Onium salt compounds

Abstract

Provided is an onium salt compound that has excellent solvent compatibility and excellent storage stability. [Solution] General formula (1): JPEG0007718022000099.jpg49119 (In the formula, R A R represents an optionally substituted C1-15 alkyl group, etc. 4 indicates a hydrogen atom, etc. 5 and R 6 are the same or different and represent a hydrogen atom or the like; or 5 and R 6 These two groups may be bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent. The dotted line represents a single or double bond. X - represents a boron anion containing a fluorine-containing aromatic ring, etc. Onium salt compounds represented by the following formula:

Description

[Technical Field]

[0001] The present disclosure relates to onium salt compounds and the like. [Background technology]

[0002] In recent years, energy conservation has been required in various fields in response to social issues such as the SDGs. To meet this demand, light is considered an environmentally friendly energy source and is widely used. For example, in industry, photosensitive materials that utilize light have been industrialized, such as adhesives, sealing materials, and photoresists (e.g., Patent Documents 1 to 3). Known examples of the photosensitive material include reactive compositions obtained by mixing an acid generator with a reactive compound such as an epoxy compound, and cured products thereof.

[0003] There have been two types of acid generators to date: thermal acid generators and photoacid generators. For example, Patent Document 4 reports a sulfonium salt (onium salt compound) that generates acid when heated as a thermal acid generator. The reactive composition described in Patent Document 4, which is a mixture of the acid generator and a reactive compound, has the characteristic of being able to react at low temperatures.

[0004] Dual-type acid generators that generate acid not only by heat but also by light have also been reported (for example, Patent Documents 5 and 6). Patent Documents 5 and 6 disclose, as acid generators, onium salt compounds whose counter cation is benzothiazolium and whose counter anion is antimony.

[0005] However, the acid generators described in Patent Documents 5 and 6 above use highly toxic antimony, and further have the problem that they are soluble only in specific solvents. Furthermore, reactive compositions in which an acid generator is mixed with a reactive compound such as an epoxy may undergo a reaction during long-term storage, resulting in an increase in viscosity, and therefore, higher storage stability is required for such reactive compositions. Therefore, there is a strong demand for novel compounds having acid generating ability that are excellent in solubility in various solvents (hereinafter referred to as "solvent compatibility") and storage stability. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2009-013315 [Patent Document 2] Japanese Patent Application Laid-Open No. 2010-235862 [Patent Document 3] Japanese Patent Publication No. 2022-190822 [Patent Document 4] Japanese Patent Application Publication No. 2019-189698 [Patent Document 5] Japanese Patent Application Publication No. 02-268173 [Patent Document 6] Japanese Patent Application Publication No. 07-025863 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of the present disclosure is to provide a novel onium salt compound that has excellent solvent compatibility and excellent storage stability. [Means for solving the problem]

[0008] As a result of extensive research into achieving the above object, the present inventors discovered that the above problems can be solved by introducing a special structure into the counter anion of the onium salt, thereby completing the present invention.

[0009] That is, the present disclosure is as follows. Section 1. General formula (1):

[0010] [ka]

[0011] (In the formula, R A represents an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group. R 4 represents a hydrogen atom, a C1-15 alkyl group which may have a substituent, a C2-15 alkenyl group which may have a substituent, a C2-15 alkynyl group which may have a substituent, a 3-15-membered saturated or unsaturated carbocyclic group which may have a substituent, a C1-15 alkylcarbonyl group which may have a substituent, a carbonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have a substituent, a C1-15 alkoxycarbonyl group which may have a substituent, an oxycarbonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have a substituent, an aminocarbonyl group which may have a substituent, or a carboxyl group. R 5 and R 6are the same or different and are a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an oxy group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, an oxycarbonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted aminocarbonyl group, a carboxyl group, an optionally substituted amino group, a C1-15 alkylthio group, an optionally substituted thio group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group, a sulfinyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group, a sulfonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, or an optionally substituted heterocyclic group; Alternatively, the R 5 and R 6 These two groups may be bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent. The dotted lines indicate single or double bonds. X - represents a boron anion containing a fluorine-containing aromatic ring, a gallium anion containing a fluorine-containing aromatic ring, a carbon anion containing a fluorine-containing sulfonyl group, a cyclic sulfonimide anion having a fluorine atom, or a phosphorus anion containing a fluorine-containing alkyl group. An onium salt compound represented by the formula: Section 2. R A is represented by the following general formula (1-R A):

[0012] [ka]

[0013] (In the formula, R 1 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, or an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring oxycarbonyl a group, an optionally substituted aminocarbonyl group, a carboxyl group, an optionally substituted amino group, a C1-15 alkylthio group, an optionally substituted thio group having a 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group, an optionally substituted sulfinyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group, an optionally substituted sulfonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, a optionally substituted heterocyclic group, or a optionally substituted silyl group. R 2 represents a hydrogen atom, a halogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group. R 3 represents a hydrogen atom, a halogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group; Alternatively, the R1 , R 2 and R 3 Among these, two or three adjacent groups may be bonded to each other to form a saturated or unsaturated carbocyclic or heterocyclic ring. The saturated or unsaturated carbocyclic or heterocyclic ring may further have a substituent. * indicates the bonding position with the sulfur atom in the general formula (1). Item 2. The onium salt compound according to Item 1, wherein the group is represented by the formula: Section 3. R 1 represents a hydrogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring oxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring an aminocarbonyl group, a carboxyl group, an optionally substituted C1-15 alkylthio group, a thio group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group, a sulfinyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group, a sulfonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, a heterocyclic group, or a silyl group; R 2 represents a hydrogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group; R 3 represents a hydrogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group; Alternatively, the R 1 , R2 and R 3 Item 3. The onium salt compound according to Item 2, wherein two or three adjacent groups among the above may be bonded to each other to form a saturated or unsaturated carbocyclic or heterocyclic ring, and the saturated or unsaturated carbocyclic or heterocyclic ring may further have a substituent. Section 4. X - is represented by the general formula (XA1): - B(R X1 )a(R X2 )b Boron anion (In the formula, R X1 is a fluorine atom or C n F 2n+1 R X2 is an unsubstituted phenyl group, or a fluorine atom and C n F 2n+1 represents a phenyl group having at least one substituent selected from the group consisting of groups. n represents an integer of 1 to 15. a represents an integer of 0 to 3. b represents an integer of 1 to 4. a+b is 4. (However, in the case of the above R X2 When is an unsubstituted phenyl group, a is an integer of 1 to 3.); General formula (XC1): - C(R X5 )(R X6 )(R X7 ) carbon anion (In the formula, R X5 , R X6 and R X7 are the same or different, C t F 2t+1 a sulfonyl group having a group; or at least one C t F 2t+1 represents a phenylsulfonyl group having a group, and t represents an integer of 1 to 15; or General formula (XD1):

[0014] [ka]

[0015] 4. The onium salt compound according to any one of items 1 to 3, which is a fluorine atom-containing cyclic sulfonimide anion represented by the formula: (wherein r represents an integer of 1 to 6). Section 5. X - teeth, The following general formula (XA2):

[0016] [ka]

[0017] (In the formula, R 30 , R 31 , R 32 , R 33 and R 34 are the same or different and are a hydrogen atom, a fluorine atom, or C n F 2n+1 group, provided that the R 30 , R 31 , R 32 , R 33 and R 34 One of the following is a fluorine atom or C n F 2n+1 a group, and n represents an integer of 1 to 15; The following general formula (XC2):

[0018] [ka]

[0019] (In the formula, R 40 , R 41 and R 42 are the same or different, C t F 2t+1 represents a group, and t represents an integer of 1 to 15; or General formula (XD1):

[0020] [ka]

[0021] 5. The onium salt compound according to any one of items 1 to 4, which is a fluorine atom-containing cyclic sulfonimide anion represented by the formula: (wherein r represents an integer of 1 to 6). Section 6. R 5 and R 6 and these two groups are bonded to each other together with adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring, and the saturated or unsaturated carbocyclic ring may further have a substituent. Section 7. R 4 Item 7. The onium salt compound according to any one of Items 1 to 6, wherein is an unsubstituted C1 to C15 alkyl group. Section 8. Item 8. An acid generator containing the onium salt compound according to any one of Items 1 to 7. Section 9. Item 8. A polymerization initiator containing the onium salt compound according to any one of Items 1 to 7. Section 10. 8. A reactive composition containing the onium salt compound according to any one of items 1 to 7 and a reactive compound. Section 11. Item 11. A polymer obtained from the reactive composition according to item 10. Section 12. Item 11. An adhesive, sealant, or resist containing the reactive composition according to item 10. Section 13. Item 11. The reactive composition according to item 10, which is for use in an adhesive, a sealant, or a resist. Section 14. Item 8. Use of the onium salt compound according to any one of Items 1 to 7 as an acid generator. Section 15. Item 8. Use of the onium salt compound according to any one of Items 1 to 7 as a polymerization initiator. Section 16. Item 14. Use of the reactive composition according to item 10 or 13 for polymers. Section 17. Item 14. Use of the reactive composition according to item 10 or 13 for adhesives. Section 18. Item 14. Use of the reactive composition according to item 10 or 13 for a sealant. Section 19. Item 14. Use of the reactive composition according to item 10 or 13 for a resist.

[0022] In the case of inventions of products defined by manufacturing processes in this disclosure, it is currently impossible or impractically difficult to specify all of the components contained therein or the structure thereof, and therefore the inventions are described using product-by-process claims. [Effects of the Invention]

[0023] According to the present disclosure, it is possible to provide a novel onium salt compound that has excellent solvent compatibility and excellent storage stability. Furthermore, the onium salt compound of the present disclosure can function not only as an acid generator but also as a radical generator. DETAILED DESCRIPTION OF THE INVENTION

[0024] Hereinafter, embodiments of the present disclosure will be described in detail. Note that, unless otherwise specified, the terms used in the claims and specification are defined according to the definitions commonly used in the technical field.

[0025] Onium salt compounds The onium salt compound of the present disclosure is a compound represented by the following general formula (1): Hereinafter, the onium salt compound of the present disclosure may also be simply referred to as "onium salt" or the like.

[0026] [ka]

[0027] Here, R in the general formula (1) 4represents a hydrogen atom, a C1-15 alkyl group which may have a substituent, a C2-15 alkenyl group which may have a substituent, a C2-15 alkynyl group which may have a substituent, a 3-15-membered saturated or unsaturated carbocyclic group which may have a substituent, a C1-15 alkylcarbonyl group which may have a substituent, a carbonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have a substituent, a C1-15 alkoxycarbonyl group which may have a substituent, an oxycarbonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have a substituent, an aminocarbonyl group which may have a substituent, or a carboxyl group. Among them, the preferred R 4 Examples of the alkyl group include an optionally substituted C1-15 alkyl group and an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. More preferred R 4 The alkyl group is an unsubstituted C1-15 alkyl group. Even more preferable R 4 The alkyl group is an unsubstituted C1-6 alkyl group.

[0028] R 5 and R 6are the same or different and are a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an oxy group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, an oxycarbonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted aminocarbonyl group, a carboxyl group, an optionally substituted amino group, a C1-15 alkylthio group, an optionally substituted thio group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group, a sulfinyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group, a sulfonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, or an optionally substituted heterocyclic group; Alternatively, the R 5 and R 6 These two groups may be bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent.

[0029] Among them, the preferred R 5 The groups are a hydrogen atom, a halogen atom, a nitro group, a cyano group, and a C1 to C15 alkyl group which may have a substituent. More preferred R 5 is a hydrogen atom or a C1-15 alkyl group which may have a substituent. Even more preferable R 5 is a hydrogen atom or an unsubstituted C1-6 alkyl group. Among them, the preferred R 6 The groups are a hydrogen atom, a halogen atom, a nitro group, a cyano group, and a C1 to C15 alkyl group which may have a substituent. More preferred R 6 is a hydrogen atom or a C1-15 alkyl group which may have a substituent. Even more preferable R 6 is a hydrogen atom or an unsubstituted C1-6 alkyl group.

[0030] Alternatively, the R 5 and R 6 These two groups may be bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent.

[0031] R 5 and R 6 When each of these groups is bonded to the adjacent carbon atom to form a saturated or unsaturated carbocyclic ring, the saturated or unsaturated carbocyclic ring is preferably a benzene ring (also called a phenyl ring) or a naphthalene ring. Here, the compound represented by general formula (1) in which the saturated or unsaturated carbocyclic ring is a benzene ring means a compound having a benzothiazole ring. When the saturated or unsaturated carbocyclic ring is a naphthalene ring, the compound represented by general formula (1) refers to a compound having a naphthothiazole ring. Examples of the naphthalene ring include 1,2-naphthalene, 2,3-naphthalene, and 3,4-naphthalene. The saturated or unsaturated carbocyclic ring is more preferably a benzene ring.

[0032] The dotted lines indicate single or double bonds.

[0033] X -represents a boron anion containing a fluorine-containing aromatic ring, a gallium anion containing a fluorine-containing aromatic ring, a carbon anion containing a fluorine-containing sulfonyl group, a cyclic sulfonimide anion having a fluorine atom, or a phosphorus anion containing a fluorine-containing alkyl group.

[0034] R A represents an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group.

[0035] R A is represented by the following general formula (1-R A ):

[0036] [ka]

[0037] A group represented by the following formula is preferred.

[0038] Here, the general formula (1-R A ) in R 1represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, or an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring oxycarbonyl a group, an optionally substituted aminocarbonyl group, a carboxyl group, an optionally substituted amino group, a C1-15 alkylthio group, an optionally substituted thio group having a 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group, an optionally substituted sulfinyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group, an optionally substituted sulfonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, a optionally substituted heterocyclic group, or a optionally substituted silyl group.

[0039] Among them, the preferred R 1Examples thereof include a hydrogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring oxycarbonyl group, and optionally substituted aminocarbonyl groups, carboxyl groups, C1-15 alkylthio groups, optionally substituted thio groups having a 3-15-membered saturated or unsaturated carbocyclic ring, C1-15 alkylsulfinyl groups, optionally substituted sulfinyl groups having a 3-15-membered saturated or unsaturated carbocyclic ring, optionally substituted C1-15 alkylsulfonyl groups, sulfonyl groups having a 3-15-membered saturated or unsaturated carbocyclic ring, optionally substituted heterocyclic groups, and optionally substituted silyl groups.

[0040] More preferred R 1Examples of the alkyl group include a hydrogen atom, a C1-15 alkyl group optionally having one or more substituents selected from <Group 1> below, a C2-15 alkenyl group optionally having one or more substituents selected from <Group 1> below, a C2-15 alkynyl group optionally having one or more substituents selected from <Group 1> below, a 3-15-membered saturated or unsaturated carbocyclic group optionally having one or more substituents selected from <Group 3> below, a C1-15 alkylcarbonyl group optionally having one or more substituents selected from <Group 1> below, a carbonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring optionally having one or more substituents selected from <Group 3> below, a C1-15 alkoxycarbonyl group optionally having one or more substituents selected from <Group 1> below, an oxycarbonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring optionally having one or more substituents selected from <Group 3> below, an aminocarbonyl group which may have a substituent, a carboxyl group, a C1-15 alkylthio group which may have one or more substituents selected from <Group 1> below, a thio group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 3> below, a C1-15 alkylsulfinyl group which may have one or more substituents selected from <Group 1> below, a sulfinyl group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 3> below, a C1-15 alkylsulfonyl group which may have one or more substituents selected from <Group 1> below, a sulfonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 3> below, a heterocyclic group which may have one or more substituents selected from <Group 3> below, and a silyl group which may have one or more substituents selected from <Group 6> below.

[0041] Even more preferable R 1Examples thereof include a hydrogen atom, a C1-15 alkyl group optionally having one or more substituents selected from <Group 2> below, a C2-15 alkenyl group optionally having one or more substituents selected from <Group 2> below, a C2-15 alkynyl group optionally having one or more substituents selected from <Group 2> below, a 3-15-membered saturated or unsaturated carbocyclic group optionally having one or more substituents selected from <Group 4> below, a C1-15 alkylcarbonyl group optionally having one or more substituents selected from <Group 2> below, a carbonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring optionally having one or more substituents selected from <Group 4> below, a C1-15 alkoxycarbonyl group optionally having one or more substituents selected from <Group 2> below, an oxycarbonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring optionally having one or more substituents selected from <Group 4> below, an aminocarbonyl group which may have a substituent, a carboxyl group, a C1-15 alkylthio group which may have one or more substituents selected from <Group 2> below, a thio group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 4> below, a C1-15 alkylsulfinyl group which may have one or more substituents selected from <Group 2> below, a sulfinyl group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 4> below, a C1-15 alkylsulfonyl group which may have one or more substituents selected from <Group 2> below, a sulfonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 4> below, a heterocyclic group which may have one or more substituents selected from <Group 4> below, and a silyl group which may have one or more substituents selected from <Group 6> below.

[0042] R 2 represents a hydrogen atom, a halogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group. Among them, the preferred R2 is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 1> below, or a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 3> below. More preferred R 2 is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below.

[0043] R 3 represents a hydrogen atom, a halogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. Among them, the preferred R 3 is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 1> below, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 3> below. More preferred R 3 is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below.

[0044] Alternatively, the R 1 , R 2 and R 3 Among these, two or three adjacent groups may be bonded to each other to form a saturated or unsaturated carbocyclic or heterocyclic ring. The saturated or unsaturated carbocyclic or heterocyclic ring may further have a substituent.

[0045] A preferred saturated or unsaturated carbocyclic ring is a C3-15 carbocyclic ring which may have at least one substituent selected from the following <Group 3>. More preferred saturated or unsaturated carbocyclic rings are C3-15 carbocyclic rings which may have at least one substituent selected from the following <Group 4>. More preferred saturated or unsaturated carbocyclic rings include indene, which may have one or more substituents selected from the group consisting of substituted or unsubstituted phenyl groups and oxo groups; fluorene, which may have one or more substituents selected from the group consisting of substituted or unsubstituted phenyl groups and oxo groups; adamantane, which may have one or more substituents selected from the group consisting of substituted or unsubstituted phenyl groups and oxo groups; cyclopentane, which may have one or more substituents selected from the group consisting of substituted or unsubstituted phenyl groups and oxo groups; and cyclopentene, which may have one or more substituents selected from the group consisting of substituted or unsubstituted phenyl groups and oxo groups.

[0046] Preferred heterocycles are heterocycles which may have at least one substituent selected from the following <Group 3>. More preferred heterocycles are heterocycles which may have at least one substituent selected from the following <Group 4>. A more preferred heterocycle is succinimide (maleimide) which may have one or more substituents selected from the group consisting of a substituted or unsubstituted phenyl group and an oxo group.

[0047] * indicates the bonding position to the sulfur atom in the general formula (1).

[0048] X - is a boron anion containing a fluorine-containing aromatic ring (XA - ), fluorine-containing aromatic ring-containing gallium anion (XB - ), carbon anions containing fluorine-containing sulfonyl groups (XC - ), fluorine atom-containing cyclic sulfonimide anion (XD - ), or phosphorus anion containing a fluorine-containing alkyl group (XE - This can also be said to be.

[0049] Here, the preferred X - Examples of the compound include compounds represented by the general formula (XA1): - B(R X1 )a(R X2 )b Boron anion (In the formula, R X1 is a fluorine atom or C n F 2n+1 R X2 is an unsubstituted phenyl group, or a fluorine atom and C n F 2n+1 represents a phenyl group having at least one substituent selected from the group consisting of groups. n represents an integer of 1 to 15. a represents an integer of 0 to 3. b represents an integer of 1 to 4. a+b is 4. (However, in the case of the above R X2 When is an unsubstituted phenyl group, a is an integer of 1 to 3.);

[0050] General formula (XB1): - Ga(R X3 )a(R X4 )b, a gallium anion (In the formula, R X3 is a fluorine atom or C n F 2n+1 R X4 is an unsubstituted phenyl group, or a fluorine atom and C n F 2n+1 represents a phenyl group having at least one substituent selected from the group consisting of groups; n represents an integer of 1 to 15; a represents an integer of 0 to 3; b represents an integer of 1 to 4; a+b is 4);

[0051] General formula (XC1): - C(R X5 )(R X6 )(R X7 ) carbon anion (In the formula, R X5 , R X6 and R X7 are the same or different, C t F 2t+1 a sulfonyl group having a group; or at least one C tF 2t+1 represents a phenylsulfonyl group having a group; and t represents an integer of 1 to 15;

[0052] General formula (XD1):

[0053] [ka]

[0054] (wherein r represents an integer of 1 to 6); or

[0055] General formula (XE1):P(R X8 )c(R X9 ) Phosphorus anion containing a fluorine-containing alkyl group represented by d (In the formula, R X8 is C u F 2u+1 R X9 represents a fluorine atom. u represents an integer of 1 to 15. c represents an integer of 1 to 6. d represents an integer of 0 to 5. c+d represents 6.

[0056] More preferred boron anions represented by XA1 include: The following general formula (XA2):

[0057] [ka]

[0058] (In the formula, R 30 , R 31 , R 32 , R 33 and R 34 are the same or different and are a hydrogen atom, a fluorine atom, or C n F 2n+1 group, provided that the R 30 , R 31 , R 32 , R 33 and R 34 One of the following is a fluorine atom or C nF 2n+1 It is a group, and n represents an integer of 1 to 15. It is a boron anion represented by the following formula:

[0059] Here, the substituent R in the general formula (XA2) 30 , R 31 , R 32 , R 33 and R 34 The preferred groups are shown below. Preferred R 30 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group. Preferred R 31 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group. Preferred R 32 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group. Preferred R 33 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group. Preferred R 34 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group.

[0060] Among the boron anions represented by the general formula (XA2), a more preferred combination of substituents is R 30 is a fluorine atom, R 31 is a fluorine atom, R 32 is a fluorine atom, R 33 is a fluorine atom, and R 34 is a fluorine atom; R 30 is a hydrogen atom, R 31 is a hydrogen atom, R 32 is a fluorine atom, R 33 is a hydrogen atom, and R 34 is a hydrogen atom; R 30 is a trifluoromethyl group, R 31 is a trifluoromethyl group, R 32 is a trifluoromethyl group, R 33 is a trifluoromethyl group, and R 34 is a trifluoromethyl group; R 30is a hydrogen atom, R 31 is a trifluoromethyl group, R 32 is a hydrogen atom, R 33 is a trifluoromethyl group, and R 34 is a hydrogen atom; R 30 is a hydrogen atom, R 31 is a hydrogen atom, R 32 is a trifluoromethyl group, R 33 is a hydrogen atom, and R 34 is a hydrogen atom.

[0061] Even more preferred boron anions represented by the general formula (XA2) are the boron anions represented by the following general formulas (XA2-1), (XA2-2), and (XA2-3).

[0062] [ka]

[0063] More preferred gallium anions represented by XB1 include: The following general formula (XB2):

[0064] [ka]

[0065] (In the formula, R 35 , R 36 , R 37 , R 38 and R 39 are the same or different and are a hydrogen atom, a fluorine atom, or C n F 2n+1 group, provided that the R 35 , R 36 , R 37 , R 38 and R 39 One of the following is a fluorine atom or C n F 2n+1 It is a group, and n represents an integer of 1 to 15. It is a gallium anion represented by the following formula:

[0066] Here, the substituent R in the general formula (XB2) 35 , R 36 , R 37 , R 38 and R 39 The preferred groups are shown below. Preferred R 35 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group. Preferred R 36 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group. Preferred R 37 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group. Preferred R 38 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group. Preferred R 39 are a hydrogen atom, a fluorine atom, and a trifluoromethyl group.

[0067] Among the boron anions represented by the general formula (XB2), a more preferred combination of substituents is R 35 is a fluorine atom, R 36 is a fluorine atom, R 37 is a fluorine atom, R 38 is a fluorine atom, and R 39 is a fluorine atom; R 35 is a hydrogen atom, R 36 is a hydrogen atom, R 37 is a fluorine atom, R 38 is a hydrogen atom, and R 39 is a hydrogen atom; R 35 is a trifluoromethyl group, R 36 is a trifluoromethyl group, R 37 is a trifluoromethyl group, R 38 is a trifluoromethyl group, and R 39 is a trifluoromethyl group; R 35 is a hydrogen atom, R 36 is a trifluoromethyl group, R 37 is a hydrogen atom, R38 is a trifluoromethyl group, and R 39 is a hydrogen atom; R 35 is a hydrogen atom, R 36 is a hydrogen atom, R 37 is a trifluoromethyl group, R 38 is a hydrogen atom, and R 39 is a hydrogen atom.

[0068] More preferred carbon anions (also called methide anions) represented by XC1 include: The following general formula (XC2):

[0069] [ka]

[0070] (In the formula, R 40 , R 41 and R 42 are the same or different, C t F 2t+1 represents a group, and t represents an integer of 1 to 15.

[0071] Here, the substituent R in the general formula (XC2) 40 , R 41 and R 42 The preferred groups are shown below. Preferred R 40 is a difluoromethyl group, a trifluoromethyl group, or a pentafluoroethyl group. Preferred R 41 is a difluoromethyl group, a trifluoromethyl group, or a pentafluoroethyl group. Preferred R 42 is a difluoromethyl group, a trifluoromethyl group, or a pentafluoroethyl group. Particularly preferred combinations of carbon anions include R 40 is a trifluoromethyl group, R 41 is a trifluoromethyl group, and R 42 is a trifluoromethyl group.

[0072] Even more preferred examples of the carbon anion represented by the general formula (XC2) include: The following general formula (XC2-1):

[0073] [ka]

[0074] It is a carbon anion represented by the formula:

[0075] More preferred cyclic sulfonimide anions represented by general formula (XD1) are those in which r is an integer of 2 to 5.

[0076] Even more preferred cyclic sulfonimide anions represented by the general formula (XD1) include cyclic sulfonimide anions represented by the following general formula (XD1-1) and cyclic sulfonimide anions represented by the following general formula (XD1-2).

[0077] [ka]

[0078] General formula (XE1):P(R X8 )c(R X9 )d, the phosphorus anion containing a fluorine-containing alkyl group is (CF3CF2)2PF4 - , (CF3CF2)3PF3 - , ((CF3)2CF)2PF4 - , ((CF3)2CF)3PF3 - , (CF3CF2CF2)2PF4 - , (CF3CF2CF2)3PF3 - , ((CF3)2CFCF2)2PF4 - , ((CF3)2CFCF2)3PF3 - , (CF3CF2CF2CF2)2PF4 - , and (CF3CF2CF2CF2)3PF3 -Examples of the anion include anions represented by the following formula: Among these, the preferred phosphorus anion containing a fluorine-containing alkyl group is (CF3CF2)3PF3 - , (CF3CF2CF2)3PF3 - , ((CF3)2CF)3PF3 - , ((CF3)2CF)2PF4 - , ((CF3)2CFCF2)3PF3 - , and ((CF3)2CFCF2)2PF4 - It is an anion represented by the formula:

[0079] Incidentally, Japanese Patent Laid-Open No. 2007-224183 (Patent Document 7) describes an energy ray-sensitive acid generator (Claim 1). In addition, paragraph

[0192] of the same document describes 2-methylthio-3-benzylbenzothiazolium tetrakis(pentafluorophenyl)borate (1Z-1) and 2-methylthio-3-benzylbenzothiazolium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (1Z-2) in a single line, but the examples section of the document does not mention them. The document does not disclose how the above-mentioned compounds (1Z-1) and (1Z-2) were produced and what effects were obtained, so it cannot be said that the document discloses the above-mentioned invention. The onium salt compounds of the present disclosure preferably exclude compounds represented by the following formula (1Z-1) and formula (1Z-2).

[0080] [ka]

[0081] In addition, preferred onium salt compounds are compounds represented by the following general formula (1A-1), compounds represented by general formula (1A-2), compounds represented by general formula (1A-3), and compounds represented by general formula (1A-4).

[0082] Among the onium salt compounds represented by the general formula (1), the R5 and R 6 However, when the compound does not form a saturated or unsaturated carbocyclic ring, the compound is a compound represented by the following general formula (1A-1) or a compound represented by the following general formula (1A-2).

[0083] [ka]

[0084] Here, R in general formula (1A-1) and general formula (1A-2) A , R 4 and X - is the same as above. R 5 and R 6 are the same or different and are a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an oxy group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, and a heterocyclic group which may have a substituent.

[0085] In addition, among the onium salt compounds represented by the general formula (1), 5 and R 6 are bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring, the onium salt compound is represented by the following general formula (1A-3) (hereinafter, may be referred to as a "benzothiazolium salt"), or the onium salt compound is represented by the following general formula (1A-4).

[0086] [ka]

[0087] (In the formula, R A , R 4 and X - is the same as above. R 7 , R 8 , R 9 and R 10are the same or different and are a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an oxy group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, and a heterocyclic group which may have a substituent. Alternatively, the R 7 , R 8 , R 9 and R 10 At least two of the groups may be bonded to each other together with adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent.

[0088] Preferred R 7 is one or more substituents selected from <Group 3>. More preferred R 7 is one or more substituents selected from <Group 4>. Preferred R 8 is one or more substituents selected from <Group 3>. More preferred R 8 is one or more substituents selected from <Group 4>. Preferred R 9 is one or more substituents selected from <Group 3>. More preferred R 9 is one or more substituents selected from <Group 4>. Preferred R 10 is one or more substituents selected from <Group 3>. More preferred R 10 is one or more substituents selected from <Group 4>.

[0089] [ka]

[0090] (In the formula, R A , R 4 and X - is the same as above. R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20are the same or different and are a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an oxy group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, and a heterocyclic group which may have a substituent. Alternatively, the R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 At least two of the groups may be bonded to each other together with adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent.

[0091] In the present disclosure, a preferred onium salt is a compound represented by the following general formula (1B).

[0092] [ka]

[0093] Here, R in the formula 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X - and dotted lines are the same as above.

[0094] Examples of the compound represented by the general formula (1B) include a compound represented by the following general formula (1B-1), a compound represented by the general formula (1B-2), a compound represented by the general formula (1B-3), and a compound represented by the general formula (1B-4).

[0095] [ka]

[0096] Here, R in the formula 1 , R 2 , R 3 , R 4 , R 5 , R 6 and X - is the same as above.

[0097] [ka]

[0098] Here, R in the formula 1 , R 2 , R 3 , R 4 , R 5 , R 6 and X - is the same as above.

[0099] [ka]

[0100] where R1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 and X - is the same as above.

[0101] [ka]

[0102] where R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 and X - is the same as above.

[0103] Among the compounds represented by the general formula (1B), more preferred onium salt compounds include, for example, compounds represented by the following general formula (1C). [ka]

[0104] Here, R in general formula (1C) 4 , R 5 , R 6 , dotted line and X - is the same as above. In addition, the R 21 , R 22 , R 23 , R 24 and R 25are the same or different and represent a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an oxy group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, and a heterocyclic group which may have a substituent. R 26 represents a hydrogen atom, a halogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group. R 27 represents a hydrogen atom, a halogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. q represents an integer of 1 to 6. When q is an integer of 2 to 6, two or more R 26 may be the same or different, and two or more R 27may be the same or different. In addition, the onium salt compounds encompassed by the present disclosure may be optical isomers.

[0105] Examples of the compound represented by the general formula (1C) include a compound represented by the following general formula (1C-1), a compound represented by the general formula (1C-2), a compound represented by the general formula (1C-3), and a compound represented by the general formula (1C-4).

[0106] [ka]

[0107] Here, R in the formula 4 , R 5 , R 6 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , q and X - is the same as above.

[0108] [ka]

[0109] Here, R in the formula 4 , R 5 , R 6 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , q and X - is the same as above.

[0110] [ka]

[0111] Here, R in the formula 4 , R7 , R 8 , R 9 , R 10 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , q and X - is the same as above.

[0112] [ka]

[0113] Here, R in the formula 4 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , q and X - is the same as above.

[0114] Preferred R 21 , R 22 , R 23 , R 24 and R 25 are the same or different and are a hydrogen atom, a halogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted C1-15 alkylcarbonyl group, and an optionally substituted C1-15 alkoxycarbonyl group. More preferred R 21 , R22 , R 23 , R 24 and R 25 are the same or different and are a hydrogen atom, a hydroxyl group, a C1-15 alkyl group optionally having one or more substituents selected from <Group 2> below, a C2-15 alkenyl group optionally having one or more substituents selected from <Group 2> below, a C2-15 alkynyl group optionally having one or more substituents selected from <Group 2> below, a 3-15 membered saturated or unsaturated carbocyclic group optionally having one or more substituents selected from <Group 4> below, a C1-15 alkoxy group optionally having one or more substituents selected from <Group 2> below, a C1-15 alkylcarbonyl group optionally having one or more substituents selected from <Group 2> below, and a C1-15 alkoxycarbonyl group optionally having one or more substituents selected from <Group 2> below.

[0115] Preferred R 26 The substituents are a hydrogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, and an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. More preferred R 26 is a hydrogen atom, a hydroxyl group, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below.

[0116] Preferred R 27 The substituents are a hydrogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, and an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. More preferred R 27 is a hydrogen atom, a hydroxyl group, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below.

[0117] q is an integer of 1 to 6, preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

[0118] Among the compounds represented by the general formula (1B), more preferred onium salt compounds include, for example, compounds represented by the following general formula (1D). [ka]

[0119] Here, R in general formula (1D) 4 , R 5 , R 6 , dotted line and X - is the same as above. In addition, the R 50 , R 51 and R 52are the same or different and are a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an oxy group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylcarbonyl group, a carbonyl group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkoxycarbonyl group, and a heterocyclic group which may have a substituent. R 53 represents a hydrogen atom, a halogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group. R 54 represents a hydrogen atom, a halogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. q represents an integer of 1 to 6. When q is an integer of 1, the R 53 or R 54 and the R 50and may be bonded to each other together with the adjacent carbon atoms to form an unsaturated carbocyclic ring. The unsaturated carbocyclic ring may further have a substituent. When q is an integer between 2 and 6, two or more R 53 may be the same or different, and two or more R 54 may be the same or different.

[0120] Examples of the compound represented by general formula (1D) include compounds represented by the following general formulas (1D-1), (1D-2), (1D-3), and (1D-4).

[0121] [ka]

[0122] Here, R in the formula 4 , R 5 , R 6 , R 50 , R 51 , R 52 , R 53 , R 54 , q and X - is the same as above.

[0123] [ka]

[0124] Here, R in the formula 4 , R 5 , R 6 , R 50 , R 51 , R 52 , R 53 , R 54 , q and X - is the same as above.

[0125] [ka]

[0126] Here, R in the formula 4 , R 7 , R 8 , R 9 , R 10 , R 50 , R 51 , R 52 , R 53 , R 54 , q and X - is the same as above.

[0127] [ka]

[0128] Here, R in the formula 4 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 50 , R 51 , R 52 , R 53 , R 54 , q and X - is the same as above.

[0129] Preferred R 50 , R 51 , R 52 , R 53 and R 54 are the same or different and are a hydrogen atom, a halogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted C1-15 alkylcarbonyl group, and an optionally substituted C1-15 alkoxycarbonyl group. More preferred R 50 , R51 , R 52 , R 53 and R 54 are the same or different and are a hydrogen atom, a C1-15 alkyl group optionally having one or more substituents selected from <Group 2> below, a C2-15 alkenyl group optionally having one or more substituents selected from <Group 2> below, a C2-15 alkynyl group optionally having one or more substituents selected from <Group 2> below, a 3-15 membered saturated or unsaturated carbocyclic group optionally having one or more substituents selected from <Group 4> below, a C1-15 alkoxy group optionally having one or more substituents selected from <Group 2> below, a C1-15 alkylcarbonyl group optionally having one or more substituents selected from <Group 2> below, and a C1-15 alkoxycarbonyl group optionally having one or more substituents selected from <Group 2> below.

[0130] Preferred R 53 The substituents are a hydrogen atom, an optionally substituted C1-15 alkyl group, and an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. More preferred R 53 is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below.

[0131] Preferred R 54 represents a hydrogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. More preferred R 54 is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below.

[0132] q is an integer of 1 to 6, preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

[0133] Among the compounds represented by the general formula (1B), more preferred onium salt compounds include, for example, compounds represented by the following general formula (1E).

[0134] [ka]

[0135] Here, R in general formula (1D) 4 , R 5 , R 6 , dotted line, and X - is the same as above. In addition, the R 60 represents a hydrogen atom, a C1-15 alkyl group which may have a substituent, a C2-15 alkenyl group which may have a substituent, a C2-15 alkynyl group which may have a substituent, a C1-15 alkoxy group which may have a substituent, an oxy group having a 3-15-membered saturated or unsaturated carbocyclic ring which may have a substituent, an aryl group which may have a substituent, or a heterocyclic group which may have a substituent. R 61 , R 62 and R 63 are the same or different and represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted C1-15 alkoxy group, an optionally substituted oxy group having a 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted aryl group, or an optionally substituted heterocyclic group.

[0136] Examples of the compound represented by general formula (1E) include a compound represented by the following general formula (1E-1), a compound represented by general formula (1E-2), a compound represented by general formula (1E-3), and a compound represented by general formula (1E-4).

[0137] [ka]

[0138] Here, R in the formula 4 , R 5 , R 6 , R 60 , R 61 , R 62 , R 63 and X - is the same as above.

[0139] [ka]

[0140] Here, R in the formula 4 , R 5 , R 6 , R 60 , R 61 , R 62 , R 63 and X - is the same as above.

[0141] [ka]

[0142] Here, R in the formula 4 , R 7 , R 8 , R 9 , R 10 , R 60 , R 61 , R 62 , R 63 and X - is the same as above.

[0143] [ka]

[0144] Here, R in the formula 4 , R 11 , R 12 , R 13, R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 60 , R 61 , R 62 , R 63 and X - is the same as above.

[0145] Preferred R 60 The substituents are a hydrogen atom, an optionally substituted C1-15 alkyl group, and an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. More preferred R 60 is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below.

[0146] Preferred R 61 is a hydrogen atom or a C1-15 alkyl group which may have a substituent. More preferred R 61 is a hydrogen atom and a C1-15 alkyl group which may have one or more substituents selected from the following <Group 2>.

[0147] Preferred R 62 is a hydrogen atom or a C1-15 alkyl group which may have a substituent. More preferred R 62 is a hydrogen atom and a C1-15 alkyl group which may have one or more substituents selected from the following <Group 2>.

[0148] Preferred R 63 is a hydrogen atom or a C1-15 alkyl group which may have a substituent. More preferred R 63is a hydrogen atom and a C1-15 alkyl group which may have one or more substituents selected from the following <Group 2>.

[0149] Among the onium salt compounds represented by the above general formula (1), preferred compounds are: R A is an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group; R 4 is an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted C1-15 alkylcarbonyl, R 5 and R 6 are the same or different and each represents a hydrogen atom or an optionally substituted C1-15 alkyl group; Alternatively, the R 5 and R 6 may be bonded to each other together with adjacent carbon atoms to form an unsaturated carbocyclic ring, which may further have a substituent; The dotted line is a single or double bond; X - is an onium salt compound in which the anion is a boron anion containing a fluorine-containing aromatic ring, a gallium anion containing a fluorine-containing aromatic ring, a carbon anion containing a fluorine-containing sulfonyl group, a cyclic sulfonimide anion having a fluorine atom, or a phosphorus anion containing a fluorine-containing alkyl group.

[0150] Among the onium salt compounds represented by the general formula (1), more preferred compounds are onium salt compounds represented by the general formula (1A-3), and specifically, 5 and R 6However, these two groups are bonded to each other together with the adjacent carbon atoms to form an unsaturated carbocyclic ring, and the unsaturated carbocyclic ring is a compound which may further have a substituent.

[0151] Among the onium salt compounds represented by the above general formula (1), more preferred compounds are the onium salt compounds represented by the above general formula (1A-3): R A is a C1-15 alkyl group optionally having one or more substituents selected from <Group 1>, a C2-15 alkenyl group optionally having one or more substituents selected from <Group 1>, a C2-15 alkynyl group optionally having one or more substituents selected from <Group 1>, a 3-15 membered saturated or unsaturated carbocyclic group optionally having one or more substituents selected from <Group 3>, or a heterocyclic group optionally having one or more substituents selected from <Group 3>; R 4 is a C1-15 alkyl group optionally having one or more substituents selected from <Group 1>, or a 3-15-membered saturated or unsaturated carbocyclic group optionally having one or more substituents selected from <Group 3>; R 7 is one or more substituents selected from <Group 3>; R 8 is one or more substituents selected from <Group 3>; R 9 is one or more substituents selected from <Group 3>; R 10 is one or more substituents selected from <Group 3>; Alternatively, the R 7 , R 8 , R 9 and R 10 At least two of the groups may be bonded to each other together with adjacent carbon atoms to form a phenyl ring, and the phenyl ring may further have one or more substituents selected from <Group 3>; X -is an onium salt compound which is a boron anion represented by the above general formula (XA2), a gallium anion represented by the above general formula (XB2), a carbon anion represented by the above general formula (XC2), or a cyclic sulfonimide anion represented by the above general formula (XD1).

[0152] Among the onium salt compounds represented by the general formula (1A-3), particularly preferred onium salts are R A is a C1-15 alkyl group optionally having one or more substituents selected from <Group 2>, a C2-15 alkenyl group optionally having one or more substituents selected from <Group 2>, a C2-15 alkynyl group optionally having one or more substituents selected from <Group 2>, a 3-15 membered saturated or unsaturated carbocyclic group optionally having one or more substituents selected from <Group 4>, or a heterocyclic group optionally having one or more substituents selected from <Group 4>; R 4 is a C1-15 alkyl group optionally having one or more substituents selected from <Group 2>, or a 3-15-membered saturated or unsaturated carbocyclic group optionally having one or more substituents selected from <Group 4>; R 7 is one or more substituents selected from <Group 4>; R 8 is one or more substituents selected from <Group 4>; R 9 is one or more substituents selected from <Group 4>; R 10 is one or more substituents selected from <Group 4>; Alternatively, the R 7 , R 8 , R 9 and R 10 At least two of the groups may be bonded to each other together with adjacent carbon atoms to form a phenyl ring, and the phenyl ring may further have one or more substituents selected from <Group 4>; X -is an onium salt compound which is a boron anion represented by the above general formula (XA2), a gallium anion represented by the above general formula (XB2), a carbon anion represented by the above general formula (XC2), or a cyclic sulfonimide anion represented by the above general formula (XD1).

[0153] The following provides definitions of terms used in this specification.

[0154] The notation Cx to y can be rephrased as Cx to Cy, or the number of carbon atoms x to y. The description Cx-Cy means that there are x to y carbon atoms, where x and y represent integers, and it is understood that all integers between x and y are also individually disclosed. For example, C1-15 means 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, C1-6 means 1, 2, 3, 4, 5, or 6 carbon atoms, C1-3 means 1, 2, or 3 carbon atoms, and C2-15 means 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms. C1-6 means 1, 2, 3, 4, 5, or 6 carbon atoms, C2-3 means 2 or 3 carbon atoms, 3-15 membered (C3-15 ring) means a 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13-, 14-, or 15-membered cyclic compound, and 3-7 membered (C3-7 ring) means a 3-, 4-, 5-, 6-, or 7-membered cyclic compound.

[0155] The phrase "optionally having a substituent" means that the group is substituted or unsubstituted. When the number of substituents is not specified, the number of substituents is one or more, i.e., one or more.

[0156] The halogen atom is not particularly limited, and specific examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0157] The carbon chain in "alkyl", "alkenyl", "alkynyl", "alkoxy", etc. may be a straight chain or branched chain.

[0158] The C1-15 alkyl group is not particularly limited, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, a 1,2-dimethylpropyl group, a hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 1,1-dimethylbutyl group, a 2,2-dimethylbutyl group, a 3,3-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, a 1-isopropylpropyl group, a 1,1,2-trimethylpropyl group, a 1,2,2-trimethylpropyl group, etc. In this specification, n- means normal, sec- means secondary, t- means tertiary, and i- means iso.

[0159] The C2-15 alkenyl group refers to a linear or branched unsaturated hydrocarbon group having one or more double bonds. When geometric isomers exist, they are either the E- or Z-isomer, or a mixture of the E- and Z-isomers in any ratio, and are not particularly limited as long as they are within the specified C range. The C2-15 alkenyl group is not particularly limited, and specific examples include a vinyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 3-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 4-methyl-3-pentenyl group, a 3-methyl-2-pentenyl group, a 1-methylvinyl group, a 2-methylvinyl group, a 1,2-dimethylvinyl group, a 2,2-dimethylvinyl group, and a 1,2,2-trimethylvinyl group. Examples of the substituted C2-15 alkenyl group include a 1-phenylvinyl group and a 2-phenylvinyl group.

[0160] The C2-15 alkynyl group refers to a linear or branched unsaturated hydrocarbon group having one or more triple bonds. The C2-15 alkynyl group is not particularly limited, and specific examples include an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1,1-dimethyl-2-propynyl group, a 1-hexynyl group, a 2-hexynyl group, a 3-hexynyl group, a 4-hexynyl group, and a 5-hexynyl group.

[0161] The C1-15 alkoxy group refers to the aforementioned C1-15 alkyl group bonded via an oxygen atom. The C1-15 alkoxy group is not particularly limited, and specific examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group, a pentyloxy group, an isopentyloxy group, a 1-methylbutoxy group, a 2-methylbutoxy group, a neopentyloxy group, a 1-ethylpropyloxy group, a 1,2-dimethylpropyloxy group, a hexyloxy group, and a 1-methylpentyloxy group. Examples thereof include a 2-methylpentyloxy group, a 3-methylpentyloxy group, a 4-methylpentyloxy group, a 1,1-dimethylbutoxy group, a 2,2-dimethylbutoxy group, a 3,3-dimethylbutoxy group, a 1,2-dimethylbutoxy group, a 1,3-dimethylbutoxy group, a 2,3-dimethylbutoxy group, a 2-ethylbutoxy group, a 1-isopropylpropyloxy group, a 1,1,2-trimethylpropyloxy group, and a 1,2,2-trimethylpropyloxy group.

[0162] The oxy group having a 3- to 15-membered saturated or unsaturated carbocyclic ring means the aforementioned 3- to 15-membered saturated or unsaturated carbocyclic ring bonded via an oxycarbonyl. The oxycarbonyl group having a 3- to 15-membered saturated or unsaturated carbon ring is not particularly limited, and specific examples thereof include oxy groups having a saturated carbon ring such as a cyclopropyloxy group and a cyclohexyloxy group; and oxy groups having an unsaturated carbon ring such as a cyclopropenyloxy group, a cyclohexenyloxy group, and a phenoxy group.

[0163] The 3- to 15-membered saturated or unsaturated carbocyclic group is not particularly limited, and examples thereof include a 3- to 15-membered cycloalkyl group, a 3- to 15-membered cycloalkenyl group, and a C6-14 aryl group.

[0164] The C3-15 cycloalkyl group is not particularly limited, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. The C3-15 cycloalkyl group may be substituted with an oxo group. Examples of the C3-15 cycloalkyl group substituted with an oxo group include cyclopentan-3-one and cyclohexane-3-one.

[0165] The C3-15 cycloalkenyl group is not particularly limited, and examples thereof include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, etc. The position of the double bond in the C3-C8 cycloalkenyl group is not particularly limited.

[0166] The C6-14 aryl group is not particularly limited and examples thereof include a phenyl group, a naphthyl group, an anthracenyl group, an indenyl group, an acenaphthynyl group, an acenaphthenyl group, a fluorenyl group, a phenanthrenyl group, an azulenyl group, etc. The aryl group can be rephrased as an aromatic hydrocarbon group. Examples of the substituted C6-14 aryl group include a tolyl group, a xylyl group, a mesityl group, and a biphenyl group.

[0167] The heterocyclic group is not particularly limited, and examples thereof include saturated or unsaturated heterocyclic groups. Examples of saturated or unsaturated heterocyclic groups include 5- to 7-membered saturated or unsaturated heterocyclic groups having 1 to 6 atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom.

[0168] The saturated heterocyclic group is not particularly limited and includes not only saturated heterocyclic groups but also non-aromatic heterocyclic groups. Examples of saturated heterocyclic groups include 4- to 6-membered monocyclic saturated heterocyclic groups, and fused saturated heterocyclic groups in which the monocyclic saturated heterocyclic group is fused with a benzene ring or a monocyclic aromatic ring. Ring atoms of the saturated heterocyclic group may be substituted with an oxo group.

[0169] The monocyclic saturated heterocyclic group or the monocyclic non-aromatic heterocyclic group is not particularly limited, and specific examples thereof include an oxetanyl group, a chetanyl group, an azetidinyl group, a pyrrolidinyl group, a pyrrolidinyl-2-one group, a piperidinyl group, a morpholinyl group, a thiomorpholinyl group, a piperazinyl group, a hexamethyleneiminyl group, an oxazolidinyl group, a thiazolidinyl group, an imidazolidinyl group, an oxazolinyl group, a thiazolinyl group, an isoxazolinyl group, an imidazolinyl group, a dioxolyl group, a dioxolanyl group, a dihydrooxadiazolyl group, a 2-oxopyrrolidin-1-yl group, a 2,4-dioxopyrimidin-5-yl group, a 2-oxo-1, Examples thereof include a 3-oxazolidin-5-yl group, a 5-oxo-1,2,4-oxadiazolin-3-yl group, a 1,3-dioxolan-2-yl group, a 1,3-dioxan-2-yl group, a 1,3-dioxepan-2-yl group, a pyranyl group, a tetrahydropyranyl group, a thiopyranyl group, a tetrahydrothiopyranyl group, a 1-oxidetetrahydrothiopyranyl group, a 1,1-dioxidetetrahydrothiopyranyl group, a tetrahydrofuranyl group, a dioxanyl group, a pyrazolidinyl group, a pyrazolinyl group, a tetrahydropyrimidinyl group, a dihydrotriazolyl group, a tetrahydrotriazolyl group, a succinimidyl group, and a pyrrolidonyl group.

[0170] The fused saturated heterocyclic group or the monocyclic non-aromatic saturated heterocyclic group is not particularly limited, and specific examples thereof include a dihydroindolyl group, a dihydroisoindolyl group, a dihydrobenzofuranyl group, a dihydrobenzodioxenyl group, a dihydrobenzodioxepinyl group, a tetrahydrobenzofuranyl group, a chromenyl group, a dihydroquinolinyl group, a tetrahydroquinolinyl group, a dihydroisoquinolinyl group, a tetrahydroisoquinolinyl group, a dihydrophthalazinyl group, and a 1,3-benzoxol group.

[0171] The unsaturated heterocyclic group is not particularly limited, and examples thereof include a 5- or 6-membered monocyclic aromatic heterocyclic group containing, in addition to carbon atoms, 1 to 6 heteroatoms selected from oxygen atoms, sulfur atoms, and nitrogen atoms as ring-constituting atoms; an aromatic fused heterocyclic group in which the monocyclic aromatic heterocyclic group is fused with a benzene ring or a monocyclic aromatic ring; etc. The ring-constituting atoms of the saturated or unsaturated heterocyclic group may be substituted with an oxo group.

[0172] The aromatic monocyclic heterocyclic group is not particularly limited, and specific examples thereof include a furyl group, a thienyl group, a pyridyl group, a 2-oxopyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group (e.g., a 1,3,4-oxadiazolyl group, a 1,2,4-oxadiazolyl group), a thiadiazolyl group (e.g., a 1,3,4-thiadiazolyl group, a 1,2,4-thiadiazolyl group), a triazolyl group (e.g., a 1,2,4-triazolyl group), a tetrazolyl group, and a triazinyl group (e.g., a 1,3,5-triazinyl group, a 1,2,4-triazinyl group). The aromatic fused heterocyclic group is not particularly limited, and specific examples thereof include a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a cinnolinyl group, a phthalazinyl group, a naphthyridinyl group, a benzofuranyl group, a benzothienyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, a benzisothiazolyl group, a benzimidazolyl group, a benzotriazolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a furopycin group, and the like. Lysyl group, thienopyridyl group, pyrrolopyridyl group (e.g., pyrrolo[1,2-a]pyridyl group, pyrrolo[2,3-b]pyridyl group), oxazolopyridyl group (e.g., oxazolo[3,2-a]pyridyl group, oxazolo[5,4-b]pyridyl group, oxazolo[4,5-b]pyridyl group), isoxazolopyridyl group (e.g., isoxazolo[2,3-a]pyridyl group, isoxazolo[4,5-b]pyridyl group, isoxazolo[5,4-b]pyridyl group), thiazolopyridyl groups (e.g., thiazolo[3,2-a]pyridyl groups, thiazolo[5,4-b]pyridyl groups, thiazolo[4,5-b]pyridyl groups), isothiazolopyridyl groups (e.g., isothiazolo[2,3-a]pyridyl groups, isothiazolo[4,5-b]pyridyl groups, isothiazolo[5,4-b]pyridyl groups), imidazopyridyl groups (e.g., imidazo[1,2-a]pyridyl groups, imidazo[4,5-b]pyridyl groups), pyrazolopyridyl groups (e.g., For example, a pyrazolo[1,4-a]pyridyl group, a pyrazolo[3,4-a]pyridyl group, a pyrazolo[4,3-a]pyridyl group, an indolizinyl group, a triazolopyridyl group (for example, a [1,2,4-]triazolo[1,5-a]pyridyl group), a triazolopyrimidinyl group, a pyrrolopyrimidinyl group, a pyrrolopyrazinyl group, an imidazopyrimidinyl group, an imidazopyrazinyl group, a pyrazolopyrimidinyl group, a pyrazolothenyl group, a pyrazolotriazinyl group, and the like.

[0173] The oxy group having a saturated or unsaturated heterocyclic ring refers to a group in which the above-mentioned saturated or unsaturated heterocyclic group is bonded via an oxygen atom. The oxy group having an unsaturated heterocycle is not particularly limited, and specific examples thereof include a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, an isothiazolyloxy group, a thiadiazolyloxy group, a furyloxy group, a pyrrolyloxy group, an imidazolyloxy group, a pyrazolyloxy group, an oxazolyloxy group, an isoxazolyloxy group, a triazolyloxy group, an oxadiazolyloxy group, a thiadiazolyloxy group, and a tetrazolyloxy group.

[0174] The C1-15 alkylcarbonyl group refers to the aforementioned C1-15 alkyl group bonded via a carbonyl. The C1-15 alkylcarbonyl group is not particularly limited, and specific examples include a methylcarbonyl group, an ethylcarbonyl group, a propylcarbonyl group, an isopropylcarbonyl group, a butylcarbonyl group, an isobutylcarbonyl group, a sec-butylcarbonyl group, a t-butylcarbonyl group, a pentylcarbonyl group, and an isopentylcarbonyl group.

[0175] The carbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring means the above-mentioned 3- to 15-membered saturated or unsaturated carbocyclic ring bonded via a carbonyl. The carbonyl group having a 3- to 15-membered saturated or unsaturated carbon ring is not particularly limited, and specific examples include a cyclopropylcarbonyl group, a cyclohexylcarbonyl group, a cyclopropenylcarbonyl group, a cyclohexenylcarbonyl group, and a phenylcarbonyl group (benzoyl group).

[0176] The C1-15 alkoxycarbonyl group refers to the aforementioned C1-15 alkoxy group bonded via a carbonyl. The C1-15 alkoxycarbonyl group is not particularly limited, and specific examples include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a sec-butoxycarbonyl group, a t-butoxycarbonyl group, a pentyloxycarbonyl group, and an isopentyloxycarbonyl group.

[0177] The oxycarbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring means the aforementioned 3- to 15-membered saturated or unsaturated carbocyclic ring bonded via an oxycarbonyl. The oxycarbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring is not particularly limited, and specific examples thereof include oxycarbonyl groups having a saturated carbocyclic ring such as a cyclopropyloxycarbonyl group and a cyclohexyloxycarbonyl group; and oxycarbonyl groups having an unsaturated carbocyclic ring such as a cyclopropenyloxycarbonyl group, a cyclohexenyloxycarbonyl group, and a phenoxycarbonyl group.

[0178] Examples of the optionally substituted aminocarbonyl group include R 70 R 71 Examples include an NCO group. wherein, in the formula, R 70 and R 71 are the same or different and represent a hydrogen atom, a C1-15 alkyl group which may have a substituent, a C2-15 alkenyl group which may have a substituent, or a C2-15 alkynyl group which may have a substituent.

[0179] Examples of the optionally substituted amino group include R 72 R 73 N group and the like. wherein, in the formula, R 72 and R 73 are the same or different and represent a hydrogen atom, a C1-15 alkyl group which may have a substituent, a C2-15 alkenyl group which may have a substituent, or a C2-15 alkynyl group which may have a substituent.

[0180] The C1 to C15 alkylthio group refers to the aforementioned C1 to C15 alkyl group bonded via a thio group (sulfide). The C1-15 alkylthio group is not particularly limited, and examples thereof include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, a t-butylthio group, a pentylthio group, and an isopentylthio group.

[0181] The thio group having a 3- to 15-membered saturated or unsaturated carbocyclic ring refers to a group in which the above-mentioned 3- to 15-membered saturated or unsaturated carbocyclic ring is bonded via a thio group. The thio group having a 3- to 15-membered saturated or unsaturated carbon ring is not particularly limited, and specific examples include a cyclopropylthio group, a cyclohexyloxythio group, a cyclopropenylthio group, and a phenylthio group.

[0182] The C1-C15 alkylsulfinyl group refers to the aforementioned C1-15 alkyl group bonded via a sulfinyl (sulfoxide) group. The C1-15 alkylsulfinyl group is not particularly limited, and examples thereof include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutylsulfinyl group, a sec-butylsulfinyl group, a t-butylsulfinyl group, a pentylsulfinyl group, and an isopentylsulfinyl group.

[0183] The sulfinyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring means a group in which the above-mentioned 3- to 15-membered saturated or unsaturated carbocyclic ring is bonded via a sulfinyl group. The sulfinyl group having a 3- to 15-membered saturated or unsaturated carbon ring is not particularly limited, and specific examples include a cyclopropylsulfinyl group, a cyclohexyloxysulfinyl group, a cyclopropenylsulfinyl group, and a phenylsulfinyl group.

[0184] The C1-C15 alkylsulfonyl group refers to the above C1-15 alkyl group bonded via a sulfonyl group. The C1-15 alkylsulfonyl group is not particularly limited, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, an isobutylsulfonyl group, a sec-butylsulfonyl group, a t-butylsulfonyl group, a pentylsulfonyl group, and an isopentylsulfonyl group.

[0185] The sulfonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring refers to a group in which the above-mentioned 3- to 15-membered saturated or unsaturated carbocyclic ring is bonded via a sulfonyl group. The sulfonyl group having a 3- to 15-membered saturated or unsaturated carbon ring is not particularly limited, and specific examples include a cyclopropylsulfonyl group, a cyclohexyloxysulfonyl group, a cyclopropenylsulfonyl group, and a phenylsulfonyl group.

[0186] Examples of the optionally substituted silyl group include R 80 R 81 R 82 Examples include a Si group. R 80 R 81 R 82 The Si group is not particularly limited, and examples thereof include a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group (TIPS), a t-butyldimethylsilyl group (TBS), a t-butyldiphenylsilyl group (TBDPS), a triphenylsilyl group, a dimethylphenylsilyl group, a diethylphenylsilyl group, a methyldiphenylsilyl group, and an ethyldiphenylsilyl group.

[0187] The substituents in the present disclosure are not particularly limited, and examples include one or more substituents selected from <Group 1>, one or more substituents selected from <Group 2>, one or more substituents selected from <Group 3>, one or more substituents selected from <Group 4>, one or more substituents selected from <Group 5>, one or more substituents selected from <Group 6>, etc.

[0188] Specifically, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkenyl group, or alkoxy group may have one or more substituents selected from the following <Group 1>, and when two or more substituents are present, the substituents may be the same or different.

[0189] <Group 1>: a halogen atom; a hydroxyl group; an optionally substituted C3-6 cycloalkyl group; an optionally substituted C1-6 alkoxy group; an optionally substituted (C1-6 alkyl)carbonyl group; a carboxyl group; an optionally substituted (C1-6 alkoxy)carbonyl group; an optionally substituted phenyl group, an optionally substituted naphthyl group, an optionally substituted phenylcarbonyl group; an optionally substituted C1-6 alkylthio group; an optionally substituted phenylthio group; an optionally substituted C1-6 alkylsulfonyl group; an optionally substituted phenylsulfonyl group; R 80 R 81 R 82 Si group, cyano group; nitro group; formyl group; oxy group having a 3-15 membered saturated or unsaturated carbocyclic ring which may have a substituent; C1-6 alkylsulfinyl group which may have a substituent; phenylsulfinyl group which may have a substituent; R 70 R 71 NCO group; and R 72 R 73 N group. The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkenyl group, or alkoxy group in <Group 1> may be substituted with one or more halogen atoms, and when substituted with two or more halogen atoms, the halogen atoms may be the same or different. An alkyl group substituted with a halogen atom is called a haloalkyl group. An alkenyl group substituted with a halogen atom is called a haloalkenyl group. An alkoxy group substituted with a halogen atom is called a haloalkoxy group. A cycloalkyl group substituted with a halogen atom is called a halocycloalkyl group. A cycloalkenyl group substituted with a halogen atom is called a halocycloalkenyl group. An alkoxy group substituted with a halogen atom is called a haloalkoxy group.

[0190] Furthermore, as the one or more substituents selected from the above <Group 1>, one or more substituents selected from the following <Group 2> are preferred.

[0191] <Group 2>: a halogen atom; a hydroxyl group; a C3-6 cycloalkyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a halogen atom, a C1-6 alkyl group, a (C1-6 alkyl)carbonyl group optionally having at least one substituent selected from the group consisting of a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a carboxyl group; a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group a phenyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a naphthyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a phenylcarbonyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a C1-6 alkylthio group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a phenylthio group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group;A C1-6 alkylsulfonyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; a phenylsulfonyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; and a tri(C1-6 alkyl)silyl group.

[0192] The saturated or unsaturated carbocyclic group (sometimes referred to as a carbocyclic group) and heterocyclic group may have one or more substituents selected from the following <Group 3>, and when they have two or more substituents, the substituents may be the same or different.

[0193] <Group 3>: Halogen atoms; Hydroxyl groups; Cyano groups; Nitro groups; Formyl groups; Oxo groups; Carboxyl groups; C1-6 alkyl groups; C1-6 alkoxy groups; Phenoxy groups; C1-6 alkoxy groups having a C3-6 unsaturated carbocyclic ring; (C1-6 alkoxy)C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 alkynyl groups; C3-6 cycloalkyl groups; C1-6 alkylthio groups; C1-6 alkylthio groups having a C3-6 unsaturated carbocyclic ring; C1-6 alkylsulfinyl groups; C1-6 alkylsulfonyl groups; C1-6 alkylamino groups; Di(C1-6 alkyl )amino group; a (C1-6 alkyl)carbonyl group; a carbonyl group having a C3-6 unsaturated carbocyclic ring; a (C1-6 alkoxy)carbonyl group; an oxycarbonyl group having a C3-6 unsaturated carbocyclic ring; a (C1-6 alkyl)aminocarbonyl group; a di(C1-6 alkyl)aminocarbonyl group; a phenyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group; and a tri(C1-6 alkyl)silyl group.

[0194] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, or alkoxy group in <Group 3> may be substituted with one or more halogen atoms, and when substituted with two or more halogen atoms, the halogen atoms may be the same or different.

[0195] Furthermore, as the one or more substituents selected from the above <Group 3>, one or more substituents selected from the following <Group 4> are preferred.

[0196] <Group 4>: a halogen atom; a nitro group; an oxo group; a carboxyl group; a C1-6 alkyl group; a C1-6 alkoxy group; a phenoxy group; a (C1-6 alkoxy)C1-6 alkyl group; a di(C1-6 alkyl)amino group; a (C1-6 alkyl)carbonyl group; a carbonyl group having a C3-6 unsaturated carbocyclic ring; a (C1-6 alkoxy)carbonyl group; an oxycarbonyl group having a C3-6 unsaturated carbocyclic ring; and a phenyl group optionally having at least one substituent selected from the group consisting of a halogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, and a (C1-6 alkoxy)carbonyl group.

[0197] The amino group may have one or more substituents selected from the following <Group 5>, and when it has two or more substituents, the substituents may be the same or different.

[0198] <Group 5>: C1-6 alkyl groups; (C1-6 alkoxy)C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 alkynyl groups; C3-6 cycloalkyl groups; (C1-6 alkyl)carbonyl groups; (C3-6 cycloalkyl)carbonyl groups; and (C1-6 alkoxy)carbonyl groups.

[0199] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, or alkoxy group in <Group 5> may be substituted with one or more halogen atoms, and when substituted with two or more halogen atoms, the halogen atoms may be the same or different.

[0200] The silyl group may have one or more substituents selected from the following <Group 6>, and when it has two or more substituents, the substituents may be the same or different.

[0201] <Group 6>: a C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 alkynyl group; a C3-6 cycloalkyl group; and a phenyl group which may have one or more C1-6 alkyl groups.

[0202] The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, or alkynyl group in <Group 6> may be substituted with one or more halogen atoms, and when substituted with two or more halogen atoms, the halogen atoms may be the same or different.

[0203] The C1-6 haloalkyl group refers to the above C1-6 alkyl group in which a hydrogen atom has been arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limitation on the number of substitutions, as long as they can exist as substituents. The C1-6 haloalkyl group is not particularly limited, and examples thereof include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a monobromomethyl group, a monoiodomethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2,2-trichloroethyl group, a 3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, a nonafluorobutyl group, a nonafluoro-sec-butyl group, a 3,3,4,4,5,5,5-heptafluoropentyl group, an undecafluoropentyl group, and a tridecafluorohexyl group.

[0204] The haloalkenyl group refers to the C2-C6 alkenyl group in which one or more hydrogen atoms have been substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and there is no particular limitation on the number of substitutions, as long as they can exist as substituents. The C2 to C6 haloalkenyl group is not particularly limited, and specific examples include a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, a 3-fluoroallyl group, a 3,3-difluoroallyl group, a 3,3-dichloroallyl group, a 4,4-difluoro-3-butenyl group, a 5,5-difluoro-4-pentenyl group, and a 6,6-difluoro-5-hexenyl group.

[0205] The C2-6 haloalkynyl group refers to the above C2-6 alkynyl group in which a hydrogen atom has been arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limitation on the number of substitutions, as long as they can exist as substituents. The C2-6 haloalkynyl group is not particularly limited, and examples thereof include a 2-fluoroethynyl group, a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3,3-difluoro-1-propynyl group, a 3-chloro-3,3-difluoro-1-propynyl group, a 3-bromo-3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, a 4,4-difluoro-1-butynyl group, a 4,4-difluoro-2-butynyl group, a 4-chloro-4,4-difluoro-1-butynyl group, a 4-chloro-4,4-difluoro-2-butynyl group, and a 4-bromo-4,4-difluoro 5,5-difluoro-3-pentynyl group, 5-chloro-5,5-difluoro-3-pentynyl group, 5-bromo-5,5-difluoro-3-pentynyl group, 5,5,5-trifluoro-3-pentynyl group, 6,6-difluoro-4-hexynyl group, 6-chloro-6,6-difluoro-4-hexynyl group, 6-bromo-6,6-difluoro-4-hexynyl group, and 6,6,6-trifluoro-4-hexynyl group.

[0206] The C1-6 haloalkoxy group refers to the above C1-C6 alkoxy group in which a hydrogen atom has been arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and there is no particular limitation on the number of substitutions, as long as they can exist as substituents. The C1-6 haloalkoxy group is not particularly limited, and specific examples include a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a pentafluoroethoxy group, a 2,2,2-trichloroethoxy group, a 3,3-difluoropropyloxy group, a 3,3,3-trifluoropropyloxy group, a heptafluoropropyloxy group, a heptafluoroisopropyloxy group, a 2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy group, a nonafluorobutoxy group, a nonafluoro-sec-butoxy group, a 3,3,4,4,5,5,5-heptafluoropentyloxy group, an undecafluoropentyloxy group, and a tridecafluorohexyloxy group.

[0207] The halocycloalkyl group refers to the above-mentioned C3-15 cycloalkyl group in which a hydrogen atom has been arbitrarily substituted with one or more halogen atoms. The halocycloalkenyl group refers to the above C3-15 cycloalkenyl group in which a hydrogen atom is optionally substituted with one or more halogen atoms.

[0208] Method for producing onium salt compounds There are no particular limitations on the method for producing the onium salt compound represented by general formula (1). The onium salt compound represented by general formula (1) can be produced, for example, from a compound represented by the following general formula (2) according to the production route shown in Scheme 1 below.

[0209] (Scheme 1) [ka]

[0210] In the formula, R A , R 4 , R 5 , R 6 , X -and dotted lines are the same as above. L is a leaving group. The leaving group is not particularly limited, and examples thereof include halogen atoms such as a fluoro group, a chloro group, a bromo group, and an iodo group; a mesylate group, a tosyl group, a nosyl group, a cyano group, an alkyl sulfate group, and a triflate group. Y is a counter anion, such as a fluoro group, a chloro group, a bromo group, an iodo group, a mesylate group, a tosyl group, a nosyl group, a cyano group, an alkyl sulfate group, or a triflate group. M is a cation. Examples of the cation include a hydrogen ion; alkali metal ions such as sodium ion, lithium ion, potassium ion, rubidium ion, cesium ion, and beryllium ion; alkaline earth metal ions such as magnesium ion, calcium ion, strontium ion, and barium ion; metal ions such as scandium ion, titanium ion, zirconium ion, vanadium ion, niobium ion, chromium ion, molybdenum ion, manganese ion, iron ion, ruthenium ion, cobalt ion, rhodium ion, nickel ion, palladium ion, copper ion, silver ion, zinc ion, cadmium ion, aluminum ion, gallium ion, tin ion, and antimony ion; and ammonium ions such as tetramethylammonium and tetrabutylammonium.

[0211] (Process I) Step I is a step shown in the following scheme I.

[0212] [ka]

[0213] In the formula, R A , R 5 , R 6 , L and dotted lines are the same as above.

[0214] Specifically, step I is a step of reacting a compound represented by general formula (2) with a compound represented by general formula (3) to produce a compound represented by general formula (4). Step I can be carried out, for example, in the presence of an acid or a base, in a solvent.

[0215] The compound represented by formula (2) used in this reaction can be commercially available or can be produced by known methods. For example, 4-mercaptobenzothiazole, 4-methyl-2-mercaptobenzothiazole, 2-mercaptothiazoline, etc. can be purchased from Tokyo Chemical Industry Co., Ltd.

[0216] In step I, the amount of the compound represented by general formula (3) is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by general formula (2) and the desired reaction proceeds, but is preferably 1 equivalent or more and 3 equivalents or less. Examples of the compound represented by general formula (3) include fluorobenzyl, benzyl chloride, benzyl bromide, benzyl iodide, 4-methylbenzyl fluoride, 4-methylbenzyl chloride, 4-methylbenzyl bromide, 4-methylbenzyl iodide, 1-(fluoromethyl)naphthalene, 1-(chloromethyl)naphthalene, 1-(bromomethyl)naphthalene, 1-(methyl iodide)naphthalene, 4-phenylbenzyl fluoride, 4-phenylbenzyl chloride, and 4-phenyl bromide. Examples of the alkyl halides include alkyl halides having an aromatic group such as benzyl and 4-phenylbenzyl iodide; alkyl halides such as fluoromethyl, methyl chloride, methyl bromide and methyl iodide; and alkyl halides having an alicyclic hydrocarbon group such as cyclopentyl fluoride, cyclopentyl chloride, cyclopentyl bromide, cyclopentyl iodide, 1-adamantyl fluoride, 1-adamantyl chloride, 1-adamantyl bromide and 1-adamantyl iodide.

[0217] Instead of the compound represented by general formula (3), a compound having a double bond can be used to carry out an addition reaction with the compound represented by general formula (2) (thiol compound). Examples of such a compound (3) having a double bond capable of addition reaction include oxirane compounds such as methyloxirane and phenyloxirane; and unsaturated hydrocarbons such as styrene, indene, N-phenylmaleimide, methyl acrylate, and methyl methacrylate.

[0218] In Step I, the acid or base used can be used in a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.01 equivalents or more and 3 equivalents or less relative to the compound represented by general formula (3). The type of acid is not particularly limited, and examples thereof include hydrogen fluoride, hydrogen chloride, hydrogen bromide, hydrogen iodide, methanesulfonic acid, tosylic acid, hypochlorous acid, hypobromous acid, hypoiodous acid, sulfuric acid, nitric acid, phosphoric acid, boric acid, trifluoroacetic acid, trifluoromethanesulfonic acid, pyridinium paratoluenesulfonate, acetic acid, formic acid, oxalic acid, boron trifluoride, boron tribromide, titanium tetrachloride, titanium tetrabromide, aluminum chloride, aluminum bromide, zinc chloride, zinc bromide, copper chloride, copper bromide, copper iodide, titanium chloride, tin chloride, etc. These acids can be used alone or in combination of two or more in any desired ratio. The type of base is not particularly limited, and examples thereof include inorganic salts such as lithium carbonate, sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate, cesium carbonate, calcium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium hydride, and potassium hydride; and organic bases such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, imidazole, guanidine, pyridine, 1,4-diazabicyclo[2.2.2]octane, and 4-dimethylaminopyridine. These bases can be used alone or in combination of two or more in any ratio.

[0219] Examples of the solvent used in Step I include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, 4-methyltetrahydropyran, and dioxane; alcohol solvents such as methanol, ethanol, n-propanol, and i-propanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride; sulfur-based solvents such as dimethyl sulfoxide and sulfolane; organic solvents such as ketone-based solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; These solvents can be used alone or in combination of two or more in any proportion. Preferred examples of the solvent include ethyl acetate, tetrahydrofuran, nitromethane, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone, methyl ethyl ketone, water, and dimethyl sulfoxide.

[0220] The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 10 to 20,000 parts by mass per 100 parts by mass of the compound represented by general formula (2).

[0221] In step I, the reaction temperature is not particularly limited, and is usually, for example, about 20° C. to 100° C. The reaction time is not particularly limited, and is, for example, about 1 to 72 hours.

[0222] As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc.; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; or saline solution. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any proportion. The number of separations is not particularly limited and can be performed depending on the desired purity or yield.

[0223] The reaction mixture containing the compound represented by general formula (4) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

[0224] The reaction mixture containing the compound represented by general formula (4) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound is not decomposed. The reaction mixture containing the compound represented by general formula (4) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, distillation, column chromatography, or the like.

[0225] (Process II) Step II is shown in the following scheme II.

[0226] [ka]

[0227] In the formula, R A , R 4 , R 5 , R 6 , Y and dotted lines are the same as above.

[0228] Step II is a step of producing a compound represented by general formula (6) by reacting the compound represented by general formula (4) obtained in Step I with a compound represented by general formula (5). Step II can be carried out, for example, in the presence of a solvent.

[0229] In step II, the amount of the compound represented by general formula (5) is not particularly limited as long as the desired reaction proceeds, but is usually about 0.5 to 10 equivalents relative to the compound represented by general formula (4). Examples of the compound represented by general formula (5) include alkyl halides such as methyl iodide, ethyl chloride, ethyl bromide, ethyl iodide, propyl chloride, propyl bromide, propyl iodide, butyl chloride, butyl bromide, and butyl iodide; dialkyl sulfates such as dimethyl sulfate and diethyl sulfate; dialkyl carbonates such as dimethyl carbonate and diethyl carbonate; aryl halides such as fluorobenzyl, benzyl chloride, benzyl bromide, and benzyl iodide; methylated products such as methyl tosylate, methyl trifluoroacetate, methyl trifluorosulfonate, methyl hypochlorite, methyl formate, and methyl orthoformate; and dialkyl carbonates such as dimethyl carbonate and diethyl carbonate.

[0230] Examples of the solvent used in Step II include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, 4-methyltetrahydropyran, and dioxane; alcohol solvents such as methanol, ethanol, n-propanol, and i-propanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride; sulfur-based solvents such as dimethyl sulfoxide and sulfolane; organic solvents such as ketone-based solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; These solvents can be used alone or in combination of two or more in any proportion. The solvent is preferably ethyl acetate, isopropyl acetate, butyl acetate, tetrahydrofuran, nitromethane, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone, methyl ethyl ketone, dimethyl sulfoxide, methanol, or water.

[0231] The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 10 to 20,000 parts by mass per 100 parts by mass of the compound represented by general formula (4).

[0232] In Step II, the reaction temperature is not particularly limited and may be, for example, about 0° C. to 70° C. The reaction time is not particularly limited and may be, for example, 0.5 to 72 hours.

[0233] In Step II, a catalyst for accelerating the reaction can be added as needed. The type of catalyst is not particularly limited, and examples thereof include alkali metal halides such as lithium bromide, lithium iodide, sodium bromide, sodium iodide, potassium bromide, and potassium iodide; and cesium halides such as cesium bromide and cesium iodide. These catalysts can be used alone or in combination of two or more in any ratio.

[0234] As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc.; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; or saline solution. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any proportion. The number of separations is not particularly limited and can be performed depending on the desired purity or yield.

[0235] The reaction mixture containing the compound represented by general formula (6) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

[0236] The reaction mixture containing the compound represented by general formula (6) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound is not decomposed. The reaction mixture containing the compound represented by general formula (6) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, or the like.

[0237] (Process III) Step III is shown in the following scheme III. [ka]

[0238] In the formula, R A , R 4 , R 5 , R 6 , X - , Y, M and dotted lines are the same as above.

[0239] Step III is a step of producing a compound represented by general formula (1) by reacting the compound represented by general formula (6) obtained in Step II with a compound represented by general formula (7). Step III can be carried out, for example, in the presence of a solvent.

[0240] In step III, the amount of the compound represented by general formula (7) is not particularly limited as long as the desired reaction proceeds, but is usually about 0.5 to 3 equivalents relative to the compound represented by general formula (6).

[0241] In step III, the compound represented by general formula (7) is, for example, a boron compound containing a fluorine-containing aromatic ring such as MB(C6F5)4, MB(C6H4F)4, or MB(C6H3(CF3)2)4; a gallium compound containing a fluorine-containing aromatic ring such as MGa(C6F5)4; a carbon compound containing a fluorine-containing sulfonyl group such as MC(SO2CF3)3; a cyclic sulfonimide compound having a fluorine atom such as MN(SO2CF2)2CF2; or a phosphorus compound containing a fluorine-containing alkyl group such as MPF3(C2F5)3. Here, M is preferably, for example, an alkali metal such as lithium, sodium, potassium, or rubidium; an alkaline earth metal such as magnesium or calcium; or an ammonium salt such as tetramethylammonium or tetrabutylammonium.

[0242] Examples of the solvent used in Step III include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, 4-methyltetrahydropyran, and dioxane; alcohol solvents such as methanol, ethanol, n-propanol, and i-propanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride; sulfur-based solvents such as dimethyl sulfoxide and sulfolane; organic solvents such as ketone-based solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; These solvents can be used alone or in combination of two or more in any proportion. From the viewpoint of the subsequent purification step, the solvent is preferably a water-insoluble solvent such as toluene, dichloromethane, ethyl acetate, nitromethane, or 4-methyltetrahydropyran.

[0243] The amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 10 to 20,000 parts by mass per 100 parts by mass of the compound represented by general formula (6).

[0244] In Step III, the reaction temperature is not particularly limited and may be, for example, 0° C. to 50° C. The reaction time is not particularly limited and may be, for example, 0.5 to 24 hours. As a post-treatment for the reaction, a separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc.; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.; or saline solution. During the separation operation, if necessary, a water-immiscible solvent can be added, such as a benzene-based solvent such as toluene, xylene, benzene, chlorobenzene, or dichlorobenzene; an ester-based solvent such as ethyl acetate, isopropyl acetate, or butyl acetate; an ether-based solvent such as diethyl ether, diisopropyl ether, or methyl t-butyl ether; a halogen-based solvent such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride; or a hydrocarbon-based solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. These solvents can be used alone or in combination in any proportion. The number of separations is not particularly limited and can be performed depending on the desired purity or yield.

[0245] The reaction mixture containing the compound represented by general formula (1) obtained above can be dehydrated with a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.

[0246] The reaction mixture containing the compound represented by general formula (1) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound is not decomposed. The reaction mixture containing the compound represented by general formula (1) obtained after distilling off the solvent can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, or the like.

[0247] <Application> The onium salt compound of the present disclosure can be used for various purposes, such as an acid generator, a polymerization initiator, an adhesive, a sealing material, a resist, a coating material, a sealing material, a pressure-sensitive adhesive, a surface modifier, a surface treatment agent, a dye fixing agent, an ink fixing agent, a pigment dispersant, a flocculating agent, an agricultural chemical, an antibacterial agent, a disinfectant, a paper strength agent, a corrosion inhibitor, a plating brightener, an optical material, a solubilizer, a color-changeable material, an agricultural chemical, and a colorant.

[0248] Acid generator The onium salt compound of the present disclosure can be used as an acid generator. The onium salt compound of the present disclosure has excellent solvent compatibility and excellent storage stability. Here, solvent compatibility means that it can be dissolved in a variety of solvents. Examples of solvents capable of dissolving the onium salt compound of the present disclosure include ether-based solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, 4-methyltetrahydropyran, and dioxane; alcohol-based solvents such as methanol, ethanol, n-propanol, and i-propanol; benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; nitrile-based solvents such as acetonitrile; N-methylpyrrolidone, N,N- Amide solvents such as dimethylformamide and N,N-dimethylacetamide; urea solvents such as 1,3-dimethyl-2-imidazolidinone; halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride; sulfur-based solvents such as dimethyl sulfoxide and sulfolane; organic solvents such as ketone-based solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitro-based solvents such as nitromethane; carbonate-based solvents such as propylene carbonate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, and ethylene carbonate; PGMAc Ester solvents such as (propylene glycol 1-monomethyl ether 2-acetate), ethyl acetate, isopropyl acetate, and butyl acetate; "HP4032," "HP4032D," and "HP4032SS" (naphthalene-type epoxy resins) manufactured by DIC Corporation; "828US," "jER (registered trademark, sometimes abbreviated hereinafter) 828EL," "825," and "jER828" (bisphenol A-type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "jER807" and "1750" (bisphenol F-type epoxy resins) manufactured by Mitsubishi Chemical Corporation. epoxy resin); "jER152" (phenol novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630" and "630LSD" (glycidylamine type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "ZX-1059" (mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagase ChemteX Corporation; "Celloxide" (registered trademark, may be omitted hereinafter) manufactured by Daicel Corporation.)2021P" (alicyclic epoxy resin with an ester skeleton); "PB-3600" (epoxy resin with a butadiene structure) manufactured by Daicel Corporation; and liquid epoxy resins such as "ZX-1658" and "ZX-1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd. These solvents may be used alone or in combination of two or more in any desired ratio. Among these, the solvents preferably used are propylene carbonate, methyl isobutyl ketone, PGMAc (propylene glycol 1-monomethyl ether 2-acetate), toluene, Celloxide 2021P, and jER828. Storage stability means that when a reactive composition containing the onium salt compound of the present disclosure is stored, the onium salt is not decomposed and the reactive composition is not gelled, and is stable. Furthermore, the onium salt compounds of the present disclosure also have excellent photoreactivity and thermal reactivity.

[0249] <Polymerization initiator> The onium salt compound of the present disclosure can be used as a polymerization initiator. The onium salt compound of the present disclosure can be used as a photopolymerization initiator or a thermal polymerization initiator. Furthermore, the onium salt compound of the present disclosure can be used as a radical polymerization initiator. Specifically, examples of the photopolymerization initiator include a photoradical polymerization initiator, a photocationic polymerization initiator, a photoanionic polymerization initiator, etc. Among the above photopolymerization initiators, a photoradical polymerization initiator or a photocationic polymerization initiator can be preferably used. Furthermore, the polymerization initiator in the present disclosure may contain a known polymerization initiator in addition to the onium salt compound. Examples of known polymerization initiators include cationic photopolymerization initiators such as diazonium salts, iodonium salts such as diaryliodonium salts, sulfonium salts such as triarylsulfonium salts, triarylpyrilium salts, benzylpyridinium thiocyanate, dialkylphenacylsulfonium salts, and dialkylhydroxyphenylphosphonium salts.

[0250] <Reactive Composition> The reactive composition of the present disclosure includes the onium salt compound of the present disclosure and a reactive compound. Here, the reactive composition can be referred to as a reactive resin composition, a curable resin composition, a photosensitive resin composition, or the like. The reactive composition of the present disclosure can be used for various purposes, such as an acid generator, a polymerization initiator, an adhesive, a sealant, a resist, a solubilizer, a color-changeable material, an agricultural chemical, and a colorant. Furthermore, a cured product of a reactive composition obtained by mixing the onium salt compound of the present disclosure with a reactive compound can form a film that has excellent insulating properties and transparency.

[0251] The type of reactive compound is not particularly limited, and examples thereof include compounds having an acid labile group and compounds having a radical reactive group. The compound having an acid labile group is not particularly limited as long as it is a compound that reacts or hydrolyzes with acid, and examples thereof include resins having acid labile groups such as those described in JP 2023-169223 A, which have a leaving group and the leaving group is eliminated upon contact with acid, converting the structural unit into a structural unit having a hydrophilic group (e.g., a hydroxy group or a carboxy group); ester group-containing polymers having structural units derived from (meth)acrylic monomers such as those described in JP 2020-075903 A; epoxy compounds; oxetane compounds; vinyl compounds; silyl compounds; polyamic acids; and compounds that develop color by reacting with acid (color-forming compounds), such as leuco dyes, triarylmethane dyes, diphenylmethane dyes, fluoran dyes, spiropyran dyes, and rhodamine dyes, as described in JP 2022-086976 A.

[0252] The compound having a radical reactive group is not particularly limited, and refers to a compound that reacts with a radical. Examples of the compound that reacts with a radical include compounds that react with a radical to give a cured product, such as those described in Japanese Patent No. 6464271. Examples of the compound that reacts with a radical include KAYARAD Examples of suitable esters include DPHA, DPHA-2C, PET-30, TMPTA, TPA-320, TPA-330, RP-1040, T-1420, D-310, DPCA-20, DPCA-30, DPCA-60, and GPO-303 (manufactured by Nippon Kayaku Co., Ltd.), NK Ester A-TMPT, A-TMMT, A-TMM3, A-TMM3L, and A-9550 (manufactured by Shin-Nakamura Chemical Co., Ltd.), V#3PA, V#400, V#36095D, V#1000, V#1080, and Viscoat #802 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), and dendrimer-type multifunctional acrylates such as Sirius-501 and SUBARU-501 (manufactured by Osaka Organic Chemical Industry Co., Ltd.).In addition, Shiko UV-1400B, UV-1700B, UV-6300B, UV-7550B, UV-7600B, UV-7605B, UV-7610B, UV-7620EA, UV-7630B, UV-7640B, UV-6630B, UV-7000B, UV-7510B, UV-7461TE, UV-3000B, UV-3200B, UV-32 10EA, UV-3310EA, UV-3310B, UV-3500BA, UV-3520TL, UV-3700B, UV-6100B, UV-6640B, UV-2000B, UV-2010B, UV-2250EA, UV-2750B (manufactured by Nippon Synthetic Chemical Industry Co., Ltd.), UL-503LN (manufactured by Kyoeisha Chemical Co., Ltd.), Unidic 17-806, and Unidic 17-813 , V-4030, V-4000BA (manufactured by Dainippon Ink and Chemicals, Inc.), EB-1290K, EB-220, EB-5129, EB-1830, EB-4858 (manufactured by Daicel UCB Corporation), Hi-Corp AU-2010, Hi-Corp AU-2020 (manufactured by Tokushiki Co., Ltd.), Aronix M-1960 (manufactured by Toagosei Co., Ltd.), Art Resin UN-3320HA, UN-3320HC, Other usable compounds include tri- or higher functional urethane acrylate compounds such as UN-3320HS, UN-904 (manufactured by Negami Chemical Industrial Co., Ltd.), NK Oligo U-4HA, U-15HA (manufactured by Shin-Nakamura Chemical Co., Ltd.), and tri- or higher functional polyester compounds such as Aronix M-8100, M-8030, M-9050 (manufactured by Toagosei Co., Ltd.), and KRM-8307 (manufactured by Daicel Cytec Co., Ltd.).

[0253] The reactive compound is preferably liquid at 25° C., as this provides excellent workability and low-temperature curing properties. The viscosity of the reactive compound at 25° C. is preferably 0.1 to 30,000 mPa·s, more preferably 1 to 15,000 mPa·s, and particularly preferably 10 to 1,000 mPa·s. The reactive composition is preferably liquid at 25° C., as this provides excellent workability and low-temperature curing properties. There are no particular limitations on the viscosity of the reactive compound at 25° C.

[0254] Of the reactive compounds, for example, epoxy compounds (which may also be referred to as epoxy monomers) are not particularly limited, and examples thereof include aromatic epoxy resins, hydrogenated epoxy resins, and alicyclic epoxy compounds.

[0255] The hydrogenated epoxy resin is not particularly limited, and examples thereof include hydrogenated bisphenol A epoxy resins, hydrogenated bisphenol F epoxy resins, hydrogenated bisphenol E epoxy resins, diglycidyl ethers of alkylene oxide adducts of hydrogenated bisphenol A, diglycidyl ethers of alkylene oxide adducts of hydrogenated bisphenol F, hydrogenated phenol novolac epoxy resins, and hydrogenated cresol novolac epoxy resins.

[0256] Commercially available hydrogenated bisphenol A epoxy resins include YX-8000, YX-8034 (manufactured by Mitsubishi Chemical Corporation), EXA-7015 (manufactured by DIC Corporation), ST-3000 (manufactured by Nippon Steel Chemical & Material Co., Ltd.), Rikaresin HBE-100 (manufactured by New Japan Chemical Co., Ltd.), and EX-252 (manufactured by Nagase ChemteX Corporation). Commercially available hydrogenated bisphenol F epoxy resins include YL-6753 (manufactured by Mitsubishi Chemical Corporation).

[0257] The alicyclic epoxy compound is not particularly limited, and examples thereof include 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, ε-caprolactone-modified 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, bis(3,4-epoxycyclohexyl)adipate, 1,2-epoxy-4-vinylcyclohexane, 1,4-cyclohexanedimethanol diglycidyl ether, epoxyethyldivinylcyclohexane, diepoxyvinylcyclohexane, 1,2,4-triepoxyethylcyclohexane, limonene dioxide, and alicyclic epoxy group-containing silicone oligomers.

[0258] Commercially available alicyclic epoxy compounds are not particularly limited, and examples thereof include Celloxide 2081, Celloxide 2021P, Celloxide 2000, Celloxide 3000, EHPE3150 (manufactured by Daicel Corporation), TTA21 (manufactured by Jiangsu TetraChem Co., Ltd.), Rikaresin DME-100 (manufactured by New Japan Chemical Co., Ltd.), X-40-2670, X-22-169AS, and X-22-169B (manufactured by Shin-Etsu Chemical Co., Ltd.), but are not limited thereto.

[0259] The aromatic epoxy resin is not particularly limited, and examples thereof include aromatic bisphenol A type epoxy resins, aromatic bisphenol F type epoxy resins, aromatic bisphenol E type epoxy resins, diglycidyl ethers of alkylene oxide adducts of aromatic bisphenol A, diglycidyl ethers of alkylene oxide adducts of aromatic bisphenol F, diglycidyl ethers of alkylene oxide adducts of aromatic bisphenol E, aromatic novolac type epoxy resins, urethane-modified aromatic epoxy resins, nitrogen-containing aromatic epoxy resins, rubber-modified aromatic epoxy resins containing polybutadiene or nitrile butadiene rubber (NBR), etc.

[0260] Commercially available aromatic epoxy resins include, for example, jER825, 827, 828, 828EL, 828US, 828XA, 834, 806, 806H, 807, 604, and 630 (manufactured by Mitsubishi Chemical Corporation), EPICLON830, EXA-830LVP, EXA-850CRP, 835LV, HP4032D, 703, 720, 726, HP820, N-660, N-680, N-695, N-655-EXP-S, N-665-EXP-S, N-685-EXP-S, and N- 740, N-775, N-865 (manufactured by DIC Corporation), EP4100, EP4000, EP4080, EP4085, EP4088, EP4100HF, EP4901HF, EP4000S, EP4000L, EP4003S, EP4010S, EP4010L (manufactured by ADEKA Corporation), Denacol EX614B, EX411, EX314, EX201, EX212, EX252 (manufactured by Nagase ChemteX Corporation), and the like.

[0261] Examples of oxetane compounds include 3-ethyl-3-hydroxymethyloxetane, 3-(meth)allyloxymethyl-3-ethyloxetane, (3-ethyl-3-oxetanylmethoxy)methylbenzene, 4-fluoro-[1-(3-ethyl-3-oxetanylmethoxy)methyl]benzene, [1-(3-ethyl-3-oxetanylmethoxy)ethyl]phenyl ether, isobutoxymethyl (3-ethyl-3-oxetanylmethyl) ether, 2-ethylhexyl (3-ethyl-3-oxetanylmethyl) ether, ethyl diethylene glycol (3-ethyl-3-oxetanylmethyl) ether, tetrahydrofurfuryl (3-ethyl-3-oxetanylmethyl) ether, tetrabromophenyl (3-ethyl-3-oxetanylmethyl) ether, and 2-tetrabromophenoxyethyl (3-ethyl-3-oxetanylmethyl) ether. , pentachlorophenyl (3-ethyl-3-oxetanylmethyl) ether, pentabromophenyl (3-ethyl-3-oxetanylmethyl) ether, ethylene glycose bis(3-ethyl-3-oxetanylmethyl) ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl) ether, tetraethylene glycol bis(3-ethyl-3-oxetanylmethyl) ether, trimethylolpropane tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, ditrimethylolpropane tetrakis(3-ethyl-3-oxetanylmethyl) ether, and the like.

[0262] Examples of commercially available oxetane compounds include, but are not limited to, OXT-212, OXT-221, OXT-213, and OXT-101 (manufactured by Toagosei Co., Ltd.).

[0263] The vinyl compound is not particularly limited, and examples thereof include aryl vinyl ethers such as phenyl vinyl ether; alkyl vinyl ethers such as n-butyl vinyl ether and n-octyl vinyl ether; cycloalkyl vinyl ethers such as cyclohexyl vinyl ether; vinyl ethers having a hydroxyl group such as 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether and 2-hydroxybutyl vinyl ether; polyfunctional vinyl ethers such as hydroquinone divinyl ether, 1,4-butanediol divinyl ether, cyclohexane divinyl ether, cyclohexane dimethanol divinyl ether, ethylene glycol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexyl vinyl ether, 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether, 2-(2-vinyloxyethoxy)ethyl acrylate and 2-(2-vinyloxyethoxy)ethyl methacrylate; styrene, 4-methoxystyrene, 4-methylstyrene, and the like. Commercially available vinyl compounds include, for example, NPVE, IPVE, NBVE, IBVE, EHVECHVE (manufactured by Nippon Carbide Industries Co., Ltd.), HEVE, DEGV, HBVE (manufactured by Maruzen Petrochemical Co., Ltd.), VEEA, VEEM (manufactured by Nippon Shokubai Co., Ltd.), but are not limited to these.

[0264] The silyl compound is not particularly limited, and examples thereof include dialkoxysilane, trialkoxysilane, tetraalkoxysilane, and 3-glycidoxypropyltrimethoxysilane. Specifically, a commercially available silyl compound is KBM403 manufactured by Shin-Etsu Chemical Co., Ltd.

[0265] The polyamic acid (polyimide precursor) is not particularly limited, and examples thereof include a primary reaction product of di-succinic anhydride and diamine. Specific examples thereof include compounds described in JP-A-2021-138840.

[0266] In the reactive composition of the present disclosure, the onium salt compound or polymerization initiator is used in an amount of, for example, about 0.001 to 50 parts by mass, and preferably 0.01 to 10 parts by mass, relative to 100 parts by mass of the reactive compound. In this specification, any numerical range indicated with "to" includes both the upper and lower limits, unless otherwise specified. The reactive compounds can be used alone or in combination of two or more. Furthermore, the reactive composition of the present disclosure may contain other optional components in addition to the onium salt compound and reactive compound. The optional components are not particularly limited and include, for example, solvents for dilution, surfactants, etc. Other optional components include sensitizers, antioxidants, stabilizers, solvents, leveling agents, silane coupling agents, fillers, conductive particles, plasticizers, antifoaming agents, foaming agents, ultraviolet absorbers, ion adsorbents, pigments, dyes, fluorescent materials, release agents, antistatic agents, flame retardants, radical curing compounds, etc.

[0267] Examples of the solvent include ether solvents such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, 4-methyltetrahydropyran, and dioxane; alcohol solvents such as methanol, ethanol, n-propanol, and i-propanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; nitrile solvents such as acetonitrile; N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetone. Amide-based solvents such as methyl amide; urea-based solvents such as 1,3-dimethyl-2-imidazolidinone; halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride; sulfur-based solvents such as dimethyl sulfoxide and sulfolane; organic solvents such as ketone-based solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitro-based solvents such as nitromethane; carbonate-based solvents such as propylene carbonate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, and ethylene carbonate; PGMAc (propylene glycol 1-monomethyl ether 2- Ester solvents such as ethyl acetate, ethyl acetate, isopropyl acetate, and butyl acetate; DIC Corporation's "HP4032," "HP4032D," and "HP4032SS" (naphthalene-type epoxy resins); Mitsubishi Chemical Corporation's "828US," "jER828EL," "825," and "jER828" (bisphenol A-type epoxy resins); Mitsubishi Chemical Corporation's "jER807" and "1750" (bisphenol F-type epoxy resins); and Mitsubishi Chemical Corporation's "jER152" (phenol novolac-type epoxy resin). ; "630" and "630LSD" (glycidylamine type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "ZX-1059" (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagase ChemteX Corporation; "Celloxide 2021P" (alicyclic epoxy resin with an ester structure) manufactured by Daicel Corporation; "PB-3600" (epoxy resin with a butadiene structure) manufactured by Daicel Corporation;Examples include liquid epoxy resins such as "ZX-1658" and "ZX-1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; These solvents may be used alone or in combination of two or more in any desired ratio. Among these, the solvents preferably used are propylene carbonate, methyl isobutyl ketone, PGMAc (propylene glycol 1-monomethyl ether 2-acetate), toluene, Celloxide 2021P, and jER828.

[0268] <Surfactant> The reactive composition included in the present disclosure may further contain a surfactant. By including a surfactant, wettability during application can be improved, and a uniform resin film and cured film can be obtained. The surfactant is not particularly limited, and examples thereof include fluorine-based surfactants, silicone-based surfactants, alkyl-based surfactants, and acrylic-based surfactants.

[0269] The surfactant preferably contains a surfactant containing at least one of a fluorine atom and a silicon atom. This contributes to obtaining a uniform resin film (improving coating properties), improving developability, and also improving adhesive strength. As such a surfactant, for example, a nonionic surfactant containing at least one of a fluorine atom and a silicon atom is preferred. Commercially available surfactants include, for example, F-251, F-253, F-281, F-430, F-477, F-551, F-552, F-553, F-554, F-555, F-556, F-557, F-558, F-559, F-560, F-561, F-562, F-563, F-565, F-568, F-569, F-570, F-572, and F-574 from the "Megafac" series manufactured by DIC Corporation. fluorine-containing oligomer surfactants such as F-575, F-576, R-40, R-40-LM, R-41, and R-94; fluorine-containing nonionic surfactants such as Ftergent 250 and Ftergent 251 manufactured by Neos Corporation; and silicone surfactants such as the SILFOAM (registered trademark) series manufactured by Wacker Chemie (e.g., SD100TS, SD670, SD850, SD860, and SD882).

[0270] The content of the surfactant is not particularly limited, and can be, for example, 0.001 to 10% by mass, preferably 0.01 to 1% by mass, based on the total amount of nonvolatile components of the reactive composition.

[0271] <Method of producing reactive composition> The reactive composition can be produced by uniformly mixing the onium salt compound or a polymerization initiator containing an onium salt compound with the reactive compound, and, if necessary, together with other optional components added, using a commonly known mixing device such as a planetary mixer, a homogenizer, a planetary mixer, a three-roll mill, a bead mill, etc. The components may be mixed simultaneously or sequentially.

[0272] <Polymer and its manufacturing method> The reactive composition of the present disclosure can be polymerized by known methods to obtain a polymer. The method for polymerizing the reactive composition is not particularly limited, and examples thereof include a method of polymerizing using light such as ultraviolet light, radiation, or electron beams, and a method of polymerizing using heat. For example, a method of polymerization using light irradiation can include a photopolymerization step of prepolymerizing (precuring) the reactive composition by light irradiation, and a thermal polymerization step of main polymerization by heating. When the acid generator of the present disclosure is used, physical properties such as adhesion, uniformity, hardness, toughness, and durability are improved by polymerizing the composition by light irradiation and then performing a heat treatment.

[0273] In the photoreaction step, the light to be irradiated preferably includes light in the wavelength range of 10 nm to 500 nm, and more preferably includes ultraviolet light with a wavelength of 400 nm or less.

[0274] The light source is not particularly limited, and examples thereof include ultraviolet LEDs, blue LEDs, white LEDs, lasers, metal halide lamps, xenon lamps, and high- or medium-pressure mercury lamps.

[0275] The amount of light irradiation is not particularly limited, and for example, the intensity at a wavelength of 313 nm is 0.1 to 1000 mW / cm 2 Examples include:

[0276] The light irradiation time is not particularly limited and is, for example, 0.1 seconds to 3 minutes.

[0277] In the thermal polymerization step, the heating temperature is, for example, 60 to 130° C., preferably 70 to 120° C., and more preferably 80 to 100° C. The heating time is not particularly limited, and may be, for example, 10 minutes to 4 hours.

[0278] The uses of the onium salt compound, acid generator, polymerization initiator, reactive composition, or polymer of the present disclosure are not particularly limited, and can be applied to various fields and products in which resin materials are used, and can be widely used in electrical and electronic materials, construction, civil engineering, automotive, medical materials, and the like.

[0279] For example, examples of applications in electrical and electronic materials include adhesives, encapsulants (semiconductor encapsulants), sealants, insulating materials, thermally conductive materials, hot melt materials, paints, and potting agents. More specifically, examples of the material include sealing materials for electronic components such as printed wiring boards, copper foils, copper-clad laminates, interlayer insulating materials, wiring coating films, resin-coated copper foils (RCC), and prepregs; layer-forming materials; color filters, films for flexible displays, resist materials, solder resist inks, and materials for forming display devices such as alignment films; resist materials and materials for forming semiconductor devices such as buffer coat films; and materials for forming optical components such as holograms, optical waveguides, optical circuits, optical circuit components, and antireflection films. Examples of optical components that can be used include camera modules, LiDAR modules (light detection and ranging, detection and ranging using light (including laser or infrared)), lens materials for still cameras, finder prisms, target prisms, finder covers, light-receiving sensor parts, photographic lenses, and adhesives for projection television projection lenses.

[0280] Examples of materials for construction use include joint sealants for exterior materials such as various metal panels and siding boards, coating materials, primers, etc., sealants used between exterior materials, base materials, ceiling materials and interior materials, adhesives, injection materials, vibration damping materials, soundproofing materials, conductive materials for electromagnetic wave shielding, putty materials, etc., adhesives for bonding tiles and stone to exterior wall materials and base materials, adhesives and pressure-sensitive adhesives for bonding wood flooring materials, polymer material floor sheets and floor tiles to various floors, and injection materials for repairing cracks in various exterior and interior materials.

[0281] Examples of materials for civil engineering applications include joint sealants for roads, bridges, tunnels, breakwaters, and various concrete products, coating materials, primers, paints, injection materials, putty materials, formwork materials, and spraying materials.

[0282] Examples of materials for automotive applications include sealing materials, coating materials, cushioning materials, vibration-damping materials, soundproofing materials, spray materials, etc. for car bodies; adhesives, pressure-sensitive adhesives, coating materials, foam materials, etc. for car interiors; sealing materials, adhesives, etc. for car parts; and sealing materials, adhesives, coating materials for various steel plate joints in trucks, buses, etc.

[0283] Examples of medical material applications include medical rubber materials, medical adhesives, and medical equipment sealing materials. [Example]

[0284] Examples of the present invention and comparative examples will be specifically described below, but the present invention is not limited to these examples.

[0285] <Method of producing onium salt compound>

[0286] Example 1 [ka]

[0287] The compound (1-1) of Example 1 was produced through the following steps 1, 2 and 3. [ka]

[0288] A 100 ml four-neck flask was charged with 4.0 g (33.5 mmol) of 2-mercaptothiazoline (2-1), 30 ml of ethyl acetate, 4.24 g (33.5 mmol) of benzyl chloride (3-1), and 1.87 g (33.5 mmol) of potassium hydroxide, and the mixture was stirred at 60°C for 24 hours. 30 ml of water was added to the resulting reaction solution, and the organic layer was separated by a separation operation. The resulting residue was concentrated to obtain intermediate compound (4-1).

[0289] [ka]

[0290] The obtained intermediate compound (4-1), 4.23 g (33.4 mmol) of dimethyl sulfate (5-1), and 10 ml of acetonitrile were placed in a 100 ml four-neck flask and stirred for 48 hours at 50° C. To the obtained reaction solution, 100 ml of water and 20 ml of ethyl acetate were added, and the aqueous layer containing intermediate compound (6-1) was separated by a separation operation.

[0291] [ka]

[0292] A 500 ml four-neck flask was charged with the solution containing the obtained intermediate compound (6-1), 211 g of a 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1), and 100 ml of ethyl acetate, and the mixture was stirred at 25°C for 2 hours. The organic layer of the obtained reaction solution was separated by a separation operation. The residue was concentrated to obtain the product compound (1-1) in a yield of 90%. As an internal standard, 1 HNMR shows tetramethylsilane (TMS), 19 For F-NMR, an appropriate amount of hexafluorobenzene was added.

[0293] 1 HNMR(400MHz,CD3CN)δ7.51~7.36(m,5H),4.59(s,2H),4.35(t,1H),3.66(t,1H),3.29(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.12(s,2F),-162.30(t,1F),-166.72(t,2F)

[0294] Example 2 [ka]

[0295] Example 2 was synthesized in the same manner as in Example 1, except that 5.6 g (33.5 mmol) of 2-mercaptobenzothiazole (2-2) was used instead of 2-mercaptothiazoline (2-1) in Step 1 of Example 1. The yield of the resulting compound (1-2) was 86%.

[0296] 1 HNMR(400MHz,CD3CN)δ8.12(d,1H),7.94(d,1H),7.82(t,1H),7.70(t,1H),7.59(d,2H),7.50~7.37(m,3H),4.80(s,2H),4.04(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.15(s,2F),-162.32(t,1F),-166.74(t,2F)

[0297] Example 3 [ka]

[0298] Example 3 was synthesized in the same manner as in Example 2, except that 4.71 g of 4-methylbenzyl chloride (3-2) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-3) was 91%.

[0299] 1 HNMR(400MHz,CD3CN)δ8.13(d,1H),7.95(d,1H),7.82(t,1H),7.70(t,1H),7.46(d,2H),7.26(d,2H),4.76(s,2H),4.04(s,3H),2.34(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.09(s,2F),-162.32(t,1F),-166.72(t,2F)

[0300] Example 4 [ka]

[0301] Example 4 was synthesized in the same manner as in Example 2, except that 5.92 g of 1-(chloromethyl)naphthalene (3-3) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-4) was 82%.

[0302] 1 HNMR(400MHz,CD3CN)δ8.18(t,2H),8.00(d,2H),7.94(d,1H),7.84(t,2H),7.72(t,1H),7.70~7.58(m,2H),7.54(t,1H),5.26(s,2H),4.01(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.10(s,2F),-162.32(t,1F),-166.73(t,2F)

[0303] Example 5 [ka]

[0304] Example 5 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step 1 of Example 2 was replaced with 4.71 g of 2-phenylethyl chloride (3-4). The yield of the resulting compound (1-5) was 90%.

[0305] 1 HNMR(400MHz,CD3CN)δ8.10(d,1H),7.92(d,1H),7.80(t,1H),7.68(t,1H),7.57(d,2H),7.48~7.35(m,3H),3.80(t,2H),3.40(t,2H),4.02(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.13(s,2F),-162.33(t,1F),-166.73(t,2F)

[0306] Example 6 [ka]

[0307] Example 6 was synthesized in the same manner as in Example 2, except that 5.18 g of 2,4-dimethylbenzyl chloride (3-5) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-6) was 82%.

[0308] 1 HNMR(400MHz,CD3CN)δ8.16(d,1H),7.95(d,1H),7.83(t,1H),7.72(t,1H),7.40(d ,1H),7.14(s,1H),7.08(d,1H),4.76(s,2H),4.03(s,3H),2.43(s,3H),2.31(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.09(s,2F),-162.32(t,1F),-166.73(t,2F)

[0309] Example 7 [ka]

[0310] Example 7 was synthesized in the same manner as in Example 2, except that 5.18 g of 3,4-dimethylbenzyl chloride (3-6) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-7) was 82%.

[0311] 1 HNMR(400MHz,CD3CN)δ8.12(d,1H),7.93(d,1H),7.82(t,1H),7.70(t,1H),7.34(s ,1H),7.29(d,1H),7.20(d,1H),4.73(s,2H),4.03(s,3H),2.27(s,3H),2.26(s,3H) 19FNMR(376MHz,CD3CN)δ-132.15(s,2F),-162.33(t,1F),-166.75(t,2F)

[0312] Example 8 [ka]

[0313] Example 8 was synthesized in the same manner as in Example 2, except that 5.1 g of 4-vinylbenzyl chloride (3-7) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-8) was 82%.

[0314] 1 HNMR(400MHz,CD3CN)δ8.14(d,1H),7.96(d,1H),7.82(t,1H),7.70(t,1H),7.45(d, 2H),7.22(d,2H),6.64(dd,1H),5.71(d,1H),5.25(d,1H),4.72(s,2H),4.04(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.09(s,2F),-162.33(t,1F),-166.72(t,2F)

[0315] Example 9 [ka]

[0316] Example 9 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 2 was replaced with 29.69 g of tetrakis(3,5-ditrifluoromethylphenyl)borate sodium salt (7-2). The yield of the resulting compound (1-9) was 82%.

[0317] 1HNMR(400MHz,CD3CN)δ8.14(d,1H),7.95(d,1H),7.82(t,1H),7.73(s,8H),7.7 0(t,1H),7.68(s,4H),7.61(d,2H),7.51~7.36(m,3H),4.82(s,2H),4.06(s,3H) 19 FNMR (376MHz, CD3CN) δ-61.91(s)

[0318] Example 10 [ka]

[0319] Example 10 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in step 3 of Example 2 was replaced with 13.87 g of tetrakis(4-fluoromethylphenyl)borate sodium salt (7-3). The yield of the resulting compound (1-10) was 85%.

[0320] 1 HNMR(400MHz,CD3CN)δ8.05(d,1H),7.87(d,1H),7.78(t,1H),7.66(t,1H),7.55(d,2) H),7.48~7.43(t,3H),7.22~7.11(m,8H),6.79~6.69(t,8H),4.72(s,2H,3.96(s,3H) 19 FNMR(376MHz,CD3CN)δ-122.98(s)

[0321] Example 11 [ka]

[0322] Example 11 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in step 3 of Example 2 was replaced with 10.02 g of lithium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide (7-4). The yield of the resulting compound (1-11) was 85%.

[0323] 1 HNMR(400MHz,CD3CN)δ8.11(d,1H),7.93(d,1H),7.81(t,1H),7.69(t,1H),7.59(d,2H),7.50~7.39(m,3H),4.79(s,2H),4.03(s,3H) 19 FNMR(376MHz,CD3CN)δ-119.01(s,2F),-125.47(s,1F)

[0324] Example 12 [ka]

[0325] Example 12 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in step 3 of Example 2 was replaced with 15.0 g of potassium tris(trifluoromethanesulfonyl)methanide (7-5). The yield of the resulting compound (1-12) was 81%.

[0326] 1 HNMR(400MHz,CD3CN)δ8.12(d,1H),7.94(d,1H),7.81(t,1H),7.70(t,1H),7.59(d,2H),7.50~7.39(m,3H),4.79(s,2H),4.03(s,3H) 19 FNMR (376MHz, CD3CN) δ-75.96(s)

[0327] Example 13 [ka]

[0328] Example 13 was synthesized in the same manner as in Example 3, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 3 was replaced with 10.02 g of lithium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide (7-4). The yield of the resulting compound (1-13) was 81%.

[0329] 1 HNMR(400MHz,CD3CN)δ8.12(d,1H),7.94(d,1H),7.82(t,1H),7.70(t,1H),7.47(d,2H),7.27(d,2H),4.76(s,2H),4.03(s,3H),2.35(s,3H) 19 FNMR(376MHz,CD3CN)δ-119.02(s,2F),-125.48(s,1F)

[0330] Example 14 [ka]

[0331] Example 14 was synthesized in the same manner as in Example 3, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 3 was replaced with 29.69 g of tetrakis(3,5-ditrifluoromethylphenyl)borate sodium salt (7-2). The yield of the resulting compound (1-14) was 82%.

[0332] 1 HNMR(400MHz,CD3CN)δ8.13(d,1H),7.95(d,1H),7.82(t,1H),7.74(s,8H),7.70(t ,1H),7.68(s,4H),7.48(d,2H),7.27(d,2H),4.78(s,2H),4.05(s,3H),2.35(s,3H) 19 FNMR (376MHz, CD3CN) δ-61.68(s)

[0333] Example 15 [ka]

[0334] Example 15 was synthesized in the same manner as in Example 2, except that 4.23 g (33.4 mmol) of dimethyl sulfate (5-1) in Step 2 of Example 2 was replaced with 5.17 g of diethyl sulfate (5-2). The yield of the resulting compound (1-15) was 78%.

[0335] 1 HNMR(400MHz,CD3CN)δ8.14(d,1H),7.98(d,1H),7.82(t,1H),7.70(t,1H),7.60(d,2H),7.50~7.39(m,3H),4.81(s, 2H),4.60(q,2H),1.50(t,3H) 19 FNMR(376MHz,CD3CN)δ-132.11(s,2F),-162.33(t,1F),-166.74(t,2F)

[0336] Example 16 [ka]

[0337] Example 16 was synthesized in the same manner as in Example 2, except that 5.71 g of 1-adamantyl chloride (3-8) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-16) was 71%.

[0338] 1HNMR(400MHz,CD3CN)δ8.16(d,1H),8.03(d,1H),7.87(t,1H),7.77(t,1H),4.14(s,3H),2.32(s,6H),2.21(s,3H),1.80(s,6H) 19 FNMR(376MHz,CD3CN)δ-132.17(s,2F),-162.33(t,1F),-166.74(t,2F)

[0339] Example 17 [ka]

[0340] Example 17 was synthesized in the same manner as in Example 2, except that 3.5 g of cyclopentyl chloride (3-9) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-17) was 70%.

[0341] 1 HNMR(400MHz,CD3CN)δ8.15(d,1H),7.94(d,1H),7.82(t,1H),7.71(t,1H),4.25~4.11(m,1H),4.01(s,3H),2.48~2.43(m,2H),1.93~1.75(m,6H) 19 FNMR(376MHz,CD3CN)δ-132.11(s,2F),-162.32(t,1F),-166.73(t,2F)

[0342] Example 18 [ka]

[0343] Example 18 was synthesized in the same manner as in Example 17, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 17 was replaced with 10.02 g of lithium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide (7-4). The yield of the resulting compound (1-18) was 72%.

[0344] 1 HNMR(400MHz,CD3CN)δ8.15(d,1H),7.94(d,1H),7.82(t,1H),7.71(t,1H),4.23~4.13(m,1H),4.00(s,3H),2.51~2.38(m,2H),1.94~1.75(m,6H) 19 FNMR(376MHz,CD3CN)δ-119.01(s,2F),-125.46(s,1F)

[0345] Example 19 [ka]

[0346] Example 19 was synthesized in the same manner as in Example 17, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 17 was replaced with 29.69 g of tetrakis(3,5-ditrifluoromethylphenyl)borate sodium salt (7-2). The yield of the resulting compound (1-19) was 73%.

[0347] 1 HNMR(400MHz,CD3CN)δ8.15(d,1H),7.95(d,1H),7.83(t,1H),7.73~7.68(m ,13H),4.24~4.14(m,1H),4.02(s,3H),2.51~2.37(m,2H),1.92~1.74(m,6H) 19 FNMR (376MHz, CD3CN) δ-61.67(s)

[0348] Example 20 [ka]

[0349] Example 20 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in step 3 of Example 2 was replaced with 2.55 g of allyl chloride (3-10). The yield of the resulting compound (1-20) was 79%.

[0350] 1 HNMR(400MHz,CD3CN)δ8.15(d,1H),7.96(d,1H),7.83(t,1H),7.71(t,1H),6.08~5.98(m,1H),5.66(d,1H),5.49(d,1H),4.23(d,2H),4.06(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.16(s,2F),-162.32(t,1F),-166.72(t,2F)

[0351] Example 21 [ka]

[0352] Example 21 was synthesized in the same manner as in Example 2, except that 5.1 g of cinnamyl chloride (3-11) was used instead of benzyl chloride (3-1) in step 3 of Example 2. The yield of the resulting compound (1-21) was 75%.

[0353] 1 HNMR(400MHz,CD3CN)δ8.14(d,1H),7.95(d,1H),7.82(t,1H),7.70(t,1H),7.47(d ,2H),7.38~7.34(m,3H),7.00(d,1H),6.42~6.34(m,1H),4.40(d,2H),4.05(s,3H) 19FNMR(376MHz,CD3CN)δ-132.13(s,2F),-162.32(t,1F),-166.73(t,2F)

[0354] Example 22 [ka]

[0355] Example 22 was synthesized in the same manner as in Example 21, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 21 was replaced with 10.02 g of lithium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide (7-4). The yield of the resulting compound (1-22) was 77%.

[0356] 1 HNMR(400MHz,CD3CN)δ8.13(d,1H),7.94(d,1H),7.81(t,1H),7.70(t,1H),7.48(d ,2H),7.41~7.28(m,3H),6.99(d,1H),6.42~6.34(m,1H),4.39(d,2H),4.04(s,3H) 19 FNMR(376MHz,CD3CN)δ-119.01(s,2F),-125.47(s,1F)

[0357] Example 23 [ka]

[0358] Example 23 was synthesized in the same manner as in Example 21, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 21 was replaced with 29.69 g of tetrakis(3,5-ditrifluoromethylphenyl)borate sodium salt (7-2). The yield of the resulting compound (1-23) was 76%.

[0359] 1 HNMR(400MHz,CD3CN)δ8.15(d,1H),7.95(d,1H),7.82(t,1H),7.78~7.61(m,13H),7.5 0(d,2H),7.41~7.27(m,3H),7.02(d,1H),6.48~6.34(m,1H),4.42(d,2H),4.07(s,3H) 19 FNMR (376MHz, CD3CN) δ-61.68(s)

[0360] Example 24 [ka]

[0361] Example 24 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step 1 of Example 2 was replaced with 3.02 g of 3-chloro-1-butene (3-12). The yield of the resulting compound (1-24) was 70%.

[0362] 1 HNMR(400MHz,CD3CN)δ8.14(d,1H),7.96(d,1H),7.83(t,1H),7.72(t,1H),6.04~5 .97(m,1H),5.62(d,1H),5.43(d,1H),4.61~4.49(m,1H),4.05(s,3H),1.72(d,3H) 19 FNMR(376MHz,CD3CN)δ-132.04(s,2F),-162.32(t,1F),-166.71(t,2F)

[0363] Example 25 [ka]

[0364] Example 25 was synthesized in the same manner as in Example 24, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 24 was replaced with 10.02 g of lithium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide (7-4). The yield of the resulting compound (1-25) was 71%.

[0365] 1 HNMR(400MHz,CD3CN)δ8.14(d,1H),7.95(d,1H),7.82(t,2H),7.71(t,2H),6.05~5 .99(m,1H),5.63(d,1H),5.44(d,1H),4.57~4.53(m,1H),4.04(s,3H),1.72(d,3H) 19 FNMR(376MHz,CD3CN)δ-119.01(s,2F),-125.47(s,1F)

[0366] Example 26 [ka]

[0367] Example 26 was synthesized in the same manner as in Example 24, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 24 was replaced with 29.69 g of tetrakis(3,5-ditrifluoromethylphenyl)borate sodium salt (7-2). The yield of the resulting compound (1-26) was 75%.

[0368] 1 HNMR(400MHz,CD3CN)δ8.15(d,1H),7.96(d,1H),7.83(t,1H),7.76~7.66(m,13H),6.0 5~5.98(m,1H),5.63(d,1H),5.44(d,1H),4.58~4.54(m,1H),4.05(s,3H),1.72(d,3H) 19 FNMR (376MHz, CD3CN) δ-61.67(s)

[0369] Example 27 [ka]

[0370] Example 27 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step 1 of Example 2 was replaced with 4.1 g of (trimethylsilyl)methyl chloride (3-13). The yield of the resulting compound (1-27) was 76%.

[0371] 1 HNMR(400MHz,CD3CN)δ8.14(d,1H),7.92(d,1H),7.82(t,1H),7.69(t,1H),5.20(s,2H),4.03(s,3H),0.29(s,9H) 19 FNMR(376MHz,CD3CN)δ-132.05(s,2F),-162.33(t,1F),-166.72(t,2F)

[0372] Example 28 [ka]

[0373] Example 28 was synthesized in the same manner as in Example 2, except that 5.3 g of chloromethyl phenyl sulfide (3-14) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-28) was 59%.

[0374] 1 HNMR(400MHz,CD3CN)δ8.16(d,1H),7.95(d,1H),7.83(t,1H),7.71(t,1H), 7.69~7.55(m,2H),7.43~7.35(m,2H),7.28(d,1H),4.04(s,2H),3.04(s,3H) 19FNMR(376MHz,CD3CN)δ-132.18(s,2F),-162.37(t,1F),-166.80(t,2F)

[0375] Example 29 [ka]

[0376] Example 29 was synthesized in the same manner as in Example 2, except that 5.78 g of N-phenylmaleimide (3-15) was used instead of benzyl chloride (3-1) in Step 1 of Example 2. The yield of the resulting compound (1-29) was 75%.

[0377] 1 HNMR(400MHz,CD3CN)δ8.21(d,1H),8.02(d,1H),7.89(t,1H),7.78(t,1H),7.59~7.49(m,5H),5.10(d,1H),4.04(s,3H),3.64(d,1H),3.13(m,1H) 19 FNMR(376MHz,CD3CN)δ-132.10(s,2F),-162.33(t,1F),-166.75(t,2F)

[0378] Example 30 [ka]

[0379] Example 30 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step 1 of Example 2 was replaced with 3.56 g of 1-chloropentane (3-16). The yield of the resulting compound (1-30) was 90%.

[0380] 1HNMR(400MHz,CD3CN)δ8.15(d,1H),7.95(d,1H),7.83(t,1H),7.70(t,1H),4.04(s,3 H),3.54(t,2H),2.02~1.91(m,2H),1.61~1.47(m,2H),1.45~1.38(m,2H),0.94(t,3H) 19 FNMR(376MHz,CD3CN)δ-132.07(s,2F),-162.32(t,1F),-166.71(t,2F)

[0381] Example 31 [ka]

[0382] Example 31 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step 1 of Example 2 was replaced with 3.88 g of indene (3-17), 1.87 g of potassium hydroxide was replaced with 7.62 g of trifluoroacetic acid, and toluene was replaced with dichloromethane. The yield of the resulting compound (1-31) was 70%.

[0383] 1 HNMR(400MHz,CD3CN)δ8.30(d,1H),8.12(d,1H),7.94(t,1H),7.83(t,1H),7.53~7.41(m,2H ),7.38(d,1H),7.28(t,1H),6.88(d,1H),5.81(t,1H),4.04(s,3H),3.70(d,1H),3.04(s,2H) 19 FNMR(376MHz,CD3CN)δ-132.13(s,2F),-162.34(t,1F),-166.76(t,2F)

[0384] Example 32 [ka]

[0385] Example 32 was synthesized in the same manner as in Example 2, except that 5.6 g of 2-mercaptobenzothiazole (2-2) was replaced with 6.05 g of 4-methyl-2-mercaptobenzothiazole (2-3) in Step 1 of Example 2. The yield of the resulting compound (1-32) was 87%.

[0386] 1 HNMR(400MHz,CD3CN)δ7.95~7.92(m,1H),7.62~7.51(m,4H),7.49~7.39(m,3H),4.78(s,2H),4.28(s,3H),2.87(s,3H) 19 FNMR(376MHz,CD3CN)δ-132.13(s,2F),-162.32(t,1F),-166.73(t,2F)

[0387] Example 33 [ka]

[0388] Example 33 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in step 1 of Example 2 was replaced with 3.89 g of 3-chlorocyclohexene (3-18). The yield of the resulting compound (1-33) was 67%.

[0389] 1 HNMR(400MHz,CD3CN)δ8.15(d,1H),7.97(d,1H),7.85(t,1H),7.72(t,1H),5.99~5.93(m ,1H),5.52(m,1H),4.59~4.47(m,1H),4.04(s,3H),3.01(m,2H),1.62(m,2H),1.42(m,2H) 19 FNMR(376MHz,CD3CN)δ-132.03(s,2F),-162.33(t,1F),-166.71(t,2F)

[0390] Comparative Example 1: Compound described in Patent Document 6 (JP-A-07-025863) [ka]

[0391] Comparative Example 1 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in step 3 of Example 2 was replaced with 8.66 g of sodium hexafluoroantimonate. The yield of the comparative product compound (a1) was 82%.

[0392] 1 HNMR(400MHz,CD3CN)δ8.12(d,1H),7.94(d,1H),7.82(t,1H),7.70(t,1H),7.59(d,2H),7.50~7.40(m,3H),4.79(s,2H),4.03(s,3H) 19 FNMR(376MHz,CD3CN)δ-109.35~-135.11(m)

[0393] Comparative Example 2: Compound described in Patent Document 6 (JP-A-07-025863) [ka]

[0394] Comparative Example 2 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in step 3 of Example 2 was replaced with 3.67 g of sodium tetrafluoroborate. The yield of the comparative product compound (a2) was 89%.

[0395] 1 HNMR(400MHz,CD3CN)δ8.13(d,1H),7.95(d,1H),7.82(t,1H),7.70(t,1H),7.60(dd,2H),7.50~7.40(m,3H),4.80(s,2H),4.04(s,3H) 19 FNMR(376MHz,CD3CN)δ-150.12(s)

[0396] Comparative Example 3: Compound described in Patent Document 6 (JP-A-07-025863) [ka]

[0397] Comparative Example 3 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in step 3 of Example 2 was replaced with 5.61 g of sodium hexafluorophosphate. The yield of the comparative product compound (a3) was 90%.

[0398] 1 HNMR(400MHz,CD3CN)δ8.12(d,1H),7.94(d,1H),7.82(t,1H),7.70(t,1H),7.59(d,2H),7.50~7.40(m,3H),4.79(s,2H),4.03(s,3H) 19 FNMR (376MHz, CD3CN) δ-72.20(s)

[0399] Comparative Example 4 [ka]

[0400] Comparative Example 4 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in step 3 of Example 2 was replaced with 5.75 g of sodium triflate. The yield of the comparative product compound (a4) was 88%.

[0401] 1 HNMR(400MHz,CD3CN)δ8.14(d,1H),7.97(d,2H),7.82(t,1H),7.70(t,1H),7.60(dd,2H),7.50~7.39(m,3H),4.80(s,2H),4.04(s,3H) 19 FNMR (376MHz, CD3CN) δ-77.67(s)

[0402] Comparative Example 5 [ka]

[0403] Comparative Example 5 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in step 3 of Example 2 was replaced with 11.43 g of sodium tetraphenylborate. The yield of the comparative product compound (a5) was 90%.

[0404] 1 HNMR(400MHz,CD3CN)δ7.97(d,1H),7.82~7.70(m,2H),7.63(t,1H),7.53(d,2H),7.4 7~7.37(m,3H),7.30~7.26(m,8H),6.96(t,8H),6.81(t,4H),4.65(s,2H),3.84(s,3H)

[0405] Comparative Example 6 [ka]

[0406] Comparative Example 6 was synthesized in the same manner as in Example 2, except that the 10% aqueous solution of tetrakis(pentafluorophenyl)borate sodium salt (7-1) in Step 3 of Example 2 was replaced with 9.59 g of lithium bis(trifluoromethanesulfonyl)imide. The yield of the comparative product compound (a6) was 84%.

[0407] 1 HNMR(400MHz,CD3CN)δ8.12(d,1H),7.94(d,1H),7.82(t,1H),7.70(t,1H),7.59(d,2H),7.50~7.39(m,3H),4.79(s,2H),4.04(s,3H) 19 FNMR (376MHz, CD3CN) δ-78.59(s)

[0408] Evaluation test of onium salt compounds <Solvent compatibility> At 25°C, 1 g of each of the onium salt compounds of Examples 1 to 33 or Comparative Examples 1 to 6 was placed in a 30 mL screw tube. Next, 1 g of solvent was added to each container and mixed in a planetary centrifugal mixer "ARE-310" manufactured by Thinky Corporation, and the mass Ws (g) of the solvent required to completely dissolve the onium salt compound was measured.

[0409] The solubility (S), which is the mass of solute that can be dissolved in 100 g of solvent, was calculated according to the following formula. Formula: S[%]=1 / (Ws / 100) In Table 1, the solubility when dissolved in 1 g of solvent is indicated as ">100", and the solubility when not completely dissolved even when 200 g of solvent is added is indicated as "0.5>".

[0410] The evaluation of solvent compatibility was carried out by counting the types of solvents in which the solubility was 1% or more among the solvents measured this time, and assigning points as follows: 5: The number of solvents with a solubility of 1% or more is 6 or more. 4: There are five solvents with a solubility of 1% or more. 3: There are four types of solvents with a solubility of 1% or more. 2: There are three types of solvents with a solubility of 1% or more. 1: There are two types of solvents with a solubility of 1% or more. 0: One solvent with a solubility of 1% or more

[0411] The following six solvents were selected: Propylene carbonate Methyl isobutyl ketone PGMAc (Propylene glycol 1-monomethyl ether 2-acetate) ·toluene Celloxide (registered trademark) 2021P jER(registered trademark) 828

[0412] The type of solvent was determined based on the Hansen solubility parameter. Compounds with similar SP values are more compatible with each other, and generally, the larger the SP value, the higher the polarity. Solvents were selected so that a wide range of solubility could be investigated, from solvents with low to high SP values. For reference, the SP value of PC is 13.3 (MPa 1 / 2 ), and the SP value of MIBK is 8.3 (MPa 1 / 2 ), and the SP value of toluene is 8.9 (MPa 1 / 2 )

[0413] The Celloxide 2021P is 3,4-epoxycyclohexylmethyl(3,4-epoxy)cyclohexanecarboxylate.

[0414] The jER828 is a so-called bisphenol A type epoxy resin produced by a condensation reaction between bisphenol A and epichlorohydrin.

[0415] <Storage stability> The prepared onium salt compounds of Examples 1 to 33 or the onium salt compounds of Comparative Examples 1 to 6 were placed in 30 mL light-shielding screw tubes and allowed to stand in a thermostatic bath at 25° C. Every few days, the screw tubes were turned sideways for one minute, and the number of days until gelation occurred, at which point the liquid no longer flowed, was measured.

[0416] (5-point scale) 5: The solution has not flowed for more than 40 days. 4: The solution stopped flowing after 30 to 39 days 3: The solution stopped flowing after 20 to 29 days. 2: The solution stopped flowing after 10 to 19 days. 1: The solution has stopped flowing within 9 days

[0417] Evaluation test for reactive compositions containing onium salt compounds The reactive compositions in the present disclosure were prepared based on the following manufacturing method, and the photoreactivity and thermal reactivity of these reactive compositions were evaluated as follows.

[0418] <Reactive Composition Production Example 1> To each 10 mL light-shielding screw tube was added 20.0 mg of the onium salt compound of Examples 1 to 33 or the onium salt compound of Comparative Examples 1 to 6, and 0.2 mg of 4-hydroxyphenyldimethylsulfonium triflate (manufactured by Sanshin Chemical Industry Co., Ltd., trade name: DSP-Tf) as a polymerization inhibitor. Next, 20.0 mg of propylene carbonate as a solvent was added to each container and completely dissolved to prepare Solution 1. Furthermore, 20.1 mg of each of the prepared solutions 1 was placed in a 30 mL light-shielding screw tube. Furthermore, 10 g of Celloxide 2021P (trade name, manufactured by Daicel Corporation) was added to the container as a reactive compound, and immediately mixed in a planetary centrifugal mixer "ARE-310" to prepare a reactive composition.

[0419] <Photoreactivity (1)> The prepared reactive composition was subjected to UV-DSC measurement to measure the total calorific value under continuous light irradiation. Note that a larger total calorific value indicates higher photoreactivity. (conditions) Measurement equipment: Differential scanning calorimeter (DSC600, Hitachi High-Tech Corporation) Atmosphere: Nitrogen gas, 50mL / min. Lamp: LA-410UV, mercury xenon lamp Sample amount: 1 mg ·Illuminance: 20mW / cm 2 (313nm) ·Measurement temperature: 25℃ Total heat generation (J / g): The total heat generation (W / g) during light irradiation

[0420] (evaluation) The photoreactivity was evaluated on a two-level scale as follows: A: Total calorific value is 1 J / g or more B: Total calorific value is less than 1 J / g The results are shown in Table 1.

[0421] <Thermal reactivity (1)> The thermal properties of the prepared reactive composition were measured using a differential scanning calorimetry (DSC). Note that the lower the reaction temperature below, the higher the thermal reactivity. (conditions) Measurement equipment: Differential scanning calorimeter (X-DSC7000, Hitachi High-Tech Corporation) Atmosphere: Nitrogen gas, 40mL / min. Sample size: 5mg ·Temperature conditions: 30~310℃, 10℃ / min. Reaction temperature (℃): The temperature at the top of the lowest exothermic peak

[0422] (evaluation) The thermal reactivity was evaluated in two stages as follows: A: Reaction temperature is less than 200°C B: Reaction temperature is 200°C or higher The results are shown in Table 1.

[0423] <Reactive Composition Production Example 2> To each 10 mL light-shielding screw tube, 20.0 mg of each of the onium salt compounds of Examples 1 to 33 or Comparative Examples 1 to 6 was added. Next, 20.0 mg of propylene carbonate was added as a solvent to each container. The compounds were completely dissolved to prepare each Solution 2. Furthermore, 20.0 mg of each of the prepared solutions 2 was placed in each 30 mL light-shielding screw tube. Furthermore, 10 g of trimethylolpropane acrylate (TMPTA, manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the container as a reactive compound, and immediately mixed in a planetary centrifugal mixer "ARE-310" to prepare a reactive composition.

[0424] <Photoreactivity (2)> The prepared reactive composition was subjected to UV-DSC measurement to measure the total calorific value under continuous light irradiation. Note that a larger total calorific value indicates higher photoreactivity. (conditions) Measurement equipment: Differential scanning calorimeter (DSC600, Hitachi High-Tech Corporation) Atmosphere: Nitrogen gas, 50mL / min. Lamp: LA-410UV, mercury xenon lamp Sample amount: 1 mg ·Illuminance: 20mW / cm 2 (313nm) ·Measurement temperature: 25℃ Total heat generation (J / g): The total heat generation (W / g) during light irradiation

[0425] (evaluation) The photoreactivity was evaluated on a two-level scale as follows: A: Total calorific value is 150 J / g or more B: Total calorific value is less than 150 J / g The results are shown in Table 1.

[0426] [Table 1]

[0427] <Result> The onium salt compounds of Examples 1 to 33 were excellent in solvent compatibility and storage stability. On the other hand, the onium salt compounds of Comparative Examples 1 to 6 were inferior in at least one of solvent compatibility and storage stability. Furthermore, it was found that the reactive compositions containing the onium salt compounds of Examples 1 to 33 were excellent in photoreactivity and thermal reactivity. Therefore, it was found that the reactive compositions containing the onium salt compounds of the present disclosure have photoreactivity and thermal reactivity and can be used as dual-type acid generators.

[0428] Examples 34 to 72 Furthermore, the compounds listed in Table 2 below were produced according to the production methods described in Examples 1 to 33 above. Representative examples of compounds represented by general formula (1B-3) of the present disclosure are shown in Tables 2 and 3, and representative examples of compounds represented by general formula (1A-3) are shown in Table 4, but the present disclosure is not limited to these. In the tables, "Me" represents a methyl group, "Bn" represents a benzyl group, and "Ph" represents a phenyl group.

[0429] [Table 2]

[0430] [Table 3]

[0431] [Table 4]

[0432] As described above, the onium salt compound of the present disclosure has excellent solvent compatibility and excellent storage stability. Furthermore, it has been found that a reactive composition containing the onium salt compound of the present disclosure has photoreactivity and thermal reactivity, and therefore can be used as a dual-type acid generator. Furthermore, it has been found that the onium salt compound of the present disclosure is photoreactive and therefore functions not only as an acid generator but also as a radical generator. Therefore, the onium salt compounds of the present disclosure can be used in a variety of applications, such as adhesives, sealants, and resists.

Claims

1. General formula (1): 【Chemical 1】 (In the formula, R Ａ represents an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group. R ４ represents an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. R ５ and R ６ are the same or different and represent a hydrogen atom or an optionally substituted C1-15 alkyl group; Alternatively, the R ５ and R ６ These two groups may be bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring. The saturated or unsaturated carbocyclic ring may further have a substituent. The dotted lines indicate single or double bonds. X － teeth, The following general formula (XA2): 【Chemistry 2】 (wherein R 30 , R 31 , R 32 , R 33 and R 34 are the same or different and represent a hydrogen atom, a fluorine atom or a C n F 2n+1 group, provided that any one of R 30 , R 31 , R 32 , R 33 and R 34 is a fluorine atom or a C n F 2n+1 group, and n represents an integer of 1 to 15); The following general formula (XC2): 【Chemistry 3】 (wherein R 40 , R 41 and R 42 are the same or different and represent a C t F 2t+1 group, and t represents an integer of 1 to 15); The following general formula (XD1): 【Chemistry 4】 (wherein r represents an integer of 1 to 6), or The following general formula (XE1): P(RX 8 )c(RX 9 )d (wherein RX 8 represents a CuF 2u+1 group, RX 9 represents a fluorine atom, u represents an integer of 1 to 15, c represents an integer of 1 to 6, d represents 0 to 5, and c+d represents 6), and is a phosphorus anion containing a fluorine-containing alkyl group.) An onium salt compound represented by the formula:

2. General formula (1): 【Chemistry 5】 (In the formula, R A represents an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, or an optionally substituted heterocyclic group. R 4 represents a C1-15 alkyl group which may have a substituent, or a 3- to 15-membered saturated or unsaturated carbocyclic group which may have a substituent. R 5 and R 6 are the same or different and each represent a hydrogen atom; Alternatively, R 5 and R 6 may be bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring, which may further have a substituent. The dotted lines indicate single or double bonds. X - is The following general formula (XA2): 【Chemistry 6】 (wherein R 30 , R 31 , R 32 , R 33 and R 34 are the same or different and represent a hydrogen atom, a fluorine atom or a C n F 2n+1 group, provided that any one of R 30 , R 31 , R 32 , R 33 and R 34 is a fluorine atom or a C n F 2n+1 group, and n represents an integer of 1 to 15); The following general formula (XC2): 【Chemistry 7】 (wherein R 40 , R 41 and R 42 are the same or different and represent a C t F 2t+1 group, where t represents an integer of 1 to 15); or The following general formula (XD1): 【Chemistry 8】 (wherein r is an integer of 1 to 6) An onium salt compound represented by the formula:

3. The R Ａ is represented by the following general formula (1-R Ａ ): 【Chemistry 9】 (In the formula, R １ represents a hydrogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkylthio group, a thio group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfinyl group, a sulfinyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfonyl group, a sulfonyl group having an optionally substituted 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted heterocyclic group, or an optionally substituted silyl group. R ２ represents a hydrogen atom or an optionally substituted C1-15 alkyl group. R ３ represents a hydrogen atom or an optionally substituted C1-15 alkyl group; Alternatively, the R １ , R ２ and R ３ Among these, two or three adjacent groups may be bonded to each other to form a saturated or unsaturated carbocyclic or heterocyclic ring. The saturated or unsaturated carbocyclic or heterocyclic ring may further have a substituent. * indicates the bonding position with the sulfur atom in the general formula (1). The onium salt compound according to claim 1, wherein the group is represented by the formula:

4. The R １ is a hydrogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group, a thio group having an optionally substituted 3-15 membered saturated or unsaturated carbocyclic ring, an optionally substituted heterocyclic group, or an optionally substituted silyl group; The R ２ represents a hydrogen atom or an optionally substituted C1-15 alkyl group; The R ３ represents a hydrogen atom or an optionally substituted C1-15 alkyl group; Alternatively, the R １ , R ２ and R ３ The onium salt compound according to claim 3, wherein two or three adjacent groups among the above may be bonded to each other to form a saturated or unsaturated carbocyclic or heterocyclic ring, and the saturated or unsaturated carbocyclic or heterocyclic ring may further have a substituent.

5. The R ５ and R ６ and these two groups are bonded to each other together with adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring, and the saturated or unsaturated carbocyclic ring may further have a substituent.

6. The R ４ The onium salt compound according to claim 1, wherein is an unsubstituted C1-15 alkyl group.

7. An acid generator comprising the onium salt compound according to any one of claims 1 to 6.

8. A polymerization initiator comprising the onium salt compound according to any one of claims 1 to 6.

9. A reactive composition comprising the onium salt compound according to any one of claims 1 to 6 and a reactive compound.

10. A polymer obtainable from the reactive composition of claim 9.

11. An adhesive, sealant, or resist containing the reactive composition according to claim 9.

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