Salt, acid generator, resist composition, and method for producing resist pattern

Abstract

To provide a salt which allows a resist pattern having good line edge roughness to be produced, an acid generator, and a resist composition containing the same.SOLUTION: There are provided a salt represented by formula (I), an acid generator, and a resist composition containing the same. [In the formula, R1-R3 each represent a hydrogen atom, a halogen atom or the like; W1-W3 each represent an alicyclic hydrocarbon group, provided that -CH2- in the group may be substituted with -O-, -CO- or the like; and AI- represents an organic anion.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to salts, acid generators, resist compositions, and methods for producing resist patterns. [Background technology]

[0002] Patent Document 1 describes a salt represented by the following formula, and a resist composition containing the salt as an acid generator. Patent document 2 (TIFF2023156258000001.tif2672) describes a salt represented by the following formula, and a resist composition containing the salt as an acid generator. TIFF2023156258000002.tif2692 [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2010-140014 [Patent Document 2] Japanese Patent Publication No. 2011-006399 [Overview of the project] [Problems that the invention aims to solve]

[0004] The present invention aims to provide a salt that forms a resist pattern with better line edge roughness (LER) than a resist pattern formed from a resist composition containing the above-mentioned salt. [Means for solving the problem]

[0005] This invention includes the following inventions. [1] An acid generator containing a salt represented by formula (I). TIFF2023156258000003.tif62150[In formula (I), R 1 , R 2 and R 3Each independently represents a hydrogen atom, a halogen atom, or a haloalkyl group having 1 to 12 carbon atoms. However, R 1 R 2 and R 3 At least one of is a halogen atom or a haloalkyl group having 1 to 12 carbon atoms. The -CH2- contained in the haloalkyl group may be replaced by -O-, -S-, -CO-, or -SO2-. R 4 R 5 R 6 R 7 R 8 and R 9 Each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 36 carbon atoms. The hydrocarbon group may have a substituent, and the -CH2- contained in the haloalkyl group and the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-. A 1 A 2 and A 3 Each independently represents a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon group may have a substituent, and the -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S-, or -SO2-. W 1 W 2 and W 3 Each independently represents an alicyclic hydrocarbon group having 3 to 28 carbon atoms. The -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S-, or -SO2-. m1 represents any integer from 1 to 5. When m1 is 2 or more, the groups within multiple parentheses may be the same as or different from each other. m2 represents any integer from 0 to 5. When m2 is 2 or more, the groups within multiple parentheses may be the same as or different from each other. m3 represents any integer from 0 to 5. When m3 is 2 or more, the groups within multiple parentheses may be the same as or different from each other. m4 represents any integer from 0 to 13. When m4 is 2 or more, the multiple R 4 may be the same as or different from each other. m5 represents an integer between 0 and 13, and when m5 is 2 or greater, multiple R 5 They may be identical or different from one another. m6 represents an integer between 0 and 13, and when m6 is 2 or greater, multiple R 6 They may be identical or different from one another. m7 represents an integer between 0 and 4, and when m7 is 2 or greater, multiple R 7 They may be identical or different from one another. m8 represents an integer between 0 and 5, and when m8 is 2 or greater, multiple R 8 They may be identical or different from one another. m9 represents an integer between 0 and 5, and when m9 is 2 or greater, multiple R 9 They may be identical or different from one another. However, 1 ≤ m1 + m7 ≤ 5, 0 ≤ m2 + m8 ≤ 5, and 0 ≤ m3 + m9 ≤ 5. AI - This represents an organic anion. [2]A 1 However, ***-X 01 -L 01 - or ***-L 01 -X 01 -and, A 2 However, ***-X 02 -L 02 - or ***-L 02 -X 02 -and, A 3 However, ***-X 03 -L 03 - or ***-L 03 -X 03 -and, X 01 , X 02 and X 03 These each independently represent -O-, -CO-, -S-, or -SO2-, L 01 , L 02 and L 03Each of these independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S-, or -SO2-). *** is A 1 , A 2 Or A 3 An acid generator as described in [1], representing a bonding site with a benzene ring to which it can be bonded. [3]X 01 , X 02 and X 03 The acid generator described in [2] is independently -O- or -S-. [4]L 01 , L 02 and L 03 The acid generator according to [2] or [3], wherein each is independently a single bond or an alkanediyl group having 1 to 6 carbon atoms (the -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-). [5] AI - The acid generator is one of the following [1] to [4], wherein the anion is a sulfonate anion, a sulfonylimide anion, or a sulfonylmethide anion. [6] AI - The acid generator described in any of [1] to [5] is a sulfonate anion, and the sulfonate anion is an anion represented by formula (IA) or formula (IB). TIFF2023156258000004.tif2965[In formula (IA), Q 1 and Q 2 Each of these independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L 1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and the -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. Y 1This represents a methyl group which may have substituents or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-. TIFF2023156258000005.tif3182[In formula (IB), m21 represents an integer between 1 and 5, and when m21 is 2 or greater, the bases within the parentheses may be the same or different. R 21 This represents a hydrocarbon group having 3 to 48 carbon atoms, including a cyclic hydrocarbon group having 3 to 18 carbon atoms, and the cyclic hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-. R 22 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and the -CH2- contained in the alkyl group may be replaced with -O- or -CO-. m22 represents an integer between 0 and 4, and when m22 is 2 or greater, multiple R 22 They may be identical or different from one another. A resist composition containing an acid generator as described in any of [7][1] to [6]. [8] The resist composition according to [7], further comprising a resin containing a structural unit having an acid-unstable group, wherein the structural unit having an acid-unstable group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), and a structural unit represented by formula (a1-2). TIFF2023156258000006.tif44143[In formulas (a1-0), (a1-1), and (a1-2), L a01 , L a1 and L a2 These are, independently, -O- or *-O-(CH2) k1 -CO-O- represents a bond, where k1 is an integer from 1 to 7, and * represents the bond site with -CO-. R a01 , R a4 and R a5Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. R a02 , R a03 and R a04 Each of these independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. R a6 and R a7 Each of these independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by a combination of these. m1' represents an integer between 0 and 14. n1 represents an integer between 0 and 10. n1' represents an integer between 0 and 3. [9] The resist composition according to [7] or [8], further comprising a resin containing a structural unit having an acid-unstable group, wherein the resin containing the structural unit having an acid-unstable group comprises a structural unit represented by formula (a2-A). TIFF2023156258000007.tif4654[In formula (a2-A), R a50 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. R a51 This represents a halogen atom, a hydroxyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C2-C12 alkoxyalkyl group, a C2-C12 alkoxyalkoxy group, a C2-C4 alkylcarbonyl group, a C2-C4 alkylcarbonyloxy group, an acryloyloxy group, or a methacryloyloxy group. A a50 This is a single bond or *-X a51 -( A a52 -X a52 ) nb - represents -R a50 This represents the bonding site with the carbon atom to which it is bonded. A a52represents an alkanediyl group having 1 to 8 carbon atoms. X a51 and X a52 each independently represent -O-, -CO-O- or -O-CO-. nb represents 0 or 1. mb represents any integer from 0 to 4. When mb is any integer of 2 or more, a plurality of R a51 may be the same as or different from each other. The resist composition according to any one of [7] to [9], further containing a salt that generates an acid having a lower acidity than the acid generated from the salt represented by formula (I).

[11] (1) A step of applying the resist composition according to any one of [7] to

[10] onto a substrate, (2) A step of drying the applied composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the exposed composition layer, and (5) A step of developing the heated composition layer, A method for producing a resist pattern including

[12] The salt represented by the above formula (I).

[13] A 1 is ***-X 01 -L 01 - or ***-L 01 -X 01 -, and A 2 is ***-X 02 -L 02 - or ***-L 02 -X 02 -, and A 3 is ***-X 03 -L 03 - or ***-L 03 -X 03 -, and X 01 、X 02 and X 03 each independently represent -O-, -CO-, -S- or -SO2-, L 01 、L02 and L 03 Each of these independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S-, or -SO2-). *** is A 1 , A 2 Or A 3 The salt described in

[12] represents a bonding site with a benzene ring to which it can be bonded.

[14] X 01 , X 02 and X 03 However, each is independently -O- or -S-

[13] a salt as described above.

[15] L 01 , L 02 and L 03 The salts described in

[13] or

[14] , each independently comprising a single bond or an alkanediyl group having 1 to 6 carbon atoms (the -CH2- contained in the alkanediyl group may be replaced by -O- or -CO-).

[16] AI - The salt is one of the following

[12] -

[15] , wherein the salt is a sulfonate anion, a sulfonylimide anion, or a sulfonylmethide anion.

[17] AI - is a sulfonate anion, and the sulfonate anion is a salt of any of the following

[12] -

[16] , which is an anion represented by formula (IA) or formula (IB). [Effects of the Invention]

[0006] By using a resist composition containing the salt of the present invention, resist patterns can be manufactured with good line edge roughness (LER). [Modes for carrying out the invention]

[0007] In this specification, "(meth)acrylic monomer" means "at least one of acrylic monomers and methacrylic monomers." The notations "(meth)acrylate" and "(meth)acrylic acid" have the same meaning. For groups described herein that can take both linear and branched structures, either is acceptable. When -CH2- contained in hydrocarbon groups, etc., is replaced by -O-, -S-, -CO- or -SO2-, the same example shall apply to each group. "Combined group" means a group formed by bonding two or more of the exemplified groups, and the valencies of these groups may be appropriately changed depending on the bonding configuration. "Derived from" or "induced" means that the polymerizable C=C bond contained in the molecule becomes a -CC- group (single bond) through polymerization. If stereoisomers exist, all stereoisomers are included.

[0008] [Salt represented by formula (I)] This invention relates to a salt represented by formula (I) (hereinafter sometimes referred to as "salt (I)"). In salts (I), the positively charged side is sometimes called a "cation (I)," and the negatively charged side is sometimes called an "anion (I)." [Cation (I)] The cation (I) of the salt represented by formula (I) is the cation represented by the following formula (IC). TIFF2023156258000008.tif62155[In formula (IC), all symbols have the same meaning as in formula (I).]

[0009] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. R 1 , R 2 , R 3 , R 4 , R 5 , R6 , R 7 , R 8 and R 9 A C1-C12 haloalkyl group refers to an alkyl group having a halogen atom and having C1-C12 atoms, and examples include C1-C12 alkyl fluorides, C1-C12 alkyl chlorides, C1-C12 alkyl bromides, and C1-C12 alkyl iodides. Examples of haloalkyl groups include C1-C12 perfluoroalkyl groups (trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, and iodomethyl group. The number of carbon atoms in the haloalkyl group is preferably 1-9, more preferably 1-6, even more preferably 1-4, and even more preferably 1-3. R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Examples of hydrocarbon groups having 1 to 36 carbon atoms include chain-type hydrocarbon groups such as alkyl groups and alkanediyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. The number of carbon atoms in the hydrocarbon group is preferably 1 to 30, more preferably 1 to 24, and even more preferably 1 to 18. Examples of alkyl groups include linear or branched alkyl groups, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, and dodecyl group. Alkanediyl groups include linear or branched alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and Examples of branched alkanediyl groups include ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 9, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be monocyclic or polycyclic, and examples include the groups shown below. The bonding site can be at any position. Specifically, monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl. Polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. Examples of aromatic hydrocarbon groups include phenyl groups, naphthyl groups, biphenyl groups, anthryl groups, phenanthryl groups, and binaphthyl groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10. Groups formed by combining two or more groups from among chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups include groups formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*, alkyl group-aromatic hydrocarbon group-alkanediyl group-*, the -CH2- contained in the alkanediyl group and the alkyl group may be replaced with -O-, -CO-, -S- or -SO2-), and groups formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group-al Examples include candiyl group-*, alkyl group-alicyclic hydrocarbon group-*, alkyl group-alicyclic hydrocarbon group-alkanediyl group-*, the -CH2- contained in the alicyclic hydrocarbon group, the alkanediyl group and the alkyl group may be replaced with -O-, -CO-, -S- or -SO2-, and groups combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, aromatic hydrocarbon group-alicyclic hydrocarbon group-*, alicyclic hydrocarbon group-aromatic hydrocarbon group-*, the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-). * indicates a bonding site. Examples of aromatic hydrocarbon groups - alkanediyl groups -* include aralkyl groups such as benzyl and phenethyl groups. Examples of alkyl-aromatic hydrocarbon groups-* include tolyl groups, xylyl groups, and cumenyl groups. Examples of alicyclic hydrocarbon groups - alkanediyl groups -* include cyclohexylmethyl group, cyclohexylethyl group, 1-(adamantan-1-yl)methyl group, 1-(adamantan-1-yl)-1-methylethyl group, and other cycloalkylalkyl groups. Examples of alkyl-alicyclic hydrocarbon groups include methylcyclohexyl group, dimethylcyclohexyl group, and cycloalkyl groups having alkyl groups such as 2-alkyladamantan-2-yl group. Examples of aromatic hydrocarbon groups - alicyclic hydrocarbon groups -* include the phenylcyclohexyl group. Examples of alicyclic hydrocarbon groups - aromatic hydrocarbon groups -* include the cyclohexylphenyl group. In addition, in the combination, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. Also, any of the groups may be W 1 , W 2 Or W 3 It may be bonded to an alicyclic hydrocarbon group or a benzene ring. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Haloalkyl groups and R represented by 4 , R 5 , R 6 , R 7 , R 8 and R 9 If the -CH2- contained in the hydrocarbon group represented by is replaced by -O-, -CO-, -S-, or -SO2-, the number of carbon atoms before replacement shall be the total number of carbon atoms in the haloalkyl group or the hydrocarbon group. Furthermore, this number may be one or two or more. Groups in which the -CH2- contained in haloalkyl groups and hydrocarbon groups is replaced with -O-, -S-, -SO2-, or -CO- include: hydroxyl group (a group in which the -CH2- contained in a methyl group is replaced with -O-), thiol group (a group in which the -CH2- contained in a methyl group is replaced with -S-), carboxyl group (a group in which the -CH2-CH2- contained in an ethyl group is replaced with -O-CO-), alkoxy group (a group in which the -CH2- at any position in an alkyl group is replaced with -O-), and alkoxycarbonyl group (a group in which the -CH2- at any position in an alkyl group is replaced with -O-). (A group in which -CH2-CH2- is replaced by -O-CO-), alkylcarbonyl group (A group in which -CH2- at any position in an alkyl group is replaced by -CO-), alkylcarbonyloxy group (A group in which -CH2-CH2- at any position in an alkyl group is replaced by -CO-O-), alkylthio group (A group in which -CH2- at any position in an alkyl group is replaced by -S-), alkylsulfonyl group (A group in which -CH2- at any position in an alkyl group is replaced by -SO2-), oxy group (A group in which -CH2- in a methylene group is replaced by -O-CO-), 2- is a group in which -O- is replaced, carbonyl group (a group in which -CH2- contained in a methylene group is replaced with -CO-), thio group (a group in which -CH2- contained in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- contained in a methylene group is replaced with -SO2-), alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -O-), alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), a Alkanediylcarbonyl group (a group in which any -CH2- in an alkanediyl group is replaced with -CO-), Alkanediylcarbonyloxy group (a group in which any -CH2-CH2- in an alkanediyl group is replaced with -CO-O-), Alkanediylthio group (a group in which any -CH2- in an alkanediyl group is replaced with -S-), Alkanediylsulfonyl group (a group in which any -CH2- in an alkanediyl group is replaced with -SO2-), Cycloalkoxy group, Cycloalkylalkoxy group,Examples include alkoxycarbonyloxy groups, aromatic hydrocarbon group-carbonyloxy groups, aromatic hydrocarbon group-carbonyl groups, aromatic hydrocarbon group-oxy groups, haloalkoxy groups (groups in which -CH2- at any position in a haloalkyl group is replaced with -O-), haloalkoxycarbonyl groups (groups in which -CH2-CH2- at any position in a haloalkyl group is replaced with -O-CO-), haloalkylcarbonyl groups (groups in which -CH2- at any position in a haloalkyl group is replaced with -CO-), haloalkylcarbonyloxy groups (groups in which -CH2-CH2- at any position in a haloalkyl group is replaced with -CO-O-), and groups that combine two or more of these groups. Examples of alkoxy groups include alkoxy groups having 1 to 35 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, and undecyloxy groups. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Alkoxycarbonyl groups, alkylcarbonyl groups, and alkylcarbonyloxy groups represent groups in which a carbonyl group or carbonyloxy group is bonded to an alkyl group or alkoxy group as described above. Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 35 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl groups. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 36 carbon atoms, such as acetyl, propionyl, and butyryl groups. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 35 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy groups. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of alkylthio groups include alkylthio groups having 1 to 35 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, and undecylthio group. The number of carbon atoms in the alkylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkylsulfonyl groups include alkylsulfonyl groups having 1 to 35 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, octylsulfonyl group, 2-ethylhexylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, and undecylsulfonyl group. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediyloxy groups include alkanediyloxy groups having 1 to 35 carbon atoms, such as methyleneoxy, ethyleneoxy, propanediyloxy, butanediyloxy, and pentanediyloxy groups. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediyloxycarbonyl groups include alkanediyloxycarbonyl groups having 2 to 35 carbon atoms, such as methyleneoxycarbonyl groups, ethyleneoxycarbonyl groups, propanediyloxycarbonyl groups, and butanediyloxycarbonyl groups. Examples of alkanediylcarbonyl groups include alkanediylcarbonyl groups having 2 to 36 carbon atoms, such as methylenecarbonyl groups, ethylenecarbonyl groups, propanediylcarbonyl groups, butanediylcarbonyl groups, and pentanediylcarbonyl groups. Examples of alkanediylcarbonyloxy groups include alkanediylcarbonyloxy groups having 2 to 35 carbon atoms, such as methylenecarbonyloxy groups, ethylenecarbonyloxy groups, propanediylcarbonyloxy groups, and butanediylcarbonyloxy groups. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of alkanediylthio groups include alkanediylthio groups having 1 to 35 carbon atoms, such as methylenethio groups, ethylenethio groups, and propylenethio groups. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediylsulfonyl groups include alkanediylsulfonyl groups having 1 to 35 carbon atoms, such as methylenesulfonyl groups, ethylenesulfonyl groups, and propylenesulfonyl groups. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 35 carbon atoms, such as the cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 36 carbon atoms, such as the cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 34 carbon atoms, such as the butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 35 carbon atoms, such as the benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 36 carbon atoms, such as the benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 35 carbon atoms, such as the phenyloxy group. Examples of haloalkoxy groups, haloalkoxycarbonyl groups, haloalkylcarbonyl groups, and haloalkylcarbonyloxy groups include haloalkoxy groups having 1 to 11 carbon atoms, haloalkoxycarbonyl groups having 2 to 11 carbon atoms, haloalkylcarbonyl groups having 2 to 12 carbon atoms, and haloalkylcarbonyloxy groups having 2 to 11 carbon atoms. For example, groups obtained by replacing one or more hydrogen atoms of the above-mentioned groups with halogen atoms are also included. Furthermore, groups in which the -CH2- contained in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO-, or -SO2- include the groups shown below. Also, among the groups shown below, groups in which -O- is replaced with -S- and -CO- is replaced with -SO2- are also examples. The bonding site can be at any position. TIFF2023156258000010.tif46169

[0010] R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Examples of substituents that the hydrocarbon group may have include halogen atoms and cyano groups. Examples of halogen atoms include the same groups as those described above. The hydrocarbon group may have one substituent or more substituents.

[0011] A 1 , A 2 and A 3 Examples of hydrocarbon groups include linear or branched chain hydrocarbon groups (e.g., alkanediyl groups), monocyclic or polycyclic alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. Two or more of these groups may be combined. The number of carbon atoms in the hydrocarbon group is preferably 1 to 19, more preferably 1 to 18, even more preferably 1 to 16, even more preferably 1 to 14, and even more preferably 1 to 12. Examples of linear hydrocarbon groups include linear alkane diyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl. Examples of branched alkanediyl groups include ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 9, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be monocyclic or polycyclic, and examples include the groups shown below. The bonding site can be at any position. Specifically, monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, and cyclooctane-1,5-diyl group, as well as monocyclic alicyclic hydrocarbon groups and Examples include polycyclic alicyclic hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, even more preferably 3 to 12, and even more preferably 3 to 10. Examples of aromatic hydrocarbon groups include phenylene groups, naphthylene groups, anthrylene groups, biphenylene groups, phenanthrylene groups, and other arylene groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10.

[0012] Groups formed by combining two or more groups include groups formed by combining an alicyclic hydrocarbon group and an alkanediyl group, groups formed by combining an aromatic hydrocarbon group and an alkanediyl group, and groups formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group. In the combinations, two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups may be combined. Furthermore, any of the groups may be bonded to a benzene ring. Examples of groups combining an alicyclic hydrocarbon group and an alkanediyl group include -divalent alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent alicyclic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent alicyclic hydrocarbon group-. Examples of groups combining an aromatic hydrocarbon group and an alkanediyl group include -divalent aromatic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent aromatic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent aromatic hydrocarbon group-. Examples of groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group include -aromatic hydrocarbon group-alicyclic hydrocarbon group-, -alicyclic hydrocarbon group-aromatic hydrocarbon group-, and -alicyclic hydrocarbon group-aromatic hydrocarbon group-alicyclic hydrocarbon group-.

[0013] A 1 , A 2 and A 3 If the -CH2- contained in a hydrocarbon group is replaced by -O-, -CO-, -S-, or -SO2-, the number of carbon atoms before replacement is considered the total number of carbon atoms in the hydrocarbon group. This number may be one or two or more, but it is preferably one to three. Groups in which the -CH2- contained in a hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2- include: hydroxyl group (a group in which the -CH2- contained in a methyl group is replaced with -O-), carboxyl group (a group in which the -CH2-CH2- contained in an ethyl group is replaced with -O-CO-), thiol group (a group in which the -CH2- contained in a methyl group is replaced with -S-), alkoxy group (a group in which the -CH2- at any position in an alkyl group is replaced with -O-), alkoxycarbonyl group (a group in which the -CH2-CH2- at any position in an alkyl group is replaced with -O-) , a group replaced by -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in the alkyl group is replaced by -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in the alkyl group is replaced by -CO-O-), alkylthio group (a group in which -CH2- at any position in the alkyl group is replaced by -S-), alkylsulfonyl group (a group in which -CH2- at any position in the alkyl group is replaced by -SO2-), oxy group (a group in which -CH2- in the methylene group is replaced by -O-) (a group in which -CH2- in the methylene group is replaced by -CO-), thio group (a group in which -CH2- in the methylene group is replaced by -S-), sulfonyl group (a group in which -CH2- in the methylene group is replaced by -SO2-), alkanediyloxy group (a group in which -CH2- at any position in the alkanediyl group is replaced by -O-), alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in the alkanediyl group is replaced by -O-CO-), alkanediylcarbonyl group (a (A group in which -CH2- at any position in the alkanediyl group is replaced with -CO-), alkanediylcarbonyloxy group (A group in which -CH2-CH2- at any position in the alkanediyl group is replaced with -CO-O-), alkanediylsulfonyl group (A group in which -CH2- at any position in the alkanediyl group is replaced with -SO2-), alkanediylthio group (A group in which -CH2- at any position in the alkanediyl group is replaced with -S-), cycloalkoxy group, cycloalkylalkoxy group, alkoxycarbonyloxy group,Examples include aromatic hydrocarbon group-carbonyloxy group, aromatic hydrocarbon group-carbonyl group, aromatic hydrocarbon group-oxy group, and groups combining two or more of these groups. Examples of alkoxy groups include alkoxy groups having 1 to 19 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, and undecyloxy groups. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Alkoxycarbonyl groups, alkylcarbonyl groups, and alkylcarbonyloxy groups represent groups in which a carbonyl group or carbonyloxy group is bonded to an alkyl group or alkoxy group as described above. Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 19 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl groups. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 20 carbon atoms, such as acetyl, propionyl, and butyryl groups. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 19 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy groups. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of alkylthio groups include alkylthio groups having 1 to 19 carbon atoms, such as methylthio groups, ethylthio groups, propylthio groups, and butylthio groups. The number of carbon atoms in the alkylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkylsulfonyl groups include alkylsulfonyl groups having 1 to 19 carbon atoms, such as methylsulfonyl groups, ethylsulfonyl groups, and propylsulfonyl groups. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediyloxy groups include alkanediyloxy groups having 1 to 19 carbon atoms, such as methyleneoxy, ethyleneoxy, propanediyloxy, butanediyloxy, and pentanediyloxy groups. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediyloxycarbonyl groups include alkanediyloxycarbonyl groups having 2 to 19 carbon atoms, such as methyleneoxycarbonyl groups, ethyleneoxycarbonyl groups, propanediyloxycarbonyl groups, and butanediyloxycarbonyl groups. Examples of alkanediylcarbonyl groups include alkanediylcarbonyl groups having 2 to 20 carbon atoms, such as methylenecarbonyl groups, ethylenecarbonyl groups, propanediylcarbonyl groups, butanediylcarbonyl groups, and pentanediylcarbonyl groups. Examples of alkanediylcarbonyloxy groups include alkanediylcarbonyloxy groups having 2 to 19 carbon atoms, such as methylenecarbonyloxy groups, ethylenecarbonyloxy groups, propanediylcarbonyloxy groups, and butanediylcarbonyloxy groups. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of alkanediylsulfonyl groups include alkanediylsulfonyl groups having 1 to 19 carbon atoms, such as methylenesulfonyl groups, ethylenesulfonyl groups, and propylenesulfonyl groups. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediylthio groups include alkanediylthio groups having 1 to 19 carbon atoms, such as methylenethio groups, ethylenethio groups, and propylenethio groups. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 19 carbon atoms, such as the cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 19 carbon atoms, such as the cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 18 carbon atoms, such as the butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 19 carbon atoms, such as the benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 20 carbon atoms, such as the benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 19 carbon atoms, such as the phenyloxy group.

[0014] Furthermore, groups in which the -CH2- contained in an alicyclic hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2- include the groups shown below. Also, among the groups shown below, groups in which -O- is replaced with -S- and -CO- is replaced with -SO2- are also examples. The bonding site can be at any position. TIFF2023156258000012.tif46170A 1 , A 2 and A 3 The substituents that the hydrocarbon group may have include R 4 ~R 9 The hydrocarbon group may have substituents similar to those listed above.

[0015] A 1 , A 2 and A 3Preferably, each of these is a hydrocarbon group having 1 to 20 carbon atoms (the hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-; however, at least one of the -CH2- contained in the hydrocarbon group is replaced with -O-, -CO-, -S- or -SO2-). Specifically, A 1 is ***-L 011 -X 01 -L 012 - and A 2 is ***-L 021 -X 02 -L 022 - and A 3 is ***-L 031 -X 03 -L 032 -is (X 01 , X 02 and X 03 These represent -O-, -CO-, -S-, or -SO2- independently. 011 , L 012 , L 021 , L 022 , L 031 and L 032 Each of these independently represents a single bond or a hydrocarbon group having 1 to 19 carbon atoms, and the hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-. However, L 011 and L 012 The total number of carbon atoms is 0 to 19, L 021 and L 022 The total number of carbon atoms is 0 to 19, L 031 and L 032 The total number of carbon atoms is between 0 and 19. *** is A 1 , A 2 Or A 3 This represents the bonding site with the benzene ring to which it can be bonded. ) is more preferable, A 1 is, ***-X 01 -L 01 - or ***-L 01 -X 01 - and A 2 is, ***-X 02 -L02 - or ***-L 02 -X 02 - and A 3 is, ***-X 03 -L 03 - or ***-L 03 -X 03 -is (X 01 , X 02 and X 03 These represent -O-, -CO-, -S-, or -SO2- independently. 01 , L 02 and L 03 Each of these independently represents a single bond or a hydrocarbon group having 1 to 19 carbon atoms, and the hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-. *** is A 1 , A 2 Or A 3 This represents the bonding site with the benzene ring to which it can be bonded. ) is even more preferable. A 1 , A 2 and A 3 It is preferable that the molecule has no substituents other than substitution with -O-, -CO-, -S-, or -SO2-. L 011 , L 012 , L 021 , L 022 , L 031 , L 032 , L 01 , L 02 and L 03 As a hydrocarbon group having 1 to 19 carbon atoms (the hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-), A 1 , A 2 and A 3 Similar groups to those listed above can be cited. X 01 , X 02 and X 03 Each of these is preferably -O- or -S-, and more preferably -O-. L 011 , L 012, L 021 , L 022 , L 031 , L 032 , L 01 , L 02 and L 03 Each of these is preferably a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S-, or -SO2-), more preferably a single bond or a hydrocarbon group having 1 to 12 carbon atoms (the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S-, or -SO2-), and preferably a single bond or a chain hydrocarbon group having 1 to 9 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be replaced with -O-, -CO-, -S-, or -SO2-). It is even more preferable that it is a single bond or an alkanediyl group having 1 to 6 carbon atoms (the -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), it is even more preferable that it is a single bond or an alkanediyl group having 1 to 4 carbon atoms (the -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), and it is even more preferable that it is a single bond or an alkanediyl group having 1 to 3 carbon atoms (the -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-). In particular, single bonds, methylene groups, ethane-1,1-diyl groups, propane-1,1-diyl groups, propane-2,2-diyl groups, carbonyl groups, carbonyloxy groups, carbonyloxymethylene groups, ethyleneoxymethylene groups, methylenecarbonyloxy groups, methylenecarbonyloxymethylene groups, or ethyleneoxycarbonyl groups are preferred. A 1 , A 2 and A 3 The bond positions to the benzene ring are, independently of each other, S + The bond position can be any of the or, m, or p positions. Specifically, if m1, m2, and m3 are 1, A 1 , A 2 and A 3 Each of them is independent of S +It is preferable that the bond is at the p-position or m-position relative to the bond site, and more preferably at the p-position. 1 , A 2 and A 3 Each of them is independent of S + It is preferable that one atom is bonded to the orthogonal or m-position, one atom is bonded to the orthogonal or m-position, and it is more preferable that two atoms are bonded to the m-position. When m1, m2 and m3 are 3, A 1 , A 2 and A 3 Each of them is independent of S + It is preferable that two are bonded to the oro or m position and one is bonded to the p or m position relative to the bonding site, and it is more preferable that two are bonded to the m position and one is bonded to the p position. When m1, m2 and m3 are 4, A 1 , A 2 and A 3 Each of them is independent of S + It is preferable that two of the atoms are bonded at the ortho or metapositional position, and two are bonded at the p or metapositional position, and it is more preferable that two are bonded at the orthoposition and two are bonded at the metapositional position.

[0016] W 1 , W 2 and W 3 The alicyclic hydrocarbon group can be either monocyclic or polycyclic, and examples include the groups shown below. The bonding site can be at any position. Specifically, monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl. Polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl; cycloalkyl groups such as spirocyclohexane-1,2'-cyclopentane and spiroadamantane-2,3'-cyclopentane; and spiro rings having cycloalkyl groups spiro-bonded to norvonyl or adamantyl groups. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 20, even more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 3 to 12.

[0017] Furthermore, groups in which the -CH2- contained in an alicyclic hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2- include the groups shown below. Also, among the groups shown below, groups in which -O- is replaced with -S- and -CO- is replaced with -SO2- are also examples. The bonding site can be at any position. TIFF2023156258000014.tif47168

[0018] W 1 , W 2 and W 3The alicyclic hydrocarbon group (the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, or -SO2-) is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, or -SO2-), more preferably a group represented by any of formulas (w1-1) to (w1-24), even more preferably a group represented by any of formulas (w1-1) to (w1-6) and formulas (w1-12) to (w1-24), and still more preferably a group represented by any of formulas (w1-1) to (w1-3), formulas (w1-15), and formulas (w1-22). TIFF2023156258000015.tif46168 [Formula (w1-1) to (w1-24), The -CH2- group may be replaced with -O-, -S-, -CO-, or -SO2-. The bonding site can be at any position. Among them, W 1 , W 2 and W 3 The group is preferably a cyclohexyl group or an adamantyl group, and more preferably an adamantyl group.

[0019] m1 is preferably 1, 2, 3, or 4, more preferably 1, 2, or 3, even more preferably 1 or 2, and even more preferably 1. m2 is preferably 0, 1, 2, 3, or 4, more preferably 0, 1, 2, or 3, even more preferably 0, 1, or 2, even more preferably 0 or 1, and even more preferably 0. m3 is preferably 0, 1, 2, 3, or 4, more preferably 0, 1, 2, or 3, even more preferably 0, 1, or 2, even more preferably 0 or 1, and even more preferably 0. m4 is preferably an integer from 0 to 5, more preferably an integer from 0 to 4, even more preferably an integer from 0 to 3, even more preferably 0, 1, or 2, and even more preferably 0 or 1. m5 is preferably an integer from 0 to 5, more preferably an integer from 0 to 4, even more preferably an integer from 0 to 3, even more preferably 0, 1, or 2, and even more preferably 0 or 1. m6 is preferably an integer from 0 to 5, more preferably an integer from 0 to 4, even more preferably an integer from 0 to 3, even more preferably 0, 1, or 2, and even more preferably 0 or 1. m7 is preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, even more preferably 0 or 1, and even more preferably 0. m8 is preferably 0, 1, 2, or 3, and more preferably 0, 1, or 3. m9 is preferably 0, 1, 2, or 3, and more preferably 0, 1, or 3. R 1 , R 2 and R 3 Each of these is preferably independently a hydrogen atom, a halogen atom, or a C1-C6 haloalkyl group (the -CH2- contained in the haloalkyl group may be replaced with -O- or -CO-), more preferably a hydrogen atom, a halogen atom, or a C1-C4 fluoride alkyl group, even more preferably a hydrogen atom, a fluorine atom, an iodine atom, a bromine atom, or a C1-C4 perfluoroalkyl group, even more preferably a hydrogen atom, a fluorine atom, an iodine atom, a bromine atom, or a trifluoromethyl group, and even more preferably an iodine atom. However, R 1 , R 2 and R 3 At least one of them is a halogen atom-containing group. R 4 , R 5and R 6 Each of these is preferably independently a halogen atom, a C1-C6 haloalkyl group, or a C1-C6 alkyl group (the -CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a C1-C4 fluoride alkyl group, or a C1-C4 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), even more preferably a fluorine atom, an iodine atom, a bromine atom, a C1-C4 perfluoroalkyl group, or a C1-C4 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), even more preferably a fluorine atom, an iodine atom, a bromine atom, a methyl group, a hydroxyl group, or a trifluoromethyl group, and even more preferably an iodine atom. R 7 , R 8 and R 9 Each of these is preferably independently a halogen atom, a C1-C6 haloalkyl group, or a C1-C6 alkyl group (the -CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a C1-C4 fluoride alkyl group, or a C1-C4 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), even more preferably a fluorine atom, an iodine atom, a C1-C4 perfluoroalkyl group, or a C1-C4 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methoxy group, a methyl group, or a t-butyl group. R 7 , R 8 and R 9 The bond positions to the benzene ring are, independently of each other, S + The bond position can be any of the or, m, or p positions. In particular, when m7, m8, and m9 are 1, R 7 , R 8 and R 9Each of them is independent of S + It is preferable that the bond is at the p-position or m-position relative to the bond site, and more preferably at the p-position. 7 , R 8 and R 9 Each of them is independent of S + It is preferable that one atom is bonded to the ortho or m position and one atom is bonded to the p or m position relative to the bonding site, and more preferably that one atom is bonded to the m position and one atom is bonded to the p or m position. When m7, m8 and m9 are 3, R 7 , R 8 and R 9 Each of them is independent of S + It is preferable that two are bonded to the oro or m position and one is bonded to the p or m position relative to the bonding site, and it is more preferable that two are bonded to the m position and one is bonded to the p position. When m7, m8 and m9 are 4, R 7 , R 8 and R 9 Each of them is independent of S + It is preferable that two atoms are bonded to the ortho or m position and two atoms are bonded to the p or m position relative to the bonding site, and it is more preferable that two atoms are bonded to the m position, one atom is bonded to the ortho position and one atom is bonded to the p position.

[0020] Examples of cations represented by formula (IC) include the cation represented by formula (IC-1) (hereinafter sometimes referred to as "cation (IC-1)"). TIFF2023156258000016.tif61161[In formula (IC-1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , m1, m2, m3, m4, m5, m6, m7, m8, m9, W 1 , W 2 , W 3 , L 01 , L02 , L 03 , X 01 , X 02 and X 03 The symbol has the same meaning as described above. X 01 , X 02 and X 03 The bond positions to the benzene ring are, independently of each other, A 1 , A 2 and A 3 This is similar to the bond position to the benzene ring.

[0021] Examples of cations of salt (I) include those represented by the following formulas (Ic-1) to (Ic-90). TIFF2023156258000017.tif245166

[0022] TIFF2023156258000018.tif239166

[0023] TIFF2023156258000019.tif249169

[0024] TIFF2023156258000020.tif249164

[0025] TIFF2023156258000021.tif72130

[0026] [Anion (I)] The anion (I) of the salt represented by equation (I) is AI - This is an organic anion represented by [formula]. AI - Examples of organic anions represented by AI include sulfonic acid anions, sulfonylimide anions, or sulfonylmethide anions. - The organic anion represented by is preferably a sulfonate anion, and more preferably an anion represented by formula (IA) or formula (IB). TIFF2023156258000022.tif2965[In formula (IA), Q1 and Q 2 Each of these independently represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms. L 1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and the -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. Y 1 This represents a methyl group which may have substituents or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-.

[0027] In formula (IA), if a -CH2- contained in a saturated hydrocarbon group is replaced with -O- or -CO-, the number of carbon atoms before the replacement shall be the number of carbon atoms in the saturated hydrocarbon group. Similarly, if a -CH2- contained in a cyclic hydrocarbon group is replaced with -O-, -S-, -SO2-, or -CO-, the number of carbon atoms before the replacement shall be the number of carbon atoms in the cyclic hydrocarbon group.

[0028] Q 1 and Q 2 Examples of perfluoroalkyl groups having 1 to 6 carbon atoms include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, and perfluorohexyl groups. Q 1 and Q 2 Examples of C1-C6 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. Q 1 and Q 2 Q 1 and Q 2Preferably, at least one of them contains a fluorine atom or a perfluoroalkyl group, more preferably independently a fluorine atom or a perfluoroalkyl group, even more preferably a fluorine atom or a trifluoromethyl group, and even more preferably both being fluorine atoms.

[0029] L 1 Examples of divalent saturated hydrocarbon groups in this context include linear alkanediyl groups, branched alkanediyl groups, and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups. Groups formed by combining two or more of these groups may also be used. Specifically, linear alkane diyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, and heptadecane-1,17-diyl group; Branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group; Monocyclic, divalent, alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; Examples include polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group. L 1Examples of groups in which the -CH2- contained in the divalent saturated hydrocarbon group represented by is replaced with -O- or -CO- include the group represented by any of the formulas (b1-1) to (b1-3). In the groups represented by formulas (b1-1) to (b1-3) and their specific examples, the groups represented by formulas (b1-4) to (b1-11), * and ** represent the bonding site, and * is -Y 1 This represents the connection point.

[0030] TIFF2023156258000023.tif26118[In formula (b1-1), L b2 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b3 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, wherein the hydrogen atoms in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups, and the -CH2- in the saturated hydrocarbon group may be replaced with -O- or -CO-. However, L b2 and L b3 The total number of carbon atoms is 22 or less. In formula (b1-2), L b4 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b5 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, wherein the hydrogen atoms in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups, and the -CH2- in the saturated hydrocarbon group may be replaced with -O- or -CO-. However, L b4 and L b5 The total number of carbon atoms is 22 or less. In formula (b1-3), L b6This represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. L b7 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, wherein the hydrogen atoms in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups, and the -CH2- in the saturated hydrocarbon group may be replaced with -O- or -CO-. However, L b6 and L b7 The total number of carbon atoms is 23 or less.

[0031] In groups represented by formulas (b1-1) to (b1-3), if the -CH2- contained in the saturated hydrocarbon group is replaced by -O- or -CO-, the number of carbon atoms before the replacement shall be the number of carbon atoms of the saturated hydrocarbon group. As for divalent saturated hydrocarbon groups, L 1 Examples include divalent saturated hydrocarbon groups. L b2 These are preferably a single bond, a methylene group, -CH(CF3)-, and -C(CF3)2-. L b3 This is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b4 Preferably, is a divalent saturated hydrocarbon group having 1 to 8 carbon atoms, and the hydrogen atoms in the divalent saturated hydrocarbon group may be substituted with fluorine atoms, and more preferably is a methylene group, -CH(CF3)-, or -C(CF3)2-. L b5 Preferably, it is a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b6 Preferably, it is a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b7Preferably, the saturated hydrocarbon group is a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the hydrogen atoms in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups, and the -CH2- groups in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L 1 As for the group in which the -CH2- contained in the divalent saturated hydrocarbon group represented by is replaced with -O- or -CO-, the group represented by formula (b1-1) or formula (b1-3) is preferred.

[0032] The groups represented by formula (b1-1) include those represented by formulas (b1-4) to (b1-8), respectively. TIFF2023156258000024.tif48120[In formula (b1-4), L b8 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. In formula (b1-5), L b9 This represents a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b10 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, and the hydrogen atoms in the divalent saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. However, L b9 and L b10 The total number of carbon atoms is 20 or less. In formula (b1-6), L b11 This represents a divalent saturated hydrocarbon group with 1 to 21 carbon atoms. L b12 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atoms in the divalent saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. However, L b11 and L b12 The total number of carbon atoms is 21 or less. In formula (b1-7), L b13 This represents a divalent saturated hydrocarbon group with 1 to 19 carbon atoms. L b14 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-. L b15 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the hydrogen atoms in the divalent saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. However, L b13 ~L b15 The total number of carbon atoms is 19 or less. In formula (b1-8), L b16 This represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b17 This represents a divalent saturated hydrocarbon group with 1 to 18 carbon atoms. L b18 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 17 carbon atoms, and the hydrogen atoms in the divalent saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. However, L b16 ~L b18 The total number of carbon atoms is 19 or less. L b8 This is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b9 Preferably, it is a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b10 Preferably, it is a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b11 Preferably, it is a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b12 Preferably, it is a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b13This is preferably a divalent saturated hydrocarbon group having 1 to 12 carbon atoms. L b14 This is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 6 carbon atoms. L b15 Preferably, it is a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b16 This is preferably a divalent saturated hydrocarbon group having 1 to 12 carbon atoms. L b17 This is preferably a divalent saturated hydrocarbon group having 1 to 6 carbon atoms. L b18 Preferably, it is a single bond or a divalent saturated hydrocarbon group having 1 to 17 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms.

[0033] The groups represented by formula (b1-3) include those represented by formulas (b1-9) to (b1-11), respectively. TIFF2023156258000025.tif23140[In formula (b1-9), L b19 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b20 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxyl group, or an alkylcarbonyloxy group. The -CH2- in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and the hydrogen atoms in the alkylcarbonyloxy group may be substituted with a hydroxyl group. However, L b19 and L b20 The total number of carbon atoms is 23 or less. In formula (b1-10), L b21This represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b22 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b23 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and the hydrogen atoms in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxyl group, or an alkylcarbonyloxy group. The -CH2- in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and the hydrogen atoms in the alkylcarbonyloxy group may be substituted with a hydroxyl group. However, L b21 , L b22 and L b23 The total number of carbon atoms is 21 or less. In formula (b1-11), L b24 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b25 This represents a divalent saturated hydrocarbon group with 1 to 21 carbon atoms. L b26 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atoms in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxyl group, or an alkylcarbonyloxy group. The -CH2- in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and the hydrogen atoms in the alkylcarbonyloxy group may be substituted with a hydroxyl group. However, L b24 , L b25 and L b26 The total number of carbon atoms is 21 or less. Furthermore, in the group represented by formula (b1-9) through the group represented by formula (b1-11), if a hydrogen atom in a saturated hydrocarbon group is substituted with an alkylcarbonyloxy group, the number of carbon atoms before the substitution shall be the number of carbon atoms in the saturated hydrocarbon group. Examples of alkylcarbonyloxy groups include acetyloxy group, propionyloxy group, butyryloxy group, cyclohexylcarbonyloxy group, and adamantylcarbonyloxy group.

[0034] The following are examples of bases represented by formula (b1-4): TIFF2023156258000026.tif13132

[0035] The following are examples of bases represented by formula (b1-5): TIFF2023156258000027.tif62150

[0036] The following are examples of bases represented by formula (b1-6): TIFF2023156258000028.tif28166

[0037] The following are examples of bases represented by formula (b1-7): TIFF2023156258000029.tif41169

[0038] The following are examples of bases represented by formula (b1-8): TIFF2023156258000030.tif21122

[0039] The following are examples of bases represented by formula (b1-2): TIFF2023156258000031.tif31161

[0040] The following are examples of bases represented by formula (b1-9): TIFF2023156258000032.tif34153

[0041] The following are examples of bases represented by formula (b1-10): TIFF2023156258000033.tif79166

[0042] The following are examples of bases represented by formula (b1-11): TIFF2023156258000034.tif67153

[0043] Y 1 Examples of cyclic hydrocarbon groups represented by this symbol include alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups that combine alicyclic hydrocarbon groups and aromatic hydrocarbon groups.

[0044] Y 1 Examples of alicyclic hydrocarbon groups in which the -CH2- contained in the alicyclic hydrocarbon group represented by is not replaced by -O-, -S-, -SO2-, or -CO- include the groups represented by formulas (Y1) to (Y11) and (Y36) to (Y38). Y 1 When the -CH2- contained in the alicyclic hydrocarbon group represented by is replaced by -O-, -S-, -SO2-, or -CO-, the number of replacements may be one or two or more. Examples of such groups include those represented by formulas (Y12) to (Y35) and (Y39) to (Y43). The -O- or -CO- in the groups represented by formulas (Y12) to (Y35) and (Y39) to (Y43) may also be replaced by -S- or -SO2-. * is L 1 This represents the connection point. TIFF2023156258000035.tif85164

[0045] Y 1 The alicyclic hydrocarbon group represented is preferably a group represented by any of formulas (Y1) to (Y20), (Y26), (Y27), (Y30), (Y31), (Y39) to (Y43), more preferably a group represented by formula (Y11), (Y15), (Y16), (Y20), (Y26), (Y27), (Y30), (Y31), (Y39), (Y40), (Y42), or (Y43), and even more preferably a group represented by formula (Y11), (Y15), (Y20), (Y26), (Y27), (Y30), (Y31), (Y39), (Y40), (Y42), or (Y43). Y 1 When the alicyclic hydrocarbon group represented by is a spiro ring having an oxygen atom, such as formulas (Y28) to (Y35), (Y39), (Y40), (Y42), or (Y43), it is preferable that the alkanediyl group between the two oxygen atoms has one or more fluorine atoms. Furthermore, it is preferable that the methylene group adjacent to the oxygen atom among the alkanediyl groups contained in the ketal structure is not substituted with a fluorine atom. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 20, even more preferably 3 to 18, and even more preferably 3 to 16.

[0046] Y 1 Examples of aromatic hydrocarbon groups represented by include phenyl groups, naphthyl groups, biphenyl groups, anthryl groups, phenanthryl groups, and binaphthyl groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 24, more preferably 6 to 20, even more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10.

[0047] Y 1 The substituents of the methyl group represented by can be halogen atoms, hydroxyl groups, alicyclic hydrocarbon groups with 3 to 16 carbon atoms, aromatic hydrocarbon groups with 6 to 18 carbon atoms, glycidyloxy groups, and -(CH2) ja -CO-OR b1 Base or -(CH2) ja -O-CO-R b1 group (in the formula, R b1 ) represents an alkyl group having 1 to 16 carbon atoms, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. ja represents an integer from 0 to 4. The -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced with -O-, -SO2-, or -CO-, and the hydrogen atoms contained in the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may be replaced with a hydroxyl group or a fluorine atom. ) are examples. Y 1Substituents for the cyclic hydrocarbon group represented by include halogen atoms, hydroxyl groups, C1-C16 alkyl groups which may be substituted with hydroxyl groups (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), C3-C16 alicyclic hydrocarbon groups, C6-C18 aromatic hydrocarbon groups, C7-C21 aralkyl groups, glycidyloxy groups, and -(CH2) ja -CO-OR b1 Base or -(CH2) ja -O-CO-R b1 group (in the formula, R b1 ) represents an alkyl group having 1 to 16 carbon atoms, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. ja represents an integer from 0 to 4. The -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced with -O-, -SO2-, or -CO-, and the hydrogen atoms contained in the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may be replaced with a hydroxyl group or a fluorine atom. ) are examples.

[0048] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. Examples of alicyclic hydrocarbon groups include cyclopentyl group, cyclohexyl group, methylcyclohexyl group, dimethylcyclohexyl group, cycloheptyl group, cyclooctyl group, norbornyl group, and adamantyl group. Alicyclic hydrocarbon groups may also have chain hydrocarbon groups, such as methylcyclohexyl group and dimethylcyclohexyl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 12, and more preferably 3 to 10. Examples of aromatic hydrocarbon groups include phenyl groups, naphthyl groups, anthryl groups, biphenyl groups, phenanthryl groups, and other aryl groups. Aromatic hydrocarbon groups may have a chain-type hydrocarbon group or an alicyclic hydrocarbon group, and examples include aromatic hydrocarbon groups having a chain-type hydrocarbon group with 1 to 18 carbon atoms (tolyl group, xylyl group, cumenyl group, mesityl group, p-methylphenyl group, p-ethylphenyl group, p-tert-butylphenyl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), and aromatic hydrocarbon groups having an alicyclic hydrocarbon group with 3 to 18 carbon atoms (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.). The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 14, and more preferably 6 to 10. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, 2-ethylhexyl, octyl, nonyl, decyl, undecyl, and dodecyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. Examples of alkyl groups substituted with a hydroxyl group include hydroxymethyl groups, hydroxyethyl groups, and other hydroxyalkyl groups. Examples of aralkyl groups include benzyl groups, phenethyl groups, phenylpropyl groups, naphthylmethyl groups, and naphthylethyl groups. Groups in which the -CH2- group in an alkyl group is replaced with -O-, -SO2-, or -CO- include alkoxy groups, alkylsulfonyl groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, or combinations thereof. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, and dodecyloxy groups. The number of carbon atoms in the alkoxy group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. Examples of alkylsulfonyl groups include methylsulfonyl groups, ethylsulfonyl groups, and propylsulfonyl groups. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. Examples of alkoxycarbonyl groups include methoxycarbonyl groups, ethoxycarbonyl groups, and butoxycarbonyl groups. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of alkylcarbonyl groups include acetyl groups, propionyl groups, and butyryl groups. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of alkylcarbonyloxy groups include acetyloxy groups, propionyloxy groups, and butyryloxy groups. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of combined groups include groups combining an alkoxy group and an alkyl group, groups combining two alkoxy groups, groups combining an alkoxy group and an alkylcarbonyl group, and groups combining an alkoxy group and an alkylcarbonyloxy group. Examples of groups combining an alkoxy group and an alkyl group include alkoxyalkyl groups such as methoxymethyl, methoxyethyl, ethoxyethyl, and ethoxymethyl groups. The number of carbon atoms in the alkoxyalkyl group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of groups formed by combining alkoxy groups include alkoxyalkoxy groups such as methoxymethoxy, methoxyethoxy, ethoxymethoxy, and ethoxyethoxy. The number of carbon atoms in the alkoxyalkoxy group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of groups combining an alkoxy group and an alkylcarbonyl group include alkoxyalkylcarbonyl groups such as methoxyacetyl group, methoxypropionyl group, ethoxyacetyl group, and ethoxypropionyl group. The number of carbon atoms in the alkoxyalkylcarbonyl group is preferably 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. Examples of groups combining an alkoxy group and an alkylcarbonyloxy group include alkoxyalkylcarbonyloxy groups such as methoxyacetyloxy group, methoxypropionyloxy group, ethoxyacetyloxy group, and ethoxypropionyloxy group. The number of carbon atoms in the alkoxyalkylcarbonyloxy group is preferably 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. Groups in which the -CH2- group in an alicyclic hydrocarbon group is replaced with -O-, -SO2-, or -CO- include the groups represented by formulas (Y12) to (Y35) and (Y39) to (Y43).

[0049] Y 1 Preferably, the alicyclic hydrocarbon group having 3 to 24 carbon atoms may have substituents or aromatic hydrocarbon group having 6 to 24 carbon atoms may have substituents; more preferably, the alicyclic hydrocarbon group having 3 to 20 carbon atoms may have substituents or aromatic hydrocarbon group having 6 to 20 carbon atoms may have substituents; even more preferably, the alicyclic hydrocarbon group having 3 to 18 carbon atoms may have substituents or aromatic hydrocarbon group having 6 to 18 carbon atoms may have substituents; even more preferably, the adamantyl group having substituents, norbornyl group having substituents, or phenyl group having substituents, wherein the -CH2- constituting the alicyclic hydrocarbon group, adamantyl group, and norbornyl group may be replaced with -O-, -S-, -SO2-, or -CO-, and specifically, the following are examples. TIFF2023156258000036.tif172159 Among them, Y 1Preferably, the group is an adamantyl group, a hydroxyadamantyl group, an oxoadamantyl group, a norbornane lactone group, a phenyl group, a group containing these, or a group represented by formulas (Y42), (Y100) to (Y114), (Y134) to (Y139), and particularly preferably a hydroxyadamantyl group, an oxoadamantyl group, a group containing these, or a group represented by formulas (Y42), (Y100) to (Y114), (Y134) to (Y139).

[0050] The anions represented by formula (IA) are preferably those represented by formulas (IA-1) to (IA-85) (hereinafter, they may be referred to as "anion (IA-1)," etc., depending on the formula number), and more preferably those represented by any of formulas (IA-1) to (IA-4), (IA-9), (IA-10), (IA-24) to (IA-33), (IA-36) to (IA-40), or (IA-47) to (IA-81).

[0051] TIFF2023156258000037.tif232169

[0052] TIFF2023156258000038.tif231154

[0053] JPEG2023156258000039.jpg205163

[0054] TIFF2023156258000040.tif132161

[0055] Here R i2 ~R i7 Each of these is independently, for example, an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group. i8 For example, a chain hydrocarbon group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a group formed by a combination thereof, more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. A41This is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Q 1 and Q 2 This expresses the same meaning as above. Examples of anions represented by formula (IA) include those described in Japanese Patent Publication No. 2010-204646.

[0056] Preferred anions represented by formula (IA) include those represented by formulas (Ia-1) to (Ia-65), respectively. TIFF2023156258000041.tif247165

[0057] TIFF2023156258000042.tif87160

[0058] TIFF2023156258000043.tif137153

[0059] Among these, anions represented by any of the following formulas are preferred: (Ia-1) to (Ia-4), (Ia-7) to (Ia-11), (Ia-14) to (Ia-30), and (Ia-35) to (Ia-55).

[0060] TIFF2023156258000044.tif3182[In formula (IB), m21 represents an integer between 1 and 5, and when m21 is 2 or greater, the bases within the parentheses may be the same or different. R 21 This represents a hydrocarbon group having 3 to 48 carbon atoms, including a cyclic hydrocarbon group having 3 to 18 carbon atoms, and the cyclic hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-. R 22 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and the -CH2- contained in the alkyl group may be replaced with -O- or -CO-. m22 represents an integer between 0 and 4, and when m22 is 2 or greater, multiple R 22They may be identical or different from one another.

[0061] In equation (IB), R 21 Examples of hydrocarbon groups containing cyclic hydrocarbon groups in this context include monocyclic or polycyclic alicyclic hydrocarbon groups and aromatic hydrocarbon groups, or combinations thereof, and groups obtained by arbitrarily combining cyclic hydrocarbon groups such as monocyclic or polycyclic alicyclic hydrocarbon groups and aromatic hydrocarbon groups with chain hydrocarbon groups (alkyl groups, alkenyl groups, alkynyl groups, etc.). 21 The number of carbon atoms in the cyclic hydrocarbon group is, for example, 3 to 24, preferably 3 to 20, more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 5 to 16. 21 The total number of carbon atoms in the hydrocarbon group including the cyclic hydrocarbon group is, for example, 3 to 48, preferably 3 to 40, more preferably 3 to 36, even more preferably 3 to 30, even more preferably 3 to 24, even more preferably 3 to 18, and even more preferably 3 to 16.

[0062] The alicyclic hydrocarbon group may be monocyclic, polycyclic, or spirocyclic, and may be saturated or unsaturated. Examples of alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl groups, and polycyclic cycloalkyl groups such as decahydronaphthyl, norbornyl, and adamantyl groups. Specifically, examples of alicyclic hydrocarbon groups include the groups shown below. The bonding site can be at any position. Specifically, according to TIFF2023156258000045.tif46168, examples of alicyclic hydrocarbon groups include the following groups. * indicates a bonding site. TIFF2023156258000046.tif26150 The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 5 to 16. Examples of aromatic hydrocarbon groups include phenyl groups, naphthyl groups, biphenyl groups, anthryl groups, phenanthryl groups, binaphthyl groups, and other aryl groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10.

[0063] Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl groups. Examples of alkenyl groups include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. Examples of alkynyl groups include ethynyl, propynyl, isopropynyl, butynyl, isobutynyl, tert-butynyl, pentynyl, hexynyl, octinyl, and noninyl groups. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 24, more preferably 1 to 18, even more preferably 1 to 12, even more preferably 1 to 8, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3.

[0064] The combined bases are, Examples include groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, groups combining an alicyclic hydrocarbon group and a chain hydrocarbon group, groups combining an aromatic hydrocarbon group and a chain hydrocarbon group, and groups combining an alicyclic hydrocarbon group, an aromatic hydrocarbon group and a chain hydrocarbon group. Here, the -CH2- contained in the combined group may be replaced with -O-, -S-, -CO-, or -SO2-. Furthermore, in the combinations, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and linear hydrocarbon groups may be combined. Also, any of the groups may be bonded to an oxygen atom. In addition, the above-mentioned groups may include groups with different valencies (alkanediyl groups, alkanetriyl groups, cycloalkanediyl groups, cycloalkanetriyl groups, etc.).

[0065] Specific examples of combined elements include: Alicyclic hydrocarbon groups - chain hydrocarbon groups -* (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-), such as adamantylmethyl group, adamantylethyl group, cyclohexylmethyl group, and cyclohexylethyl group. Chain-type hydrocarbon group - alicyclic hydrocarbon group - * (the -CH2- contained in the chain-type hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), such as methyladamantyl group, methylcyclohexyl group, and dimethylcyclohexyl group. Chain-type hydrocarbon groups such as tolyl groups and xylyl groups - aromatic hydrocarbon groups - * (the -CH2- contained in the chain-type hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), A chain-type hydrocarbon group - alicyclic hydrocarbon group - chain-type hydrocarbon group - * (the -CH2- contained in the chain-type hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-), such as a methylcyclohexylmethyl group. Aromatic hydrocarbon groups such as benzyl groups and phenethyl groups - chain hydrocarbon groups -* (the -CH2- contained in the chain hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-), A chain-like hydrocarbon group such as a tolylmethyl group - aromatic hydrocarbon group - chain-like hydrocarbon group -* (the -CH2- contained in the chain-like hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), Aromatic hydrocarbon groups such as phenyladamantyl groups - alicyclic hydrocarbon groups -* (the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-), A cyclohexylphenyl group, an adamantylphenyl group, or other alicyclic hydrocarbon group - aromatic hydrocarbon group -* (the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-), A chain-type hydrocarbon group - alicyclic hydrocarbon group - aromatic hydrocarbon group - * (the -CH2- contained in the chain-type hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), such as a methylcyclohexylphenyl group or a dimethylcyclohexylphenyl group. A chain-type hydrocarbon group - aromatic hydrocarbon group - alicyclic hydrocarbon group - * (the -CH2- contained in the chain-type hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), such as a methylphenylcyclohexyl group or a dimethylphenylcyclohexyl group. A cyclohexylmethylphenyl group, a cyclohexylethylphenyl group, or other alicyclic hydrocarbon group - a chain hydrocarbon group - an aromatic hydrocarbon group - * (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-). Aromatic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-* (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), such as phenylmethylcyclohexyl group and phenylethylcyclohexyl group. A cyclohexylphenylmethyl group, a cyclohexylphenylethyl group, or other alicyclic hydrocarbon group - aromatic hydrocarbon group - chain hydrocarbon group -* (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-). Aromatic hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-* (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), such as phenylcyclohexylmethyl group and phenylcyclohexylethyl group. These are some examples. Here, * represents the bonding site with the oxygen atom.

[0066] R 21 If the -CH2- contained in the hydrocarbon group represented by is replaced by -O-, -S-, -CO-, or -SO2-, the number of carbon atoms before replacement shall be the total number of carbon atoms in the hydrocarbon group. This number may be one or two or more. Groups in which the -CH2- contained in a hydrocarbon group is replaced with -O-, -S-, -CO-, or -SO2- include: hydroxyl group (a group in which the -CH2- contained in a methyl group is replaced with -O-), thiol group (a group in which the -CH2- contained in a methyl group is replaced with -S-), carboxyl group (a group in which the -CH2-CH2- contained in an ethyl group is replaced with -O-CO-), alkoxy group (a group in which the -CH2- at any position in an alkyl group is replaced with -O-), alkylthio group (a group in which the -CH2- at any position in an alkyl group is replaced with -S-) (A group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), an alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), an oxy group (a group in which -CH2- in a methylene group is replaced with -O-) (a group in which -CH2- in the methylene group is replaced by -CO-), thio group (a group in which -CH2- in the methylene group is replaced by -S-), sulfonyl group (a group in which -CH2- in the methylene group is replaced by -SO2-), alkanediyloxy group (a group in which -CH2- at any position in the alkanediyl group is replaced by -O-), alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in the alkanediyl group is replaced by -O-CO-), alkanediylcarbonyl group (a (A group in which -CH2- at any position in the alkanediyl group is replaced with -CO-), alkanediylcarbonyloxy group (A group in which -CH2-CH2- at any position in the alkanediyl group is replaced with -CO-O-), alkanediylthio group (A group in which -CH2- at any position in the alkanediyl group is replaced with -S-), alkanediylsulfonyl group (A group in which -CH2- at any position in the alkanediyl group is replaced with -SO2-), cycloalkoxy group, cycloalkylalkoxy group, alkoxycarbonyloxy group,Examples include aromatic hydrocarbon group-carbonyloxy group, aromatic hydrocarbon group-carbonyl group, aromatic hydrocarbon group-oxy group, and groups combining two or more of these groups. Examples of alkoxy groups include alkoxy groups having 1 to 17 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, and undecyloxy groups. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkylthio groups include alkylthio groups having 1 to 17 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, and undecylthio group. The number of carbon atoms in the alkylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Alkoxycarbonyl groups, alkylcarbonyl groups, and alkylcarbonyloxy groups represent groups in which a carbonyl group or carbonyloxy group is bonded to an alkyl group or alkoxy group as described above. Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 17 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl groups. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 18 carbon atoms, such as acetyl, propionyl, and butyryl groups. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 17 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy groups. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of alkylsulfonyl groups include alkylsulfonyl groups having 1 to 17 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, octylsulfonyl group, 2-ethylhexylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, and undecylsulfonyl group. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediyloxy groups include alkanediyloxy groups having 1 to 17 carbon atoms, such as methyleneoxy, ethyleneoxy, propanediyloxy, butanediyloxy, and pentanediyloxy groups. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediyloxycarbonyl groups include alkanediyloxycarbonyl groups having 2 to 17 carbon atoms, such as methyleneoxycarbonyl groups, ethyleneoxycarbonyl groups, propanediyloxycarbonyl groups, and butanediyloxycarbonyl groups. Examples of alkanediylcarbonyl groups include alkanediylcarbonyl groups having 2 to 18 carbon atoms, such as methylenecarbonyl groups, ethylenecarbonyl groups, propanediylcarbonyl groups, butanediylcarbonyl groups, and pentanediylcarbonyl groups. Examples of alkanediylcarbonyloxy groups include alkanediylcarbonyloxy groups having 2 to 17 carbon atoms, such as methylenecarbonyloxy groups, ethylenecarbonyloxy groups, propanediylcarbonyloxy groups, and butanediylcarbonyloxy groups. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of alkanediylthio groups include alkanediylthio groups having 1 to 17 carbon atoms, such as methylenethio groups, ethylenethio groups, and propylenethio groups. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediylsulfonyl groups include alkanediylsulfonyl groups having 1 to 17 carbon atoms, such as methylenesulfonyl groups, ethylenesulfonyl groups, and propylenesulfonyl groups. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 17 carbon atoms, such as the cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as the cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as the butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 17 carbon atoms, such as the benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 18 carbon atoms, such as the benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 17 carbon atoms, such as the phenyloxy group. Furthermore, groups in which the -CH2- contained in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO-, or -SO2- include the groups shown below. The -O- or -CO- in the groups shown below may be replaced with -S- or -SO2-. The bonding site can be at any position. Specifically, according to TIFF2023156258000047.tif46169, groups in which the -CH2- contained in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO-, or -SO2- include the following groups. * indicates a bonding site. TIFF2023156258000048.tif54153

[0067] Substituents that a cyclic hydrocarbon group may have include halogen atoms, cyano groups, and C1-C12 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO-, or -SO2-). When a cyclic hydrocarbon group has substituents, the substituents are R 21 It is not included in the total number of carbon atoms of hydrocarbon groups containing cyclic hydrocarbon groups. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. Examples of alkyl groups having 1 to 12 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, and nonyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 9, even more preferably 1 to 8, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. If a substituent is found in an alkyl group, and the -CH2- is replaced with -O-, -S-, -CO-, or -SO2-, the number of carbon atoms before replacement shall be the total number of carbon atoms in the alkyl group. Examples of replaced groups include hydroxyl groups (groups in which the -CH2- contained in a methyl group is replaced with -O-), carboxyl groups (groups in which the -CH2-CH2- contained in an ethyl group is replaced with -O-CO-), alkoxy groups (groups in which -CH2- at any position in an alkyl group is replaced with -O-), alkoxycarbonyl groups (groups in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), alkylcarbonyl groups (groups in which the -CH2- at any position in an alkyl group is replaced with -CO-), alkylcarbonyloxy groups (groups in which the -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), and groups that combine two or more of these groups. Examples of alkoxy groups include alkoxy groups having 1 to 11 carbon atoms. For example, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, and undecyloxy groups are examples. The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. Alkoxycarbonyl groups, alkylcarbonyl groups, and alkylcarbonyloxy groups represent groups in which a carbonyl group or carbonyloxy group is bonded to an alkyl group or alkoxy group as described above. Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 11 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl groups. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 12 carbon atoms, such as acetyl, propionyl, and butyryl groups. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 11 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy groups. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3. The cyclic hydrocarbon group may have one substituent or more substituents. The substituents that the cyclic hydrocarbon group may have are preferably halogen atoms or C1-C6 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO-, or -SO2-), more preferably fluorine atoms, iodine atoms, or C1-C4 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO-, or -SO2-), even more preferably fluorine atoms, iodine atoms, hydroxyl groups, C1-C3 alkoxy groups, or C1-C4 alkyl groups, and even more preferably fluorine atoms, iodine atoms, hydroxyl groups, or C1-C4 alkyl groups.

[0068] A cyclic hydrocarbon group (the cyclic hydrocarbon group may have substituents, and the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-) is Preferably, it is an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have substituents, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms (the aromatic hydrocarbon group may have substituents). It is more preferable that the alicyclic hydrocarbon group has 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have one or more elements selected from the group consisting of alkyl groups, hydroxyl groups, iodine atoms, and fluorine atoms having 1 to 4 carbon atoms, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), or that the aromatic hydrocarbon group has 6 to 18 carbon atoms (the aromatic hydrocarbon group may have one or more elements selected from the group consisting of alkyl groups, hydroxyl groups, iodine atoms, and fluorine atoms having 1 to 4 carbon atoms), It is even more preferable that the alicyclic hydrocarbon group has 5 to 16 carbon atoms (the alicyclic hydrocarbon group may have one or more atoms selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an iodine atom, and a fluorine atom, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-).

[0069] R 21 A hydrocarbon group having 3 to 48 carbon atoms that includes a cyclic hydrocarbon group represented by (the cyclic hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-) is: Preferably, a hydrocarbon group having 3 to 48 carbon atoms including an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), or a hydrocarbon group having 6 to 48 carbon atoms including an aromatic hydrocarbon group having 6 to 18 carbon atoms (the aromatic hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), More preferably, a hydrocarbon group having 3 to 48 carbon atoms including an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have one or more elements selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an iodine atom, and a fluorine atom, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), or a hydrocarbon group having 6 to 48 carbon atoms including an aromatic hydrocarbon group having 6 to 18 carbon atoms (the aromatic hydrocarbon group may have one or more elements selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an iodine atom, and a fluorine atom, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), More preferably, a cycloaliphatic hydrocarbon group having 3 to 18 carbon atoms (the cycloaliphatic hydrocarbon group may have one or more elements selected from the group consisting of alkyl groups, hydroxyl groups, iodine atoms, and fluorine atoms having 1 to 4 carbon atoms, and the -CH2- contained in the cycloaliphatic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), or a group combining a cycloaliphatic hydrocarbon group having 3 to 18 carbon atoms and a chain hydrocarbon group having 1 to 6 carbon atoms (the cycloaliphatic hydrocarbon group may have one or more elements selected from the group consisting of alkyl groups, hydroxyl groups, iodine atoms, and fluorine atoms having 1 to 4 carbon atoms, and the -CH2- contained in the combined group may be replaced with -O-, -S -, -SO2- or -CO- may be replaced by -, -SO2- or -CO-), a C6- to C18 aromatic hydrocarbon group (the aromatic hydrocarbon group may have one or more selected from the group consisting of C1- to C4 alkyl groups, hydroxyl groups, iodine atoms and fluorine atoms), or a group combining a C6- to C18 aromatic hydrocarbon group and a C1- to C6 chain hydrocarbon group (the aromatic hydrocarbon group may have one or more selected from the group consisting of C1- to C4 alkyl groups, hydroxyl groups, iodine atoms and fluorine atoms, and the -CH2- contained in the combined group may be replaced by -O-, -S-, -SO2- or -CO-), More preferably, the group is an alicyclic hydrocarbon group having 5 to 16 carbon atoms (the alicyclic hydrocarbon group may have one or more elements selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an iodine atom, and a fluorine atom, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), or a group formed by combining an alicyclic hydrocarbon group having 5 to 16 carbon atoms and a chain hydrocarbon group having 1 to 4 carbon atoms (the alicyclic hydrocarbon group may have one or more elements selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an iodine atom, and a fluorine atom, and the -CH2- contained in the combined group may be replaced with -O-, -S-, -SO2-, or -CO-). Also, R 21 A hydrocarbon group having 3 to 48 carbon atoms that includes a cyclic hydrocarbon group represented by (the cyclic hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-) is: W 21 -L 21 -*(W 21 L represents a cyclic hydrocarbon group having 3 to 18 carbon atoms, which may have substituents, and the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-. 21 represents a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms, and the -CH2- contained in the chain hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-. * represents a bonding site with an oxygen atom. ) is also preferable. W 21 The cyclic hydrocarbon group, W 21 A substituent that L may have, 21 Examples of chain-like hydrocarbon groups include those similar to those described above. W 21It is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have substituents, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms (the aromatic hydrocarbon group may have substituents), and it is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have one or more selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, hydroxyl groups, iodine atoms and fluorine atoms, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or It is more preferable that the -CH2- is replaced by -O-, -S-, -SO2-, or -CO-, (the -CH2- may be replaced by -CO-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms (the aromatic hydrocarbon group may have one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, an iodine atom, and a fluorine atom), and even more preferable that the -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -S-, -SO2-, or -CO-). L 21 It is preferably a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), more preferably a single bond or a chain hydrocarbon group having 1 to 4 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), and even more preferably a single bond or a chain hydrocarbon group having 1 to 3 carbon atoms. m21 is an integer from 1 to 5, preferably an integer from 1 to 4, more preferably an integer from 1 to 3, even more preferably 1 or 2, and even more preferably 2. When m21 is 1 or 2, SO3 - For this purpose, the following structure, which is an m substitution, is preferable. In the above formula, R 21’ This is the R mentioned above. 21 This is the same definition as R21 It may be the same as or different from it.

[0070] R 22 Examples of alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, and hexyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 4, and more preferably 1 to 3. R 22 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. R 22 Each of these is preferably independently a halogen atom or a C1-C4 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), more preferably a fluorine atom, an iodine atom, or a C1-C3 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a hydroxyl group, a methoxy group, or a methyl group. m22 is an integer from 0 to 4, preferably an integer from 0 to 3, and more preferably an integer from 0 to 2. In one embodiment, it is preferable that m22 is 0. In another embodiment, it is preferable that m22 is 1 or 2. When m22 is 1, R 22 It is preferable that R is a halogen atom, 22 It is more preferable that it is a fluorine atom or an iodine atom. When m22 is 2, R 22 Preferably, one of them is a halogen atom, and the other is a halogen atom or an alkyl group having 1 to 4 carbon atoms, R 22 It is more preferable that one of the atoms is a fluorine atom or an iodine atom, and the other atom is a fluorine atom, an iodine atom, or an alkyl group having 1 to 3 carbon atoms.

[0071] Examples of anions (IB) include the following. Among these, anions represented by formulas (IB-1) to (IB-20) are preferred, and anions represented by formulas (IB-1) to (IB-11) and (IB-16) to (IB-20) are more preferred. TIFF2023156258000050.tif163160

[0072] AI - Examples of sulfonylimid anions represented by the formula include the following: Examples of sulfonylmethide anions include the following: TIFF2023156258000052.tif26132

[0073] Examples of salt(I) include salts formed by arbitrarily combining the cations and anions mentioned above. Specific examples of salt(I) are shown in the table below. In the table below, each symbol represents the symbol attached to the structure representing the anion or cation described above, and "~" indicates that salt (I) corresponds to either anion (I) or cation (I). For example, salt (I-1) is a salt consisting of the anion shown in formula (Ia-1) and the cation shown in formula (Ic-1), salt (I-2) is a salt consisting of the anion shown in formula (Ia-2) and the cation shown in formula (Ic-1), and salt (I-39) is a salt consisting of the anion shown in formula (Ia-1) and the cation shown in formula (Ic-2). TIFF2023156258000053.tif5687 [Table 1] TIFF2023156258000055.tif229154 TIFF2023156258000056.tif203152

[0074] In particular, salt (I) is preferably a salt formed by combining an anion represented by any of the formulas (Ia-1) to (Ia-4), (Ia-7) to (Ia-11), (Ia-14) to (Ia-30), (Ia-35) to (Ia-55), and (IB-1) to (IB-20) with a cation represented by any of the formulas (Ic-1) to (Ic-90). Specifically, salts (I-1) to (I-4), salts (I-7) to (I-11), salts (I-14) to (I-30), salts (I-35) to (I-38), salts (I-39) to (I-42), and salts (I-45) ~Salt (I-49), Salt (I-52)~Salt (I-68), Salt (I-73)~Salt (I-76), Salt (I-77)~Salt (I-80), Salt (I-83)~Salt (I-87), Salt (I-90)~Salt (I-106), Salt (I-111)~Salt (I-114), Salt (I-115)~Salt (I-11 8) Salt (I-121) ~ Salt (I-125), Salt (I-128) ~ Salt (I-144), Salt (I-149) ~ Salt (I-152), Salt (I-153) ~ Salt (I-156), Salt (I-159) ~ Salt (I-163), Salt (I-166) ~ Salt (I-182), Salt (I-187) ~ Salt (I -190), Salt (I-191)~Salt (I-194), Salt (I-197)~Salt (I-201), Salt (I-204)~Salt (I-220), Salt (I-225)~Salt (I-228), Salt (I-229)~Salt (I-232), Salt (I-235)~Salt (I-239), Salt (I-242)~ Salt (I-258), Salt (I-263)~Salt (I-266), Salt (I-267)~Salt (I-270), Salt (I-273)~Salt (I-277), Salt (I-280)~Salt (I-296), Salt (I-301)~Salt (I-304), Salt (I-305)~Salt (I-308), Salt (I-31 1) Salt (I-315), Salt (I-318), Salt (I-334), Salt (I-339), Salt (I-342), Salt (I-343), Salt (I-346), Salt (I-349), Salt (I-353), Salt (I-356), Salt (I-372), Salt (I-377), Salt (I-380), Salt (I -381)~Salt (I-384), Salt (I-387)~Salt (I-391), Salt (I-394)~Salt (I-410), Salt (I-415)~Salt (I-418), Salt (I-419)~Salt (I-422), Salt (I-425)~Salt (I-429), Salt (I-432)~Salt (I-448),Salt (I-453) ~ Salt (I-456), Salt (I-457) ~ Salt (I-460), Salt (I-463) ~ Salt (I-467), Salt (I-470) ~ Salt (I-486), Salt (I-491) ~ Salt (I-494), Salt (I-495) ~ Salt (I-498), Salt (I-501) ~ Salt (I-50 5) Salt (I-508) ~ Salt (I-524), Salt (I-529) ~ Salt (I-532), Salt (I-533) ~ Salt (I-536), Salt (I-539) ~ Salt (I-543), Salt (I-546) ~ Salt (I-562), Salt (I-567) ~ Salt (I-570), Salt (I-571) ~ Salt (I- 574), Salt (I-577)~Salt (I-581), Salt (I-584)~Salt (I-600), Salt (I-605)~Salt (I-608), Salt (I-609)~Salt (I-612), Salt (I-615)~Salt (I-619), Salt (I-622)~Salt (I-638), Salt (I-643)~Salt ( I-646), Salt (I-647)~Salt (I-650), Salt (I-653)~Salt (I-657), Salt (I-660)~Salt (I-676), Salt (I-681)~Salt (I-684), Salt (I-685)~Salt (I-688), Salt (I-691)~Salt (I-695), Salt (I-698)~ Salt (I-714), Salt (I-719)~Salt (I-722), Salt (I-723)~Salt (I-726), Salt (I-729)~Salt (I-733), Salt (I-736)~Salt (I-752), Salt (I-757)~Salt (I-760), Salt (I-761)~Salt (I-764), Salt (I-76 7) ~Salt (I-771), Salt (I-774) ~Salt (I-790), Salt (I-795) ~Salt (I-798), Salt (I-799) ~Salt (I-802), Salt (I-805) ~Salt (I-809), Salt (I-812) ~Salt (I-828), Salt (I-833) ~Salt (I-836), Salt (I- 837)~Salt (I-840), Salt (I-843)~Salt (I-847), Salt (I-850)~Salt (I-866), Salt (I-871)~Salt (I-874), Salt (I-875)~Salt (I-878), Salt (I-881)~Salt (I-885), Salt (I-888)~Salt (I-904), Salt ( I-909)~Salt(I-912), Salt(I-913)~Salt(I-916), Salt(I-919)~Salt(I-923), Salt(I-926)~Salt(I-942), Salt(I-947)~Salt(I-950), Salt(I-951)~Salt(I-954), Salt(I-957)~Salt(I-961),Salt (I-964)~Salt (I-980), Salt (I-985)~Salt (I-988), Salt (I-989)~Salt (I-992), Salt (I-995)~Salt (I-999), Salt (I-1002)~Salt (I-1018), Salt (I-1023)~Salt (I-1026), Salt (I-1027)~Salt ( I-1030), salt (I-1033)~salt (I-1037), salt (I-1040)~salt (I-1056), salt (I-1061)~salt (I-1064), salt (I-1065)~salt (I-1068), salt (I-1071)~salt (I-1075), salt (I-1078)~salt (I-10 94), Salt (I-1099)~Salt (I-1102), Salt (I-1103)~Salt (I-1106), Salt (I-1109)~Salt (I-1113), Salt (I-1116)~Salt (I-1132), Salt (I-1137)~Salt (I-1140), Salt (I-1141)~Salt (I-1144), Salt (I-1147) ~ Salt (I-1151), Salt (I-1154) ~ Salt (I-1170), Salt (I-1175) ~ Salt (I-1178), Salt (I-1179) ~ Salt (I-1182), Salt (I-1185) ~ Salt (I-1189), Salt (I-1192) ~ Salt (I-1208), Salt (I- 1213)~Salt (I-1216), Salt (I-1217)~Salt (I-1220), Salt (I-1223)~Salt (I-1227), Salt (I-1230)~Salt (I-1246), Salt (I-1251)~Salt (I-1254), Salt (I-1255)~Salt (I-1258), Salt (I-1261 )~Salt (I-1265), Salt (I-1268)~Salt (I-1284), Salt (I-1289)~Salt (I-1292), Salt (I-1293)~Salt (I-1296), Salt (I-1299)~Salt (I-1303), Salt (I-1306)~Salt (I-1322), Salt (I-1327)~Salt ( I-1330), salt (I-1331)~salt (I-1334), salt (I-1337)~salt (I-1341), salt (I-1344)~salt (I-1360), salt (I-1365)~salt (I-1368), salt (I-1369)~salt (I-1372), salt (I-1375)~salt (I-13 79), salt (I-1382)~salt (I-1398), salt (I-1403)~salt (I-1406), salt (I-1407)~salt (I-1410), salt (I-1413)~salt (I-1417), salt (I-1420)~salt (I-1436), salt (I-1441)~salt (I-1444),Salt (I-1445) ~ Salt (I-1448), Salt (I-1451) ~ Salt (I-1455), Salt (I-1458) ~ Salt (I-1474), Salt (I-1479) ~ Salt (I-1482), Salt (I-1483) ~ Salt (I-1486), Salt (I-1489) ~ Salt (I-1493), Salt (I-1 496) ~Salt (I-1512), Salt (I-1517)~Salt (I-1520), Salt (I-1521)~Salt (I-1524), Salt (I-1527)~Salt (I-1531), Salt (I-1534)~Salt (I-1550), Salt (I-1555)~Salt (I-1558), Salt (I-1559)~ Salt (I-1562), Salt (I-1565) ~ Salt (I-1569), Salt (I-1572) ~ Salt (I-1588), Salt (I-1593) ~ Salt (I-1596), Salt (I-1597) ~ Salt (I-1600), Salt (I-1603) ~ Salt (I-1607), Salt (I-1610) ~ Salt (I-1 626), salt (I-1631)~salt (I-1634), salt (I-1635)~salt (I-1638), salt (I-1641)~salt (I-1645), salt (I-1648)~salt (I-1664), salt (I-1669)~salt (I-1672), salt (I-1673)~salt (I-1676), Salt (I-1679) ~ Salt (I-1683), Salt (I-1686) ~ Salt (I-1702), Salt (I-1707) ~ Salt (I-1710), Salt (I-1711) ~ Salt (I-1714), Salt (I-1717) ~ Salt (I-1721), Salt (I-1724) ~ Salt (I-1740), Salt (I-1 745)~Salt (I-1748), Salt (I-1749)~Salt (I-1752), Salt (I-1755)~Salt (I-1759), Salt (I-1762)~Salt (I-1778), Salt (I-1783)~Salt (I-1786), Salt (I-1787)~Salt (I-1790), Salt (I-1793)~ Salt (I-1797), Salt (I-1800)~Salt (I-1816), Salt (I-1821)~Salt (I-1824), Salt (I-1825)~Salt (I-1828), Salt (I-1831)~Salt (I-1835), Salt (I-1838)~Salt (I-1854), Salt (I-1859)~Salt (I-1 862), Salt (I-1863)~Salt (I-1866), Salt (I-1869)~Salt (I-1873), Salt (I-1876)~Salt (I-1892), Salt (I-1897)~Salt (I-1900), Salt (I-1901)~Salt (I-1904), Salt (I-1907)~Salt (I-1911),Salt (I-1914) ~ Salt (I-1930), Salt (I-1935) ~ Salt (I-1938), Salt (I-1939) ~ Salt (I-1942), Salt (I-1945) ~ Salt (I-1949), Salt (I-1952) ~ Salt (I-1968), Salt (I-1973) ~ Salt (I-1976), Salt (I-1 977) ~ Salt (I-1980), Salt (I-1983) ~ Salt (I-1987), Salt (I-1990) ~ Salt (I-2006), Salt (I-2011) ~ Salt (I-2014), Salt (I-2015) ~ Salt (I-2018), Salt (I-2021) ~ Salt (I-2025), Salt (I-2028) ~ Salt (I-2044), Salt (I-2049)~Salt (I-2052), Salt (I-2053)~Salt (I-2056), Salt (I-2059)~Salt (I-2063), Salt (I-2066)~Salt (I-2082), Salt (I-2087)~Salt (I-2090), Salt (I-2091)~Salt (I-2 094), salt (I-2097)~salt (I-2101), salt (I-2104)~salt (I-2120), salt (I-2125)~salt (I-2128), salt (I-2121)~salt (I-2094), salt (I-2097)~salt (I-2101), salt (I-2104)~salt (I-2120), Salt (I-2125) ~ Salt (I-2128), Salt (I-2129) ~ Salt (I-2132), Salt (I-2135) ~ Salt (I-2139), Salt (I-2142) ~ Salt (I-2158), Salt (I-2163) ~ Salt (I-2166), Salt (I-2167) ~ Salt (I-2170), Salt (I-2 173) ~Salt (I-2177), Salt (I-2180)~Salt (I-2196), Salt (I-2201)~Salt (I-2204), Salt (I-2205)~Salt (I-2208), Salt (I-2211)~Salt (I-2215), Salt (I-2218)~Salt (I-2234), Salt (I-2239)~ Salt (I-2242), Salt (I-2243) ~ Salt (I-2246), Salt (I-2249) ~ Salt (I-2253), Salt (I-2256) ~ Salt (I-2272), Salt (I-2277) ~ Salt (I-2280), Salt (I-2281) ~ Salt (I-2284), Salt (I-2287) ~ Salt (I-2 291), salt (I-2294)~salt (I-2310), salt (I-2315)~salt (I-2318), salt (I-2319)~salt (I-2322), salt (I-2325)~salt (I-2329), salt (I-2332)~salt (I-2348), salt (I-2353)~salt (I-2356),Salt (I-2357) ~ Salt (I-2360), Salt (I-2363) ~ Salt (I-2367), Salt (I-2370) ~ Salt (I-2386), Salt (I-2391) ~ Salt (I-2394), Salt (I-2395) ~ Salt (I-2398), Salt (I-2401) ~ Salt (I-2405), Salt (I-2408) ~ Salt (I-2424), Salt (, I-2429)~Salt (I-2432), Salt (I-2433)~Salt (I-2436), Salt (I-2439)~Salt (I-2443), Salt (I-2446)~Salt (I-2462), Salt (I-2467)~Salt (I-2470), Salt (I-2471)~Salt (I-2474), Salt (I-24 77) ~Salt (I-2481), Salt (I-2484) ~Salt (I-2500), Salt (I-2505) ~Salt (I-2508), Salt (I-2509) ~Salt (I-2512), Salt (I-2515) ~Salt (I-2519), Salt (I-2522) ~Salt (I-2538), Salt (I-2543) ~Salt (I-2546), salt (I-2547)~salt (I-2550), salt (I-2553)~salt (I-2557), salt (I-2560)~salt (I-2576), salt (I-2581)~salt (I-2584), salt (I-2585)~salt (I-2588), salt (I-2591)~salt (I-25 95), salt (I-2598)~salt (I-2614), salt (I-2619)~salt (I-2622), salt (I-2623)~salt (I-2626), salt (I-2629)~salt (I-2633), salt (I-2636)~salt (I-2652), salt (I-2657)~salt (I-2660), salt (I-2661)~Salt (I-2664), Salt (I-2667)~Salt (I-2671), Salt (I-2674)~Salt (I-2690), Salt (I-2695)~Salt (I-2698), Salt (I-2699)~Salt (I-2702), Salt (I-2705)~Salt (I-2709), Salt (I-2 712) ~Salt (I-2728), Salt (I-2733)~Salt (I-2736), Salt (I-2737)~Salt (I-2740), Salt (I-2743)~Salt (I-2747), Salt (I-2750)~Salt (I-2766), Salt (I-2771)~Salt (I-2774), Salt (I-2775)~ Salt (I-2778), Salt (I-2781)~Salt (I-2785), Salt (I-2788)~Salt (I-2804), Salt (I-2809)~Salt (I-2812), Salt (I-2813)~Salt (I-2816), Salt (I-2819)~Salt (I-2823), Salt (I-2826)~Salt (I-2 842), salt (I-2847)~salt (I-2850), salt (I-2851)~salt (I-2854), salt (I-2857)~salt (I-2861), salt (I-2864)~salt (I-2880), salt (I-2885)~salt (I-2888), salt (I-2889)~salt (I-2892),Salt (I-2895) ~ Salt (I-2899), Salt (I-2902) ~ Salt (I-2918), Salt (I-2923) ~ Salt (I-2926), Salt (I-2927) ~ Salt (I-2930), Salt (I-2933) ~ Salt (I-2937), Salt (I-2940) ~ Salt (I-2956), Salt (I-2 961) ~ Salt (I-2964), Salt (I-2965) ~ Salt (I-2968), Salt (I-2971) ~ Salt (I-2975), Salt (I-2978) ~ Salt (I-2994), Salt (I-2999) ~ Salt (I-3002), Salt (I-3003) ~ Salt (I-3006), Salt (I-3009) ~ Salt (I-3013), Salt (I-3016) ~ Salt (I-3032), Salt (I-3037) ~ Salt (I-3040), Salt (I-3041) ~ Salt (I-3044), Salt (I-3047) ~ Salt (I-3051), Salt (I-3054) ~ Salt (I-3070), Salt (I-3075) ~ Salt (I-3 078), salt (I-3079)~salt (I-3082), salt (I-3085)~salt (I-3089), salt (I-3092)~salt (I-3108), salt (I-3113)~salt (I-3116), salt (I-3117)~salt (I-3120), salt (I-3123)~salt (I-3127), Salt (I-3130) ~ Salt (I-3146), Salt (I-3151) ~ Salt (I-3154), Salt (I-3155) ~ Salt (I-3158), Salt (I-3161) ~ Salt (I-3165), Salt (I-3168) ~ Salt (I-3184), Salt (I-3189) ~ Salt (I-3192), Salt (I-3 193) ~Salt (I-3196), Salt (I-3199)~Salt (I-3203), Salt (I-3206)~Salt (I-3222), Salt (I-3227)~Salt (I-3230), Salt (I-3231)~Salt (I-3234), Salt (I-3237)~Salt (I-3241), Salt (I-3244)~ Salt (I-3260), Salt (I-3265) ~ Salt (I-3268), Salt (I-3269) ~ Salt (I-3272), Salt (I-3275) ~ Salt (I-3279), Salt (I-3282) ~ Salt (I-3298), Salt (I-3303) ~ Salt (I-3306), Salt (I-3307) ~ Salt (I-3 310), salt (I-3313)~salt (I-3317), salt (I-3320)~salt (I-3336), salt (I-3341)~salt (I-3344), salt (I-3345)~salt (I-3348), salt (I-3351)~salt (I-3355), salt (I-3358)~salt (I-3374),It is preferable that the salts are salt(I-3379)~salt(I-3382), salt(I-3383)~salt(I-3386), salt(I-3389)~salt(I-3393), salt(I-3396)~salt(I-3412), salt(I-3417)~salt(I-5670), and salt(I-5671)~salt(I-6750).

[0075] <Method for producing salt (I)> Salt (I) can be produced by reacting the salt represented by formula (Ia) with the salt represented by formula (Ib) in a solvent. TIFF2023156258000057.tif120161[where, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , m1, m2, m3, m4, m5, m6, m7, m8, m9, A 1 , A 2 , A 3 AI - These terms express the same meaning as described above. R A , R B and R C Each of these independently represents a hydrocarbon group having 1 to 12 carbon atoms, or R A , R B and R C They may come together to form an aromatic ring. D [This represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms.] Examples of solvents include chloroform, monochlorobenzene, acetonitrile, and water. The reaction temperature is typically between 15°C and 80°C, and the reaction time is typically between 0.5 and 24 hours.

[0076] Examples of salts represented by formula (Ib) include those represented by the following formula. These salts can be easily produced by methods similar to those described in Japanese Patent Publication No. 2011-116747 and Japanese Patent Publication No. 2016-047815, or by known manufacturing methods. TIFF2023156258000058.tif168163

[0077] The salt represented by formula (Ia) can be produced by reacting the salt represented by formula (Ic) with the compound represented by formula (I-d1), the compound represented by formula (I-d2), and the compound represented by formula (I-d3) in a solvent in the presence of a catalyst. TIFF2023156258000059.tif148156[In this formula, all symbols have the same meaning as described above.] Examples of catalysts include sodium hydride and potassium carbonate. Examples of solvents include chloroform, monochlorobenzene, acetonitrile, and water. The reaction temperature is typically between 15°C and 100°C, and the reaction time is typically between 0.5 and 24 hours.

[0078] Examples of salts represented by formula (Ic) include those represented by the following formula, and are readily available from the market. TIFF2023156258000060.tif36168

[0079] Examples of compounds represented by formula (I-d1), formula (I-d2), and formula (I-d3) include the following compounds, which are readily available from the market. TIFF2023156258000061.tif54155

[0080] The salt represented by formula (Ia) can also be produced by reacting the compound represented by formula (I-d1), the compound represented by formula (I-d2), and the compound represented by formula (I-d3) with carbonyldiimidazole in a solvent, and then further reacting them with the salt represented by formula (Ie). TIFF2023156258000062.tif115163[In this formula, all signs have the same meaning as defined above.] Examples of solvents include chloroform, monochlorobenzene, and acetonitrile. The reaction temperature is typically between 15°C and 80°C, and the reaction time is typically between 0.5 and 24 hours.

[0081] Examples of salts represented by formula (Ie) include those represented by the following formula, and they are readily available on the market. TIFF2023156258000063.tif36135

[0082] <Acid Generator> The acid generator of the present invention is an acid generator containing salt(I). It may contain one type of salt(I) or two or more types of salt(I). The acid generator of the present invention may contain, in addition to salt (I), an acid generator known in the resist field (hereinafter sometimes referred to as "acid generator (B)"). Acid generator (B) may be used alone or in combination of two or more types.

[0083] The acid generator (B) may be either nonionic or ionic. Examples of nonionic acid generators include sulfonate esters (e.g., 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxiimide, sulfonyloxyketone, diazonaphthoquinone 4-sulfonate) and sulfones (e.g., disulfone, ketosulfone, sulfonyldiazomethane). Typical ionic acid generators include onium salts containing onium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts, iodonium salts). Examples of onium salt anions include sulfonic acid anions, sulfonylimide anions, and sulfonylmethide anions.

[0084] As the acid generator (B), compounds that generate acid by radiation as described in Japanese Patent Publication Nos. 63-26653, 55-164824, 62-69263, 63-146038, 63-163452, 62-153853, 63-146029, U.S. Patent Nos. 3,779,778 and 3,849,137, German Patent No. 3914407, European Patent No. 126,712, etc., can be used. Compounds manufactured by known methods may also be used. Two or more types of acid generators (B) may be used in combination.

[0085] The acid generator (B) is preferably a salt represented by formula (B1) (hereinafter sometimes referred to as "acid generator (B1)," excluding salt (I)) or a salt represented by formula (B2) (hereinafter sometimes referred to as "acid generator (B2)," excluding salt (I)). TIFF2023156258000064.tif2962[In formula (B1), Q b1 and Q b2 Each of these independently represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms. L b1 This represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, where the -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxyl groups. Y represents a methyl group which may have substituents or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-. Z1 + This represents an organic cation.

[0086] Q in equation (B1) b1 Q b2 , L b1 And Y are the same as Q in equation (IA) above. 1 Q 2 , L1 and Y 1 Similar examples can be given. Examples of sulfonic acid anions in formula (B1) include those similar to the anions represented by formula (IA).

[0087] TIFF2023156258000065.tif3190[In formula (B2), m21 represents an integer between 1 and 5, and when m21 is 2 or greater, the bases within the parentheses may be the same or different. R 21 This represents a hydrocarbon group having 3 to 48 carbon atoms, including a cyclic hydrocarbon group having 3 to 18 carbon atoms, and the cyclic hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-. R 22 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and the -CH2- contained in the alkyl group may be replaced with -O- or -CO-. m22 represents an integer between 0 and 4, and when m22 is 2 or greater, multiple R 22 They may be identical or different from one another. Z1 + This represents an organic cation.

[0088] In equation (B2), m21, m22, R 21 and R 22 These are m21, m22, and R in the above-mentioned equation (IB), respectively. 21 and R 22 Similar examples can be given. Examples of sulfonic acid anions in formula (B2) include those similar to the anions represented by formula (IB).

[0089] Z1 +Examples of organic cations include organic onium cations, organic sulfonium cations, organic iodonium cations, organic ammonium cations, benzothiazolium cations, and organic phosphonium cations. Among these, organic sulfonium cations and organic iodonium cations are preferred, and aryl sulfonium cations are more preferred. Specifically, examples include cations represented by any of formulas (b2-1) to (b2-4) (hereinafter, depending on the formula number, they may be referred to as "cation (b2-1)," etc.).

[0090] TIFF2023156258000066.tif46170[Formula (b2-1) to (b2-4), R b4 ~R b6 Each of these independently represents a chain hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms. The hydrogen atoms in the chain hydrocarbon group may be substituted with a hydroxyl group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. The hydrogen atoms in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a glycidyloxy group. The hydrogen atoms in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxyl group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkyl fluoride group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b4 and R b5 These atoms may bond with each other and form a ring together with the sulfur atom to which they are bonded, and the -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R b7 and R b8 Each of these independently represents a halogen atom, a hydroxyl group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. m2 and n2 each independently represent an integer between 0 and 5. When m2 is 2 or more, multiple R b7 They may be the same or different, and when n2 is 2 or greater, multiple R b8 They may be the same or different. R b9 and R b10 Each of these independently represents either a chain-like hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 These atoms may bond with each other and form a ring together with the sulfur atom to which they are bonded, and the -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R b11 This represents a hydrogen atom, a chain hydrocarbon group having 1 to 36 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. R b12 This represents a chain hydrocarbon group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. The hydrogen atoms contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, and the hydrogen atoms contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 12 carbon atoms or an alkylcarbonyloxy group having 1 to 12 carbon atoms. R b11 and R b12 These may be bonded to each other and form a ring including the -CH-CO- groups to which they are bonded, and the -CH2- groups included in the ring may be replaced by -O-, -S-, or -CO-. R b13 ~R b18 Each of these independently represents a halogen atom, a hydroxyl group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b13 and R b14 These atoms may bond with each other and together with the benzene ring to which they are bonded, form a ring containing a sulfur atom, and the -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. L b31 This represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent an integer between 0 and 5. q2 and r2 each independently represent an integer between 0 and 4. u2 represents either 0 or 1. When o2 is 2 or more, multiple R b13 They are the same or different, and when p2 is 2 or more, multiple R b14 They are the same or different, and when q2 is 2 or more, multiple R b15 They are the same or different, and when r2 is 2 or more, multiple R b16 They are the same or different, and when s2 is 2 or more, multiple R b17 They are the same or different, and when t2 is 2 or more, multiple R b18 They are either identical or different. When u2 is 0, then at least one of o2, p2, q2, and r2 is 1 or greater, and R b13 ~R b16 Preferably, at least one of them is a halogen atom, and when u2 is 1, then one of o2, p2, s2, t2, q2 and r2 is 1 or more, and R b13 ~R b18 Preferably, at least one of them is a halogen atom. Furthermore, when u2 is 0, r2 is preferably 1 or greater, and more preferably 1. Also, when u2 is 0 and r2 is 1 or greater, R b16 It is preferable that the atom is a halogen atom. Aliphatic hydrocarbon groups refer to both chain-type hydrocarbon groups and alicyclic hydrocarbon groups. Examples of chain-type hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl. In particular, R b9 ~R b12 The chain-like hydrocarbon group preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, norbornyl, and the following groups. TIFF2023156258000067.tif10158 In particular, R b9 ~R b12 The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 4 to 12 carbon atoms. Examples of alicyclic hydrocarbon groups in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include methylcyclohexyl group, dimethylcyclohexyl group, 2-methyladamantan-2-yl group, 2-ethyladamantan-2-yl group, 2-isopropyladamantan-2-yl group, methylnorbornyl group, and isobornyl group. In alicyclic hydrocarbon groups in which a hydrogen atom is substituted with an aliphatic hydrocarbon group, the total number of carbon atoms in the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 20 or less. A fluorinated alkyl group refers to an alkyl group having 1 to 12 carbon atoms and containing a fluorine atom, such as a fluoromethyl group, difluoromethyl group, trifluoromethyl group, or perfluorobutyl group. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 9, more preferably 1 to 6, and even more preferably 1 to 4.

[0091] Examples of aromatic hydrocarbon groups include aryl groups such as phenyl, biphenyl, naphthyl, and phenanthryl groups. Aromatic hydrocarbon groups may have a chain-like hydrocarbon group or an alicyclic hydrocarbon group, and examples include aromatic hydrocarbon groups having a chain-like hydrocarbon group with 1 to 18 carbon atoms (tolyl, xylyl, cumenyl, mesityl, p-ethylphenyl, p-tert-butylphenyl, 2,6-diethylphenyl, 2-methyl-6-ethylphenyl, etc.) and aromatic hydrocarbon groups having an alicyclic hydrocarbon group with 3 to 18 carbon atoms (p-cyclohexylphenyl, p-adamantylphenyl, etc.). When the aromatic hydrocarbon group has a chain-like hydrocarbon group or an alicyclic hydrocarbon group, chain-like hydrocarbon groups with 1 to 18 carbon atoms and alicyclic hydrocarbon groups with 3 to 18 carbon atoms are preferred. Examples of aromatic hydrocarbon groups in which a hydrogen atom is substituted with an alkoxy group include the p-methoxyphenyl group. Examples of chain-like hydrocarbon groups in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as benzyl, phenethyl, phenylpropyl, trityl, naphthylmethyl, and naphthylethyl groups. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, and dodecyloxy groups. Examples of alkylcarbonyl groups include acetyl, propionyl, and butyryl groups. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. Examples of alkylcarbonyloxy groups include methylcarbonyloxy group, ethylcarbonyloxy group, propylcarbonyloxy group, isopropylcarbonyloxy group, butylcarbonyloxy group, sec-butylcarbonyloxy group, tert-butylcarbonyloxy group, pentylcarbonyloxy group, hexylcarbonyloxy group, octylcarbonyloxy group, and 2-ethylhexylcarbonyloxy group. R b4 and R b5The ring formed by the bonding of these atoms to each other and the sulfur atoms to which they are bonded may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. Examples of such rings include those with 3 to 18 carbon atoms, preferably those with 4 to 18 carbon atoms. Furthermore, examples of sulfur atom-containing rings include those with 3 to 12 membered rings, preferably those with 3 to 7 membered rings, and the following rings are examples. * indicates a bonding site. TIFF2023156258000068.tif23143R b9 and R b10 The ring formed by the combination of these elements may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. This ring may be a 3-membered to 12-membered ring, preferably a 3-membered to 7-membered ring. Examples include a thiolan-1-ium ring (tetrahydrothiophenium ring), a thian-1-ium ring, and a 1,4-oxatian-4-ium ring. R b11 and R b12 The ring formed by the combination of these elements may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. This ring may be a 3-membered to 12-membered ring, preferably a 3-membered to 7-membered ring. Examples include oxocycloheptane rings, oxocyclohexane rings, oxonorbornane rings, and oxoadamantane rings.

[0092] Among cations (b2-1) to (b2-4), cation (b2-1) is preferred. The following cations can be considered as cations (b2-1): TIFF2023156258000069.tif161163 The following cations can be listed as cations (b2-2). TIFF2023156258000070.tif18150 The following cations can be considered as cations (b2-3): TIFF2023156258000071.tif24126 TIFF2023156258000072.tif153163

[0093] The acid generator (B) is a combination of the anion and the organic cation described above, and these can be combined arbitrarily. Preferred examples of the acid generator (B) include a combination of an anion represented by any of the formulas (Ia-1) to (Ia-4), (Ia-7) to (Ia-11), (Ia-14) to (Ia-30), and (Ia-35) to (Ia-55), and (IB-1) to (IB-20), and a cation (b2-1), cation (b2-2), cation (b2-3), or cation (b2-4).

[0094] Preferably, the acid generator (B) is represented by formulas (B1-1) to (B1-105) and formulas (B2-1) to (B2-20), respectively. Among these, those containing arylsulfonium cations are preferred, and those represented by formulas (B1-1) to (B1-3), (B1-5) to (B1-7), (B1-11) to (B1-14), (B1-20) to (B1-26), (B1-29), (B1-31) to (B1-72), and (B2-1) to (B2-20) are particularly preferred. TIFF2023156258000073.tif248168

[0095] TIFF2023156258000074.tif243160

[0096] JPEG2023156258000075.jpg255166

[0097] TIFF2023156258000076.tif248163

[0098] TIFF2023156258000077.tif233163

[0099] TIFF2023156258000078.tif228168

[0100] When the acid generator contains salt (I) and acid generator (B), the ratio of the content of salt (I) to acid generator (B) (mass ratio; salt (I): acid generator (B)) is usually 1:99 to 99:1, preferably 2:98 to 98:2, more preferably 5:95 to 95:5, even more preferably 10:90 to 90:10, and particularly preferably 15:85 to 85:15.

[0101] <Resist Composition> The resist composition of the present invention contains an acid generator comprising salt (I) of the present invention. Preferably, the resist composition of the present invention further contains a resin (hereinafter sometimes referred to as "resin (A)") which contains a structural unit having an acid-unstable group. Here, "acid-unstable group" means a group that has a leaving group, and upon contact with an acid, the leaving group is removed, converting the structural unit into a structural unit having a hydrophilic group (for example, a hydroxyl group or a carboxyl group). The resist composition of the present invention preferably contains a quencher (hereinafter sometimes referred to as "quencher (C)") such as a salt that generates an acid with a lower acidity than the acid generated from the acid generator, and preferably contains a solvent (hereinafter sometimes referred to as "solvent (E)").

[0102] <Acid Generator> In the resist composition of the present invention, the total content of the acid generator is preferably 1% by mass or more and 45% by mass or less, more preferably 1% by mass or more and 40% by mass or less, and even more preferably 3% by mass or more and 35% by mass or less, relative to the solid content of the resist composition. Furthermore, the content of the acid generator is preferably 1 part by mass or more and 45 parts by mass or less, more preferably 1 part by mass or more and 40 parts by mass or less, and even more preferably 3 parts by mass or more and 40 parts by mass or less, relative to 100 parts by mass of the resin (A) described later.

[0103] <Resin (A)> Resin (A) contains structural units having acid-unstable groups (hereinafter sometimes referred to as "structural unit (a1)"). Preferably, resin (A) further contains structural units other than structural unit (a1). Examples of structural units other than structural unit (a1) include structural units that do not have acid-unstable groups (hereinafter sometimes referred to as "structural unit (s)"), structural units other than structural unit (a1) and structural unit (s) (for example, structural units having halogen atoms as described later (hereinafter sometimes referred to as "structural unit (a4)"), structural units having non-eliminating hydrocarbon groups as described later (hereinafter sometimes referred to as "structural unit (a5)"), and structural units derived from other monomers known in the art.

[0104] <Structural unit (a1)> The structural unit (a1) is derived from a monomer having an acid-unstable group (hereinafter sometimes referred to as "monomer (a1)"). The acid-unstable group contained in resin (A) is preferably the group represented by formula (1) (hereinafter also referred to as group (1)) and / or the group represented by formula (2) (hereinafter also referred to as group (2)). TIFF2023156258000079.tif2298[In formula (1), R a1 , R a2 and R a3 Each of these independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. a1 and R a2 These atoms bond with each other to form alicyclic hydrocarbon groups with 3 to 20 carbon atoms, along with the carbon atoms to which they are bonded. ma and na each independently represent either 0 or 1, and at least one of ma and na represents 1. * indicates a connection site. TIFF2023156258000080.tif2278[In formula (2), R a1’ and R a2’ Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R a3’ R represents a hydrocarbon group with 1 to 20 carbon atoms. a2’ and R a3’These atoms bond to each other, forming a heterocyclic group having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded and X. The -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced with -O- or -S-. X represents either an oxygen atom or a sulfur atom. 'na' represents either 0 or 1. * indicates a connection site.

[0105] R a1 , R a2 and R a3 Examples of alkyl groups in this context include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl groups. R a1 , R a2 and R a3 Examples of alkenyl groups in this context include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. R a1 , R a2 and R a3 The alicyclic hydrocarbon group in may be monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, norbornyl, and the following groups (* indicates a bonding site). a1 , R a2 and R a3 The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16. TIFF2023156258000081.tif10159R a1 , R a2 and R a3 Examples of aromatic hydrocarbon groups in this context include aryl groups such as phenyl, naphthyl, anthryl, biphenyl, and phenanthryl groups. Examples of combined groups include groups that combine alkyl groups and alicyclic hydrocarbon groups as described above (for example, alkylcycloalkyl groups or cycloalkylalkyl groups such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having alkyl groups (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), aromatic hydrocarbon groups having alicyclic hydrocarbon groups (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), and aryl-cycloalkyl groups such as phenylcyclohexyl group. Preferably, ma is 0 and na is 1. R a1 and R a2 -C(R a1 )(R a2 )(R a3 Examples of such groups include the following: Alicyclic hydrocarbon groups preferably have 3 to 12 carbon atoms. * indicates a bond site with -O-. TIFF2023156258000082.tif35157

[0106] R a1’ , R a2’ and R a3’ Examples of hydrocarbon groups in this context include alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. Alkyl and alicyclic hydrocarbon groups are R a1 , R a2 and R a3 The same types of elements mentioned above can be cited. Examples of aromatic hydrocarbon groups include phenyl groups, naphthyl groups, anthryl groups, biphenyl groups, phenanthryl groups, and other aryl groups. Examples of combined groups include groups that combine alkyl groups and alicyclic hydrocarbon groups as described above (for example, alkylcycloalkyl groups or cycloalkylalkyl groups such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having alkyl groups (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), aromatic hydrocarbon groups having alicyclic hydrocarbon groups (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), and aryl-cycloalkyl groups such as phenylcyclohexyl group. R a2’ and R a3’ When they bond to each other and form a heterocyclic group with the carbon atoms to which they are bonded and X, -C(R a1’ )(R a2’ )-XR a3’ The following groups are examples. * indicates a binding site. TIFF2023156258000083.tif19124R a1’ and R a2’ Preferably, at least one of them is a hydrogen atom. na' is preferably 0.

[0107] The following are examples of base (1): In equation (1), R a1 , R a2 and R a3 A group in which the parentheses is an alkyl group, ma=0, and na=1. A tert-butoxycarbonyl group is preferred as the group. In equation (1), R a1 , R a2 However, these combine with the carbon atoms to which they bond to form an adamantyl group, R a3 A group that is an alkyl group, with ma=0 and na=1. In equation (1), R a1 and R a2Each of them is an alkyl group independently, and R a3 This is an adamantyl group with ma=0 and na=1. The following are specific examples of group (1). * indicates a bonding site. TIFF2023156258000084.tif130166

[0108] The following are specific examples of group (2). * indicates a bonding site. TIFF2023156258000085.tif55153

[0109] The monomer (a1) is preferably a monomer having an acid-unstable group and an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer having an acid-unstable group.

[0110] Among (meth)acrylic monomers having acid-unstable groups, those having alicyclic hydrocarbon groups with 5 to 20 carbon atoms are preferred. If a resin (A) having structural units derived from a monomer (a1) having a bulky structure such as an alicyclic hydrocarbon group is used in the resist composition, the resolution of the resist pattern can be improved.

[0111] Structural units derived from (meth)acrylic monomers having group (1) include structural units represented by formula (a1-0) (hereinafter sometimes referred to as structural unit (a1-0)), structural units represented by formula (a1-1) (hereinafter sometimes referred to as structural unit (a1-1)), or structural units represented by formula (a1-2) (hereinafter sometimes referred to as structural unit (a1-2)). Preferably, it is at least one structural unit selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2), and more preferably, it is at least one or two structural units selected from the group consisting of structural unit (a1-1) and structural unit (a1-2). These may be used individually or in combination of two or more. TIFF2023156258000086.tif44143[In formulas (a1-0), (a1-1), and (a1-2), L a01 , L a1 and L a2 These are, independently, -O- or *-O-(CH2) k1 -CO-O- represents a bond, where k1 is an integer from 1 to 7, and * represents the bond site with -CO-. R a01 , R a4 and R a5 Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. R a02 , R a03 and R a04 Each of these independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. R a6 and R a7 Each of these independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by a combination of these. m1' represents an integer between 0 and 14. n1 represents an integer between 0 and 10. n1' represents an integer between 0 and 3.

[0112] R a01 , R a4 and R a5 This is preferably a hydrogen atom or a methyl group, and more preferably a methyl group. L a01 , L a1 and L a2 Preferably, an oxygen atom or *-O-(CH2) k01 It is -CO-O- (where k01 is preferably an integer from 1 to 4, more preferably 1), and more preferably an oxygen atom. R a02 , R a03 , R a04 , R a6 and R a7The alkyl groups, alkenyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof in formula (1) are R a1 , R a2 and R a3 Similar groups to those listed above can be cited. R a02 , R a03 , and R a04 The alkyl group in is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a6 and R a7 The alkyl group in is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and even more preferably an ethyl group, an isopropyl group, or a t-butyl group. R a6 and R a7 The alkenyl group in is preferably an alkenyl group having 2 to 6 carbon atoms, and more preferably an ethenyl group, a propenyl group, an isopropenyl group, or a butenyl group. R a02 , R a03 , R a04 , R a6 and R a7 The number of carbon atoms in the alicyclic hydrocarbon group is preferably 5 to 12, and more preferably 5 to 10. R a02 , R a03 , R a04 , R a6 and R a7 The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 12, and more preferably 6 to 10. In groups formed by combining an alkyl group and an alicyclic hydrocarbon group, it is preferable that the total number of carbon atoms in the combined alkyl group and alicyclic hydrocarbon group is 18 or less. In groups formed by combining an alkyl group and an aromatic hydrocarbon group, it is preferable that the total number of carbon atoms in the combined alkyl group and aromatic hydrocarbon group is 18 or less. R a02 and R a03The group is preferably an alkyl group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, and more preferably a methyl group, an ethyl group, a phenyl group, or a naphthyl group. R a04 The group is preferably an alkyl group having 1 to 6 carbon atoms or an alicyclic hydrocarbon group having 5 to 12 carbon atoms, and more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. R a6 and R a7 The group is preferably an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, a phenyl group, or a naphthyl group, and even more preferably an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, or a phenyl group. m1' is preferably an integer between 0 and 3, and more preferably 0 or 1. n1 is preferably an integer between 0 and 3, and more preferably 0 or 1. n1' is preferably 0 or 1.

[0113] Examples of structural units (a1-0) include structural units represented by any of the formulas (a1-0-1) to (a1-0-18) and R in structural unit (a1-0). a01 Examples of structural units in which the corresponding methyl group is replaced by a hydrogen atom, a halogen atom, a haloalkyl group (an alkyl group having a halogen atom), or another alkyl group are given, with structural units represented by any of the formulas (a1-0-1) to (a1-0-10), (a1-0-13), or (a1-0-14) being preferred. JPEG2023156258000087.jpg95163

[0114] Examples of structural units (a1-1) include structural units derived from monomers described in Japanese Patent Publication No. 2010-204646. In particular, structural units represented by any of formulas (a1-1-1) to (a1-1-7) and R in structural unit (a1-1) a4A structural unit in which the corresponding methyl group is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group is preferred, and a structural unit represented by any of formulas (a1-1-1) to (a1-1-4) is more preferred. JPEG2023156258000088.jpg39170

[0115] The structural unit (a1-2) is a structural unit represented by any of the formulas (a1-2-1) to (a1-2-14) and R in the structural unit (a1-2). a5 Examples of structural units in which the corresponding methyl group is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group include structural units represented by any of the formulas (a1-2-2), (a1-2-5), (a1-2-6), and (a1-2-10) to (a1-2-14). TIFF2023156258000089.tif62163

[0116] When resin (A) contains structural units (a1-0) and / or structural units (a1-1) and / or structural units (a1-2), the total content of these is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, and even more preferably 30 mol% or more, relative to the total structural units of resin (A). Alternatively, it may be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, and even more preferably 70 mol% or less. Specifically, it can be 10 to 95 mol%, preferably 15 to 90 mol%, more preferably 20 to 85 mol%, even more preferably 25 to 70 mol%, and even more preferably 30 to 70 mol%. When resin (A) contains structural units (a1-0), the content is 5 mol% or more, preferably 10 mol% or more, relative to the total structural units of resin (A). Alternatively, it can be 80 mol% or less, preferably 75 mol% or less, and more preferably 70 mol% or less. Specifically, it can be 5 to 80 mol%, preferably 5 to 75 mol%, and more preferably 10 to 70 mol%. When resin (A) contains structural unit (a1-1) and / or structural unit (a1-2), the total content of these is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, and even more preferably 30 mol% or more, relative to the total structural units of resin (A). Alternatively, it may be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, and even more preferably 70 mol% or less. Specifically, it may be 10 to 90 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, even more preferably 20 to 80 mol%, and even more preferably 20 to 75 mol%.

[0117] Examples of structural units having a base (2) in structural unit (a1) include the structural unit represented by formula (a1-4) (hereinafter sometimes referred to as "structural unit (a1-4)"). TIFF2023156258000090.tif4563[In formula (a1-4), R a32 This represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group which may have a halogen atom. R a33 This represents a halogen atom, a hydroxyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C2-C12 alkoxyalkyl group, a C2-C12 alkoxyalkoxy group, a C2-C4 alkylcarbonyl group, a C2-C4 alkylcarbonyloxy group, an acryloyloxy group, or a methacryloyloxy group. A a30 This is a single bond or *-X a31 -( A a32 -X a32 ) nc - represents -R a32 This represents the bonding site with the carbon atom to which it is bonded. A a32 This represents an alkanediyl group with 1 to 8 carbon atoms. X a31 and Xa32 These represent -O-, -CO-O-, or -O-CO- independently. nc represents 0 or 1. la represents an integer between 0 and 4. If la is an integer greater than or equal to 2, multiple R a33 They may be the same or different from one another. R a34 and R a35 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R a36 R represents a hydrocarbon group with 1 to 20 carbon atoms. a35 and R a36 These atoms bond with each other to form a divalent hydrocarbon group having 2 to 20 carbon atoms, and the -CH2- contained in this hydrocarbon group and the divalent hydrocarbon group may be replaced with -O- or -S-.

[0118] R a32 and R a33 Examples of halogen atoms in this context include fluorine atoms, chlorine atoms, and bromine atoms. R a32 Examples of C1-C6 alkyl groups that may have halogen atoms include trifluoromethyl, difluoromethyl, methyl, perfluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, ethyl, perfluoropropyl, 2,2,3,3,3-pentafluoropropyl, propyl, perfluorobutyl, 1,1,2,2,3,3,4,4-octafluorobutyl, butyl, perfluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, pentyl, hexyl, and perfluorohexyl groups. R a32 The hydrogen atom or an alkyl group having 1 to 4 carbon atoms is preferred, a hydrogen atom, a methyl group, or an ethyl group is more preferred, and a hydrogen atom or a methyl group is even more preferred. R a33Examples of alkyl groups in this context include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. The alkyl group is preferably a C1-C4 alkyl group, more preferably a methyl or ethyl group, and even more preferably a methyl group. R a33 Examples of alkoxy groups in this compound include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, pentyloxy, and hexyloxy groups. The alkoxy group is preferably a carbon-1 to carbon-4 alkoxy group, more preferably a methoxy or ethoxy group, and even more preferably a methoxy group. R a33 Examples of alkoxyalkyl groups in this context include methoxymethyl, ethoxyethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, sec-butoxymethyl, and tert-butoxymethyl groups. The alkoxyalkyl group is preferably a carbon-2 to carbon-8 alkoxyalkyl group, more preferably a methoxymethyl or ethoxyethyl group, and even more preferably a methoxymethyl group. R a33 Examples of alkoxyalkoxy groups in this context include methoxymethoxy, methoxyethoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy, isopropoxymethoxy, butoxymethoxy, sec-butoxymethoxy, and tert-butoxymethoxy. The alkoxyalkoxy group is preferably one having 2 to 8 carbon atoms, with methoxyethoxy or ethoxyethoxy being more preferred. R a33 Examples of alkylcarbonyl groups in this compound include acetyl, propionyl, and butyryl groups. The alkylcarbonyl group is preferably one having 2 to 3 carbon atoms, with acetyl being more preferred. R a33Examples of alkylcarbonyloxy groups in this context include acetyloxy groups, propionyloxy groups, and butyryloxy groups. The alkylcarbonyloxy group is preferably one having 2 to 3 carbon atoms, and more preferably an acetyloxy group. R a33 The group is preferably a halogen atom, a hydroxyl group, a C1-C4 alkyl group, a C1-C4 alkoxy group, or a C2-C8 alkoxyalkoxy group; more preferably a fluorine atom, an iodine atom, a hydroxyl group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group; and even more preferably a fluorine atom, an iodine atom, a hydroxyl group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0119] *-X a31 -( A a32 -X a32 ) nc - for example, *-O-, *-CO-O-, *-O-CO-, *-CO-OA a32 -CO-O-, *-O-CO-A a32 -O-, *-OA a32 -CO-O-, *-CO-OA a32 -O-CO-, *-O-CO-A a32 -O-CO- is one example. In particular, *-CO-O- and *-CO-OA a32 -CO-O- or *-OA a32 -CO-O- is preferred. A a32 Examples of alkanediyl groups in this compound include methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. A a32 It is preferable that this is a methylene group or an ethylene group. A a30 These are single bonds, *-CO-O- or *-CO-OA a32It is preferably -CO-O-, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-.

[0120] la is preferably 0, 1, or 2, more preferably 0 or 1, and even more preferably 0. R a34 , R a35 and R a36 Examples of hydrocarbon groups in this context include alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups that combine these. Examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl groups. Alicyclic hydrocarbon groups may be monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, norbornyl, and the following groups (* indicates a bonding site). Examples of aromatic hydrocarbon groups include phenyl groups, naphthyl groups, anthryl groups, biphenyl groups, phenanthryl groups, and other aryl groups. Examples of combined groups include groups that combine alkyl groups and alicyclic hydrocarbon groups as described above (for example, alkylcycloalkyl groups or cycloalkylalkyl groups such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having alkyl groups (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), aromatic hydrocarbon groups having alicyclic hydrocarbon groups (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), and aryl-cycloalkyl groups such as phenylcyclohexyl group. In particular, R a36 Examples include alkyl groups having 1 to 18 carbon atoms, alicyclic hydrocarbon groups having 3 to 18 carbon atoms, aromatic hydrocarbon groups having 6 to 18 carbon atoms, or groups formed by combining these.

[0121] R a34 Preferably, it is a hydrogen atom. R a35 Preferably, this is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a methyl group or an ethyl group. R a36 The hydrocarbon group is preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by a combination thereof, and more preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms. a36 The alkyl group and alicyclic hydrocarbon group in R are preferably unsubstituted. a36 In this context, the aromatic hydrocarbon group is preferably an aromatic ring having an aryloxy group with 6 to 10 carbon atoms.

[0122] -OC(R) in structural units (a1-4) a34 )(R a35 )-ORa36 It is eliminated upon contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxyl group. -OC(R a34 )(R a35 )-OR a36 It is preferable that the atom is bonded to the ortho- or para-position of the benzene ring, and more preferably to the para-position.

[0123] Examples of structural units (a1-4) include monomer-derived structural units described in Japanese Patent Publication No. 2010-204646. Preferably, structural units represented by formulas (a1-4-1) to (a1-4-24) and R in structural unit (a1-4). a32 Examples of structural units in which the hydrogen atom corresponding to is replaced by a halogen atom, a haloalkyl group, or an alkyl group are given, and more preferably, structural units represented by formulas (a1-4-1) to (a1-4-5), (a1-4-10), (a1-4-13), (a1-4-14), (a1-4-19), and (a1-4-20), respectively. TIFF2023156258000092.tif127160

[0124] If resin (A) contains structural units (a1-4), the content of these units is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, even more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and even more preferably 20 to 60 mol% relative to the total amount of all structural units of resin (A).

[0125] Structural units derived from (meth)acrylic monomers having group (2) include the structural unit represented by formula (a1-5) (hereinafter sometimes referred to as "structural unit (a1-5)"). TIFF2023156258000093.tif4253[In formula (a1-5), R a8 This represents an alkyl group having 1 to 6 carbon atoms, which may contain a halogen atom, a hydrogen atom, or a halogen atom. Z a1This is a single bond or *-(CH2) h3 -CO-L 54 - represents, h3 represents an integer from 1 to 4, and * represents L 51 This represents the connection point. L 51 , L 52 , L 53 and L 54 These represent either -O- or -S- independently. s1 represents an integer between 1 and 3. s1' represents an integer between 0 and 3.

[0126] Examples of halogen atoms include fluorine atoms and chlorine atoms, with fluorine atoms being preferred. C1-C6 alkyl groups that may have halogen atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, fluoromethyl, and trifluoromethyl groups. In equation (a1-5), R a8 The preferred element is a hydrogen atom, a methyl group, or a trifluoromethyl group. L 51 An oxygen atom is preferred. L 52 and L 53 Preferably, one of them is -O- and the other is -S-. s1 is preferably 1. s1' is preferably an integer between 0 and 2. Z a1 A single bond or *-CH2-CO-O- is preferred.

[0127] Examples of structural units (a1-5) include monomer-derived structural units described in Japanese Patent Publication No. 2010-61117. Among these, structural units represented by formulas (a1-5-1) to (a1-5-4) are preferred, and structural units represented by formula (a1-5-1) or (a1-5-2) are more preferred. TIFF2023156258000094.tif31130

[0128] If resin (A) contains structural units (a1-5), the content of these units is preferably 1 to 50 mol%, more preferably 3 to 45 mol%, even more preferably 5 to 40 mol%, and even more preferably 5 to 30 mol%, relative to the total structural units of resin (A).

[0129] In addition, the following structural units (a1) can also be listed. TIFF2023156258000095.tif27161

[0130] If resin (A) contains structural units such as (a1-3-1) to (a1-3-7), the content of these structural units is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, even more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol% relative to the total structural units of resin (A).

[0131] <Structural unit (s)> Structural units (s) are derived from monomers that do not have acid-unstable groups (hereinafter sometimes referred to as "monomers (s)"). Monomers that do not have acid-unstable groups and are known in the field of photoresists can be used to derive structural units (s). The structural unit (s) preferably has a hydroxyl group or a lactone ring. If a resin containing a structural unit having a hydroxyl group and not having an acid-unstable group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and not having an acid-unstable group (hereinafter sometimes referred to as "structural unit (a3)") is used in the resist composition of the present invention, the resolution of the resist pattern and the adhesion to the substrate can be improved.

[0132] <Structural Unit (a2)> Structural unit (a2) is a structural unit represented by formula (a2) and has an alcoholic hydroxyl group or a phenolic hydroxyl group. TIFF2023156258000096.tif3194[In formula (a2), R a50This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. A a50 This is a single bond or *-X a51 -( A a52 -X a52 ) nb - represents -R a50 This represents the bonding site with the carbon atom to which it is bonded. A a52 This represents an alkanediyl group with 1 to 8 carbon atoms. X a51 and X a52 These represent -O-, -CO-O-, or -O-CO- independently. nb represents either 0 or 1. W a50 This represents a cyclic hydrocarbon group having 5 to 12 carbon atoms, which may have substituents. L a50 This represents a chain-like hydrocarbon group having 1 to 12 carbon atoms, which may have single bonds or fluorine atoms. ma50 represents an integer between 1 and 5. R a50 Examples of halogen atoms in this context include fluorine atoms, chlorine atoms, and bromine atoms. R a50 Examples of C1-C6 alkyl groups that may have halogen atoms include trifluoromethyl, difluoromethyl, methyl, perfluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, ethyl, perfluoropropyl, 2,2,3,3,3-pentafluoropropyl, propyl, perfluorobutyl, 1,1,2,2,3,3,4,4-octafluorobutyl, butyl, perfluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, pentyl, hexyl, and perfluorohexyl groups. The number of carbon atoms in the alkyl group is preferably 1-4, more preferably 1-3, and even more preferably 1 or 2. R a50The hydrogen atom or an alkyl group having 1 to 4 carbon atoms is preferred, a hydrogen atom, a methyl group, or an ethyl group is more preferred, and a hydrogen atom or a methyl group is even more preferred.

[0133] A a50 A in a52 Examples of alkanediyl groups include methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. The number of carbon atoms in the alkanediyl group is preferably 1 to 6, more preferably 1 to 4, even more preferably 1 to 3, and even more preferably 1 or 2. A a52 It is preferable that this is a methylene group or an ethylene group. *-X a51 -( A a52 -X a52 ) nb - for example, *-O-, *-CO-O-, *-O-CO-, *-CO-OA a52 -CO-O-, *-O-CO-A a52 -O-, *-OA a52 -CO-O-, *-CO-OA a52 -O-CO-, *-O-CO-A a52 -O-CO- is one example. In particular, *-CO-O- and *-CO-OA a52 -CO-O- or *-OA a52 -CO-O- is preferred. A a50 These are single bonds, *-CO-O- or *-CO-OA a52 It is preferably -CO-O-, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-.

[0134] W a50Examples of cyclic hydrocarbon groups include divalent alicyclic hydrocarbon groups and divalent aromatic hydrocarbon groups. W a50 Examples of monocyclic divalent alicyclic hydrocarbon groups include monocyclic cycloalkanediyl groups such as cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl. Examples of polycyclic divalent alicyclic hydrocarbon groups include polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, and adamantane-2,6-diyl. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 6 to 12, and more preferably 6 to 10. W a50 Examples of divalent aromatic hydrocarbon groups in this compound include phenylene groups and naphthyl groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 12, and more preferably 6 to 10. W a50 The substituents that the cyclic hydrocarbon group having 5 to 12 carbon atoms may have include halogen atoms, hydroxyl groups, alkyl groups having 1 to 12 carbon atoms, haloalkyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 12 carbon atoms, alkoxyalkyl groups having 2 to 12 carbon atoms, alkoxyalkoxy groups having 2 to 12 carbon atoms, alkylcarbonyl groups having 2 to 4 carbon atoms, alkylcarbonyloxy groups having 2 to 4 carbon atoms, acryloyloxy groups, or methacryloyloxy groups. a50 The number of substituents it may have may be one or two or more. Examples of halogen atoms include fluorine atoms, chlorine atoms, and bromine atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl or ethyl group, and even more preferably a methyl group. Examples of haloalkyl groups include trifluoromethyl, difluoromethyl, perfluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, perfluoropropyl, 2,2,3,3,3-pentafluoropropyl, perfluorobutyl, 1,1,2,2,3,3,4,4-octafluorobutyl, perfluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, perfluorohexyl, chloromethyl, bromomethyl, and iodomethyl groups. The number of carbon atoms in the haloalkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, and tert-butoxy groups. The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy or ethoxy group, and even more preferably a methoxy group. Examples of alkoxyalkyl groups include methoxymethyl group, ethoxyethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxymethyl group, and tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group. Examples of alkoxyalkoxy groups include methoxymethoxy, methoxyethoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy, isopropoxymethoxy, butoxymethoxy, sec-butoxymethoxy, and tert-butoxymethoxy. The alkoxyalkoxy group is preferably one having 2 to 8 carbon atoms, with methoxyethoxy or ethoxyethoxy being more preferred. Examples of alkylcarbonyl groups include acetyl, propionyl, and butyryl groups. A alkylcarbonyl group having 2 to 3 carbon atoms is preferred, with the acetyl group being more preferred. Examples of alkylcarbonyloxy groups include acetyloxy groups, propionyloxy groups, and butyryloxy groups. The alkylcarbonyloxy group is preferably one having 2 to 3 carbon atoms, and more preferably an acetyloxy group. W a50 The substituents on the cyclic hydrocarbon group are preferably halogen atoms, hydroxyl groups, C1-C4 alkyl groups, C1-C4 alkoxy groups, or C2-C8 alkoxyalkoxy groups; more preferably fluorine atoms, iodine atoms, hydroxyl groups, methyl groups, methoxy groups, ethoxy groups, ethoxyethoxy groups, or ethoxymethoxy groups; and even more preferably fluorine atoms, iodine atoms, hydroxyl groups, methyl groups, methoxy groups, or ethoxyethoxy groups.

[0135] L a50 Examples of linear alkanediyl groups with 1 to 12 carbon atoms include methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, etc., as well as ethane-1,1-diyl group, propane-1,1 Examples of branched alkanediyl groups include -diyl group, propane-1,2-diyl group, propane-2,2-diyl group, 1-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-dimethylpropane-1,3-diyl group, pentane-2,4-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, pentane-2,4-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, even more preferably 1 to 6, and even more preferably 1 to 4. L a50 The fluorine atoms present may be one or two or more. ma50 is preferably an integer between 1 and 4, and more preferably an integer between 1 and 3.

[0136] When manufacturing a resist pattern from the resist composition of the present invention, if a high-energy beam such as a KrF excimer laser (248 nm), electron beam, or EUV (ultra-ultraviolet light) is used as the exposure light source, a structural unit (a2) having a phenolic hydroxyl group is preferred, and it is more preferable to use the structural unit (a2-A) described later. Furthermore, if an ArF excimer laser (193 nm) or the like is used, a structural unit (a2) having an alcoholic hydroxyl group is preferred, and it is more preferable to use the structural unit (a2-1) described later. The structural unit (a2) may consist of one type alone, or it may consist of two or more types.

[0137] A structural unit having a phenolic hydroxyl group in structural unit (a2) is the structural unit represented by formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A)"). TIFF2023156258000097.tif4753[In formula (a2-A), R a50 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. R a51 This represents a halogen atom, a hydroxyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C2-C12 alkoxyalkyl group, a C2-C12 alkoxyalkoxy group, a C2-C4 alkylcarbonyl group, a C2-C4 alkylcarbonyloxy group, an acryloyloxy group, or a methacryloyloxy group. A a50 This is a single bond or *-X a51 -( A a52 -X a52 ) nb - represents -R a50 This represents the bonding site with the carbon atom to which it is bonded. A a52 This represents an alkanediyl group with 1 to 8 carbon atoms. X a51 and X a52 These represent -O-, -CO-O-, or -O-CO- independently. nb represents either 0 or 1. mb represents an integer between 0 and 4. If mb is an integer greater than or equal to 2, multiple R a51 They may be the same or different from each other.

[0138] R a50 and A a50 These are the same types of bases as those exemplified in equation (a2). R a51 Examples of halogen atoms in this context include fluorine atoms, chlorine atoms, and bromine atoms. R a51 Examples of alkyl groups in this context include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. The alkyl group is preferably a C1-C4 alkyl group, more preferably a methyl or ethyl group, and even more preferably a methyl group. R a51 Examples of alkoxy groups in this compound include methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, and tert-butoxy groups. The alkoxy group is preferably a carbon-1 to carbon-4 alkoxy group, more preferably a methoxy or ethoxy group, and even more preferably a methoxy group. R a51 Examples of alkoxyalkyl groups in this context include methoxymethyl, ethoxyethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, sec-butoxymethyl, and tert-butoxymethyl groups. The alkoxyalkyl group is preferably a carbon-2 to carbon-8 alkoxyalkyl group, more preferably a methoxymethyl or ethoxyethyl group, and even more preferably a methoxymethyl group. R a51Examples of alkoxyalkoxy groups in this context include methoxymethoxy, methoxyethoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy, isopropoxymethoxy, butoxymethoxy, sec-butoxymethoxy, and tert-butoxymethoxy. The alkoxyalkoxy group is preferably one having 2 to 8 carbon atoms, with methoxyethoxy or ethoxyethoxy being more preferred. R a51 Examples of alkylcarbonyl groups in this compound include acetyl, propionyl, and butyryl groups. The alkylcarbonyl group is preferably one having 2 to 3 carbon atoms, with acetyl being more preferred. R a51 Examples of alkylcarbonyloxy groups in this context include acetyloxy groups, propionyloxy groups, and butyryloxy groups. The alkylcarbonyloxy group is preferably one having 2 to 3 carbon atoms, and more preferably an acetyloxy group. R a51 The group is preferably a halogen atom, a hydroxyl group, a C1-C4 alkyl group, a C1-C4 alkoxy group, or a C2-C8 alkoxyalkoxy group; more preferably a fluorine atom, an iodine atom, a hydroxyl group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group; and even more preferably a fluorine atom, an iodine atom, a hydroxyl group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0139] mb is preferably 0, 1, or 2, and more preferably 0 or 1. Preferably, at least one hydroxyl group is bonded to the m- or p-position of the benzene ring. If two or more hydroxyl groups are present, it is preferable that the two hydroxyl groups are bonded to the m- and p-positions, respectively.

[0140] Examples of structural units (a2-A) include monomer-derived structural units described in Japanese Patent Publication No. 2010-204634 and Japanese Patent Publication No. 2012-12577. As for the structural unit (a2-A), the structural unit is represented by formulas (a2-2-1) to (a2-2-24), and in the structural unit represented by formulas (a2-2-1) to (a2-2-24), R in the structural unit (a2-A) a50 Examples of structural units in which the methyl group corresponding to is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. Structural unit (a2-A) is a structural unit represented by formulas (a2-2-1) to (a2-2-4), a structural unit represented by formula (a2-2-6), a structural unit represented by formula (a2-2-8), a structural unit represented by formulas (a2-2-12) to (a2-2-18), and a structural unit represented by formulas (a2-2-1) to (a2-2-4), a structural unit represented by formula (a2-2-6), a structural unit represented by formula (a2-2-8), and a structural unit represented by formulas (a2-2-12) to (a2-2-18), in which R a50 Preferably, the structural unit is one in which the corresponding methyl group is replaced by a hydrogen atom, and in the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-4), the structural unit represented by formula (a2-2-8), the structural unit represented by formulas (a2-2-12) to (a2-2-14), the structural unit represented by formula (a2-2-18), and the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-4), the structural unit represented by formula (a2-2-8), the structural unit represented by formulas (a2-2-12) to (a2-2-14), and the structural unit represented by formula (a2-2-18), the R in structural unit (a2-A) a50 It is more preferable that the corresponding methyl group is replaced by a hydrogen atom in the structural unit represented by formula (a2-2-3), formula (a2-2-4), formula (a2-2-8), and in the structural unit represented by formula (a2-2-3), formula (a2-2-4), and formula (a2-2-8), the R in structural unit (a2-A) a50 It is even more preferable that the corresponding methyl group is replaced by a hydrogen atom in the structural unit. TIFF2023156258000098.tif79169

[0141] When the resin (A) contains structural units (a2-A), the content of structural units (a2-A) is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 15 mol% or more, and even more preferably 20 mol% or more, relative to the total structural units. Furthermore, it is preferably 80 mol% or less, more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, even more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%. The structural unit (a2-A) can be incorporated into resin (A) by polymerizing using structural unit (a1-4), for example, and then treating with an acid such as p-toluenesulfonic acid. Alternatively, the structural unit (a2-A) can be incorporated into resin (A) by polymerizing using acetoxystyrene, for example, and then treating with an alkali such as tetramethylammonium hydroxide.

[0142] Examples of structural units (a2-A) include the structural unit represented by the following formula (a2-A1) (hereinafter sometimes referred to as "structural unit (a2-A1)") and the structural unit represented by the formula (a2-A2) (hereinafter sometimes referred to as "structural unit (a2-A2)"). TIFF2023156258000099.tif52136 [In formula (a2-A1) and formula (a2-A2), R a50 and A a50 These expressions have the same meaning as equation (a2). mb1 represents an integer between 0 and 4. R a52 This represents a halogen atom. R a53 This represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. mb2 and mb3 each independently represent an integer from 0 to 4, and if mb2 is 2 or greater, multiple R a52 They may be the same or different from each other, and if mb3 is 2 or more, multiple R a53 The terms may be identical or different, satisfying the condition 1 ≤ mb2 + mb3 ≤ 4. R a52 The halogen atom is W a50 substituents of the cyclic hydrocarbon group and R a51 Examples include the same halogen atoms as in R. a52 The halogen atom is preferably a fluorine atom or an iodine atom. R a53 The C1-C6 alkyl group, C1-C6 alkoxy group, C2-C12 alkoxyalkyl group, C2-C12 alkoxyalkoxy group, C2-C4 alkylcarbonyl group, C2-C4 alkylcarbonyloxy group, acryloyloxy group, or methacryloyloxy group are, respectively, W a50 substituents of the cyclic hydrocarbon group and R a51 Examples of alkyl groups, alkoxy groups, alkoxyalkyl groups, alkoxyalkoxy groups, alkylcarbonyl groups, alkylcarbonyloxy groups, acroyloxy groups, and methacryloyloxy groups are the same as those mentioned above, with methyl groups, methoxy groups, ethoxy groups, ethoxyethoxy groups, or ethoxymethoxy groups being more preferred, and methoxy groups or ethoxyethoxy groups being even more preferred. mb1 is preferably an integer from 0 to 3, more preferably an integer from 0 to 2, and even more preferably 0 or 1. mb2 is preferably an integer from 0 to 3, more preferably an integer from 1 to 3, and even more preferably 1 or 2. mb3 is preferably an integer from 0 to 3, more preferably an integer from 0 to 2, and even more preferably 0 or 1.

[0143] A structural unit having an alcoholic hydroxyl group in structural unit (a2) is the structural unit represented by formula (a2-1) (hereinafter sometimes referred to as "structural unit (a2-1)"). TIFF2023156258000100.tif4258[In formula (a2-1), L a3 is -O- or *-O-(CH2) k2 -CO-O- represents, k2 represents an integer between 1 and 7. * represents a connection site with -CO-. R a14 represents a hydrogen atom or a methyl group. R a15 and R a16 Each of these independently represents a hydrogen atom, a methyl group, or a hydroxyl group. o1 represents an integer between 0 and 10.

[0144] In equation (a2-1), L a3 Preferably, -O-, -O-(CH2) f1 The result is -CO-O- (where f1 represents any integer from 1 to 4), and more preferably -O-. R a14 The group is preferably a methyl group. R a15 Preferably, it is a hydrogen atom. R a16 This is preferably a hydrogen atom or a hydroxyl group. o1 is preferably an integer between 0 and 3, more preferably 0 or 1.

[0145] Examples of structural units (a2-1) include structural units derived from monomers described in Japanese Patent Publication No. 2010-204646. Structural units represented by any of formulas (a2-1-1) to (a2-1-6) are preferred, structural units represented by any of formulas (a2-1-1) to (a2-1-4) are more preferred, and structural units represented by formula (a2-1-1) or (a2-1-3) are even more preferred. TIFF2023156258000101.tif54148 When resin (A) contains structural units (a2-1), the content is preferably 1 mol% or more, and more preferably 2 mol% or more, relative to the total structural units of resin (A). Also, it is preferably 45 mol% or less, more preferably 40 mol% or less, more preferably 35 mol% or less, even more preferably 20 mol% or less, and even more preferably 10 mol% or less. Specifically, it is preferably 1 to 45 mol%, more preferably 1 to 40 mol%, more preferably 1 to 35 mol%, even more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol%.

[0146] A structural unit having an alcoholic hydroxyl group in structural unit (a2) is the structural unit represented by formula (a2-B) (hereinafter sometimes referred to as "structural unit (a2-B)"). TIFF2023156258000102.tif51104[In formula (a2-B), R a50 and A a50 These expressions have the same meaning as equation (a2). R a54 and R a55 Each of these independently represents a fluorinated alkyl group having 1 to 4 carbon atoms. L a51 This represents a single bond or an alkanediyl group having 1 to 3 carbon atoms, and the alkanediyl group may be substituted with a fluorine atom. R a56 represents a halogen atom, a hydroxyl group, a C1-C4 haloalkyl group, or a C1-C12 alkyl group, and the -CH2- contained in the alkyl group may be replaced with -O- or -CO-. mb4 represents an integer between 1 and 3, and when mb4 is 2 or greater, multiple R a54 , R a55 and L a51 These may be identical or different from one another. mb5 represents an integer between 0 and 4, and when mb5 is 2 or greater, multiple R a56They may be identical or different from each other, provided that 1 ≤ mb4 + mb5 ≤ 5.

[0147] R a54 and R a55 Examples of C1-C4 fluorinated alkyl groups include, independently, trifluoromethyl group, 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, and 4,4,4-trifluorobutyl group. a54 and R a55 A trifluoromethyl group is preferred as the component. L a51 Examples of alkanediyl groups having 1 to 3 carbon atoms include methylene group, ethane-1,1-diyl group, propane-1,1-diyl group, and propane-2,2-diyl group. a51 A single bond or a methylene group is preferred. R a56 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. R a56 In this context, a C1-C4 haloalkyl group refers to an alkyl group having a halogen atom and containing C1-C4 atoms, such as chloromethyl, bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, and perfluorobutyl groups. R a56 Examples of C1-C12 alkyl groups in this context include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, and nonyl groups. The number of carbon atoms in the alkyl group is preferably 1-9, more preferably 1-6, and even more preferably 1-4. R a56 If the -CH2- contained in the alkyl group represented by is replaced with -O- or -CO-, the number of carbon atoms before the replacement shall be the total number of carbon atoms of the alkyl group. Also, R a56It may have a hydroxyl group (a group in which -CH2- contained in a methyl group is replaced with -O-), a carboxyl group (a group in which -CH2-CH2- contained in an ethyl group is replaced with -O-CO-), an alkoxy group having 1 to 11 carbon atoms (a group in which -CH2- contained in an alkyl group having 2 to 12 carbon atoms is replaced with -O-), an alkoxycarbonyl group having 2 to 11 carbon atoms (a group in which -CH2-CH2- contained in an alkyl group having 3 to 12 carbon atoms is replaced with -O-CO-), an alkylcarbonyl group having 2 to 12 carbon atoms (a group in which -CH2- contained in an alkyl group having 2 to 12 carbon atoms is replaced with -CO-), or an alkylcarbonyloxy group having 2 to 11 carbon atoms (a group in which -CH2-CH2- contained in an alkyl group having 3 to 12 carbon atoms is replaced with -CO-O-). R a56 Among these, halogen atoms, C1-C4 haloalkyl groups, or C1-C12 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-) are preferred. mb4 is preferably 1 or 2, more preferably 1. Even more preferably, mb4 is 1 and the base in parentheses is bonded in the para position. mb5 is preferably an integer between 0 and 2, more preferably 0 or 1, and even more preferably 0.

[0148] It is more preferable that the structural unit (a2-B) is a structural unit represented by the following formula (a2-B1) (hereinafter sometimes referred to as "structural unit (a2-B1)"). TIFF2023156258000103.tif4787[In formula (a2-B1), R a57 represents a hydrogen atom or a methyl group. A a53 represents a single bond or *-CO-O-, where * is -R a57 This represents the bonding site with the carbon atom to which it is bonded. R a56 mb4 and mb5 represent the same meaning as in equation (a2-B), respectively.

[0149] In equation (a2-B1), R a57 Preferably, it is a hydrogen atom. A a53 The bond is preferably a single bond.

[0150] Examples of structural units (a2-B) are listed below. TIFF2023156258000104.tif62168

[0151] In the structural units represented by equations (a2-B-1) to (a2-B-8), R a57 In the structural units in which the hydrogen atom corresponding to is replaced by a methyl group, R is also represented in the structural units shown in formulas (a2-B-9) to (a2-B-16). a57 Structural units in which the corresponding methyl group is replaced by a hydrogen atom can also be given as specific examples of structural unit (a2-B). Among these, structural units represented by formulas (a2-B-1) to (a2-B-8) are preferred, structural units represented by formulas (a2-B-1) to (a2-B-4) are more preferred, and structural unit represented by formula (a2-B-1) is even more preferred.

[0152] When resin (A) contains structural units (a2-B), the content is preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, relative to the total structural units of resin (A). Furthermore, it is preferably 80 mol% or less, more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, even more preferably 10 to 70 mol%, and even more preferably 10 to 65 mol%.

[0153] <Structural unit (a3)> The lactone ring of the structural unit (a3) ​​may be a monocyclic ring such as a β-propiolactone ring, a γ-butyrolactone ring, or a δ-valerolactone ring, or it may be a fused ring of a monocyclic lactone ring and another ring. Preferably, it may be a γ-butyrolactone ring, an adamantane lactone ring, or a bridging ring containing a γ-butyrolactone ring structure (for example, a structural unit represented by the following formula (a3-2)).

[0154] The structural unit (a3) ​​is preferably a structural unit represented by formula (a3-1), formula (a3-2), formula (a3-3), or formula (a3-4). One of these may be included alone, or two or more may be included. TIFF2023156258000105.tif51161[In formulas (a3-1), (a3-2), (a3-3), and (a3-4), L a4 , L a5 and L a6 These are, independently, -O- or *-O-(CH2) k3 This represents a base represented by -CO-O-(where k3 is an integer from 1 to 7). L a7 is -O-, *-OL a8 -O-, *-OL a8 -CO-O-, *-OL a8 -CO-OL a9 -CO-O- or *-OL a8 -O-CO-L a9 Represents -O- L a8 and L a9 Each of these independently represents an alkanediyl group with 1 to 6 carbon atoms. * indicates a bonding site with a carbonyl group. R a18 , R a19 , R a20 and R a24 Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. X a3 represents -CH2- or an oxygen atom. R a21 This represents an aliphatic hydrocarbon group with 1 to 4 carbon atoms. R a22 、R a23 and R a25 each independently represents a carboxy group, a cyano group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms. p1 represents any integer from 0 to 5. q1 represents any integer from 0 to 3. r1 represents any integer from 0 to 3. w1 represents any integer from 0 to 8. When p1, q1, r1, and / or w1 is 2 or more, the plurality of R a21 's, R a22 's, R a23 and / or R a25 may be the same as or different from each other.

[0155] R a21 's, R a22 's, R a23 and R a25 Examples of the aliphatic hydrocarbon group in include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, and tert-butyl group. R a18 's, R a19 's, R a20 and R a24 Examples of the halogen atom in include fluorine atom, chlorine atom, bromine atom, and iodine atom. R a18 's, R a19 's, R a20 and R a24 Examples of the alkyl group in include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group, etc., preferably an alkyl group having 1 to 4 carbon atoms, more preferably methyl group or ethyl group. R a18 's, R a19 's, R a20 and R a24Examples of alkyl groups having halogen atoms in this context include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, perfluorohexyl, trichloromethyl, tribromomethyl, and triiodomethyl groups. L a8 and L a9 Examples of alkanediyl groups in this compound include methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl.

[0156] In equations (a3-1) to (a3-3), L a4 ~L a6 Each is independently, preferably -O- or *-O-(CH2) k3 In -CO-O-, k3 is an integer from 1 to 4, more preferably -O- and *-O-CH2-CO-O-, and even more preferably an oxygen atom. R a18 ~R a21 The group is preferably a methyl group. R a22 and R a23 Each of these is independently preferably a carboxyl group, a cyano group, or a methyl group. p1, q1, and r1 are each independently, preferably integers from 0 to 2, and more preferably 0 or 1.

[0157] In equation (a3-4), R a24 Preferably, it is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group, or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a25The group is preferably a carboxyl group, a cyano group, or a methyl group. L a7 Preferably -O- or *-OL a8 It is -CO-O-, and more preferably -O-, -O-CH2-CO-O-, or -O-C2H4-CO-O-. w1 is preferably an integer between 0 and 2, and more preferably 0 or 1. In particular, formula (a3-4)' is preferred over formula (a3-4). TIFF2023156258000106.tif4051(in the formula, R a24 , L a7 (This expresses the same meaning as above.)

[0158] Examples of structural units (a3) ​​include those derived from monomers described in Japanese Patent Publication No. 2010-204646, Japanese Patent Publication No. 2000-122294, and Japanese Patent Publication No. 2012-41274. Examples of structural units (a3) ​​include those represented by any of the formulas (a3-1-1), (a3-1-2), (a3-2-1), (a3-2-2), (a3-3-1), (a3-3-2), and (a3-4-1) to (a3-4-12), and in the said structural units, R in formulas (a3-1) to (a3-4). a18 , R a19 , R a20 and R a24 A structural unit in which the corresponding methyl group is replaced by a hydrogen atom is preferred.

[0159] JPEG2023156258000107.jpg115165 When resin (A) contains structural units (a3), the total content is 1 mol% or more, preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, relative to the total structural units of resin (A). Also, it is 70 mol% or less, preferably 65 mol% or less, and more preferably 60 mol% or less. Specifically, it is 1 to 70 mol%, preferably 3 to 65 mol%, and more preferably 5 to 60 mol%. Furthermore, the content of structural unit (a3-1), structural unit (a3-2), structural unit (a3-3), or structural unit (a3-4) is preferably 1 mol% or more, more preferably 3 mol% or more, and even more preferably 5 mol% or more, relative to the total structural units of resin (A). Also preferably 60 mol% or less, more preferably 55 mol% or less, and even more preferably 50 mol% or less. Specifically, 1 to 60 mol% is preferred, 3 to 55 mol% is more preferred, and 5 to 50 mol% is even more preferred.

[0160] <Structural Unit (a4)> The following are examples of structural units (a4): TIFF2023156258000108.tif3066[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 This represents a saturated hydrocarbon group having 1 to 24 fluorine atoms, and the -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. R 42 Saturated hydrocarbon groups represented by include chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these.

[0161] Examples of chain-like hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl groups. Examples of monocyclic or polycyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; and polycyclic alicyclic hydrocarbon groups such as decahydronaphthyl, adamantyl, norbornyl, and the following groups (* indicates a bonding site). TIFF2023156258000109.tif11159 Examples of groups formed by combinations include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic hydrocarbon group-alkyl group.

[0162] Examples of structural units (a4) include structural units represented by at least one selected from the group consisting of formulas (a4-0), (a4-1), (a4-2), (a4-3), and (a4-4). TIFF2023156258000110.tif4652[In formula (a4-0), R 5 represents a hydrogen atom or a methyl group. L 4a This represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 4 carbon atoms. L 3a This represents a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluorocycloalkanediyl group having 3 to 12 carbon atoms. R 6 This represents a hydrogen atom or a fluorine atom.

[0163] L 4a Examples of divalent aliphatic saturated hydrocarbon groups in this context include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, and butane-1,4-diyl, and branched alkanediyl groups such as ethane-1,1-diyl, propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1,3-diyl, and 2-methylpropane-1,2-diyl. L 3aThe perfluoroalkanediyl groups in this product include difluoromethylene, perfluoroethylene, perfluoropropane-1,1-diyl, perfluoropropane-1,3-diyl, perfluoropropane-1,2-diyl, perfluoropropane-2,2-diyl, perfluorobutane-1,4-diyl, perfluorobutane-2,2-diyl, perfluorobutane-1,2-diyl, perfluoropentane-1,5-diyl, perfluoropentane-2,2-diyl, and perfluoropentane-3 Examples include 3-diyl group, perfluorohexane-1,6-diyl group, perfluorohexane-2,2-diyl group, perfluorohexane-3,3-diyl group, perfluoroheptane-1,7-diyl group, perfluoroheptane-2,2-diyl group, perfluoroheptane-3,4-diyl group, perfluoroheptane-4,4-diyl group, perfluorooctane-1,8-diyl group, perfluorooctane-2,2-diyl group, perfluorooctane-3,3-diyl group, and perfluorooctane-4,4-diyl group. L 3a Examples of perfluorocycloalkanediyl groups in this context include perfluorocyclohexanediyl group, perfluorocyclopentanediyl group, perfluorocycloheptanediyl group, and perfluoroadamantanediyl group.

[0164] L 4a Preferably, it is a single bond, a methylene group, or an ethylene group, and more preferably a single bond and a methylene group. L 3a The group is preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0165] The structural units (a4-0) are the structural units shown below and the R in the structural units (a4-0) within the structural units below. 5 One example is a structural unit in which the corresponding methyl group is replaced by a hydrogen atom. TIFF2023156258000111.tif100170

[0166] TIFF2023156258000112.tif4670[In formula (a4-1), R a41 represents a hydrogen atom or a methyl group. R a42 represents a saturated hydrocarbon group having 1 to 20 carbon atoms, which may have substituents, and the -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. A a41 This represents an alkanediyl group having 1 to 6 carbon atoms, which may have substituents, or a group represented by formula (a-g1). However, A a41 and R a42 At least one of these atoms has a halogen atom (preferably a fluorine atom) as a substituent. TIFF2023156258000113.tif1384 [In formula (a-g1), s represents either 0 or 1. A a42 and A a44 Each of these independently represents a divalent saturated hydrocarbon group having 1 to 5 carbon atoms, which may have substituents. A a43 This represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, which may have single bonds or substituents. X a41 and X a42 These represent -O-, -CO-, -CO-O-, or -O-CO-, respectively, independently. However, A a42 , A a43 , A a44 , X a41 and X a42 The total number of carbon atoms is 7 or less. * indicates a binding site, and the * on the right is -O-CO-R a42 This is the junction site.

[0167] R a42 Examples of saturated hydrocarbon groups in this context include chain-type saturated hydrocarbon groups, monocyclic or polycyclic alicyclic saturated hydrocarbon groups, and groups formed by combining these. Examples of chain-type saturated hydrocarbon groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl groups. Examples of monocyclic or polycyclic alicyclic saturated hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; and polycyclic alicyclic saturated hydrocarbon groups such as decahydronaphthyl, adamantyl, norbornyl, and the following groups (* indicates the bonding site). TIFF2023156258000114.tif11159 Examples of groups formed by combinations include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic saturated hydrocarbon groups, such as -alkanediyl group-alicyclic saturated hydrocarbon group, -alicyclic saturated hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic saturated hydrocarbon group-alkyl group.

[0168] R a42 The substituents that may be present include at least one selected from halogen atoms and groups represented by formula (a-g3). Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms being preferred. TIFF2023156258000115.tif965[In formula (a-g3), X a43 * represents an oxygen atom, a carbonyl group, *-O-CO-, or *-CO-O-. A a45 * represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms, which may contain a halogen atom. a42 This represents the connection point with [the other element]. However, R a42 -X a43 -A a45 In R a42 If it does not have a halogen atom, then A a45 This represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms and containing at least one halogen atom.

[0169] A a45 Examples of the aliphatic hydrocarbon group in [A] include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, pentadecyl group, hexadecyl group, heptadecyl group, and octadecyl group; monocyclic alicyclic hydrocarbon groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group; and polycyclic alicyclic hydrocarbon groups such as decahydronaphthyl group, adamantyl group, norbornyl group, and the following group (* represents the bonding site). Examples of the group formed by the combination of [TIFF2023156258000116.tif11159] include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, -alkanediyl group-alicyclic hydrocarbon group-alkyl group, and the like.

[0170] R a42 is preferably an aliphatic hydrocarbon group which may have a halogen atom, more preferably an alkyl group having a halogen atom and / or an aliphatic hydrocarbon group having a group represented by the formula (a-g3). R a42 When [R] is an aliphatic hydrocarbon group having a halogen atom, it is preferably an aliphatic hydrocarbon group having a fluorine atom, more preferably a perfluoroalkyl group or a perfluorocycloalkyl group, still more preferably a perfluoroalkyl group having 1 to 6 carbon atoms, and particularly preferably a perfluoroalkyl group having 1 to 3 carbon atoms. Examples of the perfluoroalkyl group include perfluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, and perfluorooctyl group. Examples of the perfluorocycloalkyl group include perfluorocyclohexyl group. R a42However, if it is an aliphatic hydrocarbon group having a group represented by formula (a-g3), then R is calculated including the number of carbon atoms in the group represented by formula (a-g3). a42 The total number of carbon atoms is preferably 15 or less, and more preferably 12 or less. If the atom has a substituent represented by formula (a-g3), the number of substituents is preferably one.

[0171] R a42 If R is an aliphatic hydrocarbon group having a group represented by formula (a-g3), a42 More preferably, the group is represented by formula (a-g2). TIFF2023156258000117.tif879[In formula (a-g2), A a46 This represents a divalent aliphatic hydrocarbon group having 1 to 17 carbon atoms, which may contain a halogen atom. X a44 This represents **-O-CO- or **-CO-O- (where ** is A a46 (This represents the connection site with [the other element].) A a47 This represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms, which may contain a halogen atom. However, A a46 , A a47 and X a44 The total number of carbon atoms is 18 or less, A a46 and A a47 At least one of them has at least one halogen atom. * indicates a bonding site with a carbonyl group.

[0172] A a46 The aliphatic hydrocarbon group preferably has 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. A a47 The number of carbon atoms in the aliphatic hydrocarbon group is preferably 4 to 15, more preferably 5 to 12, A a47 A cyclohexyl group or an adamantyl group is more preferable.

[0173] The preferred structure of the group represented by formula (a-g2) is as follows (* indicates the bonding site with the carbonyl group). JPEG2023156258000118.jpg13161

[0174] A a41 Examples of alkanediyl groups in this context include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and hexane-1,6-diyl group; and branched alkanediyl groups such as propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-methylbutane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. A a41 Examples of substituents on the alkanediyl group include hydroxyl groups and alkoxy groups having 1 to 6 carbon atoms. A a41 The group is preferably an alkanediyl group having 1 to 4 carbon atoms, more preferably an alkanediyl group having 2 to 4 carbon atoms, and even more preferably an ethylene group.

[0175] A in the group represented by formula (a-g1) a42 , A a43 and A a44 Examples of divalent saturated hydrocarbon groups represented by include linear or branched alkanediyl groups and monocyclic or polycyclic divalent alicyclic hydrocarbon groups, as well as groups formed by combining alkanediyl groups and divalent alicyclic hydrocarbon groups. Specifically, examples include methylene groups, ethylene groups, propane-1,3-diyl groups, propane-1,2-diyl groups, butane-1,4-diyl groups, 1-methylpropane-1,3-diyl groups, 2-methylpropane-1,3-diyl groups, and 2-methylpropane-1,2-diyl groups. A a42 , A a43 and A a44 Examples of substituents on the divalent saturated hydrocarbon group represented by include hydroxyl groups and alkoxy groups having 1 to 6 carbon atoms. s is preferably 0.

[0176] In the group represented by formula (a-g1), X a42The following are examples of groups whose -O-, -CO-, -CO-O-, or -O-CO-. In the following examples, * and ** represent the bonding site, and ** is -O-CO-R a42 This is the junction site. TIFF2023156258000119.tif54162

[0177] The structural units represented by formula (a4-1) are the structural units shown below and the R in the structural units represented by formula (a4-1) in the structural units below. a41 One example is a structural unit in which the corresponding methyl group is replaced by a hydrogen atom. JPEG2023156258000120.jpg167144

[0178] TIFF2023156258000121.tif66133

[0179] The structural unit represented by formula (a4-1) is preferably the structural unit represented by formula (a4-2). TIFF2023156258000122.tif4365[In formula (a4-2), R f5 represents a hydrogen atom or a methyl group. L 44 This represents an alkanediyl group having 1 to 6 carbon atoms, and the -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-. R f6 This represents a saturated hydrocarbon group having 1 to 20 fluorine atoms. However, L 44 and R f6 The upper limit for the total number of carbon atoms is 21.

[0180] L 44 The alkanediyl group with 1 to 6 carbon atoms is A a41 Examples of groups similar to those exemplified by the alkanediyl group in [reference] include [example]. R f6 The saturated hydrocarbon group is R a42 Similar to the examples given earlier, the same types of bases can be cited. L44 In this compound, the alkanediyl group having 1 to 6 carbon atoms is preferably an alkanediyl group having 2 to 4 carbon atoms, and more preferably an ethylene group.

[0181] Examples of structural units represented by equation (a4-2) include those represented by equations (a4-1-1) to (a4-1-11), respectively. f5 A structural unit in which the corresponding methyl group is replaced by a hydrogen atom can also be cited as a structural unit represented by formula (a4-2).

[0182] An example of a structural unit (a4) is the structural unit represented by formula (a4-3). TIFF2023156258000123.tif5771[In formula (a4-3), R f7 represents a hydrogen atom or a methyl group. L 5 This represents an alkanediyl group with 1 to 6 carbon atoms. A f13 This represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, which may contain a fluorine atom. X f12 This represents *-O-CO- or *-CO-O- (* is A f13 This represents the connection site. A f14 This represents a saturated hydrocarbon group having 1 to 17 carbon atoms, which may contain a fluorine atom. However, A f13 and A f14 At least one of them has a fluorine atom, L 5 , A f13 and A f14 The upper limit for the total number of carbon atoms is 20.

[0183] L 5 The alkanediyl group in A is a41 Examples of such groups include those similar to the alkanediyl group in the divalent saturated hydrocarbon group. A f13The divalent saturated hydrocarbon group which may have a fluorine atom is preferably a divalent chain saturated hydrocarbon group which may have a fluorine atom and a divalent alicyclic saturated hydrocarbon group which may have a fluorine atom, and more preferably a perfluoroalkanediyl group. Examples of divalent chain-type saturated hydrocarbon groups that may contain a fluorine atom include methylene groups, ethylene groups, propanediyl groups, butanediyl groups, and pentanediyl groups, as well as perfluoroalkanediyl groups such as difluoromethylene groups, perfluoroethylene groups, perfluoropropanediyl groups, perfluorobutanediyl groups, and perfluoropentanediyl groups. The divalent alicyclic saturated hydrocarbon group, which may contain a fluorine atom, may be monocyclic or polycyclic. Examples of monocyclic groups include cyclohexanediyl and perfluorocyclohexanediyl groups. Examples of polycyclic groups include adamantanediyl, norbornanediyl, and perfluoroadamantanediyl groups. A f14 The saturated hydrocarbon group and the saturated hydrocarbon group which may have a fluorine atom are R a42 The same groups as those exemplified above can be cited. Among them, trifluoromethyl group, difluoromethyl group, methyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, ethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, butyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, pentyl group, Preferred groups include alkyl fluorides such as hexyl group, perfluorohexyl group, heptyl group, perfluoroheptyl group, octyl group, and perfluorooctyl group, cyclopropylmethyl group, cyclopropyl group, cyclobutylmethyl group, cyclopentyl group, cyclohexyl group, perfluorocyclohexyl group, adamantyl group, adamantylmethyl group, adamantyldimethyl group, norbornyl group, norbornylmethyl group, perfluoroadamantyl group, and perfluoroadamantylmethyl group.

[0184] In equation (a4-3), L 5 An ethylene group is preferred. A f13 The divalent saturated hydrocarbon group is preferably a group containing a divalent chain saturated hydrocarbon group having 1 to 6 carbon atoms and a divalent alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a divalent chain saturated hydrocarbon group having 2 to 3 carbon atoms. A f14 The saturated hydrocarbon group is preferably a group containing a chain-type saturated hydrocarbon group having 3 to 12 carbon atoms and an alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a group containing a chain-type saturated hydrocarbon group having 3 to 10 carbon atoms and an alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms. Among these, A f14 The group is preferably a group containing an alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a cyclopropylmethyl group, a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group.

[0185] Examples of structural units represented by equation (a4-3) include those represented by equations (a4-1'-1) to (a4-1'-11), respectively. f7 A structural unit in which the corresponding methyl group is replaced by a hydrogen atom can also be cited as a structural unit represented by formula (a4-3).

[0186] As a structural unit (a4), the structural unit represented by formula (a4-4) can also be cited. TIFF2023156258000124.tif4466[In formula (a4-4), R f21 represents a hydrogen atom or a methyl group. A f21 is, -(CH2) j1 -,-(CH2) j2 -O-(CH2) j3 - or - (CH2) j4 -CO-O-(CH2) j5 - represents j1 through j5 each independently represent an integer from 1 to 6. Rf22 This represents a saturated hydrocarbon group with 1 to 10 carbon atoms containing a fluorine atom.

[0187] R f22 The saturated hydrocarbon group is R a42 Examples include the same saturated hydrocarbon group represented by R. f22 The C1-C10 alkyl group having a fluorine atom or the C1-C10 alicyclic hydrocarbon group having a fluorine atom is preferred, the C1-C10 alkyl group having a fluorine atom is more preferred, and the C1-C6 alkyl group having a fluorine atom is even more preferred.

[0188] In equation (a4-4), A f21 As for, -(CH2) j1 - is preferred, an ethylene group or a methylene group is more preferred, and a methylene group is even more preferred.

[0189] As a structural unit represented by formula (a4-4), for example, the following structural unit and the structural unit represented by the following formula, R in structural unit (a4-4) f21 One example is a structural unit in which the corresponding methyl group is replaced by a hydrogen atom. TIFF2023156258000125.tif87160

[0190] If resin (A) contains structural units (a4), the content of these units is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and even more preferably 3 to 10 mol%, relative to the total structural units of resin (A).

[0191] <Structural Unit (a5)> Examples of non-eliminating hydrocarbon groups in structural unit (a5) include groups having linear, branched, or cyclic hydrocarbon groups. Among these, structural unit (a5) is preferably a group having an alicyclic hydrocarbon group. An example of a structural unit (a5) is the structural unit represented by formula (a5-1). TIFF2023156258000126.tif3971[In formula (a5-1), R51 represents a hydrogen atom or a methyl group. R 52 This represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and the hydrogen atoms contained in this alicyclic hydrocarbon group may be substituted with an aliphatic hydrocarbon group having 1 to 8 carbon atoms. L 55 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.

[0192] R 52 The alicyclic hydrocarbon group in this compound may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. Examples of polycyclic alicyclic hydrocarbon groups include adamantyl and norbornyl groups. Examples of aliphatic hydrocarbon groups having 1 to 8 carbon atoms include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl. Examples of substituted alicyclic hydrocarbon groups include the 3-methyladamantyl group. R 52 Preferably, it is an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, and more preferably, an adamantyl group, a norbornyl group, or a cyclohexyl group. L 55 Examples of divalent saturated hydrocarbon groups in this context include divalent chain-type saturated hydrocarbon groups and divalent alicyclic saturated hydrocarbon groups, with divalent chain-type saturated hydrocarbon groups being preferred. Examples of divalent chain-type saturated hydrocarbon groups include methylene groups, ethylene groups, propanediyl groups, butanediyl groups, and pentanediyl groups, which are all types of alkanediyl groups. The divalent alicyclic saturated hydrocarbon group may be monocyclic or polycyclic. Examples of monocyclic alicyclic saturated hydrocarbon groups include cycloalkanediyl groups such as cyclopentanediyl and cyclohexanediyl. Examples of polycyclic divalent alicyclic saturated hydrocarbon groups include adamantanediyl and norbornanediyl.

[0193] L 55 Groups in which the -CH2- contained in the divalent saturated hydrocarbon group represented by is replaced with -O- or -CO- include, for example, the groups represented by formulas (L1-1) to (L1-4). In the following formulas, * and ** represent bonding sites, respectively, and * represents the bonding site with the oxygen atom. TIFF2023156258000127.tif18165[In formula (L1-1), X x1 This represents *-O-CO- or *-CO-O- (* is L x1 This represents the connection site. L x1 This represents a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. L x2 This represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. However, L x1 and L x2 The total number of carbon atoms is 16 or less. In formula (L1-2), L x3 This represents a divalent aliphatic saturated hydrocarbon group with 1 to 17 carbon atoms. L x4 This represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. However, L x3 and L x4 The total number of carbon atoms is 17 or less. In formula (L1-3), L x5 This represents a divalent aliphatic saturated hydrocarbon group with 1 to 15 carbon atoms. L x6 and L x7 Each of these independently represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 14 carbon atoms. However, Lx5 , L x6 and L x7 The total number of carbon atoms is 15 or less. In formula (L1-4), L x8 and L x9 This represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms. W x1 This represents a divalent alicyclic saturated hydrocarbon group with 3 to 15 carbon atoms. However, L x8 , L x9 and W x1 The total number of carbon atoms is 15 or less.

[0194] L x1 Preferably, this is a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x2 Preferably, it is a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond. L x3 Preferably, it is a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x4 Preferably, it is a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 Preferably, this is a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x6 Preferably, it is a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x7 Preferably, it is a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x8 Preferably, it is a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. L x9 Preferably, it is a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. W x1 Preferably, this is a divalent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, more preferably a cyclohexanediyl group or an adamantanediyl group.

[0195] Examples of groups represented by formula (L1-1) include the divalent groups shown below. Examples of groups represented by formula (L1-2) in TIFF2023156258000128.tif36147 include the divalent groups shown below. Examples of groups represented by formula (L1-3) in TIFF2023156258000129.tif23130 include the divalent groups shown below. Examples of groups represented by formula (L1-4) in TIFF2023156258000130.tif16147 include the divalent groups shown below. TIFF2023156258000131.tif13168L 55 Preferably, it is a single bond or a group represented by formula (L1-1).

[0196] The structural units (a5-1) are the structural units shown below and the R in the structural unit (a5-1) within the structural units below. 51 One example is a structural unit in which the corresponding methyl group is replaced by a hydrogen atom. TIFF2023156258000132.tif111150 If resin (A) contains structural units (a5), the content of these units is preferably 1 to 30 mol%, more preferably 2 to 20 mol%, and even more preferably 3 to 15 mol%, relative to the total structural units of resin (A).

[0197] <Structural Unit (a6)> Structural unit (a6) is a structural unit having an -SO2- group, and it is preferable that it has an -SO2- group in its side chain. A structural unit having an -SO2- group may have a linear structure having an -SO2- group, a branched structure having an -SO2- group, or a cyclic structure (monocyclic and polycyclic) having an -SO2- group. Preferably, it is a structural unit having a cyclic structure having an -SO2- group, and more preferably, it is a structural unit having a cyclic structure (sultone ring) containing -SO2-O-.

[0198] As a sultone ring, the following equation (T 1 -1), formula (T 1 -2), formula (T 1 -3) and formula (T 1 A ring represented by (T-4) is an example. The bonding site can be at any position. The sultone ring may be monocyclic, but it is preferably polycyclic. A polycyclic sultone ring means a bridging ring containing -SO2-O- as the atomic group constituting the ring, and is represented by formula (T 1 -1) and formula (T 1 A ring represented by equation (T) is an example. A Sultone ring is given by equation (T 1 As shown in (2), the ring may contain heteroatoms in addition to -SO2-O- as part of the atomic group constituting the ring. Examples of heteroatoms include oxygen atoms, sulfur atoms, or nitrogen atoms, with oxygen atoms being preferred. TIFF2023156258000133.tif3186

[0199] The sultone ring may have substituents, and examples of substituents include C1-C12 alkyl groups which may have a halogen atom or a hydroxyl group, halogen atoms, hydroxyl groups, cyano groups, C1-C12 alkoxy groups, C6-C12 aryl groups, C7-C12 aralkyl groups, glycidyloxy groups, C2-C12 alkoxycarbonyl groups, and C2-C4 alkylcarbonyl groups.

[0200] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. Examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, and decyl groups, preferably alkyl groups having 1 to 6 carbon atoms, and more preferably methyl groups. Examples of alkyl groups having a halogen atom include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, perfluorohexyl, trichloromethyl, tribromomethyl, and triiodomethyl, with trifluoromethyl being preferred. Examples of alkyl groups having a hydroxyl group include hydroxymethyl groups and 2-hydroxyethyl groups. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, and dodecyloxy groups. Examples of aryl groups include phenyl, naphthyl, anthryl, p-methylphenyl, p-tert-butylphenyl, p-adamantylphenyl, tolyl, xylyl, cumyl, mesityl, biphenyl, phenanthryl, 2,6-diethylphenyl, and 2-methyl-6-ethylphenyl. Examples of aralkyl groups include benzyl, phenethyl, phenylpropyl, naphthylmethyl, and naphthylethyl groups. Examples of alkoxycarbonyl groups include groups in which an alkoxy group such as a methoxycarbonyl group or an ethoxycarbonyl group is bonded to a carbonyl group, preferably an alkoxycarbonyl group having 6 or fewer carbon atoms, and more preferably a methoxycarbonyl group. Examples of alkylcarbonyl groups include acetyl, propionyl, and butyryl groups.

[0201] From the viewpoint of ease of production of monomers that lead to structural unit (a6), a sultone ring without substituents is preferred. As the sultone ring, the ring represented by the following formula (T1') is preferred. TIFF2023156258000134.tif3171[In formula (T1'), X 11 represents an oxygen atom, a sulfur atom, or a methylene group. R 41 This represents a C1-C12 alkyl group which may have a halogen atom or a hydroxyl group, a halogen atom, a hydroxyl group, a cyano group, a C1-C12 alkoxy group, a C6-C12 aryl group, a C7-C12 aralkyl group, a glycidyloxy group, a C2-C12 alkoxycarbonyl group, or a C2-C4 alkylcarbonyl group. ma represents an integer from 0 to 9. When ma is 2 or greater, multiple R 41 They may be the same or different. The connection point can be at any location. X 11 This is preferably an oxygen atom or a methylene group, and more preferably a methylene group. R 41 Examples include substituents similar to those of a sultone ring, and C1-C12 alkyl groups which may have a halogen atom or a hydroxyl group are preferred. ma is preferably 0 or 1, and more preferably 0.

[0202] The following rings can be represented by formula (T1'). The bonding site can be at any position. In particular, rings with a bonding site at position 1 or 3 are preferred. TIFF2023156258000135.tif46147

[0203] The structural unit having the -SO2- group preferably further has a group derived from a polymerizable group. Examples of polymerizable groups include vinyl group, acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, acryloylamino group, methacryloylamino group, acryloylthio group, and methacryloylthio group. In particular, the monomer that leads to the structural unit (a6) is preferably a monomer having an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer.

[0204] The structural unit (a6) is preferably a structural unit represented by formula (a6-0). TIFF2023156258000136.tif4964[In formula (a6-0), R x This represents an alkyl group having 1 to 6 carbon atoms, which may contain a halogen atom, a hydrogen atom, or a halogen atom. A xx is an oxygen atom, -N(R c )- or represents a sulfur atom. A x represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the saturated hydrocarbon group is -O-, -CO-, or -N(R d )- may be replaced with this. X 11 , R 41 And ma have the same meaning as above. R c and R d Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0205] R x Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. R x Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl groups, preferably alkyl groups having 1 to 4 carbon atoms, and more preferably methyl or ethyl groups. R xExamples of alkyl groups having a halogen atom include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, perfluorohexyl, trichloromethyl, tribromomethyl, and triiodomethyl. R x Preferably, it is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group, or an ethyl group, and even more preferably a hydrogen atom or a methyl group.

[0206] A x Examples of divalent saturated hydrocarbon groups include linear alkanediyl groups, branched alkanediyl groups, and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups, and combinations of two or more of these groups are also acceptable. Specifically, methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group Linear alkanediyl groups such as dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, heptadecane-1,17-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group, and propane-2,2-diyl group; Branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group; Monocyclic, divalent, alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; Examples include polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group. A x The bond position to the sultone ring can be any position, but it is preferably at position 1.

[0207] The following structural units (a6-0) can be listed: TIFF2023156258000137.tif93150

[0208] In particular, structural units represented by formulas (a6-1), (a6-2), (a6-6), (a6-7), (a6-8), and (a6-12) are preferred, and structural units represented by formulas (a6-1), (a6-2), (a6-7), and (a6-8) are more preferred. If resin (A) contains structural units (a6), the content of these units is preferably 1 to 50 mol%, more preferably 2 to 40 mol%, and even more preferably 3 to 30 mol%, relative to the total structural units of resin (A).

[0209] <Structural Unit (II)> The resin (A) may further contain structural units that decompose upon exposure to generate acid (hereinafter sometimes referred to as "structural unit (II)"). Specifically, structural unit (II) is the structural unit described in Japanese Patent Application Publication No. 2016-79235, and is preferably a structural unit having a sulfonate group or carboxylate group and an organic cation in its side chain, or a structural unit having a sulfonio group and an organic anion in its side chain.

[0210] The structural unit having a sulfonate group or carboxylate group and an organic cation in its side chain is preferably the structural unit represented by formula (II-2-A'). TIFF2023156258000138.tif35104[In formula (II-2-A'), X III3represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the saturated hydrocarbon group may be replaced with -O-, -S-, or -CO-, and the hydrogen atom contained in the saturated hydrocarbon group may be replaced with a halogen atom, an alkyl group having 1 to 6 carbon atoms which may contain a halogen atom, or a hydroxyl group. A x1 This represents an alkanediyl group having 1 to 8 carbon atoms, and the hydrogen atoms contained in the alkanediyl group may be substituted with fluorine atoms or perfluoroalkyl groups having 1 to 6 carbon atoms. RA - This represents a sulfonate group or a carboxylate group. R III3 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. ZA + This represents an organic cation.

[0211] R III3 Examples of halogen atoms represented by this formula include fluorine, chlorine, bromine, and iodine atoms. R III3 A C1-C6 alkyl group which may have a halogen atom represented by R is: a8 Examples include alkyl groups having 1 to 6 carbon atoms that may contain a halogen atom represented by . A x1 Examples of C1-C8 alkanediyl groups represented by include methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. A X1Examples of C1-C6 perfluoroalkyl groups that may be substituted include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, and perfluorohexyl groups. X III3 Examples of divalent saturated hydrocarbon groups having 1 to 18 carbon atoms represented by include linear or branched alkanediyl groups, monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups, and combinations thereof. Specifically, linear alkane diyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, etc.; butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, etc. Examples include branched alkanediyl groups such as pan-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group; cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, and cyclooctane-1,5-diyl group; and divalent polycyclic alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group. Examples of groups in which the -CH2- group in a saturated hydrocarbon group is replaced by -O-, -S-, or -CO- include the divalent groups represented by formulas (X1) to (X53). However, the number of carbon atoms before the -CH2- group in the saturated hydrocarbon group is replaced by -O-, -S-, or -CO- is 17 or less. In the following formulas, * and ** represent bonding sites, and * is A x1 This represents the connection point. JPEG2023156258000139.jpg145161

[0212] X 3 This represents a divalent saturated hydrocarbon group with 1 to 16 carbon atoms. X 4 This represents a divalent saturated hydrocarbon group with 1 to 15 carbon atoms. X 5 This represents a divalent saturated hydrocarbon group with 1 to 13 carbon atoms. X 6 This represents a divalent saturated hydrocarbon group with 1 to 14 carbon atoms. X 7 This represents a trivalent saturated hydrocarbon group with 1 to 14 carbon atoms. X 8 This represents a divalent saturated hydrocarbon group with 1 to 13 carbon atoms.

[0213] ZA in equation (II-2-A') + This is the cation Z1 in the salt represented by formula (B1). + Similar examples include the above.

[0214] The structural unit represented by formula (II-2-A') is preferably the structural unit represented by formula (II-2-A). TIFF2023156258000140.tif38109 [In formula (II-2-A), R III3 , X III3 and ZA + This expresses the same meaning as above. z2A represents an integer between 0 and 6. R III2 and R III4 Each of these independently represents a hydrogen atom, a fluorine atom, or a perfluoroalkyl group having 1 to 6 carbon atoms, and when z2A is 2 or more, multiple R III2 and R III4 They may be the same or they may be different. Q a and Q b Each of these independently represents either a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. R III2 , R III4 Q a and Q bAs perfluoroalkyl groups having 1 to 6 carbon atoms, as represented by the aforementioned Q b1 Examples include perfluoroalkyl groups with 1 to 6 carbon atoms, represented by [the formula shown].

[0215] The structural unit represented by formula (II-2-A) is preferably the structural unit represented by formula (II-2-A-1). TIFF2023156258000141.tif5577 [In formula (II-2-A-1), R III2 , R III3 , R III4 Q a Q b and ZA + This expresses the same meaning as above. R III5 This represents a saturated hydrocarbon group with 1 to 12 carbon atoms. z2A1 represents an integer between 0 and 6. X I2 This represents a divalent saturated hydrocarbon group having 1 to 11 carbon atoms, where the -CH2- group may be replaced with -O-, -S-, or -CO-, and the hydrogen atoms in the saturated hydrocarbon group may be substituted with halogen atoms or hydroxyl groups. R III5 Examples of saturated hydrocarbon groups having 1 to 12 carbon atoms represented by include linear or branched alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl groups. X I2 As a divalent saturated hydrocarbon group represented by , X III3 Examples include divalent saturated hydrocarbon groups represented by .

[0216] As a structural unit represented by formula (II-2-A-1), the structural unit represented by formula (II-2-A-2) is even more preferable. TIFF2023156258000142.tif5287 [In formula (II-2-A-2), R III3 , RIII5 and ZA + This expresses the same meaning as above. m and nA independently represent either 1 or 2.

[0217] Examples of structural units represented by formula (II-2-A') include the following structural unit, R III3 Examples include structural units in which the group corresponding to the methyl group is replaced by a hydrogen atom, a halogen atom (e.g., a fluorine atom), or a C1-C6 alkyl group which may have a halogen atom (e.g., a trifluoromethyl group), and structural units described in International Publication No. 2012 / 050015. ZA + This represents an organic cation. TIFF2023156258000143.tif86163

[0218] The structural unit having a sulfonio group and an organic anion in its side chain is preferably the structural unit represented by formula (II-1-1). JPEG2023156258000144.jpg3791 [In formula (II-1-1), A II1 This represents a single bond or a divalent linking group. R II1 This represents a divalent aromatic hydrocarbon group with 6 to 18 carbon atoms. R II2 and R II3 Each of these independently represents a hydrocarbon group with 1 to 18 carbon atoms, and R II2 and R II3 These atoms may bond to each other, forming a ring with the sulfur atom to which they are bonded. R II4 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. A - This represents an organic anion. R II1 Examples of divalent aromatic hydrocarbon groups having 6 to 18 carbon atoms, represented by this formula, include phenylene groups and naphthylene groups. R II2 and R II3Examples of hydrocarbon groups represented by this symbol include alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. Examples of alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these are the same as those described above. R II4 Examples of halogen atoms represented by this formula include fluorine, chlorine, bromine, and iodine atoms. R II4 A C1-C6 alkyl group which may have a halogen atom represented by R is: a8 Examples include alkyl groups having 1 to 6 carbon atoms that may contain a halogen atom represented by . A II1 Examples of divalent linking groups represented by include divalent saturated hydrocarbon groups having 1 to 18 carbon atoms, and the -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O-, -S-, or -CO-. Specifically, X III3 Examples include divalent saturated hydrocarbon groups with 1 to 18 carbon atoms, represented by .

[0219] The structural units containing cations in formula (II-1-1) are the structural units represented below and R II4 Examples include structural units in which the group corresponding to the methyl group is replaced by a hydrogen atom, a halogen atom (e.g., a fluorine atom), or a C1-C6 alkyl group that may have a halogen atom (e.g., a trifluoromethyl group). TIFF2023156258000145.tif72163

[0220] A - Examples of organic anions represented by include sulfonic acid anions, sulfonylimide anions, sulfonylmethide anions, and carboxylic acid anions. -The organic anion represented by is preferably a sulfonate anion, and more preferably a sulfonate anion that is contained in the salt represented by the above formula (B1). The sulfonylimide anion and sulfonylmethide anion are anions AI contained in the salt represented by the above formula (I). - It is more preferable that this is the case. Examples of carboxylic acid anions include the following: JPEG2023156258000146.jpg43155

[0221] Examples of structural units represented by formula (II-1-1) include the following structural units: JPEG2023156258000147.jpg88149

[0222] When resin (A) contains structural unit (II), the content of structural unit (II) is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and even more preferably 3 to 10 mol%, relative to the total structural units of resin (A).

[0223] The resin (A) may contain structural units other than those described above, and examples of such structural units include structural units well known in the art.

[0224] The resin (A) is preferably a resin consisting of structural units (a1) and structural units (s), that is, a copolymer of monomer (a1) and monomer (s). Structural unit (a1) is preferably at least one selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2) (preferably a structural unit having a cyclohexyl group or a cyclopentyl group), more preferably at least two, and even more preferably at least two selected from the group consisting of structural unit (a1-1) and structural unit (a1-2). The structural unit (s) is preferably at least one selected from the group consisting of structural units (a2) and structural units (a3). The structural unit (a2) is preferably structural unit (a2-1) or structural unit (a2-A). The structural unit (a3) ​​is preferably at least one selected from the group consisting of structural units represented by formula (a3-1), structural units represented by formula (a3-2), and structural units represented by formula (a3-4). Each structural unit constituting resin (A) may be used individually or in combination of two or more types, and these structural units can be produced by known polymerization methods (e.g., radical polymerization) using monomers that derive these structural units. The content of each structural unit in resin (A) can be adjusted by the amount of monomer used in polymerization. The weight-average molecular weight of resin (A) is preferably 2,000 or more (more preferably 2,500 or more, even more preferably 3,000 or more) and 50,000 or less (more preferably 30,000 or less, even more preferably 15,000 or less). In this specification, the weight-average molecular weight is the value obtained by gel permeation chromatography under the conditions described in the examples.

[0225] <Resins other than resin (A)> The resist composition of the present invention may also contain resins other than resin (A). Examples of resins other than resin (A) include resins containing structural unit (a4) or structural unit (a5) (hereinafter sometimes referred to as resin (X)). Among the resins (X), resins containing structural units (a4) are preferred. Structural units that resin (X) may further have include structural unit (a1), structural unit (a2), structural unit (a3), and structural units derived from other known monomers. In particular, it is preferable that resin (X) consists only of structural unit (a4) and / or structural unit (a5). When resin (X) contains structural unit (a4), the content of structural unit (a4) in resin (X) is preferably 20 mol% or more, more preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more, relative to the total amount of all structural units in resin (X). Also, it is preferably 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, even more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, it is preferably 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, even more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. When resin (X) contains structural unit (a5), the content of structural unit (a5) is preferably 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more, relative to the total amount of all structural units in resin (X). Furthermore, a value of 100 mol% or less is cited, preferably 80 mol% or less, more preferably 70 mol% or less, even more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, a value of 20 to 100 mol% is cited, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, even more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. Also, if the resin (X) contains structural units (a4) and structural units (a5), the total content of structural units (a4) and structural units (a5) is cited as 40 mol% or more, preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more, relative to the total of all structural units of the resin (X). Furthermore, a value of 100 mol% or less is cited. Specifically, a value of 40 to 100 mol% is cited, preferably 60 to 100 mol%, more preferably 70 to 100 mol%, and even more preferably 80 to 100 mol%. Each structural unit constituting resin (X) may be used individually or in combination of two or more types, and these structural units can be produced by known polymerization methods (e.g., radical polymerization) using monomers that induce these structural units. The content of each structural unit in resin (X) can be adjusted by the amount of monomer used in polymerization. The weight-average molecular weight of resin (X) is preferably 6,000 or more (more preferably 7,000 or more) and 80,000 or less (more preferably 60,000 or less). The means for measuring the weight-average molecular weight of resin (X) is the same as in the case of resin (A).

[0226] If the resist composition of the present invention contains resin (X), the amount of resin (X) is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, even more preferably 1 to 40 parts by mass, even more preferably 1 to 30 parts by mass, and even more preferably 1 to 8 parts by mass, per 100 parts by mass of resin (A).

[0227] The content of resin (A) in the resist composition is preferably 80% to 99% by mass, and more preferably 90% to 99% by mass, relative to the solid content of the resist composition. Furthermore, if resins other than resin (A) are included, the total content of resin (A) and the other resins is preferably 80% to 99% by mass, and more preferably 90% to 99% by mass, relative to the solid content of the resist composition. In this specification, "solid content of the resist composition" means the total amount of components of the resist composition excluding the solvent (E), which will be described later. The solid content of the resist composition and the resin content thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0228] <Solvent (E)> The solvent (E) content in the resist composition is usually 90% to 99.9% by mass, preferably 92% to 99% by mass, and more preferably 94% to 99% by mass. The solvent (E) content can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0229] Examples of solvent (E) include glycol ether esters such as ethyl cellosolve acetate, methyl cellosolve acetate, and propylene glycol monomethyl ether acetate; glycol ethers such as propylene glycol monomethyl ether; esters such as ethyl lactate, butyl acetate, amyl acetate, and ethyl pyruvate; ketones such as acetone, methyl isobutyl ketone, 2-heptanone, and cyclohexanone; and cyclic esters such as γ-butyrolactone. One of solvents (E) may be used alone, or two or more may be used.

[0230] <Quencher (C)> Quencher (C) can be a basic nitrogen-containing organic compound or a salt that generates an acid weaker than the acid generated from salts used as an acid generator (such as salt (I) and salt (B1)). When the resist composition contains quencher (C), the quencher (C) content is preferably about 0.01 to 15% by mass, more preferably about 0.01 to 10% by mass, even more preferably about 0.1 to 8% by mass, and even more preferably about 0.1 to 7% by mass, based on the solid content of the resist composition. Basic nitrogen-containing organic compounds include amines and ammonium salts. Amines include aliphatic amines and aromatic amines. Aliphatic amines include primary amines, secondary amines, and tertiary amines.

[0231] Examples of amines include 1-naphthylamine, 2-naphthylamine, aniline, diisopropylaniline, 2-,3- or 4-methylaniline, 4-nitroaniline, N-methylaniline, N,N-dimethylaniline, diphenylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, triethylamine, trimethylamine, tripropylamine, trib Tylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, methyldibutylamine, methyldipentylamine, methyldihexylamine, methyldicyclohexylamine, methyldiheptylamine, methyldioctylamine, methyldinonylamine, methyldidecylamine, ethyldibutylamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine, ethyldioctylamine, ethyldinonylamine, ethyldi Decylamine, dicyclohexylmethylamine, tris[2-(2-methoxyethoxy)ethyl]amine, triisopropanolamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4'-diamino-1,2-diphenylethane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 4,4'-diamino-3,3'-diethyldiphenylmethane, 2,2'-methylenebisaniline, imidazole, 4-methylimidazole, pyridine, 4-methylpyridine, 1,2-di(2-P Examples include lysyl)ethane, 1,2-di(4-pyridyl)ethane, 1,2-di(2-pyridyl)ethene, 1,2-di(4-pyridyl)ethene, 1,3-di(4-pyridyl)propane, 1,2-di(4-pyridyloxy)ethane, di(2-pyridyl)ketone, 4,4'-dipyridyl sulfide, 4,4'-dipyridyl disulfide, 2,2'-dipyridylamine, 2,2'-dipicolylamine, bipyridine, etc. Diisopropylaniline is preferred, and 2,6-diisopropylaniline is more preferred.

[0232] Examples of the ammonium salt include tetramethylammonium hydroxide, tetraisopropylammonium hydroxide, tetrabutylammonium hydroxide, tetrahexylammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethylammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium hydroxide, tetra-n-butylammonium salicylate, choline, and the like.

[0233] The acidity of a salt that generates an acid with a lower acidity than the acid generated from the acid generator is represented by the acid dissociation constant (pKa). A salt that generates an acid with a lower acidity than the acid generated from the acid generator is a salt having an acid dissociation constant of the acid generated from the salt usually of -3 < pKa, preferably -1 < pKa < 7, and more preferably 0 < pKa < 5. Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator include a salt represented by the following formula, a salt represented by formula (D) described in JP-A No. 2015-147926 (hereinafter sometimes referred to as "weak acid inner salt (D)"), and salts described in JP-A No. Nos. 2012-229206, 2012-6908, 2012-72109, 2011-39502, and 2011-191745. The salt that generates an acid with a lower acidity than the acid generated from the acid generator is preferably a salt that generates a carboxylic acid with a lower acidity than the acid generated from the acid generator (a salt having a carboxylic acid anion), more preferably a weak acid inner salt (D), and still more preferably a diphenyliodonium salt containing a phenyl group substituted with a carboxylic acid anion among the weak acid inner salts (D). TIFF2023156258000148.tif98153

[0234] The weak acid inner salt (D) is preferably a diphenyliodonium salt having an iodonium cation to which two phenyl groups are bonded and a carboxylic acid anion substituted on at least one of the two phenyl groups bonded to the iodonium cation, and specifically, salts represented by the following formulas can be mentioned.

[0235] TIFF2023156258000149.tif2362[In formula (D), R D1 and R D2 Each of these independently represents a hydrocarbon group having 1 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 7 carbon atoms, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a nitro group, or a halogen atom. m' and n' each independently represent an integer from 0 to 4, and if m' is 2 or greater, multiple R D1 They may be the same or different, and if n' is 2 or more, multiple R D2 They may be the same or different. R D1 and R D2 Examples of hydrocarbon groups include chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. Examples of chain-type hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, and nonyl groups. The alicyclic hydrocarbon group may be monocyclic or polycyclic, and may be saturated or unsaturated. Examples include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclononyl, and cyclododecyl groups, as well as norbonyl and adamantyl groups. Examples of aromatic hydrocarbon groups include phenyl group, 1-naphthyl group, 2-naphthyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, 4-propylphenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-t-butylphenyl group, 4-hexylphenyl group, 4-cyclohexylphenyl group, anthryl group, p-adamantylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, biphenyl group, phenanthryl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, and other aryl groups. Groups formed by combining these include alkyl-cycloalkyl groups, cycloalkyl-alkyl groups, and aralkyl groups (for example, phenylmethyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl-1-propyl group, 1-phenyl-2-propyl group, 2-phenyl-2-propyl group, 3-phenyl-1-propyl group, 4-phenyl-1-butyl group, 5-phenyl-1-pentyl group, 6-phenyl-1-hexyl group, etc.). Examples of alkoxy groups include methoxy groups and ethoxy groups. Examples of acyl groups include acetyl groups, propanoyl groups, benzoyl groups, and cyclohexanecarbonyl groups. Examples of acyloxy groups include groups in which an oxy group (-O-) is bonded to the above-mentioned acyl group. Examples of alkoxycarbonyl groups include groups in which a carbonyl group (-CO-) is bonded to the above-mentioned alkoxy group. Examples of halogen atoms include fluorine, chlorine, and bromine atoms. R D1 and R D2 Each of these is preferably an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 4 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 4 carbon atoms, a nitro group, or a halogen atom. m' and n' are each independently preferably integers between 0 and 2, and more preferably 0. If m' is 2 or greater, multiple R D1 They may be the same or different, and if n' is 2 or more, multiple R D2 They may be the same or different.

[0236] More specifically, the following salts are examples: TIFF2023156258000150.tif72165

[0237] <Other ingredients> The resist composition of the present invention may optionally contain components other than those described above (hereinafter sometimes referred to as "other components (F)"). There are no particular limitations on other components (F), and additives known in the resist field, such as sensitizers, dissolution inhibitors, surfactants, stabilizers, dyes, etc., can be used.

[0238] <Preparation of resist composition> The resist composition of the present invention can be prepared by mixing a salt (I) and, optionally, a resin (A), an acid generator (B), a resin other than resin (A), a solvent (E), a quencher (C), and other components (F). The mixing order is arbitrary and not particularly limited. The mixing temperature can be selected from 10 to 40°C, depending on the type of resin, etc., and the solubility of the resin, etc., in the solvent (E). The mixing time can be selected from 0.5 to 24 hours, depending on the mixing temperature. There are no particular restrictions on the mixing method, and stirring or other methods can be used. After mixing the components, it is preferable to filter the mixture using a filter with a pore size of approximately 0.003 to 0.2 μm.

[0239] <Method for manufacturing resist patterns> The method for manufacturing a resist pattern of the present invention is: (1) A step of applying the resist composition of the present invention onto a substrate, (2) A step of drying the applied composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the composition layer after exposure, (5) Includes a step of developing the composition layer after heating. The resist composition can be applied to a substrate using commonly used equipment such as a spin coater. Examples of substrates include inorganic substrates such as silicon wafers, and organic substrates with a resist film or the like formed on their surface. Before applying the resist composition, the substrate may be cleaned, or an anti-reflective film or the like may be formed on the substrate. The solvent is removed and a composition layer is formed by drying the coated composition. Drying is performed, for example, by evaporating the solvent using a heating device such as a hot plate (so-called pre-baking), or by using a vacuum device. The heating temperature is preferably 50 to 200°C, and the heating time is preferably 10 to 180 seconds. The pressure when drying under reduced pressure is 1 to 1.0 × 10⁻⁶. 5 It is preferable that the pressure be around Pa. The resulting composition layer is typically exposed using an exposure machine. The exposure machine may be an immersion exposure machine. Various types of exposure light sources can be used, including those that emit ultraviolet laser light such as KrF excimer lasers (wavelength 248 nm), ArF excimer lasers (wavelength 193 nm), and F2 excimer lasers (wavelength 157 nm), those that emit far-ultraviolet or vacuum-ultraviolet harmonic laser light by wavelength conversion of laser light from a solid-state laser light source (such as a YAG or semiconductor laser), electron beams, and those that irradiate with ultra-ultraviolet (EUV) light. In this specification, the irradiation of these radiations is sometimes collectively referred to as "exposure." During exposure, exposure is usually performed through a mask corresponding to the desired pattern. If the exposure light source is an electron beam, exposure may be performed by direct drawing without using a mask. The composition layer after exposure is subjected to heat treatment (so-called post-exposure bake) to promote the deprotection reaction at acid-unstable groups. The heating temperature is usually around 50 to 200°C, preferably around 70 to 150°C. After heating, a chemical treatment (silylation) may be performed to adjust the hydrophilicity or hydrophobicity of the resin on the surface side of the composition. Alternatively, before development, the process of coating the resist composition, drying, exposure, and heating may be repeated on the composition layer after exposure. The heated composition layer is typically developed using a developing apparatus and a developing solution. Development methods include the dip method, paddle method, spray method, and dynamic dispensing method. The development temperature is preferably, for example, 5 to 60°C, and the development time is preferably, for example, 5 to 300 seconds. By selecting the type of developing solution as described below, a positive-type resist pattern or a negative-type resist pattern can be manufactured. When producing a positive resist pattern from the resist composition of the present invention, an alkaline developer is used as the developer. The alkaline developer can be any alkaline aqueous solution used in this field. For example, aqueous solutions of tetramethylammonium hydroxide or (2-hydroxyethyl)trimethylammonium hydroxide (commonly known as choline) can be used. The alkaline developer may also contain a surfactant. It is preferable to wash the resist pattern with ultrapure water after development, and then remove any remaining water on the substrate and pattern. When manufacturing a negative-type resist pattern from the resist composition of the present invention, a developer containing an organic solvent (hereinafter sometimes referred to as "organic developer") is used as the developer. Examples of organic solvents contained in organic developers include ketone solvents such as 2-hexanone and 2-heptanone; glycol ether ester solvents such as propylene glycol monomethyl ether acetate; ester solvents such as butyl acetate; glycol ether solvents such as propylene glycol monomethyl ether; amide solvents such as N,N-dimethylacetamide; and aromatic hydrocarbon solvents such as anisole. In the organic developer, the content of the organic solvent is preferably 90% by mass or more and 100% by mass or less, more preferably 95% by mass or more and 100% by mass or less, and even more preferably substantially composed of only organic solvents. Among these, organic developers containing butyl acetate and / or 2-heptanone are preferred. The total content of butyl acetate and 2-heptanone in the organic developer is preferably 50% by mass or more and 100% by mass or less, more preferably 90% by mass or more and 100% by mass or less, and even more preferably substantially butyl acetate and / or 2-heptanone alone. Organic developers may contain surfactants. Furthermore, organic developers may contain trace amounts of water. During development, the development process may be stopped by substituting a different type of solvent for the organic developer. It is preferable to wash the developed resist pattern with a rinsing solution. The rinsing solution is not particularly limited as long as it does not dissolve the resist pattern, and a solution containing a general organic solvent can be used, preferably an alcohol solvent or an ester solvent. After cleaning, it is preferable to remove any remaining rinse solution from the substrate and patterns.

[0240] <Application> The resist composition of the present invention is suitable as a resist composition for KrF excimer laser exposure, an ArF excimer laser exposure, an electron beam (EB) exposure, or an EUV exposure, and is particularly suitable as an ArF excimer laser exposure resist composition, and is useful for semiconductor microfabrication. [Examples]

[0241] The present invention will be described in more detail with reference to examples. In the examples, "%" and "parts" representing the content or amount used are based on mass unless otherwise specified. The weight-average molecular weight was determined by gel permulation chromatography. The analytical conditions for gel permulation chromatography are as follows: Column: TSKgel Multipore HXL-M x 3 + guard column (manufactured by Tosoh Corporation) Eluent: Tetrahydrofuran Flow rate: 1.0mL / min Detector: RI detector Column temperature: 40℃ Injection volume: 100μl Molecular weight standard: Standard polystyrene (manufactured by Tosoh Corporation) The structure of the compound was confirmed by measuring the molecular ion peak using mass spectrometry (LC: Agilent 1100, MASS: Agilent LC / MSD). In the following examples, the value of this molecular ion peak is indicated as "MASS".

[0242] Example 1: Synthesis of the salt represented by formula (I-8) JPEG2023156258000151.jpg90165 2.78 parts of the compound represented by formula (I-8-a) and 30 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. After the resulting mixture was cooled to 0°C, 0.30 parts of sodium hydride were mixed and stirred at 0°C for 4 hours. 3.17 parts of the salt represented by formula (I-8-b) were added to the resulting mixture at 0°C and stirred at 0°C for 3 hours to obtain a mixture containing the salt represented by formula (I-8-c). After raising the temperature of the resulting mixture to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then 6.41 parts of the salt represented by formula (I-8-d) were added and stirred at 23°C for 7 hours. 100 parts of chloroform and 30 parts of deionized water were added to the resulting reaction product and stirred at 23°C for 30 minutes, after which the organic layer was separated. To the recovered organic layer, 30 parts of deionized water were added and stirred at 23°C for 30 minutes, after which the organic layer was separated. This washing procedure was repeated 7 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue and stirred at 23°C for 30 minutes, after which the supernatant was removed and concentrated to obtain 1.68 parts of the salt represented by formula (I-8). MASS(ESI(+)Spectrum):M + 539.1 MASS(ESI(-)Spectrum):M - 517.1

[0243] Example 2: Synthesis of the salt represented by formula (I-2) JPEG2023156258000152.jpg87165 2.78 parts of the compound represented by formula (I-8-a) and 30 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. After the resulting mixture was cooled to 0°C, 0.30 parts of sodium hydride were mixed and stirred at 0°C for 4 hours. 3.17 parts of the salt represented by formula (I-8-b) were added to the resulting mixture at 0°C and stirred at 0°C for 3 hours to obtain a mixture containing the salt represented by formula (I-8-c). After raising the temperature of the resulting mixture to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then 4.42 parts of the salt represented by formula (I-2-d) were added and stirred at 23°C for 7 hours. 100 parts of chloroform and 30 parts of deionized water were added to the resulting reaction product and stirred at 23°C for 30 minutes, after which the organic layer was separated. Thirty parts of deionized water were added to the recovered organic layer, and the mixture was stirred at 23°C for 30 minutes. The organic layer was then separated and removed. This washing procedure was repeated seven times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue, and the mixture was stirred at 23°C for 30 minutes. The supernatant was removed and the mixture was concentrated to obtain 1.22 parts of the salt represented by formula (I-2). MASS(ESI(+)Spectrum):M + 539.1 MASS(ESI(-)Spectrum):M - 339.1

[0244] Example 3: Synthesis of the salt represented by formula (I-46) JPEG2023156258000153.jpg92161 Mix 2.92 parts of the compound represented by formula (I-46-a) and 30 parts of dimethylformamide and stir at 23°C for 30 minutes. After cooling the resulting mixture to 0°C, 0.30 parts of sodium hydride were mixed and stirred at 0°C for 4 hours. To the resulting mixture, 3.17 parts of the salt represented by formula (I-8-b) were added at 0°C and stirred at 0°C for 3 hours to obtain a mixture containing the salt represented by formula (I-8-c). After raising the temperature of the resulting mixture to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then 6.41 parts of the salt represented by formula (I-8-d) were added and stirred at 23°C for 7 hours. To the resulting reaction product, 100 parts of chloroform and 30 parts of deionized water were added and stirred at 23°C for 30 minutes, then the organic layer was separated by liquid-liquid extraction. Thirty parts of deionized water were added to the recovered organic layer, and the mixture was stirred at 23°C for 30 minutes. The organic layer was then separated by liquid-liquid extraction. This washing procedure was repeated seven times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue, and the mixture was stirred at 23°C for 30 minutes. The supernatant was removed and the mixture was concentrated to obtain 2.59 parts of the salt represented by formula (I-46). MASS(ESI(+)Spectrum):M + 553.1 MASS(ESI(-)Spectrum):M - 517.1

[0245] Example 4: Synthesis of the salt represented by formula (I-122) TIFF2023156258000154.tif84148 3.15 parts of the salt represented by formula (I-122-a) and 30 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. Then 0.69 parts of potassium carbonate and 0.22 parts of potassium iodide were added and the temperature was raised to 75°C. 3.55 parts of the compound represented by formula (I-122-b) were added to the resulting mixture and stirred at 75°C for 5 hours, then cooled to 23°C. The resulting mixture was raised to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then 6.41 parts of the salt represented by formula (I-8-d) were added and stirred at 23°C for 7 hours. 100 parts of chloroform and 30 parts of deionized water were added to the resulting reaction product and stirred at 23°C for 30 minutes, then the organic layer was separated by liquid-liquid extraction. Thirty parts of deionized water were added to the recovered organic layer, and the mixture was stirred at 23°C for 30 minutes. The organic layer was then separated and removed. This washing procedure was repeated seven times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue, and the mixture was stirred at 23°C for 30 minutes. The supernatant was removed and the mixture was concentrated to obtain 6.48 parts of the salt represented by formula (I-122). MASS(ESI(+)Spectrum):M + 597.1 MASS(ESI(-)Spectrum):M - 517.1

[0246] Example 5: Synthesis of the salt represented by formula (I-116) JPEG2023156258000155.jpg87158 Mix 3.15 parts of the salt represented by formula (I-122-a) and 30 parts of dimethylformamide, stir at 23°C for 30 minutes, then add 0.69 parts of potassium carbonate and 0.22 parts of potassium iodide, and raise the temperature to 75°C. To the resulting mixture, add 3.55 parts of the compound represented by formula (I-122-b), stir at 75°C for 5 hours, and then cool to 23°C. After raising the temperature of the resulting mixture to 23°C, add 11 parts of 5% aqueous oxalic acid solution and stir at 23°C for 30 minutes, then add 4.42 parts of the salt represented by formula (I-2-d), and stir at 23°C for 7 hours. To the resulting reaction product, add 100 parts of chloroform and 30 parts of deionized water, stir at 23°C for 30 minutes, and then separate the organic layer. Thirty parts of deionized water were added to the recovered organic layer, and the mixture was stirred at 23°C for 30 minutes. The organic layer was then separated by liquid-liquid extraction. This washing procedure was repeated seven times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue, and the mixture was stirred at 23°C for 30 minutes. The supernatant was removed and the mixture was concentrated to obtain 5.89 parts of the salt represented by formula (I-116). MASS(ESI(+)Spectrum):M + 597.1 MASS(ESI(-)Spectrum):M - 339.1

[0247] Example 6: Synthesis of the salt represented by formula (I-274) TIFF2023156258000156.tif97162 4.18 parts of the compound represented by formula (I-274-a) and 30 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. After the resulting mixture was cooled to 0°C, 0.30 parts of sodium hydride were mixed and stirred at 0°C for 4 hours. 3.17 parts of the salt represented by formula (I-8-b) were added to the resulting mixture at 0°C and stirred at 0°C for 3 hours to obtain a mixture containing the salt represented by formula (I-274-c). After raising the temperature of the resulting mixture to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then 6.41 parts of the salt represented by formula (I-8-d) were added and stirred at 23°C for 7 hours. 100 parts of chloroform and 30 parts of deionized water were added to the resulting reaction product and stirred at 23°C for 30 minutes, after which the organic layer was separated. To the recovered organic layer, 30 parts of deionized water were added and stirred at 23°C for 30 minutes, after which the organic layer was separated. This washing procedure was repeated 7 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue and stirred at 23°C for 30 minutes, after which the supernatant was removed and concentrated to obtain 4.88 parts of the salt represented by formula (I-274). MASS(ESI(+)Spectrum):M + 679.0 MASS(ESI(-)Spectrum):M - 517.1

[0248] Example 7: Synthesis of the salt represented by formula (I-282) TIFF2023156258000157.tif97165 Mix 4.18 parts of the compound represented by formula (I-274-a) and 30 parts of dimethylformamide and stir at 23°C for 30 minutes. After cooling the resulting mixture to 0°C, 0.30 parts of sodium hydride were mixed and stirred at 0°C for 4 hours. To the resulting mixture, 3.17 parts of the salt represented by formula (I-8-b) were added at 0°C and stirred at 0°C for 3 hours to obtain a mixture containing the salt represented by formula (I-274-c). After raising the temperature of the resulting mixture to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then 5.70 parts of the salt represented by formula (I-16-d) were added and stirred at 23°C for 7 hours. To the resulting reaction product, 100 parts of chloroform and 30 parts of deionized water were added and stirred at 23°C for 30 minutes, then the organic layer was separated by liquid-liquid extraction. Thirty parts of deionized water were added to the recovered organic layer, and the mixture was stirred at 23°C for 30 minutes. The organic layer was then separated and removed. This washing procedure was repeated seven times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue, and the mixture was stirred at 23°C for 30 minutes. The supernatant was removed and the mixture was concentrated to obtain 4.39 parts of the salt represented by formula (I-282). MASS(ESI(+)Spectrum):M + 679.0 MASS(ESI(-)Spectrum):M - 467.1

[0249] Example 8: Synthesis of the salt represented by formula (I-502) TIFF2023156258000158.tif97165 Three 0.08 parts of the compound represented by formula (I-502-a) and thirty parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. After the resulting mixture was cooled to 0°C, 0.30 parts of sodium hydride were mixed and stirred at 0°C for 4 hours. Three 0.17 parts of the salt represented by formula (I-8-b) were added to the resulting mixture at 0°C and stirred at 0°C for 3 hours to obtain a mixture containing the salt represented by formula (I-502-c). After raising the temperature of the resulting mixture to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then six 0.41 parts of the salt represented by formula (I-8-d) were added and stirred at 23°C for 7 hours. To the resulting reaction product, 100 parts of chloroform and 30 parts of deionized water were added and stirred at 23°C for 30 minutes, then the organic layer was separated by liquid-liquid extraction. To the recovered organic layer, 30 parts of deionized water were added and stirred at 23°C for 30 minutes, after which the organic layer was separated and removed. This washing procedure was repeated 7 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue and stirred at 23°C for 30 minutes, after which the supernatant was removed and concentrated to obtain 3.49 parts of the salt represented by formula (I-502). MASS(ESI(+)Spectrum):M + 569.1 MASS(ESI(-)Spectrum):M - 517.1

[0250] Example 9: Synthesis of the salt represented by formula (I-510) TIFF2023156258000159.tif97168 3.08 parts of the compound represented by formula (I-502-a) and 30 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. After the resulting mixture was cooled to 0°C, 0.30 parts of sodium hydride were mixed and stirred at 0°C for 4 hours. 3.17 parts of the salt represented by formula (I-8-b) were added to the resulting mixture at 0°C and stirred at 0°C for 3 hours to obtain a mixture containing the salt represented by formula (I-502-c). After raising the temperature of the resulting mixture to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then 5.70 parts of the salt represented by formula (I-16-d) were added and stirred at 23°C for 7 hours. 100 parts of chloroform and 30 parts of deionized water were added to the resulting reaction product and stirred at 23°C for 30 minutes, after which the organic layer was separated. Thirty parts of deionized water were added to the recovered organic layer, and the mixture was stirred at 23°C for 30 minutes. The organic layer was then separated and removed. This washing procedure was repeated seven times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentration residue, and the mixture was stirred at 23°C for 30 minutes. The supernatant was removed and the mixture was concentrated to obtain 3.12 parts of the salt represented by formula (I-510). MASS(ESI(+)Spectrum):M + 569.1 MASS(ESI(-)Spectrum):M - 467.1

[0251] Example 10: Synthesis of the salt represented by formula (I-3884) TIFF2023156258000160.tif97163 Three 0.08 parts of the compound represented by formula (I-502-a) and 30 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. After the resulting mixture was cooled to 0°C, 0.30 parts of sodium hydride were mixed and stirred at 0°C for 4 hours. To the resulting mixture, three 0.17 parts of the salt represented by formula (I-8-b) were added at 0°C and stirred at 0°C for 3 hours to obtain a mixture containing the salt represented by formula (I-502-c). After raising the temperature of the resulting mixture to 23°C, 11 parts of 5% aqueous oxalic acid were added and stirred at 23°C for 30 minutes, then six 0.44 parts of the salt represented by formula (I-3884-d) were added and stirred at 23°C for 7 hours. To the resulting reaction product, 100 parts of chloroform and 30 parts of deionized water were added and stirred at 23°C for 30 minutes, then the organic layer was separated by liquid-liquid extraction. Thirty parts of deionized water were added to the recovered organic layer, and the mixture was stirred at 23°C for 30 minutes. The organic layer was then separated and removed. This washing procedure was repeated seven times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether were added to the concentrated residue, and the mixture was stirred at 23°C for 30 minutes. The supernatant was removed and the mixture was concentrated to obtain 3.61 parts of the salt represented by formula (I-3884). MASS(ESI(+)Spectrum):M + 569.1 MASS(ESI(-)Spectrum):M - 541.2

[0252] Resin synthesis The compounds (monomers) used in the synthesis of resin (A) are shown below. Hereafter, these compounds will be referred to as "monomers (a1-1-3)," etc., according to their formula numbers. TIFF2023156258000161.tif49161

[0253] Synthesis Example 1 [Synthesis of Resin A1] Monomers (a1-2-6), (a2-1-3), (a3-4-2), and (a1-4-2) were used as monomers, and they were mixed in a molar ratio [monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):monomer (a1-4-2)] of 53:3:12:32. Further, methyl isobutyl ketone was added to this monomer mixture in an amount equal to 1.5 times the total mass of all monomers. To the resulting mixture, azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at concentrations of 1.2 mol% and 3.6 mol%, respectively, relative to the total amount of monomers, and the mixture was heated at 73°C for approximately 5 hours. Subsequently, an aqueous solution of p-toluenesulfonic acid (2.5 wt%) equal to 2.0 times the total mass of all monomers was added to the polymerization reaction solution, and after stirring for 12 hours, the solution was separated. The recovered organic layer is poured into a large amount of n-heptane to precipitate resin, which is then filtered and recovered, resulting in a weight-average molecular weight of approximately 5.3 × 10⁶. 3 Resin A1 was obtained with a yield of 88%. This resin A1 has the following structural units. TIFF2023156258000162.tif38135

[0254] Synthesis Example 2 [Synthesis of Resin A2] Monomers (a1-2-6), (a2-1-3), (a3-4-2), and (a1-4-13) were used as monomers, and they were mixed in a molar ratio [monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):monomer (a1-4-13)] of 53:3:12:32. Further, methyl isobutyl ketone was added to this monomer mixture in an amount equal to 1.5 times the total mass of all monomers. To the resulting mixture, azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at concentrations of 1.2 mol% and 3.6 mol%, respectively, relative to the total amount of monomers, and the mixture was heated at 73°C for approximately 5 hours. Subsequently, an aqueous solution of p-toluenesulfonic acid (2.5 wt%) equal to 2.0 times the total mass of all monomers was added to the polymerization reaction solution, and after stirring for 12 hours, the solution was separated. The recovered organic layer is poured into a large amount of n-heptane to precipitate resin, which is then filtered and recovered, resulting in a weight-average molecular weight of approximately 5.1 × 10⁶. 3 Resin A2 was obtained with a yield of 79%. This resin A2 has the following structural units. TIFF2023156258000163.tif38135

[0255] Synthesis Example 3 [Synthesis of Resin A3] Monomers (a1-2-6), (a2-1-3), (a3-4-2), and (a1-4-19) were used as monomers, and they were mixed in a molar ratio [monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):monomer (a1-4-19)] of 53:3:12:32. Further, methyl isobutyl ketone was added to this monomer mixture in an amount equal to 1.5 times the total mass of all monomers. To the resulting mixture, azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at concentrations of 1.2 mol% and 3.6 mol%, respectively, relative to the total amount of monomers, and the mixture was heated at 73°C for approximately 5 hours. Subsequently, an aqueous solution of p-toluenesulfonic acid (2.5 wt%) equal to 2.0 times the total mass of all monomers was added to the polymerization reaction solution, and after stirring for 12 hours, the solution was separated. The recovered organic layer is poured into a large amount of n-heptane to precipitate resin, which is then filtered and recovered, resulting in a weight-average molecular weight of approximately 5.5 × 10⁶. 3 Resin A3 was obtained with a yield of 74%. This resin A3 has the following structural units. TIFF2023156258000164.tif38127

[0256] <Preparation of the resist composition> As shown in Table 2, the following components were mixed, and the resulting mixture was filtered through a fluororesin filter with a pore size of 0.2 μm to prepare a resist composition. [Table 2]

[0257] <Resin> A1~A3: Resin A1~Resin A3 <Salt (I)> I-2: Salt represented by formula (I-2) I-8: Salt represented by formula (I-8) I-46: Salt represented by formula (I-46) I-116: Salt represented by formula (I-116) I-122: Salt represented by formula (I-122) I-274: Salt represented by formula (I-274) I-282: Salt represented by formula (I-282) I-502: Salt represented by formula (I-502) I-510: Salt represented by formula (I-510) I-3884: Salt represented by formula (I-3884) <Acid Generator> IX-1: Synthesized by the method described in Japanese Patent Publication No. 2010-140014 IX-2: Synthesized by the method described in Japanese Patent Publication No. 2011-006399 TIFF2023156258000166.tif31153<Quencher(C)> C1: Synthesized by the method described in Japanese Patent Publication No. 2011-39502 TIFF2023156258000167.tif3646<solvent> Propylene glycol monomethyl ether acetate, 400 units Propylene glycol monomethyl ether, 100 parts γ-Butyrolactone 5 parts

[0258] (Electron beam exposure evaluation of resist compositions: Organic solvent development) A 6-inch silicon wafer was treated on a direct hot plate with hexamethyldisilazane at 90...

Claims

1. An acid generator containing a salt represented by formula (I): [In formula (I), R １ , R ２ and R ３ each independently represents a hydrogen atom, a halogen atom, or a haloalkyl group having 1 to 12 carbon atoms. １ , R ２ and R ３ At least one of the groups is a halogen atom or a haloalkyl group having 1 to 12 carbon atoms. ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. R ４ , R ５ , R ６ , R ７ , R ８ and R ９ each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 36 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. A １ , A ２ and A ３ each independently represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. W １ , W ２ and W ３ each independently represents an alicyclic hydrocarbon group having 3 to 28 carbon atoms, and —CH 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. m1 represents an integer of 1 to 5, and when m1 is 2 or more, the groups in the parentheses may be the same or different. m2 represents an integer of 0 to 5, and when m2 is 2 or more, the groups in the parentheses may be the same or different. m3 represents an integer of 0 to 5, and when m3 is 2 or more, the groups in the parentheses may be the same or different. m4 represents an integer of 0 to 13, and when m4 is 2 or more, a plurality of R ４ may be the same or different from each other. m5 represents an integer of 0 to 13, and when m5 is 2 or more, a plurality of R ５ may be the same or different from each other. m6 represents an integer of 0 to 13, and when m6 is 2 or more, a plurality of R ６ may be the same or different from each other. m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R ７ may be the same or different from each other. m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R ８ may be the same or different from each other. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 1≦m1+m7≦5, 0≦m2+m8≦5, and 0≦m3+m9≦5. AI － represents an organic anion.

2. A １ But, ***-X ０１ -L ０１ - or ***-L ０１ -X ０１ - and A ２ But, ***-X ０２ -L ０２ - or ***-L ０２ -X ０２ - and A ３ But, ***-X ０３ -L ０３ - or ***-L ０３ -X ０３ - and X ０１ , X ０２ and X ０３ each independently represents —O—, —CO—, —S—, or —SO ２ represents -, L ０１ , L ０２ and L ０３ each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and —CH ２ - represents -O-, -CO-, -S- or -SO ２ - may be replaced by . *** is A １ , A ２ or A ３ represents a bonding site to the benzene ring to which the acid generator according to claim 1 can be bonded.

3. X ０１ , X ０２ and X ０３ The acid generator according to claim 2, wherein each of the groups independently represents —O— or —S—.

4. L ０１ , L ０２ and L ０３ each independently represents a single bond or an alkanediyl group having 1 to 6 carbon atoms (the —CH ２ 3. The acid generator according to claim 2, wherein - may be replaced by -O- or -CO-.

5. AI － 2. The acid generator according to claim 1, wherein is a sulfonate anion, a sulfonylimide anion, or a sulfonylmethide anion.

6. AI － is a sulfonate anion, and the sulfonate anion is an anion represented by formula (IA) or an anion represented by formula (IB). [In formula (IA), Q １ and Q ２ each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L １ represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ The - may be replaced by -O- or -CO-, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y １ represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and —CH ２ - is -O-, -S-, -SO ２ - or -CO- may be substituted.] [In formula (IB), m21 represents an integer of 1 to 5, and when m21 is 2 or greater, the groups in the parentheses may be the same or different. R 21 represents a hydrocarbon group having 3 to 48 carbon atoms, including a cyclic hydrocarbon group having 3 to 18 carbon atoms, and the cyclic hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -S-, -SO ２ It may be replaced by - or -CO-. R 2２ represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and —CH ２ - may be replaced by -O- or -CO-. m22 represents an integer of 0 to 4, and when m22 is 2 or more, a plurality of R 2２ may be the same or different.]

7. A resist composition comprising the acid generator according to any one of claims 1 to 6.

8. further containing a resin containing a structural unit having an acid labile group, 8. The resist composition according to claim 7, wherein the structural unit having an acid labile group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), and a structural unit represented by formula (a1-2): [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L ａ１ and L ａ２ are each independently —O— or *—O—(CH ２ ) ｋ１ represents —CO—O—, k1 represents an integer of 1 to 7, and * represents the bonding site with —CO—. R a01 , R ａ４ and R ａ５ each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. R ａ６ and R ａ７ each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these. m1' represents an integer of 0 to 14; n1 represents an integer of 0 to 10. n1′ represents an integer of 0 to 3.]

9. further containing a resin containing a structural unit having an acid labile group, 8. The resist composition according to claim 7, wherein the resin containing a structural unit having an acid labile group contains a structural unit represented by formula (a2-A): [In formula (a2-A), R a50 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a50 is a single bond or *-X a51 - (A a52 -X a52 ) nｂ -, * represents -R a50 represents the bonding site with the carbon atom to which it is bonded. A a52 represents an alkanediyl group having 1 to 8 carbon atoms. X a51 and X a52 each independently represents —O—, —CO—O—, or —O—CO—. nb represents 0 or 1. mb represents an integer of 0 to 4. When mb is an integer of 2 or more, a plurality of R a51 may be the same or different.]

10. 8. The resist composition according to claim 7, further comprising a salt that generates an acid weaker in acidity than the acid generated from the salt represented by formula (I).

11. (1) a step of applying the resist composition according to claim 7 onto a substrate; (2) a step of drying the applied composition to form a composition layer; (3) exposing the composition layer to light; (4) a step of heating the composition layer after exposure; and (5) developing the composition layer after heating; A method for producing a resist pattern comprising:

12. A salt represented by formula (I): [In formula (I), R １ , R ２ and R ３ each independently represents a hydrogen atom, a halogen atom, or a haloalkyl group having 1 to 12 carbon atoms. １ , R ２ and R ３ At least one of the groups is a halogen atom or a haloalkyl group having 1 to 12 carbon atoms. ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. R ４ , R ５ , R ６ , R ７ , R ８ and R ９ each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 36 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. A １ , A ２ and A ３ each independently represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. W １ , W ２ and W ３ each independently represents an alicyclic hydrocarbon group having 3 to 28 carbon atoms, and —CH 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. m1 represents an integer of 1 to 5, and when m1 is 2 or more, the groups in the parentheses may be the same or different. m2 represents an integer of 0 to 5, and when m2 is 2 or more, the groups in the parentheses may be the same or different. m3 represents an integer of 0 to 5, and when m3 is 2 or more, the groups in the parentheses may be the same or different. m4 represents an integer of 0 to 13, and when m4 is 2 or more, a plurality of R ４ may be the same or different from each other 。 m5 represents an integer of 0 to 13, and when m5 is 2 or more, a plurality of R ５ may be the same or different from each other. stomach. m6 represents an integer of 0 to 13, and when m6 is 2 or more, a plurality of R ６ may be the same or different good. m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R ７ are the same but different Good too. m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R ８ may be the same or different from each other. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 1≦m1+m7≦5, 0≦m2+m8≦5, and 0≦m3+m9≦5. AI － is an organic anion represent.]

13. A １ But, ***-X ０１ -L ０１ - or ***-L ０１ -X ０１ - and A ２ But, ***-X ０２ -L ０２ - or ***-L ０２ -X ０２ - and A ３ But, ***-X ０３ -L ０３ - or ***-L ０３ -X ０３ - and X ０１ , X ０２ and X ０３ each independently represents —O—, —CO—, —S—, or —SO ２ represents -, L ０１ , L ０２ and L ０３ each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and —CH ２ - represents -O-, -CO-, -S- or -SO ２ - may be replaced by . *** is A １ , A ２ or A ３ The salt according to claim 12, wherein the benzene ring is bonded to a bond site where the benzene ring can be bonded.

14. X ０１ , X ０２ and X ０３ The salt according to claim 13, wherein each of the groups independently represents -O- or -S-.

15. L ０１ , L ０２ and L ０３ each independently represents a single bond or an alkanediyl group having 1 to 6 carbon atoms (the —CH ２ The salt according to claim 13 or 14, wherein - may be replaced by -O- or -CO-.

16. AI － The salt according to claim 12 or 13, wherein is a sulfonate anion, a sulfonylimide anion, or a sulfonylmethide anion.

17. AI － is a sulfonate anion, and the sulfonate anion is an anion represented by formula (IA) or an anion represented by formula (IB). [In formula (IA), Q １ and Q ２ each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L １ represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ The - may be replaced by -O- or -CO-, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y １ represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and —CH ２ - is -O-, -S-, -SO ２ - or -CO- may be substituted.] [In formula (IB), m21 represents an integer of 1 to 5, and when m21 is 2 or greater, the groups in the parentheses may be the same or different. R 21 represents a hydrocarbon group having 3 to 48 carbon atoms, including a cyclic hydrocarbon group having 3 to 18 carbon atoms, and the cyclic hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -S-, -SO ２ It may be replaced by - or -CO-. R ２２ represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and —CH ２ - may be replaced by -O- or -CO-. m22 represents an integer of 0 to 4, and when m22 is 2 or more, a plurality of R ２２ may be the same or different.]

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