing - and alkenylene groups containing -S-CH=CH-, for convenience, "-CH ２ The notations "-", "-CH=", and "=CH-" indicate that when these carbon atoms have bonding bonds*, the resulting structure is obtained by removing the "H" (hydrogen atom) bonded to the carbon atom. In this case, "S-CH ２ -CH ２ "Alkylene group containing -" and "Alkenylene group containing -S-CH=CH-" are examples of "S-C(R Ｒ４１ ) ２ - (R Ｒ４１ ) ２ - containing an alkylene group", -S-C(R Ｒ４１ ) = C(R Ｒ４１ It can also be written as "an alkenylene group containing )." Here, R Ｒ４１ These are, respectively, a hydrogen atom or R ４１ If it has a coupling *, indicate the coupling and S-C(R Ｒ４１ ) ２ - (R Ｒ４１ ) ２ In alkylene groups containing -, there are four R Ｒ４１ One of them is a bonding bond, and the remaining three represent hydrogen atoms, -S-C(R Ｒ４１ ) = C(R Ｒ４１ In alkenylene groups containing )-, there are two R Ｒ４１ One of them represents a bonding bond, and the other represents a hydrogen atom.

[0051] Examples of compounds (1) having a group represented by general formula (4) include the compounds synthesized in the examples, but the present invention is not limited to these compounds.

[0052] In general formula (5-1), Ar ５１１ and Ar ５１２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents. ５１１ and Ar ５１２ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, and includes substituents, Ar ３１It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, but Ar ５１１ and Ar ５１２ Each of these is preferably a phenyl group or a monocyclic aromatic heterocyclic group, and more preferably a phenyl group, which may have a substituent. The monocyclic aromatic heterocyclic group is not particularly limited, and for example, substituent Z may be present on the fused polycyclic group constituting group A. Ｒ１３ It is the same as the monocyclic aromatic heterocyclic group described as an aromatic heterocyclic group. ５１１ and Ar ５１２ They may be the same or different from one another.

[0053] In general formula (5-1), R ５１１ and R ５１２ Each of these independently represents a single bond or an alkylene group with 1 to 4 carbon atoms. ５１１ and R ５１２ The alkylene group that can be used is not particularly limited; for example, it is the same as the group obtained by removing one more hydrogen atom from the alkyl group in substituent Z described later, except for the number of carbon atoms. The carbon chain structure of the alkylene group is not particularly limited; a linear structure is preferred, but it may also have a branched or cyclic structure. ５１１ and R ５１２ The number of carbon atoms in the alkylene group that can be taken as is preferably 1 or 2. ５１１ and R ５１２ It is preferable that it is a single bond or a methylene group. ５１１ and R ５１２ They may be the same or different from each other. ５１１ and R ５１２ The combinations are preferably one in which both are single bonds, or one in which one is a single bond and the other is an alkylene group (preferably a methylene group).

[0054] In general formula (5-1), A ５１ R represents a single bond, an oxygen atom, a sulfur atom, or a carbonyl group, with a single bond, an oxygen atom, or a sulfur atom being preferred. In general formula (5-1), R ５１１ and R ５１２ and A ５１The base to be combined with is not particularly limited, R ５１１ and R ５１２ What can be taken as A ５１ Examples of groups that can be taken as such include R ５１１ and R ５１２ At least one of them is an alkylene group, A ５１ Preferred combinations include a single bond, an oxygen atom, a sulfur atom, or a carbonyl group. More preferably, -R ５１１ -A ５１ -R ５１２ -As a group, an alkylene group (R ５１１ and R ５１２ One of them is an alkylene group A ５１ A combination in which the bond is a single bond, or a single bond or an alkylene group (R ５１１ ) - Oxygen atom, sulfur atom or carbonyl group (A ５１ ) - Single bond or alkylene group (R ５１２ )- are examples. In the group represented by general formula (5-1), R ５１１ and R ５１２ and A ５１ While any combination is possible, R ５１１ , R ５１２ and A ５１ None of these will result in a single bond. ５１１ , R ５１２ and A ５１ If all of them are single bonds, the group is represented by the general formula (5-2) described later.

[0055] As a group represented by the general formula (5-1), Ar ５１１ and Ar ５１２ and R ５１１ and R ５１２ and A ５１ Examples of groups obtained by appropriately combining the above include the preferred Ar ５１１ and Ar ５１２ and preferred R ５１１ and R ５１２ And a favorable A ５１ A group combining Ar is preferred. ５１１ and Ar ５１２A phenyl group or monocyclic aromatic heterocyclic group which may have substituents, and R ５１１ and R ５１２ As a single bond or an alkylene group having 1 to 4 carbon atoms and A ５１ A group combining an oxygen atom, a sulfur atom, or a carbonyl group is more preferable.

[0056] In general formula (5-1), *- represents Ar ５１１ The carbon atoms that make up the compound and Z in general formula (1) １１ This represents a bonding action that connects and . Note that in general formula (5-1), Ar ５１１ and Ar ５１２ Each of these consists of a ring-forming atom bonded to the carbonyl group and R ５１１ or R ５１２ It is preferable that the ring group is composed of atoms different from the ring constituent atoms that bond to it (i.e., it is a divalent or trivalent ring group).

[0057] Examples of compounds (1) having a group represented by general formula (5-1) include the compounds synthesized in the examples, but the present invention is not limited to these compounds.

[0058] In general formula (5-2), Ar ５２１ and Ar ５２２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents. ５２１ and Ar ５２２ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, and includes substituents, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, but Ar ５２１ and Ar ５２２ Each of these is preferably a phenyl group or a monocyclic aromatic heterocyclic group, and more preferably a phenyl group, which may have a substituent. The monocyclic aromatic heterocyclic group is not particularly limited, and for example, substituent Z may be present on the fused polycyclic group constituting group A. Ｒ１３ It is the same as the monocyclic aromatic heterocyclic group described as an aromatic heterocyclic group. ５２１ and Ar５２２ They may be the same or different from each other. However, Ar ５２１ and Ar ５２２ In Ar ５２１ A carbon atom constituting an aromatic hydrocarbon ring group or aromatic heterocyclic group that can be taken as, and Ar ５２２ Among the carbon atoms constituting an aromatic hydrocarbon ring group or aromatic heterocyclic group that can be taken as, Ar in general formula (5-2) ５２１ -C(=O)-Ar ５２２ The carbon atoms involved in the bonding, i.e., the carbon atoms bonded to the carbonyl carbon atom, may also be bonded to each other at the α-position (2-position). The bond between the α-position carbon atoms mentioned above is indicated by a dashed line in general formula (5-2).

[0059] The group represented by the general formula (5-2) is Ar ５２１ and Ar ５２２ Examples of groups obtained by appropriately combining these include combinations of optionally substituted aromatic hydrocarbon ring groups, combinations of optionally substituted aromatic hydrocarbon ring groups and optionally substituted aromatic heterocyclic groups, and combinations of optionally substituted aromatic heterocyclic groups. In each of the above combinations, optionally substituted phenyl groups are preferred as the optionally substituted aromatic hydrocarbon ring group, and optionally substituted monocyclic aromatic heterocyclic groups are preferred as the optionally substituted aromatic heterocyclic groups.

[0060] In general formula (5-2), *- represents Ar ５２１ The carbon atoms that make up the compound and Z in general formula (1) １１ This represents a coupling that joins two things together.

[0061] Examples of compounds (1) having a group represented by general formula (5-2) include the compounds synthesized in the examples, but the present invention is not limited to these compounds.

[0062] In general formula (6-1), Ar ６１１ Ar represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. ６１１The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, and includes substituents, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, but Ar ６１１ A phenyl group which may have substituents is preferred.

[0063] In general formula (6-1), *- represents the carbonyl carbon and Z in general formula (1). １１ This represents a coupling that joins two things together.

[0064] Examples of compounds (1) having a group represented by general formula (6-1) include the compounds synthesized in the examples, but the present invention is not limited to these compounds.

[0065] In general formula (6-2), Ar ６２１ Ar represents an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents. ６２１ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, and includes substituents, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents.

[0066] In general formula (6-2), R ６２２ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group, hydroxyl group, sulfo group, nitro group, carboxyl group, or a C1-C10 alkyl group which may have a branched or cyclic structure and may have heteroatoms in its molecular chain. ６２２ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, and includes substituents, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents. ６２２The alkyl group having 1 to 10 carbon atoms, which may have a branched or cyclic structure and may have heteroatoms in its molecular chain, is not particularly limited. ６２２ The carbon chain structure of the alkyl group that can be used is not particularly limited, and usually has a linear structure, but may also have a branched or cyclic structure. ６２２ The number of carbon atoms in the alkyl group that can be used is preferably 1 to 6, and more preferably 1 or 2. ６２２ The heteroatoms that the alkyl group may have are not particularly limited, and include, for example, nitrogen, oxygen, sulfur, and phosphorus atoms. The total number of heteroatoms that the alkyl group may have is not particularly limited, and can be, for example, one or two. The heteroatoms may be located inside or at the ends of the carbon chain structure of the alkyl group.

[0067] The group represented by the general formula (6-2) is Ar ６２１ and R ６２２ Examples of groups formed by appropriately combining Ar ６２１ and the above-mentioned preferred R ６２２ A base combining the two is preferable.

[0068] In general formula (6-2), *- represents Ar ６２１ The carbon atoms that make up the compound and Z in general formula (1) １１ This represents a coupling that joins two things together.

[0069] The group represented by the above general formula (4), (5-1), or (5-2) is preferably the group represented by the following general formula (4'), (5'-1), or (5'-2), respectively.

[0070] In general formula (4'), Ar ４１’ This is Ar in general formula (4). ４１ A preferred embodiment represents a phenyl group which may have substituents. A substituent which the phenyl group may have is Ar ３１ Examples of substituents that may be present on an aromatic hydrocarbon ring group or an aromatic heterocyclic group are that can be substituted.

[0071] In general formula (4'), R ４１’ R in general formula (4) ４１ A preferred embodiment is -S-CH ２ -CH ２ - represents an alkylene group with a total of 2 to 6 carbon atoms including -S-CH=CH-, or an alkenylene group with a total of 2 to 6 carbon atoms including -S-CH=CH-, ２ -CH ２ A alkylene group with a total of 2 to 6 carbon atoms, including -, is preferred. ４１’ The alkylene group or alkenylene group that can be used as above includes cases where these groups have a bond*, R ４１ It can be taken as -S-CH ２ -CH ２ This is the same as an alkylene group with a total of 2 to 6 carbon atoms including - or an alkenylene group with a total of 2 to 6 carbon atoms including -S-CH=CH-.

[0072] The group represented by the general formula (4') is Ar ４１’ and R ４１’ Examples of groups obtained by appropriately combining the above include the preferred Ar ４１’ and preferred R ４１’ A group combining Ar is preferred. ４１’ A phenyl group which may have substituents, and R ４１’ as -S-CH ２ -CH ２ A group that combines an alkylene group containing - is more preferable.

[0073] In general formula (4'), *- represents the above Ar ４１’ As shown, in the present invention, Ar ４１’ or R ４１’ The carbon atoms that make up the and Z in general formula (1) or (1') １１ This represents a coupling that joins two things together.

[0074] In the general formula (5'-1), Ar ５１１’ and Ar ５１２’ This is Ar in general formula (5-1) ５１１ and Ar ５１２A preferred embodiment is one in which each independently represents a phenyl group which may have substituents or a monocyclic aromatic heterocyclic group, and a phenyl group which may have substituents is preferred. ５１１’ and Ar ５１２’ They may be the same or different from each other, but it is preferable that they be the same.

[0075] In the general formula (5'-1), R ５１１ and R ５１２ Each of these independently represents a single bond or an alkylene group having 1 to 4 carbon atoms. R in general formula (5'-1) ５１１ and R ５１２ These are, respectively, R in general formula (5-1). ５１１ and R ５１２ It is the same as this.

[0076] In the general formula (5'-1), A ５１ represents an oxygen atom, a sulfur atom, or a carbonyl group, and A in general formula (5-1) ５１ It is the same as this.

[0077] The group represented by the general formula (5'-1) is Ar ５１１’ and Ar ５１２’ and R ５１１ and R ５１２ and A ５１ Examples of groups obtained by appropriately combining the above include the preferred Ar ５１１’ and Ar ５１２’ and preferred R ５１１ and R ５１２ And a favorable A ５１ A base combining the two is preferable.

[0078] In the general formula (5'-1), *- represents Ar ５１１’ The carbon atoms that make up the and Z in general formula (1) or (1') １１ This represents a coupling that joins two things together.

[0079] In the general formula (5'-2), Ar ５２１’ and Ar ５２２’ Ar in general formula (5-2) ５２１ and Ar ５２２A preferred embodiment is one in which each independently represents a phenyl group or a monocyclic aromatic heterocyclic group which may have substituents. ５２１’ and Ar ５２２’ They may be the same or different from each other. However, Ar ５２１’ and Ar ５２２’ In Ar ５２１’ The carbon atoms constituting the above phenyl group or monocyclic aromatic heterocyclic group that can be taken as Ar ５２２’ Among the carbon atoms constituting the above phenyl group or monocyclic aromatic heterocyclic group that can be taken as, Ar in general formula (5'-2) ５２１’ -C(=O)-Ar ５２２’ The carbon atoms involved in the bonding, i.e., the carbon atoms bonded to the carbonyl carbon atom, may also be bonded to each other at their α-positions. The bond between the α-position carbon atoms mentioned above is indicated by a dashed line in general formula (5'-2).

[0080] In the general formula (5'-2), *- represents Ar ５２１’ The carbon atoms that make up the and Z in general formula (1) or (1') １１ This represents a coupling that joins two things together.

[0081] <Group C> R １３ The group C that can be used is a group having an aromatic hydrocarbon ring group or an aromatic heterocyclic group and a conjugated bond group that forms a continuous conjugated system with this ring group. In this invention, group C may be conveniently referred to as a "conjugated bond group-containing aromatic ring group." Also, in the description of group C, both the aromatic hydrocarbon ring group and the aromatic heterocyclic group constituting group C may be collectively referred to simply as an "aromatic ring group." １３ The aromatic hydrocarbon ring group constituting the conjugated bond-containing aromatic ring group that can be taken as is not particularly limited, Ar １１ ~Ar １３ A phenyl group is preferred, which is the same as the aromatic hydrocarbon ring group that constitutes the compound, but may have substituents. １３ The aromatic heterocyclic group constituting the conjugated bond-containing aromatic ring group that can be taken as is not particularly limited, R １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３It is the same as an aromatic heterocyclic group. １３ The conjugated bond group that constitutes the conjugated aromatic ring group can be any group that forms a conjugated system with the aromatic ring group when directly bonded to the aromatic ring group, and examples include unsaturated aliphatic hydrocarbon groups. The unsaturated aliphatic hydrocarbon group is not particularly limited and examples include groups consisting of alkenes, alkynes, conjugated polyenes, etc. Examples of alkenes and alkynes include alkenes and alkynes that form alkenyl groups and alkynyl groups in substituent Z described later. Examples of conjugated polyenes include compounds in which double or triple bonds and single bonds are alternately linked, and may have a branched structure or a cyclic structure, but it is generally preferable to have a linear structure. Examples of such polyenes include diene compounds such as 1,3-butadiene and triene compounds. One preferred embodiment is that the conjugated bond group is a group other than the aromatic hydrocarbon ring group and aromatic heterocyclic group that constitute the conjugated aromatic ring group (a group other than an aromatic ring group).

[0082] The total number of aromatic ring groups and conjugated bonds constituting the conjugated group-containing aromatic ring group is not particularly limited and can be, for example, 2 to 4. The conjugated group-containing aromatic ring group may have groups other than the above aromatic ring group and other than conjugated bonds, but it is preferable that it is formed of the above aromatic ring group and the above conjugated bonds. In this case, the conjugated group-containing aromatic ring group is formed of either the above aromatic ring group or the above conjugated bonds Z １１ It may also be bonded to a conjugated group. Examples of aromatic ring groups containing a conjugated group include a group in which an aromatic ring group and a conjugated group are bonded in this order, and a group in which an aromatic ring group, a conjugated group, and an aromatic ring group are bonded in this order. １３ The conjugated group-containing aromatic ring group that can be used may have substituents on the aromatic ring group, the conjugated group, or any other group. The substituents that the conjugated group-containing aromatic ring group may have are not particularly limited and include any group selected from substituent Z described later.

[0083] R １３Examples of compounds having a C group (1) include the compounds synthesized in the examples, but the present invention is not limited to these compounds.

[0084] R １３ Among the above groups A to C, it is preferable that the group is either group A or any of the above general formulas (3) to (6-2), as it can achieve a high level of both thermal potential and UV sensitivity. It is more preferable that the group is any of the above general formulas (3) to (6-2). The preferred groups of group A and any of the above general formulas (3) to (6-2) are as described for each group.

[0085] [R １１ and R １２ In general formula (1), R １１ and R １２ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. The carbon chain structure of the alkyl group having 1 to 4 carbon atoms is not particularly limited and may be a linear, branched, or cyclic structure. The alkyl group preferably has 1 or 2 carbon atoms. １１ and R １２ These are preferably hydrogen atoms or methyl groups, and they may be the same or different from each other. １１ and R １２ Preferred combinations include combinations of hydrogen atoms, combinations of methyl groups, and combinations of hydrogen atoms and methyl groups.

[0086] [Z １１ In general formula (1), Z １１ This represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.

[0087] [m1 and n1] In general formula (1), m1 represents 0 or 1, and when n1 below is 0, m1 represents 0. In general formula (1), n1 represents an integer from 0 to 4, and 1 or 2 is preferred. In the present invention, m1 and n1 can be combined as appropriate, and it is preferable to combine m1 with n1 within a preferred range, for example, the combination m1=0, n1=1, the combination m1=n1=1, and the combination m1=n1=0 are more preferred.

[0088] [p1] In general formula (1), p1 represents 0 or 1. Compound (1) has a sensitizing group R when p1 is 0. １３ Alcolate having and a group 13 element X having three substituted aromatic hydrocarbon ring groups １１ The compound has an art complex with the counteranion, and when p1 is 1, the sensitizing group R １３ A carboxylate having three substituted aromatic hydrocarbon ring groups, and a Group 13 element X １１ These compounds have an ate complex with a counteranion. All of these compounds exhibit excellent thermal latent properties and high UV sensitivity. It is preferable that p1 is 1 in order to exhibit a well-balanced combination of thermal latent properties and UV sensitivity at an even higher level.

[0089] [X １１ In general formula (1), X １１ This represents a boron atom, an aluminum atom, a gallium atom, or an indium atom, and in terms of thermal potential and UV sensitivity, a boron atom or an aluminum atom is preferred, and a boron atom is more preferred.

[0090] [Y １１ In general formula (1), Y １１ represents an organic onium cation. Note that in formula (1), Y １１ Although it is shown in a positively charged state, in the present invention Y １１ In that case, Y １１ It is used to mean including the cation of Y. １１The organic onium cation that can be used is not particularly limited, and those commonly used in photoacid generators can be used. The organic onium cation is preferably selected from, for example, sulfonium cation, iodonium cation, ammonium cation, phosphonium cation, and pyridinium cation, with sulfonium cation and iodonium cation being more preferred. Specifically, the organic onium cation is preferably a cation represented by any of the following general formulas (7) to (11), and more preferably a cation represented by the following general formula (7) or (8).

[0091] <Sulfonium Cation> The sulfonium cation is not particularly limited and may be any that is commonly used in photoacid generators, but it is preferably a sulfonium cation represented by the following general formula (7).

[0092] In general formula (7), R ７１ This is an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, a group represented by the following general formula (12), or a group represented by the following general formula (13). ７１ Among the above groups, an aromatic hydrocarbon ring group or an aromatic heterocyclic ring group, which may have substituents, is preferred.

[0093] R ７１ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, for example, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, but R ７１ A substituent that may be present on the aromatic hydrocarbon ring group or aromatic heterocyclic group constituting the group is Ar ３１The same embodiments as substituents that may be present on an aromatic hydrocarbon ring group or aromatic heterocyclic group constituting the Ar ３１ Among the substituents that may be present on the aromatic hydrocarbon ring group or aromatic heterocyclic group constituting the aromatic hydrocarbon ring group, the -S-Ar substituents described later are ７１ This includes both embodiments in which the substituent is other than the above.

[0094] R ７１ Possible substituents include -S-Ar ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, a group represented by general formula (12), or a group represented by general formula (13). The group is not particularly limited. ７１ The aromatic hydrocarbon ring group and aromatic heterocyclic group that constitute the above group are not particularly limited, and the substituent Z may be present on the condensed polycyclic group constituting group A. Ｒ１３ The rings are the same as those that form aromatic hydrocarbon ring groups and aromatic heterocyclic ring groups as described above. However, R ７１ As such, an aromatic hydrocarbon ring group is preferred, and a monocyclic aromatic hydrocarbon ring group is more preferred. -S-Ar as a substituent that the above aromatic hydrocarbon ring group and aromatic heterocyclic group may have. ７１ In Ar ７１ Ar represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, a group represented by the following general formula (12), or a group represented by the following general formula (13). ７１ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, for example, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. The group represented by the following general formula (12) and the group represented by the following general formula (13) are not particularly limited, R ７１ These are the same as the group represented by general formula (12) and general formula (13), which will be described later.

[0095]

[0096] In general formula (12), Ar １２１ and Ar １２２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, and R １２１ and R １２２ Each of these independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, A １２１ R represents a single bond, oxygen atom, sulfur atom, or carbonyl group. １２１ , R １２２ and A １２１ None of them form a single bond, and *- represents Ar １２１ The carbon atoms and cation atoms or -S-Ar that make up the structure ７１ (Ar ７１ As described above, it represents the bond between the S of the group represented by (12). １２１ and Ar １２２ , R １２１ and R １２２ , and A １２１ These are, respectively, Ar in the general formula (5-1) described above. ５１１ and Ar ５１２ , R ５１１ and R ５１２ , and A ５１ It is preferable that it be the same as. In general formula (12), *- is Ar １２１ The carbon atoms that make up the compound, and -S-Ar as a cation atom or substituent in the general formula. ７１ This represents a bond that connects the S of the group represented by the formula (12). Preferably, the group represented by general formula (12) is the same as the group represented by general formula (5-1) described above.

[0097] In general formula (13), Ar １３１ and Ar １３２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents. Ar in general formula (13) １３１ and Ar １３２ These are, respectively, Ar in general formula (5-2). ５２１ and Ar ５２２ It is preferable that it be the same as Ar １３１ and Ar １３２In Ar １３１ A carbon atom constituting an aromatic hydrocarbon ring group or aromatic heterocyclic group that can be taken as, and Ar １３２ Among the carbon atoms constituting the aromatic hydrocarbon ring group or aromatic heterocyclic group that can be taken as, Ar in general formula (13) １３１ -C(=O)-Ar １３２ The carbon atoms involved in the bonding, i.e., the carbon atoms bonded to the carbonyl carbon atom, may be bonded to each other at their α-positions. The above bond between α-position carbon atoms is indicated by a dashed line in general formula (13). In general formula (13), *- represents Ar １３１ The constituent carbon atoms and -S-Ar as a cation atom or substituent ７１ This represents a bond between the group represented by the formula and the group represented by the formula S. Preferably, the group represented by general formula (13) is the same as the group represented by general formula (5-2) described above.

[0098] In general formula (7), R ７２ and R ７３ Each of these is independently an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, a group represented by general formula (12), a group represented by general formula (13), an alkyl group having 1 to 20 carbon atoms which may have substituents, or -CH ２ -Ar ７２ The group represented by (Ar ７２ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. ７２ and R ７３ Each of these is an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, a group represented by general formula (12) is preferred.

[0099] R ７２ and R ７３This may take the form of an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, the groups represented by general formula (12) and general formula (13) are not particularly limited, for example, R ７１ This may take the form of an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, it is the same as the group represented by general formula (12) and the group represented by general formula (13).

[0100] R ７２ and R ７３ The alkyl group having 1 to 20 carbon atoms that may have substituents is not particularly limited, for example, R １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３ It is the same as an alkyl group having 1 to 20 carbon atoms.

[0101] R ７２ and R ７３ It can be taken as -CH ２ -Ar ７２ The group represented by (Ar ７２ Ar represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. The Ar is not particularly limited. ７２ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, for example, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents.

[0102] R ７１ ~R ７３In this case, if two or more of them are, respectively, an aromatic hydrocarbon ring group (with or without substituents), an aromatic heterocyclic group (with or without substituents), a group represented by general formula (12), and a group represented by general formula (13), then in two adjacent groups, the carbon atoms at the α-position of the carbon atoms involved in the bonding of the sulfur atom (cation) in general formula (7) among the carbon atoms constituting the aromatic hydrocarbon ring group, aromatic heterocyclic group, group represented by general formula (12), and group represented by general formula (13) may be bonded via a heteroatom or an alkyl group having 1 to 6 carbon atoms, or they may be directly bonded. The heteroatom that bonds the carbon atoms at the α-position is not particularly limited and includes, for example, nitrogen atoms, oxygen atoms, sulfur atoms, phosphorus atoms, etc. Note that atoms with polyvalent valencies, such as nitrogen atoms and phosphorus atoms, may have substituents to satisfy a predetermined valency. Examples of such substituents include each group selected from substituent Z described later, and preferably include alkyl groups, aryl groups, heterocyclic groups, etc. The alkyl group having 1 to 6 carbon atoms is not particularly limited; for example, other than the number of carbon atoms, R １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３ It is the same as an alkyl group having 1 to 20 carbon atoms. The number of carbon atoms in an alkyl group having 1 to 6 carbon atoms is preferably 1 to 4, and more preferably 1 or 2.

[0103] R ７１ and R ７２ and R ７３ The combinations are not particularly limited, and the above groups can be combined as appropriate, R ７１ The above group is preferred as R ７２ and R ７３ A combination with the above preferred group is preferred. ７１ and R ７２ and / or R ７３ They may be the same or they may be different. Also, R ７２ and R ７３They may be the same or different. The sulfonium cation represented by general formula (7) may be an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ If the group has an aromatic hydrocarbon ring group or an aromatic heterocyclic group, a group represented by general formula (12), or a group represented by general formula (13), these groups are R ７１ ~R ７３ It can be interpreted in either way, but R ７１ , R ７２ and / or R ７３ It is preferable to interpret (attribute) them in the following order of priority.

[0104] Suitable sulfonium cations (including sulfonium cations represented by general formula (7)) include the cations used in the examples and the cations shown below, but the present invention is not limited to these. In the cations shown below, R represents a substituent. In addition to these cations, other sulfonium cations include, for example, those described in International Publication No. 2021 / 053993 and Japanese Patent Application Publication No. 2019-183048, and the contents described in both publications are incorporated as part of this specification.

[0105] <Iodonium Cation> The iodonium cation is not particularly limited and may be any that is commonly used in photoacid generators, but it is preferably an iodonium cation represented by the following general formula (8).

[0106] In general formula (8), R ８１ and R ８２ Each of these is independently an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, it represents a group represented by general formula (12) or general formula (13). ８１ and R ８２Among the above groups, each is preferably an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents.

[0107] R ８１ and R ８２ This may take the form of an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, the group represented by general formula (12) and the group represented by general formula (13) are R ７１ This may take the form of an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, it is the same as the group represented by general formula (12) and the group represented by general formula (13).

[0108] R ８１ and R ８２ However, if each of these is an aromatic hydrocarbon ring group (with or without substituents), an aromatic heterocyclic group (with or without substituents), a group represented by general formula (12), or a group represented by general formula (13), then in two adjacent groups, the carbon atoms at the α-position of the carbon atoms involved in the bonding of the iodine atom (cation) in general formula (8) among the carbon atoms constituting the aromatic hydrocarbon ring group, aromatic heterocyclic group, group represented by general formula (12), and group represented by general formula (13) may be bonded via a heteroatom or an alkyl group having 1 to 6 carbon atoms, or they may be directly bonded. ８１ and R ８２ The heteroatoms and C1-C6 alkyl groups that bond carbon atoms together are R ７１ ~R ７３ These are the same heteroatoms and C1-C6 alkyl groups that bond carbon atoms at the α-position, as explained earlier.

[0109] R ８１ and R ８２ The combination is not particularly limited, and the above groups can be combined as appropriate, R ８１The above group is preferred as R ８２ A combination with the above preferred group is preferred. ８１ and R ８２ They may be the same or they may be different.

[0110] Suitable iodonium cations (including iodonium cations represented by general formula (8)) include the cations used in the examples and the cations shown below, but the present invention is not limited to these. In addition to these cations, other iodonium cations include, for example, those described in International Publication No. 2021 / 053993 and Japanese Patent Application Publication No. 2019-183048, and the contents described in both publications are incorporated as part of this specification.

[0111] <Ammonium Cation> The ammonium cation is not particularly limited and may be any ammonium cation commonly used in photoacid generators, but it is preferably an ammonium cation represented by the following general formula (9).

[0112] In general formula (9), R ９１ This is an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, the group represented by general formula (12), the group represented by general formula (13), or -CH ２ -Ar ７２ The group represented by (Ar ７２ As stated above, R ９２ ~R ９４ Each of these is independently an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, an alkyl group having 1 to 20 carbon atoms which may have substituents, or -CH ２ -Ar ７２ The group represented by (Ar ７２ As stated above, it represents R. ９１ Among the above groups, this may be an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, or -CH ２ -Ar７２ The group represented by (Ar ７２ As stated above. ) is preferable. R ９２ ~R ９４ Each of these is preferably an alkyl group having 1 to 20 carbon atoms, which may have substituents.

[0113] R ９１ This may take the form of an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, the groups represented by general formula (12) and general formula (13) are not particularly limited, for example, R ７１ This may take the form of an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, ), is the same as the group represented by general formula (12) and the group represented by general formula (13). Also, R ９１ It can be taken as -CH ２ -Ar ７２ The group represented by (Ar ７２ As stated above, ) is not particularly limited, for example, R ７２ and R ７３ It can be taken as -CH ２ -Ar ７２ It is the same as the base represented by .

[0114] R ９２ ~R ９４ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, for example, R ７１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents. ９２ ~R ９４ The alkyl group having 1 to 20 carbon atoms that may have substituents is not particularly limited, for example, R １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３It is the same as an alkyl group having 1 to 20 carbon atoms. ９２ ~R ９４ It can be taken as -CH ２ -Ar ７２ The base represented by is not particularly limited; for example, R ７２ and R ７３ It can be taken as -CH ２ -Ar ７２ It is the same as the base represented by .

[0115] R ９１ and R ９２ ~R ９４ The combinations are not particularly limited, and the above groups can be combined as appropriate, R ９１ The above group is preferred as R ９２ ~R ９４ A combination with the above preferred group is preferred. ９１ and R ９２ ~R ９４ Any or all of them may be the same or different. Also, R ９２ ~R ９４ All of these may be the same or different. The ammonium cation represented by general formula (9) may be an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, -CH ２ -Ar ７２ The group represented by (Ar ７２ As stated above.) If these groups have R ９１ ~R ９４ It can be interpreted in either way, but R is preferred. ９１ It is preferable to interpret (attribute) it as follows.

[0116] As ammonium cations (including ammonium cations represented by general formula (9)), the cations used in the examples are preferred, but the present invention is not limited to these. Examples of ammonium cations other than those used in the examples are those described in International Publication No. 2021 / 053993 and Japanese Patent Application Publication No. 2019-183048, and the contents described in both publications are incorporated as is as part of this specification.

[0117] <Phosphonium Cation> The phosphonium cation is not particularly limited and may be any phosphonium cation commonly used in photoacid generators, but it is preferably a phosphonium cation represented by the following general formula (10).

[0118] In general formula (10), R １０１ This is an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, the group represented by general formula (12), the group represented by general formula (13), or -CH ２ -Ar ７２ The group represented by (Ar ７２ As stated above, R １０２ ~R １０４ Each of these is independently an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, an alkyl group having 1 to 20 carbon atoms which may have substituents, or -CH ２ -Ar ７２ The group represented by (Ar ７２ As stated above, it represents R. １０１ Among the above groups, -CH ２ -Ar ７２ The group represented by (Ar ７２ As stated above. ) is preferable. R １０２ ~R １０４ These are preferably aromatic hydrocarbon ring groups or aromatic heterocyclic groups, which may each have substituents.

[0119] R １０１ This may take the form of an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, the groups represented by general formula (12) and general formula (13) are not particularly limited, for example, R ７１ This may take the form of an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, ), is the same as the group represented by general formula (12) and the group represented by general formula (13). Also, R １０１ It can be taken as -CH ２ -Ar ７２ The group represented by (Ar ７２ As stated above, ) is not particularly limited, for example, R ７２ and R ７３ It can be taken as -CH ２ -Ar ７２ It is the same as the base represented by .

[0120] R １０２ ~R １０４ The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, for example, R ７１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents. １０２ ~R １０４ The alkyl group having 1 to 20 carbon atoms that may have substituents is not particularly limited, for example, R １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３ It is the same as an alkyl group having 1 to 20 carbon atoms. １０２ ~R １０４ It can be taken as -CH ２ -Ar ７２ The base represented by is not particularly limited; for example, R ７２ and R ７３ It can be taken as -CH ２ -Ar ７２ It is the same as the base represented by .

[0121] R １０１ and R １０２ ~R １０４ The combinations are not particularly limited, and the above groups can be combined as appropriate, R １０１ The above group is preferred as R １０２ ~R １０４ A combination with the above preferred group is preferred. １０１ and R１０２ ~R １０４ Any or all of them may be the same or different. Also, R １０２ ~R １０４ All of them may be the same or different. The phosphonium cation represented by general formula (10) may be an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, -CH ２ -Ar ７２ If the group represented by R is present, these groups are R １０１ ~R １０４ It can be interpreted in either way, but R is preferred. １０１ It is preferable to interpret (attribute) it as follows.

[0122] The phosphonium cations (including phosphonium cations represented by general formula (10)) used in the examples are preferred, but the present invention is not limited to these. Other phosphonium cations besides those used in the examples include those described in International Publication No. 2021 / 053993 and Japanese Patent Application Publication No. 2019-183048, and the contents of both publications are incorporated as is as part of this specification.

[0123] <Pyridinium Cation> The pyridinium cation is not particularly limited and can be any that is commonly used in photoacid generators, but it is preferably a pyridinium cation represented by the following general formula (11).

[0124] In general formula (11), R １１１ This is an alkyl group having 1 to 20 carbon atoms, which may have substituents, or -CH ２ -Ar １１１ The group represented by (Ar １１１ ) represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. １１２ ~R １１６ Each of these independently comprises a hydrogen atom, a C1-C20 alkyl group which may have substituents, a halogen group, a hydroxyl group, a sulfo group, a nitro group, a carboxyl group, a cyano group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and -CH ２ -Ar１１１ The group represented by (Ar １１１ As stated above, ), or -(C=O)-R １１７ The group represented by (R １１７ R represents a C1-C10 alkyl group which may be branched, or an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. １１１ Among the above groups, -CH ２ -Ar １１１ The group represented by (Ar １１１ As stated above. ) is preferable. R １１２ ~R １１６ These are preferably a hydrogen atom, a carboxyl group, and a cyano group, respectively.

[0125] R １１１ The alkyl group having 1 to 20 carbon atoms that may have substituents is not particularly limited, for example, R １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３ It is the same as an alkyl group having 1 to 20 carbon atoms. Also, R １１１ It can be taken as -CH ２ -Ar １１１ The group represented by (Ar １１１ As stated above, ) is not particularly limited, for example, R ７２ and R ７３ It can be taken as -CH ２ -Ar ７２ The group represented by (Ar ７２ It is the same as above.

[0126] R １１２ ~R １１６ The alkyl group having 1 to 20 carbon atoms that may have substituents is not particularly limited, for example, R １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３ It is the same as an alkyl group having 1 to 20 carbon atoms. １１２ ~R １１６The halogen group that can be used is not particularly limited, and examples include halogen atoms, among which fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc. are preferred, and fluorine atoms are more preferred. １１２ ~R １１６ The aromatic hydrocarbon ring group and aromatic heterocycle that can be used as such are not particularly limited, and for example, substituent Z may be present on the condensed polycyclic group constituting group A. Ｒ１３ The rings are the same as those that form aromatic hydrocarbon ring groups and aromatic heterocyclic ring groups as described above. However, R １１２ ~R １１６ As such, an aromatic hydrocarbon ring group is preferred, and a monocyclic aromatic hydrocarbon ring group is more preferred. １１２ ~R １１６ It can be taken as -CH ２ -Ar １１１ The group represented by (Ar １１１ As stated above, ) is not particularly limited, for example, R ７２ and R ７３ It can be taken as -CH ２ -Ar ７２ The group represented by (Ar ７２ It is the same as above.

[0127] R １１２ ~R １１６ It can be taken as -(C=O)-R １１７ The group represented by (R １１７ R represents a C1-C10 alkyl group which may be branched, or an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. The R is not particularly limited. １１７ The branched alkyl group having 1 to 10 carbon atoms that can be used as is not particularly limited, for example, other than the number of carbon atoms, １３ Substituents Z may be present on the fused polycyclic group constituting group A, which can be taken as such. Ｒ１３ It is the same as an alkyl group having 1 to 20 carbon atoms. １１７ The number of carbon atoms in the alkyl group that can be used is preferably 1 to 5, and more preferably 1 or 2. １１７The aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents is not particularly limited, for example, Ar ３１ It is the same as an aromatic hydrocarbon ring group or aromatic heterocyclic group that may have substituents.

[0128] R １１１ and R １１２ ~R １１６ The combinations are not particularly limited, and the above groups can be combined as appropriate, R １１１ The above group is preferred as R １１２ ~R １１６ A combination with the above preferred group is preferred. １１１ and R １１２ ~R １１６ Any or all of them may be the same or different. Also, R １１２ ~R １１６ They may all be the same or they may all be different.

[0129] Examples of pyridinium cations (including pyridinium cations represented by general formula (11)) include those described in International Publication No. 2021 / 053993 and Japanese Patent Publication No. 2019-183048, and the contents described in both publications are incorporated as is as part of this specification.

[0130] [Scope of Compound (1)] Compound (1) represented by general formula (1) can be any combination of groups or atoms etc. represented by each symbol in general formula (1) as described above. <Combinations of each symbol in the counter anion> First, the combinations of each symbol in the counter anion that constitute compound (1) will be explained. In general formula (1), the combination of each symbol in the counter anion is not particularly limited, and groups or atoms etc. represented by each symbol can be any combination as appropriate, preferably Ar １１ ~Ar １３ , R １３ , R １１ , R １２ Z １１ , m1, n1, p1, X １１Each of the desirable elements can be combined. For example, in terms of achieving a better balance between thermal potential and UV sensitivity at an even higher level, R １３ X is a group represented by any of the above general formulas (3) to (6-2), １１ is a boron atom and Ar １１ ~Ar １３ A combination in which the same group is preferred, and in this preferred combination, the other groups or atoms represented by the symbols can be combined as appropriate. In general formula (1) and the above preferred combination, Ar １１ ~Ar １３ Each of these is more preferably independently a halogeno group and a phenyl group having at least one C1-C4 alkyl group containing a fluorine atom as substituents. In general formula (1) and the above preferred combinations, R １３ It is more preferable that the group is represented by the above general formula (4), (5-1), or (5-2), and even more preferable that the group is represented by the above general formula (4'), (5'-1), or (5'-2). Furthermore, as the group represented by general formula (1) and general formula (4) in the above preferred combinations, R ４１ ga-S-CH ２ -CH ２ It is an alkylene group containing - or an alkenylene group containing -S-CH=CH-, Ar ４１ It is preferable that is a phenyl group which may have substituents. Furthermore, the group represented by general formula (1) and general formula (5-1) in the above preferred combination is Ar ５１１ and Ar ５１２ However, each is preferably independently a phenyl group or a monocyclic aromatic heterocyclic group which may have substituents, and the group represented by the general formula (5-2) in the above preferred combination is Ar ５２１ and Ar ５２２ However, each is preferably independently a phenyl group that may have substituents or a monocyclic aromatic heterocyclic group.

[0131] In the above preferred combinations, the groups or atoms represented by each symbol can be combined as appropriate, and combinations corresponding to the counter anions in the compound represented by the general formula (1') described later are particularly preferred.

[0132] <Combinations of symbols in organo-onium cations> In general formula (1), organo-onium cations that are commonly used in photoacid generators can be used. Therefore, the combinations of symbols in general formulas (7) to (11) are not particularly limited, and groups or atoms represented by each symbol can be combined as appropriate. As described above, it is preferable to combine preferred groups or atoms represented by each symbol.

[0133] <Combination of counter anion and organo-onium cation> In general formula (1), the combination of counter anion and organo-onium cation is not particularly limited, and the counter anion and organo-onium cation can be combined as appropriate. It is preferable to combine a preferred counter anion with a preferred organo-onium cation, and the combination of counter anion and organo-onium cation in the compound represented by general formula (1') described later is more preferable.

[0134] However, in general formula (1), R １３ However, R is a condensed polycyclic aromatic heterocyclic group, a group having an aromatic ketone skeleton, or an aromatic ring group containing a conjugated bond. １３ One of the bonds between the heteroatoms that make up the Z １１ When representing a bond with (the above one heteroatom is Z) １１ (In the case of a coupling with R), that is, １３ However, one of the bonds of the heteroatom is adjacent to Z １１ In cases where the bonding portion with is a condensed polycyclic aromatic heterocyclic group, a group having an aromatic ketone skeleton, or an aromatic ring group containing a conjugated bond, the embodiments in which m1 = n1 = 0 and the embodiments in which m1 = 1 are excluded. That is, R １３ When taking one of the three groups described above, Z in each group １１ If the bond position is a heteroatom, then this heteroatom is -(C=O) in general formula (1)ｐ１ A configuration in which the atoms bond directly to -O- (m1=n1=0), and Z １１ Compounds included in the two embodiments, including the embodiment in which direct bonding occurs (m1=1), are excluded from compound (1) of the present invention. This is because these compounds are presumed not to exhibit excellent thermal latent properties, and are also presumed to easily generate gases (e.g., carbon dioxide) upon light irradiation, which may degrade the properties of the cured product.

[0135] <Compound represented by general formula (1')> A preferred compound of compound (1) of the present invention is compound (1') represented by the following general formula (1'). In the present invention, when simply referring to the compound of the present invention and compound (1), it means that it includes the preferred compound (1').

[0136] (Ar １１’ ~Ar １３’ ) In general formula (1'), Ar １１’ ~Ar １３’ Each independently represents a halogen group and a phenyl group having at least one C1-C4 alkyl group containing a fluorine atom as substituents, and Ar １１’ ~Ar １３’ These are the same group. Ar in general formula (1') １１’ ~Ar １３’ This is Ar in the general formula (1) above. １１ ~Ar １３ A preferred form is in which the substituted aromatic hydrocarbon ring group is a phenyl group and Ar １１’ ~Ar １３’ Except that they are the same group, Ar in general formula (1) １１ ~Ar １３ It is the same as this.

[0137] (R １３’ ) In general formula (1'), R １３’ R represents the group shown in the following general formulas (4'), (5'-1), or (5'-2). １３’ R in the above general formula (1) is １３ This is a preferred form, and R in general formula (1) １３ This is limited to preferred groups B that can be used as such.

[0138] In general formula (4'), Ar ４１’ Ar represents a phenyl group which may have substituents. In general formula (4'), Ar ４１’ This is Ar in the general formula (4) above. ４１ A preferred form is the Ar in general formula (4), except that the substituted aromatic hydrocarbon ring group is a phenyl group. ４１ It is the same as. In general formula (4'), R ４１’ is, -S-CH ２ -CH ２ R in general formula (4') represents an alkylene group with a total of 2 to 6 carbon atoms including - or an alkenylene group with a total of 2 to 6 carbon atoms including -S-CH=CH-. ４１’ R in the above general formula (4) is ４１ This is a preferred form, and R in general formula (4) ４１ -S-CH is preferably adopted as ２ -CH ２ Except for limiting it to alkylene groups with a total of 2 to 6 carbon atoms including - or alkenylene groups with a total of 2 to 6 carbon atoms including -S-CH=CH-, the R in general formula (4) ４１ It is the same as above. In general formula (4'), *- represents Ar ４１’ As shown, in the present invention, Ar ４１’ or R ４１’ The carbon atoms that make up the and Z in general formula (1') １１ This represents a coupling that joins two things together.

[0139] In the general formula (5'-1), Ar ５１１’ and Ar ５１２’ Each of these independently represents an optionally substituted phenyl group or an optionally substituted monocyclic aromatic heterocyclic group. Ar in general formula (5'-1) ５１１’ and Ar ５１２’ This is Ar in the general formula (5-1) above. ５１１ and Ar ５１２ This is a preferred form of Ar ５１１ and Ar ５１２ The aromatic hydrocarbon ring group in Ar is limited to a phenyl group, ５１１and Ar ５１２ Ar in the general formula (5-1) is the same as Ar in the general formula (5-1), except that the aromatic heterocyclic group in ５１２ is limited to a monocyclic aromatic heterocyclic group ５１１ and Ar ５１２ are the same. In the general formula (5'-1), R ５１１ and R ５１２ each independently represent a single bond or an alkylene group having 1 to 4 carbon atoms, and A ５１ represents a single bond, an oxygen atom, a sulfur atom or a carbonyl group. However, none of R ５１１ , R ５１２ and A ５１ will be a single bond. R ５１１ and R ５１２ in the general formula (5'-1), and A ５１ are the same as Ar ５１１ and Ar ５１２ in the above general formula (5-1), and A ５１ . In the general formula (5'-1), *- represents a bond connecting the carbon atom constituting Ar ５１１’ and Z １１ in the general formula (1').

[0140] In the general formula (5'-2), Ar ５２１’ and Ar ５２２’ each independently represent a phenyl group which may have a substituent or a monocyclic aromatic heterocyclic group which may have a substituent. Ar ５２１’ and Ar ５２２’ in the general formula (5'-2) are the preferred forms of Ar ５２１ and Ar ５２２ in the above general formula (5-2), and the aromatic hydrocarbon ring group in Ar ５２１ and Ar ５２２ is limited to a phenyl group, and Ar ５２１ and Ar ５２２ are the same as Ar ５２１ and Ar ５２２ in the general formula (5-2), except that the aromatic heterocyclic group in Ar ５２１’ and Ar ５２２’ is limited to a monocyclic aromatic heterocyclic group. In Ar ５２１’The carbon atoms constituting the phenyl group or monocyclic aromatic heterocyclic group that can be taken as, and Ar ５２２’ Among the carbon atoms constituting the phenyl group or monocyclic aromatic heterocyclic group that can be taken as, Ar in the general formula (5'-2) ５２１’ -C(=O)-Ar ５２２’ It is also possible that the carbon atoms at the α-position of the carbon atoms involved in the bond of may be bonded to each other. Ar in the general formula (5-2) ５２１ and Ar ５２２ are the same. In the general formula (5'-2), *- represents a bond that connects the carbon atoms constituting Ar ５２１’ and Z in the general formula (1') １１ .

[0141] (R １１ and R １２ ) R in the general formula (1') １１ and R １２ are the same as R in the general formula (1) １１ and R １２ . (Z １１ ) Z in the general formula (1') １１ is the same as Z in the general formula (1) １１ . (m1 and n1) m1 and n1 in the general formula (1') are the same as m1 and n1 in the general formula (1). (p1) p1 in the general formula (1') is the same as p1 in the general formula (1).

[0142] (X １１’ ) In the general formula (1'), X １１’ represents a boron atom. X in the general formula (1') １１’ is a preferred form of X in the above general formula (1), and is the same as X in the general formula (1) except that it can only take a boron atom １１ . １１

[0143] (Y １１’ ) In the general formula (1'), Y １１’ represents a group represented by the following general formula (7) or (8). Y in the general formula (1') １１’ is a preferred form of Y in the above general formula (1), and Y in the general formula (1) １１ ​​１１ This is limited to preferred organoonium cations that can be taken as such. In general formula (1'), Y １１’ The sulfonium cation represented by the following general formula (7) can be taken as follows, as explained below, in general formula (1), Y １１ This is the same as the sulfonium cation represented by the general formula (7) mentioned above, which can be taken as such.

[0144] In general formula (7), R ７１ This is an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, a group represented by the following general formula (12), or a group represented by the following general formula (13). In general formula (7), R ７２ and R ７３ Each of these is independently an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, a group represented by general formula (12), a group represented by general formula (13), an alkyl group having 1 to 20 carbon atoms which may have substituents, or -CH ２ -Ar ７２ The group represented by (Ar ７２ ) represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents.

[0145] R ７１ ~R ７３In this case, if two or more of them are, respectively, an aromatic hydrocarbon ring group (with or without substituents), an aromatic heterocyclic group (with or without substituents), a group represented by general formula (12), and a group represented by general formula (13), then in two adjacent groups, the carbon atoms at the α-position of the carbon atoms involved in the bonding of the sulfur atom (cation) in general formula (7) among the carbon atoms constituting the aromatic hydrocarbon ring group, aromatic heterocyclic group, group represented by general formula (12), and group represented by general formula (13) may be bonded via a heteroatom or an alkyl group having 1 to 6 carbon atoms, or they may be directly bonded.

[0146]

[0147] In general formula (12), Ar １２１ and Ar １２２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, and R １２１ and R １２２ Each of these independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, A １２１ R represents a single bond, oxygen atom, sulfur atom, or carbonyl group. １２１ , R １２２ and A １２１ None of them form a single bond, and *- represents Ar １２１ The carbon atoms and cation atoms or -S-Ar that make up the structure ７１ This represents a bond that connects the S of the group represented by .

[0148] In general formula (13), Ar １３１ and Ar １３２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents. However, Ar １３１ and Ar １３２ In Ar １３１ A carbon atom constituting an aromatic hydrocarbon ring group or aromatic heterocyclic group that can be taken as, and Ar １３２ Among the carbon atoms constituting the aromatic hydrocarbon ring group or aromatic heterocyclic group that can be taken as, Ar in general formula (13) １３１ -C(=O)-Ar １３２The carbon atoms involved in the bonding, i.e., the carbon atoms bonded to the carbonyl carbon atom, may be bonded to each other at their α-positions. The above bond between α-position carbon atoms is indicated by a dashed line in general formula (13). In general formula (13), *- represents Ar １３１ The constituent carbon atoms and -S-Ar as a cation atom or substituent ７１ This represents a bond between the group represented by and the group represented by S.

[0149] In general formula (1'), Y １１’ The iodonium cation represented by the following general formula (8) can be taken as follows, as explained below, in general formula (1), Y １１ This is the same as the iodonium cation represented by the general formula (8) above, which can be taken as such.

[0150]

[0151] In general formula (8), R ８１ and R ８２ Each of these is independently an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As described above, ) represents a group represented by the above general formula (12), or a group represented by the above general formula (13). R ８１ and R ８２ However, if each of these is an aromatic hydrocarbon ring group (with or without substituents), an aromatic heterocyclic group (with or without substituents), a group represented by general formula (12), or a group represented by general formula (13), then in two adjacent groups, the carbon atoms at the α-position of the carbon atoms involved in the bonding of the iodine atom (cation) in general formula (8) among the carbon atoms constituting the aromatic hydrocarbon ring group, the aromatic heterocyclic group, the group represented by general formula (12), and the group represented by general formula (13) may be bonded via a heteroatom or an alkyl group having 1 to 6 carbon atoms, or they may be directly bonded.

[0152] [Range of Compound (1')] The compound (1') represented by the general formula (1') can appropriately combine groups or atoms represented by each symbol in the above general formula (1').<Combination of Each Symbol in the Counter Anion>In the general formula (1'), the combination of each symbol in the counter anion is not particularly limited, and groups or atoms represented by each symbol can be appropriately combined. Preferably, it is the same as the combination of each symbol in the above counter anion in the general formula (1) within the range that can be taken as groups or atoms represented by each symbol in the general formula (1').<Combination of Each Symbol in the Organic Onnium Cation>In the general formula (1'), since an organic onnium cation that is usually used in a photoacid generator can be used, the combination of each symbol in the general formula (7) or (8) is not particularly limited, and groups or atoms represented by each symbol can be appropriately combined. As described above, it is preferable to combine preferable groups or atoms represented by each symbol.<Combination of the Counter Anion and the Organic Onnium Cation>In the general formula (1'), the combination of the counter anion and the organic onnium cation is not particularly limited, and the counter anion and the organic onnium cation represented by the general formula (7) or (8) can be appropriately combined. It is preferable to combine a preferable counter anion and a preferable organic onnium cation.

[0153] However, in the general formula (1'), R １３ ' has a monocyclic aromatic heterocyclic group which is a bonding portion with Z where one of the bonding hands of the hetero atom is adjacent １１ (when the above one hetero atom is a bonding hand with Z １１ ), the exclusion of the embodiments where m1 = n1 = 0 and the embodiment where m1 = 1 is the same as in the case of the general formula (1).

[0154] The compound of the present invention may further have a substituent in addition to the substituents defined above in its molecular structure. The substituents that the compound of the present invention may further have are not particularly limited, and examples include each group selected from the following substituent Z.

[0155] In general formulas (1) and (1'), when multiple bases are alternatively defined as the bases represented by each symbol, if the scope of a particular base overlaps with the scope of another base, the overlapping portion is preferably included in the earlier base in the order specified in the claims. That is, the base specified later in the claims is the scope excluding the earlier base. Also, in general formulas (1) and (1'), when multiple bases are alternatively defined as the bases represented by each symbol, if a particular specific base is included in multiple alternative bases, it is preferably assigned in the order specified in the claims.

[0156] - Substituent Z - Alkyl group (preferably an alkyl group having 1 to 20 carbon atoms, e.g., methyl, ethyl, isopropyl, t-butyl, pentyl, heptyl, 1-ethylpentyl, benzyl, 2-ethoxyethyl, 1-carboxymethyl, etc.), alkenyl group (preferably an alkenyl group having 2 to 20 carbon atoms, e.g., vinyl, allyl, oleyl, etc.), alkynyl group (preferably an alkynyl group having 2 to 20 carbon atoms, e.g., ethynyl, butadiinyl, phenylethynyl, etc.), cycloalkyl group (preferably a cycloalkyl group having 3 to 20 carbon atoms, e.g., cyclopropyl, cyclopentyl, cyclohexyl In this specification, when alkyl groups are mentioned, they usually include cycloalkyl groups, such as 4-methylcyclohexyl, but are described separately here.), aryl groups (preferably aryl groups having 6 to 26 carbon atoms, for example, phenyl, 1-naphthyl, 4-methoxyphenyl, 2-chlorophenyl, 3-methylphenyl, etc.), heterocyclic groups (preferably heterocyclic groups having 2 to 20 carbon atoms, more preferably 5 or 6-membered heterocyclic groups having at least one oxygen atom, a sulfur atom, or a nitrogen atom as ring constituent atoms. Heterocyclic groups include aromatic heterocyclic groups and aliphatic heterocyclic groups.For example, tetrahydropyran ring group, tetrahydrofuran ring group, 2-pyridyl, 4-pyridyl, 2-imidazolyl, 2-benzoimidazolyl, 2-thiazolyl, 2-oxazolyl, pyrrolidone group, etc.), alkoxy group (preferably an alkoxy group having 1 to 20 carbon atoms, for example, methoxy, ethoxy, isopropyloxy, benzyloxy, etc.), aryloxy group (preferably an aryloxy group having 6 to 26 carbon atoms, for example, phenoxy, 1-naphthyloxy, 3-methylphenoxy, 4-methoxyphenoxy, etc.), heterocyclic oxy group (a group in which an -O- group is bonded to the above heterocyclic group), alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 20 carbon atoms, for example, Ethoxycarbonyl, 2-ethylhexyloxycarbonyl, dodecyloxycarbonyl, etc.), aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 26 carbon atoms, for example phenoxycarbonyl, 1-naphthyloxycarbonyl, 3-methylphenoxycarbonyl, 4-methoxyphenoxycarbonyl, etc.), heterocyclic oxycarbonyl group (a group in which an -O-CO- group is bonded to the above heterocyclic group), amino group, substituted amino group (preferably an alkylamino group having 1 to 20 carbon atoms, or an arylamino group having 6 to 26 carbon atoms, for example N,N-dimethylamino, N,N-diethylamino, N-ethylamino, anilino, etc.), sulfamoyl group (-SO. ２ NH ２), substituted sulfamoyl groups (preferably sulfamoyl groups having 1 to 20 carbon atoms, for example, N,N-dimethylsulfamoyl, N-phenylsulfamoyl, etc.), acyl groups (including alkylcarbonyl groups, alkenylcarbonyl groups, alkynylcarbonyl groups, arylcarbonyl groups, heterocyclic carbonyl groups, preferably acyl groups having 1 to 20 carbon atoms, for example, acetyl, propionyl, butyryl, octanoyl, hexadecanoyl, acryloyl, methacryloyl, crotonoyl, benzoyl, naphthoyl, nicotinoyl, etc.), acyloxy groups (alkylcarbonyloxy groups, This includes alkenylcarbonyloxy groups, alkynylcarbonyloxy groups, and heterocyclic carbonyloxy groups, preferably acyloxy groups having 1 to 20 carbon atoms, such as acetyloxy, propionyloxy, butyryloxy, octanoyloxy, hexadecanoyloxy, acryloyloxy, methacryloyloxy, crotonoyloxy, nicotinoyloxy, etc.), allyloyloxy groups (preferably allyloyloxy groups having 7 to 23 carbon atoms, such as benzoyloxy, naphthoyloxy, etc.), and carbamoyl groups (preferably carbamoyl groups having 1 to 20 carbon atoms, such as N,N-dimethylcarbamoyl, N-phenylcarbamoyl, etc.), acylamino group (preferably an acylamino group having 1 to 20 carbon atoms, e.g., acetylamino, benzoylamino, etc.), alkylthio group (preferably an alkylthio group having 1 to 20 carbon atoms, e.g., methylthio, ethylthio, isopropylthio, benzylthio, etc.), arylthio group (preferably an arylthio group having 6 to 26 carbon atoms, e.g., phenylthio, 1-naphthylthio, 3-methylphenylthio, 4-methoxyphenylthio, etc.), heterocyclic thio group (a group in which an -S- group is bonded to the above heterocyclic group), alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 20 carbon atoms, e.g., methylsulfonyl, ethylsulfonyl, etc.), arylsulfonyl group (preferably an arylsulfonyl group having 6 to 22 carbon atoms) , for example, benzenesulfonyl), alkylsilyl group (preferably an alkylsilyl group having 1 to 20 carbon atoms, for example, monomethylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, etc.), arylsilyl group (preferably an arylsilyl group having 6 to 42 carbon atoms, for example, triphenylsilyl, etc.), alkoxysilyl group (preferably an alkoxysilyl group having 1 to 20 carbon atoms, for example, monomethoxysilyl, dimethoxysilyl, trimethoxysilyl, triethoxysilyl, etc.), aryloxysilyl group (preferably an aryloxysilyl group having 6 to 42 carbon atoms, for example, triphenyloxysilyl, etc.), phosphite group (-OPH(=O)(-OH)), substituted phosphite group (preferably a phosphite group having 1 to 20 carbon atoms, for example, -OP(=O)(-OH)(R, Ｐ )), phosphoryl group (-OPH ２ (=O)), substituted phosphoryl group (preferably a phosphate group having 1 to 20 carbon atoms, for example, -OP(=O)(R Ｐ ) ２ ), phosphonyl group (preferably a phosphonyl group having 1 to 20 carbon atoms, for example, -P(=O)(R Ｐ ) ２ ), phosphenyl group (-PH ２ ), substituted phosphinyl group (preferably a phosphinyl group having 1 to 20 carbon atoms, for example, -P(R Ｐ ) ２ ), phosphonic acid group (-PO(OH) ２), substituted phosphonic acid group (preferably a phosphonic acid group having 1 to 20 carbon atoms, for example, -PO(OR Ｐ ) ２ Examples include sulfo groups (sulfonic acid groups), carboxyl groups, hydroxyl groups, sulfanyl groups, cyano groups, and halogen atoms (e.g., fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.). Ｐ is a substituent (preferably a group selected from substituent Z). Furthermore, each of the groups listed as substituent Z may be further substituted with the substituent Z.

[0157] Among the above, the substituent Z is preferably an alkyl group, alkenyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, heterocyclic oxy group, alkylthio group, arylthio group, heterocyclic thio group, amino group, substituted amino group, carboxyl group, hydroxyl group, cyano group, halogen atom, etc.

[0158] Specific examples of the compounds of the present invention include those synthesized in the examples, but the present invention is not limited to these.

[0159] [Characteristics of the Compound of the Present Invention] The compound of the present invention has the function of generating acid upon irradiation with light, but exhibits a high thermal decomposition temperature and excellent thermal latent properties. Furthermore, because the compound of the present invention has a sensitizing group introduced to the counter anion, it is thought that the transfer of excitation energy to the organo-onium cation can be carried out smoothly, and it exhibits high UV sensitivity compared to systems using a general photoacid generator and sensitizer in combination. Thus, the compound of the present invention combines excellent thermal latent properties with high UV sensitivity. Moreover, the compound of the present invention is not subject to legal regulations at present, there are no major safety concerns, and it can be used in a wide range of applications. In addition, as will be described later, the raw materials for synthesis of the compound of the present invention are readily available, and synthesis is also easy. Although the compound of the present invention exhibits high thermal stability, it can generate active species by heating above the decomposition temperature, and therefore also functions as a thermal acid generator. The conditions under which the compound of the present invention can generate acid are not unique, depending on the type of compound (chemical structure), etc., but for example, the conditions described in the acid generation method of the present invention, which will be described later, can be cited.

[0160] [Synthesis Method of the Compounds of the Present Invention] The compounds of the present invention can be synthesized by various known synthesis methods or in combination thereof. For example, they can be synthesized by appropriately referring to known synthesis methods for photoacid generators, and in particular by referring to the synthesis methods described in the examples below.

[0161] [Method for Identifying the Compounds of the Present Invention] The compounds of the present invention can be identified by various identification methods, such as spectral identification methods including nuclear magnetic resonance (NMR) spectroscopy and infrared absorption spectroscopy (IR), mass spectrometry, and chromatography.

[0162] [[Photoacid Generator]] The photoacid generator of the present invention contains the compound of the present invention. The inventors have found that the compound of the present invention exhibits the property of generating acid upon irradiation with light, and possesses excellent thermal latent properties and high UV sensitivity. Therefore, the compound of the present invention is suitably used as a photoacid generator by utilizing these properties. Furthermore, the photoacid generator containing the compound of the present invention maintains the excellent properties of the compound of the present invention, possessing excellent thermal latent properties and high UV sensitivity. Due to its high UV sensitivity, when used as a photoacid generator for an acid-reactive composition, the compound and photoacid generator of the present invention can rapidly cure the acid-reactive composition, while still producing a cured product with excellent heat resistance and color suppression performance (transparency). Moreover, during the thermal decomposition of the compound and photoacid generator of the present invention, SbF ６Unlike HF and the compound described in Patent Document 1, which generate volatile gases such as carbon dioxide, the photoacid generator (compound) of the present invention does not generate volatile gases such as carbon dioxide, and the carboxylic acid produced as a by-product by thermal decomposition does not inhibit the curing of the acid-reactive compound and can be incorporated into the cured product. Therefore, the cured product exhibits excellent curing properties such as heat resistance, transparency, and suppression of residual bubbles (homogeneity). In particular, when using epoxy compounds described later as the acid-reactive compound, a strongly acidic catalyst is generally effective in inducing and promoting the cationic polymerization reaction. Conventionally, the selection of usable catalysts has been limited, and there have been problems in terms of legal regulations, heat resistance of the cured product, and generation of volatile gases. However, the photoacid generator (compound) of the present invention can generate strongly acidic active species and overcome the above-mentioned problems of conventional catalysts, making it highly useful. The photoacid generator of the present invention may contain compounds other than the compound of the present invention.

[0163] [Acid-Reactive Composition] The acid-reactive composition of the present invention contains the compound of the present invention (photoacid generator) and an acid-reactive compound. Because the acid-reactive composition of the present invention contains the compound of the present invention (photoacid generator), it maintains the excellent properties of the compound of the present invention and possesses excellent thermal latent properties and high UV sensitivity. Therefore, the acid-reactive composition of the present invention has high storage stability (especially thermal stability) before curing and exhibits high curing performance. Furthermore, the acid-reactive composition of the present invention, like the photoacid generator of the present invention, has the excellent properties described above that the photoacid generator of the present invention possesses. In the present invention, "acid reactivity" refers to the property of causing and proceeding with a chemical reaction by the acid generated from the compound of the present invention (photoacid generator), and includes reactivity that causes and proceeds with decomposition reactions, polymerization reactions, etc. The acid-reactive composition and acid-reactive compound may be any that exhibits the above acid reactivity, for example, a polymerization-reactive composition and a polymerization-reactive compound such as a cationic polymerizable compound that causes cationic polymerization. The acid-reactive composition of the present invention is preferably a polymerization-reactive composition, and more preferably a cationic polymerizable composition. Each component contained in the acid-reactive composition of the present invention may be one type or two or more types.

[0164] [Photoacid Generator] The photoacid generator in the acid-reactive composition of the present invention is the photoacid generator of the present invention, and its details are as described above.

[0165] [Acid-Reactive Compounds] When the acid-reactive composition of the present invention is a cationic polymerizable composition, it contains a cationic polymerizable compound. The cationic polymerizable compound is not particularly limited, and various known cationic polymerizable compounds (including polymers; the same applies hereinafter) can be used. As cationic polymerizable compounds, for example, one can refer to the cationic polymerizable compounds described in International Publication No. 2021 / 053993, and the contents described in this publication are incorporated as is as part of this specification.

[0166] Among various cationic polymerizable compounds, compounds having one or more acid-reactive groups selected from epoxy groups, oxetane groups, alkoxysilyl groups, and vinyl groups are preferred. Specifically, epoxy compounds having one or more epoxy groups, oxetane compounds having one or more oxetane groups, alkoxysilane compounds having one or more alkoxysilyl groups, and vinyl compounds having one or more vinyl groups are preferred, with epoxy compounds and oxetane compounds being more preferred. These cationic polymerizable compounds only need to have at least one of the above acid-reactive groups per molecule, but having two to six is ​​preferable in terms of polymerizability.

[0167] The epoxy compounds are not particularly limited and include, for example, aliphatic epoxides, alicyclic epoxides, aromatic epoxides, heterocyclic epoxides, etc. The epoxy group in the epoxy compound may be of the form of a glycidyl ether, glycidyl ester, olefin oxidation (alicyclic), etc. For examples of such epoxy compounds, refer to International Publication No. 2021 / 053993, and the contents of that publication are incorporated directly as part of this specification. Various epoxy resins can also be used. Furthermore, examples of epoxy compounds include epoxy compounds (epoxy resins) and epoxy compounds exhibiting polymerization reactivity described in International Publication No. 2014 / 185303, and the contents of that publication are incorporated directly as part of this specification.

[0168] The oxetane compound is not particularly limited and includes, for example, aliphatic oxetanes, alicyclic oxetanes, aromatic oxetanes, heterocyclic oxetanes, etc. In the oxetane compound, the form of the oxetane group may be any of the following: glycidyl ether type, glycidyl ester type, olefin oxidation (alicyclic) type, etc. For such oxetane compounds, refer to International Publication No. 2021 / 053993 and International Publication No. 2014 / 185303, and the contents described in each publication are incorporated as is as part of this specification.

[0169] The alkoxysilane compound is not particularly limited as long as it is a compound having an alkoxysilyl group. The alkoxysilyl group may be a monoalkoxysilyl group or a dialoxysilyl group, but a trialkoxysilyl group or a tetraalkoxysilyl group is preferred. The alkoxy group of the alkoxysilyl group is not particularly limited, and for example, the alkoxy group of substituent Z mentioned above is an example. The group other than the alkoxy group of the alkoxysilyl group is not particularly limited, and for example, substituent Z mentioned above is an example, among which alkyl groups, aryl groups, heterocyclic groups, etc., are preferred. In this invention, the alkoxysilyl group includes a group in which at least one alkoxy group is substituted with an aryloxy group or a heterocyclicoxy group. For such alkoxysilane compounds, refer to International Publication No. 2014 / 185303 (particularly silicon compounds (silicon resins), silane coupling agents) and Japanese Patent Application Publication No. 2013-100480, and the contents described in each publication are incorporated as is as part of this specification.

[0170] The vinyl compounds are not particularly limited and include, for example, vinyl ether compounds such as aliphatic monovinyl ethers, aromatic monovinyl ethers, and polyfunctional vinyl ethers; aromatic vinyl compounds (styrene compounds); and nitrogen-containing vinyl compounds such as N-vinylcarbazole and N-vinylpyrrolidone. For such vinyl compounds, refer to International Publication No. 2021 / 053993, and the contents of this publication are incorporated as is into this specification. Other vinyl compounds include (meth)acrylate compounds (C11), acrylamide compounds (C12), and other radical polymerizable compounds (C13) described in Japanese Patent Application Publication No. 2021-128259, and carboxyl group-containing vinyl monomers (Ba), hydrophobic group-containing vinyl monomers (Bb), and sulfonic acid group-containing vinyl monomers (Bc) described in Japanese Patent Application Publication No. 2013-1821, and the contents of each publication are incorporated as is into this specification.

[0171] [Other Components] The acid-reactive composition of the present invention may contain components other than the compound of the present invention and the acid-reactive compound ("other components"). Examples of other components include components commonly used in acid-reactive compositions containing photoacid generators, cationic polymerizable compositions, etc. Examples include solvents, additives, and photoacid generators other than the compound of the present invention.

[0172] <Solvent> The solvent that may be contained in the acid-reactive composition of the present invention is not particularly limited, and includes, for example, aromatic hydrocarbon compounds such as benzene, xylene, toluene, ethylbenzene, styrene, trimethylbenzene, and diethylbenzene; saturated or unsaturated hydrocarbon compounds such as cyclohexane, methylcyclohexane, ethylcyclohexane, cyclohexene, dipentene, n-pentane, isopentane, n-hexane, isohexane, n-heptane, isoheptane, n-octane, isooctane, n-nonane, isononane, n-decane, isodecane, tetrahydronaphthalene, squalane, p-menthane, o-menthane, and m-menthane; diethyl ether, di-n-propyl ether, diisopropyl ether, dibutyl ether, ethylpropyl ether, tert-butyl methyl ether, diphenyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, diethylene glycol methyl ethyl ether, dipropylene glycol dimethyl ether, dipropyl Examples of ethers include ethylene glycol diethyl ether, dipropylene glycol dibutyl ether, dipropylene glycol methyl ethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dipropyl ether, ethylene glycol methyl ethyl ether, tetrahydrofuran, 1,4-dioxane, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, and diethylene glycol monoethyl ether acetate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diethyl ketone, dipropyl ketone, methyl amyl ketone, cyclopentanone, cyclohexanone, and cycloheptanone; and esters such as ethyl acetate, methyl acetate, butyl acetate, propyl acetate, cyclohexyl acetate, methyl cellosolve acetate, ethyl acetate cellosolve, butyl acetate cellosolve, ethyl lactate, propyl lactate, butyl lactate, isoamyl lactate, and butyl stearate.

[0173] <Additives> The additives that may be contained in the acid-reactive composition of the present invention are not particularly limited, and include, for example, fillers, pigments, dyes, leveling agents, defoaming agents, antistatic agents, ultraviolet absorbers, pH adjusters, dispersants, dispersion aids, surface modifiers, plasticizers, plasticization accelerators, anti-sagging agents, and curing accelerators. Since the compounds of the present invention exhibit high UV sensitivity, the acid-reactive composition of the present invention does not need to contain a sensitizer, but it may contain a sensitizer from the viewpoint of further enhancing UV sensitivity. Furthermore, since the compounds of the present invention exhibit excellent thermal latent properties, the acid-reactive composition of the present invention does not need to contain photoacid generators other than the compounds of the present invention, but it may contain photoacid generators other than the compounds of the present invention from the viewpoint of further enhancing UV sensitivity and acid generation effect. Various known compounds can be used as these sensitizers and photoacid generators.

[0174] [Composition of Acid-Reactive Composition] The content of each component in the acid-reactive composition of the present invention is not particularly limited and can be determined as appropriate. For example, in the acid-reactive composition of the present invention, the content of the compound of the present invention can be 0.01 to 20% by mass of the total of the compound of the present invention and the acid-reactive compound in 100% by mass, preferably 0.05 to 10% by mass, and more preferably 0.1 to 5% by mass, in terms of thermal latentness and UV sensitivity. In the acid-reactive composition of the present invention, the content of the acid-reactive compound can be 80 to 99.99% by mass of the total of the compound of the present invention and the acid-reactive compound in 100% by mass, preferably 90 to 99.95% by mass, and more preferably 95 to 99.9% by mass, in terms of thermal latentness and UV sensitivity. In the acid-reactive composition of the present invention, the total content of the compound of the present invention and the acid-reactive compound is not particularly limited and can be appropriately determined considering the above-mentioned content. For example, it can be 10 to 100% by mass in 100% by mass of the acid-reactive composition of the present invention, preferably 30 to 100% by mass, and more preferably 50 to 100% by mass, in terms of thermal latentness and UV sensitivity.

[0175] In the acid-reactive composition of the present invention, the total content of other components is not particularly limited and can be appropriately determined, for example, it can be 0 to 90% by mass, preferably 0 to 70% by mass, and more preferably 0 to 50% by mass, based on 100% by mass of the acid-reactive composition of the present invention. In the acid-reactive composition of the present invention, the solvent content is not particularly limited and can be appropriately determined considering the total content of the compound of the present invention and the acid-reactive compound, the total content of other components, etc. For example, it can be 0 to 90% by mass, preferably 0 to 70% by mass, and more preferably 0 to 50% by mass, based on 100% by mass of the acid-reactive composition of the present invention. In the acid-reactive composition of the present invention, the total content of additives is not particularly limited and can be appropriately determined considering the total content of the compound of the present invention and the acid-reactive compound, the total content of other components, etc. For example, it can be 0 to 90% by mass, preferably 0 to 70% by mass, and more preferably 0 to 50% by mass, based on 100% by mass of the acid-reactive composition of the present invention.

[0176] [Preparation of Acid-Reactive Composition] The acid-reactive composition of the present invention can be prepared by mixing the compound of the present invention and an acid-reactive compound, and optionally other components. The mixing conditions are not particularly limited.

[0177] [Uses of Acid-Reactive Compositions] The acid-reactive compositions of the present invention can be used as photocurable materials, taking advantage of the excellent properties described above. They are suitably used as various materials such as resist materials (also called protective agents), paints (coating agents), printing inks, interlayer insulating materials, wiring covering materials, sealants, and adhesives. The acid-reactive compositions of the present invention are preferably resist materials (compositions for resists).

[0178] [Cured product of acid-reactive composition] The acid-reactive composition of the present invention hardens upon irradiation with active energy rays to form a cured product. As described above, this cured product exhibits excellent heat resistance and discoloration suppression performance (transparency), and furthermore, it also exhibits excellent suppression of residual air bubbles (homogeneity).

[0179] [Acid Generation Method] The acid generation method of the present invention includes irradiating the compound of the present invention with active energy rays. This causes the compound of the present invention (photoacid generator) to undergo a photoreaction (photodecomposition), and as an active species, X in general formula (1) １１ (Ar １１ ) (Ar １２ ) (Ar １３ A Lewis acid represented by ) can be generated. In the present invention, "active energy rays" can be any light having energy (the absorption wavelength of the photoacid generator of the present invention) that promotes the decomposition of the photoacid generator of the present invention, such as visible light, ultraviolet light (UV), X-rays, electron beams, and radiation, but ultraviolet light is preferred. In the acid generation method of the present invention, the target to which the active energy rays are irradiated is the compound of the present invention, but the compound of the present invention does not need to exist alone, but may be in a state coexisting with an acid-reactive compound (the acid-reactive composition of the present invention, or a coated film thereof).

[0180] [Irradiation Process of Active Energy Rays] The conditions for irradiating the compound of the present invention with active energy rays are not unique, depending on the type (chemical structure) of the compound of the present invention. An example of irradiation conditions is described below. The irradiation device for active energy rays is not particularly limited and may include, for example, low-pressure, medium-pressure, high-pressure or ultra-high-pressure mercury lamps, metal halide lamps, LED lamps, xenon lamps, halogen lamps, carbon arc lamps, fluorescent lamps, semiconductor solid-state lasers, argon lasers, He-Cd lasers, KrF excimer lasers, ArF excimer lasers, F ２ Examples include various laser devices such as lasers.

[0181] The irradiation intensity, irradiation time, and integrated light dose of the active energy ray are appropriately set as conditions that can decompose the compound of the present invention. For example, the irradiation intensity of the active energy ray may be, for example, 0.01 to 100,000 mW / cm². ２ This can be done. The irradiation time for the active energy rays can be, for example, 1 to 300 seconds at room temperature (20 to 30°C). The integrated light intensity of the active energy rays can be 0.01 to 40,000 J / cm². ２ It can be done this way.

[0182] [Other Steps] The acid generation method of the present invention may include steps other than the active energy ray irradiation step (sometimes referred to as "other steps"). Other steps are not particularly limited and include, for example, a step of preparing the acid-reactive composition of the present invention, a step of applying the acid-reactive composition of the present invention, a pre-bake step of volatilizing the solvent from the acid-reactive composition (coated film) of the present invention, and an after-cure step of heating the cured product by irradiation with active energy rays. In the step of applying the acid-reactive composition of the present invention, the application method is not particularly limited and includes, for example, various application methods such as bar coating, spray coating, curtain coating, roll coating, screen printing, offset printing, and gravure printing. The thickness of the coated film is set to the thickness of the desired cured product. In the after-cure step, the heating temperature and heating time are not particularly limited and, for example, the heating temperature can be room temperature or higher and 120°C or lower, and the heating time can be 1 to 30 minutes.

[0183] The present invention will be described in more detail below based on examples, but the present invention is not to be construed as being limited thereto. In the following examples, "parts" and "%" representing the composition are by mass unless otherwise specified. In the present invention, "room temperature" means 25°C.

[0184] In the examples, thermogravimetric differential thermal analysis (TG-DTA) was performed using STA2500 Regulus (trade name, manufactured by Netszch), and UV 365 nm irradiation was performed using MUVBA-0.3×0.4×0.5 UV365-J (trade name, manufactured by Aitec). HPLC analysis was performed using LC-2050 (trade name, manufactured by Shimadzu Corporation) and Wako Pack R Ultra C18-5 (trade name, manufactured by Fujifilm Wako Pure Chemical Industries). １ H-NMR and １９ F-NMR was performed using a JNM-ECS 400 (trade name, 400 MHz, manufactured by JEOL Ltd.) with tetramethylsilane (TMS) as the standard substance.

[0185] In the chemical formula shown below, Bz represents a benzoyl group, Me represents a methyl group, Ph represents a phenyl group, and Et represents an ethyl group.

[0186] [Example 1: Synthesis of Compound 1] Compound 1: triphenylsulfonium ((2-(3-benzoylphenyl)propanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows: Ketoprofen (265 mg, 1.04 mmol) and 4 mL of cyclopentyl methyl ether were added to a nitrogen-purged two-neck flask. Potassium tert-butoxide (112 mg, 1.00 mmol) was then added under ice cooling, and the mixture was stirred at room temperature (25°C) for 30 minutes. Subsequently, tris(pentafluorophenyl)borane (427 mg, 0.833 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. Then, triphenylsulfonium chloride (300 mg, 1.00 mmol) and 4 mL of deionized water were added, and after stirring, the mixture was allowed to stand to separate into two layers. The organic layer was separated, washed with deionized water, and concentrated under reduced pressure to obtain 670 mg of a colorless powder (yield: 78%). １ H-NMR and １９ F-NMR analysis confirmed that the product was compound 1 as indicated. １ H-NMR (C ６ D ６ )> σ: 1.51 (d, 3H), 3.79 (q, 1H), 6.83 to 6.96 (m, 15H), 6.99 to 7.06 (m, 3H), 7.10 to 7.16 (m , 1H), 7.31-7.33 (m, 1H), 7.55-7.57 (m, 1H), 7.64-7.67 (m, 2H), 7.74-7.77 (m, 1H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F) <HPLC (210 nm, elution time)> 2.9 min (cation portion, 51.0 area%), 13.2 min (anion portion, 47.5 area%)

[0187] [Example 2: Synthesis of Compound 2] As compound 2 shown above, triphenylsulfonium ((2-(3-(thiophene-2-carbonyl)phenyl)propanoyl)oxy)tris(pentafluorophenyl)borate was synthesized as follows. That is, compound 2 was synthesized in the same manner as in Example 1 (yield 74%), except that suprofen was used instead of ketoprofen, and the product was confirmed to be compound 2 in the same manner as compound 1. １ H-NMR (C ６ D ６ )> σ: 1.51 (d, 3H), 3.71 (q, 1H), 6.83 to 6.96 (m, 16H), 7.00 to 7.16 (m, 1H), 7.3 1-7.33 (m, 1H), 7.50-7.53 (m, 1H), 7.60-7.67 (m, 2H), 7.79-7.82 (m, 1H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0188] [Example 3: Synthesis of Compound 3] Compound 3, triphenylsulfonium ((2-(thioxanthon-2-yl)propanoyl)oxy)tris(pentafluorophenyl)borate), shown above, was synthesized as follows. That is, compound 3 was synthesized in the same manner as in Example 1 (yield 70%), except that 2-(thioxanthon-2-yl)propionic acid was used instead of ketoprofen, and the product was confirmed to be compound 3 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 1.47 (d, 3H), 3.77 (q, 1H), 6.80 to 7.10 (m, 19H), 7.15 (dd, 1H), 8.39 (d, 1H), 8.54 to 8.58 (m, 1H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0189] [Example 4: Synthesis of Compound 4] Compound 4, triphenylsulfonium (2-(11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetoxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. That is, compound 4 was synthesized in the same manner as in Example 1 (yield: 80%), except that isoxepac was used instead of ketoprofen, and the product was confirmed to be compound 4 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 3.60 (s, 2H), 4.50 (s, 2H), 6.67 to 6.68 (m, 1H), 6.80 to 7.00 (m, 18H), 7.15 to 7.36 (m, 1H), 7.70 to 7.71 (m, 1H), 8.11 (s, 1H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0190] [Example 5: Synthesis of Compound 5] Compound 5, triphenylsulfonium ((2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. That is, compound 5 was synthesized in the same manner as in Example 1 (yield: 84%), except that fenofibric acid was used instead of ketoprofen, and the product was confirmed to be compound 5 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 1.86 (s, 6H), 6.76 to 7.15 (m, 19H), 7.41 to 7.44 (m, 2H), 7.58 to 7.62 (m, 2H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0191] [Example 6: Synthesis of Compound 6] Compound 6, triphenylsulfonium ((2-(6-methoxynaphthalene-2-yl)propanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. That is, compound 6 was synthesized in the same manner as in Example 1 (yield: 82%), except that naproxen was used instead of ketoprofen, and the product was confirmed to be compound 6 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 1.75 (d, 3H), 3.36 (s, 3H), 3.98 (q, 1H), 6.70 to 6.86 (m, 16H), 7.04 to 7.15 (m, 1H), 7.31 to 7.52 (m, 4H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0192] [Example 7: Synthesis of Compound 7] Compound 7, triphenylsulfonium ((6-chloro-4-oxothiochroman-2-carbonyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. That is, compound 7 was synthesized in the same manner as in Example 1 (yield: 80%), except that 6-chlorothiochromanon-2-carboxylic acid was used instead of ketoprofen, and the product was confirmed to be compound 7 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 2.56 (dd, 1H), 2.78 (dd, 1H), 3.74 (dd, 1H), 6.72 (d, 1H), 6.81 to 7.00 (m, 16H), 7.69 (d, 1H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0193] [Example 8: Synthesis of Compound 8] Compound 8, triphenylsulfonium (2-oxo-2-phenylacetoxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. Specifically, compound 8 was synthesized in the same manner as in Example 1 (yield: 69%), except that benzoyl glyceride was used instead of ketoprofen. The product was then confirmed to be compound 8 in the same manner as in Example 1. １ H-NMR (C ６ D ６ )> σ: 6.78 to 6.88 (m, 9H), 6.95 to 7.16 (m, 9H), 8.21 to 8.24 (m, 2H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0194] [Example 9: Synthesis of Compound 9] Compound 9, triphenylsulfonium ((4-benzoylbenzoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. That is, compound 9 was synthesized in the same manner as in Example 1 (yield: 78%), except that 4-benzoylbenzoic acid was used instead of ketoprofen, and the product was confirmed to be compound 9 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 6.80 to 7.06 (m, 18H), 7.51 to 7.53 (m, 2H), 7.67 (d, 2H), 8.16 (d, 2H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0195] [Example 10: Synthesis of Compound 10] Compound 10, triphenylsulfonium (((4-phenylbuta-1,3-dien-1-yl)benzoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. That is, compound 10 was synthesized in the same manner as in Example 1 (yield: 62%), except that 4-(4-phenylbuta-1,3-dien-1-yl)benzoic acid was used instead of ketoprofen, and the product was confirmed to be compound 10 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 6.71 (dd, 2H), 6.81 to 7.32 (m, 24H), 7.74 (d, 2H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0196] [Example 11: Synthesis of Compound 11] Compound 11: triphenylsulfonium (4-benzoylphenoxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. That is, compound 11 was synthesized in the same manner as in Example 1 (yield: 80%), except that 4-benzoylphenol was used instead of ketoprofen, and the product was confirmed to be compound 11 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 6.74 to 7.04 (m, 18H), 7.50 to 7.55 (m, 4H), 7.70 (d, 2H) < １９ F-NMR (C ６ D ６ )> σ: -166.3 to -165.6 (m, 6F), -161.9 to -161.7 (m, 3F), -133.4 to -133.2 (m, 6F)

[0197] [Example 12: Synthesis of Compound 12] Compound 12, diphenyl(4-(phenylthio)phenyl)sulfonium ((2-(3-benzoylphenyl)propanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. Specifically, compound 12 was synthesized in the same manner as in Example 1 (yield: 75%), except that diphenyl(4-(phenylthio)phenyl)sulfonium bromide was used instead of triphenylsulfonium chloride, and the product was confirmed to be compound 12 in the same manner as in compound 1.

[0198] [Example 13: Synthesis of Compound 13] Compound 13, diphenyl(4-chlorophenyl)sulfonium ((2-(3-benzoylphenyl)propanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. Specifically, compound 13 was synthesized in the same manner as in Example 1 (yield: 72%), except that diphenyl(4-chlorophenyl)sulfonium bromide was used instead of triphenylsulfonium chloride, and the product was confirmed to be compound 13 in the same manner as in compound 1.

[0199] [Example 14: Synthesis of Compound 14] Compound 14, bis(4-(tert-butyl)phenyl)iodonium ((2-(3-benzoylphenyl)propanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. Specifically, compound 14 was synthesized in the same manner as in Example 1 (yield: 95%), except that bis(4-(tert-butyl)phenyl)iodonium chloride was used instead of triphenylsulfonium chloride, and the product was confirmed to be compound 14 in the same manner as in compound 1.

[0200] [Example 15: Synthesis of Compound 15] Compound 15, dibenzo[b,d]iodium((2-(3-benzoylphenyl)propanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. Specifically, compound 15 was synthesized in the same manner as in Example 1 (yield: 65%), except that dibenzo[b,d]iodium triflate was used instead of triphenylsulfonium chloride, and the product was confirmed to be compound 15 in the same manner as in compound 1.

[0201] [Example 16: Synthesis of Compound 16] Compound 16, (anthracene-9-ylmethyl)triethylammonium ((2-(3-benzoylphenyl)propanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. Specifically, compound 16 was synthesized in the same manner as in Example 1 (yield: 85%), except that (anthracene-9-ylmethyl)triethylammonium chloride was used instead of triphenylsulfonium chloride, and the product was confirmed to be compound 16 in the same manner as in compound 1.

[0202] [Example 17: Synthesis of Compound 17] Compound 17, benzyltriphenylphosphonium ((2-(3-benzoylphenyl)propanoyl)oxy)tris(pentafluorophenyl)borate, shown above, was synthesized as follows. Specifically, compound 17 was synthesized in the same manner as in Example 1 (yield: 87%), except that benzyltriphenylphosphonium chloride was used instead of triphenylsulfonium chloride, and the product was confirmed to be compound 17 in the same manner as in compound 1.

[0203] [Example 18: Synthesis of Compound 18] Compound 18: triphenylsulfonium ((2-(3-benzoylphenyl)propanoyl)oxy)tris(3,4,5-trifluorophenyl)borate, shown above, was synthesized as follows. That is, compound 18 was synthesized in the same manner as in Example 1 (yield: 70%), except that tris(3,4,5-trifluorophenyl)borane was used instead of tris(pentafluorophenyl)borane in Example 1, and the product was confirmed to be compound 18 in the same manner as in compound 1. １ H-NMR (C ６ D ６ )> σ: 1.51 (d, 3H), 3.79 (q, 1H), 6.83 to 6.96 (m, 15H), 6.99 to 7.06 (m, 3H), 7.10 to 7.16 (m, 1H), 6.5 1-6.63 (m, 6H), 7.31-7.33 (m, 1H), 7.55-7.57 (m, 1H), 7.64-7.67 (m, 2H), 7.74-7.77 (m, 1H) < １９ F-NMR (C ６ D ６ )> σ: -172.3 to -171.9 (m, 3F), -141.5 to -141.3 (m, 6F)

[0204] [Comparative Example 1: Synthesis of Compound 19] Compound 19: triphenylsulfonium tetrakis(pentafluorophenyl) borate, shown above, was synthesized as follows: Triphenylsulfonium chloride (1 g, 3.4 mmol) and lithium tetrakis(pentafluorophenyl) borate (1.9 g, 2.8 mmol) were dissolved in tert-butyl methyl ether (20 mL) and washed three times with deionized water (20 mL). Subsequently, 2.5 g of a colorless powder (yield: 95%) was obtained by concentration under reduced pressure. １ H-NMR and １９ F-NMR analysis confirmed that the product was compound 19.

[0205] [Reference Example 1: Preparation of Compound 20] The compound 20: 4-isopropylphenyl(p-toluyl)iodonium tetrakis(pentafluorophenyl)borate shown above was a commercially available product (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0206] [Evaluation] The following evaluations were performed on each compound synthesized in the examples and comparative examples, as well as the compound prepared in the reference example, and the results are shown in Table 1.

[0207] <Evaluation 1: Evaluation of the thermal stability of the compounds> 10 mg of each compound was measured, and the temperature at which it lost 10% weight was determined by thermogravimetric differential thermal analysis. In this evaluation, a higher temperature at which it lost 10% weight indicates higher thermal stability of the compound.

[0208] <Evaluation 2: Evaluation of UV curability> Each compound (1.5 parts by mass) was dissolved in tert-butyl methyl ether (1.5 parts by mass), and an acid-reactive composition was prepared by mixing it with the compound shown below (Celoxide 2021P, manufactured by Daicel Corporation, 100 parts by mass), which is an acid-reactive compound having two epoxy groups.

[0209] At room temperature, each prepared composition was coated onto a glass plate to a thickness of 5 μm, and then exposed to UV light with a wavelength of 365 nm (irradiation intensity of 100 mW / cm²). ２ The coating film surface was irradiated with UV light, and the time (in seconds) required for the coating film to harden (until the tackiness disappeared by palpation) was measured. The results were then evaluated in three stages based on the evaluation criteria below. In this evaluation, a shorter UV light irradiation time indicates higher UV curability of the composition. In Comparative Example 2 (when a sensitizer is used), ketoprofen (1.5 parts by mass) was added to the composition of Comparative Example 2 as a sensitizer. (Evaluation Criteria) ○: Hardened after 30 seconds of irradiation △: Did not harden after 30 seconds of irradiation, but hardened after 90 seconds of irradiation ×: Did not harden after 90 seconds of UV light irradiation, but hardened after 30 seconds of irradiation using a high-pressure mercury lamp (product name: HLR100T-2, manufactured by Sen Special Light Source Co., Ltd.)

[0210] <Evaluation 3: Evaluation of the heat resistance of UV-cured products> 10 mg of each cured product obtained in Evaluation 2 was measured, and the temperature at which it lost 10% weight was determined by thermogravimetric differential thermal analysis. In this evaluation, a higher temperature at which it lost 10% weight indicates higher thermal stability of the cured product.

[0211] <Evaluation 4: Color Evaluation of Cured Products> Each cured product obtained in Evaluation 2 above was heated on a hot plate heated to 200°C for 5 minutes. After heating, each cured product was placed on a piece of white paper, and the change in appearance of each product was visually observed and evaluated in three stages based on the following evaluation criteria. (Evaluation Criteria) ○: Maintained transparency △: Maintained transparency but showed a slightly lighter yellow than the white paper ×: Turned black

[0212]

[0213] The results in Table 1 show the following: Compound 19, a conventional photoacid generator, had poor UV curability and significantly inferior UV sensitivity (Comparative Example 1). Compound 19 did not show any improvement in UV sensitivity even when used in combination with a sensitizer (Comparative Example 2). Furthermore, compound 20, a conventional photoacid generator, had poor thermal stability and significantly inferior thermal latent properties (Comparative Example 3). Moreover, Comparative Examples 1 to 3 all exhibited poor heat resistance in the cured products and discolored to black, failing to demonstrate any discoloration suppression performance.

[0214] In contrast, the compound represented by general formula (1) exhibited high thermal stability, and the acid-reactive composition using this compound as a photoacid generator also showed excellent UV curability (Examples 1-18). From this, it can be seen that the compound represented by general formula (1) and the photoacid generator possess both excellent thermal potential and high UV sensitivity, and that the acid-reactive composition containing the compound represented by general formula (1) exhibits high storage stability (especially thermal stability) before curing and high curing performance. On the other hand, the cured products of Examples 1-18 showed good heat resistance and suppressed discoloration. From this, it can be seen that an acid-reactive composition containing the compound represented by general formula (1) as a photoacid generator can produce cured products that exhibit excellent heat resistance and discoloration suppression performance (transparency). Moreover, the compound represented by general formula (1) and the photoacid generator can rapidly induce and promote the curing of epoxy compounds without generating volatile gases, and the by-product carboxylic acid does not inhibit the curing of the epoxy compound. Furthermore, the by-product carboxylic acid is incorporated into the cured product. As a result, the cured products of Examples 1 to 18 exhibit excellent heat resistance and color suppression performance (transparency) while also demonstrating excellent suppression of residual bubbles (homogeneity). From these results, it can be seen that the compounds and photoacid generators of the present invention can generate strongly acidic active species to induce and promote acid-catalyzed reactions of various acid-reactive compounds, including epoxy compounds, and can overcome the various problems of conventional catalysts, demonstrating their high usefulness.

[0215] Although we have described the present invention along with its embodiments, we do not intend to limit our invention in any detail of the description unless specifically designated, and we believe that it should be interpreted broadly without contradicting the spirit and scope of the invention as set forth in the appended claims.

[0216] This application claims priority based on Japanese Patent Application No. 2024-208599, filed in Japan on 29 November 2024, the contents of which are incorporated herein by reference as part of this specification.

Claims

1. A compound represented by the following general formula (1). In the general formula (1), Ar １１ to Ar １３ each independently represents an aromatic hydrocarbon ring group having at least one halogeno group and an alkyl group having 1 to 4 carbon atoms containing a fluorine atom as a substituent, and R １３ represents a group having at least one group selected from a benzyl group, an alkoxy group, an alkyl group having 1 to 20 carbon atoms which may have a branched or cyclic structure, an aliphatic heterocyclic group, a halogeno group, a hydroxy group, a sulfo group, a nitro group, an aromatic hydrocarbon ring group and an aromatic heterocyclic group, a condensed polycyclic aromatic hydrocarbon ring group or a condensed polycyclic aromatic heterocyclic group; a group having an aromatic ketone skeleton; or a group having an aromatic hydrocarbon ring group or an aromatic heterocyclic group and a conjugated bond group forming a conjugated system continuous with the group, and R １１ and R １２ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Z １１ represents an oxygen atom or a sulfur atom, m1 represents 0 or 1, and when n1 is 0, m1 represents 0, n1 represents an integer of 0 to 4, p1 represents 0 or 1, X １１ represents a boron atom, an aluminum atom, a gallium atom or an indium atom, Y １１ represents an organic onium cation. However, when R １３ is a group having a condensed polycyclic aromatic heterocyclic group, an aromatic ketone skeleton, or a conjugated bond group forming a conjugated system continuous with the aromatic heterocyclic group, and one of the bonding hands of the hetero atom constituting the R １３ represents a bonding hand with the adjacent Z １１ the embodiments where m1 = n1 = 0 and the embodiment where m1 = 1 are excluded.

2. R in the general formula (1) １３ The compound according to claim 1, wherein the substituent may be a condensed polycyclic aromatic hydrocarbon ring group or a condensed polycyclic aromatic heterocyclic ring group, or a group represented by any of the following general formulas (3) to (6-2). In general formula (3), Ar ３１ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, ３１ This may be an aromatic hydrocarbon ring group or aromatic heterocyclic group having substituents, a C1-C10 alkyl group having branched or cyclic structures, an aliphatic heterocyclic group, a hydroxyl group, an alkoxy group, a sulfo group, a nitro group, a carboxyl group, or -SO ２ -Ar ３２ The group represented by (Ar ３２ ) represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. ３２ and R ３３ Each of these independently represents an alkyl or alkoxy group having 1 to 5 carbon atoms, and R ３１ ~R ３３ Two or three of these may be connected to each other to form a ring structure, and *- is Ar ３１ The carbon atoms that make up the compound and Z in general formula (1) １１ This represents a bonding action that connects and . In general formula (4), Ar ４１ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, ４１ * represents an alkylene group having 1 to 10 carbon atoms that may have substituents, or an alkenylene group having 2 to 10 carbon atoms that may have substituents, and which may have an ether group, a sulfide group, or a carbonyl group in its molecular chain, and *- represents Ar ４１ or R ４１ The carbon atoms that make up the compound and Z in general formula (1) １１ This represents a bonding action that connects and . In general formula (5-1), Ar ５１１ and Ar ５１２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, and R ５１１ and R ５１２ Each of these independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, A ５１ R represents a single bond, oxygen atom, sulfur atom, or carbonyl group. ５１１ , R ５１２ and A ５１ None of them form a single bond, and *- represents Ar ５１１ The carbon atoms that make up the compound and Z in general formula (1) １１ This represents a bonding action that connects and . In general formula (5-2), Ar ５２１ and Ar ５２２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, and the Ar ５２１ The carbon atoms and Ar that make up the structure ５２２ Among the carbon atoms that make up Ar ５２１ -C(=O)-Ar ５２２ The α-position carbon atoms of the carbon atoms involved in the bond may also be bonded together, and *- is Ar ５２１ The carbon atoms that make up the compound and Z in general formula (1) １１ This represents a bonding action that connects and . In general formula (6-1), Ar ６１１ represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, and *- represents the carbonyl carbon and Z in general formula (1). １１ This represents a bonding action that connects and . In general formula (6-2), Ar ６２１ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, ６２２ * represents an aromatic hydrocarbon ring group or aromatic heterocyclic group, hydroxyl group, sulfo group, nitro group, carboxyl group, or a C1-C10 alkyl group which may have a branched or cyclic structure and may have heteroatoms in its molecular chain, and *- represents Ar ６２１ The carbon atoms that make up the compound and Z in general formula (1) １１ This represents a coupling that joins two things together.

3. The Y in the general formula (1) １１ The compound according to claim 1, wherein the organo-onium cation represented by is selected from sulfonium cation, iodonium cation, ammonium cation, phosphonium cation, and pyridinium cation.

4. The Y in the general formula (1) １１ The compound according to claim 1, wherein the organo-onium cation represented by is represented by any one of the following general formulas (7) to (11). In general formula (7), R ７１ This is an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, a group represented by the following general formula (12), or a group represented by the following general formula (13). ７２ and R ７３ Each of these is independently an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, a group represented by the following general formula (12), a group represented by the following general formula (13), an alkyl group having 1 to 20 carbon atoms which may have substituents, or -CH ２ -Ar ７２ The group represented by (Ar ７２ ) represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. ７１ ~R ７３ If two or more of these are the aromatic hydrocarbon ring group, the aromatic heterocyclic group, the group represented by the following general formula (12), or the group represented by the following general formula (13), then the carbon atoms at the α-position of the carbon atoms involved in the bonding of the sulfur atom in general formula (7) among the carbon atoms constituting the aromatic hydrocarbon ring group, the aromatic heterocyclic group, the group represented by the following general formula (12), or the group represented by the following general formula (13) may be bonded to each other via a heteroatom or an alkyl group having 1 to 6 carbon atoms, or they may be directly bonded to each other. In general formula (12), Ar １２１ and Ar １２２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, and R １２１ and R １２２ each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, and A １２１ represents a single bond, an oxygen atom, a sulfur atom or a carbonyl group, and R １２１ , R １２２ and A １２１ none of them becomes a single bond, and *- is a bond connecting a carbon atom constituting Ar １２１ to a cation atom or a group represented by -S-Ar ７１ (Ar ７１ is as described above.) with S. In general formula (13), Ar １３１ and Ar １３２ each independently represents an optionally substituted aromatic hydrocarbon ring group or aromatic heterocyclic group, and the carbon atoms constituting the Ar １３１ and the carbon atoms constituting Ar １３２ among which the carbon atoms at the α-position of the carbon atoms participating in the bond of Ar １３１ -C(=O)-Ar １３２ may be bonded to each other, and *- is a bond connecting a carbon atom constituting Ar １３１ to a cation atom or a group represented by S of a group represented by -S-Ar ７１ . In general formula (8), R ８１ and R ８２ each independently represents an optionally substituted aromatic hydrocarbon ring group or aromatic heterocyclic group, an aromatic hydrocarbon ring group or aromatic heterocyclic group having -S-Ar ７１ as a substituent (Ar ７１ is as described above.), a group represented by the general formula (12), or a group represented by the general formula (13), and among the carbon atoms constituting the aromatic hydrocarbon ring group, aromatic heterocyclic group, group represented by the general formula (12), or group represented by the general formula (13) represented by the R ８１ and R ８２ the carbon atoms at the α-position of the carbon atoms participating in the bond of the iodine atom in general formula (8) may be bonded to each other via a hetero atom or an alkyl group having 1 to 6 carbon atoms, or may be directly bonded. In general formula (9), R ９１ is an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent, or an aromatic hydrocarbon ring group or an aromatic heterocyclic group having -S-Ar as a substituent ７１ (Ar ７１ is as described above.), a group represented by the general formula (12), a group represented by the general formula (13), or -CH ２ -Ar ７２ (Ar ７２ is as described above.), and R ９２ to R ９４ each independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or -CH ２ -Ar ７２ (Ar ７２ is as described above.). In the general formula (10), R １０１ is an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent, or an aromatic hydrocarbon ring group or an aromatic heterocyclic group having -S-Ar as a substituent ７１ (Ar ７１ is as described above.), a group represented by the general formula (12), a group represented by the general formula (13), or -CH ２ -Ar ７２ (Ar ７２ is as described above.), and R １０２ to R １０４ each independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or -CH ２ -Ar ７２ (Ar ７２ is as described above.). In the general formula (11), R １１１ is an alkyl group having 1 to 20 carbon atoms which may have a substituent, or -CH ２ -Ar １１１ (Ar １１１ represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent.), and R １１２ to R １１６ Each of these independently comprises a hydrogen atom, a C1-C20 alkyl group which may have substituents, a halogen group, a hydroxyl group, a sulfo group, a nitro group, a carboxyl group, a cyano group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and -CH ２ -Ar １１１ The group represented by (Ar １１１ As stated above, ), or -(C=O)-R １１７ The group represented by (R １１７ This represents an alkyl group having 1 to 10 carbon atoms, which may be branched, or an aromatic hydrocarbon ring group or aromatic heterocyclic group, which may have substituents.

5. The R in the general formula (1) １３ However, the group is represented by any of the general formulas (3) to (6-2) above, and the X １１ is a boron atom, and the Ar １１ ~Ar １３ The compound according to claim 2, wherein the groups are the same.

6. The Y in the general formula (1) １１ The compound according to claim 4, wherein the group is represented by the general formula (7) or (8).

7. The R in the general formula (1) １３ The compound according to claim 5, wherein the group is represented by the general formula (4), (5-1), or (5-2).

8. The R in the general formula (4) ４１ ga-S-CH ２ -CH ２ It is an alkylene group containing - or an alkenylene group containing -S-CH=CH-, Ar ４１ The compound according to claim 7, wherein is a phenyl group which may have substituents.

9. The Ar in the general formula (5-1) ５１１ and Ar ５１２ , and the Ar in the general formula (5-2) ５２１ and Ar ５２２ The compound according to claim 7, wherein each is independently a phenyl group or a monocyclic aromatic heterocyclic group which may have substituents.

10. The compound according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (1'). In general formula (1'), Ar １１’ ~Ar １３’ Each independently represents a halogen group and a phenyl group having at least one C1-C4 alkyl group containing a fluorine atom as substituents, and Ar １１’ ~Ar １３’ These are the same group, R １３’ X represents a group represented by the following general formulas (4'), (5'-1), or (5'-2), and １１’ represents a boron atom, Y １１’ R represents a group represented by the following general formula (7) or (8), １１ , R １２ Z １１ m1, n1, and p1 are the same as those in the general formula (1) above. In general formula (4'), Ar ４１’ R represents a phenyl group which may have substituents, ４１’ is, -S-CH ２ -CH ２ - represents an alkylene group with a total of 2 to 6 carbon atoms including -S-CH=CH- or an alkenylene group with a total of 2 to 6 carbon atoms including -S-CH=CH-, and *- represents Ar ４１’ or R ４１’ The carbon atoms that make up the and Z in general formula (1') １１ This represents a bonding action that connects and . In the general formula (5'-1), Ar ５１１’ and Ar ５１２’ Each independently represents a phenyl group or a monocyclic aromatic heterocyclic group which may have substituents, and R ５１１ and R ５１２ Each of these independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, A ５１ R represents a single bond, oxygen atom, sulfur atom, or carbonyl group. ５１１ , R ５１２ and A ５１ None of them form a single bond, and *- represents Ar ５１１’ The carbon atoms that make up the and Z in general formula (1') １１ This represents a bonding action that connects and . In the general formula (5'-2), Ar ５２１’ and Ar ５２２’ Each independently represents a phenyl group or a monocyclic aromatic heterocyclic group which may have substituents, and the Ar ５２１’ The carbon atoms and Ar that make up the structure ５２２’ Among the carbon atoms that make up Ar ５２１’ -C(=O)-Ar ５２２’ The α-position carbon atoms of the carbon atoms involved in the bond may be bonded together, and *- represents Ar ５２１’ The carbon atoms that make up the and Z in general formula (1') １１ This represents a coupling that joins two things together. In general formula (7), R ７１ This is an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ R represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents, a group represented by the following general formula (12), or a group represented by the following general formula (13). ７２ and R ７３ Each of these is independently an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, a group represented by the following general formula (12), a group represented by the following general formula (13), an alkyl group having 1 to 20 carbon atoms which may have substituents, or -CH ２ -Ar ７２ The group represented by (Ar ７２ ) represents an aromatic hydrocarbon ring group or aromatic heterocyclic group which may have substituents. ７１ ~R ７３ If two or more of these are the aromatic hydrocarbon ring group, the aromatic heterocyclic group, the group represented by the following general formula (12), or the group represented by the following general formula (13), then the carbon atoms at the α-position of the carbon atoms involved in the bonding of the sulfur atom in general formula (7) among the carbon atoms constituting the aromatic hydrocarbon ring group, the aromatic heterocyclic group, the group represented by the following general formula (12), or the group represented by the following general formula (13) may be bonded to each other via a heteroatom or an alkyl group having 1 to 6 carbon atoms, or they may be directly bonded to each other. In general formula (12), Ar １２１ and Ar １２２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, and R １２１ and R １２２ Each of these independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, A １２１ R represents a single bond, oxygen atom, sulfur atom, or carbonyl group. １２１ , R １２２ and A １２１ None of them form a single bond, and *- represents Ar １２１ The carbon atoms and cation atoms or -S-Ar that make up the structure ７１ The group represented by (Ar ７１ As stated above, it represents a bonding bond that connects S of ). In general formula (13), Ar １３１ and Ar １３２ Each of these independently represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, and the Ar １３１ The carbon atoms and Ar that make up the structure １３２ Among the carbon atoms that make up Ar １３１ -C(=O)-Ar １３２ The α-position carbon atoms of the carbon atoms involved in the bond may also be bonded together, and *- is Ar １３１ The carbon atoms and cation atoms or -S-Ar that make up the structure ７１ This represents a bond between the group represented by and the group represented by S. In general formula (8), R ８１ and R ８２ Each of these is independently an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have substituents, with -S-Ar as the substituent. ７１ Aromatic hydrocarbon ring group or aromatic heterocyclic group (Ar ７１ As stated above, ), represents a group represented by the general formula (12), or a group represented by the general formula (13), and R ８１ and R ８２ In the aromatic hydrocarbon ring group, aromatic heterocyclic group, group represented by general formula (12), or group represented by general formula (13), the carbon atoms at the α-position of the carbon atoms involved in the bonding of the iodine atom in general formula (8) may be bonded to each other via a heteroatom or an alkyl group having 1 to 6 carbon atoms, or they may be directly bonded to each other.

11. The compound according to claim 1, wherein p1 is 1.

12. The compound according to claim 10, wherein p1 is 1.

13. A photoacid generator comprising the compound described in any one of claims 1 to 12.

14. An acid-reactive composition containing the compound described in any one of claims 1 to 12 and an acid-reactive compound.

15. The acid-reactive composition according to claim 14, wherein the acid-reactive compound is a compound having one or more groups selected from epoxy groups, oxetane groups, alkoxysilyl groups, and vinyl groups.

16. The acid-reactive composition according to claim 14, wherein the acid-reactive composition is a resist composition.

17. An acid generation method comprising irradiating a compound according to any one of claims 1 to 12 with an active energy ray.

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