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

Abstract

To provide a salt and the like which allow a resist pattern having good CD uniformity to be produced.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 a salt, an acid generator, a resist composition, and a method for producing a resist pattern. [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. TIFF2023156259000001.tif3867 [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2012-247502 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a salt that forms a resist pattern with better CD uniformity (CDU) than a resist pattern formed from a resist composition containing the above salt. [Means for solving the problem]

[0005] The present invention includes the following inventions. [1] An acid generator containing a salt represented by formula (I). TIFF2023156259000002.tif60150[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, provided that R 1 , R 2 and R 3At least one of them is a halogen atom or a haloalkyl group having a carbon number of 1 to 12. -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 optionally having a substituent, and -CH2- contained in the haloalkyl group and the hydrocarbon group optionally being 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, and the hydrocarbon group may have a substituent, and -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, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. m1 represents an integer of 0 to 5, and when m1 is 2 or greater, the groups in the parentheses may be the same or different. m2 represents an integer of 0 to 4, and when m2 is 2 or greater, the groups in the parentheses may be the same or different. m3 represents an integer of 0 to 4, and when m3 is 2 or greater, 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 5, 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 4, 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 4, and when m9 is 2 or more, a plurality of R 9 may be the same or different from each other. However, 0≦m1+m7≦5, 0≦m2+m8≦4, and 0≦m3+m9≦4, and at least one of m1, m2, and m3 represents an integer of 1 or more. X 7 represents a single bond, -CH2-, -O-, -S-, -CO-, -SO- or -SO2-. 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 -SO2-; L 01 , L 02 and L 03each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and -CH- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S-, or -SO-), *** is A 1 , A 2 or A 3 represents a bonding site to the benzene ring to which it can be bonded [1]. [3]X 01 , X 02 and X 03 are each independently -O- or -S-. [4]L 01 , L 02 and L 03 are each independently a single bond or an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-). [5] AI - 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). TIFF2023156259000003.tif2965[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, wherein -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-, and wherein a hydrogen atom contained in the saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y 1represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-.] TIFF2023156259000004.tif3081[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, the cyclic hydrocarbon group optionally having a substituent, and -CH2- contained in the hydrocarbon group optionally being replaced by -O-, -S-, -SO2- or -CO-. R 22 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and one --CH.sub.2-- contained in the alkyl group may be replaced with --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 from each other.] [7] A resist composition containing the acid generator according to any one of [1] to [6]. [8] The resist composition according to [7], further comprising a resin containing a structural unit having an acid labile group, 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): TIFF2023156259000005.tif44143 [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or -O-(CH2) 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 a5each 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] The resist composition according to [7] or [8], further comprising a resin containing a structural unit having an acid labile group, wherein the resin containing a structural unit having an acid labile group comprises a structural unit represented by formula (a2-A): TIFF2023156259000006.tif4653[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 a52represents 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 from each other.

[10] The resist composition according to any one of [7] to [9], further comprising a salt that generates an acid that is 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 any one of [7] to

[10] onto a substrate; (2) drying the applied composition to form a composition layer; (3) exposing the composition layer to light; (4) heating the composition layer after exposure; and (5) A method for producing a resist pattern, comprising the step of developing the composition layer after heating.

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

[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 -SO2-; L 01 , L 02 and L 03each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and -CH- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S-, or -SO-), *** is A 1 , A 2 or A 3 represents a bonding site to the benzene ring to which it can be bonded.

[14] X 01 , X 02 and X 03 are each independently -O- or -S-.

[15] L 01 , L 02 and L 03 are each independently a single bond or an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-).

[16] AI - 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 the above formula (IA) or an anion represented by the formula (IB). [Effects of the Invention]

[0006] By using a resist composition containing the salt of the present invention, a resist pattern with good CD uniformity (CDU) can be produced. DETAILED DESCRIPTION OF THE INVENTION

[0007] In this specification, "(meth)acrylic monomer" means "at least one of an acrylic monomer and a methacrylic monomer." The terms "(meth)acrylate" and "(meth)acrylic acid" have the same meaning. Regarding groups described in this specification, those that can have either a linear or branched structure are acceptable. When -CH2- in a hydrocarbon group or the like is replaced with -O-, -S-, -CO-, or -SO2-, the same examples apply to each group. A "combined group" refers to a group in which two or more of the exemplified groups are bonded, and the valence of these groups may vary depending on the bonding form. "Derived from" or "derived from" refers to a polymerizable C=C bond in the molecule becoming a -CC- group (single bond) through polymerization. When stereoisomers exist, all stereoisomers are included.

[0008] [Salt represented by formula (I)] The present invention relates to a salt represented by formula (I) (hereinafter sometimes referred to as "salt (I)"). In the salt (I), the side with a positive charge is sometimes called the "cation (I)" and the side with a negative charge is sometimes called the "anion (I)." [Cation (I)] The cation (I) of the salt represented by formula (I) is a cation represented by the following formula (IC): TIFF2023156259000007.tif60155 [In formula (IC), all symbols have the same meanings 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 the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 1 , R 2 , R 3 , R 4 , R 5 , R6 , R 7 , R 8 and R 9 The haloalkyl group having 1 to 12 carbon atoms refers to an alkyl group having 1 to 12 carbon atoms and containing a halogen atom, and examples thereof include a fluorinated alkyl group having 1 to 12 carbon atoms, a chlorinated alkyl group having 1 to 12 carbon atoms, a brominated alkyl group having 1 to 12 carbon atoms, and an iodinated alkyl group having 1 to 12 carbon atoms. Examples of the haloalkyl group include a perfluoroalkyl group having 1 to 12 carbon atoms (e.g., a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a nonafluorobutyl group), a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, a 3,3,4,4,4-pentafluorobutyl group, a chloromethyl group, a bromomethyl group, and an iodomethyl group. The number of carbon atoms in the haloalkyl group is preferably 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Examples of the hydrocarbon group having 1 to 36 carbon atoms include chain 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. The alkyl group is a linear or branched alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The alkanediyl group is a linear or branched alkanediyl group, such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, or a hexane-1,6-diyl group; and Examples of branched alkanediyl groups include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 9, still more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups shown below: The bonding site may be at any position. TIFF2023156259000008.tif46169Specifically, examples of monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl.Examples of 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 the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms. Examples of groups formed by combining two or more of chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups include a group 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-*, where -CH2- contained in the alkanediyl group and the alkyl group may be replaced by -O-, -CO-, -S-, or -SO2-), a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group-alkanediyl group- Examples of such groups include an alkanediyl group-*, an alkyl group-alicyclic hydrocarbon group-*, an alkyl group-alicyclic hydrocarbon group-alkanediyl group-*, where —CH— contained in the alicyclic hydrocarbon group, the alkanediyl group, and the alkyl group may be replaced by —O—, —CO—, —S—, or —SO—, and groups combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, an aromatic hydrocarbon group-alicyclic hydrocarbon group-*, an alicyclic hydrocarbon group-aromatic hydrocarbon group-*, where —CH— contained in the alicyclic hydrocarbon group may be replaced by —O—, —CO—, —S—, or —SO—). * represents a bonding site. The aromatic hydrocarbon group -alkanediyl group-* includes aralkyl groups such as benzyl group and phenethyl group. Examples of the alkyl group-aromatic hydrocarbon group-* include a tolyl group, a xylyl group, and a cumenyl group. Examples of the alicyclic hydrocarbon group -alkanediyl group-* include cycloalkylalkyl groups such as a cyclohexylmethyl group, a cyclohexylethyl group, a 1-(adamantan-1-yl)methyl group, and a 1-(adamantan-1-yl)-1-methylethyl group. Examples of the alkyl group-alicyclic hydrocarbon group-* include cycloalkyl groups having an alkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, and a 2-alkyladamantan-2-yl group. Examples of the aromatic hydrocarbon group-alicyclic hydrocarbon group-* include a phenylcyclohexyl group. Examples of the alicyclic hydrocarbon group-aromatic hydrocarbon group-* include a 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. 1 , W 2 Or W 3 or a benzene ring. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and haloalkyl groups represented by R 4 , R 5 , R 6 , R 7 , R 8 and R 9 When -CH2- in the hydrocarbon group represented by the formula (I) is replaced with -O-, -CO-, -S-, or -SO2-, the number of carbon atoms before the replacement is the total number of carbon atoms in the haloalkyl group or the hydrocarbon group. In addition, the number may be 1 or 2 or more. Examples of haloalkyl groups and groups in which -CH2- in a hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), and a hydroxyl group (a group in which -CH2- at any position in an alkyl group is replaced by -O-). a group in which -CH2-CH2- is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced by -CO-O-), an alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced by -S-), an alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced by -SO2-), an oxy group (a group in which -CH in a methylene group 2- is replaced by -O-), carbonyl group (a group in which -CH2- in a methylene group is replaced by -CO-), thio group (a group in which -CH2- in a methylene group is replaced by -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced by -SO2-), alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced by -O-), alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced by -O-CO-), a an alkanediylcarbonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced with -CO-O-), an alkanediylthio group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -S-), an alkanediylsulfonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -SO2-), a cycloalkoxy group, a cycloalkylalkoxy group,Examples of such groups include an alkoxycarbonyloxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, a haloalkoxy group (a group in which -CH- at any position in a haloalkyl group is replaced with -O-), a haloalkoxycarbonyl group (a group in which -CH-CH- at any position in a haloalkyl group is replaced with -O-CO-), a haloalkylcarbonyl group (a group in which -CH- at any position in a haloalkyl group is replaced with -CO-), a haloalkylcarbonyloxy group (a group in which -CH-CH- at any position in a haloalkyl group is replaced with -CO-O-), and a group in which two or more of these groups are combined. Examples of the alkoxy group include alkoxy groups having 1 to 35 carbon atoms, such as a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group, etc. 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. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 35 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 36 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 35 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. 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 alkylcarbonyloxy group preferably has 2 to 11 carbon atoms, more preferably 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and even more preferably 2 or 3 carbon atoms. Examples of the alkylthio group include alkylthio groups having 1 to 35 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a 2-ethylhexylthio group, a nonylthio group, a decylthio group, an undecylthio group, etc. 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 still more preferably 1 to 3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 35 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a 2-ethylhexylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, etc. 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 still more preferably 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 35 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. 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 still more preferably 1 to 3. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 35 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 36 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 35 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. 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 still 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 still 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 still more preferably 2 or 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 35 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. 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 still more preferably 1 to 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 35 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. 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 still more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 35 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 36 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 34 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 35 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 36 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 35 carbon atoms, such as a phenyloxy group. Examples of the haloalkoxy group, haloalkoxycarbonyl group, haloalkylcarbonyl group, and haloalkylcarbonyloxy group 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, and include groups in which one or more hydrogen atoms of the above-exemplified groups have been replaced with a halogen atom. Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO-, or -SO2- include the groups shown below. Also included are groups in which, among the groups shown below, -O- is replaced with -S- and -CO- is replaced with -SO2-. The bonding site can be at any position. TIFF2023156259000009.tif47168

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

[0011] A 1 , A 2 and A 3 Examples of the hydrocarbon group include linear or branched chain hydrocarbon groups (e.g., alkanediyl groups, etc.), monocyclic or polycyclic alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be a combination of two or more of these groups. 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, still more preferably 1 to 14, and even more preferably 1 to 12. Examples of the chain hydrocarbon group include straight-chain alkanediyl 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 an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 9, still more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups shown below: The bonding site may be at any position. TIFF2023156259000010.tif46169Specifically, monocyclic alicyclic hydrocarbon groups such as 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; Examples of the polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkanediyl 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 alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms, even more preferably 3 to 12 carbon atoms, and even more preferably 3 to 10 carbon atoms. Examples of the aromatic hydrocarbon group include arylene groups such as a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, etc. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0012] Examples of groups formed by combining two or more groups include a group combining an alicyclic hydrocarbon group with an alkanediyl group, a group combining an aromatic hydrocarbon group with an alkanediyl group, and a group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group. Regarding the combination, two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups may each 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 In the case where a -CH2- in the hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2-, the number of carbon atoms before the replacement is taken as the total number of carbon atoms in the hydrocarbon group. The number may be 1 or 2 or more, but is preferably 1 to 3. Examples of groups in which -CH2- in a hydrocarbon group is replaced by -O-, -CO-, -S-, or -SO2- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced by , -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), oxy group (a group in which -CH2- in a methylene group is replaced with -O- a carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), a thio group (a group in which -CH2- in a methylene group is replaced with -S-), a sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), an alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -O-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which an alkanediyl group in which -CH2- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -CO-O-), an alkanediylsulfonyl group (a group in which -CH2- at any position in an alkanediyl group is replaced with -SO2-), an alkanediylthio group (a group in which -CH2- at any position in an alkanediyl group is replaced with -S-), a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group,Examples include an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group formed by combining two or more of these groups. Examples of the alkoxy group include alkoxy groups having 1 to 19 carbon atoms, such as a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group, etc. 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. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 19 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 20 carbon atoms, such as acetyl, propionyl, and butyryl. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 19 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy. 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 alkylcarbonyloxy group preferably has 2 to 11 carbon atoms, more preferably 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and even more preferably 2 or 3 carbon atoms. The alkylthio group includes alkylthio groups having 1 to 19 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, etc. 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 still more preferably 1 to 3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 19 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, etc. 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 still more preferably 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 19 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. 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 still more preferably 1 to 3. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 19 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 20 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 19 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. 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 still 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 still 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 still more preferably 2 or 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 19 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. 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 still more preferably 1 to 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 19 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. 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 still more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 19 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 19 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 18 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 19 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 19 carbon atoms, such as a phenyloxy group.

[0014] Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2- include the groups shown below. Also included are groups in which, among the groups shown below, -O- is replaced with -S- and -CO- is replaced with -SO2-. The bonding site can be at any position. TIFF2023156259000011.tif47170A 1 , A 2 and A 3 The substituents that the hydrocarbon group may have include R 4 ~R 9 Examples of the substituents that the hydrocarbon group may have include the same groups as those exemplified above.

[0015] A 1 , A 2 and A 3are each independently a hydrocarbon group having 1 to 20 carbon atoms (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-, provided that at least one of -CH2- contained in the hydrocarbon group is replaced by -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 each independently represents -O-, -CO-, -S- or -SO2-. 011 , L 012 , L 021 , L 022 , L 031 and L 032 are each independently a single bond or a hydrocarbon group having 1 to 19 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. 011 and L 012 The total number of carbon atoms is 0 to 19, and L 021 and L 022 The total number of carbon atoms is 0 to 19, and L 031 and L 032 The total number of carbon atoms is 0 to 19. 1 , A 2 or A 3 represents a bonding site to the benzene ring to which A can be bonded. 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 each independently represents -O-, -CO-, -S- or -SO2-. 01 , L 02 and L 03 are each independently a single bond or a hydrocarbon group having 1 to 19 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. *** is A 1 , A 2 or A 3 represents a bonding site to the benzene ring to which A can be bonded. 1 , A 2 and A 3 is preferably one that 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 The hydrocarbon group having 1 to 19 carbon atoms (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-) may be any of the hydrocarbon groups having 1 to 19 carbon atoms, 1 , A 2 and A 3 Examples of the groups include the same groups as those listed in the above. X 01 , X 02 and X 03 are each independently preferably -O- or -S-, more preferably -O-. L 011 , L 012, L 021 , L 022 , L 031 , L 032 , L 01 , L 02 and L 03 are each independently preferably a single bond or a hydrocarbon group having 1 to 18 carbon atoms (-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 (-CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-), and are each independently preferably a single bond or a chain hydrocarbon group having 1 to 9 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-). is more preferable, a single bond or an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), even more preferable, a single bond or an alkanediyl group having 1 to 4 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), and even more preferable, a single bond or an alkanediyl group having 1 to 3 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-). Among these, a single bond, a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-2,2-diyl group, a carbonyl group, a carbonyloxy group, a carbonyloxymethylene group, an ethyleneoxy group, an ethyleneoxymethylene group, a methylenecarbonyloxy group, a methylenecarbonyloxymethylene group, or an ethyleneoxycarbonyl group is preferred. A 1 The bonding positions of each of the groups to the benzene ring are independently + The bonding position may be either o-position, m-position or p-position. + It is preferable that m1 is bonded to the p-position or m-position relative to the bonding position of A. Specifically, when m1 is 1, A 1 are each independently, S +It is preferably bonded to the p-position or m-position, more preferably to the p-position, relative to the bonding position of A. 1 are each independently, S + With respect to the bonding positions of A, it is preferable that one is bonded to the o-position or the m-position, and one is bonded to the o-position or the m-position, and it is more preferable that two are bonded to the m-position. 1 are each independently, S + With respect to the bonding positions of A, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position. 1 are each independently, S + With respect to the bonding positions of the above, it is preferred that two are bonded to the o-position or m-position and two are bonded to the p-position or m-position, and it is more preferred that two are bonded to the o-position and two are bonded to the m-position. A 2 and A 3 The bonding positions of the fused rings to the benzene ring are each independently S + The bonding position may be either o-position, m-position or p-position. + Preferably, m2 and m3 are bonded independently to the p-position or m-position, more preferably to the p-position. More specifically, when m2 and m3 are 1, A 2 and A 3 are each independently, S + Preferably, the bond is at the p-position or m-position relative to the bonding position of A, and more preferably at the p-position. 2 and A 3 are each independently, S + With respect to the bonding positions of A, it is preferred that one is bonded to the o-position or the m-position, and one is bonded to the o-position or the m-position, and it is more preferred that two are bonded to the m-position. 2 and A 3 are each independently, S +With respect to the bonding positions of the above, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position.

[0016] W 1 , W 2 and W 3 The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups shown below: The bonding site may be at any position. TIFF2023156259000012.tif46169Specifically, 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 a cycloalkyl group bonded to a norbornyl or adamantyl group via a spiro bond.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] Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2- include the groups shown below. Also included are groups in which, among the groups shown below, -O- is replaced with -S- and -CO- is replaced with -SO2-. The bonding site can be at any position. TIFF2023156259000013.tif46168

[0018] W 1 , W 2 and W 3The alicyclic hydrocarbon group (wherein -CH2- may be replaced with -O-, -CO-, -S-, or -SO2-) is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- 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 (w1-12) to (w1-24), and even more preferably a group represented by any of formulas (w1-1) to (w1-3), (w1-15), and (w1-22). TIFF2023156259000014.tif46168[Formula (w1-1) to formula (w1-24), The —CH2— contained in the group may be replaced by —O—, —S—, —CO— or —SO2—. The bonding site may be at any position.] Among them, W 1 , W 2 and W 3 is preferably a cyclohexyl group or an adamantyl group, and more preferably an adamantyl group.

[0019] m1 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 1. m2 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, even more preferably 0 or 1, and even more preferably 0. m3 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, even more preferably 0 or 1, and even more preferably 0. m4 is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, even more preferably an integer of 0 to 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1. m5 is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, even more preferably an integer of 0 to 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1. m6 is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, even more preferably an integer of 0 to 3, still more preferably 0, 1 or 2, and even more preferably 0 or 1. m7 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. 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 are each independently preferably a hydrogen atom, a halogen atom, or a haloalkyl group having 1 to 6 carbon atoms (wherein -CH2- contained in the haloalkyl group may be replaced with -O- or -CO-), more preferably a hydrogen atom, a halogen atom, or a fluorinated alkyl group having 1 to 4 carbon atoms, even more preferably a hydrogen atom, a fluorine atom, an iodine atom, a bromine atom, or a perfluoroalkyl group having 1 to 4 carbon atoms, still 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. 1 , R 2 and R 3 At least one of the groups is a halogen atom-containing group. R4 , R 5 and R 6 are each independently preferably a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), even more preferably a fluorine atom, iodine atom, bromine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), still more preferably a fluorine atom, iodine atom, bromine atom, methyl group, hydroxy group, or trifluoromethyl group, and even more preferably an iodine atom. R 7 , R 8 and R 9 are each independently preferably a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), still more preferably a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-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 The bonding position of to the benzene ring is S + It may be at the o-position, m-position, or p-position relative to the bonding position of R 7 is S +It is preferably bonded to the p-position or m-position, more preferably to the p-position, relative to the bonding position of R 7 are each independently, S + With respect to the bonding positions of R, it is preferred that one is bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that one is bonded to the m-position and one is bonded to the p- or m-position. 7 are each independently, S + With respect to the bonding positions of R, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position. 7 are each independently, S + With respect to the bonding positions of the above, it is preferred that two are bonded to the o-position or m-position and two are bonded to the p-position or m-position, and it is more preferred that two are bonded to the m-position, one is bonded to the o-position and one is bonded to the p-position. R 8 and R 9 The bonding positions of each of the groups to the benzene ring are independently + In particular, when m8 and m9 are 1, R 8 and R 9 are each independently, S + When m8 and m9 are 2, R 8 and R 9 are each independently, S + With respect to the bonding positions of R, it is preferred that one is bonded to the o-position or m-position and one is bonded to the p-position or m-position, and it is more preferred that one is bonded to the m-position and one is bonded to the p-position or m-position. 8 and R 9 are each independently, S + With respect to the bonding positions of the above, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position.

[0020] Examples of the cation represented by formula (IC) include the cation represented by formula (IC-1) (hereinafter sometimes referred to as "cation (IC-1)"). TIFF2023156259000015.tif62165[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 , L 02 , L 03 , X 01 , X 02 , X 03 and X 7 The symbols have the same meanings as above.] X 7 is preferably a single bond, —CH2—, or —O—. X 01 , X 02 and X 03 The bonding positions of A to the benzene ring are each independently 1 , A 2 and A 3 The bonding position to the benzene ring is the same as that of

[0021] Examples of the cation of the salt (I) include cations represented by the following formulae (Ic-1) to (Ic-95). TIFF2023156259000016.tif230163

[0022] TIFF2023156259000017.tif240166

[0023] TIFF2023156259000018.tif241164

[0024] TIFF2023156259000019.tif229166

[0025] TIFF2023156259000020.tif130149

[0026] [Anion (I)] The anion (I) of the salt represented by formula (I) is AI - It is an organic anion represented by the formula: AI - Examples of the organic anion represented by the formula AI include a sulfonate anion, a sulfonylimide anion, and a sulfonylmethide anion. - The organic anion represented by formula (IA) is preferably a sulfonate anion, and more preferably an anion represented by formula (IB). TIFF2023156259000021.tif2965[In formula (IA), Q 1 and Q 2 each 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, wherein -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-, and wherein a 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 -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-.]

[0027] In formula (IA), when -CH2- in the saturated hydrocarbon group is replaced with -O- or -CO-, the number of carbon atoms before the replacement is defined as the number of carbon atoms in the saturated hydrocarbon group. Also, when -CH2- in the cyclic hydrocarbon group is replaced with -O-, -S-, -SO2- or -CO-, the number of carbon atoms before the replacement is defined as the number of carbon atoms in the cyclic hydrocarbon group.

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

[0029] L 1 Examples of the divalent saturated hydrocarbon group in include a linear alkanediyl group, a branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and may also be a group formed by combining two or more of these groups. Specific examples include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, a decane-1,10-diyl group, an undecane-1,11-diyl group, a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, and a heptadecane-1,17-diyl group; branched alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl; monocyclic divalent alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, such as 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 1 Examples of the group in which -CH2- in the divalent saturated hydrocarbon group represented by the formula (b1-1) is replaced with -O- or -CO- include groups represented by any of formulas (b1-1) to (b1-3). In the groups represented by formulas (b1-1) to (b1-3) and specific examples thereof, groups represented by formulas (b1-4) to (b1-11), * and ** represent bonding sites, * indicates -Y 1 represents the binding site with

[0030] TIFF2023156259000022.tif26118[In formula (b1-1), L b2represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b3 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the saturated hydrocarbon group may be substituted 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 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b5 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the saturated hydrocarbon group may be substituted 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 b6 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. L b7 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, L b6 and L b7 The total number of carbon atoms is 23 or less.

[0031] In the groups represented by formulae (b1-1) to (b1-3), when -CH2- contained in the saturated hydrocarbon group is replaced with -O- or -CO-, the number of carbon atoms before replacement is defined as the number of carbon atoms of the saturated hydrocarbon group. As the divalent saturated hydrocarbon group, L 1 Examples of the divalent saturated hydrocarbon group include the same as the divalent saturated hydrocarbon group. L b2 is preferably a single bond, a methylene group, —CH(CF3)—, or —C(CF3)2—. L b3 is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b4 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom, and is more preferably a methylene group, -CH(CF3)-, or -C(CF3)2-. L b5 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b6 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b7 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the divalent saturated hydrocarbon group may be substituted with -O- or -CO-. L 1 As the divalent saturated hydrocarbon group represented by the formula (b1-1) or (b1-3), in which one --CH.sub.2-- contained in the group is replaced by --O-- or --CO--, a group represented by the formula (b1-1) or (b1-3) is preferred.

[0032] Examples of the group represented by formula (b1-1) include groups represented by formulas (b1-4) to (b1-8). TIFF2023156259000023.tif49120[In formula (b1-4), L b8represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. In formula (b1-5), L b9 represents a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b10 represents a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b9 and L b10 The total number of carbon atoms is 20 or less. In formula (b1-6), L b11 represents a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b12 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b11 and L b12 The total number of carbon atoms is 21 or less. In formula (b1-7), L b13 represents a divalent saturated hydrocarbon group having 1 to 19 carbon atoms. L b14 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b15 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b13 ~L b15 The total number of carbon atoms is 19 or less. In formula (b1-8), L b16represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b17 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms. L b18 represents a single bond or a divalent saturated hydrocarbon group having 1 to 17 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b16 ~L b18 The total number of carbon atoms is 19 or less. L b8 is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b9 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b10 is preferably 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 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b12 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b13 is preferably a divalent saturated hydrocarbon group having 1 to 12 carbon atoms. L b14 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 6 carbon atoms. L b15 is preferably 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 is preferably a divalent saturated hydrocarbon group having 1 to 12 carbon atoms. L b17 is preferably a divalent saturated hydrocarbon group having 1 to 6 carbon atoms. L b18is preferably 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] Examples of the group represented by formula (b1-3) include groups represented by formulas (b1-9) to (b1-11). TIFF2023156259000024.tif23140[In formula (b1-9), L b19 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b20 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxy group, or an alkylcarbonyloxy group. -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and a hydrogen atom contained in the alkylcarbonyloxy group may be substituted with a hydroxy group. However, L b19 and L b20 The total number of carbon atoms is 23 or less. In formula (b1-10), L b21 represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b22 represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b23 represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxy group, or an alkylcarbonyloxy group. -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and a hydrogen atom contained in the alkylcarbonyloxy group may be substituted with a hydroxy group. However, L b21 , L b22 and Lb23 The total number of carbon atoms is 21 or less. In formula (b1-11), L b24 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b25 represents a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b26 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxy group, or an alkylcarbonyloxy group. -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and a hydrogen atom contained in the alkylcarbonyloxy group may be substituted with a hydroxy group. However, L b24 , L b25 and L b26 The total number of carbon atoms is 21 or less. In addition, in the groups represented by formulae (b1-9) to (b1-11), when a hydrogen atom contained in the saturated hydrocarbon group is substituted with an alkylcarbonyloxy group, the number of carbon atoms before substitution is regarded as the number of carbon atoms of the saturated hydrocarbon group. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, a cyclohexylcarbonyloxy group, and an adamantylcarbonyloxy group.

[0034] Examples of the group represented by formula (b1-4) include the following. TIFF2023156259000025.tif14134

[0035] Examples of the group represented by formula (b1-5) include the following. TIFF2023156259000026.tif60150

[0036] Examples of the group represented by formula (b1-6) include the following. TIFF2023156259000027.tif29165

[0037] Examples of the group represented by formula (b1-7) include the following. TIFF2023156259000028.tif41170

[0038] Examples of the group represented by formula (b1-8) include the following. TIFF2023156259000029.tif20123

[0039] Examples of the group represented by formula (b1-2) include the following. TIFF2023156259000030.tif31161

[0040] Examples of the group represented by formula (b1-9) include the following. TIFF2023156259000031.tif34152

[0041] Examples of the group represented by formula (b1-10) include the following. TIFF2023156259000032.tif80165

[0042] Examples of the group represented by formula (b1-11) include the following. TIFF2023156259000033.tif67153

[0043] Y 1 Examples of the cyclic hydrocarbon group represented by the formula (I) include an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are combined.

[0044] Y 1 Examples of the alicyclic hydrocarbon group in which -CH2- is not replaced by -O-, -S-, -SO2- or -CO- include groups represented by formulae (Y1) to (Y11) and (Y36) to (Y38). Y1 When -CH2- contained in the alicyclic hydrocarbon group represented by the formula (Y12) is replaced by -O-, -S-, -SO2- or -CO-, the number may be one or more. Examples of such groups include groups represented by formulas (Y12) to (Y35) and formulas (Y39) to (Y43). -O- or -CO- in the groups represented by formulas (Y12) to (Y35) and formulas (Y39) to (Y43) may be replaced by -S- or -SO2-. * represents L 1 represents the binding site with TIFF2023156259000034.tif85164

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

[0046] Y 1Examples of the aromatic hydrocarbon group represented by the formula (I) include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The aromatic hydrocarbon group preferably has 6 to 24 carbon atoms, more preferably 6 to 20 carbon atoms, even more preferably 6 to 18 carbon atoms, still more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0047] Y 1 The substituent of the methyl group represented by the formula (I) is a halogen atom, a hydroxy group, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, a glycidyloxy group, -(CH2) ja -CO-OR b1 group 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 combination thereof. ja represents an integer of 0 to 4. -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced by -O-, -SO2-, or -CO-, and a hydrogen atom contained in the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may be replaced by a hydroxy group or a fluorine atom. Y 1 Examples of the substituent of the cyclic hydrocarbon group represented by the formula (I) include a halogen atom, a hydroxy group, an alkyl group having 1 to 16 carbon atoms which may be substituted with a hydroxy group (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, an aralkyl group having 7 to 21 carbon atoms, a glycidyloxy group, -(CH2) ja -CO-OR b1 group or -(CH2) ja -O-CO-R b1 group (in the formula, R b1represents 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 combination thereof. ja represents an integer of 0 to 4. -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced by -O-, -SO2-, or -CO-, and a hydrogen atom contained in the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may be replaced by a hydroxy group or a fluorine atom.

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

[0049] Y 1 is preferably an alicyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent or an aromatic hydrocarbon group of 6 to 24 carbon atoms which may have a substituent, more preferably an alicyclic hydrocarbon group of 3 to 20 carbon atoms which may have a substituent or an aromatic hydrocarbon group of 6 to 20 carbon atoms which may have a substituent, even more preferably an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent or an aromatic hydrocarbon group of 6 to 18 carbon atoms which may have a substituent, and even more preferably an adamantyl group which may have a substituent, a norbornyl group which may have a substituent, or a phenyl group which may have a substituent, wherein -CH2- constituting the alicyclic hydrocarbon group, adamantyl group, and norbornyl group may be replaced by -O-, -S-, -SO2-, or -CO-, and specific examples thereof include the following. TIFF2023156259000035.tif166158Among them, Y 1 is preferably 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 formula (Y42), formula (Y100) to formula (Y114), or formula (Y134) to formula (Y139), and particularly preferably a hydroxyadamantyl group, an oxoadamantyl group, a group containing these, or a group represented by formula (Y42), formula (Y100) to formula (Y114), or formula (Y134) to formula (Y139).

[0050] The anion represented by formula (IA) is preferably an anion represented by formula (IA-1) to formula (IA-85) (hereinafter, sometimes referred to as "anion (IA-1)" or the like depending on the formula number), and more preferably an anion represented by any of formulas (IA-1) to (IA-4), (IA-9), (IA-10), (IA-24) to (IA-33), (IA-36) to (IA-40), and (IA-47) to (IA-81). TIFF2023156259000036.tif232169

[0051] JPEG2023156259000037.jpg231154

[0052] JPEG2023156259000038.jpg205163

[0053] TIFF2023156259000039.tif132161

[0054] where R i2 ~R i7 are each independently, for example, an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group. i8 is, 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 combining these, more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. A41 Q is a single bond or an alkanediyl group having 1 to 4 carbon atoms. 1 and Q 2 has the same meaning as above. Specific examples of the anion represented by formula (IA) include the anions described in JP-A-2010-204646.

[0055] Preferable examples of the anion represented by formula (IA) include anions represented by formulas (Ia-1) to (Ia-65). TIFF2023156259000040.tif247165

[0056] TIFF2023156259000041.tif87160

[0057] TIFF2023156259000042.tif137153

[0058] Among these, anions represented by any one of formulas (Ia-1) to (Ia-4), (Ia-7) to (Ia-11), (Ia-14) to (Ia-30), and (Ia-35) to (Ia-55) are preferred. TIFF2023156259000043.tif3081[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, the cyclic hydrocarbon group optionally having a substituent, and -CH2- contained in the hydrocarbon group optionally being replaced by -O-, -S-, -SO2- or -CO-. R 22 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and one --CH.sub.2-- contained in the alkyl group may be replaced with --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 from each other.]

[0059] In formula (IB), R 21 Examples of the hydrocarbon group containing a cyclic hydrocarbon group in R include cyclic hydrocarbon groups such as monocyclic or polycyclic alicyclic hydrocarbon groups and aromatic hydrocarbon groups, or groups combining these, and groups 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.). 21The number of carbon atoms in the cyclic hydrocarbon group in R 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 groups 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, still more preferably 3 to 24, even more preferably 3 to 18, and even more preferably 3 to 16.

[0060] The alicyclic hydrocarbon group may be monocyclic, polycyclic, or spirocyclic, and may be saturated or unsaturated. Examples of the alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl, and polycyclic cycloalkyl groups such as decahydronaphthyl, norbornyl, and adamantyl. Specific examples of the alicyclic hydrocarbon group include the groups shown below: The bonding site can be at any position. TIFF2023156259000044.tif47168 More specifically, examples of the alicyclic hydrocarbon group include the groups shown below, where * represents a binding site. The alicyclic hydrocarbon group preferably has 3 to 24 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 16 carbon atoms, and even more preferably 5 to 16 carbon atoms. Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The aromatic hydrocarbon group preferably has 6 to 24 carbon atoms, more preferably 6 to 18 carbon atoms, even more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0061] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. Examples of the alkynyl group include an ethynyl group, a propynyl group, an isopropynyl group, a butynyl group, an isobutynyl group, a tert-butynyl group, a pentynyl group, a hexynyl group, an octynyl group, and a nonynyl group. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 24, more preferably 1 to 18, even more preferably 1 to 12, still more preferably 1 to 8, even more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0062] The combined groups are: Examples of such groups include a group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group, a group combining an alicyclic hydrocarbon group with an open-chain hydrocarbon group, a group combining an aromatic hydrocarbon group with an open-chain hydrocarbon group, and a group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group and an open-chain hydrocarbon group, etc. Here, -CH2- in the combined group may be replaced by -O-, -S-, -CO- or -SO2-. In addition, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. Any of the groups may be bonded to an oxygen atom. The above groups may also contain groups with different valences (e.g., alkanediyl groups, alkanetriyl groups, cycloalkanediyl groups, cycloalkanetriyl groups).

[0063] Specific examples of combined groups include: Alicyclic hydrocarbon group-chain hydrocarbon group-* such as an adamantylmethyl group, an adamantylethyl group, a cyclohexylmethyl group, or a cyclohexylethyl group (-CH2- contained in the chain hydrocarbon group or the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-), A chain hydrocarbon group-alicyclic hydrocarbon group-* such as a methyladamantyl group, a methylcyclohexyl group, or a dimethylcyclohexyl group (-CH2- contained in the chain hydrocarbon group or the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-), a chain hydrocarbon group-aromatic hydrocarbon group-* (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), such as a tolyl group or a xylyl group; A chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), such as a methylcyclohexylmethyl group; an aromatic hydrocarbon group-chain hydrocarbon group-* (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), such as a benzyl group or a phenethyl group; a chain hydrocarbon group-aromatic hydrocarbon group-chain hydrocarbon group-* (wherein —CH— contained in the chain hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—), such as a tolylmethyl group; an aromatic hydrocarbon group-alicyclic hydrocarbon group-* (wherein —CH— contained in the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—), such as a phenyladamantyl group; an alicyclic hydrocarbon group-aromatic hydrocarbon group-* (wherein —CH— contained in the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—), such as a cyclohexylphenyl group or an adamantylphenyl group; A chain hydrocarbon group-alicyclic hydrocarbon group-aromatic hydrocarbon group-* such as a methylcyclohexylphenyl group or a dimethylcyclohexylphenyl group (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), A chain hydrocarbon group-aromatic hydrocarbon group-alicyclic hydrocarbon group-* such as a methylphenylcyclohexyl group or a dimethylphenylcyclohexyl group (-CH2- contained in the chain hydrocarbon group or the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), an alicyclic hydrocarbon group-chain hydrocarbon group-aromatic hydrocarbon group-* such as a cyclohexylmethylphenyl group or a cyclohexylethylphenyl group (wherein —CH— contained in the chain hydrocarbon group or the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—); an aromatic hydrocarbon group-a chain hydrocarbon group-an alicyclic hydrocarbon group* such as a phenylmethylcyclohexyl group or a phenylethylcyclohexyl group (wherein —CH— contained in the chain hydrocarbon group or the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—); an alicyclic hydrocarbon group-aromatic hydrocarbon group-chain hydrocarbon group-* such as a cyclohexylphenylmethyl group or a cyclohexylphenylethyl group (wherein —CH— contained in the chain hydrocarbon group or the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—); an aromatic hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group* such as a phenylcyclohexylmethyl group or a phenylcyclohexylethyl group (wherein —CH— contained in the chain hydrocarbon group or the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—); Here, * indicates the bonding site with the oxygen atom.

[0064] R 21When -CH2- in the hydrocarbon group represented by the formula (I) is replaced with -O-, -S-, -CO-, or -SO2-, the number of carbon atoms before the replacement is counted as the total number of carbon atoms in the hydrocarbon group. The number may be 1 or 2 or more. Examples of groups in which -CH2- in a hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), and an alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced by -S-). a group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), an alkoxycarbonyl 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-), an alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), 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- a carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), a thio group (a group in which -CH2- in a methylene group is replaced with -S-), a sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), an alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -O-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which an alkanediyl group in which -CH2- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -CO-O-), an alkanediylthio group (a group in which -CH2- at any position in an alkanediyl group is replaced with -S-), an alkanediylsulfonyl group (a group in which -CH2- at any position in an alkanediyl group is replaced with -SO2-), a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group,Examples include an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group formed by combining two or more of these groups. Examples of the alkoxy group include alkoxy groups having 1 to 17 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, etc. 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 still more preferably 1 to 3. Examples of the alkylthio group include alkylthio groups having 1 to 17 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a 2-ethylhexylthio group, a nonylthio group, a decylthio group, an undecylthio group, etc. 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 still more preferably 1 to 3. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 17 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 18 carbon atoms, such as acetyl, propionyl, and butyryl. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 17 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy. 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 alkylcarbonyloxy group preferably has 2 to 11 carbon atoms, more preferably 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and even more preferably 2 or 3 carbon atoms. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 17 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a 2-ethylhexylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, etc. 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 still more preferably 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 17 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. 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 still more preferably 1 to 3. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 17 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 18 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 17 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. 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 still 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 still 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 still more preferably 2 or 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 17 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. 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 still more preferably 1 to 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 17 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. 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 still more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 17 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 17 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 18 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 17 carbon atoms, such as a phenyloxy group. Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2- include the groups shown below. -O- or -CO- in the groups shown below may be replaced with -S- or -SO2-. The bonding site may be at any position. TIFF2023156259000046.tif47169 More specifically, examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2- include the groups shown below. * represents a bonding site. TIFF2023156259000047.tif54153

[0065] Examples of the substituent that the cyclic hydrocarbon group may have include a halogen atom, a cyano group, and an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO-, or -SO2-). When the cyclic hydrocarbon group has a substituent, the substituent is selected from the group represented by R 21 is not included in the total number of carbon atoms of the hydrocarbon group including the cyclic hydrocarbon group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a nonyl group, etc. 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, still more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. When -CH- in an alkyl group is replaced with -O-, -S-, -CO-, or -SO- as a substituent, the number of carbon atoms before the replacement is counted as the total number of carbon atoms in the alkyl group. Examples of the replaced group include a hydroxy group (a group in which a -CH- in a methyl group is replaced with -O-), a carboxy group (a group in which a -CH- in an ethyl group is replaced with -O-CO-), an alkoxy group (a group in which a -CH- at any position in an alkyl group is replaced with -O-), an alkoxycarbonyl group (a group in which a -CH- at any position in an alkyl group is replaced with -O-CO-), an alkylcarbonyl group (a group in which a -CH- at any position in an alkyl group is replaced with -CO-), an alkylcarbonyloxy group (a group in which a -CH-CH- at any position in an alkyl group is replaced with -CO-O-), and a group combining two or more of these groups. Examples of the alkoxy group include alkoxy groups having 1 to 11 carbon atoms. Examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, and an undecyloxy group. 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 alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 11 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 12 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 11 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. 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 or more substituents. The substituent that the cyclic hydrocarbon group may have is preferably a halogen atom or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO- or -SO2-), more preferably a fluorine atom, an iodine atom or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO- or -SO2-), still more preferably a fluorine atom, an iodine atom, a hydroxy group, an alkoxy group having 1 to 3 carbon atoms or an alkyl group having 1 to 4 carbon atoms, and still more preferably a fluorine atom, an iodine atom, a hydroxy group or an alkyl group having 1 to 4 carbon atoms.

[0066] The cyclic hydrocarbon group (which may have a substituent, and in which -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-) is It is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have a substituent, and —CH— contained in the alicyclic hydrocarbon group may be replaced by —O—, —S—, —SO— or —CO—), or an aromatic hydrocarbon group having 6 to 18 carbon atoms (the aromatic hydrocarbon group may have a substituent), more 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 an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom, and -CH- 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 one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom); It is more preferably an alicyclic hydrocarbon group having 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 hydroxy group, an iodine atom, and a fluorine atom, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, or -CO-).

[0067] R 21 Examples of the hydrocarbon group having 3 to 48 carbon atoms containing a cyclic hydrocarbon group represented by the formula (the cyclic hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-) include: Preferably, it is 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 a substituent, and -CH2- included 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 a substituent, and -CH2- included in the hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-), More preferably, it is a hydrocarbon group having 3 to 48 carbon atoms containing an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have one or more groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom, and -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 containing an aromatic hydrocarbon group having 6 to 18 carbon atoms (the aromatic hydrocarbon group may have one or more groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom, and -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), More preferred are alicyclic hydrocarbon groups having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom, and -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-), and groups in which an alicyclic hydrocarbon group having 3 to 18 carbon atoms is combined with a chain hydrocarbon group having 1 to 6 carbon atoms (the alicyclic hydrocarbon group may have one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom, and -CH2- contained in the combined group is replaced with -O-, -S-, 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 hydroxy group, an iodine atom, and a fluorine atom), or a group in combination of an aromatic hydrocarbon group having 6 to 18 carbon atoms and a chain hydrocarbon group having 1 to 6 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 hydroxy group, an iodine atom, and a fluorine atom, and -CH2- in the combined group may be replaced by -O-, -S-, -SO2-, or -CO-); Even more preferably, it is an alicyclic hydrocarbon group having 5 to 16 carbon atoms (the alicyclic hydrocarbon group may have one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom, and -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 with a chain hydrocarbon group having 1 to 4 carbon atoms (the alicyclic hydrocarbon group may have one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom, and -CH2- contained in the combined group may be replaced with -O-, -S-, -SO2-, or -CO-). Also, R 21 Examples of the hydrocarbon group having 3 to 48 carbon atoms containing a cyclic hydrocarbon group represented by the formula (the cyclic hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-) include: W 21 -L 21 -*(W 21 represents a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-. 21 represents a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms, and -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-. * represents a bonding site with an oxygen atom. ) is also preferred. W 21 cyclic hydrocarbon group, W 21 the substituents which may be present on L 21 Examples of the chain hydrocarbon group include the same groups as those described above. W 21is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the alicyclic hydrocarbon group may have a substituent, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms (the aromatic hydrocarbon group may have a substituent), and 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 an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom and a fluorine atom, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or and -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 hydroxy group, an iodine atom, and a fluorine atom), and even more preferably an alicyclic hydrocarbon group having 5 to 16 carbon atoms (the alicyclic hydrocarbon group may have one or more selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an iodine atom, and a fluorine atom, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, or -CO-). L 21 is preferably a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms (-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 (-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 of 1 to 5, preferably an integer of 1 to 4, more preferably an integer of 1 to 3, even more preferably 1 or 2, and even more preferably 2. When m21 is 1 or 2, SO3 - is preferably the following structure, which is m-substituted with respect to TIFF2023156259000048.tif31102In the above formula, R 21’ is the above-mentioned R 21 has the same definition as R21 may be the same as or different from.

[0068] R 22 Examples of the alkyl group having 1 to 6 carbon atoms include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 4, and more preferably 1 to 3. R 22 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 22 are each independently preferably a halogen atom or an alkyl group having 1 to 4 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), more preferably a fluorine atom, an iodine atom or an alkyl group having 1 to 3 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), and further preferably a fluorine atom, an iodine atom, a hydroxy group, a methoxy group or a methyl group. m22 is an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably an integer of 0 to 2. In one embodiment, m22 is preferably 0. In another embodiment, m22 is preferably 1 or 2. When m22 is 1, R 22 is preferably a halogen atom, and R 22 is more preferably a fluorine atom or an iodine atom. When m22 is 2, R 22 Preferably, one of R is a halogen atom and the other is a halogen atom or an alkyl group having 1 to 4 carbon atoms, 22 It is more preferable that one of the groups is a fluorine atom or an iodine atom, and the other is a fluorine atom, an iodine atom, or an alkyl group having 1 to 3 carbon atoms.

[0069] Examples of the anion (IB) include the following anions. Among them, the anions represented by formulae (IB-1) to (IB-20) are preferred, and the anions represented by formulae (IB-1) to (IB-11) and (IB-16) to (IB-20) are more preferred. TIFF2023156259000049.tif162161

[0070] AI - Examples of the sulfonylimide anion represented by the formula (I) include the following. TIFF2023156259000050.tif26141 Examples of sulfonylmethide anions include the following: TIFF2023156259000051.tif26133

[0071] Specific examples of the salt (I) include salts formed by any combination of the above-mentioned cations and anions. Specific examples of the salt (I) are shown in the table below. In the table below, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation, and "~" indicates that the salt (I) corresponds to the anion (I) or cation (I), respectively. For example, salt (I-1) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-1), salt (I-2) is a salt consisting of an anion represented by formula (Ia-2) and a cation represented by formula (Ic-1), and salt (I-39) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-2). TIFF2023156259000052.tif6291 [Table 1] TIFF2023156259000054.tif223155 TIFF2023156259000055.tif223156 TIFF2023156259000056.tif223156 TIFF2023156259000057.tif223156 TIFF2023156259000058.tif67147

[0072] Among these, salt (I) is preferably a salt obtained by combining an anion represented by any one of 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 one of formulas (Ic-1) to (Ic-95), 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 salt (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),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-3420), Salt (I-3421) ~ Salt (I-3424), Salt (I-3427) ~ Salt (I-343 1), Salt (I-3434) ~ Salt (I-3450), Salt (I-3455) ~ Salt (I-3458), Salt (I-3459) ~ Salt (I-3462), Salt (I-3465) ~ Salt (I-3469), Salt (I-3472) ~ Salt (I-3488), Salt (I-3493) ~ Salt (I-3496), Salt (I-3497) ~ Salt (I-3 500), Salt (I-3503) ~ Salt (I-3507), Salt (I-3510) ~ Salt (I-3526), ​​Salt (I-3531) ~ Salt (I-3534), Salt (I-3535) ~ Salt (I-3538), Salt (I-3541) ~ Salt (I-3545), Salt (I-3548) ~ Salt (I-3564), Salt (I-3569) ~ Salt ( Preferably, the salts are salt (I-3572), salt (I-3573) to salt (I-3576), salt (I-3579) to salt (I-3583), salt (I-3586) to salt (I-3602), salt (I-3607) to salt (I-3610), salt (I-3611) to salt (I-5985), and salt (I-5986) to salt (I-7125).

[0073] <Method for producing salt (I)> The salt (I) can be produced by reacting a salt represented by formula (Ia) with a salt represented by formula (Ib) in a solvent. TIFF2023156259000059.tif118165[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 , X 7 , AI - have the same meanings as above. R A, R B and R C each independently represents a hydrocarbon group having 1 to 12 carbon atoms, or R A , R B and R C may combine to form an aromatic ring. D represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms.] Examples of the solvent include chloroform, monochlorobenzene, acetonitrile, and water. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.

[0074] Examples of the salt represented by formula (Ib) include salts represented by the following formula: These salts can be easily produced by the same method as that described in JP-A Nos. 2011-116747 and 2016-047815, or by known production methods. TIFF2023156259000060.tif168164

[0075] The salt represented by formula (Ia) can be produced by reacting the salt represented by formula (Ic), a compound represented by formula (I-d1), a compound represented by formula (I-d2), and a compound represented by formula (I-d3) in a solvent in the presence of a catalyst. TIFF2023156259000061.tif149156 [wherein all symbols have the same meanings as defined above.] Examples of the catalyst include sodium hydride and potassium carbonate. Examples of the solvent include chloroform, monochlorobenzene, acetonitrile, and water. The reaction temperature is usually 15° C. to 100° C., and the reaction time is usually 0.5 to 24 hours.

[0076] Examples of the salt represented by formula (Ic) include salts represented by the following formula, which are readily available on the market. TIFF2023156259000062.tif28167

[0077] Examples of the compounds represented by formula (I-d1), (I-d2), and (I-d3) include the compounds represented by the following formulae, which are readily available on the market. TIFF2023156259000063.tif53155

[0078] The salt of formula (Ia) can also be produced by reacting a compound of formula (I-d1), a compound of formula (I-d2), and a compound of formula (I-d3) with carbonyldiimidazole in a solvent, and then reacting the resulting mixture with a salt of formula (Ie). JPEG2023156259000064.jpg116170 [wherein all symbols have the same meanings as defined above.] Examples of the solvent include chloroform, monochlorobenzene, and acetonitrile. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.

[0079] Examples of the salt represented by formula (Ie) include salts represented by the following formula, which are readily available on the market. TIFF2023156259000065.tif58150

[0080] <Acid generator> The acid generator of the present invention is an acid generator containing a salt (I), and may contain one kind of salt (I) or two or more kinds of salts (I). The acid generator of the present invention may contain, in addition to the salt (I), an acid generator known in the resist field (hereinafter sometimes referred to as "acid generator (B)"). The acid generator (B) may be used alone or in combination of two or more kinds.

[0081] The acid generator (B) may be either nonionic or ionic. Nonionic acid generators include sulfonate esters (e.g., 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxyketone, diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfone, ketosulfone, sulfonyldiazomethane), etc. Ionic acid generators include onium salts containing onium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts, iodonium salts). Anions of onium salts include sulfonate anions, sulfonylimide anions, sulfonylmethide anions, etc.

[0082] The acid generator (B) may be a compound that generates an acid when exposed to radiation, as described in JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, JP-A-63-146029, U.S. Pat. No. 3,779,778, U.S. Pat. No. 3,849,137, German Patent No. 3,914,407, or European Patent No. 126,712. Compounds produced by known methods may also be used. Two or more types of acid generator (B) may be used in combination.

[0083] 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)). TIFF2023156259000066.tif2962[In formula (B1), Q b1 and Q b2 each 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 b1represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, in which -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-, and in which a hydrogen atom contained in the saturated hydrocarbon group may be replaced by a fluorine atom or a hydroxy group. Y represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and one -CH2- in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-. Z1 + represents an organic cation.

[0084] Q in formula (B1) b1 , Q b2 , L b1 and Y are the same as Q in the above formula (IA), 1 , Q 2 , L 1 and Y 1 And similar things can be mentioned. Examples of the sulfonate anion in formula (B1) include the same anions as those represented by formula (IA).

[0085] TIFF2023156259000067.tif3190[In formula (B2), 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, the cyclic hydrocarbon group optionally having a substituent, and -CH2- contained in the hydrocarbon group optionally being replaced by -O-, -S-, -SO2- or -CO-. R 22 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and one --CH.sub.2-- contained in the alkyl group may be replaced with --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 from each other. Z1 +represents an organic cation.

[0086] m21, m22, and R in formula (B2) 21 and R 22 respectively represent m21, m22, and R in the above formula (IB). 21 and R 22 And similar things can be mentioned. Examples of the sulfonate anion in formula (B2) include the same anions as those represented by formula (IB).

[0087] Z1 + Examples of the organic cation 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 arylsulfonium cations are more preferred. Specific examples include cations represented by any of formulas (b2-1) to (b2-4) (hereinafter, sometimes referred to as "cation (b2-1)" depending on the formula number).

[0088] TIFF2023156259000068.tif46170[Formula (b2-1) to formula (b2-4), R b4 ~R b6 each independently represent 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, a hydrogen atom contained in the chain hydrocarbon group may be substituted with a hydroxy 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, a hydrogen atom contained 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, and a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. Rb4 and R b5 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b7 and R b8 each independently represents a halogen atom, a hydroxy 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 of 0 to 5; When m2 is 2 or more, multiple R b7 may be the same or different, and when n2 is 2 or more, multiple R b8 may be the same or different. R b9 and R b10 each independently represents a chain hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b11 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 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, and a hydrogen atom contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a hydrogen atom 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 may be bonded to each other to form a ring including the -CH-CO- to which they are bonded, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. R b13~R b18 each independently represents a halogen atom, a hydroxy 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 and may be bonded to each other to form a ring containing a sulfur atom together with the benzene ring to which they are attached, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. L b31 represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent an integer of 0 to 5. q2 and r2 each independently represent an integer of 0 to 4; u2 represents 0 or 1. When o2 is 2 or more, multiple R b13 are the same or different, and when p2 is 2 or more, multiple R b14 are the same or different, and when q2 is 2 or more, multiple R b15 are the same or different, and when r2 is 2 or more, multiple R b16 are the same or different, and when s2 is 2 or more, multiple R b17 are the same or different, and when t2 is 2 or more, multiple R b18 are the same or different.] When u2 is 0, any one of o2, p2, q2, and r2 is 1 or more, and R b13 ~R b16 At least one of o2, p2, s2, t2, q2 and r2 is preferably a halogen atom, and when u2 is 1, any one of o2, p2, s2, t2, q2 and r2 is 1 or more, and R b13 ~R b18 At least one of these is preferably a halogen atom. Furthermore, when u2 is 0, r2 is preferably 1 or more, and more preferably 1. When u2 is 0 and r2 is 1 or more, R b16 is preferably a halogen atom. The aliphatic hydrocarbon group refers to a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of the chain hydrocarbon group 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 hydrocarbon group preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups: TIFF2023156259000069.tif10158 In particular, R b9 ~R b12 The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, and more preferably has 4 to 12 carbon atoms. Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include a methylcyclohexyl group, a dimethylcyclohexyl group, a 2-methyladamantan-2-yl group, a 2-ethyladamantan-2-yl group, a 2-isopropyladamantan-2-yl group, a methylnorbornyl group, an isobornyl group, etc. In the alicyclic hydrocarbon group 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. The fluorinated alkyl group refers to an alkyl group having 1 to 12 carbon atoms and a fluorine atom, and examples thereof include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluorobutyl group, etc. 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.

[0089] Examples of aromatic hydrocarbon groups include aryl groups such as phenyl, biphenyl, naphthyl, and phenanthryl. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples include aromatic hydrocarbon groups having a chain hydrocarbon group of 1 to 18 carbon atoms (such as tolyl, xylyl, cumenyl, mesityl, p-ethylphenyl, p-tert-butylphenyl, 2,6-diethylphenyl, and 2-methyl-6-ethylphenyl), and aromatic hydrocarbon groups having an alicyclic hydrocarbon group of 3 to 18 carbon atoms (such as p-cyclohexylphenyl and p-adamantylphenyl). When the aromatic hydrocarbon group has a chain hydrocarbon group or an alicyclic hydrocarbon group, chain hydrocarbon groups having 1 to 18 carbon atoms and alicyclic hydrocarbon groups having 3 to 18 carbon atoms are preferred. Examples of aromatic hydrocarbon groups in which hydrogen atoms are substituted with alkoxy groups include p-methoxyphenyl groups. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as benzyl, phenethyl, phenylpropyl, trityl, naphthylmethyl, and naphthylethyl. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkylcarbonyloxy group include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, an isopropylcarbonyloxy group, a butylcarbonyloxy group, a sec-butylcarbonyloxy group, a tert-butylcarbonyloxy group, a pentylcarbonyloxy group, a hexylcarbonyloxy group, an octylcarbonyloxy group, and a 2-ethylhexylcarbonyloxy group. R b4 and R b5and bond to each other together with the sulfur atom to which they are bonded to form a ring which may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. This ring may be a ring having 3 to 18 carbon atoms, preferably a ring having 4 to 18 carbon atoms. The ring containing a sulfur atom may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring, for example, the following rings. * represents a bonding site. TIFF2023156259000070.tif23143R b9 and R b10 The ring formed by these together may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. This ring may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring. Examples thereof include a thiolan-1-ium ring (tetrahydrothiophenium ring), a thian-1-ium ring, and a 1,4-oxathian-4-ium ring. R b11 and R b12 The ring formed by combining these may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of this ring include a 3- to 12-membered ring, and preferably a 3- to 7-membered ring. Examples include an oxocycloheptane ring, an oxocyclohexane ring, an oxonorbornane ring, and an oxoadamantane ring.

[0090] Among the cations (b2-1) to (b2-4), the cation (b2-1) is preferred. Examples of the cation (b2-1) include the following cations. TIFF2023156259000071.tif161163 Examples of the cation (b2-2) include the following cations. TIFF2023156259000072.tif17150Examples of the cation (b2-3) include the following cations. TIFF2023156259000073.tif24126 Examples of the cation (b2-4) include the following cations. TIFF2023156259000074.tif152163

[0091] The acid generator (B) is a combination of the above-mentioned anion and the above-mentioned organic cation, and these can be combined arbitrarily. Preferred examples of the acid generator (B) include a combination of an anion represented by any of 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 (b2-1), (b2-2), (b2-3), or (b2-4).

[0092] Preferred examples of the acid generator (B) include those represented by formulae (B1-1) to (B1-105) and (B2-1) to (B2-20). Among these, those containing an arylsulfonium cation are preferred, and those represented by formulae (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. TIFF2023156259000075.tif248168

[0093] TIFF2023156259000076.tif243160

[0094] JPEG2023156259000077.jpg255166

[0095] TIFF2023156259000078.tif248163

[0096] TIFF2023156259000079.tif233163

[0097] TIFF2023156259000080.tif228168

[0098] When the acid generator contains a salt (I) and an acid generator (B), the ratio of the salt (I) to the 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.

[0099] <Resist composition> The resist composition of the present invention contains an acid generator containing the salt (I) of the present invention. The resist composition of the present invention preferably further contains a resin (hereinafter sometimes referred to as "resin (A)") containing a structural unit having an acid labile group. Herein, the term "acid labile group" refers to a group that has a leaving group and that is eliminated upon contact with an acid, converting the structural unit into a structural unit having a hydrophilic group (e.g., a hydroxy group or a carboxy group). The resist composition of the present invention preferably contains a quencher such as a salt that generates an acid with a weaker acidity than the acid generated from the acid generator (hereinafter may be referred to as "quencher (C)"), and preferably contains a solvent (hereinafter may be referred to as "solvent (E)").

[0100] <Acid generator> In the resist composition of the present invention, the total content of the acid generators is preferably 1 to 45% by mass, more preferably 1 to 40% by mass, and even more preferably 3 to 35% by mass, relative to the solid content of the resist composition. Furthermore, the content of the acid generators is preferably 1 to 45 parts by mass, more preferably 1 to 40 parts by mass, and even more preferably 3 to 40 parts by mass, relative to 100 parts by mass of the resin (A) described below.

[0101] <Resin (A)> Resin (A) contains a structural unit having an acid labile group (hereinafter sometimes referred to as "structural unit (a1)"). Resin (A) preferably further contains a structural unit other than structural unit (a1). Examples of structural units other than structural unit (a1) include a structural unit not having an acid labile group (hereinafter sometimes referred to as "structural unit (s)"), structural units other than structural unit (a1) and structural unit (s) (for example, a structural unit having a halogen atom (hereinafter sometimes referred to as "structural unit (a4)") described below, a structural unit having a non-leaving hydrocarbon group (hereinafter sometimes referred to as "structural unit (a5)") described below, and other structural units derived from monomers known in the art.

[0102] <Structural unit (a1)> The structural unit (a1) is derived from a monomer having an acid labile group (hereinafter sometimes referred to as "monomer (a1)"). The acid labile group contained in the resin (A) is preferably a group represented by formula (1) (hereinafter also referred to as group (1)) and / or a group represented by formula (2) (hereinafter also referred to as group (2)). TIFF2023156259000081.tif2298[In formula (1), R a1 , R a2 and R a3 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 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining any of these; or R a1 and R a2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms. ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * denotes a binding site.] TIFF2023156259000082.tif2278[In formula (2), R a1’ and R a2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R a2’ and R a3’are bonded to each other to form, together with the carbon atom to which they are bonded and X, a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced with -O- or -S-. X represents an oxygen atom or a sulfur atom. na' represents 0 or 1. * denotes a binding site.]

[0103] R a1 , R a2 and R a3 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. R a1 , R a2 and R a3 Examples of the alkenyl group in the formula (I) 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 either 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, and norbornyl groups, as well as the following groups (* indicates a bonding site): a1 , R a2 and R a3 The alicyclic hydrocarbon group preferably has 3 to 16 carbon atoms. TIFF2023156259000083.tif10159R a1 , R a2 and R a3 Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. Preferably, ma is 0 and na is 1. R a1 and R a2 -C(R a1 )(R a2 )(R a3 ) includes the following groups. The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms. * represents the bonding site with -O-. TIFF2023156259000084.tif35157

[0104] R a1’ , R a2’ and R a3’ Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. The alkyl group and the alicyclic hydrocarbon group are represented by R a1 , R a2 and R a3 Examples of the groups include the same as those listed in the above. Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. R a2’ and R a3’ When they are bonded to each other to form a heterocyclic group together with the carbon atoms to which they are bonded and X, -C(R a1’ )(R a2’ )-XR a3’ Examples of the groups include the following: * represents a binding site. TIFF2023156259000085.tif19124R a1’ and R a2’ At least one of these is preferably a hydrogen atom. na' is preferably 0.

[0105] Examples of the group (1) include the following groups. In formula (1), R a1 , R a2 and R a3 is an alkyl group, ma=0, and na=1. The group is preferably a tert-butoxycarbonyl group. In formula (1), R a1 , R a2 together with the carbon atom to which they are attached form an adamantyl group, and R a3 is an alkyl group, ma=0, and na=1. In formula (1), R a1 and R a2are each independently an alkyl group, and R a3 is an adamantyl group, ma=0, and na=1. Specific examples of the group (1) include the following: * represents a binding site. TIFF2023156259000086.tif130165

[0106] Specific examples of group (2) include the following groups: * represents a binding site. TIFF2023156259000087.tif55153

[0107] The monomer (a1) is preferably a monomer having an acid labile group and an ethylenically unsaturated bond, more preferably a (meth)acrylic monomer having an acid labile group.

[0108] Of the (meth)acrylic monomers having an acid labile group, preferred are those having an alicyclic hydrocarbon group having 5 to 20 carbon atoms. When a resin (A) having a structural unit derived from a monomer (a1) having a bulky structure such as an alicyclic hydrocarbon group is used in a resist composition, the resolution of the resist pattern can be improved.

[0109] Examples of structural units derived from a (meth)acrylic monomer having group (1) include a structural unit represented by formula (a1-0) (hereinafter sometimes referred to as structural unit (a1-0)), a structural unit represented by formula (a1-1) (hereinafter sometimes referred to as structural unit (a1-1)), or a structural unit represented by formula (a1-2) (hereinafter sometimes referred to as structural unit (a1-2)). Preferably, at least one structural unit selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2) is used, and more preferably 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 alone or in combination of two or more. TIFF2023156259000088.tif44143 [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or -O-(CH2) 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.

[0110] R a01 , R a4 and R a5 is preferably a hydrogen atom or a methyl group, more preferably a methyl group. L a01 , L a1 and L a2 is preferably an oxygen atom or —O—(CH2) k01 It is —CO—O— (wherein k01 is preferably an integer of any one of 1 to 4, more preferably 1), and more preferably an oxygen atom. R a02 , R a03 , R a04 , R a6 and R a7The alkyl group, alkenyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group and combinations thereof in the formula (1) include R a1 , R a2 and R a3 Examples of the groups include the same groups as those listed in the above. R a02 , R a03 , and R a04 The alkyl group in the formula (I) 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 the formula (I) 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 the formula (I) 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 alicyclic hydrocarbon group preferably has 5 to 12 carbon atoms, and more preferably 5 to 10 carbon atoms. R a02 , R a03 , R a04 , R a6 and R a7 The aromatic hydrocarbon group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms. In the group in which an alkyl group and an alicyclic hydrocarbon group are combined, the total number of carbon atoms in the combination of the alkyl group and the alicyclic hydrocarbon group is preferably 18 or less. In the group in which an alkyl group and an aromatic hydrocarbon group are combined, the total number of carbon atoms in the combination of the alkyl group and the aromatic hydrocarbon group is preferably 18 or less. R a02 and R a03is 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 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 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 of 0 to 3, and more preferably 0 or 1. n1 is preferably an integer of 0 to 3, and more preferably 0 or 1. n1' is preferably 0 or 1.

[0111] Examples of the structural unit (a1-0) include structural units represented by any one of formulas (a1-0-1) to (a1-0-18) and R a01 and structural units in which the methyl group corresponding to the formula (a1-0-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group (an alkyl group having a halogen atom) or another alkyl group, and structural units represented by any of formulas (a1-0-1) to (a1-0-10), (a1-0-13) and (a1-0-14) are preferred. JPEG2023156259000089.jpg102163

[0112] Examples of the structural unit (a1-1) include structural units derived from monomers described in JP-A-2010-204646. Among these, structural units represented by any one of formulas (a1-1-1) to (a1-1-7) and R in the structural unit (a1-1) are preferred. a4A structural unit in which the methyl group corresponding to the formula (a1-1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group is preferred, and a structural unit represented by any one of formulas (a1-1-1) to (a1-1-4) is more preferred. TIFF2023156259000090.tif39169

[0113] The structural unit (a1-2) includes a structural unit represented by any one of formulas (a1-2-1) to (a1-2-14) and R a5 and structural units in which the methyl group corresponding to the formula (a1-2-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group, and structural units represented by any of formulas (a1-2-2), (a1-2-5), (a1-2-6), and (a1-2-10) to (a1-2-14) are preferred. TIFF2023156259000091.tif68163

[0114] When the resin (A) contains the structural unit (a1-0) and / or the structural unit (a1-1) and / or the structural unit (a1-2), the total content of these, based on the total structural units of the resin (A), can be 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. It can also 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 the resin (A) contains the structural unit (a1-0), the content thereof is 5 mol% or more, preferably 10 mol% or more, based on the total structural units of the resin (A). Also, the content is 80 mol% or less, preferably 75 mol% or less, and more preferably 70 mol% or less. Specifically, the content is 5 to 80 mol%, preferably 5 to 75 mol%, and more preferably 10 to 70 mol%. When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), the total content of these structural units, based on the total structural units of the resin (A), can be 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. It can also be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, still more preferably 75 mol% or less, and even more preferably 70 mol% or less. Specifically, it can be 10 to 95 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%.

[0115] An example of the structural unit (a1) having the group (2) is a structural unit represented by formula (a1-4) (hereinafter, sometimes referred to as "structural unit (a1-4)"). TIFF2023156259000092.tif4563[In formula (a1-4), R a32 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a33 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 a30 is a single bond or *-X a31 -(A a32 -X a32 ) nc - represents -R a32 represents the bonding site with the carbon atom to which it is bonded. A a32 represents an alkanediyl group having 1 to 8 carbon atoms. X a31 and Xa32 each independently represents -O-, -CO-O- or -O-CO-. nc represents 0 or 1. la represents an integer of 0 to 4. When la is an integer of 2 or more, a plurality of R a33 may be the same or different from each other. R a34 and R a35 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a36 represents a hydrocarbon group having 1 to 20 carbon atoms, or R a35 and R a36 are bonded to each other to form, together with the -CO- to which they are bonded, a divalent hydrocarbon group having 2 to 20 carbon atoms, and the hydrocarbon group and the -CH2- contained in the divalent hydrocarbon group may be replaced by -O- or -S-.]

[0116] R a32 and R a33 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, and a bromine atom. R a32 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in the formula (I) include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, and a perfluorohexyl group. R a32 is preferably 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 a33Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a33 Examples of the alkoxy group in include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. R a33 Examples of the alkoxyalkyl group in the formula (I) include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a 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. R a33 Examples of the alkoxyalkoxy group in include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group. R a33 Examples of the alkylcarbonyl group in the formula (I) include an acetyl group, a propionyl group, a butyryl group, etc. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group. R a33Examples of the alkylcarbonyloxy group in the formula (I) include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group. R a33 is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy 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 hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0117] *-X a31 -(A a32 -X a32 ) nc -Examples include *-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-, and *-CO-O- and *-CO-OA are particularly mentioned. a32 -CO-O- or *-OA a32 -CO-O- is preferred. A a32 Examples of the alkanediyl group in the formula (I) include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. A a32 is preferably a methylene group or an ethylene group. A a30 is a single bond, *-CO-O- or *-CO-OA a32-CO-O- is preferred, a single bond, *-CO-O- or *-CO-O-CH2-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.

[0118] 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 the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group in which these groups are combined. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. The alicyclic hydrocarbon group may be either 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, and norbornyl groups, as well as the following groups (* indicates a bonding site): TIFF2023156259000093.tif10151 Examples of aromatic hydrocarbon groups include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. In particular, R a36 Examples of the group include 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 combining these groups.

[0119] R a34 is preferably a hydrogen atom. R a35 is preferably 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 in R 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 combining these, 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 The aromatic hydrocarbon group in is preferably an aromatic ring having an aryloxy group having 6 to 10 carbon atoms.

[0120] -OC(R a34 )(R a35 )-ORa36 is eliminated on contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxy group. -OC(R a34 )(R a35 )-OR a36 is preferably bonded to the o- or p-position of the benzene ring, more preferably to the p-position.

[0121] Examples of the structural unit (a1-4) include structural units derived from monomers described in JP-A-2010-204646. Preferred are structural units represented by formulas (a1-4-1) to (a1-4-24) and R in the structural unit (a1-4). a32 and more preferably, the structural units represented by formulae (a1-4-1) to (a1-4-5), (a1-4-10), (a1-4-13), (a1-4-14), (a1-4-19), and (a1-4-20). TIFF2023156259000094.tif127161 When the resin (A) contains the structural unit (a1-4), the content thereof is preferably 10 to 95 mol %, more preferably 15 to 90 mol %, even more preferably 20 to 85 mol %, still more preferably 20 to 70 mol %, and even more preferably 20 to 60 mol %, based on the total of all structural units in the resin (A).

[0122] Examples of the structural unit derived from a (meth)acrylic monomer having the group (2) include a structural unit represented by formula (a1-5) (hereinafter, sometimes referred to as "structural unit (a1-5)"). TIFF2023156259000095.tif4253[In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom. Z a1 is a single bond or -(CH2) h3 -CO-L 54-, h3 represents an integer of 1 to 4, * represents L 51 represents the binding site with L 51 , L 52 , L 53 and L 54 each independently represents -O- or -S-. s1 represents an integer of 1 to 3. s1' represents an integer of 0 to 3.

[0123] Examples of halogen atoms include fluorine atoms and chlorine atoms, with fluorine atoms being preferred. Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a fluoromethyl group, and a trifluoromethyl group. In formula (a1-5), R a8 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. L 51 is preferably an oxygen atom. L 52 and L 53 Among these, it is preferred that one is —O— and the other is —S—. s1 is preferably 1. s1' is preferably an integer of 0 to 2. Z a1 is preferably a single bond or —CH2—CO—O—.

[0124] Examples of the structural unit (a1-5) include structural units derived from monomers described in JP-A-2010-61117. Among these, the structural units represented by formulas (a1-5-1) to (a1-5-4) are preferred, and the structural unit represented by formula (a1-5-1) or (a1-5-2) is more preferred. TIFF2023156259000096.tif31130

[0125] When the resin (A) contains the structural unit (a1-5), the content thereof 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 %, based on the total structural units of the resin (A).

[0126] Further, examples of the structural unit (a1) include the following structural units. TIFF2023156259000097.tif27161

[0127] When the resin (A) contains structural units such as (a1-3-1) to (a1-3-7), the content thereof 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 %, based on the total structural units of the resin (A).

[0128] <Structural unit(s)> The structural unit (s) is derived from a monomer (hereinafter sometimes referred to as "monomer (s)") that does not have an acid labile group. As the monomer from which the structural unit (s) is derived, a monomer that does not have an acid labile group known in the resist field can be used. The structural unit (s) preferably has a hydroxy group or a lactone ring. The use of a resin containing a structural unit having a hydroxy group but no acid labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring but no acid labile group (hereinafter sometimes referred to as "structural unit (a3)") in the resist composition of the present invention can improve the resolution of the resist pattern and the adhesion to the substrate.

[0129] <Structural unit (a2)> The structural unit (a2) is a structural unit represented by formula (a2) and has an alcoholic hydroxy group or a phenolic hydroxy group. TIFF2023156259000098.tif3095[In formula (a2), R a50represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. 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. W a50 represents a cyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent. L a50 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms which may contain a fluorine atom. ma50 represents an integer of 1 to 5. R a50 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, and a bromine atom. R a50 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, and a perfluorohexyl group. The number of carbon atoms in the alkyl group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. R a50is preferably 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.

[0130] A a50 A in a52 Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. 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 is preferably a methylene group or an ethylene group. *-X a51 -(A a52 -X a52 ) nb -Examples include *-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-, and *-CO-O- and *-CO-OA are particularly mentioned. a52 -CO-O- or *-OA a52 -CO-O- is preferred. A a50 is a single bond, *-CO-O- or *-CO-OA a52 -CO-O- is preferred, a single bond, *-CO-O- or *-CO-O-CH2-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.

[0131] W a50Examples of the cyclic hydrocarbon group include a divalent alicyclic hydrocarbon group and a divalent aromatic hydrocarbon group. W a50 Examples of the monocyclic divalent alicyclic hydrocarbon group in the formula (I) include monocyclic cycloalkanediyl groups such as cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl. Examples of the polycyclic divalent alicyclic hydrocarbon group in the formula (I) 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 The divalent aromatic hydrocarbon group in the formula (I) may be a phenylene group or a naphthyl group. The aromatic hydrocarbon group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms. W a50 Examples of the substituent that the cyclic hydrocarbon group having 5 to 12 carbon atoms may have include a halogen atom, a hydroxy group, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 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. a50 The number of substituents that may be present may be one or two or more. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. 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 group or an 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. 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 the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group. 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 group or an ethoxy group, and even more preferably a methoxy group. Examples of the alkoxyalkyl group include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a 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 the alkoxyalkoxy group include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group. W a50 The substituent of the cyclic hydrocarbon group is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy 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 hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0132] L a50 Examples of the chain hydrocarbon group having 1 to 12 carbon atoms include linear alkanediyl groups such as 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, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl; ethane-1,1-diyl; propane-1,1 Examples of branched alkanediyl groups include 1-methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-dimethylpropane-1,3-diyl, pentane-2,4-diyl, pentane-1,4-diyl, 2-methylbutane-1,4-diyl, pentane-2,4-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. The number of carbon atoms in the chain 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 may have one or more fluorine atoms. ma50 is preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

[0133] When producing a resist pattern from the resist composition of the present invention, if a high-energy ray such as a KrF excimer laser (248 nm), an electron beam, or EUV (extreme ultraviolet) is used as an exposure light source, the structural unit (a2) preferably has a phenolic hydroxy group, and more preferably the structural unit (a2-A) described below. Furthermore, if an ArF excimer laser (193 nm) or the like is used, the structural unit (a2) preferably has an alcoholic hydroxy group, and more preferably the structural unit (a2-1) described below. The structural unit (a2) may contain one type alone or two or more types.

[0134] In the structural unit (a2), an example of a structural unit having a phenolic hydroxy group is a structural unit represented by formula (a2-A) (hereinafter, sometimes referred to as "structural unit (a2-A)"). TIFF2023156259000099.tif4753[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 from each other.

[0135] R a50 and A a50 The groups include the same groups as those exemplified in formula (a2). R a51 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, and a bromine atom. R a51 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a51 Examples of the alkoxy group in include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. R a51 Examples of the alkoxyalkyl group in the formula (I) include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a 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. R a51Examples of the alkoxyalkoxy group in include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group. R a51 Examples of the alkylcarbonyl group in the formula (I) include an acetyl group, a propionyl group, a butyryl group, etc. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group. R a51 Examples of the alkylcarbonyloxy group in the formula (I) include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group. R a51 is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy 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 hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0136] mb is preferably 0, 1 or 2, and more preferably 0 or 1. At least one hydroxy group is preferably bonded to the m-position or p-position of the benzene ring. When two or more hydroxy groups are contained, two hydroxy groups are preferably bonded to the m-position and p-position, respectively.

[0137] Examples of the structural unit (a2-A) include structural units derived from monomers described in JP-A Nos. 2010-204634 and 2012-12577. The structural unit (a2-A) includes structural units represented by formulae (a2-2-1) to (a2-2-24) and R in the structural unit (a2-A) in the structural units represented by formulae (a2-2-1) to (a2-2-24). a50 The structural unit (a2-A) includes structural units represented by formulas (a2-2-1) to (a2-2-4), structural units represented by formula (a2-2-6), structural units represented by formula (a2-2-8), structural units represented by formula (a2-2-12) to (a2-2-18), and structural units represented by formulas (a2-2-1) to (a2-2-4), structural units represented by formula (a2-2-6), structural units represented by formula (a2-2-8), and structural units represented by formula (a2-2-12) to (a2-2-18), in which R in the structural unit (a2-A) is a50 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 formula (a2-2-12) to formula (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 formula (a2-2-12) to formula (a2-2-14), and the structural unit represented by formula (a2-2-18), a50 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), and the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-4), and the structural unit represented by formula (a2-2-8), a50 More preferably, the structural unit is a structural unit in which a methyl group corresponding to the following formula is replaced with a hydrogen atom: TIFF2023156259000100.tif79169

[0138] When the structural unit (a2-A) is contained in the resin (A), the content of the structural unit (a2-A) relative to all structural units is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 15 mol% or more, and still more preferably 20 mol% or more. It is also 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 the resin (A) by, for example, polymerizing the structural unit (a1-4) and then treating with an acid such as p-toluenesulfonic acid. Alternatively, the structural unit (a2-A) can be incorporated into the resin (A) by polymerizing the structural unit (a1-4) and then treating with an alkali such as tetramethylammonium hydroxide.

[0139] Examples of the structural unit (a2-A) include a structural unit represented by the following formula (a2-A1) (hereinafter sometimes referred to as "structural unit (a2-A1)") and a structural unit represented by the following formula (a2-A2) (hereinafter sometimes referred to as "structural unit (a2-A2)"). TIFF2023156259000101.tif52136 [In formula (a2-A1) and formula (a2-A2), R a50 and A a50 have the same meaning as in formula (a2). mb1 represents an integer of 0 to 4. R a52 represents a halogen atom. R a53 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 of 0 to 4, and when mb2 is 2 or more, a plurality of R a52 may be the same or different, and when mb3 is 2 or more, multiple R a53 may be the same or different, and satisfy 1≦mb2+mb3≦4. R a52 The halogen atoms in a50 The substituents of the cyclic hydrocarbon group and R a51 The halogen atoms in R are the same as those in R. a52 The halogen atom is preferably a fluorine atom or an iodine atom. R a53 The alkyl group having 1 to 6 carbon atoms, the alkoxy group having 1 to 6 carbon atoms, the alkoxyalkyl group having 2 to 12 carbon atoms, the alkoxyalkoxy group having 2 to 12 carbon atoms, the alkylcarbonyl group having 2 to 4 carbon atoms, the alkylcarbonyloxy group having 2 to 4 carbon atoms, the acryloyloxy group or the methacryloyloxy group is, respectively, W a50 The substituents of the cyclic hydrocarbon group and R a51 Examples thereof include the same as the alkyl group, alkoxy group, alkoxyalkyl group, alkoxyalkoxy group, alkylcarbonyl group, alkylcarbonyloxy group, acroyloxy group, and methacryloyloxy group in the above formula (1), more preferably a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a methoxy group or an ethoxyethoxy group. mb1 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and further preferably 0 or 1. mb2 is preferably an integer of 0 to 3, more preferably an integer of 1 to 3, and further preferably 1 or 2. mb3 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and further preferably 0 or 1.

[0140] An example of the structural unit (a2) having an alcoholic hydroxy group is a structural unit represented by formula (a2-1) (hereinafter, sometimes referred to as "structural unit (a2-1)"). TIFF2023156259000102.tif4258[In formula (a2-1), L a3 is -O- or *-O-(CH2) k2 represents -CO-O-, k2 represents an integer of 1 to 7. * represents the bonding site with —CO—. R a14 represents a hydrogen atom or a methyl group. R a15 and R a16 each independently represents a hydrogen atom, a methyl group, or a hydroxy group. o1 represents an integer between 0 and 10.

[0141] In equation (a2-1), L a3 is preferably -O-, -O-(CH2) f1 It is —CO—O— (wherein f1 represents an integer of 1 to 4), and more preferably —O—. R a14 is preferably a methyl group. R a15 is preferably a hydrogen atom. R a16 is preferably a hydrogen atom or a hydroxy group. o1 is preferably an integer of 0 to 3, and more preferably 0 or 1.

[0142] Examples of the structural unit (a2-1) include structural units derived from monomers described in JP 2010-204646 A. A structural unit represented by any one of formulas (a2-1-1) to (a2-1-6) is preferred, a structural unit represented by any one of formulas (a2-1-1) to (a2-1-4) is more preferred, and a structural unit represented by formula (a2-1-1) or formula (a2-1-3) is even more preferred. When the resin (A) contains the structural unit (a2-1), the content thereof is 1 mol% or more, preferably 2 mol% or more, based on the total structural units of the resin (A). Alternatively, the content may be 45 mol% or less, 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, the content may be 1 to 45 mol%, 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%.

[0143] An example of the structural unit (a2) having an alcoholic hydroxy group is a structural unit represented by formula (a2-B) (hereinafter, sometimes referred to as "structural unit (a2-B)"). TIFF2023156259000104.tif50104[In formula (a2-B), R a50 and A a50 have the same meaning as in formula (a2). R a54 and R a55 each independently represents a fluorinated alkyl group having 1 to 4 carbon atoms. L a51 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 hydroxy group, a haloalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkyl group may be replaced by -O- or -CO-. mb4 represents an integer of 1 to 3, and when mb4 is 2 or more, multiple R a54 , R a55 and L a51 may be the same or different from each other. mb5 represents an integer from 0 to 4, and when mb5 is 2 or more, multiple R a56may be the same or different, provided that 1≦mb4+mb5≦5.

[0144] R a54 and R a55 Examples of the fluorinated alkyl groups having 1 to 4 carbon atoms in R each independently include a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, and a 4,4,4-trifluorobutyl group. a54 and R a55 As the aryl group, a trifluoromethyl group is preferred. L a51 Examples of the alkanediyl group having 1 to 3 carbon atoms include a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group. a51 is preferably a single bond or a methylene group. R a56 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R a56 The haloalkyl group having 1 to 4 carbon atoms represents an alkyl group having 1 to 4 carbon atoms and a halogen atom, and examples thereof include a chloromethyl group, a bromomethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a perfluorobutyl group. R a56 Examples of the alkyl group having 1 to 12 carbon atoms in the formula include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, octyl group, nonyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 9, more preferably 1 to 6, and even more preferably 1 to 4. R a56 When -CH2- in the alkyl group represented by R is replaced with -O- or -CO-, the number of carbon atoms before the replacement is the total number of carbon atoms in the alkyl group. a56may have a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a carboxyl group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), an alkoxy group having 1 to 11 carbon atoms (a group in which -CH2- 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- 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- 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- in an alkyl group having 3 to 12 carbon atoms is replaced with -CO-O-). R a56 Among these, a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced by -O- or -CO-) is preferred. mb4 is preferably 1 or 2, and more preferably 1. Even more preferably, mb4 is 1 and the group in parentheses is bonded to the para position. mb5 is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0145] The structural unit (a2-B) is more preferably a structural unit represented by the following formula (a2-B1) (hereinafter, sometimes referred to as "structural unit (a2-B1)"). TIFF2023156259000105.tif4787[In formula (a2-B1), R a57 represents a hydrogen atom or a methyl group. A a53 represents a single bond or *-CO-O-, and * represents -R a57 represents the bonding site with the carbon atom to which it is bonded. R a56 , mb4 and mb5 have the same meanings as in formula (a2-B).

[0146] In formula (a2-B1), R a57 is preferably a hydrogen atom. A a53 is preferably a single bond.

[0147] Examples of the structural unit (a2-B) include the structural units shown below. TIFF2023156259000106.tif62168

[0148] In the structural units represented by formulae (a2-B-1) to (a2-B-8), R a57 In the structural units represented by formulae (a2-B-9) to (a2-B-16), the structural unit in which the hydrogen atom corresponding to R is replaced with a methyl group is also a57 Specific examples of the structural unit (a2-B) include structural units in which a methyl group corresponding to the following formula is replaced with a hydrogen atom. 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.

[0149] When the resin (A) contains the structural unit (a2-B), its content is preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, based on the total structural units of the resin (A). It is also 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%.

[0150] <Structural unit (a3)> The lactone ring contained in 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 a condensed ring of a monocyclic lactone ring with another ring. Preferred examples include a γ-butyrolactone ring, an adamantane lactone ring, or a bridged ring containing a γ-butyrolactone ring structure (for example, a structural unit represented by the following formula (a3-2)).

[0151] 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 contained alone, or two or more may be contained. TIFF2023156259000107.tif50161 [In formula (a3-1), formula (a3-2), formula (a3-3) and formula (a3-4), L a4 , L a5 and L a6 are each independently -O- or -O-(CH2) k3 It represents a group represented by —CO—O— (k3 represents an integer of 1 to 7). L a7 -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 independently represents an alkanediyl group having 1 to 6 carbon atoms. * indicates the bonding site with the carbonyl group. R a18 , R a19 , R a20 and R a24 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. X a3 represents -CH2- or an oxygen atom. R a21 represents an aliphatic hydrocarbon group having 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 an integer of 0 to 5. q1 represents an integer of 0 to 3. r1 represents an integer of 0 to 3. w1 represents an integer of 0 to 8. When p1, q1, r1 and / or w1 are 2 or more, multiple R a21 , R a22 , R a23 and / or R a25 may be the same as or different from each other.

[0152] R a21 , R a22 , R a23 and R a25 Examples of the aliphatic hydrocarbon group in include alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, and a tert-butyl group. R a18 , R a19 , R a20 and R a24 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R a18 , R a19 , R a20 and R a24 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group, and preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. R a18 , R a19 , R a20 and R a24Examples of the alkyl group having a halogen atom in the formula (I) include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group. L a8 and L a9 Examples of the alkanediyl group in the formula (I) include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group.

[0153] In formulas (a3-1) to (a3-3), L a4 ~L a6 are each independently preferably -O- or -O-(CH2) k3 In -CO-O-, k3 is a group in which k3 is any integer of 1 to 4, more preferably -O- and *-O-CH2-CO-O-, and even more preferably an oxygen atom. R a18 ~R a21 is preferably a methyl group. R a22 and R a23 are each independently preferably a carboxy group, a cyano group, or a methyl group. p1, q1 and r1 each independently represent an integer of preferably 0 to 2, and more preferably 0 or 1.

[0154] In formula (a3-4), R a24 is preferably 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 a25is preferably a carboxy group, a cyano group or a methyl group. L a7 is preferably -O- or *-OL a8 It is —CO—O—, and more preferably —O—, —O—CH 2 —CO—O— or —O—C 2 H 4 —CO—O—. w1 is preferably an integer of 0 to 2, and more preferably 0 or 1. In particular, the formula (a3-4) is preferably the formula (a3-4)'. TIFF2023156259000108.tif4051(in the formula, R a24 , L a7 has the same meaning as above.)

[0155] Examples of the structural unit (a3) ​​include structural units derived from monomers described in JP 2010-204646 A, JP 2000-122294 A, and JP 2012-41274 A. Examples of the structural unit (a3) ​​include structural units represented by any of 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 structural units, R in formulas (a3-1) to (a3-4) a18 , R a19 , R a20 and R a24 A structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom is preferred.

[0156] When the resin (A) contains the structural unit (a3), the total content thereof, based on all structural units in the resin (A), can be 1 mol% or more, preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more. It can also be 70 mol% or less, preferably 65 mol% or less, and more preferably 60 mol% or less. Specifically, it can be 1 to 70 mol%, preferably 3 to 65 mol%, and more preferably 5 to 60 mol%. Furthermore, the content of the structural unit (a3-1), the structural unit (a3-2), the structural unit (a3-3), or the structural unit (a3-4) is preferably 1 mol% or more, more preferably 3 mol% or more, and even more preferably 5 mol% or more, based on the total structural units of the resin (A). It is also preferably 60 mol% or less, more preferably 55 mol% or less, and even more preferably 50 mol% or less. Specifically, it is preferably 1 to 60 mol%, more preferably 1 to 50 mol%, more preferably 3 to 55 mol%, and even more preferably 5 to 50 mol%.

[0157] <Structural unit (a4)> Examples of the structural unit (a4) include the following structural units. TIFF2023156259000110.tif3066[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 represents a saturated hydrocarbon group having 1 to 24 carbon atoms and containing a fluorine atom, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.] R 42 Examples of the saturated hydrocarbon group represented by the formula (I) include chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these groups.

[0158] Examples of the chain hydrocarbon group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl groups. Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; decahydronaphthyl, adamantyl, norbornyl, and polycyclic alicyclic hydrocarbon groups such as the following groups (* indicates a bonding site): TIFF2023156259000111.tif11159 Examples of groups formed by combination 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.

[0159] The structural unit (a4) includes at least one structural unit selected from the group consisting of formula (a4-0), formula (a4-1), formula (a4-2), formula (a4-3) and formula (a4-4). TIFF2023156259000112.tif4652[In formula (a4-0), R 5 represents a hydrogen atom or a methyl group. L 4a represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 4 carbon atoms. L 3a represents a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluorocycloalkanediyl group having 3 to 12 carbon atoms. R 6 represents a hydrogen atom or a fluorine atom.

[0160] L 4a Examples of the divalent aliphatic saturated hydrocarbon group in the formula (I) include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, and a butane-1,4-diyl group, and branched alkanediyl groups such as an ethane-1,1-diyl group, a propane-1,2-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group. L 3aExamples of the perfluoroalkanediyl group in the formula (I) include a difluoromethylene group, a perfluoroethylene group, a perfluoropropane-1,1-diyl group, a perfluoropropane-1,3-diyl group, a perfluoropropane-1,2-diyl group, a perfluoropropane-2,2-diyl group, a perfluorobutane-1,4-diyl group, a perfluorobutane-2,2-diyl group, a perfluorobutane-1,2-diyl group, a perfluoropentane-1,5-diyl group, a perfluoropentane-2,2-diyl group, a perfluoropentane-3 ,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 the perfluorocycloalkanediyl group in the formula (I) include a perfluorocyclohexanediyl group, a perfluorocyclopentanediyl group, a perfluorocycloheptanediyl group, and a perfluoroadamantanediyl group.

[0161] L 4a is preferably a single bond, a methylene group, or an ethylene group, and more preferably a single bond or a methylene group. L 3a is preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0162] The structural unit (a4-0) includes the structural units shown below and R in the structural unit (a4-0) in the structural units shown below. 5 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2023156259000113.tif100170

[0163] TIFF2023156259000114.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 a substituent, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. A a41 represents an alkanediyl group having 1 to 6 carbon atoms which may have a substituent or a group represented by formula (a-g1), a41 and R a42 At least one of the groups has a halogen atom (preferably a fluorine atom) as a substituent. TIFF2023156259000115.tif1384 [In formula (a-g1), s represents 0 or 1. A a42 and A a44 each independently represents a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. A a43 represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. X a41 and X a42 each independently represents -O-, -CO-, -CO-O- or -O-CO-. However, A a42 , A a43 , A a44 , X a41 and X a42 The total number of carbon atoms is 7 or less. * indicates the binding site, and the * on the right is -O-CO-R a42 ]

[0164] R a42 Examples of the saturated hydrocarbon group in include a chain saturated hydrocarbon group, a monocyclic or polycyclic alicyclic saturated hydrocarbon group, and groups formed by combining these groups. Examples of the chain saturated hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group. Examples of the monocyclic or polycyclic alicyclic saturated hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group; and polycyclic alicyclic saturated hydrocarbon groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following groups (* indicates a bonding site): TIFF2023156259000116.tif11159 Examples of groups formed by this combination 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.

[0165] R a42 Examples of the substituent that may be possessed by include at least one selected from a halogen atom and a group represented by formula (a-g3): Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferred. TIFF2023156259000117.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 have a halogen atom. * represents R a42 represents the binding site with However, R a42 -X a43 -A a45 In R a42 If A does not have a halogen atom, a45 represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms and at least one halogen atom.

[0166] A a45 Examples of the aliphatic hydrocarbon group in the formula (I) include alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group; Examples include monocyclic alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; and polycyclic alicyclic hydrocarbon groups such as decahydronaphthyl, adamantyl, and norbornyl groups, and the following groups (* indicates a bonding site): TIFF2023156259000118.tif11159 Examples of groups formed by combination 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.

[0167] R a42 is preferably an aliphatic hydrocarbon group which may have a halogen atom, and more preferably an aliphatic hydrocarbon group having an alkyl group having a halogen atom and / or a group represented by formula (a-g3). R a42 When 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 perfluoroalkyl groups include perfluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, and perfluorooctyl group. Examples of perfluorocycloalkyl groups include perfluorocyclohexyl group. R a42is an aliphatic hydrocarbon group having a group represented by formula (a-g3), the number of carbon atoms contained in the group represented by formula (a-g3) is a42 The total number of carbon atoms is preferably 15 or less, more preferably 12 or less. When the group represented by formula (a-g3) is contained as a substituent, the number thereof is preferably 1.

[0168] R a42 is an aliphatic hydrocarbon group having a group represented by formula (a-g3), R a42 is more preferably a group represented by formula (a-g2). TIFF2023156259000119.tif879[In formula (a-g2), A a46 represents a divalent aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. X a44 represents **-O-CO- or **-CO-O- (** represents A a46 (representing the binding site with A a47 represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. However, A a46 , A a47 and X a44 The total number of carbon atoms in A is 18 or less. a46 and A a47 At least one of the groups has at least one halogen atom. * indicates the bonding site with the carbonyl group.]

[0169] A a46 The aliphatic hydrocarbon group preferably has 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. A a47 The aliphatic hydrocarbon group preferably has 4 to 15 carbon atoms, more preferably 5 to 12 carbon atoms, and A a47 is more preferably a cyclohexyl group or an adamantyl group.

[0170] A preferred structure of the group represented by formula (a-g2) is the following structure (* indicates the bonding site with the carbonyl group): JPEG2023156259000120.jpg13161

[0171] A a41 Examples of the alkanediyl group in the formula (I) include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and branched alkanediyl groups such as propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-methylbutane-1,4-diyl, and 2-methylbutane-1,4-diyl. A a41 Examples of the substituent in the alkanediyl group include a hydroxy group and an alkoxy group having 1 to 6 carbon atoms. A a41 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.

[0172] A in the group represented by formula (a-g1) a42 , A a43 and A a44 Examples of the divalent saturated hydrocarbon group represented by include a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic hydrocarbon group, and a group formed by combining an alkanediyl group with a divalent alicyclic hydrocarbon group. Specific examples include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group. A a42 , A a43 and A a44 Examples of the substituent of the divalent saturated hydrocarbon group represented by the formula include a hydroxy group and an alkoxy group having 1 to 6 carbon atoms. Preferably, s is 0.

[0173] In the group represented by formula (a-g1), X a42In the following examples, * and ** each represent a bonding site, and ** represents -O-CO-R a42 This is the binding site for TIFF2023156259000121.tif54162

[0174] The structural unit represented by formula (a4-1) includes the structural units shown below and R in the structural unit represented by formula (a4-1) in the structural units shown below. a41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. JPEG2023156259000122.jpg167144

[0175] TIFF2023156259000123.tif66133

[0176] The structural unit represented by formula (a4-1) is preferably a structural unit represented by formula (a4-2). TIFF2023156259000124.tif4365[In formula (a4-2), R f5 represents a hydrogen atom or a methyl group. L 44 represents an alkanediyl group having 1 to 6 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-. R f6 represents a saturated hydrocarbon group having 1 to 20 carbon atoms and containing a fluorine atom. However, L 44 and R f6 The maximum total carbon number is 21.]

[0177] L 44 The alkanediyl group having 1 to 6 carbon atoms is A a41 Examples of the alkanediyl group include the same groups as those exemplified as the alkanediyl group in the above. R f6 The saturated hydrocarbon group of R a42 Examples of the groups include the same groups as those exemplified in L44 As the alkanediyl group having 1 to 6 carbon atoms, an alkanediyl group having 2 to 4 carbon atoms is preferred, and an ethylene group is more preferred.

[0178] Examples of the structural unit represented by formula (a4-2) include structural units represented by formulas (a4-1-1) to (a4-1-11). f5 The structural unit represented by formula (a4-2) also includes a structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom:

[0179] Examples of the structural unit (a4) include a structural unit represented by formula (a4-3). TIFF2023156259000125.tif5771[In formula (a4-3), R f7 represents a hydrogen atom or a methyl group. L 5 represents an alkanediyl group having 1 to 6 carbon atoms. A f13 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms which may contain a fluorine atom. X f12 represents *-O-CO- or *-CO-O- (* represents A f13 represents the binding site with ). A f14 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 L has a fluorine atom, 5 , A f13 and A f14 The total number of carbon atoms in a molecule is limited to 20.

[0180] L 5 The alkanediyl group in a41 Examples of the divalent saturated hydrocarbon group include the same groups as those exemplified as the alkanediyl group. A f13The divalent saturated hydrocarbon group optionally having a fluorine atom in the formula (I) is preferably a divalent chain saturated hydrocarbon group optionally having a fluorine atom and a divalent alicyclic saturated hydrocarbon group optionally having a fluorine atom, and more preferably a perfluoroalkanediyl group. Examples of the divalent chain saturated hydrocarbon group which may have a fluorine atom include alkanediyl groups such as a methylene group, an ethylene group, a propanediyl group, a butanediyl group, and a pentanediyl group; and perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropanediyl group, a perfluorobutanediyl group, and a perfluoropentanediyl group. The divalent alicyclic saturated hydrocarbon group optionally having a fluorine atom may be either monocyclic or polycyclic. Examples of the monocyclic group include a cyclohexanediyl group and a perfluorocyclohexanediyl group. Examples of the polycyclic group include an adamantanediyl group, a norbornanediyl group, and a perfluoroadamantanediyl group. A f14 The saturated hydrocarbon group and the saturated hydrocarbon group which may have a fluorine atom are R a42 Among these, a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, Preferred are fluorinated alkyl groups such as a hexyl group, a perfluorohexyl group, a heptyl group, a perfluoroheptyl group, an octyl group, and a perfluorooctyl group, a cyclopropylmethyl group, a cyclopropyl group, a cyclobutylmethyl group, a cyclopentyl group, a cyclohexyl group, a perfluorocyclohexyl group, an adamantyl group, an adamantylmethyl group, an adamantyldimethyl group, a norbornyl group, a norbornylmethyl group, a perfluoroadamantyl group, and a perfluoroadamantylmethyl group.

[0181] In formula (a4-3), L 5 is preferably an ethylene group. 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 saturated hydrocarbon group having 3 to 12 carbon atoms and a group containing an alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a group containing a chain saturated hydrocarbon group having 3 to 10 carbon atoms and a group containing an alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms. f14 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, or an adamantyl group.

[0182] Examples of the structural unit represented by formula (a4-3) include structural units represented by formulas (a4-1'-1) to (a4-1'-11). f7 The structural unit represented by formula (a4-3) also includes a structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom:

[0183] The structural unit (a4) also includes a structural unit represented by formula (a4-4). TIFF2023156259000126.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 to j5 each independently represent an integer of 1 to 6. Rf22 represents a saturated hydrocarbon group having 1 to 10 carbon atoms and containing a fluorine atom.]

[0184] R f22 The saturated hydrocarbon group of R a42 Examples of saturated hydrocarbon groups include the same as those represented by R f22 is preferably an alkyl group having 1 to 10 carbon atoms and containing a fluorine atom or an alicyclic hydrocarbon group having 1 to 10 carbon atoms and containing a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms and containing a fluorine atom, and even more preferably an alkyl group having 1 to 6 carbon atoms and containing a fluorine atom.

[0185] In formula (a4-4), A f21 As -(CH2) j1 - is preferred, an ethylene group or a methylene group is more preferred, and a methylene group is even more preferred.

[0186] Examples of the structural unit represented by formula (a4-4) include the following structural units and structural units represented by the following formulas: f21 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2023156259000127.tif87160

[0187] When the resin (A) contains the structural unit (a4), the content thereof is preferably 1 to 20 mol %, more preferably 2 to 15 mol %, and even more preferably 3 to 10 mol %, based on all structural units in the resin (A).

[0188] <Structural unit (a5)> The non-leaving hydrocarbon group contained in the structural unit (a5) may be a group containing a linear, branched, or cyclic hydrocarbon group, and among these, the structural unit (a5) is preferably a group containing an alicyclic hydrocarbon group. Examples of the structural unit (a5) include a structural unit represented by formula (a5-1). TIFF2023156259000128.tif3971[In formula (a5-1), R51 represents a hydrogen atom or a methyl group. R 52 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group may be substituted with an aliphatic hydrocarbon group having 1 to 8 carbon atoms. L 55 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.]

[0189] R 52 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of polycyclic alicyclic hydrocarbon groups include adamantyl and norbornyl. Examples of the aliphatic hydrocarbon group 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 the alicyclic hydrocarbon group having a substituent include a 3-methyladamantyl group. R 52 is preferably 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 The divalent saturated hydrocarbon group in the formula (I) includes a divalent saturated chain hydrocarbon group and a divalent saturated alicyclic hydrocarbon group, and is preferably a divalent saturated chain hydrocarbon group. Examples of the divalent chain saturated hydrocarbon group include a methylene group, an ethylene group, and an alkanediyl group such as a propanediyl group, a butanediyl group, and a pentanediyl group. The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic saturated hydrocarbon group include cycloalkanediyl groups such as cyclopentanediyl and cyclohexanediyl. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include adamantanediyl and norbornanediyl.

[0190] L 55 Examples of the divalent saturated hydrocarbon group represented by formula (L1-1) in which one -CH2- is replaced with -O- or -CO- include groups represented by formula (L1-1) to formula (L1-4). In the following formulae, * and ** each represent a bonding site, and * represents a bonding site to an oxygen atom. TIFF2023156259000129.tif18165[In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents L x1 represents the binding site with ). L x1 represents a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. L x2 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 represents a divalent aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms. L x4 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 represents a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. L x6 and L x7 each 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 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms. W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, L x8 , L x9 and W x1 The total number of carbon atoms is 15 or less.

[0191] L x1 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x2 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond. L x3 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x6 is preferably 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 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x8 is preferably 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 is preferably 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 is preferably a divalent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, more preferably a cyclohexanediyl group or an adamantanediyl group.

[0192] Examples of the group represented by formula (L1-1) include the divalent groups shown below. TIFF2023156259000130.tif37147 Examples of the group represented by formula (L1-2) include the divalent groups shown below. TIFF2023156259000131.tif23130 Examples of the group represented by formula (L1-3) include the divalent groups shown below. TIFF2023156259000132.tif16147 Examples of the group represented by formula (L1-4) include the divalent groups shown below. TIFF2023156259000133.tif13168L 55 is preferably a single bond or a group represented by formula (L1-1).

[0193] The structural unit (a5-1) includes the structural units shown below and R in the structural unit (a5-1) in the structural units shown below. 51 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. When the resin (A) contains the structural unit (a5), the content thereof is preferably 1 to 30 mol %, more preferably 2 to 20 mol %, and even more preferably 3 to 15 mol %, based on all structural units in the resin (A).

[0194] <Structural unit (a6)> The structural unit (a6) is a structural unit having an -SO2- group, and preferably has an -SO2- group in a side chain. The 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 or polycyclic structure) having an -SO2- group. A structural unit having a cyclic structure having an -SO2- group is preferred, and a structural unit having a cyclic structure containing an -SO2-O- group (sultone ring) is more preferred.

[0195] The sultone ring may be a ring having the following formula (T 1 -1), formula (T 1 -2), formula (T 1 -3) and the formula (T 1 The bonding site can be any position. The sultone ring may be monocyclic, but is preferably polycyclic. A polycyclic sultone ring refers to a bridged ring containing -SO2-O- as an atomic group constituting the ring, and is represented by the formula (T 1 -1) and the formula (T 1 The sultone ring is represented by the formula (T 1 As in the ring represented by formula (2), the atomic group constituting the ring may further contain a heteroatom in addition to —SO—O—. Examples of the heteroatom include an oxygen atom, a sulfur atom, and a nitrogen atom, and an oxygen atom is preferred. TIFF2023156259000135.tif3285

[0196] The sultone ring may have a substituent, and examples of the substituent include an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, and an alkylcarbonyl group having 2 to 4 carbon atoms.

[0197] Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, and a decyl group, and preferably an alkyl group having 1 to 6 carbon atoms, and more preferably a methyl group. Examples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group, and preferably a trifluoromethyl group. Examples of the alkyl group having a hydroxy group include a hydroxymethyl group and a 2-hydroxyethyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a p-methylphenyl group, a p-tert-butylphenyl group, a p-adamantylphenyl group, a tolyl group, a xylyl group, a cumyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group. Aralkyl groups include benzyl, phenethyl, phenylpropyl, naphthylmethyl, and naphthylethyl groups. Examples of the alkoxycarbonyl group include groups in which an alkoxy group, such as a methoxycarbonyl group or an ethoxycarbonyl group, is bonded to a carbonyl group, and preferred are alkoxycarbonyl groups having 6 or less carbon atoms, more preferably a methoxycarbonyl group. Alkylcarbonyl groups include acetyl, propionyl and butyryl groups.

[0198] From the viewpoint of ease of production of the monomer from which the structural unit (a6) is derived, a sultone ring having no substituent is preferred. The sultone ring is preferably a ring represented by the following formula (T1'). TIFF2023156259000136.tif3271[In formula (T1'), X 11 represents an oxygen atom, a sulfur atom or a methylene group. R 41 represents an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, or an alkylcarbonyl group having 2 to 4 carbon atoms. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41 may be the same or different. The binding site is at any position.] X 11 is preferably an oxygen atom or a methylene group, more preferably a methylene group. R 41 Examples of the substituent include the same as the substituent on the sultone ring, and an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group is preferred. ma is preferably 0 or 1, and more preferably 0.

[0199] Examples of the ring represented by formula (T1') include the following rings: The binding site is at any position. Among these, the binding site is preferably the 1st or 3rd position. TIFF2023156259000137.tif47148

[0200] The structural unit having an -SO2- group preferably further has a group derived from a polymerizable group, such as a vinyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, an acryloylthio group, or a methacryloylthio group. Among these, the monomer from which the structural unit (a6) is derived is preferably a monomer having an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer.

[0201] The structural unit (a6) is preferably a structural unit represented by the formula (a6-0). TIFF2023156259000138.tif4863[In formula (a6-0), R x represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom. A xx is an oxygen atom, -N(R c )- or a sulfur atom. A x represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group is not -O-, -CO- or -N(R d )- may be replaced. X 11 , R 41 and ma have the same meanings as above. R c and R d each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0202] R x Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R x Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group, and are preferably alkyl groups having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. R xExamples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group. R x is preferably 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.

[0203] A x Examples of the divalent saturated hydrocarbon group include a linear alkanediyl group, a branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and may be a combination of two or more of these groups. 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 a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, a heptadecane-1,17-diyl group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group; branched alkanediyl groups such as butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl; monocyclic divalent alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, such as 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 bonding position of to the sultone ring can be any position, but the 1-position is preferred.

[0204] Examples of the structural unit (a6-0) include the following structural units. TIFF2023156259000139.tif93150

[0205] Of these, structural units represented by formula (a6-1), formula (a6-2), formula (a6-6), formula (a6-7), formula (a6-8), and formula (a6-12) are preferred, and structural units represented by formula (a6-1), formula (a6-2), formula (a6-7), and formula (a6-8) are more preferred. When the resin (A) contains the structural unit (a6), the content thereof is preferably 1 to 50 mol %, more preferably 2 to 40 mol %, and even more preferably 3 to 30 mol %, based on all structural units in the resin (A).

[0206] <Structural unit (II)> The resin (A) may further contain a structural unit that decomposes upon exposure to generate an acid (hereinafter, sometimes referred to as "structural unit (II)"). Specific examples of the structural unit (II) include the structural units described in JP-A-2016-79235, and the structural unit (II) is preferably a structural unit having a sulfonate group or carboxylate group and an organic cation in a side chain, or a structural unit having a sulfonio group and an organic anion in a side chain.

[0207] The structural unit having a sulfonate group or carboxylate group and an organic cation on the side chain is preferably a structural unit represented by formula (II-2-A'). TIFF2023156259000140.tif35104[In formula (II-2-A'), X III3represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, wherein one -CH2- contained in the saturated hydrocarbon group may be replaced by -O-, -S-, or -CO-, and a hydrogen atom contained in the saturated hydrocarbon group may be replaced by a halogen atom, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, or a hydroxy group. A x1 represents an alkanediyl group having 1 to 8 carbon atoms, and a hydrogen atom contained in the alkanediyl group may be substituted with a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. RA - represents a sulfonate group or a carboxylate group. R III3 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. ZA + represents an organic cation.

[0208] R III3 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R III3 The alkyl group having 1 to 6 carbon atoms which may have a halogen atom and is represented by the formula: a8 Examples of the alkyl group include the same alkyl groups having 1 to 6 carbon atoms which may have a halogen atom and which are represented by the following formula: A x1 Examples of the alkanediyl group having 1 to 8 carbon atoms represented by the formula (I) include a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. A X1Examples of the optionally substituted perfluoroalkyl group having 1 to 6 carbon atoms include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, and a perfluorohexyl group. X III3 Examples of the divalent saturated hydrocarbon group having 1 to 18 carbon atoms represented by the formula (I) include a linear or branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and these may be used in combination. Specific examples thereof include linear alkanediyl groups such as 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, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl; butane-1,3-diyl, 2-methylpropane-1,3-diyl, and 2-methylpropane-1,3-diyl; Examples include branched alkanediyl groups such as pentane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl; cycloalkanediyl groups such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; and divalent polycyclic alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, and adamantane-2,6-diyl. Examples of saturated hydrocarbon groups in which -CH2- is replaced with -O-, -S-, or -CO- include divalent groups represented by formulae (X1) to (X53). However, the number of carbon atoms before the -CH2- in the saturated hydrocarbon group is replaced with -O-, -S-, or -CO- is 17 or less. In the following formulae, * and ** represent bonding sites, and * represents A x1 represents the binding site with JPEG2023156259000141.jpg145161

[0209] X 3 represents a divalent saturated hydrocarbon group having 1 to 16 carbon atoms. X 4 represents a divalent saturated hydrocarbon group having 1 to 15 carbon atoms. X 5 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms. X 6 represents a divalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 7 represents a trivalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 8 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.

[0210] ZA in formula (II-2-A') + is the cation Z1 in the salt represented by formula (B1) + The same can be mentioned.

[0211] The structural unit represented by formula (II-2-A') is preferably a structural unit represented by formula (II-2-A). TIFF2023156259000142.tif38109 [In formula (II-2-A), R III3 , X III3 and ZA + has the same meaning as above. z2A represents an integer of 0 to 6. R III2 and R III4 each independently represents a hydrogen atom, a fluorine atom, or a perfluoroalkyl group having 1 to 6 carbon atoms; when z2A is 2 or more, a plurality of R III2 and R III4 may be the same as or different from each other. Q a and Q b each independently represents a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms.] R III2 , R III4 , Q a and Q bAs the perfluoroalkyl group having 1 to 6 carbon atoms represented by the formula, the above-mentioned Q b1 Examples include the same perfluoroalkyl groups having 1 to 6 carbon atoms as those represented by the following formula:

[0212] The structural unit represented by formula (II-2-A) is preferably a structural unit represented by formula (II-2-A-1). TIFF2023156259000143.tif5577 [In formula (II-2-A-1), R III2 , R III3 , R III4 , Q a , Q b and ZA + has the same meaning as above. R III5 represents a saturated hydrocarbon group having 1 to 12 carbon atoms. z2A1 represents an integer of 0 to 6. X I2 represents a divalent saturated hydrocarbon group having 1 to 11 carbon atoms, wherein -CH2- contained in the saturated hydrocarbon group may be replaced by -O-, -S-, or -CO-, and wherein a hydrogen atom contained in the saturated hydrocarbon group may be substituted by a halogen atom or a hydroxy group. R III5 Examples of the saturated hydrocarbon group having 1 to 12 carbon atoms represented by the formula (I) include linear or branched alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. X I2 As the divalent saturated hydrocarbon group represented by X III3 Examples of the divalent saturated hydrocarbon group include those similar to those represented by the following formula:

[0213] As the structural unit represented by formula (II-2-A-1), a structural unit represented by formula (II-2-A-2) is more preferred. TIFF2023156259000144.tif5287 [In formula (II-2-A-2), R III3 , RIII5 and ZA + has the same meaning as above. m and nA each independently represent 1 or 2.

[0214] Examples of the structural unit represented by formula (II-2-A') include the following structural units, R III3 Examples of such a structural unit include a structural unit in which the group corresponding to the methyl group in the formula (1) is replaced with a hydrogen atom, a halogen atom (e.g., a fluorine atom), or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (e.g., a trifluoromethyl group), and the structural units described in WO 2012 / 050015. + represents an organic cation. TIFF2023156259000145.tif86163

[0215] The structural unit having a sulfonio group and an organic anion on the side chain is preferably a structural unit represented by formula (II-1-1). TIFF2023156259000146.tif3791 [In formula (II-1-1), A II1 represents a single bond or a divalent linking group. R II1 represents a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms. R II2 and R II3 each independently represents a hydrocarbon group having 1 to 18 carbon atoms; R II2 and R II3 may be bonded to each other to form a ring together with the sulfur atom to which they are attached. R II4 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. A - represents an organic anion. R II1 Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula include a phenylene group and a naphthylene group. R II2 and R II3Examples of the hydrocarbon group represented by the formula (I) include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. Examples of the alkyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and group formed by combining these groups include the same as those described above. R II4 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R II4 The alkyl group having 1 to 6 carbon atoms which may have a halogen atom and is represented by the formula: a8 Examples of the alkyl group include the same alkyl groups having 1 to 6 carbon atoms which may have a halogen atom and which are represented by the following formula: A II1 Examples of the divalent linking group represented by the formula (I) include a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O-, -S- or -CO-. III3 Examples include the same divalent saturated hydrocarbon groups having 1 to 18 carbon atoms as those represented by the following formula:

[0216] The structural unit containing a cation in formula (II-1-1) includes the structural unit represented by the following formula and R II4 Examples of structural units include those in which a group corresponding to the methyl group in the above formula (I) is replaced with a hydrogen atom, a halogen atom (for example, a fluorine atom), or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (for example, a trifluoromethyl group). TIFF2023156259000147.tif72163

[0217] A - Examples of the organic anion represented by the formula (A) include a sulfonate anion, a sulfonylimide anion, a sulfonylmethide anion, and a carboxylate anion. -The organic anion represented by formula (I) is preferably a sulfonate anion, and the sulfonate anion is more preferably an anion contained in the salt represented by formula (B1). The sulfonylimide anion and sulfonylmethide anion are the anions AI contained in the salt represented by formula (I). - The carboxylate anion is more preferably: The carboxylate anion may be: JPEG2023156259000148.jpg43155

[0218] Examples of the structural unit represented by formula (II-1-1) include structural units represented by the following formulas. JPEG2023156259000149.jpg88149

[0219] When the structural unit (II) is contained in the resin (A), the content of the structural unit (II) is preferably 1 to 20 mol %, more preferably 2 to 15 mol %, and even more preferably 3 to 10 mol %, based on the total structural units of the resin (A).

[0220] The resin (A) may contain structural units other than the above-mentioned structural units, and examples of such structural units include structural units well known in the art.

[0221] The resin (A) is preferably a resin composed of the structural unit (a1) and the structural unit (s), that is, a copolymer of the monomer (a1) and the monomer (s). The structural unit (a1) is preferably at least one selected from the group consisting of the structural unit (a1-0), the structural unit (a1-1), and the structural unit (a1-2) (preferably the structural unit having a cyclohexyl group or a cyclopentyl group), more preferably at least two selected from the group consisting of the structural unit (a1-1) and the structural unit (a1-2). The structural unit (s) is preferably at least one selected from the group consisting of the structural unit (a2) and the structural unit (a3). The structural unit (a2) is preferably the structural unit (a2-1) or the structural unit (a2-A). The structural unit (a3) ​​is preferably at least one selected from the group consisting of the structural unit represented by formula (a3-1), the structural unit represented by formula (a3-2), and the structural unit represented by formula (a3-4). The structural units constituting the resin (A) may be used singly or in combination of two or more, and can be produced by a known polymerization method (e.g., radical polymerization) using monomers that lead to these structural units. The content of each structural unit in the resin (A) can be adjusted by the amount of monomer used in the polymerization. The weight average molecular weight of the 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 a value determined by gel permeation chromatography under the conditions described in the Examples.

[0222] <Resins other than Resin (A)> The resist composition of the present invention may contain a resin other than the resin (A) in combination. Examples of resins other than resin (A) include resins containing the structural unit (a4) or the structural unit (a5) (hereinafter, sometimes referred to as resin (X)). As the resin (X), a resin containing the structural unit (a4) is particularly preferred. Examples of structural units that the resin (X) may further have include the structural unit (a1), the structural unit (a2), the structural unit (a3), and structural units derived from other known monomers. Of these, the resin (X) is preferably a resin consisting only of the structural unit (a4) and / or the structural unit (a5). When resin (X) contains structural unit (a4), the content of structural unit (a4) in resin (X) is, based on the total of all structural units in resin (X), 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more. Also, it may be 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 may be 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) in resin (X) is, based on the total of all structural units in resin (X), 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more. Further, it may be 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. Specific examples include 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%. Furthermore, when the resin (X) contains the structural unit (a4) and the structural unit (a5), the total content of the structural unit (a4) and the structural unit (a5) relative to the total of all structural units in the resin (X) may be 40 mol% or more, preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more. Further, it may be 100 mol% or less. Specific examples include 40 to 100 mol%, preferably 60 to 100 mol%, more preferably 70 to 100 mol%, and even more preferably 80 to 100 mol%. The structural units constituting the resin (X) may be used singly or in combination of two or more, and can be produced by a known polymerization method (e.g., radical polymerization) using monomers that derive these structural units. The content of each structural unit in the resin (X) can be adjusted by the amount of monomer used in the 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 method for measuring the weight average molecular weight of resin (X) is the same as that for resin (A).

[0223] When the resist composition of the present invention contains resin (X), the content thereof 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, still more preferably 1 to 30 parts by mass, and even more preferably 1 to 8 parts by mass, relative to 100 parts by mass of resin (A).

[0224] The content of resin (A) in the resist composition is preferably 80% to 99% by mass, and more preferably 90% to 99% by mass, based on the solid content of the resist composition. Furthermore, when a resin other than resin (A) is contained, the total content of resin (A) and the resin other than resin (A) is preferably 80% to 99% by mass, and more preferably 90% to 99% by mass, based on the solid content of the resist composition. In this specification, the "solid content of the resist composition" refers to the sum of all components in the resist composition excluding the solvent (E), which will be described later. The solid content of the resist composition and the resin content relative to the solid content can be measured using known analytical methods such as liquid chromatography or gas chromatography.

[0225] <Solvent (E)> The content of the solvent (E) in the resist composition is usually from 90 to 99.9% by mass, preferably from 92 to 99% by mass, and more preferably from 94 to 99% by mass. The content of the solvent (E) can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0226] Examples of the 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; cyclic esters such as γ-butyrolactone; etc. One type of solvent (E) may be used alone, or two or more types may be used.

[0227] <Quencher (C)> Examples of the quencher (C) include salts that generate acids that are weaker in acidity than the acids generated from the salts used in the basic nitrogen-containing organic compounds and acid generators (such as salt (I) and salt (B1)). When the resist composition contains the quencher (C), the content of the quencher (C) is preferably about 0.01 to 15 mass%, more preferably about 0.01 to 10 mass%, even more preferably about 0.1 to 8 mass%, and even more preferably about 0.1 to 7 mass%, based on the solids content of the resist composition. The basic nitrogen-containing organic compound includes amines and ammonium salts. The amines include aliphatic amines and aromatic amines. The aliphatic amines include primary amines, secondary amines, and tertiary amines.

[0228] 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, tributaryamine, benzophenone ... ethylamine, 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-pyridinyl)-2-methylpropanol, 2,2 ... 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, 2,2'-methylenebisaniline, Examples thereof include 1,2-di(4-pyridyl)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, and bipyridine, preferably diisopropylaniline, and more preferably 2,6-diisopropylaniline.

[0229] 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.

[0230] The acidity of a salt that generates an acid with a lower acidity than the acid generated from the acid generator is indicated 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 salts represented by the following formula, salts represented by formula (D) described in JP-A-2015-147926 (hereinafter sometimes referred to as "weak acid inner salt (D)"), and salts described in JP-A-2012-229206, JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-39502, and JP-A-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 even more preferably a diphenyliodonium salt containing a phenyl group substituted with a carboxylic acid anion among the weak acid inner salts (D). TIFF2023156259000150.tif97153

[0231] 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 for at least one of the two phenyl groups bonded to the iodonium cation, and specifically includes salts represented by the following formula.

[0232] TIFF2023156259000151.tif2362[In formula (D), R D1 and R D2 each 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 of 0 to 4, and when m' is 2 or more, a plurality of R D1 may be the same or different, and when n' is 2 or more, a plurality of R D2 may be the same or different.] R D1 and R D2 Examples of the hydrocarbon group include a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. Examples of the chain hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, and nonyl groups. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and may be either saturated or unsaturated. Examples of the alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclononyl, and cyclododecyl, norbornyl, and adamantyl. Examples of aromatic hydrocarbon groups include aryl groups such as a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a 4-propylphenyl group, a 4-isopropylphenyl group, a 4-butylphenyl group, a 4-t-butylphenyl group, a 4-hexylphenyl group, a 4-cyclohexylphenyl group, an anthryl group, a p-adamantylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group. Examples of groups formed by combining these groups include alkyl-cycloalkyl groups, cycloalkyl-alkyl groups, and aralkyl groups (e.g., 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, and 6-phenyl-1-hexyl group). Examples of the alkoxy group include a methoxy group and an ethoxy group. Examples of the acyl group include an acetyl group, a propanoyl group, a benzoyl group, and a cyclohexanecarbonyl group. Examples of the acyloxy group include groups in which an oxy group (—O—) is bonded to the above-mentioned acyl group. Examples of the alkoxycarbonyl group include a group in which a carbonyl group (—CO—) is bonded to the above alkoxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. R D1 and R D2 are each independently 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 preferably an integer of 0 to 2, more preferably 0. When m' is 2 or more, multiple R D1 may be the same or different, and when n' is 2 or more, a plurality of R D2 may be the same or different.

[0233] More specifically, the following salts are included: TIFF2023156259000152.tif72165

[0234] <Other ingredients> The resist composition of the present invention may optionally contain components other than those described above (hereinafter, these may be referred to as "other components (F)"). There are no particular limitations on the other components (F), and additives known in the resist field, such as sensitizers, dissolution inhibitors, surfactants, stabilizers, and dyes, can be used.

[0235] <Preparation of Resist Composition> The resist composition of the present invention can be prepared by mixing the salt (I), and, if necessary, the resin (A), the acid generator (B), a resin other than the resin (A), the solvent (E), the quencher (C), and other components (F). The order of mixing is arbitrary and is not particularly limited. The temperature during mixing can be selected from 10 to 40°C, depending on the type of resin, the solubility of the resin in the solvent (E), and other factors. The mixing time can be selected from 0.5 to 24 hours, depending on the mixing temperature. The mixing method is also not particularly limited, and stirring and mixing can be used. After mixing the components, it is preferable to filter the mixture using a filter with a pore size of about 0.003 to 0.2 μm.

[0236] <Method for producing a resist pattern> The method for producing a resist pattern of the present invention comprises the steps of: (1) applying the resist composition of the present invention onto a substrate; (2) drying the applied composition to form a composition layer; (3) exposing the composition layer to light; (4) heating the composition layer after exposure; and (5) A step of developing the composition layer after heating is included. The resist composition can be applied to a substrate using a commonly used device such as a spin coater. Examples of the substrate include inorganic substrates such as silicon wafers, and organic substrates having a resist film or the like formed on their surfaces. Before applying the resist composition, the substrate may be cleaned, and an anti-reflective film or the like may be formed on the substrate. The composition after coating is dried to remove the solvent and form a composition layer. Drying is carried out, 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 during vacuum drying is preferably 1 to 1.0 x 10 5 It is preferable that the pressure is about Pa. The resulting composition layer is typically exposed using an exposure machine. The exposure machine may be an immersion exposure machine. Various exposure light sources can be used, including those that emit ultraviolet laser light such as KrF excimer laser (wavelength 248 nm), ArF excimer laser (wavelength 193 nm), and F2 excimer laser (wavelength 157 nm); those that convert the wavelength of laser light from a solid-state laser source (such as a YAG or semiconductor laser) to emit harmonic laser light in the far ultraviolet or vacuum ultraviolet range; and those that irradiate with electron beams or extreme ultraviolet light (EUV). In this specification, irradiation with these types of radiation may be collectively referred to as "exposure." During exposure, exposure is typically performed through a mask corresponding to the desired pattern. When the exposure light source is an electron beam, exposure may be performed by direct writing without using a mask. The composition layer after exposure is subjected to a heat treatment (so-called post-exposure bake) to promote the deprotection reaction of the acid labile groups. The heating temperature is usually about 50 to 200°C, preferably about 70 to 150°C. A chemical treatment (silylation) may be performed to adjust the hydrophilicity or hydrophobicity of the resin on the surface side of the heated composition. Furthermore, before development, the steps of applying a resist composition, drying, exposing, and heating may be repeated on the composition layer after exposure. The heated composition layer is usually developed using a developer in a developing device. Development methods include dipping, puddling, spraying, and dynamic dispensing. 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 developer as follows, a positive resist pattern or a negative resist pattern can be produced. When a positive resist pattern is produced from the resist composition of the present invention, an alkaline developer is used as the developer. The alkaline developer may be any of various alkaline aqueous solutions used in this field. Examples include aqueous solutions of tetramethylammonium hydroxide and (2-hydroxyethyl)trimethylammonium hydroxide (commonly known as choline). The alkaline developer may also contain a surfactant. After development, the resist pattern is preferably washed with ultrapure water, and then water remaining on the substrate and pattern is removed. When a negative resist pattern is produced from the resist composition of the present invention, a developer containing an organic solvent (hereinafter sometimes referred to as an "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. The content of the organic solvent in the organic developer 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 only the organic solvent. Among these, the organic developer is preferably a developer containing butyl acetate and / or 2-heptanone. 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 only butyl acetate and / or 2-heptanone. The organic developer may contain a surfactant and a small amount of water. During development, development may be stopped by replacing the organic developer with a different type of solvent. The developed resist pattern is preferably washed with a rinse solution. There are no particular limitations on the rinse solution 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 the rinse liquid remaining on the substrate and the pattern.

[0237] <Application> The resist composition of the present invention is suitable as a resist composition for KrF excimer laser exposure, a resist composition for ArF excimer laser exposure, a resist composition for electron beam (EB) exposure, or a resist composition for EUV exposure, and is particularly suitable as a resist composition for ArF excimer laser exposure, and is useful for semiconductor microfabrication. [Example]

[0238] The present invention will be explained in more detail with reference to examples. In the examples, "%" and "parts" representing the content or amount used are by mass unless otherwise specified. The weight-average molecular weight is a value determined by gel permeation chromatography under the following analytical conditions: Column: TSKgel Multipore HXL-M x 3 + guard column (Tosoh Corporation) Eluent: tetrahydrofuran Flow rate: 1.0mL / min Detector: RI detector Column temperature: 40℃ Injection volume: 100μl Molecular weight standard: Standard polystyrene (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 by "MASS."

[0239] Example 1: Synthesis of salt represented by formula (I-8) 2.78 parts of a compound represented by formula (I-8-a) and 30 parts of dimethylformamide were mixed and stirred at 23 ° C. for 30 minutes. The resulting mixture was cooled to 0 ° C., and then 0.30 parts of sodium hydride was added and stirred at 0 ° C. for 4 hours. 3.15 parts of a salt represented by formula (I-8-b) were added to the resulting mixture at 0 ° C., and the mixture was stirred at 0 ° C. for 3 hours to obtain a mixture containing a salt represented by formula (I-8-c). The resulting mixture was heated to 23 ° C., and 11 parts of a 5% aqueous oxalic acid solution was added and stirred at 23 ° C. for 30 minutes. 6.41 parts of a salt represented by formula (I-8-d) were then added and stirred at 23 ° C. for 7 hours. 100 parts of chloroform and 30 parts of ion-exchanged water were added to the resulting reaction mixture, and the mixture was stirred at 23 ° C. for 30 minutes, after which the organic layer was separated and separated. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to separate the organic layer. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the concentrated residue. The mixture was stirred at 23°C for 30 minutes, after which the supernatant was removed and the mixture was concentrated to obtain 1.61 parts of the salt represented by formula (I-8). MASS(ESI(+)Spectrum):M + 537.1 MASS(ESI(-)Spectrum):M - 517.1

[0240] Example 2: Synthesis of salt represented by formula (I-3614) 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. The resulting mixture was cooled to 0°C, and then 0.30 parts of sodium hydride was added and stirred at 0°C for 4 hours. 3.15 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). The resulting mixture was heated to 23°C, and 11 parts of a 5% aqueous oxalic acid solution was added and stirred at 23°C for 30 minutes. 4.72 parts of the salt represented by formula (I-42-d) were then added and stirred at 23°C for 7 hours. 100 parts of chloroform and 30 parts of ion-exchanged water were added to the resulting reaction mixture, and the mixture was stirred at 23°C for 30 minutes, followed by separation and the organic layer was extracted. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to separate the organic layer. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the concentrated residue. The mixture was stirred at 23°C for 30 minutes, after which the supernatant was removed and the mixture was concentrated to obtain 1.02 parts of the salt represented by formula (I-3614). MASS(ESI(+)Spectrum):M + 537.1 MASS(ESI(-)Spectrum):M - 349.0

[0241] Example 3: Synthesis of salt represented by formula (I-46) 2.92 parts of a compound represented by formula (I-46-a) and 30 parts of dimethylformamide were mixed and stirred at 23 ° C. for 30 minutes. The resulting mixture was cooled to 0 ° C., and then 0.30 parts of sodium hydride was added and stirred at 0 ° C. for 4 hours. 3.15 parts of a salt represented by formula (I-8-b) were added to the resulting mixture at 0 ° C., and the mixture was stirred at 0 ° C. for 3 hours to obtain a mixture containing a salt represented by formula (I-8-c). The resulting mixture was heated to 23 ° C., and 11 parts of a 5% aqueous oxalic acid solution was added and the mixture was stirred at 23 ° C. for 30 minutes. 6.41 parts of a salt represented by formula (I-8-d) was then added and the mixture was stirred at 23 ° C. for 7 hours. 100 parts of chloroform and 30 parts of ion-exchanged water were added to the resulting reaction mixture, and the mixture was stirred at 23 ° C. for 30 minutes, after which the organic layer was separated and separated. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to separate the organic layer. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the concentrated residue. The mixture was stirred at 23°C for 30 minutes, after which the supernatant was removed and the mixture was concentrated to obtain 2.43 parts of the salt represented by formula (I-46). MASS(ESI(+)Spectrum):M + 551.1 MASS(ESI(-)Spectrum):M - 517.1

[0242] Example 4: Synthesis of salt represented by formula (I-122) TIFF2023156259000156.tif86156 3.13 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, after which 0.69 parts of potassium carbonate and 0.22 parts of potassium iodide were added and the mixture was heated to 75 ° C. To the resulting mixture, 3.55 parts of the compound represented by formula (I-122-b) were added, stirred at 75 ° C. for 5 hours, and then cooled to 23 ° C. After heating the resulting mixture to 23 ° C., 11 parts of a 5% aqueous oxalic acid solution was added and stirred at 23 ° C. for 30 minutes, after which 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 mixture, 100 parts of chloroform and 30 parts of ion-exchanged water were added, stirred at 23 ° C. for 30 minutes, and then the organic layer was separated and separated. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to separate the organic layer. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the concentrated residue. The mixture was stirred at 23°C for 30 minutes, after which the supernatant was removed and the mixture was concentrated to obtain 6.72 parts of the salt represented by formula (I-122). MASS(ESI(+)Spectrum):M + 595.1 MASS(ESI(-)Spectrum):M - 517.1

[0243] Example 5: Synthesis of salt represented by formula (I-3626) 3.13 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, after which 0.69 parts of potassium carbonate and 0.22 parts of potassium iodide were added and the mixture was heated to 75 ° C. 3.55 parts of the compound represented by formula (I-122-b) were added to the resulting mixture, stirred at 75 ° C. for 5 hours, and then cooled to 23 ° C. The resulting mixture was heated to 23 ° C., and 11 parts of a 5% aqueous oxalic acid solution was added and stirred at 23 ° C. for 30 minutes, after which 4.72 parts of the salt represented by formula (I-42-d) were added and stirred at 23 ° C. for 7 hours. 100 parts of chloroform and 30 parts of ion-exchanged water were added to the resulting reaction mixture, stirred at 23 ° C. for 30 minutes, and then the organic layer was separated and separated. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to separate the organic layer. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the concentrated residue. The mixture was stirred at 23°C for 30 minutes, after which the supernatant was removed and the mixture was concentrated to obtain 5.21 parts of the salt represented by formula (I-3626). MASS(ESI(+)Spectrum):M + 595.1 MASS(ESI(-)Spectrum):M - 349.0

[0244] Example 6: Synthesis of salt represented by formula (I-274) TIFF2023156259000158.tif95162 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. The resulting mixture was cooled to 0 ° C., and then 0.30 parts of sodium hydride was added and stirred at 0 ° C. for 4 hours. 3.15 parts of a salt represented by formula (I-8-b) were added to the resulting mixture at 0 ° C., and the mixture was stirred at 0 ° C. for 3 hours to obtain a mixture containing a salt represented by formula (I-274-c). The resulting mixture was heated to 23 ° C., and 11 parts of a 5% aqueous oxalic acid solution was added and the mixture was stirred at 23 ° C. for 30 minutes. 6.41 parts of a salt represented by formula (I-8-d) was then added and the mixture was stirred at 23 ° C. for 7 hours. 100 parts of chloroform and 30 parts of ion-exchanged water were added to the resulting reaction mixture, and the mixture was stirred at 23 ° C. for 30 minutes, after which the organic layer was separated and separated. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to separate the organic layer. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the concentrated residue. The mixture was stirred at 23°C for 30 minutes, after which the supernatant was removed and the mixture was concentrated to obtain 5.39 parts of the salt represented by formula (I-274). MASS(ESI(+)Spectrum):M + 677.0 MASS(ESI(-)Spectrum):M - 517.1

[0245] Example 7: Synthesis of salt represented by formula (I-282) TIFF2023156259000159.tif96166 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. The resulting mixture was cooled to 0 ° C., and then 0.30 parts of sodium hydride was added and stirred at 0 ° C. for 4 hours. 3.15 parts of a salt represented by formula (I-8-b) were added to the resulting mixture at 0 ° C., and the mixture was stirred at 0 ° C. for 3 hours to obtain a mixture containing a salt represented by formula (I-274-c). The resulting mixture was heated to 23 ° C., and 11 parts of a 5% aqueous oxalic acid solution was added and the mixture was stirred at 23 ° C. for 30 minutes. 5.70 parts of a salt represented by formula (I-16-d) was then added and the mixture was stirred at 23 ° C. for 7 hours. 100 parts of chloroform and 30 parts of ion-exchanged water were added to the resulting reaction mixture, and the mixture was stirred at 23 ° C. for 30 minutes, after which the organic layer was separated and separated. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to separate the organic layer. This wat...

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 0 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 4, 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 4, 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 5, 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 4, 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 4, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 0≦m1+m7≦5, 0≦m2+m8≦4, 0≦m3+m9≦4, and at least one of m1, m2, and m3 represents an integer of 1 or more. X ７ is a single bond, -CH 2 -, -O-, -S-, -CO-, -SO- or -SO ２ Represents -. 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 0 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 4, 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 4, and when m3 is 2 or more, the groups in the parentheses may be the same or different. stomach. 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 good. m5 represents an integer of 0 to 13, and when m5 is 2 or more, a plurality of R ５ are the same but different Good too. m6 represents an integer of 0 to 13, and when m6 is 2 or more, a plurality of R ６ are the same but different That's fine. m7 represents an integer of 0 to 5, and when m7 is 2 or more, a plurality of R ７ are the same but different It is also possible. m8 represents an integer of 0 to 4, and when m8 is 2 or more, a plurality of R ８ are the same but different It may be so. m9 represents an integer of 0 to 4, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 0≦m1+m7≦5, 0≦m2+m8≦4, 0≦m3+m9≦4, and at least one of m1, m2, and m3 represents an integer of 1 or more. X ７ is a single bond, -CH 2 -, -O-, -S-, -CO-, -SO- or -SO ２ Represents -. AI － is an organic aniline Indicates on.]

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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