Onium salt compound

Abstract

The purpose of the present disclosure is to provide an onium salt compound which has excellent solvent compatibility and excellent storage stability. The present disclosure relates to an onium salt compound which is represented by general formula (1). (In the formula, RA represents an optionally substituted C1-15 alkyl group or the like. R4 represents a hydrogen atom or the like. R5 and R6 are the same or different, and each represent a hydrogen atom or the like, or R5 and R6 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 additionally have a substituent. The dotted line indicates a single bond or a double bond. X- represents a boron anion which contains a fluorine-containing aromatic ring, or the like.)

Description

Onium salt compounds

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

[0002] In recent years, energy conservation has been required in various fields in response to social issues such as the SDGs. Light is widely used as an environmentally friendly energy source to meet this demand. For example, in industry, photosensitive materials that utilize light have been commercialized as adhesives, sealants, photoresists, and the like (see, for example, Patent Documents 1 to 3). Known examples of such photosensitive materials 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 an acid upon heating as a thermal acid generator. The reactive composition described in Patent Document 4, which is a mixture of an 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 having a benzothiazolium counter cation and an antimony counter anion.

[0005] However, the acid generators described in Patent Documents 5 and 6 use highly toxic antimony, and further have the problem of only dissolving 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 and increase in viscosity during long-term storage. Therefore, higher storage stability is required for the reactive compositions. Therefore, there is a strong demand for novel compounds with acid generating ability that are excellent in solubility in various solvents (hereinafter referred to as "solvent compatibility") and storage stability.

[0006] JP 2009-013315 A JP 2010-235862 A JP 2022-190822 A JP 2019-189698 A JP 02-268173 A JP 07-025863 A

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

[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: Item 1. General formula (1):

[0010]

[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. ４ 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, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic oxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic oxycarbonyl group, an optionally substituted aminocarbonyl group, or a carboxyl group. ５ and R ６are 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 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxy group, an optionally substituted C1-15 alkylcarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, represents an oxycarbonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, an aminocarbonyl group which may have a substituent, a carboxyl group, an amino group which may have a substituent, a C1-15 alkylthio group which may have a substituent, a thio group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group which may have a substituent, a sulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group which may have a substituent, a sulfonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, or a heterocyclic group which may have a substituent; 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 bond or a double bond. 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. Ａ is represented by the following general formula (1-R Ａ ):

[0012]

[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, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxycarbonyl group R represents 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, an optionally substituted C1-15 alkylsulfinyl group, a sulfinyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfonyl group, a sulfonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted heterocyclic group, or an optionally substituted silyl group. 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. 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; or １ , R ２ and R ３Among these, two or three adjacent groups may be bonded to each other to form a saturated or unsaturated carbocyclic ring or a heterocyclic ring. The saturated or unsaturated carbocyclic ring or the heterocyclic ring may further have a substituent. * indicates the bonding position to the sulfur atom in the general formula (1). Item 3. The onium salt compound according to Item 1, wherein the 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 an aminocarbonyl group, a carboxyl group, an optionally substituted C1-15 alkylthio group, an optionally substituted thio group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfinyl group, an optionally substituted sulfinyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfonyl group, an optionally substituted sulfonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted heterocyclic group, or an optionally substituted silyl group; ２ is a hydrogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group; ３ is a hydrogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group; or １ , R ２ and R ３Item 4. The onium salt compound according to Item 2, wherein two or three adjacent groups among X 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. － is represented by the general formula (XA1): － B (R Ｘ１ ) a(R Ｘ２ ) b (wherein R Ｘ１ is a fluorine atom or C ｎ F ２ｎ＋１ R represents a group. Ｘ２ represents 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 represents an integer of 1 to 3; general formula (XB1): － Ga(R Ｘ３ ) a(R Ｘ４ ) b (wherein R Ｘ３ is a fluorine atom or C ｎ F ２ｎ＋１ R represents a group. Ｘ４ represents 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;); General formula (XC1): － C (R Ｘ５ ) (R Ｘ６ ) (R Ｘ７ ) (wherein R Ｘ５ , R Ｘ６ and R Ｘ７ are the same or different, and C ｔ F ２ｔ＋１ a sulfonyl group having a group; or at least one C ｔ F ２ｔ＋１represents a phenylsulfonyl group having a group, and t represents an integer of 1 to 15; or a group represented by general formula (XD1):

[0014]

[0015] (wherein r represents an integer of 1 to 6); or a cyclic sulfonimide anion having a fluorine atom represented by the following general formula (XE1): P(RX ８ ) c (RX ９ ) d) a phosphorus anion containing a fluorine-containing alkyl group (wherein R X ８ is CuF ２ｕ＋１ represents the 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 an integer of 0 to 5. c+d represents 6. Item 5. The onium salt compound according to any one of Items 1 to 3, wherein X － is represented by the following general formula (XA2):

[0016]

[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 Any one of the following is a fluorine atom or C ｎ F ２ｎ＋１ A boron anion represented by general formula (XB1):

[0018]

[0019] (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＋１group, provided that the R ３５ , R ３６ , R ３７ , R ３８ and R ３９ Any one of the following is a fluorine atom or C ｎ F ２ｎ＋１ a gallium anion represented by the following general formula (XC2):

[0020]

[0021] (In the formula, R ４０ , R ４１ and R ４２ are the same or different, and C ｔ F ２ｔ＋１ represents a group, and t represents an integer of 1 to 15; a carbon anion represented by general formula (XD1):

[0022]

[0023] (wherein r represents an integer of 1 to 6); or a cyclic sulfonimide anion having a fluorine atom represented by the following general formula (XE1): P(RX ８ ) c (RX ９ ) d) a phosphorus anion containing a fluorine-containing alkyl group (wherein R X ８ is CuF ２ｕ＋１ represents the 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 an integer of 0 to 5. c+d represents 6. Item 6. The onium salt compound according to any one of Items 1 to 4, wherein R ５ and R ６ and the onium salt compound according to any one of Items 1 to 5, wherein 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. ４is an optionally substituted C1-15 alkyl group (an unsubstituted C1-15 alkyl group or a substituted C1-15 alkyl group). Item 8. An acid generator containing the onium salt compound according to any one of items 1 to 7. Item 9. A polymerization initiator containing the onium salt compound according to any one of items 1 to 7. Item 10. A reactive composition containing the onium salt compound according to any one of items 1 to 7 and a reactive compound. Item 11. A polymer obtained from the reactive composition according to item 10. Item 12. An adhesive, sealant, or resist containing the reactive composition according to item 10. Item 13. The reactive composition according to item 10, which is used for an adhesive, sealant, or resist. Item 14. Use of the onium salt compound according to any one of items 1 to 7 as an acid generator. Item 15. Use of the onium salt compound according to any one of items 1 to 7 as a polymerization initiator. Item 16. Use of the reactive composition according to item 10 or 13 for a polymer. Item 17. Use of the reactive composition according to item 10 or 13 for an adhesive. Item 18. Use of the reactive composition according to item 10 or 13 for an encapsulant. Item 19. Use of the reactive composition according to item 10 or 13 for a resist.

[0024] Section 1-1. General formula (1):

[0025]

[0026] (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. 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. ５ and R ６ are the same or different and represent a hydrogen atom or an optionally substituted C1-15 alkyl group;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 bond or a double bond. X － is represented by the following general formula (XA2):

[0027]

[0028] (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 Any one of the following is a fluorine atom or C ｎ F ２ｎ＋１ and n represents an integer of 1 to 15; a boron anion represented by the following general formula (XC2):

[0029]

[0030] (In the formula, R ４０ , R ４１ and R ４２ are the same or different, and C ｔ F ２ｔ＋１ represents a group, and t represents an integer of 1 to 15; a carbon anion represented by the following general formula (XD1):

[0031]

[0032] (wherein r represents an integer of 1 to 6), or a cyclic sulfonimide anion having a fluorine atom represented by the following general formula (XE1): P(RX ８ ) c (RX ９ )d (wherein, RX ８ is CuF ２ｕ＋１ represents the group RX ９represents 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. ) is a phosphorus anion containing a fluorine-containing alkyl group. ) Onium salt compounds represented by General Formula (1):

[0033]

[0034] (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. ４ represents an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. ５ and R ６ are the same or different and represent a hydrogen atom; 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 bond or a double bond. X － is represented by the following general formula (XA2):

[0035]

[0036] (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 Any one of the following is a fluorine atom or C ｎ F ２ｎ＋１ and n represents an integer of 1 to 15; a boron anion represented by the following general formula (XC2):

[0037]

[0038] (In the formula, R ４０ , R ４１ and R ４２ are the same or different, and C ｔ F ２ｔ＋１ and t represents an integer of 1 to 15; or a carbon anion represented by the following general formula (XD1):

[0039]

[0040] (wherein r represents an integer of 1 to 6) is a fluorine atom-containing cyclic sulfonimide anion. Ａ is represented by the following general formula (1-R Ａ ):

[0041]

[0042] (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. ２ represents a hydrogen atom or an optionally substituted C1-15 alkyl group. ３ represents a hydrogen atom or an optionally substituted C1-15 alkyl group; or １ , R ２ and R ３Among these, two or three adjacent groups may be bonded to each other to form a saturated or unsaturated carbocyclic ring or a heterocyclic ring. The saturated or unsaturated carbocyclic ring or the heterocyclic ring may further have a substituent. * indicates the bonding position to the sulfur atom in the general formula (1). The onium salt compound according to Item 1, wherein 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; ２ is a hydrogen atom or an optionally substituted C1-15 alkyl group; ３ is a hydrogen atom or an optionally substituted C1-15 alkyl group; or １ , R ２ and R ３ Among the above, two or three adjacent groups 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 and R ６ The onium salt compound according to Item 1-1, wherein these two groups are bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring, and the saturated or unsaturated carbocyclic ring may further have a substituent. ４is an unsubstituted C1 to C15 alkyl group. Item 7-1. An acid generator containing the onium salt compound according to any one of Items 1-1 to 6-1. Item 8-1. A polymerization initiator containing the onium salt compound according to any one of Items 1-1 to 6-1. Item 9-1. A reactive composition containing the onium salt compound according to any one of Items 1-1 to 6-1 and a reactive compound. Item 10-1. A polymer obtained from the reactive composition according to Item 9-1. Item 11-1. An adhesive, sealant, or resist containing the reactive composition according to Item 9-1.

[0043] 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.

[0044] According to the present disclosure, a novel onium salt compound having excellent solvent compatibility and excellent storage stability can be provided. Furthermore, the onium salt compound of the present disclosure can function not only as an acid generator but also as a radical generator.

[0045] 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.

[0046] Onium Salt Compound 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.

[0047]

[0048] Here, R in the general formula (1) ４represents 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, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic oxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic oxycarbonyl group, an optionally substituted aminocarbonyl group, or a carboxyl group. ４ Examples of R include an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, an optionally substituted C2-15 alkynyl group, and an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group. ４ is a C1-15 alkyl group which may have a substituent (an unsubstituted C1-15 alkyl group and a substituted C1-15 alkyl group). ４ The alkyl group is a C1-6 alkyl group which may have a substituent (an unsubstituted C1-6 alkyl group and a substituted C1-6 alkyl group).

[0049] R ５ and R ６are 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 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxy group, an optionally substituted C1-15 alkylcarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, represents an oxycarbonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, an aminocarbonyl group which may have a substituent, a carboxyl group, an amino group which may have a substituent, a C1-15 alkylthio group which may have a substituent, a thio group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group which may have a substituent, a sulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group which may have a substituent, a sulfonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, or a heterocyclic group which may have a substituent; 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.

[0050] Among them, the preferred R ５ is a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a C1-15 alkyl group which may have a substituent. ５ is a hydrogen atom or an optionally substituted C1-15 alkyl group. ５ is a hydrogen atom or an unsubstituted C1-6 alkyl group. ６is a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a C1-15 alkyl group which may have a substituent. ６ is a hydrogen atom or an optionally substituted C1-15 alkyl group. ６ is a hydrogen atom or an unsubstituted C1-6 alkyl group.

[0051] 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.

[0052] The R ５ and R ６ When each of these carbon atoms bond to each other together with the adjacent carbon atom to form a saturated or unsaturated carbocyclic ring, the saturated or unsaturated carbocyclic ring is preferably a benzene ring (also referred to as a phenyl ring) or a naphthalene ring. Here, when the saturated or unsaturated carbocyclic ring is a benzene ring, the compound represented by general formula (1) refers to 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 naphthalene rings include 1,2-naphthalene, 2,3-naphthalene, and 3,4-naphthalene. A benzene ring is more preferred as the saturated or unsaturated carbocyclic ring.

[0053] The dotted lines indicate single or double bonds.

[0054] 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.

[0055] R Ａrepresents 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.

[0056] The R Ａ is represented by the following general formula (1-R Ａ ):

[0057]

[0058] A group represented by the following formula is preferred.

[0059] Here, the general formula (1-R Ａ ) in 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, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxycarbonyl group 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.

[0060] Among them, the preferred R １Examples of the alkyl group 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 and optionally substituted aminocarbonyl groups, carboxyl groups, optionally substituted C1-15 alkylthio groups, optionally substituted thio groups having a 3-15-membered saturated or unsaturated carbocyclic ring, optionally substituted C1-15 alkylsulfinyl groups, optionally substituted sulfinyl groups having a 3-15-membered saturated or unsaturated carbocyclic ring, optionally substituted C1-15 alkylsulfonyl groups, optionally substituted sulfonyl groups having a 3-15-membered saturated or unsaturated carbocyclic ring, optionally substituted heterocyclic groups, and optionally substituted silyl groups.

[0061] More preferred R １Examples thereof include a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 1> below, a C2-15 alkenyl group which may have one or more substituents selected from <Group 1> below, a C2-15 alkynyl group which may have one or more substituents selected from <Group 1> below, a 3- to 15-membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 3> below, a C1-15 alkylcarbonyl group which may have one or more substituents selected from <Group 1> below, a carbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 3> below, a C1-15 alkoxycarbonyl group which may have one or more substituents selected from <Group 1> below, an oxycarbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 3> below, and one or more Examples of the alkylthio group include 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.

[0062] More preferred R １Examples of the alkyl group include a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, a C2-15 alkenyl group which may have one or more substituents selected from <Group 2> below, a C2-15 alkynyl group which may have one or more substituents selected from <Group 2> below, a 3- to 15-membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below, a C1-15 alkylcarbonyl group which may have one or more substituents selected from <Group 2> below, a carbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 4> below, a C1-15 alkoxycarbonyl group which may have one or more substituents selected from <Group 2> below, an oxycarbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring which may have one or more substituents selected from <Group 4> below, and one or more alkyl groups selected from <Group 5> below. Examples of the alkylsulfonyl group include 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.

[0063] 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. ２is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from the following <Group 1>, or a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from the following <Group 3>. 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.

[0064] R ３ represents a hydrogen atom, a halogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic group. ３ is a hydrogen atom, a C1-15 alkyl group which may have one or more substituents selected from the following <Group 1>, and a 3-15 membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from the following <Group 3>. 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.

[0065] 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.

[0066] A preferred saturated or unsaturated carbocyclic ring is a C3-15 carbocyclic ring selected from <Group 3> below, which may have at least one or more substituents. A more preferred saturated or unsaturated carbocyclic ring is a C3-15 carbocyclic ring selected from <Group 4> below, which may have at least one or more substituents. Even more preferred saturated or unsaturated carbocyclic rings are 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.

[0067] A preferred heterocycle is a heterocycle which may have at least one substituent selected from the following <Group 3>. A more preferred heterocycle is a heterocycle which may have at least one substituent selected from the following <Group 4>. A still more preferred heterocycle is succinimide (maleimide) which may have at least one substituent selected from the group consisting of a substituted or unsubstituted phenyl group and an oxo group.

[0068] * indicates the bonding position with the sulfur atom in the general formula (1).

[0069] X － is a boron anion containing a fluorine-containing aromatic ring (XA － ), fluorine-containing aromatic ring-containing gallium anion (XB － ), a carbon anion containing a fluorine-containing sulfonyl group (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.)

[0070] Here, preferred X － Examples of the compound represented by the general formula (XA1): － B (R Ｘ１ ) a(R Ｘ２ ) b (wherein R Ｘ１ is a fluorine atom or C ｎ F ２ｎ＋１ R represents a group. Ｘ２ represents 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;

[0071] General formula (XB1): － Ga(R Ｘ３ ) a(R Ｘ４ ) b (wherein R Ｘ３ is a fluorine atom or C ｎ F ２ｎ＋１ R represents a group. Ｘ４ represents 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;

[0072] General formula (XC1): － C (R Ｘ５ ) (R Ｘ６ ) (R Ｘ７ ) (wherein R Ｘ５ , R Ｘ６ and R Ｘ７ are the same or different, and 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;

[0073] General formula (XD1):

[0074]

[0075] (wherein r is an integer of 1 to 6), a cyclic sulfonimide anion having a fluorine atom; or

[0076] General formula (XE1): P(R Ｘ８ ) c (R Ｘ９ ) a phosphorus anion containing a fluorine-containing alkyl group represented by formula d (wherein R Ｘ８ is C ｕ F ２ｕ＋１ R represents a group. 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.

[0077] More preferred examples of the boron anion represented by XA1 include those represented by the following general formula (XA2):

[0078]

[0079] (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 Any one of the following is a fluorine atom or C ｎ F ２ｎ＋１ n is an integer of 1 to 15.

[0080] Here, the substituent R in the general formula (XA2) ３０ , R ３１ , R ３２ , R ３３ and R ３４ The preferred groups for R are shown below. ３０is a hydrogen atom, a fluorine atom, or a trifluoromethyl group. ３１ is a hydrogen atom, a fluorine atom, or a trifluoromethyl group. ３２ is a hydrogen atom, a fluorine atom, or a trifluoromethyl group. ３３ is a hydrogen atom, a fluorine atom, or a trifluoromethyl group. ３４ are a hydrogen atom, a fluorine atom, and a trifluoromethyl group.

[0081] 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 ３０ is 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.

[0082] Even more preferred boron anions represented by general formula (XA2) are boron anions represented by the following general formulas (XA2-1), (XA2-2), and (XA2-3).

[0083]

[0084] More preferred gallium anions represented by XB1 include those represented by the following general formula (XB2):

[0085]

[0086] (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 Any one of the following is a fluorine atom or C ｎ F ２ｎ＋１ n is an integer of 1 to 15.

[0087] Here, the substituent R in the general formula (XB2) ３５ , R ３６ , R ３７ , R ３８ and R ３９ The preferred groups for R are shown below. ３５ is a hydrogen atom, a fluorine atom, or a trifluoromethyl group. ３６ is a hydrogen atom, a fluorine atom, or a trifluoromethyl group. ３７ is a hydrogen atom, a fluorine atom, or a trifluoromethyl group. ３８ is a hydrogen atom, a fluorine atom, or a trifluoromethyl group. ３９ are a hydrogen atom, a fluorine atom, and a trifluoromethyl group.

[0088] 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, R ３８ 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.

[0089] More preferred carbon anions (also called methide anions) represented by XC1 include those represented by the following general formula (XC2):

[0090]

[0091] (In the formula, R ４０ , R ４１ and R ４２ are the same or different, and C ｔ F ２ｔ＋１ represents a group; and t represents an integer of 1 to 15.

[0092] Here, the substituent R in the general formula (XC2) ４０ , R ４１ and R４２ The preferred groups for R are shown below. ４０ is a difluoromethyl group, a trifluoromethyl group, or a pentafluoroethyl group. ４１ is a difluoromethyl group, a trifluoromethyl group, or a pentafluoroethyl group. 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.

[0093] Even more preferred carbon anions represented by the general formula (XC2) include those represented by the following general formula (XC2-1):

[0094]

[0095] It is a carbon anion represented by the formula:

[0096] More preferred cyclic sulfonimide anions represented by general formula (XD1) are those in which r is an integer of 2 to 5.

[0097] Even more preferred cyclic sulfonimide anions represented by the general formula (XD1) are cyclic sulfonimide anions represented by the following general formulas (XD1-1) and (XD1-2).

[0098]

[0099] General formula (XE1): P(R Ｘ８ ) c (R Ｘ９ The phosphorus anion containing a fluorine-containing alkyl group represented by d is, for example, (CF ３ CF ２ ) ２ PF ４ － , (CF ３ CF ２ ) ３ PF ３ －, ((CF ３ ) ２ CF) ２ PF ４ － , ((CF ３ ) ２ CF) ３ PF ３ － , (CF ３ CF ２ CF ２ ) ２ PF ４ － , (CF ３ CF ２ CF ２ ) ３ PF ３ － , ((CF ３ ) ２ CFCF ２ ) ２ PF ４ － , ((CF ３ ) ２ CFCF ２ ) ３ PF ３ － , (CF ３ CF ２ CF ２ CF ２ ) ２ PF ４ － , and (CF ３ CF ２ CF ２ CF ２ ) ３ PF ３ － Among these, preferred phosphorus anions containing a fluorine-containing alkyl group include anions represented by (CF ３ CF ２ ) ３ PF ３ － , (CF ３ CF ２ CF ２ ) ３ PF ３ － , ((CF ３ ) ２ CF) ３ PF ３－ , ((CF ３ ) ２ CF) ２ PF ４ － , ((CF ３ ) ２ CFCF ２ ) ３ PF ３ － , and ((CF ３ ) ２ CFCF ２ ) ２ PF ４ － It is an anion represented by the formula:

[0100] Japanese Patent Laid-Open Publication No. 2007-224183 (Patent Document 7) describes an energy ray-sensitive acid generator (Claim 1). Paragraph

[0192] of the same document lists 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 these are not included in the Examples section of the document. Since the document does not disclose how the compounds (1Z-1) and (1Z-2) were produced or what effects were achieved, it cannot be said that the document discloses the above invention. It is preferable that the onium salt compounds of the present disclosure exclude compounds represented by the following formulas (1Z-1) and (1Z-2).

[0101]

[0102] Preferable onium salt compounds are compounds represented by the following general formula (1A-1), (1A-2), (1A-3), and (1A-4).

[0103] Among the onium salt compounds represented by the general formula (1), the R ５ and R ６However, 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 (1A-2).

[0104]

[0105] Here, R in general formula (1A-1) and general formula (1A-2) Ａ , R ４ and X － is the same as above. ５ and R ６ 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 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxy group, an optionally substituted C1-15 alkylcarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, and a heterocyclic group which may have a substituent.

[0106] In addition, among the onium salt compounds represented by the general formula (1), ５ and R ６are bonded to each other together with the adjacent carbon atoms to form a saturated or unsaturated carbocyclic ring, the compound is an onium salt compound represented by the following general formula (1A-3) (hereinafter, may be referred to as a "benzothiazolium salt"), or an onium salt compound represented by the following general formula (1A-4).

[0107]

[0108] (In the formula, R Ａ , R ４ and X － is the same as above. ７ , R ８ , R ９ and R １０ 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 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxy group, an optionally substituted C1-15 alkylcarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, or a heterocyclic group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, an oxycarbonyl group having an optionally substituted 3- to 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 having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a thio group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a sulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, or a heterocyclic group having an optionally substituted heterocyclic group. ７ , R ８ , R ９ and R １０At 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.

[0109] 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>. ８ is one or more substituents selected from <Group 3>. ８ is one or more substituents selected from <Group 4>. ９ is one or more substituents selected from <Group 3>. ９ is one or more substituents selected from <Group 4>. １０ is one or more substituents selected from <Group 3>. １０ is one or more substituents selected from <Group 4>.

[0110]

[0111] (In the formula, R Ａ , R ４ and X － is the same as above. 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 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 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxy group, an optionally substituted C1-15 alkylcarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, or a heterocyclic group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, an oxycarbonyl group having an optionally substituted 3- to 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 having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a thio group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a sulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, or a heterocyclic group having an optionally substituted heterocyclic group. 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.

[0112] In the present disclosure, a preferred onium salt is a compound represented by the following general formula (1B).

[0113]

[0114] Here, R in the formula１ , R ２ , R ３ , R ４ , R ５ , R ６ , X － and dotted lines are the same as above.

[0115] Examples of the compound represented by general formula (1B) include a compound represented by the following general formula (1B-1), a compound represented by general formula (1B-2), a compound represented by general formula (1B-3), and a compound represented by general formula (1B-4).

[0116]

[0117] Here, R in the formula １ , R ２ , R ３ , R ４ , R ５ , R ６ and X － is the same as above.

[0118]

[0119] Here, R in the formula １ , R ２ , R ３ , R ４ , R ５ , R ６ and X － is the same as above.

[0120]

[0121] where R １ , R ２ , R ３ , R ４ , R ７ , R ８ , R ９ , R １０ and X － is the same as above.

[0122]

[0123] 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.

[0124] 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).

[0125] Here, R in general formula (1C) ４ , R ５ , R ６ , dotted line and X － is the same as above. 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 optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxy group, an optionally substituted C1-15 alkylcarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, The R represents an oxycarbonyl group having an optionally substituted 3- to 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 3- to 15-membered saturated or unsaturated carbocyclic ring thio group, an optionally substituted C1-15 alkylsulfinyl group, a sulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfonyl group, a sulfonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, or an optionally substituted heterocyclic group. 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. 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 ２７ may be the same or different. In addition, the onium salt compounds encompassed by the present disclosure may be optical isomers.

[0126] Examples of the compound represented by general formula (1C) include a compound represented by the following general formula (1C-1), a compound represented by general formula (1C-2), a compound represented by general formula (1C-3), and a compound represented by general formula (1C-4).

[0127]

[0128] 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.

[0129]

[0130] 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.

[0131]

[0132] Here, R in the formula ４ , R ７ , 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.

[0133]

[0134] Here, R in the formula ４ , R１１ , 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.

[0135] 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. ２１ , R ２２ , R ２３ , R ２４ and R ２５are the same or different and are a hydrogen atom, a hydroxyl group, a C1-15 alkyl group which may have one or more substituents selected from <Group 2> below, a C2-15 alkenyl group which may have one or more substituents selected from <Group 2> below, a C2-15 alkynyl group which may have one or more substituents selected from <Group 2> below, a 3- to 15-membered saturated or unsaturated carbocyclic group which may have one or more substituents selected from <Group 4> below, a C1-15 alkoxy group which may have one or more substituents selected from <Group 2> below, a C1-15 alkylcarbonyl group which may have one or more substituents selected from <Group 2> below, and a C1-15 alkoxycarbonyl group which may have one or more substituents selected from <Group 2> below.

[0136] Preferred R ２６ is a hydrogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, and an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic group. 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.

[0137] Preferred R ２７ is a hydrogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, and an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic group. 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.

[0138] q is an integer of 1 to 6, preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

[0139] 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).

[0140] Here, R in general formula (1D) ４ , R ５ , R ６ , dotted line and X － is the same as above. ５０ , R ５１ and R ５２ 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 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxy group, an optionally substituted C1-15 alkylcarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, The R represents an oxycarbonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, an aminocarbonyl group which may have a substituent, a carboxyl group, an amino group which may have a substituent, a C1-15 alkylthio group which may have a substituent, a thio group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group which may have a substituent, a sulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group which may have a substituent, a sulfonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, or a heterocyclic group which may have a substituent. 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.５４ represents a hydrogen atom, a halogen atom, a hydroxyl group, an optionally substituted C1-15 alkyl group, or an optionally substituted 3- to 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 ５０ and 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 of 2 to 6, two or more R ５３ may be the same or different, and two or more R ５４ may be the same or different.

[0141] Examples of the compound represented by general formula (1D) include a compound represented by the following general formula (1D-1), a compound represented by general formula (1D-2), a compound represented by general formula (1D-3), and a compound represented by general formula (1D-4).

[0142]

[0143] 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.

[0144]

[0145] 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.

[0146]

[0147] 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.

[0148]

[0149] 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.

[0150] 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. ５０ , R ５１ , R ５２ , R ５３ and R ５４are 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- to 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.

[0151] Preferred R ５３ is a hydrogen atom, a C1-15 alkyl group which may have a substituent, or a 3-15 membered saturated or unsaturated carbocyclic group which may have a substituent. 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.

[0152] Preferred R ５４ is a hydrogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic group. 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.

[0153] q is an integer of 1 to 6, preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

[0154] 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).

[0155]

[0156] Here, R in general formula (1D) ４ , R ５ , R ６ , dotted line, and X － is the same as above. ６０ 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 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. 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.

[0157] 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).

[0158]

[0159] 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.

[0160]

[0161] 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.

[0162]

[0163] 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.

[0164]

[0165] 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.

[0166] Preferred R ６０ is a hydrogen atom, a C1-15 alkyl group which may have a substituent, or a 3-15 membered saturated or unsaturated carbocyclic group which may have a substituent. 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.

[0167] Preferred R ６１is a hydrogen atom or an optionally substituted C1-15 alkyl group. ６１ is a hydrogen atom or a C1-15 alkyl group which may have one or more substituents selected from the following <Group 2>.

[0168] Preferred R ６２ is a hydrogen atom or an optionally substituted C1-15 alkyl group. ６２ is a hydrogen atom or a C1-15 alkyl group which may have one or more substituents selected from the following <Group 2>.

[0169] Preferred R ６３ is a hydrogen atom or an optionally substituted C1-15 alkyl group. ６３ is a hydrogen atom or a C1-15 alkyl group which may have one or more substituents selected from the following <Group 2>.

[0170] Among the onium salt compounds represented by the above general formula (1), preferred compounds are those represented by the following general formula (1): 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, and R ５ and R ６ are the same or different and are a hydrogen atom or an optionally substituted C1-15 alkyl group; or ５ and R ６ These two groups may be bonded to each other together with the adjacent carbon atoms to form an unsaturated carbocyclic ring, which may further have a substituent; the dotted line is a single bond or a 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.

[0171] 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 ６ However, 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.

[0172] 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) above, 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>; or ７ , R ８ , R ９ and R １０At 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 general formula (XA2) above, a gallium anion represented by the general formula (XB2) above, a carbon anion represented by the general formula (XC2) above, or a cyclic sulfonimide anion represented by the general formula (XD1) above.

[0173] Among the onium salt compounds represented by the above general formula (1A-3), particularly preferred onium salts are those represented by the following general formula (1A-3): 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>; or 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 general formula (XA2) above, a gallium anion represented by the general formula (XB2) above, a carbon anion represented by the general formula (XC2) above, or a cyclic sulfonimide anion represented by the general formula (XD1) above.

[0174] The following provides definitions of terms used in this specification.

[0175] The notation Cx-y can be rephrased as Cx-Cy or carbon number x-y. The notation Cx-Cy means having x to y carbon atoms. Here, 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.

[0176] 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.

[0177] The halogen atom is not particularly limited, and specific examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0178] The carbon chain in "alkyl", "alkenyl", "alkynyl", "alkoxy", etc. may be a straight chain or branched chain.

[0179] The C1-15 alkyl group is not particularly limited, and specific examples 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, and a 1,2,2-trimethylpropyl group. In this specification, n- means normal, sec- means secondary, t- means tertiary, and i- means iso.

[0180] 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 may be either the E- or Z-isomer alone, or a mixture of the E- and Z-isomers in any proportion, 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 thereof include vinyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 4-methyl-3-pentenyl group, 3-methyl-2-pentenyl group, 1-methylvinyl group, 2-methylvinyl group, 1,2-dimethylvinyl group, 2,2-dimethylvinyl group, 1,2,2-trimethylvinyl group, etc. Examples of substituted C2-15 alkenyl groups include 1-phenylvinyl group, 2-phenylvinyl group, etc.

[0181] 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 thereof include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1,1-dimethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, and 5-hexynyl.

[0182] The C1-15 alkoxy group refers to a C1-15 alkyl group bonded via an oxygen atom. The C1-15 alkoxy group is not particularly limited, and specific examples include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, isopentyloxy, 1-methylbutoxy, 2-methylbutoxy, neopentyloxy, 1-ethylpropyloxy, 1,2-dimethylpropyloxy, hexyloxy, and 1-methylpentyloxy. group, 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.

[0183] The oxy 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 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 oxy groups having a saturated carbocyclic ring such as a cyclopropyloxy group or a cyclohexyloxy group; and oxy groups having an unsaturated carbocyclic ring such as a cyclopropenyloxy group, a cyclohexenyloxy group, or a phenoxy group.

[0184] 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.

[0185] 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.

[0186] 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.

[0187] 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, and an azulenyl group. An aryl group can also be referred to as an aromatic hydrocarbon group. Examples of substituted C6-14 aryl groups include a tolyl group, a xylyl group, a mesityl group, and a biphenyl group.

[0188] The heterocyclic group is not particularly limited, and examples thereof include saturated or unsaturated heterocyclic groups, such as 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.

[0189] 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.

[0190] 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 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.

[0191] 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.

[0192] 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.

[0193] 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, a thiazolopyridyl group (e.g., a thiazolo[3,2-a]pyridyl group, a thiazolo[5,4-b]pyridyl group, a thiazolo[4,5-b]pyridyl group), an isothiazolopyridyl group (e.g., an isothiazolo[2,3-a]pyridyl group, an isothiazolo[4,5-b]pyridyl group, an isothiazolo[5,4-b]pyridyl group), an imidazopyridyl group (e.g., an imidazo[1,2-a]pyridyl group, an imidazo[4,5-b]pyridyl group), a pyrazolopyridyl group (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.

[0194] The oxy group having a saturated or unsaturated heterocycle refers to the saturated or unsaturated heterocycle group 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.

[0195] 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 thereof 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.

[0196] The carbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring refers to a group in which the aforementioned 3- to 15-membered saturated or unsaturated carbocyclic ring is bonded via a carbonyl. The carbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring is not particularly limited, and specific examples thereof include a cyclopropylcarbonyl group, a cyclohexylcarbonyl group, a cyclopropenylcarbonyl group, a cyclohexenylcarbonyl group, and a phenylcarbonyl group (benzoyl group).

[0197] The C1-15 alkoxycarbonyl group refers to the above-mentioned C1-15 alkoxy group bonded via a carbonyl. The C1-15 alkoxycarbonyl group is not particularly limited, and specific examples thereof 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.

[0198] The oxycarbonyl 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 an oxycarbonyl. Specific examples of the oxycarbonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring include, but are not limited to, oxycarbonyl groups having a saturated carbocyclic ring such as a cyclopropyloxycarbonyl group or a cyclohexyloxycarbonyl group; and oxycarbonyl groups having an unsaturated carbocyclic ring such as a cyclopropenyloxycarbonyl group, a cyclohexenyloxycarbonyl group, or a phenoxycarbonyl group.

[0199] Examples of the optionally substituted aminocarbonyl group include R ７０ R ７１ NCO group, etc. ７０ and R ７１ are the same or different and represent a hydrogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, or an optionally substituted C2-15 alkynyl group.

[0200] Examples of the optionally substituted amino group include R ７２ R ７３ In the formula, the R ７２ and R ７３ are the same or different and represent a hydrogen atom, an optionally substituted C1-15 alkyl group, an optionally substituted C2-15 alkenyl group, or an optionally substituted C2-15 alkynyl group.

[0201] The C1-C15 alkylthio group refers to the aforementioned C1-15 alkyl group bonded via a thio group (sulfide). The C1-15 alkylthio group is not particularly limited, and examples thereof include methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, t-butylthio, pentylthio, and isopentylthio.

[0202] 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 carbocyclic ring is not particularly limited, and specific examples thereof include a cyclopropylthio group, a cyclohexyloxythio group, a cyclopropenylthio group, and a phenylthio group.

[0203] The C1-C15 alkylsulfinyl group refers to a group in which the C1-15 alkyl group is 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.

[0204] The sulfinyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring refers to a group in which the aforementioned 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 carbocyclic ring is not particularly limited, and specific examples thereof include a cyclopropylsulfinyl group, a cyclohexyloxysulfinyl group, a cyclopropenylsulfinyl group, and a phenylsulfinyl group.

[0205] The C1-C15 alkylsulfonyl group refers to a group in which the above-mentioned C1-15 alkyl group is 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.

[0206] The sulfonyl group having a 3- to 15-membered saturated or unsaturated carbocyclic ring refers to a group in which the aforementioned 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 carbocyclic ring is not particularly limited, and specific examples thereof include a cyclopropylsulfonyl group, a cyclohexyloxysulfonyl group, a cyclopropenylsulfonyl group, and a phenylsulfonyl group.

[0207] Examples of the optionally substituted silyl group include R ８０ R ８１ R ８２ Examples of R include a Si group. 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.

[0208] The substituents in the present disclosure are not particularly limited, and examples thereof 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>, and the like.

[0209] 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.

[0210] <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- to 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.

[0211] 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.

[0212] <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 optionally having at least one substituent selected from the group consisting of 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 (C1-6 alkoxy)carbonyl 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 and a phenyl group optionally having at least one substituent selected from the group consisting of 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.

[0213] 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.

[0214] <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.

[0215] 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.

[0216] 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.

[0217] <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.

[0218] The amino group may have one or more substituents selected from the following <Group 5>, and when the amino group has two or more substituents, the substituents may be the same or different.

[0219] <Group 5>: a C1-6 alkyl group; a (C1-6 alkoxy)C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 alkynyl group; a C3-6 cycloalkyl group; a (C1-6 alkyl)carbonyl group; a (C3-6 cycloalkyl)carbonyl group; and a (C1-6 alkoxy)carbonyl group.

[0220] 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.

[0221] The silyl group may have one or more substituents selected from the following <Group 6>, and when the silyl group has two or more substituents, the substituents may be the same or different.

[0222] <Group 6>: C1-6 alkyl groups; C2-6 alkenyl groups; C2-6 alkynyl groups; C3-6 cycloalkyl groups; and phenyl groups which may have one or more C1-6 alkyl groups.

[0223] 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.

[0224] The C1-6 haloalkyl group refers to the above-mentioned C1-6 alkyl group in which a hydrogen atom is optionally 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 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.

[0225] A haloalkenyl group refers to the C2-C6 alkenyl group in which one or more hydrogen atoms have been arbitrarily 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 restriction on the number of substitutions, as long as they can exist as substituents. The C2-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.

[0226] The C2-6 haloalkynyl group refers to the above-mentioned C2-6 alkynyl group in which a hydrogen atom is optionally 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 C2-6 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.

[0227] The C1-6 haloalkoxy group refers to the C1-C6 alkoxy group in which a hydrogen atom is optionally 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 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.

[0228] The halocycloalkyl group refers to the above-mentioned C3-15 cycloalkyl group in which a hydrogen atom is optionally substituted with one or more halogen atoms. The halocycloalkenyl group refers to the above-mentioned C3-15 cycloalkenyl group in which a hydrogen atom is optionally substituted with one or more halogen atoms.

[0229] There is no particular limitation 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.

[0230] (Scheme 1)

[0231] In the formula, R Ａ , R ４ , R ５ , R ６, X － The dotted lines and the dashed 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 fluoro, chloro, bromo, and iodo groups; mesylate, tosyl, nosyl, cyano, alkyl sulfate, and triflate groups. Y is a counter anion. Examples of counter anions include fluoro, chloro, bromo, iodo, mesylate, tosyl, nosyl, cyano, alkyl sulfate, and triflate groups. M is a cation. Examples of cations include hydrogen ions; alkali metal ions such as sodium ions, lithium ions, potassium ions, rubidium ions, cesium ions, and beryllium ions; alkaline earth metal ions such as magnesium ions, calcium ions, strontium ions, and barium ions; metal ions such as scandium ions, titanium ions, zirconium ions, vanadium ions, niobium ions, chromium ions, molybdenum ions, manganese ions, iron ions, ruthenium ions, cobalt ions, rhodium ions, nickel ions, palladium ions, copper ions, silver ions, zinc ions, cadmium ions, aluminum ions, gallium ions, tin ions, and antimony ions; and ammonium ions such as tetramethylammonium and tetrabutylammonium.

[0232] (Step I) Step I is a step shown in the following scheme I.

[0233]

[0234] In the formula, R Ａ , R ５ , R ６ , L and dotted lines are the same as above.

[0235] 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.

[0236] 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.

[0237] 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), as long as the target 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.

[0238] It is also possible to use a compound having a double bond instead of the compound represented by general formula (3) and 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.

[0239] 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 to 3 equivalents 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, and tin chloride. These acids can be used alone or in combination of two or more in any ratio. The type of base is not particularly limited, and examples thereof include inorganic salts such as lithium carbonate, sodium hydrogencarbonate, sodium carbonate, potassium hydrogencarbonate, 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 desired ratio.

[0240] Examples of the solvent to be used in Step I 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; ester-based solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile-based solvents such as acetonitrile; amide-based solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; 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; 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.

[0241] 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).

[0242] In Step I, the reaction temperature is not particularly limited and is typically about 20° C. to 100° C. The reaction time is not particularly limited and is typically about 1 to 72 hours.

[0243] 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 an aqueous solution is used, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; 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 of two or more in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity or yield.

[0244] 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.

[0245] 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 solvent distillation can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, distillation, column chromatography, etc.

[0246] (Step II) Step II is a step shown in the following scheme II.

[0247]

[0248] In the formula, R Ａ , R ４ , R ５ , R ６ , Y and dotted lines are the same as above.

[0249] 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.

[0250] 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 compounds 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.

[0251] 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; organic solvents such as nitro-based solvents such as nitromethane; and water. These solvents can be used alone or in combination of two or more in any ratio. 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.

[0252] 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).

[0253] 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.

[0254] In Step II, a catalyst for promoting 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; cesium halides such as cesium bromide and cesium iodide; halogens such as chlorine, bromine, and iodine; Lewis acids such as boron trifluoride, boron trichloride, boron tribromide, magnesium chloride, magnesium bromide, zinc chloride, tin chloride, iron chloride, aluminum chloride, gallium chloride, titanium tetrachloride, zirconium tetrachloride, and acidic ion exchange resins; and desiccants such as polymer adsorbents (molecular sieves, zeolites, alumina, silica gel, etc.) and inorganic salts (calcium chloride, anhydrous magnesium sulfate, quicklime, anhydrous sodium sulfate, anhydrous calcium sulfate, anhydrous aluminum sulfate, etc.). These catalysts can be used alone or in combination of two or more in any ratio.

[0255] As a post-treatment of the reaction, water or an appropriate aqueous solution can be added to the reaction mixture to perform a liquid separation operation. When an aqueous solution is used, 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.; a reducing agent such as ascorbic acid, sodium ascorbate, sodium erythorbate, tartaric acid, citric acid, a metal salt of formaldehyde sulfoxylate, sodium thiosulfate, sodium sulfite, sodium bisulfite, sodium metabisulfite, or ferric chloride; saline solution, etc. During the separation operation, it is possible to add, as necessary, a water-immiscible solvent, 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 of two or more in any desired ratio. The number of separations is not particularly limited and can be performed depending on the desired purity or yield.

[0256] 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.

[0257] 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 solvent distillation can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.

[0258] (Step III) Step III is a step shown in the following scheme III.

[0259] In the formula, R Ａ , R ４ , R ５ , R ６ , X － , Y, M and the dotted line are the same as above.

[0260] Step III is a step of reacting the compound represented by general formula (6) obtained in Step II with a compound represented by general formula (7) to produce a compound represented by general formula (1). Step III can be carried out, for example, in the presence of a solvent.

[0261] 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).

[0262] In step III, the compound represented by general formula (7) can be prepared, for example, by the reaction of MB(C ６ F ５ ) ４ , MB (C ６ H ４ F) ４ , MB (C ６ H ３ (CF ３ ) ２ ) ４ Boron compounds containing fluorine-containing aromatic rings, such as MGa(C ６ F ５ ) ４ gallium compounds containing a fluorine-containing aromatic ring, such as MC(SO ２ CF ３ ) ３ fluorine-containing sulfonyl group-containing carbon compounds such as MN(SO ２ CF ２ ) ２ CF ２ fluorine atom-containing cyclic sulfonimide compounds such as MPF ３ (C2F ５ ) ３Here, 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.

[0263] Examples of the solvent to be used in Step III 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; ester-based solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; nitrile-based solvents such as acetonitrile; amide-based solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; 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; 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.

[0264] 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).

[0265] In Step III, the reaction temperature is not particularly limited and may be, for example, 0°C to 50°C. The reaction time is also 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 an aqueous solution is used, any of the following can be used: an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, or the like; an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, or the like; saline solution, etc. During the separation operation, it is possible to add, as necessary, a water-immiscible solvent, such as a benzene-based solvent (e.g., toluene, xylene, benzene, chlorobenzene, dichlorobenzene, etc.); an ester-based solvent (e.g., ethyl acetate, isopropyl acetate, butyl acetate, etc.); an ether-based solvent (e.g., diethyl ether, diisopropyl ether, methyl t-butyl ether, etc.); a halogen-based solvent (e.g., dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc.); or a hydrocarbon-based solvent (e.g., hexane, heptane, cyclohexane, methylcyclohexane, etc.). These solvents can be used alone or in combination of two or more in any proportion. The number of separations is not particularly limited and can be carried out depending on the desired purity or yield.

[0266] 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.

[0267] 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 solvent distillation can be purified by washing with an appropriate solvent, reprecipitation, recrystallization, column chromatography, etc.

[0268] The onium salt compound of the present disclosure can be used for various applications, 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.

[0269] 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 various types of solvents. Examples of solvents that can dissolve 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; amide-based solvents such as N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; urea-based solvents such as 1,3-dimethyl-2-imidazolidinone; dichloromethane, dichloroethane, organic solvents such as ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.; nitro-based solvents such as nitromethane, etc.; carbonate-based solvents such as propylene carbonate, dimethyl carbonate, diethyl carbonate, dipropyl carbonate, ethylene carbonate, etc.; ester-based solvents such as PGMAc (propylene glycol 1-monomethyl ether 2-acetate), ethyl acetate, isopropyl acetate, butyl acetate, etc.; "HP4032", "HP4032D", and "HP4032SS" (naphthalene-type epoxy resins) manufactured by DIC Corporation; "828US" and "jER (registered trademark, sometimes abbreviated hereinafter)" manufactured by Mitsubishi Chemical Corporation.) 828EL, "825", "jER828 (bisphenol A type epoxy resin); "jER807" and "1750" (bisphenol F type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "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. Examples of suitable solvents include liquid epoxy resins such as "EX-721" (glycidyl ester epoxy resin) manufactured by Nagase ChemteX Corporation; "Celloxide (registered trademark, hereinafter sometimes abbreviated) 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by Daicel Corporation; "PB-3600" (epoxy resin having a butadiene structure) manufactured by Daicel Corporation; and "ZX-1658" and "ZX-1658GS" (liquid 1,4-glycidylcyclohexane 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, preferred solvents are propylene carbonate, methyl isobutyl ketone, PGMAc (propylene glycol 1-monomethyl ether 2-acetate), toluene, Celloxide 2021P, and jER828. The storage stability means that when a reactive composition containing the onium salt compound of the present disclosure is stored, the onium salt does not decompose or the reactive composition does not gel, and is stable. Furthermore, the onium salt compound of the present disclosure also has excellent photoreactivity and thermal reactivity.

[0270] <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. Specific examples of the photopolymerization initiator include a photoradical polymerization initiator, a photocationic polymerization initiator, and a photoanionic polymerization initiator. Among the above photopolymerization initiators, a photoradical polymerization initiator or a photocationic polymerization initiator can be preferably used. Furthermore, the polymerization initiator of the present disclosure can 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, diaryliodonium salts, and the like; sulfonium salts such as triarylsulfonium salts, triarylpyrilium salts, benzylpyridinium thiocyanate, dialkylphenacylsulfonium salts, and dialkylhydroxyphenylphosphonium salts, and the like.

[0271] <Reactive Composition> The reactive composition of the present disclosure contains the onium salt compound of the present disclosure and a reactive compound. Here, the reactive composition can be rephrased 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. Examples of uses of the reactive composition of the present disclosure include acid generators, polymerization initiators, adhesives, sealants, resists, solubilizers, color-changeable materials, agricultural chemicals, and colorants. In addition, 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 with excellent insulating properties and excellent transparency.

[0272] The type of reactive compound is not particularly limited, and examples thereof include compounds having an acid labile group, compounds having a radical reactive group, etc. 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 an acid labile group such as those described in JP 2023-169223 A, which have a leaving group, and the leaving group is eliminated by 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; leuco dyes, triarylmethane dyes, diphenylmethane dyes, fluoran dyes, spiropyran dyes, rhodamine dyes, etc., as described in JP 2022-086976 A, compounds that develop color by reaction with acid (color-forming compounds), etc.

[0273] The compound having a radical reactive group is not particularly limited, and refers to a compound that reacts with a radical. Examples of compounds that react with a radical include compounds that react with a radical to give a cured product, as described in Japanese Patent No. 6464271. Examples of compounds that react with a radical include KAYARAD DPHA, KAYARAD DPHA-2C, KAYARAD PET-30, KAYARAD TMPTA, KAYARAD TPA-320, KAYARAD TPA-330, KAYARAD RP-1040, KAYARAD T-1420, KAYARAD D-310, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60, KAYARAD GPO-303 (manufactured by Nippon Kayaku Co., Ltd.), NK Ester A-TMPT, A-TMMT, A-TMM3, A-TMM3L, A-9550 (manufactured by Nippon Kayaku Co., Ltd.), and the like. Examples of the acrylic acid ester include esters of polyols and (meth)acrylic acid such as V#3PA, V#400, V#36095D, V#1000, V#1080, and Viscoat #802 (manufactured by Osaka Organic Chemical Industry Ltd.), and dendrimer-type multifunctional acrylates such as Sirius-501 and SUBARU-501 (manufactured by Osaka Organic Chemical Industry 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 UV-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 Co., Ltd.), Hicorp AU-2010, Hicorp AU-2020 (manufactured by Tokushiki Co., Ltd.), Aronix M-1960 (manufactured by Toagosei Co., Ltd.), Art Resin UN-3320HA, UN-3320HC, Other examples that can be used include tri- or higher functional urethane acrylate compounds such as UN-3320HS and UN-904 (manufactured by Negami Chemical Industrial Co., Ltd.), NK Oligo U-4HA and U-15HA (manufactured by Shin-Nakamura Chemical Co., Ltd.), and tri- or higher functional polyester compounds such as Aronix M-8100, M-8030 and M-9050 (manufactured by Toagosei Co., Ltd.) and KRM-8307 (manufactured by Daicel-Cytec Co., Ltd.).

[0274] The reactive compound is preferably a 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 a liquid at 25°C, as this provides excellent workability and low-temperature curing properties. The viscosity of the reactive compound at 25°C is not particularly limited.

[0275] Among 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.

[0276] 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.

[0277] Commercially available hydrogenated bisphenol A epoxy resins include, for example, YX-8000 and 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, for example, YL-6753 (manufactured by Mitsubishi Chemical Corporation).

[0278] 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.

[0279] 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.), LIKARESIN 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.

[0280] 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.

[0281] 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), EPICLON 830, 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, but are not limited thereto.

[0282] 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.

[0283] Examples of commercially available oxetane compounds include OXT-212, OXT-221, OXT-213, and OXT-101 (manufactured by Toagosei Co., Ltd.), but are not limited to these.

[0284] 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. Examples of commercially available vinyl compounds include 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.), and the like, but are not limited to these.

[0285] The silyl compound is not particularly limited, and examples thereof include dialkoxysilane, trialkoxysilane, tetraalkoxysilane, 3-glycidoxypropyltrimethoxysilane, etc. Specific examples of commercially available silyl compounds include KBM403 manufactured by Shin-Etsu Chemical Co., Ltd.

[0286] 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.

[0287] In the reactive composition of the present disclosure, the onium salt compound or polymerization initiator is present in an amount of, for example, approximately 0.001 to 50 parts by mass, preferably 0.01 to 10 parts by mass, relative to 100 parts by mass of the reactive compound. In this specification, numerical ranges expressed with "to" include both the upper and lower limits unless otherwise specified. The reactive compounds may be used alone or in combination of two or more. The reactive composition of the present disclosure may also contain optional components other than the onium salt compound and reactive compound. The optional components are not particularly limited, and examples include solvents for dilution and surfactants. Other optional components include sensitizers, antioxidants, stabilizers, solvents, leveling agents, silane coupling agents, fillers, conductive particles, plasticizers, defoamers, foaming agents, UV absorbers, ion adsorbents, pigments, dyes, fluorescent materials, release agents, antistatic agents, flame retardants, and radical curable compounds.

[0288] 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 ether amide; urea-based solvents such as 1,3-dimethyl-2-imidazolidinone; halogen-based solvents such as dichloromethane, dichloroethane, chloroform, 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- acetate), ester-based solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; "HP4032," "HP4032D," and "HP4032SS" (naphthalene-type epoxy resins) manufactured by DIC Corporation; "828US," "jER828EL," "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; and "jER152" (phenol novolac-type epoxy resin) manufactured by Mitsubishi Chemical Corporation. "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 having an ester skeleton) manufactured by Daicel Corporation; "PB-3600" (epoxy resin having a butadiene structure) manufactured by Daicel Corporation;Examples of suitable solvents include liquid epoxy resins such as "ZX-1658" and "ZX-1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resins) manufactured by Nippon Steel Chemical & Material Co., Ltd. These solvents may be used alone or in combination of two or more in any ratio. Among these, preferred solvents are propylene carbonate, methyl isobutyl ketone, PGMAc (propylene glycol 1-monomethyl ether 2-acetate), toluene, Celloxide 2021P, and jER828.

[0289] <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.

[0290] 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. Such surfactants are preferably, for example, nonionic surfactants containing at least one of a fluorine atom and a silicon atom. Commercially available surfactants that can be used include, for example, the "Megafac" series manufactured by DIC Corporation, including 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. 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).

[0291] 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.

[0292] <Method for 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.

[0293] <Polymer and its manufacturing method> The reactive composition of the present disclosure can be polymerized by a known method 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 an electron beam, and a method of polymerizing using heat. For example, a method of polymerizing using light irradiation can include a photopolymerization step of prepolymerizing (pre-curing) the reactive composition by light irradiation, and a thermal polymerization step of polymerizing the reactive composition 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 by light irradiation and then performing heat treatment.

[0294] In the photoreaction step, the light to be irradiated preferably contains light in the wavelength range of 10 nm to 500 nm, and more preferably contains ultraviolet light with a wavelength of 400 nm or less.

[0295] 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.

[0296] 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:

[0297] The light irradiation time is not particularly limited and is, for example, 0.1 seconds to 3 minutes.

[0298] In the thermal polymerization step, the heating temperature may be 60° C. to 130° C., preferably 70° C. to 120° C., and more preferably 80° C. to 100° C. The heating time is not particularly limited, and may be, for example, 10 minutes to 4 hours.

[0299] The use applications of the onium salt compound, acid generator, polymerization initiator, reactive composition, or polymer according to the present disclosure are not particularly limited, and the compounds 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.

[0300] Examples of applications in electrical and electronic materials include adhesives, encapsulants (semiconductor encapsulants), sealants, insulating materials, thermally conductive materials, hot melt materials, paints, potting agents, etc. More specific examples include encapsulating 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. As optical components, for example, it can be used as an adhesive for 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, projection lenses for projection televisions, etc.

[0301] 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.

[0302] 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.

[0303] Examples of materials for automotive applications include sealing materials, coating materials, cushioning materials, vibration-damping materials, soundproofing materials, spraying materials, etc. for automobile bodies; adhesives, pressure-sensitive adhesives, coating materials, foam materials, etc. for automobile interiors; sealing materials, adhesives, etc. for automobile parts; and sealing materials, adhesives, coating materials for various steel plate joints for trucks, buses, etc.

[0304] Examples of medical material applications include medical rubber materials, medical adhesives, and medical equipment sealing materials.

[0305] Examples and comparative examples of the present disclosure will be specifically described below, although the present disclosure is not limited to these examples.

[0306] <Method of producing onium salt compound>

[0307] Example 1

[0308] The compound (1-1) of Example 1 was produced through the following steps I, II and III.

[0309] 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).

[0310]

[0311] 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.

[0312]

[0313] 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 were placed in a 500 ml four-neck flask and stirred at 25° C. for 2 hours. The organic layer of the obtained reaction solution was separated by a separation operation. The residue obtained 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.

[0314] １ HNMR (400MHz, CD ３ CN) δ7.51 to 7.36 (m, 5H), 4.59 (s, 2H), 4.35 (t, 1H), 3.66 (t, 1H), 3.29 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.12 (s, 2F), -162.30 (t, 1F), -166.72 (t, 2F)

[0315] Example 2

[0316] 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 I of Example 1. The yield of the resulting compound (1-2) was 86%.

[0317] １ HNMR (400MHz, CD ３ CN) δ8.12 (d, 1H), 7.94 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.59 (d, 2H), 7.50 to 7.37 (m, 3H), 4.80 (s, 2H), 4.04 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.15 (s, 2F), -162.32 (t, 1F), -166.74 (t, 2F)

[0318] Example 3

[0319] 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 I of Example 2. The yield of the resulting compound (1-3) was 91%.

[0320] １ HNMR (400MHz, CD ３ CN) 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, CD ３ CN) δ -132.09 (s, 2F), -162.32 (t, 1F), -166.72 (t, 2F)

[0321] Example 4

[0322] 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 I of Example 2. The yield of the resulting compound (1-4) was 82%.

[0323] １ HNMR (400MHz, CD ３ CN) δ8.18 (t, 2H), 8.00 (d, 2H), 7.94 (d, 1H), 7.84 (t, 2H), 7.72 (t, 1H), 7.70 to 7.58 (m, 2H), 7.54 (t, 1H), 5.26 (s, 2H), 4.01 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.10 (s, 2F), -162.32 (t, 1F), -166.73 (t, 2F)

[0324] Example 5

[0325] Example 5 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step I 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%.

[0326] １ HNMR (400MHz, CD ３ CN) δ8.10 (d, 1H), 7.92 (d, 1H), 7.80 (t, 1H), 7.68 (t, 1H), 7.57 (d, 2H), 7.48 to 7.35 (m, 3H), 3.80 (t, 2H), 3.40 (t, 2H), 4.02 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.13 (s, 2F), -162.33 (t, 1F), -166.73 (t, 2F)

[0327] Example 6

[0328] 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 I of Example 2. The yield of the resulting compound (1-6) was 82%.

[0329] １ HNMR (400MHz, CD ３ CN) δ8.16 (d, 1H), 7.95 (d, 1H), 7.83 (t, 1H), 7.72 (t, 1H), 7.40 (d, 1H), 7.1 4 (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, CD ３ CN) δ -132.09 (s, 2F), -162.32 (t, 1F), -166.73 (t, 2F)

[0330] Example 7

[0331] 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 I of Example 2. The yield of the resulting compound (1-7) was 82%.

[0332] １ HNMR (400MHz, CD ３CN) δ8.12 (d, 1H), 7.93 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.34 (s, 1H), 7.2 9 (d, 1H), 7.20 (d, 1H), 4.73 (s, 2H), 4.03 (s, 3H), 2.27 (s, 3H), 2.26 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.15 (s, 2F), -162.33 (t, 1F), -166.75 (t, 2F)

[0333] Example 8

[0334] 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 I of Example 2. The yield of the resulting compound (1-8) was 82%.

[0335] １ HNMR (400MHz, CD ３ CN) δ8.14 (d, 1H), 7.96 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.45 (d, 2H), 7.2 2 (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, CD ３ CN) δ -132.09 (s, 2F), -162.33 (t, 1F), -166.72 (t, 2F)

[0336] Example 9

[0337] 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 III 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%.

[0338] １ HNMR (400MHz, CD ３CN) δ8.14 (d, 1H), 7.95 (d, 1H), 7.82 (t, 1H), 7.73 (s, 8H), 7.70 (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, CD ３ CN) δ-61.91(s)

[0339] Example 10

[0340] 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 III 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%.

[0341] １ HNMR (400MHz, CD ３ CN) δ8.05 (d, 1H), 7.87 (d, 1H), 7.78 (t, 1H), 7.66 (t, 1H), 7.55 (d, 2H), 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, CD ３ CN) δ-122.98 (s)

[0342] Example 11

[0343] 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 III 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%.

[0344] １ HNMR (400MHz, CD ３CN) δ8.11 (d, 1H), 7.93 (d, 1H), 7.81 (t, 1H), 7.69 (t, 1H), 7.59 (d, 2H), 7.50 to 7.39 (m, 3H), 4.79 (s, 2H), 4.03 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -119.01 (s, 2F), -125.47 (s, 1F)

[0345] Example 12

[0346] 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 III 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%.

[0347] １ HNMR (400MHz, CD ３ CN) δ8.12 (d, 1H), 7.94 (d, 1H), 7.81 (t, 1H), 7.70 (t, 1H), 7.59 (d, 2H), 7.50 to 7.39 (m, 3H), 4.79 (s, 2H), 4.03 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ-75.96 (s)

[0348] Example 13

[0349] 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 III 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%.

[0350] １ HNMR (400MHz, CD ３CN) 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, CD ３ CN) δ -119.02 (s, 2F), -125.48 (s, 1F)

[0351] Example 14

[0352] 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 III 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%.

[0353] １ HNMR (400MHz, CD ３ CN) δ8.13 (d, 1H), 7.95 (d, 1H), 7.82 (t, 1H), 7.74 (s, 8H), 7.70 (t, 1H), 7.6 8 (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, CD ３ CN) δ-61.68 (s)

[0354] Example 15

[0355] 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) was replaced with 5.17 g of diethyl sulfate (5-2) in Step II of Example 2. The yield of the resulting compound (1-15) was 78%.

[0356] １ HNMR (400MHz, CD ３CN) δ8.14 (d, 1H), 7.98 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.60 (d, 2H), 7.50 to 7.39 (m, 3H), 4.81 (s, 2H), 4.60 (q, 2H), 1.50 (t, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.11 (s, 2F), -162.33 (t, 1F), -166.74 (t, 2F)

[0357] Example 16

[0358] 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 I of Example 2. The yield of the resulting compound (1-16) was 71%.

[0359] １ HNMR (400MHz, CD ３ CN) 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, CD ３ CN) δ -132.17 (s, 2F), -162.33 (t, 1F), -166.74 (t, 2F)

[0360] Example 17

[0361] 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 I of Example 2. The yield of the resulting compound (1-17) was 70%.

[0362] １ HNMR (400MHz, CD ３ CN) δ8.15 (d, 1H), 7.94 (d, 1H), 7.82 (t, 1H), 7.71 (t, 1H), 4.25 to 4.11 (m, 1H), 4.01 (s, 3H), 2.48 to 2.43 (m, 2H), 1.93 to 1.75 (m, 6H) １９ FNMR (376MHz, CD３ CN) δ -132.11 (s, 2F), -162.32 (t, 1F), -166.73 (t, 2F)

[0363] Example 18

[0364] 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 III 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%.

[0365] １ HNMR (400MHz, CD ３ CN) δ8.15 (d, 1H), 7.94 (d, 1H), 7.82 (t, 1H), 7.71 (t, 1H), 4.23 to 4.13 (m, 1H), 4.00 (s, 3H), 2.51 to 2.38 (m, 2H), 1.94 to 1.75 (m, 6H) １９ FNMR (376MHz, CD ３ CN) δ -119.01 (s, 2F), -125.46 (s, 1F)

[0366] Example 19

[0367] 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 III 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%.

[0368] １ HNMR (400MHz, CD ３ CN) δ8.15 (d, 1H), 7.95 (d, 1H), 7.83 (t, 1H), 7.73 to 7.68 (m, 13H), 4.24 to 4.14 (m, 1H), 4.02 (s, 3H), 2.51 to 2.37 (m, 2H), 1.92 to 1.74 (m, 6H) １９ FNMR (376MHz, CD ３CN) δ-61.67 (s)

[0369] Example 20

[0370] Example 20 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step III of Example 2 was replaced with 2.55 g of allyl chloride (3-10). The yield of the resulting compound (1-20) was 79%.

[0371] １ HNMR (400MHz, CD ３ CN) δ8.15 (d, 1H), 7.96 (d, 1H), 7.83 (t, 1H), 7.71 (t, 1H), 6.08 to 5.98 (m, 1H), 5.66 (d, 1H), 5.49 (d, 1H), 4.23 (d, 2H), 4.06 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.16 (s, 2F), -162.32 (t, 1F), -166.72 (t, 2F)

[0372] Example 21

[0373] 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 III of Example 2. The yield of the resulting compound (1-21) was 75%.

[0374] １ HNMR (400MHz, CD ３ CN) 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) １９ FNMR (376MHz, CD ３ CN) δ -132.13 (s, 2F), -162.32 (t, 1F), -166.73 (t, 2F)

[0375] Example 22

[0376] 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 III 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%.

[0377] １ HNMR (400MHz, CD ３ CN) 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, CD ３ CN) δ -119.01 (s, 2F), -125.47 (s, 1F)

[0378] Example 23

[0379] 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 III 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%.

[0380] １ HNMR (400MHz, CD ３ CN) δ8.15 (d, 1H), 7.95 (d, 1H), 7.82 (t, 1H), 7.78 to 7.61 (m, 13H), 7.50 (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, CD ３ CN) δ-61.68 (s)

[0381] Example 24

[0382] Example 24 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step I 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%.

[0383] １ HNMR (400MHz, CD ３ CN) δ8.14 (d, 1H), 7.96 (d, 1H), 7.83 (t, 1H), 7.72 (t, 1H), 6.04 to 5.97 (m, 1 H), 5.62 (d, 1H), 5.43 (d, 1H), 4.61 to 4.49 (m, 1H), 4.05 (s, 3H), 1.72 (d, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.04 (s, 2F), -162.32 (t, 1F), -166.71 (t, 2F)

[0384] Example 25

[0385] 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 III 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%.

[0386] １ HNMR (400MHz, CD ３ CN) δ8.14 (d, 1H), 7.95 (d, 1H), 7.82 (t, 2H), 7.71 (t, 2H), 6.05 to 5.99 (m, 1 H), 5.63 (d, 1H), 5.44 (d, 1H), 4.57 to 4.53 (m, 1H), 4.04 (s, 3H), 1.72 (d, 3H) １９ FNMR (376MHz, CD ３ CN) δ -119.01 (s, 2F), -125.47 (s, 1F)

[0387] Example 26

[0388] 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 III 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%.

[0389] １ HNMR (400MHz, CD ３ CN) δ8.15 (d, 1H), 7.96 (d, 1H), 7.83 (t, 1H), 7.76 to 7.66 (m, 13H), 6.05 to 5.98 ( m, 1H), 5.63 (d, 1H), 5.44 (d, 1H), 4.58 to 4.54 (m, 1H), 4.05 (s, 3H), 1.72 (d, 3H) １９ FNMR (376MHz, CD ３ CN) δ-61.67 (s)

[0390] Example 27

[0391] Example 27 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step I 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%.

[0392] １ HNMR (400MHz, CD ３ CN) 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, CD ３ CN) δ -132.05 (s, 2F), -162.33 (t, 1F), -166.72 (t, 2F)

[0393] Example 28

[0394] 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 I of Example 2. The yield of the resulting compound (1-28) was 59%.

[0395] １ HNMR (400MHz, CD ３ CN) δ8.16 (d, 1H), 7.95 (d, 1H), 7.83 (t, 1H), 7.71 (t, 1H), 7.69 to 7.55 (m, 2H), 7.43 to 7.35 (m, 2H), 7.28 (d, 1H), 4.04 (s, 2H), 3.04 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.18 (s, 2F), -162.37 (t, 1F), -166.80 (t, 2F)

[0396] Example 29

[0397] 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 I of Example 2. The yield of the resulting compound (1-29) was 75%.

[0398] １ HNMR (400MHz, CD ３ CN) δ8.21 (d, 1H), 8.02 (d, 1H), 7.89 (t, 1H), 7.78 (t, 1H), 7.59 to 7.49 (m, 5H), 5.10 (d, 1H), 4.04 (s, 3H), 3.64 (d, 1H), 3.13 (m, 1H) １９ FNMR (376MHz, CD ３ CN) δ -132.10 (s, 2F), -162.33 (t, 1F), -166.75 (t, 2F)

[0399] Example 30

[0400] Example 30 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step I of Example 2 was replaced with 3.56 g of 1-chloropentane (3-16). The yield of the resulting compound (1-30) was 90%.

[0401] １ HNMR (400MHz, CD ３ CN) δ8.15 (d, 1H), 7.95 (d, 1H), 7.83 (t, 1H), 7.70 (t, 1H), 4.04 (s, 3H), 3.54 ( t, 2H), 2.02 to 1.91 (m, 2H), 1.61 to 1.47 (m, 2H), 1.45 to 1.38 (m, 2H), 0.94 (t, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.07 (s, 2F), -162.32 (t, 1F), -166.71 (t, 2F)

[0402] Example 31

[0403] Example 31 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step I 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%.

[0404] １ HNMR (400MHz, CD ３ CN) δ8.30 (d, 1H), 8.12 (d, 1H), 7.94 (t, 1H), 7.83 (t, 1H), 7.53 to 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, CD ３ CN) δ -132.13 (s, 2F), -162.34 (t, 1F), -166.76 (t, 2F)

[0405] Example 32

[0406] 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 I of Example 2. The yield of the resulting compound (1-32) was 87%.

[0407] １ HNMR (400MHz, CD ３ CN) δ 7.95 to 7.92 (m, 1H), 7.62 to 7.51 (m, 4H), 7.49 to 7.39 (m, 3H), 4.78 (s, 2H), 4.28 (s, 3H), 2.87 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.13 (s, 2F), -162.32 (t, 1F), -166.73 (t, 2F)

[0408] Example 33

[0409] Example 33 was synthesized in the same manner as in Example 2, except that 3.89 g of 3-chlorocyclohexene (3-18) was used instead of benzyl chloride (3-1) in Step I of Example 2. The yield of the resulting compound (1-33) was 67%.

[0410] １ HNMR (400MHz, CD ３ CN) δ8.15 (d, 1H), 7.97 (d, 1H), 7.85 (t, 1H), 7.72 (t, 1H), 5.99 to 5.93 (m, 1H), 5.5 2 (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, CD ３ CN) δ -132.03 (s, 2F), -162.33 (t, 1F), -166.71 (t, 2F)

[0411] Comparative Example 1: Compound described in Patent Document 6 (JP-A-07-025863)

[0412] 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 III of Example 2 was replaced with 8.66 g of sodium hexafluoroantimonate. The yield of the comparative product compound (a1) was 82%.

[0413] １ HNMR (400MHz, CD ３CN) δ8.12 (d, 1H), 7.94 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.59 (d, 2H), 7.50 to 7.40 (m, 3H), 4.79 (s, 2H), 4.03 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -109.35 to -135.11 (m)

[0414] Comparative Example 2: Compound described in Patent Document 6 (JP-A-07-025863)

[0415] 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 III of Example 2 was replaced with 3.67 g of sodium tetrafluoroborate. The yield of the comparative product compound (a2) was 89%.

[0416] １ HNMR (400MHz, CD ３ CN) δ8.13 (d, 1H), 7.95 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.60 (dd, 2H), 7.50 to 7.40 (m, 3H), 4.80 (s, 2H), 4.04 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ-150.12(s)

[0417] Comparative Example 3: Compound described in Patent Document 6 (JP-A-07-025863)

[0418] 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 III of Example 2 was replaced with 5.61 g of sodium hexafluorophosphate. The yield of the comparative product compound (a3) ​​was 90%.

[0419] １ HNMR (400MHz, CD ３CN) δ8.12 (d, 1H), 7.94 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.59 (d, 2H), 7.50 to 7.40 (m, 3H), 4.79 (s, 2H), 4.03 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ-72.20(s)

[0420] Comparative Example 4

[0421] 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 III of Example 2 was replaced with 5.75 g of sodium triflate. The yield of the comparative product compound (a4) was 88%.

[0422] １ HNMR (400MHz, CD ３ CN) δ8.14 (d, 1H), 7.97 (d, 2H), 7.82 (t, 1H), 7.70 (t, 1H), 7.60 (dd, 2H), 7.50 to 7.39 (m, 3H), 4.80 (s, 2H), 4.04 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ-77.67 (s)

[0423] Comparative Example 5

[0424] 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 III of Example 2 was replaced with 11.43 g of sodium tetraphenylborate. The yield of the comparative product compound (a5) was 90%.

[0425] １ HNMR (400MHz, CD ３ CN) δ 7.97 (d, 1H), 7.82 to 7.70 (m, 2H), 7.63 (t, 1H), 7.53 (d, 2H), 7.47 to 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)

[0426] Comparative Example 6

[0427] 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 III of Example 2 was replaced with 9.59 g of lithium bis(trifluoromethanesulfonyl)imide. The yield of the comparative product compound (a6) was 84%.

[0428] １ HNMR (400MHz, CD ３ CN) δ8.12 (d, 1H), 7.94 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.59 (d, 2H), 7.50 to 7.39 (m, 3H), 4.79 (s, 2H), 4.04 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ-78.59(s)

[0429] Evaluation Test of Onium Salt Compounds <Solvent Compatibility> 1 g of each of the onium salt compounds of Examples 1 to 33 or the onium salt compounds of Comparative Examples 1 to 6 was placed in a 30 mL screw tube at 25° C. Next, 1 g of each solvent was added to the 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.

[0430] 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: 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>".

[0431] Solvent compatibility was evaluated by counting the number of solvents with a solubility of 1% or more among the solvents measured this time and assigning a score as follows: 5: Six or more solvents with a solubility of 1% or more 4: Five solvents with a solubility of 1% or more 3: Four solvents with a solubility of 1% or more 2: Three solvents with a solubility of 1% or more 1: Two solvents with a solubility of 1% or more 0: One solvent with a solubility of 1% or more

[0432] The six solvents selected were: Propylene carbonate, methyl isobutyl ketone, PGMAc (propylene glycol 1-monomethyl ether 2-acetate), toluene, Celloxide (registered trademark) 2021P, and jER (registered trademark) 828.

[0433] 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 ), the SP value of MIBK is 8.3 (MPa １ / ２ ), the SP value of toluene is 8.9 (MPa １ / ２ )

[0434] The CELLOXIDE 2021P is 3,4-epoxycyclohexylmethyl (3,4-epoxy) cyclohexane carboxylate.

[0435] The jER828 is a so-called bisphenol A type epoxy resin produced by a condensation reaction between bisphenol A and epichlorohydrin.

[0436] <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 1 minute, and the number of days until gelation occurred, at which point the liquid no longer flowed out, was measured.

[0437] (5-point scale) 5: The solution has stopped flowing for 40 days or more. 4: The solution has stopped flowing for 30 to 39 days. 3: The solution has stopped flowing for 20 to 29 days. 2: The solution has stopped flowing for 10 to 19 days. 1: The solution has stopped flowing for less than 9 days.

[0438] Evaluation Tests of Reactive Compositions Containing Onium Salt Compounds The reactive compositions of the present disclosure were prepared based on the following manufacturing methods. These reactive compositions were evaluated for their photoreactivity and thermal reactivity as described below.

[0439] <Reactive Composition Production Example 1> To each 10 mL light-shielding screw tube, 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-hydroxyphenyl)dimethylsulfonium triflate (manufactured by Sanshin Chemical Industry Co., Ltd., product name: DSP-Tf) as a polymerization inhibitor were added. 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 (product name, manufactured by Daicel Corporation) as a reactive compound was added to each container, and the mixture was immediately mixed in a planetary centrifugal mixer "ARE-310" to prepare a reactive composition.

[0440] <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) Measuring instrument: Differential scanning calorimeter (DSC600, manufactured by Hitachi High-Tech Corporation) Atmosphere: Nitrogen gas, 50 mL / min. Lamp: LA-410UV, mercury xenon lamp Sample amount: 1 mg Illuminance: 20 mW / cm ２ (313 nm) Measurement temperature: 25°C Total calorific value (J / g): Sum of the calorific values ​​(W / g) generated during light irradiation

[0441] (Evaluation) Photoreactivity was evaluated according to the following two-level scale: A: total calorific value of 1 J / g or more B: total calorific value of less than 1 J / g The results are shown in Table 1.

[0442] <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) Measuring equipment: Differential scanning calorimetry (X-DSC7000, manufactured by Hitachi High-Tech Corporation) Atmosphere: Nitrogen gas, 40 mL / min. Sample amount: 5 mg Temperature conditions: 30 to 310°C, 10°C / min. Reaction temperature (°C): The temperature at the apex of the exothermic peak that appears on the lowest temperature side of the exothermic peaks

[0443] (Evaluation) The thermal reactivity was evaluated according to the following two-level scale: A: Reaction temperature was less than 200° C. B: Reaction temperature was 200° C. or more The results are shown in Table 1.

[0444] <Reactive Composition Production Example 2> 20.0 mg of each of the onium salt compounds of Examples 1 to 33 or the onium salt compounds of Comparative Examples 1 to 6 was added to each 10 mL light-shielding screw tube. Next, 20.0 mg of propylene carbonate was added to each container as a solvent. The above 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 each container as a reactive compound, and the mixture was immediately mixed using a planetary centrifugal mixer "ARE-310" to prepare a reactive composition.

[0445] <Photoreactivity (2)> The prepared reactive composition was subjected to UV-DSC measurement to measure the gross calorific value under continuous light irradiation. Note that a larger gross calorific value indicates higher photoreactivity. (Conditions) Measuring instrument: Differential scanning calorimeter (DSC600, manufactured by Hitachi High-Tech Corporation) Atmosphere: Nitrogen gas, 50 mL / min. Lamp: LA-410UV, mercury xenon lamp Sample amount: 1 mg Illuminance: 20 mW / cm ２ (313 nm) Measurement temperature: 25°C Total calorific value (J / g): Sum of the calorific values ​​(W / g) generated during light irradiation

[0446] (Evaluation) Photoreactivity was evaluated according to the following two-level scale: A: total calorific value of 150 J / g or more B: total calorific value of less than 150 J / g The results are shown in Table 1.

[0447]

[0448] <Results> The onium salt compounds of Examples 1 to 33 exhibited excellent solvent compatibility and excellent storage stability. On the other hand, the onium salt compounds of Comparative Examples 1 to 6 exhibited poor results in at least one of solvent compatibility and storage stability. Furthermore, it was found that reactive compositions containing the onium salt compounds of Examples 1 to 33 exhibited excellent photoreactivity and thermal reactivity. Therefore, it was found that reactive compositions containing the onium salt compounds of the present disclosure possess photoreactivity and thermal reactivity and can therefore be used as dual-type acid generators.

[0449] 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.

[0450]

[0451]

[0452]

[0453] Here, the onium salt compound of Example 71 (Compound No. 1-71 in which X is a gallium anion containing a fluorine-containing aromatic ring) and the onium salt compound of Example 72 (Compound No. 1-72 in which X is a phosphorus anion containing a fluorine-containing alkyl group) shown in Table 2 above were produced. Example 71

[0454] Example 71 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 III of Example 2 was replaced with 22.34 g of tetrakis(pentafluorophenyl)gallate lithium salt (7-7). The yield of the resulting compound (1-71) was 60%.

[0455] １ HNMR (400MHz, CD ３CN) δ8.10 (d, 1H), 7.92 (d, 1H), 7.80 (t, 1H), 7.68 (t, 1H), 7.57 (d, 2H), 7.48 to 7.35 (m, 3H), 4.78 (s, 2H), 4.02 (s, 3H)

[0456] Example 72

[0457] Example 72 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 III of Example 2 was replaced with 13.55 g of tris(pentafluoroethyl)trifluorophosphate lithium salt (7-6). The yield of the resulting compound (1-72) was 79%.

[0458] １ HNMR (400MHz, CD ３ CN) δ8.11 (d, 1H), 7.93 (d, 1H), 7.81 (t, 1H), 7.69 (t, 1H), 7.58 (d, 2H), 7.51 to 7.36 (m, 3H), 4.78 (s, 2H), 4.03 (s, 3H) １９ FNMR (376MHz, DMSO-d6) δ -116.14 (m, 4F), -115.32 (m, 2F), -87.34 (m, 2F), -81.24 (m, 6F), -79.54 (m, 3F), -44.04 (m, 1F)

[0459] Next, the onium salt compounds of Examples 73 to 82 below (Compound Nos. 1-73 to 1-82) were prepared.

[0460] Example 73

[0461] Example 73 was synthesized in the same manner as in Example 2, except that 4.77 g of 4-fluorobenzyl chloride (3-22) was used instead of benzyl chloride (3-1) in Step I of Example 2. The yield of the resulting compound (1-73) was 80%.

[0462] １ HNMR (400MHz, CD ３CN) δ8.12 (d, 1H), 7.94 (d, 1H), 7.82 (t, 1H), 7.70 (t, 1H), 7.34 (m, 2H), 7.18 (t, 2H), 4.80 (s, 2H), 4.04 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -112.24 (s, 1F), -132.14 (s, 8F), -162.32 (t, 8F), -166.74 (t, 8F)

[0463] Example 74

[0464] Example 74 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step I of Example 2 was replaced with 4.39 g of 2-butynyl bromide (3-19). The yield of the resulting compound (1-74) was 81%.

[0465] １ HNMR (400MHz, CD ３ CN) δ8.22 (d, 1H), 7.94 (d, 1H), 7.84 (t, 1H), 7.74 (t, 1H), 4.35 (s, 2H), 4.08 (s, 3H), 1.84 (t, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.15 (s, 2F), -162.30 (t, 1F), -166.74 (t, 2F)

[0466] Example 75

[0467] Example 75 was synthesized in the same manner as in Example 2, except that 4.39 g of 3-butynyl bromide (3-20) was used instead of benzyl chloride (3-1) in Step I of Example 2. The yield of the resulting compound (1-75) was 84%.

[0468] １ HNMR (400MHz, CD ３ CN) δ8.20 (d, 1H), 7.95 (d, 1H), 7.83 (t, 1H), 7.73 (t, 1H), 4.07 (s, 3H), 3.71 (t, 2H), 2.89 (m, 2H), 2.45 (t, 1H) １９ FNMR (376MHz, CD ３CN) δ -132.16 (s, 2F), -162.32 (t, 1F), -166.74 (t, 2F)

[0469] Example 76

[0470] Example 76 was synthesized in the same manner as in Example 1, except that benzyl chloride (3-1) in Step I was replaced with 4.16 g of dimethyl sulfate (3-21) and dimethyl sulfate (5-1) in Step II was replaced with 2.52 g of allyl chloride (5-3). The yield of the resulting compound (1-76) was 81%.

[0471] １ HNMR (400MHz, CD ３ CN) δ5.88 (m, 1H), 5.43 (m, 2H), 4.43 (t, 2H), 4.33 (d, 2H), 3.71 (t, 2H), 2.82 (s, 3H), １９ FNMR (376MHz, CD ３ CN) δ -132.12 (s, 2F), -162.30 (t, 1F), -166.72 (t, 2F)

[0472] Example 77

[0473] Example 77 was synthesized in the same manner as in Example 1, except that benzyl chloride (3-1) in Step I was replaced with 4.16 g of dimethyl sulfate (3-21), and dimethyl sulfate (5-1) in Step II was replaced with 6.47 g of cyclopentyl iodide (5-4). The yield of the resulting compound (1-77) was 78%.

[0474] １ HNMR (400MHz, CD ３ CN) δ 4.43 (t, 2H), 4.23 (m, 1H) 3.71 (t, 2H), 2.82 (s, 3H), 1.92 (m, 8H) １９ FNMR (376MHz, CD ３ CN) δ -132.11 (s, 2F), -162.30 (t, 1F), -166.72 (t, 2F)

[0475] Example 78

[0476] Example 78 was synthesized in the same manner as in Example 3, except that dimethyl sulfate (5-1) in Step II of Example 3 was replaced with 6.47 g of cyclopentyl iodide (5-4). The yield of the resulting compound (1-78) was 73%.

[0477] １ HNMR (400MHz, CD ３ CN) δ8.22 (d, 1H), 7.95 (d, 1H), 7.78 (t, 1H), 7.71 (t, 1H), 7.21 (s, 4H), 5.72 (s, 2H), 4.23 (m, 1H), 2.32 (s, 3H), 1.90 (m, 8H) １９ FNMR (376MHz, CD ３ CN) δ -132.15 (s, 2F), -162.32 (t, 1F), -166.74 (t, 2F)

[0478] Example 79

[0479] Example 79 was synthesized in the same manner as in Example 2, except that dimethyl sulfate (5-1) in Step II of Example 2 was replaced with 6.23 g of 4-fluorobenzyl bromide (5-5). The yield of the resulting compound (1-79) was 75%.

[0480] １ HNMR (400MHz, CD ３ CN) δ8.22 (d, 1H), 7.94 (d, 1H), 7.78 (t, 1H), 7.73 (t, 1H), 7.58 (d, 2H), 7.45 (d, 2H), 7.35 (m, 3H), 7.17 (t, 2H), 5.71 (s, 2H), 4.81 (s, 2H) １９ FNMR (376MHz, CD ３ CN) δ -112.23 (s, 1F), -132.15 (s, 2F), -162.33 (t, 1F), -166.74 (t, 2F)

[0481] Example 80

[0482] Example 80 was synthesized in the same manner as in Example 3, except that dimethyl sulfate (5-1) in Step II of Example 3 was replaced with 6.23 g of 4-fluorobenzyl bromide (5-5). The yield of the resulting compound (1-80) was 71%.

[0483] １ HNMR (400MHz, CD ３ CN) δ8.22 (d, 1H), 7.94 (d, 1H), 7.78 (t, 1H), 7.73 (t, 1H), 7.58 (d, 2H), 7.45 (d, 2H), 7.21 (s, 4H), 5.71 (s, 2H), 4.81 (s, 2H), 2.33 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -112.25 (s, 1F), -132.09 (s, 2F), -162.32 (t, 1F), -166.72 (t, 2F)

[0484] Example 81

[0485] Example 81 was synthesized in the same manner as in Example 17, except that dimethyl sulfate (5-1) in Step II of Example 17 was replaced with 7.39 g of 3,3,3-trifluoropropyl iodide (5-6). The yield of the resulting compound (1-81) was 69%.

[0486] １ HNMR (400MHz, CD ３ CN) δ8.20 (d, 1H), 7.97 (d, 1H), 7.85 (t, 1H), 7.74 (t, 1H), 4.78 (t, 2H), 4.24 (m, 1H), 2.90 (m, 2H), 1.90 (m, 8H) １９ FNMR (376MHz, CD ３ CN) δ -64.04 (s, 3F), -132.15 (s, 8F), -162.31 (t, 4F), -166.74 (t, 8F)

[0487] Example 82

[0488] Example 82 was synthesized in the same manner as in Example 2, except that benzyl chloride (3-1) in Step I was replaced with 4.16 g of dimethyl sulfate (3-21) and dimethyl sulfate (5-1) in Step II was replaced with 4.42 g of 3-bromopropionitrile (5-7). The yield of the resulting compound (1-82) was 69%.

[0489] １ HNMR (400MHz, CD ３ CN) δ8.21 (d, 1H), 8.06 (d, 1H), 7.84 (t, 1H), 7.74 (t, 1H), 4.81 (t, 2H), 3.11 (t, 2H), 3.08 (s, 3H) １９ FNMR (376MHz, CD ３ CN) δ -132.16 (s, 2F), -162.32 (t, 1F), -166.74 (t, 2F)

[0490] The onium salt compounds obtained in Examples 71 to 82 were evaluated for solvent compatibility, storage stability, photoreactivity (1), thermal reactivity (1), and photoreactivity (2) in accordance with the procedures described in the above Test Examples. The results are shown in Table 5.

[0491]

[0492] Results From the results in Table 5 above, it was found that the onium salt compounds of Examples 71 to 82 had excellent solvent compatibility and excellent storage stability.

[0493] 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 both 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, being photoreactive, can function not only as an acid generator but also as a radical generator. Therefore, the onium salt compound of the present disclosure can be used in a variety of applications, such as adhesives, sealants, and resists.

[0494] This application claims priority from Japanese Patent Application No. 2024-154279, filed September 6, 2024. Japanese Patent Application No. 2024-154279 is incorporated herein by reference.

Claims

1. General formula (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. ４ 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, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic oxycarbonyl group, an optionally substituted 3-15-membered saturated or unsaturated carbocyclic oxycarbonyl group, an optionally substituted aminocarbonyl group, or a carboxyl group. ５ and R ６ 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 3-15 membered saturated or unsaturated carbocyclic group, an optionally substituted C1-15 alkoxy group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxy group, an optionally substituted C1-15 alkylcarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, represents an oxycarbonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, an aminocarbonyl group which may have a substituent, a carboxyl group, an amino group which may have a substituent, a C1-15 alkylthio group which may have a substituent, a thio group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfinyl group which may have a substituent, a sulfinyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, a C1-15 alkylsulfonyl group which may have a substituent, a sulfonyl group having an optionally substituted 3- to 15-membered saturated or unsaturated carbocyclic ring, or a heterocyclic group which may have a substituent; 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 bond or a double bond. 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.

2. The above R Ａ is represented by the following general formula (1-R Ａ ): (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, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic carbonyl group, an optionally substituted C1-15 alkoxycarbonyl group, an optionally substituted 3-15 membered saturated or unsaturated carbocyclic oxycarbonyl group R represents 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, an optionally substituted C1-15 alkylsulfinyl group, a sulfinyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfonyl group, a sulfonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted heterocyclic group, or an optionally substituted silyl group. 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. 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; or 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 ring or a heterocyclic ring. The saturated or unsaturated carbocyclic ring or the heterocyclic ring may further have a substituent. * indicates the bonding position to the sulfur atom in the general formula (1). The onium salt compound according to claim 1, wherein the group is a group represented by the following formula:

3. The above 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 an aminocarbonyl group, a carboxyl group, an optionally substituted C1-15 alkylthio group, an optionally substituted thio group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfinyl group, an optionally substituted sulfinyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted C1-15 alkylsulfonyl group, an optionally substituted sulfonyl group having a 3-15-membered saturated or unsaturated carbocyclic ring, an optionally substituted heterocyclic group, or an optionally substituted silyl group; ２ is a hydrogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group; ３ is a hydrogen atom, an optionally substituted C1-15 alkyl group, or an optionally substituted 3-15 membered saturated or unsaturated carbocyclic group; or １ , R ２ and R ３ The onium salt compound according to claim 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.

4. The above X － is represented by the general formula (XA1): － B (R Ｘ１ ) a(R Ｘ２ ) b (wherein R Ｘ１ is a fluorine atom or C ｎ F ２ｎ＋１ R represents a group. Ｘ２ represents 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 (provided that the above-mentioned R Ｘ２ When is an unsubstituted phenyl group, a represents an integer of 1 to 3; general formula (XB1): － Ga(R Ｘ３ ) a(R Ｘ４ ) b (wherein R Ｘ３ is a fluorine atom or C ｎ F ２ｎ＋１ R represents a group. Ｘ４ represents 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;); General formula (XC1): － C (R Ｘ５ ) (R Ｘ６ ) (R Ｘ７ ) (wherein R Ｘ５ , R Ｘ６ and R Ｘ７ are the same or different, and 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; General formula (XD1): (wherein r represents an integer of 1 to 6); or a cyclic sulfonimide anion having a fluorine atom represented by the following general formula (XE1): P(RX ８ ) c (RX ９ ) d) a phosphorus anion containing a fluorine-containing alkyl group (wherein R X ８ is CuF ２ｕ＋１ represents the 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 an integer of 0 to 5. c+d represents 6. The onium salt compound according to claim 1, wherein 5. The above X － is represented by the following general formula (XA2): (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 Any 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; General formula (XB2): (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 Any one of the following is a fluorine atom or C ｎ F ２ｎ＋１ a gallium anion represented by the following general formula (XC2): (In the formula, R ４０ , R ４１ and R ４２ are the same or different, and C ｔ F ２ｔ＋１ a group; and t represents an integer of 1 to 15; General formula (XD1): (wherein r represents an integer of 1 to 6); or a cyclic sulfonimide anion having a fluorine atom represented by the following general formula (XE1): P(RX ８ ) c (RX ９ ) d) a phosphorus anion containing a fluorine-containing alkyl group (wherein R X ８ is CuF ２ｕ＋１ represents the 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 an integer of 0 to 5. c+d represents 6. The onium salt compound according to claim 1, wherein 6. The above 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.

7. The above R ４ The onium salt compound according to claim 1, wherein is a C1-15 alkyl group which may have a substituent.

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

9. A polymerization initiator containing the onium salt compound according to any one of claims 1 to 7.

10. A reactive composition containing the onium salt compound according to any one of claims 1 to 7 and a reactive compound.

11. A polymer obtained from the reactive composition of claim 10.

12. An adhesive, sealant, or resist containing the reactive composition according to claim 10.

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