Resist composition and method for producing resist pattern

Abstract

To provide a resist composition from which a resist pattern having good LER can be produced.SOLUTION: The resist composition contains: a carboxylic acid generator containing a carboxylate represented by formula (IA) or formula (IB); an acid generator other than the carboxylic acid generator; and a resin containing a structural unit having an acid-labile group and a structural unit represented by formula (a2-A).SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a resist composition and a method for producing a resist pattern.

Background Art

[0002] Patent Document 1 describes a salt represented by the following formula and a resist composition containing the salt as an acid generator. Composition is described. TIFF2025108538000001.tif30104 Patent Document 2 describes a resist composition containing a carboxylate represented by the following formula as a carboxylic acid generator. Composition is described. TIFF2025108538000002.tif2641 Patent Document 3 describes a resist composition containing a carboxylate represented by the following formula as a carboxylic acid generator. Composition is described. TIFF2025108538000003.tif2643

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0004] The present invention provides a salt capable of producing a resist pattern with better line edge roughness (LER) than a resist pattern formed from a resist composition containing the above salt. To provide. For the purpose.

Means for Solving the Problems

[0005] The present invention includes the following inventions. [1] A carboxylate represented by formula (IA) or formula (IB). TIFF2025108538000004.tif69144[In formula (IA) and formula (IB), R 1 、R 2 、R 3 and R 4 each independently represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -C O- or -SO2-. R 1 and R 2 , and R 3 and R 4 may each be bonded to each other to form a ring having 3 to 24 carbon atoms together with the sulfur atom to which they are bonded, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO- . R 5 、R 6 、R 7 、R 8 and R 9 each independently represents a halogen atom, a hydroxy group, a perfluoroalkyl group having 1 to 6 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-. m5 represents any integer from 0 to 4, and when m5 is 2 or more, a plurality of R 5 may be the same or different from each other. m6 represents any integer from 0 to 4, and when m6 is 2 or more, a plurality of R 6 may be the same or different from each other. m7 represents any integer from 0 to 4, and when m7 is 2 or more, a plurality of R 7may be the same as or different from each other. It may be the same or different. m8 represents an integer from 0 to 4. When m8 is 2 or more, a plurality of R 8 may be the same as or different from each other. It may be the same or different. X 1 and X 2 each independently represents a single bond, an oxygen atom, a sulfur atom, or an alkanediyl group having 1 to 6 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced by -O- or -CO -. It may be replaced. X 01 、X 02 and X 03 each independently represents a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO - or -SO2-. [1] The carboxylate salt according to [1], wherein R [2] R 1 、R 2 、R 3 and R 4 each independently represents a phenyl group which may have a substituent. carboxylate salt. [3] X 01 、X 02 and X 03 each independently represents an aliphatic hydrocarbon group having 1 to 72 carbon atoms which may have a substituent (provided that -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O -, -S-, -CO- or -SO2-), or an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent. carboxylate salt according to [1] or [2]. [4] X 01 、X 02 and X 03 each independently represents an alicyclic hydrocarbon group which may have a fluorine atom or a hydroxy group (wherein -CH2- contained in the alicyclic hydrocarbon group is -O -or may be replaced by -CO-.), an alicyclic hydrocarbon group and a chain hydrocarbon group combined group (the -CH2- contained in the alicyclic hydrocarbon group and the chain hydrocarbon group is - O- or may be replaced by -CO-, and the alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom or a hydroxy group.). Or an aromatic hydrocarbon group which may have a fluorine atom or a hydroxy group, which is the carboxylic acid salt according to any one of [1] to [3]. [5] A carboxylic acid generator containing the carboxylate according to any one of [1] to [4]. [6] The resist composition according to [5], containing the carboxylic acid generator according to [5], an acid generator other than the carboxylic acid generator, and a resin having an acid unstable group. [7] The resin having an acid labile group contains at least one selected from the group consisting of a structural unit represented by the formula (a1-1) and a structural unit represented by the formula (a1- 2), which is the resist composition according to [6]. TIFF2025108538000005.tif46102 [In the formula (a1-1) and the formula (a1-2), L a1 and L a2 each independently represents -O- or *-O-(CH2) k1 -CO-O- represents, k1 represents an integer from 1 to 7, and * represents the bonding position with -CO-. R a4 and R a5 each independently represents a hydrogen atom or a methyl group. R a6 and R a7 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or a group combining these. m1 represents any integer from 0 to 14. n1 represents any integer from 0 to 10. n1' represents any integer from 0 to 3.] [8] The resin having an acid-labile group contains a structural unit represented by the formula (a2-A) [6] and is the resist composition described in [7]. TIFF2025108538000006.tif4459 [In the 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 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 represents a single bond or * -X a51 -(A a52 -X a52 ) nb - and * represents the bonding position to the carbon atom to which -R a50 is bonded. A a52 represents an alkanediyl group having 1 to 6 carbon atoms. X a51 and X a52 each independently represents -O-, -CO-O-, or -O-CO-. nb represents 0 or 1. mb represents any integer from 0 to 4. When mb is an integer of 2 or more, plural R may be the same as or different from each other.] a51 [9] (1) The step of applying the resist composition according to any one of [6] to [8] onto a substrate, (2) The step of drying the applied composition to form a composition layer, (3) The step of exposing the composition layer, (4) The step of heating the exposed composition layer, and A method for manufacturing a resist pattern, comprising the step of developing the composition layer after heating.

Advantages of the Invention

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

Modes for Carrying Out the Invention

[0007] In this specification, the “(meth)acrylic monomer” means “at least one of acrylic monomers and methacrylic monomers”. Expressions such as “(meth)acrylate” and “(meth)acrylic acid” also represent the same meaning. For the groups described in this specification, those that can take both a linear structure and a branched structure may be either of them. The “combined group” means a group formed by combining two or more of the exemplified groups with their valences appropriately changed. “Derived from” or “induced from” refers to the fact that the polymerizable C═C bond contained in the molecule becomes a —C—C— group by polymerization. When stereoisomers exist, all stereoisomers are included. For those that can take both a linear structure and a branched structure, either of them may be used. The “combined group” means a group formed by combining two or more of the exemplified groups with their valences appropriately changed. “Derived from” or “induced from” refers to the fact that the polymerizable C═C bond contained in the molecule becomes a —C—C— group by polymerization. When stereoisomers exist, all stereoisomers are included. In this specification, the “solid content of the resist composition” means the total of the components excluding the solvent (E) described later from the total amount of the resist composition.

[0008] <Carboxylate represented by formula (IA) or formula (IB)> The present invention relates to a carboxylate represented by formula (IA) (hereinafter sometimes referred to as “carboxylate (IA)”) and a salt represented by formula (IB) (hereinafter sometimes referred to as “carboxylate (IB)”). Of the carboxylate (IA) and the carboxylate (IB), the side having a negative charge is the “anion” ​​​​​​​​​​The side having a positive charge is referred to as "cation (IA)" or "cation (IB)". This may be the case. TIFF2025108538000007.tif69144 [In formula (IA) and formula (IB), all symbols have the same meanings as described above respectively.] Carboxylate (IA) and carboxylate (IB) can also be represented as follows. TIFF2025108538000008.tif84162 [In formula (IA) and formula (IB), all symbols have the same meanings as described above respectively.]

[0009] R 1 、R 2 、R 3 and R 4 Examples of the hydrocarbon group in include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkyl groups, alkenyl groups, alkynyl groups, and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, and groups formed by combining chain hydrocarbon groups such as alkyl groups, alkenyl groups, alkynyl groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, etc. R 1 、R 2 、R 3 and R 4 When the -CH2- contained in the hydrocarbon group in is replaced by -O-, -S -, -CO- or -SO2-, the carbon number before replacement is taken as the total carbon number of the hydrocarbon group. Examples of the alkyl group include 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 carbon number of the alkyl group is preferably 1 to 12, more preferably 1 to 9, still more preferably 1 to 6, and even more preferably 1 to 4. There is. Examples of the alkenyl group include ethenyl group, propenyl group, isopropenyl group, butenyl group, Isobutenyl group, tert-butenyl group, pentenyl group, hexenyl group, heptenyl group, Octynyl group, isooctynyl group, nonenyl group, etc. may be mentioned. Examples of the alkynyl group include ethynyl group, propynyl group, isopropynyl group, butynyl group, Isobutynyl group, tert-butynyl group, pentynyl group, hexynyl group, octynyl group, Nonynyl group and the like may be mentioned. When -CH2- contained in the chain hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2-, the total carbon number of the chain hydrocarbon group is the carbon number before replacement. For example, as a group in which -CH2- at any position contained in the alkyl group is replaced by -O- or -CO-, there are a hydroxy group (a group in which -CH2- at any position contained in the methyl group is replaced by -O -), a carboxy group (a group in which -CH2-CH2- at any position contained in the ethyl group is replaced by -O-CO -), an alkoxy group (a group in which -CH2- at any position contained in the alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -CO-O-), etc. may be mentioned. In addition, the replacement in the alkenyl group and alkynyl group may be any one containing a carbon-carbon double bond or a carbon-carbon triple bond at any position in the examples of the replacement in the above-mentioned alkyl group. Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyl A luoxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, noni A luoxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, etc. may be mentioned. The number of carbon atoms of the alkoxy group includes 1 to 11 carbon atoms, preferably 1 to 6, more Preferably 1 to 4. An alkoxycarbonyl group, an alkylcarbonyl group, and an alkylcarbonyloxy group are Groups in which a carbonyl group or a carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group are represented. Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, etc. Examples of the alkylcarbonyl group include an acetyl group , a propionyl group, a butyryl group, etc. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, etc. The number of carbon atoms of the alkoxy carbonyl group includes 2 to 11 carbon atoms, preferably 2 to 6, more Preferably 2 to 4. The number of carbon atoms of the alkylcarbonyl group includes 2 to 12 carbon atoms , preferably 2 to 6, more preferably 2 to 4. The number of carbon atoms of the alkylcarbonyloxy group includes 2 to 11 carbon atoms, preferably 2 to 6, more preferably 2 to 4. The alicyclic hydrocarbon group may be monocyclic, polycyclic or spiro ring, and may be either saturated or unsaturated . Examples of the alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cyclododecyl group, etc., and polycyclic cycloalkyl groups such as a norbornyl group, an adamantyl group, etc. are mentioned. Specifically, examples of the alicyclic hydrocarbon group include groups represented by formula (Y1) to formula (Y11), formula (Y36) to formula (Y38). Further, examples of the group in which -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -CO- or -SO2- include groups represented by formula (Y12) to formula (Y 35), formula (Y39) to formula (Y43). * represents a bonding site . . Among them, as the alicyclic hydrocarbon group, it is preferably a group represented by any one of formula (Y1) to formula (Y20), formula (Y26), formula ( Y27), formula (Y30), formula (Y31), formula (Y39) to formula (Y43), and more preferably a group represented by formula (Y3), (Y4), formula (Y9), formula (Y11), formula ( Y14), formula (Y15), formula (Y16), formula (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39), formula (Y40), formula (Y42) or formula (Y4 3). The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and still more preferably 3 to 12. Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group, fluorenyl group, etc. Phenyl group, naphthyl group

[0010] and anthryl group are preferred, phenyl group and naphthyl group are more preferred, and phenyl group is even more preferred. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and still more preferably 6 to 10. Examples of the combined group include .

[0011] As the combined group, A group combining an alicyclic hydrocarbon group and a chain hydrocarbon group (alkyl group, alkenyl group, and / or alkynyl group, etc.) (the -CH2- contained in the chain hydrocarbon group (alkyl group, alkenyl group, alkynyl group, etc.) and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-), A group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group (the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2- ), and A group combining an aromatic hydrocarbon group and a chain hydrocarbon group (alkyl group, alkenyl group, alkynyl group, etc.) (the -CH2- contained in the chain hydrocarbon group (alkyl group, alkenyl group, alkynyl group, etc.) may be replaced by -O-, -S-, -CO-, or -SO2- ). In the combination, the alicyclic hydrocarbon group, the chain hydrocarbon group (alkyl group, alken yl group, alkynyl group, etc.), and the aromatic hydrocarbon group may each be combined with two or more kinds. Also, in the above groups, groups with different valences (divalent or trivalent groups (chain hydrocarbon groups, alicyclic saturated hydrocarbon groups, aromatic hydrocarbon groups), etc.) may be included. Also, any of the groups may be bonded to a sulfur atom. Specific examples of the combined groups include Alicyclic hydrocarbon group-chain hydrocarbon group such as adamantylmethyl group, cyclohexylmethyl group-* (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, - S-, -CO-, or -SO2-), Chain hydrocarbon group-alicyclic hydrocarbon group such as methyladamantyl group-* (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO 2-), (which may be replaced by 2-), a chain hydrocarbon group - an aromatic hydrocarbon group - * (such as a tolyl group or a xylyl group, wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), (and may be so), a chain hydrocarbon group - an alicyclic hydrocarbon group - a chain hydrocarbon group - * (such as a methylcyclohexylmethyl group, wherein -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, - S-, -CO- or -SO2-), an aromatic hydrocarbon group - a chain hydrocarbon group - * (such as a benzyl group, wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), a chain hydrocarbon group - an aromatic hydrocarbon group - a chain hydrocarbon group - * (such as a tolylmethyl group, wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), (and may be so), an aromatic hydrocarbon group - an alicyclic hydrocarbon group - * (such as a phenyladamantyl group, wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), (and may be so), an alicyclic hydrocarbon group - an aromatic hydrocarbon group - * (such as a cyclohexylphenyl group or an adamantylphenyl group, wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO - or -SO2-), etc. may be mentioned. Here, * represents the bonding position with the sulfur atom.

[0012] R 1 、R 2 、R 3 and R 4 The substituents of the hydrocarbon groups include a halogen atom, a cyano A nor group, a perfluoroalkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-), etc. are exemplified. When the hydrocarbon group in R , R 1 , R 2 , R 3 and R 4 has a substituent, the total carbon number of the hydrocarbon group before substitution is defined as the total carbon number of the hydrocarbon group. Examples of the group in which -CH2- contained in the alkyl group is replaced by -O- or -CO- include a hydroxy group (a group in which -CH2- contained in the methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in the ethyl group is replaced by -O-CO-), an alkoxy group (a group in which -CH2- at any position contained in the alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -CO-O-), etc. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, and a perfluorohexyl group, etc. The carbon number of the perfluoroalkyl group is preferably When the hydrocarbon group in R , R , R and R has a substituent, the total carbon number of the hydrocarbon group before substitution is defined as the total carbon number of the hydrocarbon group. Examples of the group in which -CH2- contained in the alkyl group is replaced by -O- or -CO- include a hydroxy group (a group in which -CH2- contained in the methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in the ethyl group is replaced by -O-CO-), an alkoxy group (a group in which -CH2- at any position contained in the alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -CO-O-), etc. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

[0013] Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, and a perfluorohexyl group, etc. The carbon number of the perfluoroalkyl group is preferably Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, and a perfluorohexyl group, etc. The carbon number of the perfluoroalkyl group is preferably Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, and a perfluorohexyl group, etc. The carbon number of the perfluoroalkyl group is preferably Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, and a perfluorohexyl group, etc. The carbon number of the perfluoroalkyl group is preferably Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, and a perfluorohexyl group, etc. The carbon number of the perfluoroalkyl group is preferably is from 1 to 4, more preferably from 1 to 3. 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, an octyl group, a nonyl group, and the like. The number of carbon atoms of the alkyl group is preferably from 1 to 9, more preferably from 1 to 6, and even more preferably from 1 to 4. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pent yloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a non yloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, and the like. The number of carbon atoms of the alkoxy group is from 1 to 11, preferably from 1 to 6, more preferably from 1 to 4. The alkoxycarbonyl group, the alkylcarbonyl group, and the alkylcarbonyloxy group represent a group in which a carbonyl group or a carbonyloxy group is bonded to the above-described alkyl group or alkoxy group. Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, and the like. Examples of the alkylcarbonyl group include an acetyl group , a propionyl group, a butyryl group, and the like. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, and the like. The number of carbon atoms of the alkoxy carbonyl group is from 2 to 11, preferably from 2 to 6, and more preferably from 2 to 4. The number of carbon atoms of the alkylcarbonyl group is from 2 to 12, preferably from 2 to 6, and more preferably from 2 to 4. The number of carbon atoms of the alkylcarbonyloxy group is from 2 to 11, preferably from 2 to 6, and more preferably from 2 to 4.

[0014] R 1 、R 2 、R 3 and R 4 are each independently an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms or an aromatic hydrocarbon group which may have a substituent, or R 1 and R 2 , and R 3 and R 4 are bonded to each other to form a ring having 3 to 12 carbon atoms together with the sulfur atom to which they are bonded (—CH2— contained in the ring may be replaced by —O—, —S— or —CO—), preferably a methyl group, a cyclohexyl group or a phenyl group which may have a substituent, more preferably a phenyl group which may have a substituent, further preferably a phenyl group which may have a halogen atom, a perfluoroalkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms (—CH2— contained in the alkyl group may be replaced by —O— or —CO—) and may have a phenyl group which may have a substituent, still more preferably a phenyl group which may have a halogen atom, and even more preferably a phenyl group which may have a fluorine atom.

[0015] Examples of the perfluoroalkyl group having 1 to 6 carbon atoms of RR 5 、R 6 、R 7 、R 8 and R 9 include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoro isopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group and a perfluorohexyl group, etc. ​It is. The number of carbon atoms in the perfluoroalkyl group is preferably 1 to 4, more preferably 1 to 3. R 5 、R 6 、R 7 、R 8 and R 9 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 and other alkyl groups. 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 5 、R 6 、R 7 、R 8 and R 9 When -CH2- contained in the alkyl group in R 、R 、R 5 、R 6 、R 7 and R 8 is replaced by -O- or -CO-, the total number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkyl group -CO- replaced group), an alkoxy group (any -CH2-CH2 position in the alkyl group is replaced by -O-), an alkoxycarbonyl group (any position in the alkyl group is replaced by -O-CO-), an alkyl carbonyl group (any position in the alkyl group where -CH2- is replaced by -CO- replaced group), an alkylcarbonyloxy group (any position in the alkyl group where -C Groups in which H2-CH2- is replaced by -CO-O-, etc. may be mentioned. Specific examples thereof are the same as those described above. R 5 、R 6 、R 7 and R 8 are each independently preferably a halogen atom, a hydroxy group or an alkyl group having 1 to 12 carbon atoms, more preferably a fluorine atom, a hydroxy group or a methyl group, and even more preferably a fluorine atom or a hydroxy group. m5, m6, m7 and m8 are each independently preferably any integer from 0 to 2, and more preferably 0 or 1. R 9 is preferably a halogen atom, a hydroxy group or a perfluoroalkyl group having 1 to 6 carbon atoms, more preferably a halogen atom or a hydroxy group, and even more preferably a fluorine atom or a hydroxy group.

[0016] X 1 and X 2 as the C1-C6 alkanediyl group 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, a linear alkanediyl 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, a 2-methylbutane-1,4-diyl group and other branched alkanediyl groups. The carbon number of the alkanediyl group is preferably 1 to 4, and more preferably 1 to 3. X 1 and X 2 is each independently preferably a single bond, an oxygen atom, a sulfur atom, a methylene group or an eth ylene group, more preferably an oxygen atom or a sulfur atom, and even more preferably an oxygen atom . X 1 and X 2 may be bonded to the bonding position of I + at any of the ortho, meta and para positions with respect to the bonding position of I . Among them, it is preferably bonded to the para or meta position with respect to the bonding position of I + , and more preferably bonded to the para position.

[0017] Examples of the cation (IA) include the following cations. TIFF2025108538000010.tif205169

[0018] TIFF2025108538000011.tif140168

[0019] Examples of the cation (IB) include the following cations. TIFF2025108538000012.tif84153

[0020] TIFF2025108538000013.tif227166

[0021] In formula (I), the hydrocarbon group represented by X 01 , X 02 and X 03 includes aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkyl groups, alkenyl groups, alkynyl groups and alicyclic carbon hydrocarbon groups), aromatic hydrocarbon groups, and groups combining these. The -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2- . 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, an octyl group, a nonyl group, and the like. The number of carbon atoms in the alkyl group is preferably 1 to 18, more preferably 1 to 12, still more preferably 1 to 9, even more preferably 1 to 6, and even more preferably 1 to 4. Examples of the alkenyl group include an ethenyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octynyl group, an isooctynyl group, and a nonenyl group. 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. Examples of the group in which -CH2- contained in the chain hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- include a hydroxy group (a group in which -CH2- contained in the methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in the ethyl group is replaced by -O-CO-), an alkoxy group (a group in which -CH2- at any position contained in the alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -CO-O-), an alkylthio group (a group in which -CH2- at any position contained in the alkyl group is replaced by -S-), an alkylsulfinyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -SO-), and an alkylsulfonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -SO2-). Examples of the group in which -CH2- contained in the chain hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- include a hydroxy group (a group in which -CH2- contained in the methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in the ethyl group is replaced by -O-CO-), an alkoxy group (a group in which -CH2- at any position contained in the alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -CO-), Groups in which the -CH2- in the group is replaced by -S-, etc. can be mentioned. Alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyl The oxy group is, for example, an alkoxy group having 1 to 17 carbon atoms, an alkoxycarbonyl group having 2 to 17 carbon atoms, an alkylcarbonyl group having 2 to 18 carbon atoms, and an alkylcarbonyloxy group having 2 to 17 carbon atoms can be mentioned, and the same groups as above can be mentioned. As the alkylthio group, an alkylthio group having 1 to 17 carbon atoms can be mentioned, for example, a methylthio group, an ethylthio group, a propylthio group, etc. can be mentioned. In addition, the replacement in the alkenyl group and the alkynyl group may be any group containing a carbon-carbon double bond or a carbon-carbon triple bond at an arbitrary position in the examples of the replacement in the alkyl group described above. In the examples of the replacement in the alkyl group described above, as long as it contains a carbon-carbon double bond or a carbon-carbon triple bond at an arbitrary position. That's all right. The alicyclic hydrocarbon group may be monocyclic, polycyclic or spirocyclic, and may be saturated or unsaturated. As the alicyclic hydrocarbon group, a monocyclic cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cyclododecyl group, etc., and a polycyclic cycloalkyl group such as a norbornyl group, an adamantyl group, etc. can be mentioned. As the alicyclic hydrocarbon group, a monocyclic cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cyclododecyl group, etc., and a polycyclic cycloalkyl group such as a norbornyl group, an adamantyl group, etc. can be mentioned. As the alicyclic hydrocarbon group, a monocyclic cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cyclododecyl group, etc., and a polycyclic cycloalkyl group such as a norbornyl group, an adamantyl group, etc. can be mentioned. As the alicyclic hydrocarbon group, a monocyclic cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cyclododecyl group, etc., and a polycyclic cycloalkyl group such as a norbornyl group, an adamantyl group, etc. can be mentioned. As the group in which the alicyclic hydrocarbon group and the -CH2- contained in the alicyclic hydrocarbon group are replaced by -O-, -S-, - CO- or -SO2-, specifically, the following groups, etc. can be mentioned. The bonding site can be at any position. TIFF2025108538000014.tif130161 As the group in which the alicyclic hydrocarbon group and the -CH2- contained in the alicyclic hydrocarbon group are replaced by -O-, -S-, - CO- or -SO2-, groups represented by the formulas (y1) to (y71) is preferable, and a group represented by any one of Formula (y1) to Formula (y20), Formula (y26), Formula (y27), Formula (y30), Formula (y31), Formula (y39) to Formula (y71) is more preferable, and a group represented by the formula (y3), (y4), Formula (y9), Formula (y11), Formula (y14), Formula (y15), Formula (y 16), Formula (y20), Formula (y26), Formula (y27), Formula (y30), Formula (y31), Formula (y39), Formula (y40), Formula (y42), Formula (y43), Formula (y49) to Formula (y58) Formula (y62) to Formula (y71) is even more preferable. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 36, more preferably 3 to 24, even more preferably 3 to 18, and still more preferably 3 to 16.

[0022] Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, naphthyl group, biphenyl group, anthryl group, phenanthryl group, binaphthyl group and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 36, more preferably 6 to 24, even more preferably 6 to 18, still more preferably 6 to 14, and even still more preferably 6 to 10 is. In the case of a combined group, groups having different valences in the above-mentioned groups (alkanediyl group, alkanetriyl group, alkanetetrayl group, cycloalkanediyl group, cycloalkanetriyl group, cycloalkanetetrayl group, etc.) may be included.

[0023] The combined group means a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group (wherein -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), A group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group (wherein the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), and a group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group (wherein the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2 ). In the combination, the alicyclic hydrocarbon group, the chain hydrocarbon group and the aromatic hydrocarbon group may each be combined with two or more kinds. Specifically, examples of the combined group include an alicyclic hydrocarbon group-chain hydrocarbon group-* such as an adamantylmethylene group or a cyclohexylmethylene group, ((alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-alicyclic hydrocarbon group-* such as a methyladamantyl group or a dimethyladamantyl group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-*) (wherein the -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-* such as a tolyl group or a xylyl group (wherein the -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2), a chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-* such as a tolyl group or a xylyl group (wherein the -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2), a chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-* such as a tolyl group or a xylyl group (wherein the -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2), a chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -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-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, ((chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*), ((chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-*) (wherein the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2), The -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2- (it may be replaced). Aromatic hydrocarbon group such as benzyl group - chain hydrocarbon group - * (the -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-). (it may be replaced). Chain hydrocarbon group such as tolylmethyl group - aromatic hydrocarbon group - chain hydrocarbon group - * (the -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-). (it may be replaced). (it may be replaced). Chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group such as methyladamantane methylene adamantyl group, di(methyladamantane methylene)adamantyl group - * (chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group)2 - alicyclic hydrocarbon group - * (chain hydrocarbon group - alicyclic hydrocarbon group)2 - chain hydrocarbon group - alicyclic hydrocarbon group - * (chain hydrocarbon group)2 - alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - * (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, - CO- or -SO2-). (it may be replaced). (it may be replaced). Alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - * (alicyclic hydrocarbon group)2 - chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - * (alicyclic hydrocarbon group - chain hydrocarbon group)2 - alicyclic hydrocarbon group - chain hydrocarbon group - * (alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group)2 - chain hydrocarbon group - * (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, - CO- or -SO2-). (it may be replaced). (it may be replaced). Chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - *, (chain hydrocarbon group)2 - alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - *, (chain hydrocarbon group - alicyclic hydrocarbon group)2 - chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - *, (chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group)2 - alicyclic hydrocarbon group - chain hydrocarbon group - *, (chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group)2 - chain hydrocarbon group - * (the chain hydrocarbon group and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -S O2-), etc. are exemplified. Here, * represents the bonding position with the carbon atom of the carbonyl group.

[0024] X 01 、X 02 and X 03 When -CH2- contained in the hydrocarbon group represented by is replaced by -O-, - S-, -CO- or -SO2-, the carbon number before replacement is taken as the total carbon number of the hydrocarbon group. Also, when a substituent is bonded to the hydrocarbon group represented by X 01 、X 02 and X 03 , the carbon number before substitution is taken as the total carbon number of the hydrocarbon group. When a substituent is bonded to the hydrocarbon group represented by X X 01 、X 02 and X 03 The hydrocarbon group represented by may have one or more substituents too. Examples of the substituent include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, a carbon atom number of 2 to 13 alkylcarbonyl group, a carbon number of 2 to 13 alkylcarbonyloxy group, carbon atoms 2 to 13 alkylcarbonyl group, carbon atoms 2 to 13 alkylcarbonyloxy group, carbon Examples thereof include alicyclic hydrocarbon groups having 3 to 12 carbon atoms, aromatic hydrocarbon groups having 6 to 10 carbon atoms, or groups combining these groups. Examples include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the alkyl group having 1 to 12 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, octyl group, nonyl group, etc. Examples of the alkoxy group having 1 to 12 carbon atoms include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, etc. Examples of the alkoxycarbonyl group having 2 to 13 carbon atoms, the alkylcarbonyl group having 2 to 13 carbon atoms, and the alkylcarbonyloxy group having 2 to 13 carbon atoms include groups in which a carbonyl group or a carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of the alkoxycarbonyl group having 2 to 13 carbon atoms include methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group, etc. Examples of the alkylcarbonyl group having 2 to 13 carbon atoms include acetyl group, propionyl group, and butyryl group. Examples of the alkylcarbonyloxy group having 2 to 13 carbon atoms include acetyloxy group, propionyloxy group, and butyryloxy group. Examples of the alicyclic hydrocarbon group having 3 to 12 carbon atoms include the groups shown below. ** represents the bonding position with X. Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl group, naphthyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a phenyl group is bonded to a cyclohexyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a naphthyl group is bonded to a cyclopentyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a phenyl group is bonded to a cyclooctyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a naphthyl group is bonded to a cyclohexenyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a phenyl group is bonded to a cyclopentenyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a naphthyl group is bonded to a cycloheptyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a phenyl group is bonded to a cyclopropylmethyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a naphthyl group is bonded to a 2-methylcyclopentyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a phenyl group is bonded to a 3-methylcyclohexyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a naphthyl group is bonded to a 4-methylcyclohexyl group, etc. Examples of the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a group in which a phenyl group is bonded to a 2,3-dimethylcyclopentyl group, etc. Examples of the alicyclic hydrocarbon group having 3 to 12 carbon atoms include the following groups. ** represents the bonding position with X. 0 represents the bonding position with X. TIFF2025108538000015.tif17162 As the aromatic hydrocarbon group having 6 to 10 carbon atoms, aryl groups such as phenyl group and naphthyl group can be mentioned. As the combined group, a group combining a hydroxy group and an alkyl group having 1 to 12 carbon atoms a group combining an alkyl group having 1 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms a group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms and the like can be mentioned. As the group combining a hydroxy group and an alkyl group having 1 to 12 carbon atoms, hydroxyalkyl groups having 1 to 12 carbon atoms such as hydroxymethyl group and hydroxyethyl group can be mentioned and the like. As the group combining an alkyl group having 1 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms, aralkyl groups having 7 to 22 carbon atoms such as benzyl group, alkylaryl groups having 7 to 22 carbon atoms such as tolyl group and xylyl group can be mentioned and the like. As the group combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms, cyclohexylphenyl group and the like can be mentioned and the like.

[0025] X 0 As the hydrocarbon group represented by, preferably, an aliphatic hydrocarbon group having 1 to 7 carbon atoms which may have a substituent (the -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent, a group represented by formula (aa) or a group represented by formula (bb), and more preferably, an alicyclic hydrocarbon group which may have a hydroxy group or a fluorine atom (the -CH2- contained in the alicyclic hydrocarbon group may be -O-, -S-, -CO- or -SO2 ), and even more preferably, an alicyclic hydrocarbon group which may have a hydroxy group or a fluorine atom (the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2 ).​​​ may be replaced by), a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2 -, -CH2- contained in the chain hydrocarbon group may be replaced by -O- or - CO-, the alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom or a hydroxy group.)., may have a fluorine atom or a hydroxy group is an aromatic hydrocarbon group, a group represented by formula (aa) or a group represented by formula (bb), more preferably, *-alicyclic hydrocarbon group (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and the alicyclic hydrocarbon group may have a hydroxy group or a fluorine atom. * represents the bonding position with the carbon atom of -COO - ).), *-alicyclic hydrocarbon group-chain hydrocarbon group (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, the alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom or a hydroxy group. * represents the bonding position with the carbon atom of -COO ).), *-chain hydrocarbon group- alicyclic hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, - -CO- or -SO2-, the chain hydrocarbon group and the alicyclic hydrocarbon group may have a fluorine atom or a hydroxy group. * represents the bonding position with the carbon atom of -COO ).), *-chain hydrocarbon group- alicyclic hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, the chain hydrocarbon group and the alicyclic hydrocarbon group may have a fluorine atom or a hydroxy group. * represents the bonding position with the carbon atom of -COO - with the carbon atom of represents a binding site.), an aromatic hydrocarbon group which may have a fluorine atom or a hydroxy group, is a group represented by formula (aa) or a group represented by formula (bb), more preferably, a polycyclic alicyclic hydrocarbon group (in the polycyclic alicyclic hydrocarbon group, -CH2- contained may be replaced by -O-, -S-, -CO- or -SO2- and the polycyclic alicyclic hydrocarbon group may have a hydroxy group or a fluorine atom. * represents the binding site to the carbon atom of -COO - ), a polycyclic alicyclic hydrocarbon group - a chain hydrocarbon group (in the polycyclic alicyclic hydrocarbon group, -CH2- contained may be replaced by -O-, -S-, -C O- or -SO2-, and in the chain hydrocarbon group, -CH2- may be replaced by -O- or -CO-. The polycyclic alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom or a hydroxy group. * represents -COO - the carbon atom binding site. ), a chain hydrocarbon group - a polycyclic alicyclic hydrocarbon group (in the chain hydrocarbon group, -CH2- contained may be replaced by -O- or -CO-, and in the poly cyclic alicyclic hydrocarbon group, -CH2- contained may be replaced by -O-, -S-, -CO- or -SO 2-. The chain hydrocarbon group and the polycyclic alicyclic hydrocarbon group may have a fluorine atom or a hydroxy group. * represents -COO - the binding site to the carbon atom of ), an aromatic hydrocarbon group which may have a fluorine atom or a hydroxy group, a group represented by formula (aa) or a group represented by formula (bb), Particularly preferably, an adamantanone group, a hydroxyadamantyl group, a group combining an adamantyl group and an alkyl group (in the alkyl group, -CH2- contained may be replaced by -O- or -CO - may be replaced with), a group represented by the formula (Y30F), having a hydroxy group a phenyl group, a group represented by the formula (aa) or a group represented by the formula (bb). In the above groups, the number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 36, more preferably 3 to 24, still more preferably 3 to 18, even more preferably 3 to 1 6, and even more preferably 3 to 12. The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, still more preferably 1 to 9, and even more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 36, more preferably 6 to 24, still more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 1 0. TIFF2025108538000016.tif26125 [In the formula (aa), X a and X b each independently represents -O- or -S-. X 1a represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-. X 2a represents a hydrocarbon group having 1 to 48 carbon atoms which may have a substituent, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-. * represents the bonding position with the carbon atom of the carbonyl group.] [In the formula (bb), L A represents an alkanediyl group having 1 to 6 carbon atoms which may have a fluorine atom. L​​B represents a single bond or an alkanediyl group having 1 to 6 carbon atoms, and the -CH2- contained in the alkanediyl group may be replaced by -O-, -S-, -CO- or -SO2-. R A represents a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and the -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-. * represents the bonding position with the carbon atom of the carbonyl group.

[0026] X a and X b are preferably the same atom, and more preferably both are oxygen atoms.

[0027] X 1a and X 2a Examples of the hydrocarbon group represented by include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group formed by combining two or more of these. Note that these hydrocarbon groups may have a substituent. Further, the -CH2- contained in these hydrocarbon groups may be replaced by -O-, -S-, -CO- or -SO2-. Here, the number of carbon atoms of the hydrocarbon group means the number of carbon atoms of the hydrocarbon group without a substituent and without replacement. -CO- or -SO2-. Here, the number of carbon atoms of the hydrocarbon group means the number of carbon atoms of the hydrocarbon group without a substituent and without replacement.

[0028] X 1a Examples of the aliphatic hydrocarbon group of include chain hydrocarbon groups such as alkanetriyl groups, alicyclic hydrocarbon groups, or groups formed by combining these. Specific examples of the alkanetriyl group include a methine group, an ethanetriyl group, a propanetriyl group, a butanetriyl group, a pentanetriyl group, a hexanetriyl group, a heptanetriyl group, an octanetriyl group, a nonanetriyl group, a decanetriyl group, an undecanetriyl group, an octanetriyl group, a nonanetriyl group, a decanetriyl group, an undecanetriyl group, Examples of the alkyl group include a cycloalkyl group and a dodecanetriyl group.

[0029] The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclobutanetriyl group, a cyclopentanetriyl group, and a cyclopentanetriyl group. Examples of the alkyl group include a cyclohexyl group, a cyclohexanetriyl group, and a cyclooctanetriyl group. Examples of the polycyclic alicyclic hydrocarbon group include a norbornane triyl group, a norbornane triyl group, group, adamantanetriyl group, and the like. Examples of the aromatic hydrocarbon group include a benzenetriyl group, a naphthalenetriyl group, an anthracene group, and Examples of the aryl group include phenyltriyl group. In the case of a combination of groups, the above groups each having a different valence (alkyl group, alkanediyl group, etc.) aryl group, alkanetetrayl group, cycloalkyl group, cycloalkanediyl group, cycloalkane cantetrayl group, etc.) may be included.

[0030] X 1a The hydrocarbon group represented by the formula (I) has 1 to 24 carbon atoms and further has one or more substituents. The substituent may be a hydroxy group, a halogen atom, a cyano group, a carbon number Alkyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 12 carbon atoms, alkoxy groups having 2 to 13 carbon atoms alkylcarbonyl group having 2 to 13 carbon atoms, alkylcarbonyl group having 2 to 13 carbon atoms nyloxy group, alicyclic hydrocarbon group having 3 to 12 carbon atoms, aromatic hydrocarbon group having 6 to 10 carbon atoms Or a group combining these may be mentioned. Halogen atoms, alkyl groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkyl group, alkylcarbonyloxy group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and Examples of the group combining the above include the same groups as above.

[0031] X 1a The hydrocarbon group represented by the formula (I) is an alkane group having 1 to 6 carbon atoms which may have a substituent. It is preferably an aryl group or an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent. Alkanetriyl groups having 1 to 6 carbon atoms, represented by formulas (w1-1) to (w1-11), More preferably, it is an alkanetriyl group having 1 to 6 carbon atoms, a group represented by the formula (w1-1): a polycyclic hydrocarbon group such as a group represented by formula (w1-3) or a group represented by formula (w1-2) or a monocyclic hydrocarbon group such as a group represented by formula (w1-6): It is. TIFF2025108538000017.tif53143 [Formula (w1-1) to formula (w1-11), The ring may be a hydroxyl group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, or a an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, Alkylcarbonyl group, alkylcarbonyloxy group having 2 to 13 carbon atoms, alkylcarbonyloxy group having 3 to 12 carbon atoms an alicyclic hydrocarbon group having 6 to 10 carbon atoms, or a combination thereof It may have. * indicates the bond position.]

[0032] X 2a The number of carbon atoms in the hydrocarbon group represented by the formula (I) is preferably 2 to 48, and more preferably 4 to 48. It is more preferable that the ratio is 6 to 44, and further preferably 8 to 40. It is more preferable that the ratio is 10 to 38, and even more preferable that the ratio is 10 to 38. Here, the number of carbon atoms in the hydrocarbon group is the number of carbon atoms in the hydrocarbon group that does not have a substituent and is not replaced. It means prime number.

[0033] X 2aExamples of the substituent that the hydrocarbon group in [substance name] may have include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a carbon number 2 to 13 alkoxycarbonyl group, an alkylcarbonyl group having 2 to 13 carbon atoms, a carbon number 2 to 13 alkylcarbonyloxy group, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, a carbon number 6 to 10 aromatic hydrocarbon group or a group combining these, etc. Examples of the halogen atom, alkyl group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alicyclic hydrocarbon group, aromatic hydrocarbon group and a group combining these are the same groups as described above. X 2a The hydrocarbon group represented by [substance name] having 1 to 48 carbon atoms may have one substituent or a plurality of substituents .

[0034] X 2a Examples of the hydrocarbon group in [substance name] include a linear or branched chain hydrocarbon group (e.g., an al kanediyl group, etc.), a monocyclic or polycyclic alicyclic hydrocarbon group, and an aromatic hydrocarbon group , and those combining two or more of these groups may also be used. Specifically, a linear 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, a hexane-1,6-diyl group, a heptane-1 ,7-diyl group, an octane-1,8-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 Branched alkanediyl groups such as a group, 2-methylbutane-1,4-diyl group; Cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohex ane-1,4-diyl group, cyclooctane-1,5-diyl group and other monocyclic cycloalkanedi yl groups which are monocyclic alicyclic hydrocarbon groups; Norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane- 1,5-diyl group, adamantane-2,6-diyl group and other polycyclic cycloalkanediyl groups which are polycyclic alicyclic hydrocarbon groups; Aromatic hydrocarbon groups such as phenylene group, naphthylene group, biphenylene group, anthrylene group, phenanthrylene group , binaphthylene group and the like can be mentioned. In the case of a combined group, groups with different valences in the above-mentioned groups (alkyl group, alkanetri yl group, alkanetetrayl group, cycloalkyl group, cycloalkanetriyl group, cyclo alkanetetrayl group, etc.) may be included. Examples of the combined group include a group combining a chain hydrocarbon group and an alicyclic hydrocarbon group, a chain hydrocarbon group and an aromatic hydrocarbon group, a group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group and the like. Specifically, a group in which one or more alicyclic hydrocarbon groups are bonded to a chain hydrocarbon group (for example, -chain hydrocarbon group-alicyclic hydrocarbon group, -chain hydrocarbon group-(alicy clic hydrocarbon group)2, etc.), a group in which one or more chain hydrocarbon groups are bonded to an alicyclic hydrocarbon group (e.g ., -alicyclic hydrocarbon group-chain hydrocarbon group, -alicyclic hydrocarbon group-(chain hydrocarbon group) 2, etc.), a group in which one or more alicyclic hydrocarbon groups and a chain hydrocarbon group are bonded to a chain hydrocarbon group (e.g ., -chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group, -chain hydrocarbon group-(alicy clic hydrocarbon group-chain hydrocarbon group)2, etc.) and the like can be mentioned.

[0035] X 2a As the hydrocarbon group in a chain hydrocarbon group having 2 to 18 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent .), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by - O-, -S-, -CO- or -SO2-, and the alicyclic hydrocarbon group may have a substituent.), or, a group combining a chain hydrocarbon group having 1 to 12 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-) and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2- ). The group may have a substituent and is preferably a chain hydrocarbon group having 4 to 18 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent .), or, a group combining a chain hydrocarbon group having 1 to 12 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-) and an alicyclic hydrocarbon group having 3 to 16 carbon atoms (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2- ). The group may have a substituent and is preferably a chain hydrocarbon group having 6 to 14 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- Or it may be replaced by -CO-, and the chain hydrocarbon group may have a substituent. ), or a chain hydrocarbon group having 1 to 12 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-).) and an alicyclic hydrocarbon group having 5 to 14 carbon atoms (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2- ).) A combined group (the group may have a substituent). is more preferably present.

[0036] Specifically, as the hydrocarbon group in X 2a is an alkanediyl group having 2 to 18 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by - O- or -CO-, and the alkanediyl group may have a substituent. ), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by - O-, -S-, -CO- or -SO2-, and the alicyclic hydrocarbon group may have a substituent. an alkanediyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by - O- or -CO-).) and an alicyclic hydrocarbon group having 3 to 18 carbon atoms ( wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2- .) A group consisting of (the group may have a substituent). Or an alkanediyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by - O- or -CO-).) and an alicyclic hydrocarbon group having 3 to 18 carbon atoms and An alkyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO -).) A group composed of (the group may have a substituent). It is preferably An alkanediyl group having 4 to 18 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by - O- or -CO-, and the alkanediyl group may have a substituent). ), An alkanediyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by - O- or -CO-).) And an alicyclic hydrocarbon group having 3 to 16 carbon atoms ( -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2 -).) A group composed of (the group may have a substituent). Or An alkanediyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by - O- or -CO-).) And an alicyclic hydrocarbon group having 3 to 16 carbon atoms and An alkyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO -).) A group composed of (the group may have a substituent). It is more preferably An alkanediyl group having 6 to 14 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by - O- or -CO-, and the alkanediyl group may have a substituent). ), An alkanediyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by - O- or -CO-).) And an adamantanediyl group (the adamantan -CH2- contained in the diyl group may be replaced by -O- or -CO-). (The group may have a substituent.) Or An alkanediyl group having 1 to 12 carbon atoms (the -CH2- contained in the alkanediyl group is - may be replaced by -O- or -CO-.) and an adamantanediyl group and a C1-C1 2 alkyl group (-CH2- contained in the alkyl group is replaced by -O- or -CO-) and (the group may have a substituent). Even more preferred.

[0037] Specifically, X 2a is the formula (X 2 -1), a group represented by the formula (X 2 -2), a group represented by the formula (X 2 -3) or a group represented by the formula (X 2 -4) is preferred. TIFF2025108538000018.tif34157[In the formula, R 1x , R 2x , R 3x , R 4x , R 5x and R 6x each independently represents an alkyl group having 1 to 6 carbon atoms; an alkyl group, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a combination of two or more of these groups The alkyl group and the -CH2- contained in the alicyclic hydrocarbon group represent -O-, -S The alkyl group and the alicyclic carbon atom may be replaced by -, -CO- or -SO2-. The hydrogen group may have a substituent. * is X a and X b represents the bond position with The combined group is a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined one by one. The group may be a combination of two or more of either one or two or more of both. The combined carbon number of the groups is 39 or less, preferably 37 or less.

[0038] Among them, R 1x , R 2x , R 3x , R 4x , R 5x and R 6x As for the carbon number 1-6, An alkyl group (wherein the -CH2- in the alkyl group is replaced with -O- or -CO-) The alkyl group may have a substituent. A cycloaliphatic hydrocarbon group (the -CH2- contained in the alicyclic hydrocarbon group is -O-, -S-, -CO- or The alicyclic hydrocarbon group may have a substituent. ) or an alkyl group having 1 to 6 carbon atoms (the -CH2- contained in the alkyl group is -O- or may be replaced by -CO-) and an alicyclic hydrocarbon group having 5 to 12 carbon atoms (the alicyclic The -CH2- contained in the hydrocarbon group of the formula may be replaced with -O-, -S-, -CO- or -SO2-. and a group which may have a substituent. It is preferable that the methoxy group, the adamantyl group (the —CH 2- may be replaced by -O- or -CO-, and the adamantyl group has a substituent ) or an alkyl group having 1 to 6 carbon atoms (the —CH2 - may be replaced by -O- or -CO-. It is more preferable that the group is a group having a substituent (which may have a substituent).

[0039] In formula (bb), L A and L B As the alkanediyl group having 1 to 6 carbon atoms, , for example, a straight-chain 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, a hexane-1,6-diyl group, etc.; a branched-chain alkanediyl group such as a propane-1,2-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a 1-methylbutane-1,4-diyl group, a 2-methylbutane-1,4-diyl group, etc. Examples of the alkanediyl group include those mentioned above. The number of carbon atoms in the alkanediyl group is preferably 1 to 4, more preferably 1 to 3. Examples of the alkanediyl group include straight-chain 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, etc. ; branched-chain alkanediyl groups such as a propane-1,2-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a 1-methylbutane-1,4-diyl group, a 2-methylbutane-1,4-diyl group, etc. Examples of the alkanediyl group include branched-chain alkanediyl groups such as a propane-1,2-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a 1-methylbutane-1,4-diyl group, a 2-methylbutane-1,4-diyl group, etc. Examples of the alkanediyl group include those mentioned above. The number of carbon atoms in the alkanediyl group is preferably 1 to 4, more preferably 1 to 3. Examples of the alkanediyl group which may have a fluorine atom include perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropane-1,3-diyl group, a perfluorobutane-1,4-diyl group, a perfluoropentane-1,5-diyl group, etc. When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). Examples of the alkanediyl group which may have a fluorine atom include perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropane-1,3-diyl group, a perfluorobutane-1,4-diyl group, a perfluoropentane-1,5-diyl group, etc. Examples of the alkanediyl group which may have a fluorine atom include perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropane-1,3-diyl group, a perfluorobutane-1,4-diyl group, a perfluoropentane-1,5-diyl group, etc. Examples of the alkanediyl group which may have a fluorine atom include perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropane-1,3-diyl group, a perfluorobutane-1,4-diyl group, a perfluoropentane-1,5-diyl group, etc. When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). When the -CH2- contained in the alkanediyl group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the alkanediyl group. The alkanediyl group may be a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which any -CH2- contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which any -CH2-CH2- contained in an alkyl group is replaced by -CO-O-). an alkandiyl-oxy group (a group in which - CH2- at any position in the alkandiyl group is replaced by -O-), an alkandiyl-oxycarbonyl group (a group in which - CH2-CH2- at any position in the alkandiyl group is replaced by -O-CO-), an alkandiyl-carbonyl group (a group in which -CH2 - at any position in the alkandiyl group is replaced by -CO-), an alkandiyl-carbonyl-oxy group (a group in which - CH2-CH2- at any position in the alkandiyl group is replaced by -CO-O-), may be included. As the alkandiyl-oxy group, for example, a methylene-oxy group, an ethylene-oxy group, a propandiyl-oxy group, a butandiyl-oxy group, a pentandiyl-oxy group, etc. can be mentioned. . As the alkandiyl-oxycarbonyl group, for example, a methylene-oxycarbonyl group, an ethylene-oxycarbonyl group, a propandiyl-oxycarbonyl group, a butandiyl-oxy carbonyl group, etc. can be mentioned. As the alkandiyl-carbonyl group, for example, a methylene-carbonyl group, an ethylene-carbon yl group, a propandiyl-carbonyl group, a butandiyl-carbonyl group, a pentandiyl-carbon yl group, etc. can be mentioned. As the alkandiyl-carbonyl-oxy group, for example, a methylene-carbonyl-oxy group, an ethylene-carbonyl-oxy group, a propandiyl-carbonyl-oxy group, a butandiyl-carbon yl-oxy group, etc. can be mentioned. L A is preferably an alkandiyl group having 1 to 4 carbon atoms which may have a fluorine atom, more preferably an alkandiyl group having 1 to 3 carbon atoms having a fluorine atom. L Bis a single bond or an alkanediyl group having 1 to 3 carbon atoms (wherein -CH2- may be replaced by -O- or -CO-), preferably a single bond, a methylene group or an ethylene group.

[0040] R A The hydrocarbon group in is an aliphatic hydrocarbon group (a chain hydrocarbon group such as an alkyl group, an alkenyl group, an alkynyl group, etc. and an alicyclic hydrocarbon group), an aromatic hydrocarbon group and a group formed by combining these. 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, an n-hexyl group, an n-heptyl group, a 2-ethylhexyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, etc. The number of carbon atoms of the alkyl group is preferably 1 to 18, more preferably 1 to 12, still more preferably 1 to 9, even more preferably 1 to 6, and even more preferably 1 to 4. Examples of the alkenyl group include an ethenyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, an isooctenyl group, a nonenyl group. 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, a nonynyl group, etc. -CH2- contained in the chain hydrocarbon group is -O-, -S-, -CO- or -SO2- Examples of the replaced group include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkylthio group, etc. Examples of the alkoxy group, the alkoxycarbonyl group, the alkylcarbonyl group, the alkylcarbonyloxy group, and the alkylthio group include an alkoxy group having 1 to 17 carbon atoms, an alkoxycarbonyl group having 2 to 17 carbon atoms, an alkylcarbonyl group having 2 to 18 carbon atoms, an alkylcarbonyloxy group having 2 to 17 carbon atoms, and an alkylthio group having 1 to 17 carbon atoms. Groups similar to the above-described groups can be mentioned. The alicyclic hydrocarbon group may be monocyclic, polycyclic, or spiro, and may be saturated or unsaturated. Examples of the monocyclic alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, and a cyclododecyl group. Examples of the polycyclic alicyclic hydrocarbon group include polycyclic cycloalkyl groups such as a decahydronaphthyl group, an adamantyl group, and a norbornyl group. Examples of the group in which the alicyclic hydrocarbon group and -CH2- contained in the alicyclic hydrocarbon group are replaced by -O-, -S-, -CO- or -SO2- specifically include the groups represented by the above formulas (y1) to (y7). The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 36, more preferably 3 to 24, still more preferably 3 to 18, even 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, Examples include aryl groups such as a phenanthryl group and a binaphthyl group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 36, more preferably 6 to 24, still more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. In the case of a combined group, groups with different valences in the above-mentioned groups (such as an alkanediyl group, an alkanetriyl group, a cycloalkanediyl group, a cycloalkanetriyl group, etc.) may be included. Examples of the group formed by combination include a group combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, an aromatic hydrocarbon group - alkanediyl group - *, an alkyl group - aromatic hydrocarbon group - *), a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, an alicyclic hydrocarbon group - alkanediyl group - *, an alkyl group - alicyclic hydrocarbon group - *), and a group 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 - *). * represents a bonding site. Examples of the aromatic hydrocarbon group - alkanediyl group - * include aralkyl groups such as a benzyl group and a phenethyl group. Examples of the alkyl group - aromatic hydrocarbon group - * include a tolyl group, a xylyl group, a cumenyl group, etc. 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, a 1-(adamantan-1-yl)-1-methylethyl, etc. Examples of the alkyl group - alicyclic hydrocarbon group - * include a methylcyclohexyl group and a dimethylcyclohexyl group. Cycloalkyl groups having an alkyl group such as a cyclohexyl group or a 2-alkyladamantan-2-yl group and the like can be mentioned. Examples of the aromatic hydrocarbon group - alicyclic hydrocarbon group - * include a phenyladamantyl group and the like. can be mentioned. Examples of the alicyclic hydrocarbon group - aromatic hydrocarbon group - * include an adamantylphenyl group and the like. can be mentioned. In addition, in the combination, the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and the chain hydrocarbon group may be combined with two or more of each other. Also, any group may be bonded to L B either. is fine. Examples of the group in which -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- include, in addition to the groups described above, a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, an aromatic hydrocarbon group - carbonyloxy group, and a group formed by combining two or more of these groups. Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 17 carbon atoms, such as a cyclohexyloxy group. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as a cyclohexylmethoxy group. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as a butoxycarbonyloxy group. Examples of the aromatic hydrocarbon group - carbonyloxy group include aromatic hydrocarbon group - carbonyloxy groups having 7 to 17 carbon atoms, such as a benzoyloxy group. can be mentioned. Examples of the group in which -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include, in addition to the groups described above, a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, an aromatic hydrocarbon group - carbonyloxy group, and a group formed by combining two or more of these groups. Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 17 carbon atoms, such as a cyclohexyloxy group. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as a cyclohexylmethoxy group. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as a butoxycarbonyloxy group. Examples of the aromatic hydrocarbon group - carbonyloxy group include aromatic hydrocarbon group - carbonyloxy groups having 7 to 17 carbon atoms, such as a benzoyloxy group. When it is different, the number of carbon atoms before replacement is defined as the total number of carbon atoms of the hydrocarbon group. Also, the number may be one or two or more.

[0041] R A Examples of the substituent that the hydrocarbon group of R may have include a halogen atom, a cyano group, and an alkyl group having 1 to 12 carbon atoms (the -CH2- contained in the alkyl group may be replaced by -O-, -S-, -C O- or -SO2-). Examples of the halogen atom include the same groups as those described above. Examples of the alkyl group having 1 to 12 carbon atoms include the same groups as those described above. Examples of the group in which -CH2- contained in the alkyl group is replaced by -O- or -CO- include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, and the like. Examples of the alkoxy group, the alkoxycarbonyl group, the alkylcarbonyl group, and the alkylcarbonyloxy group include an alkoxy group having 1 to 11 carbon atoms, an alkoxycarbonyl group having 2 to 11 carbon atoms, an alkylcarbonyl group having 2 to 12 carbon atoms, and an alkylcarbonyloxy group having 2 to 11 carbon atoms, and for example, the same groups as those described above. R A The hydrocarbon group in

[0042] R may have one substituent or a plurality of substituents. A Examples of the hydrocarbon group in R include an alkyl group having 1 to 12 carbon atoms which may have a substituent (however, the -CH2- contained in the alkyl group may be replaced by -O-, -S-, -CO- or -SO2 -), or a cyclic hydrocarbon having 3 to 18 carbon atoms which may have a substituent. A prime group (however, -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.), Preferably, it may have a fluorine atom, a hydroxy A cyclic hydrocarbon group having a group or an alkyl group having 1 to 6 carbon atoms and having 3 to 18 carbon atoms (however However, -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2 -.).

[0043] Examples of the cyclic hydrocarbon group include a monocyclic or polycyclic alicyclic hydrocarbon group having 3 to 18 carbon atoms and A cyclic hydrocarbon group such as an aromatic hydrocarbon group having 6 to 18 carbon atoms or a group combining these And the like. Examples of the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and the combined group are the same as those described above Of these. In addition, in the combination, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be each combined with two or more Of these. Also, any group may be L B May be bonded to.

[0044] A cyclic hydrocarbon group having 3 to 18 carbon atoms (the cyclic hydrocarbon group may have a fluorine atom, a hydroxy group or An alkyl group having 1 to 6 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group May be replaced by -O-, -S-, -CO- or -SO2-). It preferably has a fluorine atom, a hydroxy group or an alicyclic hydrocarbon group having 3 to 1 8 which may have an alkyl group having 4 carbon atoms (wherein -CH2- contained in the alicyclic hydrocarbon group may be -O-, -S-, -CO- or -SO2-), Or It preferably has a fluorine atom, a hydroxy group or an aromatic hydrocarbon group having 6 to 1 8, It may have a fluorine atom, a hydroxy group or an alkyl group having 1 to 4 carbon atoms, and is preferably an alicyclic hydrocarbon group having 3 to 1 8 (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O- or -CO -). Examples of the alicyclic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, and the following group (the bonding site is at an arbitrary position ). Preferred examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group. TIFF2025108538000019.tif1687

[0045] Examples of the anion (I) include carboxylic acid anions and the like described below. TIFF2025108538000020.tif98162

[0046] TIFF2025108538000021.tif118134

[0047] TIFF2025108538000022.tif126139

[0048] TIFF2025108538000023.tif124154

[0049] TIFF2025108538000024.tif155143

[0050] TIFF2025108538000025.tif218160

[0051] TIFF2025108538000026.tif192163

[0052] Specific examples of the carboxylate (IA) and the carboxylate (IB) include salts obtained by arbitrarily combining the above-mentioned cations and anions. The carboxylate (IA) and the carboxylic acid Specific examples of the salt (IB) are shown in the following table. In the following table, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation. . For example, the carboxylate salt (IA-1) is a salt composed of the anion represented by the formula (I-a-1) and the cation represented by the formula ( IA-c-1), and the carboxylate salt (IB-1) is a salt composed of the anion represented by the formula (I-a-1) and the cation represented by the formula (IB-c-1), and represents the salts shown below. TIFF2025108538000027.tif62129 [Table 1] TIFF2025108538000029.tif223166 TIFF2025108538000030.tif223166 TIFF2025108538000031.tif223166 TIFF2025108538000032.tif223166 TIFF2025108538000033.tif223166 TIFF2025108538000034.tif223166 TIFF2025108538000035.tif125165

[0053] [Table 2] TIFF2025108538000037.tif223165 TIFF2025108538000038.tif223165 TIFF2025108538000039.tif223165 TIFF2025108538000040.tif223165 TIFF2025108538000041.tif47155

[0054] Among them, the carboxylate (IA) includes carboxylates (IA-1) to carboxylates (IA- 5), carboxylates (IA-30) to carboxylates (IA-34), carboxylates (IA -59) to carboxylates (IA-63), carboxylates (IA-88) to carboxylates ( IA-92), carboxylates (IA-117) to carboxylates (IA-121), carboxyl ates (IA-146) to carboxylates (IA-150), carboxylates (IA-187 ) to carboxylates (IA-257), carboxylates (IA-282) to carboxylates (I A-292) are preferably used, and the carboxylate (IB) includes carboxylates (IB-1 ) to carboxylates (IB-5), carboxylates (IB-30) to carboxylates (IB-3 4), carboxylates (IB-59) to carboxylates (IB-63), carboxylates (IB -88) to carboxylates (IB-92), carboxylates (IB-125) to carboxylates (IB-173), carboxylates (IB-198) to carboxylates (IB-208) are preferably used.

[0055] <Method for Producing Carboxylate (IA)> The carboxylate (IA) can be produced by reacting a salt represented by the formula (I-a) and a salt represented by the formula (I-b) in the presence of a base catalyst in a solvent. TIFF2025108538000042.tif75152[In the formula, all symbols have the same meanings as described above.] Examples of the base include potassium carbonate. Examples of the solvent include chloroform, dimethylformamide, and acetonitrile. etc. The reaction temperature is usually 15°C to 140°C, and the reaction time is usually 0.5 to 24 hours. .

[0056] Examples of the salt represented by formula (I-a) include compounds represented by the following formula, and they can be easily obtained from the market. Moreover, these salts can also be obtained with reference to the methods described in JP-A-2011-39502, JP-A-2014-88367, and JP-A-2013-200561. TIFF2025108538000043.tif184151

[0057] Examples of the salt represented by formula (I-b) include salts represented by the following formula, and they can be easily obtained from the market. Moreover, these salts can also be obtained with reference to the methods described in JP-A-2011-39502, JP-A 2012-224611, JP-A-2014-88367, and JP-A-2013-20 0561. TIFF2025108538000044.tif167145

[0058] The carboxylate salt (IA) can also be produced by reacting the salt represented by formula (I-c) with the salt represented by formula (I-d) in a solvent in the presence of a base catalyst. [In the formula, all the symbols have the same meanings as described above.] TIFF2025108538000045.tif71150 Examples of the base include potassium carbonate. Examples of the solvent include chloroform, dimethylformamide, and acetonitrile. The reaction temperature is usually from 15°C to 140°C, and the reaction time is usually from 0.5 to 24 hours. .

[0059] Examples of the salt represented by formula (I-c) include compounds represented by the following formula, and they can be easily obtained from the market. ​​can be easily obtained. These salts can also be obtained with reference to the methods described in JP-A-2011-39502, JP-A-2014-88367, and JP-A-2013-200561. TIFF2025108538000046.tif209167

[0060] Examples of the salt represented by formula (I-d) include salts represented by the following formula, and they can be more easily obtained from the market. These salts can also be obtained with reference to the methods described in JP-A-2011-39502, JP-A- 2012-224611, JP-A-2014-88367, and JP-A-2013-20 0561. TIFF2025108538000047.tif223165

[0061] <Method for Producing Carboxylate (IB)> Carboxylate (IB) can be produced by reacting a salt represented by formula (I-a), a salt represented by formula (I-b1), and a salt represented by formula (I-a1) in a solvent in the presence of a base catalyst. TIFF2025108538000048.tif79166[In the formula, all symbols have the same meanings as described above.] Examples of the base include potassium carbonate. Examples of the solvent include chloroform, dimethylformamide, and acetonitrile. The reaction temperature is usually 15°C to 140°C, and the reaction time is usually 0.5 to 24 hours.

[0062] Examples of the salt represented by formula (I-a1) include compounds represented by the following formula, and they can be more easily obtained from the market. These salts can also be obtained with reference to the method described in JP-A-2011-39502. ​​, the method described in JP-A-2014-88367 and JP-A-2013-200561 can also be obtained by referring to it. It can also be obtained with reference. TIFF2025108538000049.tif208163

[0063] Examples of the salt represented by formula (I-b1) include salts represented by the following formula, and they can be easily obtained from the market. Further, these salts can also be obtained with reference to the methods described in JP-A-2011-39502, JP-A-2012-224611, JP-A-2014-88367, and JP-A-2013-200561. It can also be obtained with reference. JP-A-2012-224611, JP-A-2014-88367, JP-A-2013-2 00561 can also be obtained by referring to the methods described in the publications. TIFF2025108538000050.tif178165

[0064] The carboxylate (IB) can also be produced by reacting the salt represented by formula (I-c), the salt represented by formula (I-d1), and the salt represented by formula (I-c1) in a solvent in the presence of a base catalyst. Examples of the base include potassium carbonate. Examples of the solvent include chloroform, dimethylformamide, and acetonitrile. TIFF2025108538000051.tif76165[In the formula, all the symbols have the same meanings as described above.] Examples of the base include potassium carbonate. Examples of the solvent include chloroform, dimethylformamide, and acetonitrile. It can be mentioned. The reaction temperature is usually 15°C to 140°C, and the reaction time is usually 0.5 to 24 hours. It is.

[0065] Examples of the salt represented by formula (I-c1) include compounds represented by the following formula, and they can be easily obtained from the market. Further, these salts can also be obtained with reference to the methods described in JP-A-2011-39502, JP-A-2014-88367, and JP-A-2013-200561. It can also be obtained with reference. JP-A-2014-88367, JP-A-2013-200561 can also be obtained by referring to the methods described in the publications. It can be obtained with reference. TIFF2025108538000052.tif203164

[0066] Examples of the salt represented by the formula (I-d1) include salts represented by the following formula, and they can be easily obtained from the market. Also, these salts can be obtained with reference to the methods described in JP-A-2011-39502, JP-A-2012-224611, JP-A-2014-88367, and JP-A-2013-200561. TIFF2025108538000053.tif219170

[0067] 〔Carboxylic acid generator〕 The carboxylic acid generator of the present invention is an acid generator containing a carboxylate (I). The carboxylic acid generator may contain only one kind or two or more kinds of carboxylates (I). The carboxylate (I) of the present invention can act as an acid generator in the resist composition. The carboxylic acid generator of the present invention may contain a carboxylate known in the resist field other than the carboxylate (I). In this case, the content ratio (mass ratio) of the carboxylate (I) to the carboxylate other than the carboxylate (I) is usually 1:99 to 100:0, preferably 1:99 to 99:1, more preferably 2:98 to 98:2, and even more preferably 5:95 to 95:5.

[0068] 〔Resist composition〕 The resist composition contains a carboxylic acid generator containing the carboxylate (I) of the present invention, an acid generator (B) other than the carboxylate (I), and a resin having an acid-labile group (hereinafter sometimes referred to as "resin (A)"). Here, the "acid-labile group" has a leaving group and reacts with an acid. The leaving group is detached by contact to form a hydrophilic group (e.g., a hydroxy group or a carboxy group). It means a group that does so. The resist composition may further contain a quencher (hereinafter sometimes referred to as "quencher (C)") and / or a solvent (hereinafter sometimes referred to as "solvent (E)"). In the resist composition of the present invention, the content of the carboxylate (I) is preferably 0.1% by mass or more and 35% by mass or less, more preferably 0.5% by mass or more and 30 % by mass or less, and even more preferably 1% by mass or more and 25% by mass or less, based on the solid content of the resist composition.

[0069] <Acid generator (B)> When the resist composition of the present invention contains an acid generator (B) or the like, the ratio of the content of the carboxylate (I) to the content of the acid generator (B) (mass ratio; carboxylate (I): acid generator (B) or the like) is usually 1:99 to 100:0, preferably 1:99 to 99:1, more preferably 2:98 to 98:2, and even more preferably 5:95 to 95:5. Further, when the resist composition of the present invention contains an acid generator (B) or the like, the total content of the carboxylate (I ) and the acid generator (B) or the like is preferably 1 part by mass or more (more preferably 3 parts by mass or more) and preferably 55 parts by mass or less (more preferably 50 parts by mass or less, and even more preferably 45 parts by mass or less) with respect to 100 parts by mass of the resin (A).

[0070] As the acid generator (B), either a nonionic or an ionic one may be used. As the nonionic acid generator, sulfonate esters (e.g., 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxy ketone ) are mentioned. ​​​tons, diazonaphthoquinone 4 - sulfonate), sulfones (e.g., disulfone, keto sulfone, sulfonyldiazomethane), etc. Examples of ionic acid generators include oni um salts containing onium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts, iodonium salts). Examples of anions of onium salts include sulfonic acid ani ons, sulfonylimide anions, sulfonylmethide anions, etc.

[0071] As the acid generator (B), those 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. Patent No. 3,779, 778, U.S. Patent No. 3,849,137, German Patent No. 3914407, European Patent No. 126,712, etc., which generate an acid upon irradiation with radiation, can be used. Also, compounds produced by known methods may be used. The acid generator (B) may be used in combination of two or more.

[0072] The acid generator (B) is preferably a fluorine-containing acid generator, more preferably a salt represented by the formula (B1) (hereinafter sometimes referred to as "acid generator (B1)"). TIFF2025108538000054.tif2962[In the formula (B1), Q b1 and Q b2 each independently represents a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. L b1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, and the saturated hydrocarbon group contained therein -CH2- may be replaced by -O- or -CO-, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted by fluorine atoms or hydroxy groups. Y represents a methyl group which may have a substituent or an alicyclic hydrocarbon group having 3 to 2 4 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, - S(O)2- or -CO-. Z1 + represents an organic cation.]

[0073] Q b1 and Q b2 Examples of the perfluoroalkyl group represented by and Q include a trifluoromethyl group, perfluoro ethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluoro butyl group, perfluoro sec-butyl group, perfluoro tert-butyl group, perfluoro opentyl group, perfluorohexyl group and the like. Q b1 and Q b2 are each independently preferably a fluorine atom or a trifluoromethyl group, and more preferably both are fluorine atoms.

[0074] L b1 Examples of the divalent saturated hydrocarbon group in include a linear alkanediyl group, a branched alkane diyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and a group formed by combining two or more of these groups may also be used. Specifically, 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 , 1,10 - diyl group, undecane - 1,11 - diyl group, dodecane - 1,12 - diyl group, tridecane - 1,13 - diyl group, tetradecane - 1,14 - diyl group, pentadecane - 1,15 - diyl group, hexadecane - 1,16 - diyl group and heptadecane - 1,17 - diyl group and other linear alkanediyl groups; ethane - 1,1 - diyl group, propane - 1,1 - diyl group, propane - 1,2 - diyl group, propane - 2,2 - diyl group, pentane - 2,4 - diyl group, 2 - methylpropane - 1,3 - diyl group, 2 - methylpropane - 1,2 - diyl group, pentane - 1,4 - diyl group, 2 - methylbutane - 1,4 - diyl group and other branched alkanediyl groups; cyclobutane - 1,3 - diyl group, cyclopentane - 1,3 - diyl group, cyclohex ane - 1,4 - diyl group, cyclooctane - 1,5 - diyl group and other cycloalkanediyl groups which are monocyclic divalent alicyclic saturated hydrocarbon groups; norbornane - 1,4 - diyl group, norbornane - 2,5 - diyl group, adamantane - 1,5 - diyl group, adamantane - 2,6 - diyl group and other polycyclic divalent alicyclic saturated hydrocarbon groups and the like can be mentioned.

[0075] L b1 In the divalent saturated hydrocarbon group represented by, the -CH2- contained therein is replaced by -O- or -CO-, and the groups include, for example, the groups represented by any of formula (b1 - 1) to formula (b1 - 3). In addition, in the groups represented by formula (b1 - 1) to formula (b1 - 3) and the groups represented by formula (b1 - 4) to formula (b1 - 11) which are specific examples thereof, * and ** represent the bonding positions, and * represents the bonding position with -Y.

[0076] ​​​​TIFF2025108538000055.tif26117[in formula (b1-1), L b2 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b3 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxy groups, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. However, the total number of carbon atoms of L b2 and L b3 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 the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b5 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxy groups, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. However, the total number of carbon atoms of L b4 and L b5 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 the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxy groups. L b7 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxy groups, and the saturated carbon The -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. However, L b6 and L b7 The total number of carbon atoms of and is 23 or less.

[0077] In the groups represented by formulas (b1-1) to (b1-3), when the -CH2- contained in the saturated hydrocarbon group is replaced by -O- or -CO-, the number of carbon atoms before replacement is taken as the number of carbon atoms of the saturated hydrocarbon group. Examples of the divalent saturated hydrocarbon group include the same as the divalent saturated hydrocarbon group of L b1 L b2 is preferably a single bond. 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 the hydrogen atoms contained in the divalent saturated hydrocarbon group may be substituted by fluorine atoms. 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 the hydrogen atoms contained in the saturated hydrocarbon group may be substituted by fluorine atoms. L b7 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted by fluorine atoms or hydroxy groups, and the -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-. L 1 When the -CH2- contained in the divalent saturated hydrocarbon group represented by is replaced by -O- or -CO- As the alternative group, a group represented by the formula (b1-1) or the formula (b1-3) is preferable.

[0078] Examples of the group represented by the formula (b1-1) include groups represented by the formulas (b1-4) to (b1-8), respectively. TIFF2025108538000056.tif48120 [In the formula (b1-4), L b8 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. In the 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, the total number of carbon atoms of L b9 and L b10 is 20 or less. In the 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, the total number of carbon atoms of L b11 and L b12 is 21 or less. In the 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 the divalent saturated carbon​​​​​ The -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. L b15 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the hydrogen atoms contained in the divalent saturated hydrocarbon group may be replaced by fluorine atoms or hydroxy groups. However, the total number of carbon atoms of L b13 to L b15 is 19 or less. In formula (b1-8), L b16 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -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 the hydrogen atoms contained in the divalent saturated hydrocarbon group may be replaced by fluorine atoms or hydroxy groups. However, the total number of carbon atoms of L b16 to L b18 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, 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 b14is 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, 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 b18 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 17 carbon atoms, more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms.

[0079] Examples of the group represented by the formula (b1-3) include the groups represented by the formulas (b1-9) to (b1-11), respectively. are listed. TIFF2025108538000057.tif23139 [In the formula (b1-9), L b19 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b20 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms, hydroxy groups or alkylcarbonyloxy groups. The -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and the hydrogen atoms contained in the alkylcarbonyloxy group may be substituted with hydroxy groups. However, the total number of carbon atoms of L However, L b19 and L b20 is 23 or less. In the formula (b1-10), L b21represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b22 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 the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms, hydroxy groups or alkylcarbonyloxy groups. In the alkylcarbonyloxy group, -CH2- may be replaced with -O- or -CO-, and the hydrogen atoms contained in the alkylcarbonyloxy group may be substituted with hydroxy groups. However, the total number of carbon atoms of L b21 L b22 and L b23 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 the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. 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 the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms, hydroxy groups or alkylcarbonyloxy groups. In the alkylcarbonyloxy group, -CH2- may be replaced with -O- or -CO-, and the hydrogen atoms contained in the alkylcarbonyloxy group may be substituted with hydroxy groups. However, the total number of carbon atoms of L b24 L b25 and L b26 is 21 or less.

[0080] In the case where the hydrogen atom contained in the saturated hydrocarbon group in the group represented by the formula (b1-9) is substituted with an alkylcarbonyloxy group, the number of carbon atoms before the substitution is defined as the number of carbon atoms of the saturated hydrocarbon group.

[0081] Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, a cyclohexylcarbonyloxy group, an adamantylcarbonyloxy group, etc.

[0082] Examples of the group represented by the formula (b1-4) include the following. TIFF2025108538000058.tif16153

[0083] Examples of the group represented by the formula (b1-5) include the following. TIFF2025108538000059.tif68151

[0084] Examples of the group represented by the formula (b1-6) include the following. TIFF2025108538000060.tif31164

[0085] Examples of the group represented by the formula (b1-7) include the following. TIFF2025108538000061.tif57145

[0086] Examples of the group represented by the formula (b1-8) include the following. TIFF2025108538000062.tif23150

[0087] Examples of the group represented by the formula (b1-2) include the following. JPEG2025108538000063.jpg31161

[0088] ​​ Examples of the group represented by formula (b1-9) include the following. TIFF2025108538000064.tif44137

[0089] Examples of the group represented by formula (b1-10) include the following. TIFF2025108538000065.tif92165

[0090] Examples of the group represented by formula (b1-11) include the following. TIFF2025108538000066.tif84164

[0091] Examples of the alicyclic hydrocarbon group represented by Y include the groups represented by formula (Y1) to formula (Y11), formula (Y36) to the group represented by formula (Y38). When -CH2- contained in the alicyclic hydrocarbon group represented by Y is replaced by -O-, -S(O)2- or - CO-, the number thereof may be one or more than two. Examples of such a group include the groups represented by formula (Y12) to formula (Y35), formula (Y39) to formula (Y43). * represents L and the bonding position to. b1 represents the bonding position to. TIFF2025108538000067.tif83168

[0092] Examples of the alicyclic hydrocarbon group represented by Y preferably include the groups represented by formula (Y1) to formula (Y20), formula ( Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39) to formula (Y43) and more preferably a group represented by any of formula (Y11), formula (Y15), formula (Y16 ), formula (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y 39), 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 ( group represented by formula (Y30), formula (Y31), formula (Y39), formula (Y40), formula (Y42) or formula (Y43) is a group represented by the formula. When the alicyclic hydrocarbon group represented by Y is a spiro ring containing an oxygen atom such as formula (Y28) to formula (Y35), formula (Y39), formula ( Y40), formula (Y42) or formula (Y43), the alkanediyl group between the two oxygen atoms preferably has one or more fluorine atoms. Also among the alkanediyl groups contained in the ketal structure, the methylene group adjacent to the oxygen atom is preferably not substituted with a fluorine atom.

[0093] Examples of the substituent of the methyl group represented by Y include a halogen atom, a hydroxy group, an alicyclic hydrocarbon group having 3 to 1 6 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, a glycidyloxy group, -( CH2) ja -CO-O-R b1 group or -(CH2) ja -O-CO-R b1 group (wherein R b1 represents an alkyl group having 1 to 16 carbon atoms, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms or a group combining these, and -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced by -O-, -SO2- or -CO-, and the 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. ja represents any integer from 0 to 4 ).). Examples thereof include the following. Examples of the substituent of the alicyclic hydrocarbon group represented by Y include a halogen atom, a hydroxy group, an alkyl group having 1 to 16 carbon atoms which may be substituted with a hydroxy group (the alkyl group contains ​​​​​-CH2- may be replaced by -O- or -CO-.), a C3-C16 aliphatic cyclic hydrocarbon group, a C6-C18 aromatic hydrocarbon group, a C7-C21 aralkyl group, a glycidyloxy group, -(CH2) ja -CO-O-R b1 group or -(CH2) ja -O-CO -R b1 group (wherein R b1 represents an alkyl group having 1 to 16 carbon atoms, a C3-C16 alicyclic hydrocarbon group, a C6-C18 aromatic hydrocarbon group or a group combining these, and -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. ja represents , any integer from 0 to 4. etc. may be mentioned.).

[0094] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom etc. are mentioned. 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, an adamantyl group etc. The alicyclic hydrocarbon group may have a chain hydrocarbon group , and examples include a methylcyclohexyl group, a dimethylcyclohexyl group etc. . The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 12, more preferably 3 to 10 . Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a phenanthryl group etc. The aromatic hydrocarbon group may have a chain carbon It may have a hydrogen group or an alicyclic hydrocarbon group, and a chain hydrocarbon group having 1 to 18 carbon atoms Examples of the aromatic hydrocarbon group having include tolyl group, xylyl group, cumenyl group, mesityl group, p- ethylphenyl group, p-tert-butylphenyl group, 2,6-diethylphenyl group, 2 -methyl-6-ethylphenyl group, etc. Examples of the aromatic hydrocarbon group having an alicyclic hydrocarbon group having 3 to 18 carbon atoms include p-cyclohexylphenyl group, p-adamantylphenyl group, etc. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 14, more preferably 6 to 10. Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, b utyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group , 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group , etc. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 9, still 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 hydroxymethyl group and hydroxy ethyl group. Examples of the aralkyl group include benzyl group, phenethyl group, phenylpropyl group, naphthylme thyl group, naphthylethyl group, etc. Examples of the group in which -CH2- contained in the alkyl group is replaced with -O-, -S(O)2- or -CO- etc. include alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, al kylcarbonyloxy group or a group combining these, etc. Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, penti A luoxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group And a dodecyloxy group and the like can be mentioned. The number of carbon atoms in the alkoxy group is preferably 1 to 12 Yes, more preferably 1 to 6, and even more preferably 1 to 4. Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl Group, a butoxycarbonyl group and the like. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group and a butyryl group And the like. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy Group, a butyryloxy group and the like. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of the combined group include a group combining an alkoxy group and an alkyl group, an 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. And the like can be mentioned. Examples of the group combining an alkoxy group and an alkyl group include a methoxymethyl group, A methoxyethyl group, an ethoxyethyl group, an ethoxymethyl group and other alkoxyalkyl groups such as And the like can be mentioned. 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 the group formed by combining an alkoxy group and an alkoxy group include alkoxyalkoxy groups such as methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, and ethoxyethoxy group. 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 formed by combining an alkoxy group and an alkylcarbonyl group include alkoxyalkylcarbonyl groups such as methoxyacetyl group, methoxypropionyl group, ethoxyacetyl group, and ethoxypropionyl group. The number of carbon atoms in the alkoxyalkylcarbonyl group is preferably 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. Examples of the group formed by combining an alkoxy group and an alkylcarbonyloxy group include alkoxyalkylcarbonyloxy groups such as methoxyacetyloxy group, methoxypropionyloxy group, ethoxyacetyloxy group, and ethoxypropionyloxy group. The number of carbon atoms in the alkoxyalkylcarbonyloxy group is preferably 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. Examples of the group in which -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -S(O)2-, -CO-, etc. include the groups represented by formula (Y12) to formula (Y35), formula (Y39) to formula (Y43). Examples of Y include the following. Y is preferably an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent. JPEG2025108538000068.jpg156170

[0095]

[0096] ​​​​​​​​​​, more preferably an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, even more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, even more preferably an adamantyl group which may have a substituent, and the -CH2- constituting the alicyclic hydrocarbon group or adamantyl group may be replaced by -CO-, -S(O)2- or -CO-. Y is specifically preferably an adamantyl group, a hydroxyadamantyl group, an oxoadamantyl group or a group represented by formula (Y42), formula (Y100) to formula (Y114). Specifically, Y is preferably an adamantyl group, a hydroxyadamantyl group, an oxoadamantyl group or a group represented by formula (Y42), formula (Y100) to formula (Y114). The anions in the salt represented by formula (B1) include anions represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter, may be referred to as "anion (B1-A-1)" etc. according to the formula number]. Among them, anions represented by any of formula (B1-A-1) to formula (B1-A-4), formula (B1-A-9), formula (B1-A-10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A-36) to formula (B1-A-40), formula (B1-A-47) to formula (B1-A-59) are more preferable. The anions in the salt represented by formula (B1) include anions represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter, may be referred to as "anion (B1-A-1)" etc. according to the formula number]. Among them, anions represented by any of formula (B1-A-1) to formula (B1-A-4), formula (B1-A-9), formula (B1-A-10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A-36) to formula (B1-A-40), formula (B1-A-47) to formula (B1-A-59) are more preferable.

[0097] The anions in the salt represented by formula (B1) include anions represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter, may be referred to as "anion (B1-A-1)" etc. according to the formula number]. Among them, anions represented by any of formula (B1-A-1) to formula (B1-A-4), formula (B1-A-9), formula (B1-A-10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A-36) to formula (B1-A-40), formula (B1-A-47) to formula (B1-A-59) are more preferable. The anions in the salt represented by formula (B1) include anions represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter, may be referred to as "anion (B1-A-1)" etc. according to the formula number]. Among them, anions represented by any of formula (B1-A-1) to formula (B1-A-4), formula (B1-A-9), formula (B1-A-10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A-36) to formula (B1-A-40), formula (B1-A-47) to formula (B1-A-59) are more preferable. The anions in the salt represented by formula (B1) include anions represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter, may be referred to as "anion (B1-A-1)" etc. according to the formula number]. Among them, anions represented by any of formula (B1-A-1) to formula (B1-A-4), formula (B1-A-9), formula (B1-A-10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A-36) to formula (B1-A-40), formula (B1-A-47) to formula (B1-A-59) are more preferable. The anions in the salt represented by formula (B1) include anions represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter, may be referred to as "anion (B1-A-1)" etc. according to the formula number]. Among them, anions represented by any of formula (B1-A-1) to formula (B1-A-4), formula (B1-A-9), formula (B1-A-10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A-36) to formula (B1-A-40), formula (B1-A-47) to formula (B1-A-59) are more preferable. The anions in the salt represented by formula (B1) include anions represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter, may be referred to as "anion (B1-A-1)" etc. according to the formula number]. Among them, anions represented by any of formula (B1-A-1) to formula (B1-A-4), formula (B1-A-9), formula (B1-A-10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A-36) to formula (B1-A-40), formula (B1-A-47) to formula (B1-A-59) are more preferable. The anions in the salt represented by formula (B1) include anions represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter, may be referred to as "anion (B1-A-1)" etc. according to the formula number]. Among them, anions represented by any of formula (B1-A-1) to formula (B1-A-4), formula (B1-A-9), formula (B1-A-10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A-36) to formula (B1-A-40), formula (B1-A-47) to formula (B1-A-59) are more preferable.

[0098] TIFF2025108538000069.tif111143

[0099] TIFF2025108538000070.tif128167

[0100] TIFF2025108538000071.tif93145

[0101] TIFF2025108538000072.tif137140

[0102] TIFF2025108538000073.tif84163

[0103] JPEG2025108538000074.jpg90150 Here, R i2 ~R i7 is, independently of each other, for example, an alkyl group having 1 to 4 carbon atoms, preferably is a methyl group or an ethyl group. R i8 is, for example, an aliphatic 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. L is a single bond or an alkanediyl group having 1 to 4 carbon atoms A4 is. Q b1 and Q b2 represent the same meaning as described above. As the anion in the salt represented by the formula (B1), specifically, the anions described in JP-A-2010-20 4646 are exemplified.

[0104] Preferred anions in the salt represented by the formula (B1) include anions represented by the formula (B1a-1) to the formula ( B1a-38), respectively. TIFF2025108538000075.tif122158

[0105] TIFF2025108538000076.tif95145

[0106] TIFF2025108538000077.tif167156

[0107] Among them, anions represented by any of the formula (B1a-1) to the formula (B1a-3), the formula (B1a-7) to the formula ( B1a-1 6), the formula (B1a-18), the formula (B1a-19), the formula (B1a-22) to the formula (

[0108] 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. Specifically, cations represented by any of formula (b2-1) to formula (b2-4) (hereinafter, may be referred to as "cation (b2-1)" etc. according to the formula number) are included. TIFF2025108538000078.tif48169In formula (b2-1) to formula (b2-4), R b4 ~R b6 each independently represents a chain hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms, and the hydrogen atoms 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, the hydrogen atoms 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 the hydrogen atoms contained in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxy group, or an alkoxy group having 1 to 12 carbon atoms. R and R may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R and R R b4 and R b5 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. Rb7 and R b8 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. m2 and n2 each independently represent any integer from 0 to 5. When m2 is 2 or more, the plurality of Rs b7 may be the same or different, and when n2 is 2 or more, the plurality of Rs may be the same or different. b8 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 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and the -CH2- contained in the ring may be replaced by -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 the hydrogen atom contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 12 carbon atoms or an alkylcarbonyl oxy 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 the -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. ​ R b13 ~R b18 each independently represents a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. L b31 represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent any integer from 0 to 5. q2 and r2 each independently represent any integer from 0 to 4. u2 represents 0 or 1. When o2 is 2 or more, the plurality of Rs b13 are the same or different; when p2 is 2 or more, the plurality of Rs b14 are the same or different; when q2 is 2 or more, the plurality of Rs b15 are the same or different; when r2 is 2 or more, the plurality of Rs b16 are the same or different; when s2 is 2 or more, the plurality of Rs b17 are the same or different; when t2 is 2 or more, the plurality of Rs b18 are the same or different. The aliphatic hydrocarbon group represents a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of the chain hydrocarbon 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, an octyl group, and an alkyl group such as a 2-ethylhexyl group. In particular, the chain hydrocarbon group of R b9 ~R b12 preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a cyclodecyl group. It is obtained. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group , a norbornyl group, and the following groups. TIFF2025108538000079.tif10159 In particular, R b9 ~R b12 The alicyclic hydrocarbon group is preferably C3-C18, more preferably is C4-C12. Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include methylcyclohe xyl group, dimethylcyclohexyl group, 2-methyladamantan-2-yl group, 2-ethyl adamantan-2-yl group, 2-isopropyladamantan-2-yl group, methylnor bornyl group, 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 of the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 20 or less. Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, biphenylyl group, naphthyl group, phenanthry l group. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group. Examples of the aromatic hydrocarbon group having a chain hydrocarbon group include tolyl group , xylyl group, cumenyl group, mesityl group, p-ethylphenyl group, p-tert-butyl phenyl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc. are mentioned Among them, examples of the aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p -adamantylphenyl group, etc.). When the aromatic hydrocarbon group contains a chain hydrocarbon group or an alicyclic hydrocarbon group, a chain hydrocarbon group having 1 to 18 carbon atoms and a carbon number of 3 ~18 alicyclic hydrocarbon groups are preferred. Examples of the aromatic hydrocarbon group in which a hydrogen atom is substituted with an alkoxy group include p-methoxyphenyl Examples thereof include an Ru group. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as a benzyl group, a phenethyl group, a phenylpropyl group, a trityl group, a naphthylmethyl group, and a naphthylethyl 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 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 b5 The ring formed by their bonding together with the sulfur atom to which they are bonded may be a monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated ring. Examples of this ring include rings having 3 to 18 carbon atoms, preferably 4 to 18 carbon atoms. Further, examples of the ring containing a sulfur atom include 3- to 12-membered rings, preferably 3- to 7-membered rings, and examples thereof include the following rings. * represents the bonding position. TIFF2025108538000080.tif23143Rb9 and R b10 The ring formed by combining with is monocyclic, polycyclic, aromatic, non-aromatic , and may be any of saturated and unsaturated rings. Examples of this ring include 3-membered rings to 12-membered rings , preferably 3-membered rings to 7-membered rings. For example, thiolan-1-ium ring (tetrahydrothi ophenium ring), thian-1-ium ring, 1,4-oxathian-4-ium ring, etc. can be mentioned . R b11 and R b12 The ring formed by combining with is monocyclic, polycyclic, aromatic, non-aromatic , and may be any of saturated and unsaturated rings. Examples of this ring include 3-membered rings to 12-membered rings , preferably 3-membered rings to 7-membered rings. Examples include oxocycloheptane ring, oxocyclohexane ring , oxonorbornane ring, oxoadamantane ring, etc.

[0109] Among cations (b2-1) to (b2-4), preferably, it is cation (b2 -1). Examples of cation (b2-1) include the following cations. TIFF2025108538000081.tif38158

[0110] TIFF2025108538000082.tif140154

[0111] Examples of cation (b2-2) include the following cations. TIFF2025108538000083.tif18150

[0112] Examples of cation (b2-3) include the following cations. TIFF2025108538000084.tif26139

[0113] Examples of cation (b2-4) include the following cations. TIFF2025108538000085.tif85169

[0114] The acid generator (B) is a combination of the above-mentioned anion and the above-mentioned organic cation, and these can be arbitrarily combined. As the acid generator (B), preferably, the anion represented by any of formula (B1a-1) to formula (B1a-3) and formula (B1a-7) to formula (B1a-16), formula (B1a-18), formula (B1a-19), formula (B1a-22) to formula (B1a-38), and the combination with cation (b2-1) or cation (b2-3) can be mentioned.

[0115] As the acid generator (B), preferably, those represented by formula (B1-1) to formula (B1-56) respectively can be mentioned. Among them, those containing an arylsulfonium cation are preferred, and those represented by formula (B1-1) to formula (B1-3), formula (B1-5) to formula (B1-7), formula (B1-11) to formula (B1-14), formula (B1-20) to formula (B1-26), formula (B1-29), formula (B 1-31) to formula (B1-56) are particularly preferred. TIFF2025108538000086.tif119149

[0116] JPEG2025108538000087.jpg77147

[0117] JPEG2025108538000088.jpg147146

[0118] JPEG2025108538000089.jpg64163

[0119] TIFF2025108538000090.tif168168

[0120] <Resin (A)> Resin (A) has 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 the structural unit other than structural unit (a1) include a structural unit having no acid-labile group (hereinafter sometimes referred to as "structural unit (s)"), a structural unit other than structural unit (a1) and structural unit (s) (for example, a structural unit having a halogen atom described later (hereinafter sometimes referred to as "structural unit (a4)"), a structural unit having a non-leaving hydrocarbon group described later (hereinafter sometimes referred to as "structural unit (a5)"), and structural units derived from other monomers known in the art, etc.).

[0121] 〈Structural unit (a1)〉 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 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)). TIFF2025108538000091.tif2397[In formula (1), R a1 , R a2 and R a3 each independently represent an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a combination thereof, or R a1 and R a2 a2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with the carbon atom to which they are bonded. ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * represents a bonding position.] ​​​​​​​​​TIFF2025108538000092.tif2379[In formula (2), R a1’ and R a2’ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 1 2 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 a heterocyclic ring having 3 to 20 carbon atoms together with the carbon atom to which they are bonded and X, and the -CH2- contained in the hydrocarbon group and the heterocyclic ring may be replaced by -O- or -S- . X represents an oxygen atom or a sulfur atom. na’ represents 0 or 1. * represents a bonding position.]

[0122] Examples of the alkyl group in R a1 , R a2 and R a3 include a methyl group, an ethyl group, a prop yl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, etc. The alicyclic hydrocarbon group in R a1 , R a2 and R a3 may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following group (* represents a bonding position.). Examples of the alicyclic hydrocarbon group in R a1 , R a2 and R a3 preferably have 3 to 16 carbon atoms. TIFF2025108538000093.tif10150Examples of the group combining an alkyl group and an alicyclic hydrocarbon group include, for example, methylcyclohe Xylyl group, dimethylcyclohexyl group, methylnorbornil group, cyclohexylmethyl group , adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc. are exemplified . Preferably, ma is 0 and na is 1. R a1 and R a2 are bonded to each other to form a non-aromatic hydrocarbon ring, -C(R a1 )( (R a2 )(R a3 ) includes the following rings. The non-aromatic hydrocarbon ring is preferably having 3 to 12 carbon atoms. * represents the bonding position to -O-. TIFF2025108538000094.tif30139

[0123] R a1’ , R a2’ and R a3’ The hydrocarbon groups in include alkyl groups, alicyclic carbon hydrogen groups, aromatic hydrocarbon groups, and groups formed by combining these, etc. are exemplified . The alkyl group and the alicyclic hydrocarbon group are the same as the groups exemplified for R a1 , R a2 and R a3 . are exemplified. Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group, etc. Examples of the combined group include a group combining the above-mentioned alkyl group and alicyclic hydrocarbon group (for example, cycloalkylalkyl group), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having an alkyl group (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl- 6-ethylphenyl group, etc.), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), an aryl-cycloalkyl group such as phenylcyclohexyl group, etc. and the like. When R and R a2’ are bonded to each other and together with the carbon atom to which they are bonded and X form a heterocycle, -C(R a3’ )(R )(R a1’ )(R a2’ )-X-R a3’ includes the following rings. * represents the bonding position. TIFF2025108538000095.tif19130R It is preferable that at least one of R a1’ and R a2’ is a hydrogen atom. na' is preferably 0.

[0124] Examples of the group (1) include the following groups. In formula (1), when R a1 , R a2 and R a3 are alkyl groups, ma = 0, and n a = 1. A preferred group of this type is the tert-butoxycarbonyl group. In formula (1), when R a1 , R a2 together with the carbon atom to which they are bonded form an adamantyl group, R is an alkyl group, ma = 0, and na = 1. a3 In formula (1), when R and R a1 are each independently an alkyl group, R a2 is an adamantyl group, ma = 0, and na = 1. a3 Examples of the group (1) specifically include the following groups. * represents the bonding position. TIFF2025108538000096.tif78168 TIFF2025108538000096.tif78168

[0125] Specific examples of group (2) include the following groups. * represents the bonding position. TIFF2025108538000097.tif74154

[0126] Monomer (a1) preferably has an acid-labile group and an ethylenically unsaturated bond, more preferably is a (meth)acrylic monomer having an acid-labile group.

[0127] Among the (meth)acrylic monomers having an acid-labile group, preferably those having an alicyclic hydrocarbon group with 5 to 20 carbon atoms are mentioned. Using a resin (A) having a structural unit derived from a monomer (a1) having a bulky structure such as an alicyclic hydrocarbon group in the resist composition can improve the resolution of the resist pattern.

[0128] As the structural unit derived from the (meth)acrylic monomer having group (1), 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)) is mentioned. Preferably, it is at least one structural unit 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. In formulas (a1-0), (a1-1) and (a1-2), L TIFF2025108538000098.tif43145 L a01 L a1 and L a2 are each independently -O- or * -O-(CH2) k1 - represents CO-O-, k1 represents any integer from 1 to 7, and * represents the bonding position with -CO-. That is. R a01 、R a4 and R a5 each independently represents a hydrogen atom or a methyl group. 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, or a group formed by combining these. R a6 and R a7 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or a group formed by combining these. m1 represents any integer from 0 to 14. n1 represents any integer from 0 to 10. n1’ represents any integer from 0 to 3.

[0129] R a01 、R a4 and R a5 are preferably methyl groups. L a01 、L a1 and L a2 are preferably an oxygen atom or *-O-(CH2) k01 -C O-O- (where k01 is preferably any integer from 1 to 4, more preferably 1. ), and more preferably an oxygen atom. R a02 、R a03 、R a04 、R a6 and R a7 The alkyl group, alicyclic hydrocarbon group and the group formed by combining these in a1 、R a2 and R a3 are the same as the groups exemplified by R in formula (1). R a02 、R a03 、and R a04 The alkyl groups in are preferably alkyl groups 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 groups in are preferably alkyl groups having 1 to 6 carbon atoms , more preferably a methyl group, an ethyl group or an isopropyl group, and even more preferably an ethyl group or an isopropyl group. R a02 、R a03 and R a04 The number of carbon atoms of the alicyclic hydrocarbon groups of is preferably 5 to 12, more preferably 5 to 10. The group formed by combining an alkyl group and an alicyclic hydrocarbon group preferably has a total number of carbon atoms of 18 or less when these alkyl groups and alicyclic hydrocarbon groups are combined. R a02 and R a03 are preferably alkyl groups having 1 to 6 carbon atoms, more preferably methyl groups or ethyl groups. R a04 is preferably an alkyl group having 1 to 6 carbon atoms or an alicyclic hydrocarbon group having 5 to 12 carbon atoms, more preferably a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group . R a6 and R a7 are preferably alkyl groups having 1 to 6 carbon atoms, more preferably me thyl groups, ethyl groups or isopropyl groups, and even more preferably ethyl groups or isoprop yl groups. m1 is preferably any integer from 0 to 3, more preferably 0 or 1. n1 is preferably any integer from 0 to 3, more preferably 0 or 1. n1’ is preferably 0 or 1.

[0130] Examples of the structural unit (a1-0) include structural units represented by any of formula (a1-0-1) to formula (a1-0-12) and the methyl group corresponding to R in the structural unit (a1-0) a01 is replaced by a hydrogen atom, and the structural units represented by any of formula (a1-0-1) to formula (a1-0 -10) are preferred. TIFF2025108538000099.tif66158

[0131] Examples of the structural unit (a1-1) include structural units derived from the monomers described in JP-A-2010-204646. Among them, the structural units represented by any of formula (a1-1-1) to formula (a1 -1-4) and the methyl group corresponding to R in the structural unit (a1-1) is preferably replaced by a hydrogen atom, and the structural units represented by any of formula (a1-1-1) to formula ( a4 corresponding a1-1-4) are more preferred. TIFF2025108538000100.tif44114

[0132] Examples of the structural unit (a1-2) include structural units represented by any of formula (a1-2-1) to formula (a1-2-6) and the methyl group corresponding to R in the structural unit (a1-2) a5 is replaced by a hydrogen atom, and the structural units represented by any of formula (a1-2-2), formula (a1-2-5) and formula (a1-2-6) are preferred. TIFF2025108538000101.tif36161

[0133] When the resin (A) contains the structural unit (a1-0), the content thereof is the total structural unit of the resin (A) The amount is usually 5 to 60 mol %, preferably 5 to 50 mol %, more preferably The content is usually 10 to 40 mol %. When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), The total content of these units is usually 10 to 95 mol % based on the total structural units of the resin (A). The content is preferably 15 to 85 mol %, more preferably 15 to 80 mol %, and further preferably Preferably, it is 20 to 80 mol %, and even more preferably, it is 20 to 75 mol %.

[0134] The structural unit (a1) having the group (2) is represented by the formula (a1-4). Examples of the structural unit include a structural unit (hereinafter sometimes referred to as "structural unit (a1-4)"). TIFF2025108538000102.tif3867[In formula (a1-4), R a32 is a hydrogen atom, a halogen atom, or a C1-6 alkyl group which may have a halogen atom represents an alkyl group represented by the formula: R a33 is a halogen atom, a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, Alkoxy groups, alkylcarbonyl groups having 2 to 4 carbon atoms, alkylcarbonyl groups having 2 to 4 carbon atoms It represents an acryloyloxy group, an acryloyloxy group, or a methacryloyloxy group. la represents an integer of 0 to 4. When la is 2 or more, a plurality of R a33 are mutual may be the same or different. 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 combined with each other and forms a divalent hydrocarbon group having 2 to 20 carbon atoms together with -C-O- to which they are bonded, and -CH2- contained in the hydrocarbon group and the divalent hydrocarbon group may be replaced by -O- or -S-.] The alkyl groups for R and R

[0135] include methyl group, ethyl group, propyl group, isopropyl group, butyl group, pentyl group, hexyl group and the like. 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.] a32 and R a33 include fluorine atom, chlorine atom, bromine atom and the like.] Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include trifluoromethyl group, difluoromethyl group, methyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, ethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, butyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, pentyl group, hexyl group, perfluorohexyl group and the like.] Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group and the like. Among them, an alkoxy group having 1 to 4 carbon atoms is preferable, a methoxy group or an ethoxy group is more preferable, and a methoxy group is even more preferable.] The alkyl groups for R a32 and R a33 include fluorine atom, chlorine atom, bromine atom and the like.] Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include trifluoromethyl group, difluoromethyl group, methyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, ethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, butyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, pentyl group, hexyl group, perfluorohexyl group and the like.] Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group and the like. Among them, an alkoxy group having 1 to 4 carbon atoms is preferable, a methoxy group or an ethoxy group is more preferable, and a methoxy group is even more preferable.] Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group and the like. Among them, an alkoxy group having 1 to 4 carbon atoms is preferable, a methoxy group or an ethoxy group is more preferable, and a methoxy group is even more preferable.] ​​​​​​​​​​Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, and the like. R a34 , R a35 and R a36 Examples of the hydrocarbon group in R, R, and R include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group combining these. 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, an octyl group, and the like. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following group (* represents a bonding site), and the like. 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 combining the above-described alkyl group and alicyclic hydrocarbon group (for example, a cycloalkylalkyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl- 6-ethylphenyl group, etc.), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohe Xylylphenyl group, p - adamantylphenyl group, etc.), phenylcyclohexyl group, etc. Aryl - cycloalkyl group and the like can be mentioned. In particular, R a36 As, it is 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 can be mentioned.

[0136] In formula (a1 - 4), R a32 As, a hydrogen atom is preferable. R a33 As, an alkoxy group having 1 to 4 carbon atoms is preferable, a methoxy group and an ethoxy group Are more preferable, and a methoxy group is even more preferable. As la, 0 or 1 is preferable, and 0 is more preferable. R a34 Is preferably a hydrogen atom. R a35 Is preferably an alkyl group or an alicyclic hydrocarbon group having 1 to 12 carbon atoms, and More preferably a methyl group or an ethyl group. R a36 The hydrocarbon group of 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 More preferably, it is an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 1 8 carbon atoms or an aralkyl group having 7 to 18 carbon atoms. The alkyl a36 Group and alicyclic hydrocarbon group in R Are preferably unsubstituted. The aromatic a36 Hydrocarbon group in R Is preferably an aromatic ring having an aryloxy group having 6 to 10 carbon atoms.

[0137] -OC(R a34 )(R a35 ) - O - R a36is eliminated upon contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxy group. Examples of the structural unit (a1-4) include structural units derived from the monomers described in JP-A-2010-204646. Preferably, the structural units represented by formula (a1-4-1) to formula (a1 -4-12) and the structural unit in which the hydrogen atom corresponding to R is replaced with a methyl group are mentioned. More preferably, the structural units represented by formula (a1-4-1) to formula (a1-4- a32 12), formula (a1-4-10) are mentioned. When the resin (A) has the structural unit (a1-4), its content is preferably 5 to 60 mol%, more preferably 5 to 50 mol%, and even more preferably 10 to 40 mol% based on the total of all the structural units of the resin (A). TIFF2025108538000104.tif68157 Examples of the structural unit derived from the (meth)acrylic monomer having the group (2) include the structural unit represented by formula (a1 -5) (hereinafter sometimes referred to as "structural unit (a1-5)"). In formula (a1-5),

[0138] R represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom, or a halogen atom. TIFF2025108538000105.tif4354 In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom, or a halogen atom. Z a1 represents a single bond or *-(CH2) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, and * represents the bonding position to L 51 51 51 L 51 L 52 L 53 and L 54Each independently represents -O- or -S-. s1 represents any integer from 1 to 3. s1’ represents any integer from 0 to 3.

[0139] Examples of the halogen atom include a fluorine atom and a chlorine atom, and a fluorine atom is 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 is preferred. L 51 is preferably an oxygen atom. L 52 and L 53 Among them, it is preferred that one is -O- and the other is -S-. s1 is preferably 1. s1’ is preferably any integer from 0 to 2. Z a1 is preferably a single bond or *-CH2-CO-O-.

[0140] Examples of the structural unit (a1-5) include, for example, the structural units derived from the monomers described in JP-A-2010-61117. Among them, the structural units represented by formula (a1-5-1) to formula (a1-5- 4) are preferred, and the structural units represented by formula (a1-5-1) or formula (a1-5-2 ) are more preferred. When the resin (A) has the structural unit (a1-5), its content is preferably 1 to 50 mol%, more preferably 3 to 45 mol%, and 5 to 40 mol% is more preferred with respect to all the structural units of the resin (A), Mol% is more preferable, and 5 to 30 mol% is even more preferable.

[0141] Examples of the structural unit (a1) include a structural unit represented by the formula (a1-0X) (hereinafter sometimes referred to as the structural unit (a1-0X)). ). TIFF2025108538000107.tif3961[In the formula (a1-0X), R x1 represents a hydrogen atom or a methyl group. R x2 and R x3 each independently represent a saturated hydrocarbon group having 1 to 6 carbon atoms. Ar x1 represents an aromatic hydrocarbon group having 6 to 36 carbon atoms.]

[0142] R x2 and R x3 Examples of the saturated hydrocarbon group include an alkyl group, an alicyclic hydrocarbon group, and a group formed by combining these. ). 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, a pentyl group, a hexyl group, and the like. ). The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. ). Ar x1 Examples of the aromatic hydrocarbon group of Ar include aryl groups having 6 to 36 carbon atoms such as a phenyl group, a naphthyl group, and an anthryl group. ). The aromatic hydrocarbon group preferably has 6 to 24 carbon atoms, more preferably 6 to 1 8 carbon atoms, and even more preferably is a phenyl group. Ar x1 is preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms, and more preferably a ph It is a phenyl group or a naphthyl group, and more preferably a phenyl group. R x1 , R x2 and R x3 are each independently preferably a methyl group or an ethyl group, and more preferably a methyl group.

[0143] Examples of the structural unit (a1-0X) include the structural units described below and compounds in which the methyl group corresponding to R in the structural unit (a1-0X) x1 is replaced by a hydrogen atom. The structural unit (a1-0X) is preferably the structural units (a1-0X-1) to (a1-0X-3). When the resin (A) has the structural unit (a1-0X), its content is preferably 5 to 60 mol% with respect to all the monomers in the resin (A), more preferably 5 to 50 mol%, and even more preferably 10 to 40 mol%. The resin (A) may contain two or more kinds of the structural unit (a1-0X).

[0144] Examples of the structural unit (a1) also include the following structural units. When the resin (A) contains the above structural unit, its content is preferably 5 to 60 mol% with respect to all the structural units of the resin (A), more preferably 5 to 50 mol%, and even more preferably 10 to 40 mol%.

[0145] 〈Structural unit (s)〉 The structural unit (s) is derived from a monomer having no acid-labile group (hereinafter sometimes referred to as "monomer (s)"). The monomer that leads to the structural unit (s) is a publicly known acid-labile monomer in the resist field. Monomers without a stabilizing group can be used. As the structural unit(s), it is preferable to have a hydroxy group or a lactone ring. Hydro A structural unit having a xy group and no acid-labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and no acid-labile group (hereinafter sometimes referred to as "structural unit (a3)") If a resin having is used in the resist composition of the present invention, The resolution of the resist pattern and the adhesion to the substrate can be improved.

[0146] 〈Structural unit (a2)〉 The hydroxy group contained in the structural unit (a2) may be an alcoholic hydroxy group or a phenolic hydroxy group. When producing a resist pattern from the resist composition of the present invention, when using a high-energy ray such as a KrF excimer laser (248 nm), an electron beam, or EUV (extreme ultraviolet light) as the exposure light source, As the structural unit (a2), a structural unit (a2) having a phenolic hydroxy group is preferable, and it is more preferable to use the structural unit (a2-A) described later. Also, When using an ArF excimer laser (193 nm) or the like, as the structural unit (a2), a structural unit (a2) having an alcoholic hydroxy group is preferable, and it is more preferable to use the structural unit (a2 -1) described later. The structural unit (a2) may be contained alone or in combination of two or more. Examples of the structural unit having a phenolic hydroxy group in the structural unit (a2) include a structural unit represented by the formula (a 2-A) (hereinafter sometimes referred to as "structural unit (a2-A)").

[0147] ​​​​​​​​TIFF2025108538000110.tif4551[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 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 represents a single bond or *-X a51 -(A a52 -X a52 ) nb -, where * represents the bonding position to the carbon atom to which -R a50 is bonded. A a52 represents an alkanediyl group having 1 to 6 carbon atoms. X a51 and X a52 each independently represent -O-, -CO-O-, or -O-CO-. nb represents 0 or 1. mb represents any integer from 0 to 4. When mb is an integer of 2 or more, the plural R a51 may be the same as or different from each other.]

[0148] R a50 Examples of the halogen atom in R 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 in R 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 perflu A ruoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, per fluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropent yl group, a pentyl group, a hexyl group, and a perfluorohexyl group may be mentioned. R a50 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 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. are mentioned. R a51 Examples of the alkoxy group in include a methoxy group, an ethoxy group, a propoxy group, iso propoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group. An alkoxy group having 1 to 4 carbon atoms is preferable, a methoxy group or an ethoxy group is more preferable, and a meth oxy group is even more preferable. R a51 Examples of the alkylcarbonyl group in include an acetyl group, a propionyl group, and buty ryl group and the like. R a51 Examples of the alkylcarbonyloxy group in include an acetyloxy group, propiony loxy group, and a butyryloxy group. R a51 is preferably a methyl group.

[0149] *-X a51 -(A a52 -X a52 ) nb As *-O-, *-CO-O-, *-O-C O-, *-CO-O-A a52 -CO-O-, *-O-CO-A a52 -O-, *-O-A a52 -CO-O-, *-CO-O-A a52 -O-CO-, *-O-CO-A a52 -O-CO-, include. Among them, *-CO-O-, *-CO-O-A a52 -CO-O- or *- O-A a52 -CO-O- is preferred. 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 butane-1,3-diyl group, 2-methylpropane-1, 3-diyl group, 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group and a 2-methylbutane-1,4-diyl group and the like. A a52 is preferably a methylene group or an ethylene group. A a50 is a single bond, *-CO-O- or *-CO-O-A a52 -CO-O- is preferred, and 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. mb is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0. The hydroxy group is preferably bonded to the ortho position or the para position of the benzene ring, and more preferably bonded to the para position.

[0150] Examples of the structural unit (a2-A) include structural units derived from the monomers described in JP-A-2010-204634 and JP-A-2012- 12577. As the structural unit (a2-A), those represented by Formula (a2-2-1) to Formula (a2-2-6) structural units and the structural units represented by Formula (a2-2-1) to Formula (a2-2-6) in which the methyl group corresponding to R in the structural unit (a2-A) a50 is replaced by a hydrogen atom structural units are exemplified. The structural unit (a2-A) is the structural unit represented by Formula (a2-2-1), the formula (a2-2-3), the structural unit represented by Formula (a2-2-6), and the formula (a2-2-1), the structural unit represented by Formula (a2-2-3), or the formula (a 2-2-6), in the structural unit represented by, the methyl group corresponding to R in the structural unit (a2-A) a50 corresponding to is preferably a structural unit in which the methyl group is replaced by a hydrogen atom. When the structural unit (a2-A) is contained in the resin (A), the content of the structural unit (a2-A) is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, still more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%, particularly preferably 25 to 55 mol% with respect to all the structural units. The structural unit (a2-A) can be incorporated into the resin (A) by, for example, polymerizing using the structural unit (a1-4) and then treating with an acid such as p-toluenesulfonic acid. Also , after polymerizing using acetoxystyrene or the like, treating with an alkali such as tetramethylammonium hydroxide can incorporate the structural unit (a2-A) into the resin (A).

[0151] As the structural unit having an alcoholic hydroxy group in the structural unit (a2), the formula ​​a2-1) (hereinafter sometimes referred to as "structural unit (a2-1)") Some examples include: TIFF2025108538000112.tif3957 formula (a2-1), L a3 is -O- or * -O-(CH2) k2 represents -CO-O-, k2 represents an integer of any one of 1 to 7. * represents the bonding position 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 of 0 to 10.

[0152] In formula (a2-1), L a3 is preferably -O-, -O-(CH2) f1 -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.

[0153] Examples of the structural unit (a2-1) include those described in JP-A-2010-204646. The structural units derived from the monomers of formula (a2-1-1) to formula (a2-1-6) are included. ), and the structural unit represented by any one of the formulas (a2-1-1) to (a2-1-4) is preferred. A structural unit represented by any one of the formulas (a2-1-1) or (a2-1- The structural unit represented by 3) is more preferred. When the resin (A) contains the structural unit (a2-1), its content is usually 1 to 45 mol%, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, still more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol% with respect to all the structural units of the resin (A).

[0154] 〈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 may be a condensed ring of a monocyclic lactone ring and another ring. Preferably, a γ-butyrolactone ring, an adamantane lactone ring, or a bridged ring containing a γ- butyrolactone ring structure (for example, the structural unit represented by the following formula (a3-2)) is exemplified. The structural unit (a3) is preferably a structural unit represented by the formula (a3-1), the formula (a3-2), the formula (a3-3) or the formula (a3-4). These may be contained alone or in combination of two or more. TIFF2025108538000114.tif51162 [In the formula (a3-1), the formula (a3-2), the formula (a3-3) and the formula (a3-4), L a4 、L a5 and L a6 each independently represents a group represented by -O- or *-O-(CH2) k3 - CO-O- (k3 represents an integer from 1 to 7). L a7 is -O-, *-O-L a8 -O-, *-O-L a8 -CO-O-, *-O-L a8 -CO-O-L a9 -CO-O- or *-O-L a8 ​​​-O-CO-L a9 represents -O-. . L a8 and L a9 each independently represents an alkanediyl group having 1 to 6 carbon atoms. * represents the bonding position to the carbonyl group. R a18 , R a19 and R a20 each independently represents a hydrogen atom or a methyl group. R a24 may be an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or represents 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 a aliphatic hydrocarbon group having 1 to 4 carbon atoms. p1 represents any integer from 0 to 5. q1 represents any integer from 0 to 3. r1 represents any integer from 0 to 3. w1 represents any integer from 0 to 8. When p1, q1, r1 and / or w1 is 2 or more, a plurality of R a21 , R a22 , R a2 3 and / or R a25 may be the same as or different from each other.

[0155] R a21 , R a22 , R a23 and R a25 Examples of the aliphatic hydrocarbon group in include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group and ter t-butyl group. R a24 As the halogen atom in R, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom can be mentioned. R a24 As the alkyl group in R, 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, etc. can be mentioned. Preferably, an alkyl group having 1 to 4 carbon atoms can be mentioned, and more preferably, a methyl group or an ethyl group can be mentioned. R a24 As the alkyl group having a halogen atom in R, a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluoro robutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoro ropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, a triiodomethyl group, etc. can be mentioned.

[0156] L a8 and L a9 As the alkanediyl group in L and L, a methylene group, an ethylene group, a prop ane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pen tane-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 pen tane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group, etc. can be mentioned.

[0157] In formulas (a3-1) to (a3-3), L a4 ~L a6 are each independently preferably -O- or, *-O-(CH2) k3-CO-O-, where k3 is an integer of any one of 1 to 4, more preferably -O- and, *-O-CH2-CO-O-, still 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 are each independently preferably an integer of any one of 0 to 2, more preferably 0 or 1.

[0158] 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, still more preferably a hydrogen atom or a methyl group. R a25 is preferably a carboxy group, a cyano group or a methyl group. L a7 is preferably -O- or *-O-L a8 -CO-O-, more preferably -O-, -O-CH2-CO-O- or -O-C2H4-CO-O-. w1 is preferably an integer of any one of 0 to 2, more preferably 0 or 1. In particular, formula (a3-4) is preferably formula (a3-4)’. TIFF2025108538000115.tif3845 (wherein R a24 , L a7 represent the same meanings as described above.)

[0159] As the structural unit (a3), the monomers described in JP-A-2010-204646, the monomers described in JP-A-2000-122294, JP-A-2012-41274 ​Examples of the structural unit (a3) include structural units derived from the monomers described in the above publication. , formula (a3-1-1), formula (a3-1-2), formula (a3-2-1), formula (a3-2-2) , Formula (a3-3-1), Formula (a3-3-2) and Formula (a3-4-1) to Formula (a3-4-1 2), and in the structural unit, the structural unit represented by any one of the formulas (a3-1) to (a3-2) R in a3-4) a18 , R a19 , R a20 and R a24 The methyl group corresponding to Substituted structural units are preferred. TIFF2025108538000116.tif115165When resin (A) contains structural unit (a3), the total content is the total content of all structural units of resin (A). The amount is usually 1 to 70 mol %, preferably 1 to 65 mol %, more preferably The content is usually 1 to 60 mol %. In addition, the structural unit (a3-1), the structural unit (a3-2), the structural unit (a3-3) or the structural unit The content of the units (a3-4) is 1 to 60 moieties relative to the total structural units of the resin (A). % by mole is preferable, 1 to 50 mol % is more preferable, and 1 to 50 mol % is even more preferable.

[0160] <Structural unit (a4)> Examples of the structural unit (a4) include the following structural units. TIFF2025108538000117.tif3165[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, The -CH2- contained in the group may be replaced with -O- or -CO-. R 42 The saturated hydrocarbon group represented by the formula (I) is a chain hydrocarbon group and a monocyclic or polycyclic alicyclic hydrocarbon group. Groups such as a group, and a group formed by combining these are exemplified.

[0161] Examples of the chain 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, hexa decyl group, a heptadecyl group, and an octadecyl group. Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group; polycyclic alicyclic hydrocarbon groups such as a decahydronaphthyl group, an ada mantyl group, a norbornyl group, and the following group (* represents the bonding position). are exemplified. TIFF2025108538000118.tif10160 Groups formed by combination include groups formed by combining one or more alkyl groups or one or more alkanedi yl groups with one or more alicyclic hydrocarbon groups, and examples include -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, -al kanediyl group-alicyclic hydrocarbon group-alkyl group, etc.

[0162] Examples of the structural unit (a4) include a structural unit represented by at least one selected from the group consisting of formula (a4-0), formula (a4-1), formula (a4-2), formula ( a4-3), and formula (a4-4). are exemplified. TIFF2025108538000119.tif3953 [In formula (a4-0), R 5a represents a hydrogen atom or a methyl group. L 4a represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. L 3a represents a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluoro Represents a luorocycloalkanediyl group. R 6a represents a hydrogen atom or a fluorine atom.

[0163] L 4a Examples of the alkanediyl group in L include linear alkanediyl groups such as methylene group, ethylene group, propane-1, 3-diyl group, butane-1,4-diyl group, and branched alkanediyl groups such as ethane-1,1 -diyl group, propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpro pane-1,3-diyl group, and 2-methylpropane-1,2-diyl group. are included.

[0164] L 3a Examples of the perfluoroalkanediyl group in L include difluoromethylene group, per fluoroethylene group, perfluoropropane-1,1-diyl group, perfluoropropane -1,3-diyl group, perfluoropropane-1,2-diyl group, perfluoropropane -2,2-diyl group, perfluorobutane-1,4-diyl group, perfluorobutane-2 ,2-diyl group, perfluorobutane-1,2-diyl group, perfluoropentane-1, 5-diyl group, perfluoropentane-2,2-diyl group, 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, Examples thereof include a 3-diyl group, a perfluorooctane-4,4-diyl group, and the like. L 3a Examples of the perfluorocycloalkanediyl group in 3a include a perfluorocyclohexane diyl group, a perfluorocyclopentane diyl group, a perfluorocycloheptane di yl group, a perfluoroadamantane diyl group, and the like.

[0165] L 4a is preferably a single bond, a methylene group or an ethylene group, more preferably a single bond or a methylene group. L 3a is preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0166] Examples of the structural unit (a4-0) include the following structural units and the structural units in the following structural units ( a4-0) in which the methyl group corresponding to R 5a in 5a is replaced by a hydrogen atom. TIFF2025108538000120.tif95165

[0167] TIFF2025108538000121.tif5170[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 by -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-g 1). However, at least one of A a41 and R a42 is used as a substituent ​​It has a halogen atom (preferably a fluorine atom). TIFF2025108538000122.tif1383 [In the 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. It represents a saturated hydrocarbon group. A a43 represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. It represents a group. X a41 and X a42 each independently represents -O-, -CO-, -CO-O- or -O-CO -. However, the total number of carbon atoms of A a42 , A a43 , A a44 , X a41 and X a42 is 7 or less.] * is the bonding position, and the * on the right is the bonding position with -O-CO-R a42 .]

[0168] R a42 Examples of the saturated hydrocarbon group in R include a chain saturated hydrocarbon group, a monocyclic or polycyclic alicyclic saturated hydrocarbon group, and a group formed by combining these. etc. are included.

[0169] 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 he xadecyl group, a heptadecyl group and an octadecyl group. Examples of the monocyclic or polycyclic alicyclic saturated hydrocarbon group include a cyclopentyl group, a cyclohexyl group , a cycloheptyl group, a cyclooctyl group and other cycloalkyl groups; a decahydronaphthyl group, Polycyclic alicyclic groups such as adamantyl group, norbornyl group and the following group (* represents the bonding position). Examples of the saturated hydrocarbon group of the formula include those mentioned below. TIFF2025108538000123.tif10160As the group formed by the combination, groups formed by combining one or more alkyl groups or one or more alkanedi yl groups with one or more saturated alicyclic hydrocarbon groups are mentioned, and examples include -alkanediyl group-saturated alicyclic hydrocarbon group, -saturated alicyclic hydrocarbon group-alkyl group, -alkanediyl group-saturated alicyclic hydrocarbon group-alkyl group, and the like.

[0170] R a42 The substituents that R has include at least one selected from the group consisting of a halogen atom and a group represented by the formula (a-g3). Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and preferably a fluorine atom. TIFF2025108538000124.tif752[In the 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 the bonding position with R a42 .] However, in R a42 -X a43 -A a45 when R a42 does not have a halogen atom, A a4 5 represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms which has at least one halogen atom .

[0171] A a45 ​​Examples of the aliphatic hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl; monocyclic alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; and polycyclic alicyclic hydrocarbon groups such as decahydronaphthyl, adamantyl, norbornyl, and the following group (* represents the bonding position). Examples of the group formed by the combination of TIFF2025108538000125.tif10160 include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group - alicyclic hydrocarbon group, - alicyclic hydrocarbon group - alkyl group, - alkanediyl group - alicyclic hydrocarbon group - alkyl group, and the like.

[0172] R a42 is preferably a saturated hydrocarbon group which may have a halogen atom, more preferably an alkyl group having a halogen atom and / or a saturated hydrocarbon group having a group represented by the formula (a-g3). R a42 When R is a saturated hydrocarbon group having a halogen atom, it is preferably a saturated hydrocarbon group having a fluorine atom, more preferably a perfluoroalkyl group or a perfluorochloroalkyl group, still more preferably a perfluoroalkyl group having 1 to 6 carbon atoms, particularly preferably a perfluoroalkyl group having 1 to 3 carbon atoms. Examples of the perfluoroalkyl group include perfluoromethyl, perfluoroethyl, and perfluoropropyl. , perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoro oroheptyl group, perfluorooctyl group and the like. Examples of the perfluorocycloalkyl group include a perfluorocyclohexyl group and the like. R a42 is a saturated hydrocarbon group having a group represented by the formula (a-g3). When including the number of carbon atoms contained in the group represented by the formula (a- g3), the total number of carbon atoms of R a42 is preferably 15 or less, more preferably 12 or less. When having a group represented by the formula (a-g3) as a substituent, the number thereof is preferably 1.

[0173] R a42 is a saturated hydrocarbon group having a group represented by the formula (a-g3), R a42 is more preferably a group represented by the formula (a-g2). [In the formula (a-g2), TIFF2025108538000126.tif874 A a46 represents a divalent saturated hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. X a44 represents **-O-CO- or **-CO-O- (** represents the bonding position with A a46 ).). A a47 represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. . However, the total number of carbon atoms of A a46 , A a47 and X a44 is 18 or less, and at least one of A a46 and A a47 has at least one halogen atom. * represents the bonding position with the carbonyl group.]

[0174] Aa46 The number of carbon atoms in the saturated hydrocarbon group is preferably 1 to 6, more preferably 1 to 3. A a47 The number of carbon atoms in the aliphatic hydrocarbon group is preferably 4 to 15, more preferably 5 to 12, A a47 is more preferably a cyclohexyl group or an adamantyl group.

[0175] The preferred structure of the group represented by formula (a-g2) is the following structure (* is the bonding position with the carbonyl group ). TIFF2025108538000127.tif13161

[0176] A a41 As the alkanediyl group in, methylene group, ethylene group, propane-1, 3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1 ,6-diyl group and other linear alkanediyl groups; propane-1,2-diyl group, butane-1 ,3-diyl group, 2-methylpropane-1,2-diyl group, 1-methylbutane-1,4- diyl group, 2-methylbutane-1,4-diyl group and other branched alkanediyl groups can be mentioned . A a41 As the substituent in the alkanediyl group represented by, hydroxy group and alkoxy group having 1 to 6 carbon atoms and the like can be mentioned. 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.

[0177] In the group represented by formula (a-g1), A a42 , A a43 and A a44 The divalent saturated hydrocarbon group represented by is a linear or branched alkanediyl group and a monocyclic or polycyclic divalent alicyclic hydrocarbon A base, and groups formed by combining an alkanediyl group and a divalent alicyclic hydrocarbon group, etc. are exemplified. Specifically, 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, a 2-methylpropane-1,2-diyl group, etc. are exemplified. and the like. As substituents of the divalent saturated hydrocarbon group represented by A , A and A , a hydroxy group a42 , A a43 and A a44 , and an alkoxy group having 1 to 6 carbon atoms, etc. are exemplified. s is preferably 0.

[0178] In the group represented by formula (a-g1), examples of the group in which X a42 is -O-, -CO-, -CO-O- or -O-CO- include the following groups and the like. In the following examples, * and ** each represent a bonding position, and ** is the bonding position with -O-CO-R a42 . TIFF2025108538000128.tif48153

[0179] Examples of the structural unit represented by formula (a4-1) include the following structural units and the structural units in which the methyl group corresponding to R in the structural unit represented by formula (a4-1) below is replaced by a hydrogen atom. a41 TIFF2025108538000129.tif100142

[0180] TIFF2025108538000130.tif123140

[0181] As the structural unit represented by formula (a4-1), the structural unit represented by formula (a4-2) is preferred. ​ TIFF2025108538000131.tif3354[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 -C H2- in the alkanediyl group may be replaced by -O- or -CO-. R f6 represents a saturated hydrocarbon group having 1 to 20 carbon atoms and having a fluorine atom. However, the upper limit of the total number of carbon atoms of L 44 and R f6 is 21.]

[0182] The alkanediyl group of L 44 includes the same groups as those exemplified by A a41 . R f6 The saturated hydrocarbon group of a42 includes the same groups as those exemplified by R L 44 As the alkanediyl group in, an alkanediyl group having 2 to 4 carbon atoms is preferable , and an ethylene group is more preferable.

[0183] Examples of the structural unit represented by formula (a4-2) include, for example, the structural units represented by formulas (a4-1-1) to (a4 -1-11). In the structural unit (a4-2), R f5 A structural unit in which the methyl group corresponding to is replaced by a hydrogen atom is also included as a structural unit represented by formula (a4-2) .

[0184] TIFF2025108538000132.tif5164[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 f13represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms which may have a fluorine atom. Yes. X f12 is *-O-CO- or *-CO-O- (* represents the bonding position with A f13 .). . A f14 represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom. However, at least one of A f13 and A f14 has a fluorine atom, and the upper limit of the total number of carbon atoms of L 5 , A f13 and A f14 is 20.

[0185] L 5 As the alkanediyl group in, those exemplified as the alkanediyl group of A a41 are mentioned. The same groups can be mentioned. A f13 As the divalent saturated hydrocarbon group which may have a fluorine atom in, preferably is a divalent chain saturated hydrocarbon group which may have a fluorine atom and a divalent alicyclic saturated hydrocarbon group which may have a fluorine atom, more preferably a perfluoroalkanediyl group. As the divalent chain hydrocarbon group which may have a fluorine atom, there are alkanediyl groups such as methylene group, ethylene group, propane - diyl group, butane - diyl group and pentane - diyl group; di fluoromethylene group, perfluoroethylene group, perfluoropropane - diyl group, perfluoro butane - diyl group and perfluoropentane - diyl group and other perfluoroalkanediyl groups. The divalent alicyclic hydrocarbon group which may have a fluorine atom may be either monocyclic or polycyclic. As the monocyclic group, there are cyclohexane - diyl group and perfluorocyclohexane The divalent alicyclic hydrocarbon group which may have a fluorine atom may be either monocyclic or polycyclic. As the monocyclic group, there are cyclohexane - diyl group and perfluorocyclohexane diyl group. Examples of the divalent group include an ethylidyne group. Examples of the polycyclic group include an adamantanediyl group, a norbornanediy l group, and a perfluoroadamantanediyl group.

[0186] A f14 saturated hydrocarbon group and a saturated hydrocarbon group which may have a fluorine atom are the same groups as those exemplified by R a42 and include groups similar to those exemplified. Among them, 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 , a perfluorohexyl group, a heptyl group, a perfluoroheptyl group, an octyl group and a per fluoroalkyl group such as a fluorooctyl group, a cyclopropylmethyl group, a cyclopropyl group , a cyclobutylmethyl group, a cyclopentyl group, a cyclohexyl group, a perfluorocyclohe xyl group, an adamantyl group, an adamantylmethyl group, an adamantyldimethyl group, a norbor nyl group, a norbornylmethyl group, a perfluoroadamantyl group, a perfluoroadamant ylmethyl group and the like are preferable.

[0187] In formula (a4-3), L 5 is preferably an ethylene group. A f13 's divalent saturated hydrocarbon group preferably includes a divalent chain hydrocarbon group having 1 to 6 carbon atoms and a divalent alicyclic hydrocarbon group having 3 to 12 carbon atoms, and a divalent chain hydrocarbon group having 2 to 3 carbon atoms A base is more preferred. A f14 The saturated hydrocarbon group of A preferably includes a chain hydrocarbon group having 3 to 12 carbon atoms and an alicyclic hydrocarbon group having 3 to 12 carbon atoms. A group containing a chain hydrocarbon group having 3 to 10 carbon atoms and an alicyclic hydrocarbon group having 3 to 10 carbon atoms is more preferred. Among them, A is preferably a group containing an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a cyclopropylmethyl f14 group, a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group. group, a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group. group, a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group.

[0188] Examples of the structural unit represented by the formula (a4-3) include structural units represented by the formulas (a4-1’-1) to (a 4-1’-11), respectively. The structural unit in which the methyl group corresponding to R in the structural unit (a4-3) is replaced by a hydrogen atom is also included in the structural units represented by the formula (a4-3). f7 in the structural unit (a4-3) is replaced by a hydrogen atom is also included in the structural units represented by the formula (a4-3). in the structural unit (a4-3) is replaced by a hydrogen atom is also included in the structural units represented by the formula (a4-3).

[0189] Examples of the structural unit (a4) also include a structural unit represented by the formula (a4-4). TIFF2025108538000133.tif4061 [In the formula (a4-4), R f21 represents a hydrogen atom or a methyl group. A f21 represents -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -, or -(CH2) j4 - CO-O-(CH2) j5 -. j1 to j5 each independently represent an integer of 1 to 6. R f22 represents a saturated hydrocarbon group having 1 to 10 carbon atoms having a fluorine atom.

[0190] Rf22 The saturated hydrocarbon group is R a42 Examples of the saturated hydrocarbon group represented by are the same as the saturated hydrocarbon group represented by R R f22 is an alkyl group having 1 to 10 carbon atoms with a fluorine atom or an alicyclic hydrocarbon group having 1 to 10 carbon atoms with a fluorine atom Preferably, it is an alkyl group having 1 to 10 carbon atoms with a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms with a fluorine atom, and even more preferably an alkyl group having 1 to 6 carbon atoms with a fluorine atom In formula (a4-4), as A -(CH2) f21 is preferable, an ethylene group or a methylene group is more preferable, and a methylene group is even more preferable j1 group or a methylene group is more preferable, and a methylene group is even more preferable group or a methylene group is more preferable, and a methylene group is even more preferable

[0191] Examples of the structural unit represented by formula (a4-4) include the following structural units and the following structural units in which the methyl group corresponding to R in structural unit (a4-4) is replaced with a hydrogen atom f21 in the structural unit (a4-4) corresponding to R Examples of the structural unit include the structural unit in which the methyl group corresponding to R in the structural unit (a4-4) is replaced with a hydrogen atom When the resin (A) has the structural unit (a4), its content is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and even more preferably 3 to 10 mol% based on all the structural units of the resin (A) % is even more preferable

[0192] 〈Structural unit (a5)〉 Examples of the non-leaving hydrocarbon group of the structural unit (a5) include a group having a linear, branched or cyclic hydrocarbon group. Among them, the structural unit (a5) preferably has an alicyclic hydrocarbon group group is preferable Examples of the structural unit (a5) include the structural unit represented by formula (a5-1) . TIFF2025108538000135.tif3972 [In formula (a5-1), R 51represents a hydrogen atom or a methyl group. R 52 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and the hydrogen atoms contained in the alicyclic hydrocarbon group may be substituted with aliphatic hydrocarbon groups 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 by -O- or -CO-.

[0193] R 52 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopent yl group, and a cyclohexyl group. Examples of the polycyclic alicyclic hydrocarbon group include , an adamantyl group, a norbornyl group, and the like. Examples of the aliphatic hydrocarbon group having 1 to 8 carbon atoms include an alkyl group such as a methyl group, an ethyl group, a propyl group, an iso propyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, and a 2-ethylhexyl group. Examples of the alicyclic hydrocarbon group having a substituent include a 3-methyladamantyl group and the like. R 52 is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, more preferably an adamantyl group, a norbornyl group, or a cyclohexyl group.

[0194] L 55 Examples of the divalent saturated hydrocarbon group in include a divalent chain saturated hydrocarbon group and a divalent alicyclic saturated hydrocarbon group, and preferably a divalent chain saturated hydrocarbon group. Examples of the divalent chain saturated hydrocarbon group include a methylene group, an ethylene group, a propane dii Examples of the alkanediyl group include an alkyl group, a butanediyl group, and a pentanediyl group. The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. The monocyclic alicyclic saturated hydrocarbon group includes cycloalkanediyl groups such as a cyclopentanediyl group and a cyclohexanediyl group. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include an adamantandiy group and a norbornanediyl group.

[0195] L 55 Examples of the group in which -CH2- contained in the divalent saturated hydrocarbon group represented by L is replaced with -O- or -CO- include groups represented by formula (L1-1) to formula (L1-4). In the following formulas, * and ** represent bonding positions, and * represents the bonding position with an oxygen atom. TIFF2025108538000136.tif18165 In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents the bonding position with L x1 ). 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, the total number of carbon atoms of L x1 and L x2 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, the total number of carbon atoms of L x3 and L x4 is 17 or less. In formula (L1-3), L x5represents 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. hydrogen group. However, the total number of carbon atoms of L x5 , L x6 and L x7 is 15 or less. In formula (L1-4), L x8 and L x9 each 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, the total number of carbon atoms of L x8 , L x9 and W x1 is 15 or less.

[0196] 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 x7is 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.

[0197] Examples of the group represented by the formula (L1-1) include the following divalent groups. TIFF2025108538000137.tif55134

[0198] Examples of the group represented by the formula (L1-2) include the following divalent groups. TIFF2025108538000138.tif24131

[0199] Examples of the group represented by the formula (L1-3) include the following divalent groups. TIFF2025108538000139.tif15145

[0200] Examples of the group represented by the formula (L1-4) include the following divalent groups. TIFF2025108538000140.tif26114L 55 is preferably a single bond or a group represented by the formula (L1-1).

[0201] Examples of the structural unit (a5-1) include the following structural units and the structural units in the following structural units ( a5-1) where the methyl group corresponding to R 51 is replaced by a hydrogen atom. is obtained. When the resin (A) has the structural unit (a5), its content is preferably 1 to 30 mol%, more preferably 2 to 20 mol%, and still more preferably 3 to 15 mol% based on all the structural units of the resin (A). % is more preferable.

[0202] <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 a structural unit having a sulfonate group or a carboxylate group and an organic cation in the side chain or a structural unit having a sulfonio group and an organic anion in the side chain. is preferably used. Specifically, the structural unit having a sulfonate group or a carboxylate group in the side chain is preferably a structural unit represented by the formula (II-2-A').

[0203] In the formula (II-2-A'), X represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the saturated hydrocarbon group may be replaced by -O-, -S- or -CO-. The 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. TIFF2025108538000142.tif36104 X III3 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the saturated hydrocarbon group may be replaced by -O-, -S- or -CO-. The 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 represents an alkanediyl group having 1 to 8 carbon atoms, and the hydrogen atom contained in the alkanediyl group may be replaced by a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. A x1 represents an alkanediyl group having 1 to 8 carbon atoms, and the hydrogen atom contained in the alkanediyl group may be replaced by a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. RA- represents a sulfonate group or a carboxylate group. R III3 is 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.

[0204] R III3 Examples of the halogen atom represented by R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R III3 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R include the same as those of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R. a8 A x1 Examples of the alkanediyl group having 1 to 8 carbon atoms represented by A 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, a 2-methylbutane-1,4-diyl group, and the like. A x1 Examples of the perfluoroalkyl group having 1 to 6 carbon atoms which may be substituted on A include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, a perfluorohexyl group, and the like. X​​​​​​​​​​​​​​III3 Examples of the divalent saturated hydrocarbon group having 1 to 18 carbon atoms represented by the formula include linear or branched alkanediyl groups, and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups, and these may be combined. 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, dodecane- 1,12-diyl group and other linear alkanediyl groups; butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane- 1,4-diyl group, 2-methylbutane-1,4-diyl group and other branched alkanediyl groups; cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane- 1,4-diyl group, cyclooctane-1,5-diyl group and other cycloalkanediyl groups; norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane- 1,5-diyl group, adamantane-2,6-diyl group and other divalent polycyclic alicyclic saturated hydrocarbon groups, etc. Examples of those in which -CH2- contained in the saturated hydrocarbon group is replaced by -O-, -S- or -CO- include divalent groups represented by formula (X1) to formula (X53). However, the carbon number before -CH2- contained in the saturated hydrocarbon group is replaced by -O-, -S- or -CO- is 17 or less respectively. In the following formula, * and ** represent bonding positions, and * represents the bonding position with A x1 represents the bonding position with A. TIFF2025108538000143.tif145161

[0205] 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.

[0206] ZA in formula (II-2-A') + is the same as the cation Z1 in the acid generator (B1) + and the like can be mentioned. of which can be mentioned.

[0207] The structural unit represented by formula (II-2-A') is preferably the structural unit represented by formula (II-2-A) . TIFF2025108538000144.tif38109[In formula (II-2-A), R III3 , X III3 and ZA + represent the same meaning as above. z2A represents any integer from 0 to 6. R III2 and R III4 each independently represent a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, and when z2A is 2 or more, a plurality of R and R III2 and R III4 may be the same as or different from each other. Q a and Q beach independently represents a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms . R III2 、R III4 、Q a and Q b as the perfluoroalkyl group having 1 to 6 carbon atoms represented by is the same as the perfluoroalkyl group having 1 to 6 carbon atoms represented by the aforementioned Q b1 . Examples thereof include .

[0208] The structural unit represented by formula (II-2-A) is preferably the structural unit represented by formula (II-2-A-1). . TIFF2025108538000145.tif5578[In formula (II-2-A-1), R III2 、R III3 、R III4 、Q a 、Q b and ZA + have the same meanings as described above. R III5 represents a saturated hydrocarbon group having 1 to 12 carbon atoms. z2A1 represents any integer from 0 to 6. X I2 represents a divalent saturated hydrocarbon group having 1 to 11 carbon atoms, and -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 or a hydroxy group.] R III5 Examples of the saturated hydrocarbon group having 1 to 12 carbon atoms represented by include methyl group, ethyl group, prop yl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pent yl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group and dode cyl group and other linear or branched alkyl groups. X I2Examples of the divalent saturated hydrocarbon group represented by X III3 include the same divalent saturated hydrocarbon groups as those represented by .

[0209] As the structural unit represented by formula (II-2-A-1), the structural unit represented by formula (II-2-A-2) is more preferable. TIFF2025108538000146.tif5287 [In formula (II-2-A-2), R III3 and R III5 and ZA + have the same meanings as described above. m and n each independently represent 1 or 2. ]

[0210] Examples of the structural unit represented by formula (II-2-A') include, for example, the following structural units, where a group corresponding to the methyl group of R III3 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, etc.) and the like, and the structural units described in International Publication No. 2012 / 050015. ZA represents an organic cation. + TIFF2025108538000147.tif85163

[0211] The structural unit having a sulfonio group and an organic anion in the side chain is preferably the structural unit represented by formula (II-1-1). TIFF2025108538000148.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 II3each independently represents a hydrocarbon group having 1 to 18 carbon atoms, R II2 and R II3 may combine with 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 R include a phenylene group and a naphthylene group. R II2 and R II3 Examples of the hydrocarbon group represented by include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these. R II4 Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R II4 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R are the same as those of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R a8 A II1 Examples of the divalent linking group represented by include a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O-, -S-, or -CO-. Specifically, the same as those of the divalent saturated hydrocarbon group having 1 to 18 carbon atoms represented by X III3

[0212] Examples of the structural unit containing the cation in formula (II-1-1) include the structural units represented below and R II4 ​​​​​​Groups corresponding to the methyl group include a hydrogen atom, a fluorine atom, a trifluoromethyl group, etc. Examples thereof include structural units in which the group is replaced. JPEG2025108538000149.jpg85130

[0213] A - Examples of the organic anion represented by A include a sulfonate anion, a sulfonylimide anion, a sulfonylmethide anion, a carboxylate anion, and the like. A - The organic anion represented by A is preferably a sulfonate anion, and more preferably an anion contained in the salt represented by the aforementioned formula (B1).

[0214] A - Examples of the sulfonylimide anion represented by A include the following. TIFF2025108538000150.tif38135

[0215] Examples of the sulfonylmethide anion include the following. TIFF2025108538000151.tif29123

[0216] Examples of the carboxylate anion include the following. TIFF2025108538000152.tif39136

[0217] Examples of the structural unit represented by the formula (II-1-1) include structural units represented by the following. and the like. TIFF2025108538000153.tif99155When the resin (A) contains the structural unit (II), the content of the structural unit (II) is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and still more preferably 3 to 10 mol% based on all the structural units of the resin (A).

[0218] Resin (A) may have structural units other than the above-described structural units, and examples of such structural units include structural units well-known in the art.

[0219] Resin (A) is preferably a resin composed of structural unit (a1) and structural unit (s). . Structural unit (a1) is preferably at least one selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2) (preferably the structural unit having a cyclohexyl group and a cyclopentyl group), more preferably at least two kinds. Structural unit (s) is preferably at least one selected from the group consisting of structural unit (a2) and structural unit (a3). Structural unit (a2) is preferably a structural unit represented by formula (a2-A) or a structural unit represented by formula (a2-1). Structural unit (a3) is preferably at least one selected from the group consisting of a structural unit represented by formula (a3-1), a structural unit represented by formula (a3-2), and a structural unit represented by formula (a3-4).

[0220] Each structural unit constituting resin (A) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using monomers that lead to these structural units. The content ratio of each structural unit possessed by resin (A) can be adjusted by the amount of monomers used in the polymerization. The weight average molecular weight of resin (A) is preferably 2,000 or more (more preferably 2,500 or more, still more preferably 3,000 or more), 50,000 or less (more preferably 30,000 or less, still more preferably 15,000 or less). In this specification, the weight average molecular weight... ​​​​​​​​​​​​​ The molecular weight is the value determined under the conditions described in the examples by gel permeation chromatography. It is as follows.

[0221] <Resin other than resin (A)> The resist composition of the present invention may be used in combination with a resin other than resin (A). Examples of the resin other than resin (A) include resins containing structural unit (a4) or structural unit (a5) (hereinafter sometimes referred to as resin (X)). Among them, a resin containing structural unit (a4) is preferable as resin (X). In resin (X), the content of structural unit (a4) is preferably 30 mol% or more, more preferably 40 mol% or more, with respect to the total of all structural units of resin (X), and even more preferably 45 mol% or more. Examples of the structural units that resin (X) may further have include structural unit (a2), structural unit (a3), and structural units derived from other known monomers. Among them, resin ( X) is preferably a resin composed of only structural unit (a4) and / or structural unit (a5), and more preferably a resin composed of only structural unit (a4). Each structural unit constituting resin (X) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using the monomers that induce these structural units. The content of each structural unit of resin (X) can be adjusted by the amount of monomers used in the polymerization. The weight average molecular weight of resin (X) is preferably 6,000 or more (more preferably 7,00 0 or more), and 80,000 or less (more preferably 60,000 or less). The means for measuring the weight average molecular weight of resin (X) is the same as that for resin (A). 0 or more), and 80,000 or less (more preferably 60,000 or less). 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 weight average molecular weight of resin (X) is the same as that of resin (A). When the resist composition contains resin (X), its content is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, more preferably 1 to 40 parts by mass, particularly preferably 1 to 30 parts by mass, and particularly preferably 1 to 8 parts by mass, based on 100 parts by mass of resin (A).

[0222] The content of resin (A) in the resist composition is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, based on the solid content of the resist composition. When the resist composition contains a resin other than resin (A), the total content of resin (A) and the resin other than resin (A) is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, based on the solid content of the resist composition. The solid content of the resist composition and the content of the resin relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0223] <Solvent (E)> The content of solvent (E) in the resist composition is usually 90% by mass or more and 99.9% by mass or less, preferably 92% by mass or more and 99% by mass or less, more preferably 94% by mass or more and 99% by mass or less. The content of solvent (E) can be measured by known analytical means such as liquid chromatography or gas chromatography. Examples of solvent (E) include glycol ether esters such as ethyl cellosolve acetate, methyl cellosolve acetate, and propylene glycol monomethyl ether acetate; glycol ethers such as propylene glycol monomethyl ether; ethyl lactate, acetic acid ​​​​​​​​​​​Esters such as butyl acid, amyl acetate, and ethyl pyruvate; Acetone, methyl isobutyl Ketones such as ketone, 2-heptanone, and cyclohexanone; Cyclic esters such as γ-butyrolactone; etc. can be mentioned. One kind of the solvent (E) may be used alone, or two or more kinds may be used.

[0224] <Quencher (C)> The quencher (C) is a basic nitrogen-containing organic compound or an acid generated from the acid generator (B) Salts that generate an acid with a lower acidity than (however, carboxylate salts represented by formula (I) are excluded). When the resist composition contains a quencher (C), the content of the quencher (C ) is preferably about 0.01 to 15% by mass based on the solid content of the resist composition, more preferably about 0.1 to 10% by mass, still more preferably about 0.1 to 5% by mass and even more preferably about 0.1 to 3% by mass. . Examples of the basic nitrogen-containing organic compound include amines and ammonium salts. Amines include aliphatic amines and aromatic amines. Examples of aliphatic amines include primary amines, secondary amines, and tertiary amines. Examples of amines include 1-naphthylamine, 2-naphthylamine, aniline, diisopropi lylaniline, 2-, 3- or 4-methylaniline, 4-nitroaniline, N-methylani line, N,N-dimethylaniline, diphenylamine, hexylamine, heptylamine , octylamine, nonylamine, decylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine Minn, triethylamine, trimethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, methyldibutylamine, methyldipentylamine , methyldihexylamine, methyldicyclohexylamine, methyldiheptylamine, methyldioctylamine, methyldinonylamine, methyldidecylamine, ethyldibut ylamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine , ethyldioctylamine, ethyldinonylamine, ethyldidecylamine, dicyclohe xylmethylamine, tris[2-(2-methoxyethoxy)ethyl]amine, triiso propanolamine, ethylenediamine, tetramethylenediamine, hexamethylenedia mine, 4,4'-diamino-1,2-diphenylethane, 4,4'-diamino-3,3' -dimethyl diphenylmethane, 4,4'-diamino-3,3'-diethyldiphenylmeth ane, 2,2'-methylenebisaniline, imidazole, 4-methylimidazole, pyridi ne, 4-methylpyridine, 1,2-di(2-pyridyl)ethane, 1,2-di(4-pyridi yl)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 disulf ide, 2,2'-dipyridylamine, 2,2'-dipicolylamine, bipyridine and the like can be cited, preferably aromatic amines such as diisopropyl aniline can be cited, and more preferably 2,6-diisopropyl aniline can be cited. Examples of the ammonium salt include tetramethylammonium hydroxide, tetraisopropyl ammonium hydroxide, tetrabutylammonium hydroxide, tetrahexyl ammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethyl ammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium hydroxide, tetra-n-butylammonium salicylate, choline, and the like.

[0225] The acidity of a salt that generates an acid with a lower acidity than the acid generated from the acid generator (B) 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 (B) is a salt having an acid dissociation constant of the acid generated from the salt usually of -3 < pKa, preferably a salt of -1 < pKa < 7, and more preferably a salt of 0 < pKa < 5. Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator (B) 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-2011-3 9502, and JP-A-2011-191745. As the salt that generates an acid with a lower acidity than the acid generated from the acid generator (B), preferably, a salt that generates a carboxylic acid with a lower acidity than the acid generated from the acid generator (B) (a salt having a carboxylic acid anion ), and more preferably, the weak acid inner salt (D). TIFF2025108538000154.tif85165

[0226] ​​Examples of the intramolecular salt (D) of a weak acid include the following salts. TIFF2025108538000155.tif72165

[0227] <Other Components> The resist composition of the present invention may, if necessary, contain components other than the above-described components (hereinafter sometimes 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, dyes, etc. can be used. are not particularly limited, and additives known in the resist field, such as sensitizers, dissolution inhibitors, surfactants, stabilizers, dyes, etc. can be used. are not particularly limited, and additives known in the resist field, such as sensitizers, dissolution inhibitors, surfactants, stabilizers, dyes, etc. can be used. agents, dyes, etc. can be used.

[0228] <Preparation of Resist Composition> The resist composition of the present invention can be prepared by mixing a carboxylate (I), a resin (A), an acid generator (B), and, if necessary, a resin other than the resin (A), a solvent (E), a quencher (C), and other components (F). The mixing order is arbitrary and is not particularly limited. The temperature during mixing can be appropriately selected from 10 to 40 °C according to the type of resin, etc. and the solubility of the resin, etc. in the solvent (E). The mixing time can be appropriately selected from 0.5 to 24 hours according to the mixing temperature. In addition, the mixing means is not particularly limited, and stirring and mixing, etc. can be used. and, if necessary, a resin other than the resin (A), a solvent (E), a quencher (C), and other components (F). The mixing order is arbitrary and is not particularly limited. The temperature during mixing can be appropriately selected from 10 to 40 °C according to the type of resin, etc. and the solubility of the resin, etc. in the solvent (E). The mixing time can be appropriately selected from 0.5 to 24 hours according to the mixing temperature. In addition, the mixing means is not particularly limited, and stirring and mixing, etc. can be used. is not particularly limited, and the mixing order is arbitrary. The temperature during mixing can be appropriately selected from 10 to 40 °C according to the type of resin and the solubility of the resin in the solvent (E). The mixing time can be appropriately selected from 0.5 to 24 hours according to the mixing temperature. The mixing means is not particularly limited, and stirring and mixing can be used. is not particularly limited, and the mixing order is arbitrary. The temperature during mixing can be appropriately selected from 10 to 40 °C according to the type of resin and the solubility of the resin in the solvent (E). The mixing time can be appropriately selected from 0.5 to 24 hours according to the mixing temperature. The mixing means is not particularly limited, and stirring and mixing can be used. After mixing the respective components, it is preferable to filter using a filter having a pore size of about 0.003 to 0.2 μm. After mixing the respective components, it is preferable to filter using a filter having a pore size of about 0.003 to 0.2 μm. After mixing the respective components, it is preferable to filter using a filter having a pore size of about 0.003 to 0.2 μm. After mixing the respective components, it is preferable to filter using a filter having a pore size of about 0.003 to 0.2 μm. After mixing the respective components, it is preferable to filter using a filter having a pore size of about 0.003 to 0.2 μm.

[0229] <Method for Producing Resist Pattern> The method for producing a resist pattern of the present invention includes (1) a step of applying the resist composition of the present invention onto a substrate, (2) a step of drying the applied composition to form a composition layer, (3) a step of exposing the composition layer, (4) A step of heating the composition layer after exposure, and (5) A step of developing the composition layer after heating. To apply the resist composition onto a substrate, it can usually be carried out by using an apparatus such as a spin coater. Examples of the substrate include inorganic substrates such as silicon wafers. Before applying the resist composition, the substrate may be cleaned, or an antireflection film or the like may be formed on the substrate. By drying the applied composition, the solvent is removed to form a composition layer. Drying can be performed, for example, by evaporating the solvent using a heating device such as a hot plate (so-called prebake). Or it can be carried out using a decompression device. The heating temperature is preferably 50 to 200 °C, and the heating time is preferably 10 to 180 seconds. Also, the pressure during decompression drying is preferably about 1 to 1.0×10 5 Pa. The obtained composition layer is usually exposed using an exposure machine. The exposure machine may be a liquid immersion exposure machine. As the exposure light source, those that emit ultraviolet laser light such as KrF excimer laser (wavelength 248 nm), ArF excimer laser (wavelength 193 nm), F2 excimer laser (wavelength 157 nm), those that convert laser light from a solid laser light source (such as YAG or semiconductor laser) into harmonic laser light in the far ultraviolet region or vacuum ultraviolet region and emit it, those that irradiate electron beams, extreme ultraviolet light (EUV), etc., various ones can be used. In this specification, irradiating these radiations may be collectively referred to as "exposure" in some cases. During exposure, usually, exposure is carried out through a mask corresponding to the required pattern. When the exposure light source is an electron beam, exposure may be carried out by direct drawing without using a mask. The composition layer after exposure is heat-treated (so-called soft post-exposure bake) to promote the deprotection reaction at the acid-labile group. The heating temperature is usually about 50 to 200 °C, preferably about 70 to 150 °C. The heated composition layer is usually developed using a developer with a developing apparatus. Examples of the developing method include dip method, paddle method, spray method, dynamic dispense method, etc. The developing temperature is preferably, for example, 5 to 60 °C, and the developing 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 manufactured. When manufacturing a positive resist pattern from the resist composition of the present invention, an alkali developer is used as the developer. The alkali developer may be various alkaline aqueous solutions used in this field. For example, aqueous solutions of tetramethylammonium hydroxide and (2-hydroxyethyl)trimethylammonium hydroxide (commonly known as choline) can be mentioned. The alkali developer may contain a surfactant. After development, it is preferable to wash the resist pattern with ultrapure water and then remove the water remaining on the substrate and the pattern. When manufacturing a negative resist pattern from the resist composition of the present invention, a developer containing an organic solvent (hereinafter sometimes referred to as an "organic-based developer") is used as the developer. Examples of the organic solvent contained in the organic-based developer include ketone solvents such as 2-hexanone and 2-heptanone; glycol ether acetate solvents such as propylene glycol monomethyl ether acetate; ester solvents such as butyl acetate; propylene glycol monomethyl ether, etc. glycol ether solvents; amide solvents such as N,N-dimethylacetamide; anisole and the like aromatic hydrocarbon solvents. In the organic developer, the content of the organic solvent is preferably 90% by mass or more and 100% by mass or less, The content is preferably from 95% by mass to 100% by mass, and more preferably substantially only an organic solvent. More preferred. Among them, organic developers include those containing butyl acetate and / or 2-heptanone. In the organic developer, the total content of butyl acetate and 2-heptanone is preferably 50% by mass. Preferably, the content is 90% by mass or more and 100% by mass or less, more preferably 90% by mass or more and 100% by mass or less. It is even more preferable that the components are qualitatively only butyl acetate and / or 2-heptanone. The organic developer may contain a surfactant. The water content may be less than 10%. During development, development is stopped by replacing the organic developer with a different type of solvent. Good too. It is preferable to wash the resist pattern after development with a rinse solution. There are no particular limitations as long as the solvent does not dissolve the resist pattern, and any solvent containing a general organic solvent may be used. Any suitable solvent may be used, preferably an alcohol or ester solvent. After cleaning, it is preferable to remove any rinsing liquid remaining on the substrate and the pattern.

[0230] <Application> The resist composition of the present invention is a resist composition for exposure to a KrF excimer laser, Resist composition for exposure to ximer laser, resist composition for exposure to electron beam (EB) or EU A resist composition for V exposure, particularly a resist composition for electron beam (EB) exposure or EUV exposure The composition is suitable as a resist composition for semiconductor microfabrication.

Example

[0231] The present invention will be further specifically described by way of examples. In the examples, the content or usage amount indicated by “%” and “parts” are based on mass unless otherwise specified. The weight average molecular weight is a value determined by gel permeation chromatography. The analysis conditions for gel permeation chromatography are as follows. Column: TSKgel Multipore HXL-M x 3 + guard column (manufactured by Tosoh Corporation) Eluent: Tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI detector Column temperature: 40 °C Injection volume: 100 μl Molecular weight standard: Standard polystyrene (manufactured by Tosoh Corporation) The structure of the compound was confirmed by measuring the molecular ion peak using mass spectrometry (LC is Agilent 1100 type, MASS is Agil ent LC / MSD type). In the following examples, the value of this molecular ion peak is indicated by “MASS”.

[0232] Example 1: Synthesis of the salt represented by formula (IA-31) 4.72 parts of the salt represented by formula (IA-31-a), 5 .10 parts of the salt represented by formula (IA-31-b), 30 parts of dimethylformamide and 0.69 part of potassium carbonate were mixed and stirred at 120 °C for 4 hours, and then cooled to 23 °C. To the obtained reaction mixture, 60 parts of chloroform and 30 parts of ion-exchanged water were added, and the mixture was stirred at 23 °C for 30 minutes, and then separated to extract the organic layer. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23 °C for 30 minutes. The organic layer was then separated and washed with water eight times. The concentrated residue was then column-eluted (Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical The compound was extracted from the eluent (manufactured by Epson Corporation, developing solvent: chloroform / methanol = 1 / 1) to obtain the compound of the formula ( 0.48 parts of the salt represented by formula (IA-31) were obtained. MASS(ESI(+)Spectrum):M 2+ 288.0(M / 2) MASS(ESI(-)Spectrum):M - 193.1

[0233] Example 2: Synthesis of salt represented by formula (IB-2) TIFF2025108538000157.tif68157 4.72 parts of a salt represented by formula (IA-31-a), 2 parts of a salt represented by formula (IA-31-b) 0.55 parts of dimethylformamide, 30 parts of potassium carbonate, and 1.38 parts of potassium carbonate were mixed and heated to 120°C. The mixture was stirred at 4° C. for 4 hours and then cooled to 23° C. The reaction mixture was added with 60 mL of chloroform. Add 30 parts of ethyl acetate and 30 parts of ion-exchanged water, stir at 23°C for 30 minutes, and then separate the organic layer. To the recovered organic layer, 30 parts of ion-exchanged water was added and stirred at 23° C. for 30 minutes. The organic layer was then separated and washed with water eight times. The concentrated residue was then column-eluted (Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical The compound was extracted from the eluent (manufactured by Epson Corporation, developing solvent: chloroform / methanol = 1 / 1) to obtain the compound of the formula ( 0.79 parts of the salt represented by the formula IB-2) was obtained. MASS(ESI(+)Spectrum):M 3+ 278.4(M / 3) MASS(ESI(-)Spectrum):M - 193.1

[0234] Example 3: Synthesis of the salt represented by formula (IA-33) 6.16 parts of the salt represented by formula (IA-33-a), 6 .54 parts of the salt represented by formula (IA-33-b), 30 parts of dimethylformamide, and 0.69 part of potassium carbonate were mixed and stirred at 120 °C for 4 hours, and then cooled to 23 °C. To the resulting reaction mixture, 60 parts of chloroform and 30 parts of ion-exchanged water were added, and the mixture was stirred at 23 °C for 30 minutes, and then separated to obtain the organic layer . 30 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 °C for 30 minutes , and then separated to obtain the organic layer. This washing operation was repeated 8 times. The obtained organic layer was concentrated , and the concentrated residue was fractionated by column (silica gel 60N (spherical, neutral), 100 - 210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1) to obtain 0.51 part of the salt represented by formula ( IA-33). MASS(ESI(+)Spectrum): M 288.0 (M / 2) 2+ MASS(ESI(-)Spectrum): M 337.1 -

[0235] Example 4: Synthesis of the salt represented by formula (IB-4) 6.16 parts of the salt represented by formula (IA-33-a), 3 .27 parts of the salt represented by formula (IA-33-b), 30 parts of dimethylformamide, and 1.38 parts of potassium carbonate were mixed and stirred at 120 °C for 4 hours, and then cooled to 23 °C. To the resulting reaction mixture, 60 parts of chloroform and 30 parts of ion-exchanged water were added, and the mixture was stirred at 23 °C for 30 minutes, and then separated to obtain the organic layer . 30 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 °C for 30 minutes Subsequently, liquid separation was performed to extract the organic layer. This washing operation with water was repeated 8 times. The obtained organic layer was concentrated and the concentrated residue was fractionated by column (silica gel 60N (spherical, neutral) 100 - 210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1), to obtain 0.88 part of the salt represented by the formula ( IB-4). MASS(ESI(+)Spectrum): M 3+ 278.4 (M / 3) MASS(ESI(-)Spectrum): M - 337.1

[0236] Example 5: Synthesis of the salt represented by the formula (IA-201) A solution prepared by mixing 4.49 parts of pyridine, 14.67 parts of the compound represented by the formula (IA-201-b), and 25 parts of tetrahydrofuran was added dropwise at 0 °C to a solution prepared by mixing 1 0 parts of the compound represented by the formula (IA-201-a) and 10 parts of tetrahydrofuran. The resulting mixture was stirred at 23 °C for 1 hour. 30 parts of ion-exchanged water was added to the reaction mixture solution, and extraction was performed with ethyl acetate . The extracted organic layer was concentrated under reduced pressure, and then n-heptane was added and stirring was carried out for 1 hour . The mixed solution was allowed to stand, the supernatant was removed, and drying was performed to obtain 22.91 parts of the salt represented by the formula (IA-201-c ). After adding 2.50 parts of the salt represented by the formula (IA-201-c), 50 parts of chloroform, and 12.50 parts of ion-exchanged water, the mixture was stirred at 23 °C for 30 minutes. After adding 1.29 parts of the salt represented by the formula (IA -201-d) to the obtained mixture, the mixture was stirred at 23 °C for 3 hours, followed by liquid separation to extract the organic layer. 20 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 °C for 30 minutes ​​After stirring for a minute, liquid separation was carried out to take out the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the obtained concentrate, and after stirring at 23 °C for 30 minutes, the supernatant was removed and dried to obtain 3.08 parts of the salt represented by the formula (IA-20 1-e). 2.50 parts of the salt represented by the formula (IA-201-c), 50 parts of chloroform and 12.50 parts of ion-exchanged water were added, and then stirred at 23 °C for 30 minutes. To the obtained mixture, 1.44 parts of the salt represented by the formula (IA -201-f) was added, and then stirred at 23 °C for 3 hours, followed by liquid separation to take out the organic layer. 20 parts of ion-exchanged water was added to the recovered organic layer, and after stirring at 23 °C for 30 minutes, liquid separation was carried out to take out the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the obtained concentrate, and after stirring at 23 °C for 30 minutes, the supernatant was removed and dried to obtain 3.12 parts of the salt represented by the formula (IA-20 1-g). 1.01 part of the salt represented by the formula (IA-201-e), 1.06 part of the salt represented by the formula (IA-201-g), 30 parts of dimethylformamide and 0.09 part of potassium carbonate were mixed and stirred at 12 0 °C for 4 hours and then cooled to 23 °C. 60 parts of chloroform and 30 parts of ion-exchanged water were added to the obtained reaction mixture, and after stirring at 23 °C for 30 minutes, liquid separation was carried out to take out the organic layer. 30 parts of ion-exchanged water was added to the recovered organic layer, and after stirring at 23 °C for 30 minutes, liquid separation was carried out to take out the organic layer. This water washing operation was repeated 8 times. The obtained organic layer ​​​​​​​Concentrate and fractionate the concentrated residue using a column (silica gel 60N (spherical, neutral), 100 - 210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1) to obtain 1.18 parts of the salt represented by formula (IA - 201). manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1) to obtain 1.18 parts of the salt represented by formula (IA - 201). 1.18 parts of the salt represented by formula (IA - 201) was obtained. MASS(ESI(+)Spectrum): M 2+ 288.0 (M / 2) MASS(ESI(-)Spectrum): M - 531.1

[0237] Example 6: Synthesis of the salt represented by formula (IB - 128) 1.01 parts of the salt represented by formula (IA - 201 - e), 0.53 parts of the salt represented by formula (IA - 201 - g), 30 parts of dimethylformamide, and 0.17 parts of potassium carbonate were mixed and stirred at 120 °C for 4 hours, then cooled to 23 °C. To the resulting reaction mixture, 60 parts of chloroform and 30 parts of ion - exchanged water were added and stirred at 23 °C for 30 minutes, then the layers were separated and the organic layer was taken out. To the recovered organic layer, 30 parts of ion - exchanged water was added and stirred at 23 °C for 30 minutes, then the layers were separated and the organic layer was taken out. This water - washing operation was repeated 8 times. The obtained organic layer was concentrated, and the concentrated residue was fractionated using a column (silica gel 60N (spherical, neutral), 100 - 210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1) to obtain 1.04 parts of the salt represented by formula (IB - 128). 1.01 parts of the salt represented by formula (IA - 201 - e), 0.53 parts of the salt represented by formula (IA - 201 - g), 30 parts of dimethylformamide, and 0.17 parts of potassium carbonate were mixed and stirred at 12 After stirring at 0 °C for 4 hours, it was cooled to 23 °C. To the resulting reaction mixture, chloroform 60 parts and ion - exchanged water 30 parts were added and stirred at 23 °C for 30 minutes, then the layers were separated and the organic layer was taken out. To the recovered organic layer, 30 parts of ion - exchanged water was added and stirred at 23 °C for 30 minutes then the layers were separated and the organic layer was taken out. This water - washing operation was repeated 8 times. The obtained organic layer was concentrated, and the concentrated residue was fractionated using a column (silica gel 60N (spherical, neutral), 100 - 210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1) to obtain 1.04 parts of the salt represented by formula (IB - 128). manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1) to obtain 1.04 parts of the salt represented by formula (IB - 128). 1.04 parts of the salt represented by formula (IB - 128) was obtained. MASS(ESI(+)Spectrum): M 3+ 278.4 (M / 3) MASS(ESI(-)Spectrum): M - 531.1

[0238] Example 7: Synthesis of the salt represented by formula (IA - 256) 7.54 parts of the salt represented by formula (IA-256-a), 6.50 parts of the salt represented by formula (IA-256-b), 30 parts of dimethylformamide and 0.69 part of potassium carbonate were mixed and stirred at 12 0 °C for 4 hours, and then cooled to 23 °C. To the resulting reaction mixture, 60 parts of chloroform and 30 parts of ion-exchanged water were added, and the mixture was stirred at 23 °C for 30 minutes, and then separated to extract the organic layer. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23 °C for 30 minutes, and then separated to extract the organic layer. This washing operation was repeated 8 times. The obtained organic layer was concentrated, and the concentrated residue was fractionated by a column (silica gel 60N (spherical, neutral), 100 - 210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1) to obtain 1.48 parts of the salt represented by formula (IA-256). MASS(ESI(+)Spectrum): M 2+ 355.0 (M / 2) MASS(ESI(-)Spectrum): M - 337.1

[0239] Example 8: Synthesis of the salt represented by formula (IB-172) 7.54 parts of the salt represented by formula (IA-256-a), 3.25 parts of the salt represented by formula (IA-256-b), 30 parts of dimethylformamide and 1.38 parts of potassium carbonate were mixed and stirred at 12 0 °C for 4 hours, and then cooled to 23 °C. To the resulting reaction mixture, 60 parts of chloroform and 30 parts of ion-exchanged water were added, and the mixture was stirred at 23 °C for 30 minutes, and then separated to extract the organic layer. To the recovered organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23 °C for 30 minutes, and then separated to extract the organic layer. This washing operation was repeated 8 times. The obtained organic layer ​ Concentrate it, and fractionate the concentrated residue through a column (silica gel 60N (spherical, neutral), 100 - 210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: chloroform / methanol = 1 / 1) to obtain 1.59 parts of the salt represented by formula (IB - 172). MASS(ESI(+)Spectrum): M 3+ 369.0 (M / 3) MASS(ESI(-)Spectrum): M - 337.1

[0240] Synthesis of Resin The compounds (monomers) used for the synthesis of resin (A) are shown below. Hereinafter, these compounds are referred to as "monomer (a1 - 1 - 3)" etc. according to their formula numbers. TIFF2025108538000167.tif3896

[0241] Synthesis Example 1 [Synthesis of Resin A1] As monomers, monomer (a1 - 4 - 2), monomer (a1 - 1 - 3) and monomer (a1 - 2 - 6) were used and mixed so that their molar ratio [monomer (a1 - 4 - 2): monomer (a1 - 1 - 3): monomer (a1 - 2 - 6)] was 38:24:38. Further, 1.5 mass times of methyl isobutyl ketone was mixed with this monomer mixture based on the total mass of all monomers. To the obtained mixture, azobisisobutyronitrile was added as an initiator so that it was 7 mol% based on the total number of moles of all monomers, and this was heated at 85°C for about 5 hours to carry out polymerization. Thereafter, an aqueous solution of p - toluenesulfonic acid was added to the polymerization reaction solution, stirred for 6 hours, and then separated. The obtained organic layer was poured into a large amount of n - heptane to precipitate the resin, and the resin was filtered and recovered to obtain a weight - average molecular weight of about 5.3×10 3 ​​​​​​​Resin A1 (copolymer) was obtained with a yield of 78%. This resin A1 has the following structural units and is as follows. TIFF2025108538000168.tif28125

[0242] Synthesis Example 2 [Synthesis of Resin A2] As monomers, monomer (a1-4-2) and monomer (a1-2-6) were used, and their molar ratio [monomer (a1-4-2): monomer (a1-2-6)] was mixed so as to be 38:62. Further, to this monomer mixture, 1.5 times the mass of methyl isobutyl ketone was mixed with respect to the total mass of all monomers. To the obtained mixture, azobisisobutyronitrile was added as an initiator so as to be 7 mol% with respect to the total number of moles of all monomers, and this was heated at 85 °C for about 5 hours to carry out polymerization. Thereafter, an aqueous solution of p-toluenesulfonic acid was added to the polymerization reaction solution, and after stirring for 6 hours, liquid separation was carried out. The obtained organic layer was poured into a large amount of n-heptane to precipitate the resin, and the resin was filtered and recovered, whereby a resin A2 (copolymer) having a weight average molecular weight of about 5.4×10 was obtained with a yield of 89%. This resin A2 has the following structural units. 3 TIFF2025108538000169.tif2887

[0243] <Preparation of Resist Composition> As shown in Table 3, the following components were mixed, and the obtained mixture was filtered through a fluororesin filter having a pore size of 0.2 μm to prepare a resist composition.

[0244]

Table 3

[0245] ​<Resin> A1, A2: Resin A1, Resin A2 <Acid generator (B)> B1-25: Salt represented by formula (B1-25); described in JP-A-2011-126869 Synthesized by the method of TIFF2025108538000171.tif2667<Carboxylate (I)> IA-31: Salt represented by formula (IA-31) IB-2: Salt represented by formula (IB-2) IA-33: Salt represented by formula (IA-33) IB-4: Salt represented by formula (IB-4) IA-201: Salt represented by formula (IA-201) IB-128: Salt represented by formula (IB-128) IA-256: Salt represented by formula (IA-256) IB-172: Salt represented by formula (IB-172) <Quencher (C)> IX-1 IX-2 IX-3 TIFF2025108538000172.tif72108<Solvent> Propylene glycol monomethyl ether acetate 400 parts Propylene glycol monomethyl ether 100 parts γ-Butyrolactone 5 parts

[0246] (Electron beam exposure evaluation of resist composition) A 6-inch silicon wafer was treated on a direct hot plate with hexamethyldisilazane at 90 °C for 60 seconds. The resist composition was spin-coated on this silicon wafer so that the film thickness of the composition layer became 0.04 μm. Then, it was prebaked on a direct hot plate at the temperature shown in the "PB" column of Table 3 for 60 seconds to form a composition layer. On the composition layer formed on the wafer an electron beam lithography machine ["HL-800D" manufactured by Hitachi, Ltd.] was used to perform electron beam drawing on the composition layer formed on the wafer formed on the wafer. Using "50 keV", the exposure dose was gradually changed to directly draw a line and space pattern. After exposure, post-exposure bake was performed on a hot plate at the temperature shown in the "PEB" column of Table 3 for 60 seconds, and further paddle development was performed with a 2.38 mass% aqueous solution of tetramethylammonium hydroxide for 60 seconds to obtain a resist pattern. After exposure, post-exposure bake was carried out on a hot plate at the temperature shown in the "PEB" column of Table 3 for 60 seconds, and further paddle development was performed with a 2.38 mass% aqueous solution of tetramethylammonium hydroxide for 60 seconds to obtain a resist pattern. After exposure, post-exposure bake was carried out on a hot plate at the temperature shown in the "PEB" column of Table 3 for 60 seconds, and further paddle development was performed with a 2.38 mass% aqueous solution of tetramethylammonium hydroxide for 60 seconds to obtain a resist pattern. After exposure, post-exposure bake was carried out on a hot plate at the temperature shown in the "PEB" column of Table 3 for 60 seconds, and further paddle development was performed with a 2.38 mass% aqueous solution of tetramethylammonium hydroxide for 60 seconds to obtain a resist pattern. The obtained resist pattern (line and space pattern) was observed with a scanning electron microscope, and the exposure dose at which the line width and space width of the 60 nm line and space pattern became 1:1 was defined as the effective sensitivity. The obtained resist pattern (line and space pattern) was observed with a scanning electron microscope, and the exposure dose at which the line width and space width of the 60 nm line and space pattern became 1:1 was defined as the effective sensitivity. The obtained resist pattern (line and space pattern) was observed with a scanning electron microscope, and the exposure dose at which the line width and space width of the 60 nm line and space pattern became 1:1 was defined as the effective sensitivity.

[0247] Line Edge Roughness Evaluation (LER): The amplitude of the unevenness on the side surface of the resist pattern manufactured with the effective sensitivity was measured with a scanning electron microscope to obtain the line edge roughness. The results are shown in Table 4. Line Edge Roughness Evaluation (LER): The amplitude of the unevenness on the side surface of the resist pattern manufactured with the effective sensitivity was measured with a scanning electron microscope to obtain the line edge roughness. The results are shown in Table 4. Line Edge Roughness Evaluation (LER): The amplitude of the unevenness on the side surface of the resist pattern manufactured with the effective sensitivity was measured with a scanning electron microscope to obtain the line edge roughness. The results are shown in Table 4.

Table 4

Industrial Applicability

[0248] The carboxylate salt of the present invention and the resist composition containing the carboxylate salt have good line edge roughness and are useful for semiconductor microfabrication. The carboxylate salt of the present invention and the resist composition containing the carboxylate salt have good line edge roughness and are useful for semiconductor microfabrication.

Claims

1. A carboxylic acid generator containing a carboxylate represented by formula (IA) or formula (IB), An acid generator other than the carboxylic acid generator, A resist composition containing a structural unit having an acid-labile group and a resin containing a structural unit represented by formula (a2-A). [In formula (IA) and formula (IB), R １ , R ２ , R ３ and R ４ each independently represent a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH ２ - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO ２ -. R １ and R ２ , and R ３ and R ４ may each be bonded to each other to form a ring having 3 to 24 carbon atoms together with the sulfur atom to which they are bonded, and -CH 2 - in the ring may be replaced by -O-, -S- or -CO-. R ５ 、 R ６ 、 R ７ 、 R ８ and R ９ each independently represents a halogen atom, a hydroxy group, a C1-C6 perfluoroalkyl group or a C1-C12 alkyl group, and the -CH ２ - contained in the alkyl group may be replaced by -O- or -CO-. m5 represents any integer from 0 to 4, and when m5 is 2 or more, the plurality of Rs ５ may be the same as or different from each other. m6 represents any integer from 0 to 4, and when m6 is 2 or more, the plurality of Rs ６ may be the same as or different from each other. m7 represents any integer from 0 to 4, and when m7 is 2 or more, the plurality of Rs ７ may be the same as or different from each other. m8 represents any integer from 0 to 4, and when m8 is 2 or more, the plurality of Rs ８ may be the same as or different from each other. X １ and X ２ each independently represents a single bond, an oxygen atom, a sulfur atom or an alkanediyl group having 1 to 6 carbon atoms, and the -CH ２ - included in the alkanediyl group may be replaced by -O- or -CO-. X ０１ , X ０２ and X ０３ each independently represents an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (wherein -CH ２ - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO ２ -); a group combining an alicyclic hydrocarbon group having 3 to 24 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms (wherein -CH ２ - in the alicyclic hydrocarbon group and the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO ２ - and the alicyclic hydrocarbon group and the chain hydrocarbon group may have a substituent); an aromatic hydrocarbon group having 6 to 24 carbon atoms which may have a substituent; or a group combining an aromatic hydrocarbon group having 6 to 24 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms (wherein -CH ２ - in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO ２ - and the aromatic hydrocarbon group and the chain hydrocarbon group may have a substituent).] [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 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 represents a single bond or *-X a51 -(A a52 -X a52 ) nｂ -, where * represents the bonding position with the carbon atom to which -R a50 is bonded. A a52 represents an alkanediyl group having 1 to 6 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 any integer of 2 or more, a plurality of Rs a51 may be the same as or different from each other.]

2. R １ 、 R ２ 、 R ３ and R ４ The resist composition according to claim 1, wherein R １ 、 R ２ 、 R ３ and R ４ are each independently a phenyl group which may have a substituent.

3. X ０１ , X ０２ and X ０３ is each independently an alicyclic hydrocarbon group which may have a fluorine atom or a hydroxy group (in the alicyclic hydrocarbon group, -CH 2 - may be replaced by -O- or -CO-.), a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group (in the alicyclic hydrocarbon group and the chain hydrocarbon group, -CH 2 - may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom or a hydroxy group.), or an aromatic hydrocarbon group which may have a fluorine atom or a hydroxy group. The resist composition according to claim 1 or 2.

4. The resist composition according to any one of claims 1 to 3, wherein the resin contains at least one selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2). [In formula (a1-1) and formula (a1-2), L a1 and L a2 each independently represents -O- or *-O-(CH ２ ) k1 -CO-O-, k1 represents an integer from 1 to 7, and * represents the bonding position with -CO-. R a4 and R a5 each independently represents a hydrogen atom or a methyl group. R a6 and R a7 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or a group 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. ]

5. (1) A step of applying the resist composition according to any one of claims 1 to 4 onto a substrate, (2) A step of drying the applied composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the exposed composition layer, and (5) A step of developing the heated composition layer, A method for manufacturing a resist pattern, comprising:

Images