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

Abstract

To provide a salt which allows a resist pattern having good CD uniformity (CDU) to be produced, an acid generator, a resin, and a resist composition containing the same.SOLUTION: There are provided: an acid generator containing a salt represented by formula (I); and a resist composition containing the same. [In the formula, R1-R3 each represent a hydroxy group or the like; R4-R9 each represent a halogen atom, a haloalkyl group or the like; R10 represents an acid-labile group; A1-A3 each represent a hydrocarbon group; Qb1 and Qb2 each represent a hydrogen atom, a fluorine atom or the like; Lb1 represents a saturated hydrocarbon group; and L10 represents a single bond or a hydrocarbon group.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a salt, an acid generator, a resin, a resist composition, and a method for producing a resist pattern. [Background technology]

[0002] Patent Document 1 describes a resist composition containing a resin that includes a structural unit derived from a salt represented by the following formula: TIFF2023143845000001.tif2879 [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2011-38092 Summary of the Invention [Problem to be solved by the invention]

[0004] The present invention provides a salt that forms a resist pattern with better CD uniformity (CDU) than a resist pattern formed with the above resist composition. [Means for solving the problem]

[0005] The present invention includes the following inventions. [1] An acid generator containing a salt represented by formula (I) or a structural unit represented by formula (IP). TIFF2023143845000002.tif178148 [In formula (I) and formula (IP), R 1 , R 2 and R 3 each independently represents a hydroxy group, -OR 10 , -O-CO-OR 10 or -OL 1 -CO-OR 10 Represents. L 1represents an alkanediyl group having 1 to 6 carbon atoms. R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group optionally having a substituent, and -CH2- contained in the haloalkyl group and the hydrocarbon group optionally being replaced by -O-, -CO-, -S-, or -SO2-. R 10 represents an acid labile group. A 1 , A 2 and A 3 each independently represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. m1 represents an integer of 0 to 5, and when m1 is 2 or greater, the groups in the parentheses may be the same or different. m2 represents an integer of 0 to 4, and when m2 is 2 or greater, the groups in the parentheses may be the same or different. m3 represents an integer of 0 to 4, and when m3 is 2 or greater, the groups in the parentheses may be the same or different. m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R 4 may be the same or different from each other. m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R 5 may be the same or different from each other. m6 represents an integer of 0 to 4, and when m6 is 2 or more, a plurality of R 6 may be the same or different from each other. m7 represents an integer of 0 to 5, and when m7 is 2 or more, a plurality of R 7 may be the same or different from each other. m8 represents an integer of 0 to 4, and when m8 is 2 or more, a plurality of R 8 may be the same or different from each other. m9 represents an integer of 0 to 4, and when m9 is 2 or more, a plurality of R 9 may be the same or different from each other. However, 0≦m1+m7≦5, 0≦m2+m8≦4, 0≦m3+m9≦4, At least one of m1, m2, and m3 represents an integer of 1 or more. X 4 represents a single bond, -CH2-, -O-, -S-, -CO-, -SO- or -SO2-. Q b1 and Q b2 each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L b1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, wherein -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and wherein a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y b1 represents a single bond or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. R bb1 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X 10 represents a single bond, *-O-**, *-CO-O-**, *-O-CO-O-** or *-Ax-Ph-Ay-**. Ph represents a phenylene group which may have a substituent. Ax represents one bond selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. Ay represents one bond selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. * and ** represent binding sites, * represents R bb1 represents the bonding site with the carbon atom to which it is attached. L 10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-.] [2]A 1 But, ***-X 01 -L 01 -or***-L 01 -X 01 - and A 2 But, ***-X 02 -L 02 -or***-L 02 -X 02 - and A 3 But, ***-X 03 -L 03 -or***-L 03 -X 03 - and X 01 , X 02 and X 03 each independently represents -O-, -CO-, -S- or -SO2-; L 01 , L 02 and L 03 each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-; *** represents R 1 , R 2 or R 3 represents a bonding site with the benzene ring to which the compound is bonded. [3]X 01 , X 02 and X 03 are each independently -O- or -S-. [4]L 01 , L 02 and L 03are each independently a single bond or an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-). [5]R 1 , R 2 and R 3 each independently represents a hydroxy group, -OR 10 or -OL 1 -CO-OR 10 The acid generator according to any one of [1] to [4], wherein [6]R 10 The acid generator according to any one of [1] to [5], wherein the acid labile group is a group represented by formula (1a) or a group represented by formula (2a). TIFF2023143845000003.tif2157 [In formula (1a), R aa1 , R aa2 and R aa3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms. * denotes a binding site.] TIFF2023143845000004.tif2161 [In formula (2a), R aa1’ and R aa2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R aa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa2’ and R aa3’ are bonded to each other and they combine -CX a Together with -, they form a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced with -O- or -S-. X a represents an oxygen atom or a sulfur atom. * denotes a binding site.] [7]Y b1is a single bond or an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-). [8]Y b1 is a cyclohexanediyl group, an adamantanediyl group, a norbornanediyl group, an adamantanelactonediyl group, or a norbornanelactonediyl group. [9]X 10 is a single bond or a group of the formula (X 10 -1)~Formula(X 10 The acid generator according to any one of [1] to [8], wherein the acid generator is a group represented by any one of the following groups: TIFF2023143845000005.tif45170[Formula(X 10 -1)~Formula(X 10 -10) Medium, *, ** are binding sites, * is R bb1 represents the bonding site with the carbon atom to which it is attached. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer between 0 and 4.

[10] X 10 is a single bond or a group of the formula (X 10 -1), formula (X 10 -5') and formula (X 10 -6'). TIFF2023143845000006.tif4252[Formula(X 10 -1), formula (X 10 -5') and formula (X 10 -6') medium, *, ** are binding sites, * is R bb1 represents the bonding site with the carbon atom to which it is attached.]

[11] L 10is a single bond, an alkanediyl group having 1 to 6 carbon atoms (provided that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and that -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-), or a group formed by combining an alkanediyl group having 1 to 6 carbon atoms with a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-, and that -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-).

[12] A resist composition containing the acid generator according to any one of [1] to

[11] .

[13] A salt represented by formula (I), and a resin containing a structural unit (a1) having an acid labile group.

[14] A resin containing a structural unit represented by formula (IP), The resist composition according to

[12] , wherein the resin comprising the structural unit represented by formula (IP) further comprises a structural unit (a1) having an acid labile group.

[15] The resist composition according to

[14] , further comprising a salt represented by formula (I).

[16] The resist composition according to any one of

[13] to

[15] , wherein the structural unit (a1) having an acid labile group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), and a structural unit represented by formula (a1-2): TIFF2023143845000007.tif44144 [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or -O-(CH2) k1 represents —CO—O—, k1 represents an integer of 1 to 7, and * represents the bonding site with —CO—. R a01 , R a4 and R a5 each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. R a6 and R a7 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these. m1' represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1' represents an integer of 0 to 3.

[17] The resist composition according to any one of

[13] to

[16] , wherein the resin containing the structural unit (a1) having an acid labile group further contains a structural unit represented by formula (a2-A). TIFF2023143845000008.tif4653[In formula (a2-A), R a50 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a50 is a single bond or *-X a51 -(A a52 -X a52 ) nb - represents -R a50 represents the bonding site with the carbon atom to which it is bonded. A a52 represents an alkanediyl group having 1 to 8 carbon atoms. X a51 and X a52 each independently represents -O-, -CO-O- or -O-CO-. nb represents 0 or 1. mb represents an integer of 0 to 4. When mb is an integer of 2 or more, a plurality of R a51 may be the same or different from each other.

[18] The resist composition according to any one of

[12] to

[17] , further comprising a salt represented by formula (B1): TIFF2023143845000009.tif2958[In formula (B1), Q b1 and Q b2 each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L b1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, wherein -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and wherein a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y represents an optionally substituted methyl group or an optionally substituted alicyclic hydrocarbon group having 3 to 24 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-. Z + represents an organic cation.

[19] The resist composition according to any one of

[12] to

[18] , further comprising a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator.

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

[12] to

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

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

[22] A 1 But, ***-X 01 -L 01 -or***-L 01 -X 01 - and A 2 But, ***-X 02 -L 02 -or***-L 02 -X 02 - and A 3 But, ***-X 03 -L 03 -or***-L 03 -X 03 - and X 01 , X 02 and X 03 each independently represents -O-, -CO-, -S- or -SO2-; L 01 , L 02 and L 03 each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-; *** represents R 1 , R 2 or R 3 represents a bonding site with the benzene ring to which it is bonded.

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

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

[25] R 1 , R 2 and R 3each independently represents a hydroxy group, -OR 10 or -OL 1 -CO-OR 10 The salt according to any one of

[21] to

[24] , wherein

[26] R 10 The salt according to any one of

[21] to

[25] , wherein the acid labile group is a group represented by the above formula (1a) or a group represented by the above formula (2a).

[27] Y b1 is a single bond or an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-).

[28] Y b1 is a cyclohexanediyl group, an adamantanediyl group, a norbornanediyl group, an adamantanelactonediyl group, or a norbornanelactonediyl group.

[29] X 10 is a single bond or the above formula (X 10 -1)~Formula(X 10 The salt according to any one of

[21] to

[28] , wherein the salt is a group represented by any one of

[21] to

[28] .

[30] X 10 is a single bond or the above formula (X 10 -1), formula (X 10 -5') and formula (X 10 -6').

[31] L 10is a single bond, an alkanediyl group having 1 to 6 carbon atoms (provided that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and that -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-), or a group formed by combining an alkanediyl group having 1 to 6 carbon atoms with a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-, and that -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-).

[32] A resin comprising a structural unit represented by the above formula (IP). [Effects of the Invention]

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

[0007] In this specification, "(meth)acrylic monomer" means "at least one of an acrylic monomer and a methacrylic monomer." The terms "(meth)acrylate" and "(meth)acrylic acid" have the same meaning. Among the groups described in this specification, those that can have both a linear structure and a branched structure may have either. A "combined group" means a group in which two or more of the exemplified groups are combined by appropriately changing their valence, bonding form, etc. "Derived from" or "derived from" means that a polymerizable C=C bond contained in the molecule becomes a -CC- group (single bond) by polymerization. When stereoisomers exist, all stereoisomers are included. In this specification, the term "solids content of a resist composition" refers to the sum of all components in the resist composition excluding the solvent (E), which will be described later.

[0008] <Salt represented by formula (I)> The present invention relates to a salt represented by formula (I) (hereinafter sometimes referred to as "salt (I)"). In the salt (I), the side with a positive charge is sometimes called the "cation (I)" and the side with a negative charge is sometimes called the "anion (I)."

[0009] [Cation (I)] The cation (I) of the salt represented by formula (I) is a cation represented by formula (IC). TIFF2023143845000010.tif80104 [In formula (IC), all symbols have the same meaning as in formula (I)]

[0010] R 1 , R 2 and R 3 L included in 1 Examples of the alkanediyl group in the formula (I) include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and Examples of branched alkanediyl groups include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. L 1 is preferably an alkanediyl group having 1 to 3 carbon atoms, and more preferably a methylene group.

[0011] R 1 , R 2 and R 3 R included in 10 The acid labile group in R 10 When a leaving group including a group represented by the following formula is eliminated, it forms a carboxy group or a hydroxy group. The acid labile group is preferably a group represented by formula (1a) (hereinafter sometimes referred to as "acid labile group (1a)") or a group represented by formula (2a) (hereinafter sometimes referred to as "acid labile group (2a)"). TIFF2023143845000011.tif2157 [In formula (1a), R aa1 , R aa2 and R aa3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms. * denotes a binding site.] TIFF2023143845000012.tif2161[In formula (2a), R aa1’ and R aa2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R aa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa2’ and R aa3’ are bonded to each other and they combine -CX a Together with -, they form a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced with -O- or -S-. X a represents an oxygen atom or a sulfur atom. * denotes a binding site.]

[0012] R aa1 , R aa2 and R aa3 Examples of the alkyl group of R include a methyl group, an ethyl group, a propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group. aa1 , R aa2 and R aa3 The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms. R aa1 , Raa2 and R aa3 Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. R aa1 , R aa2 and R aa3 The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (where * indicates a bonding site): aa1 , R aa2 and R aa3 The alicyclic hydrocarbon group preferably has 3 to 16 carbon atoms, and more preferably 3 to 12 carbon atoms. TIFF2023143845000013.tif9159R aa1 , R aa2 and R aa3 Examples of the aromatic hydrocarbon group of R include aryl groups such as phenyl, naphthyl, anthryl, biphenyl, and phenanthryl. aa1 , R aa2 and R aa3 The aromatic hydrocarbon group preferably has 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms.

[0013] Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group.

[0014] R aa1 and R aa2 -C(R aa1 )(R aa2 )(R aa3 ) includes the following groups. The alicyclic hydrocarbon group preferably has 3 to 16 carbon atoms, more preferably 3 to 12 carbon atoms. * represents the bonding site with -O-. TIFF2023143845000014.tif30140

[0015] The group represented by formula (1a) is a 1,1,1-trialkyl group (R aa1 , R aa2 and R aa3 is an alkyl group, preferably a tert-butyl group), a 2-alkyladamantan-2-yl group (in formula (1a), R aa1 , R aa2 and the carbon atoms to which they are bonded form an adamantyl group, and R aa3 is an alkyl group) and 1-(adamantan-1-yl)-1,1-dialkyl groups (in formula (1a), R aa1 and R aa2 is an alkyl group, and R aa3 is an adamantyl group).

[0016] R aa1' , R aa2' and R aa3' Examples of the hydrocarbon group include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. The alkyl group and the alicyclic hydrocarbon group are represented by R aa1 , R aa2 and R aa3 Examples of the groups include the same groups as those listed in 1. Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group is combined with an alicyclic hydrocarbon group (for example, a cycloalkylalkyl group or an alkylcycloalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. R aa2' and R aa3' are bonded to each other and the carbon atoms to which they are bonded and X a When forming a heterocyclic group together with -C(R aa1' )(R aa2' )-X a -(R aa3' ) includes the following groups: * represents a binding site. TIFF2023143845000015.tif21143R aa1' and R aa2' At least one of these is preferably a hydrogen atom.

[0017] Specific examples of the acid labile group (1a) include the following groups: * represents a bonding site. TIFF2023143845000016.tif71168

[0018] Specific examples of the acid labile group (2a) include the following groups: * represents a bonding site. TIFF2023143845000017.tif76165R 1 , R 2 and R 3 The bonding positions of A to the benzene ring are each independently 1 , A 2 and A 3 The bonding position of R may be either o-position, m-position or p-position. 1 , R 2 and R 3 are each independently, A 1 , A 2 and A 3 It is preferably bonded to the p-position or m-position relative to the bonding position of the above, and more preferably bonded to the p-position. R 1 , R 2 and R 3 each independently represents a hydroxy group, -OR 10 or -OL 1 -CO-OR 10 and each independently represents -OR 10 or -OL 1 -CO-OR 10 It is more preferable that: In addition, at least one of m1, m2, and m3 is 2 or more, or at least two of m1, m2, and m3 are 1 or more, and a plurality of R 10 If there are multiple R 10 may be the same or different from each other.

[0019] R 4 , R 5 , R 6 , R 7 , R 8 and R 9Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 4 , R 5 , R 6 , R 7 , R 8 and R 9 The haloalkyl group having 1 to 12 carbon atoms refers to an alkyl group having 1 to 12 carbon atoms and containing a halogen atom, and examples thereof include fluorinated alkyl groups having 1 to 12 carbon atoms, chlorinated alkyl groups having 1 to 12 carbon atoms, brominated alkyl groups having 1 to 12 carbon atoms, and iodinated alkyl groups having 1 to 12 carbon atoms. Examples of haloalkyl groups include perfluoroalkyl groups having 1 to 12 carbon atoms (e.g., trifluoromethyl, pentafluoroethyl, heptafluoropropyl, and nonafluorobutyl), 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and 3,3,4,4,4-pentafluorobutyl, chloromethyl, bromomethyl, and iodomethyl. The number of carbon atoms in the haloalkyl group is preferably 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Examples of the hydrocarbon group having 1 to 18 carbon atoms include chain hydrocarbon groups such as alkyl groups and alkanediyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups. The alkyl group is a linear or branched alkyl group, and examples thereof include alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The alkanediyl group is a linear or branched alkanediyl group, such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, or a hexane-1,6-diyl group; and Examples of branched alkanediyl groups include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The chain hydrocarbon group preferably has 1 to 12 carbon atoms, more preferably 1 to 9 carbon atoms, even more preferably 1 to 6 carbon atoms, even more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups shown below: The bonding site may be at any position. TIFF2023143845000018.tif46168Specifically, examples of monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl.Examples of polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl.The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms. Examples of groups formed by combining two or more of chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups include a group combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*, alkyl group-aromatic hydrocarbon group-alkanediyl group-*, where -CH2- contained in the alkanediyl group and the alkyl group may be replaced by -O-, -CO-, -S-, or -SO2-), a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group-alkanediyl group- Examples of such groups include an alkanediyl group-*, an alkyl group-alicyclic hydrocarbon group-*, an alkyl group-alicyclic hydrocarbon group-alkanediyl group-*, where —CH— contained in the alicyclic hydrocarbon group, the alkanediyl group, and the alkyl group may be replaced by —O—, —CO—, —S—, or —SO—, and groups combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, an aromatic hydrocarbon group-alicyclic hydrocarbon group-*, an alicyclic hydrocarbon group-aromatic hydrocarbon group-*, where —CH— contained in the alicyclic hydrocarbon group may be replaced by —O—, —CO—, —S—, or —SO—). * represents a bonding site. The aromatic hydrocarbon group -alkanediyl group-* includes aralkyl groups such as benzyl group and phenethyl group. Examples of the alkyl group-aromatic hydrocarbon group-* include a tolyl group, a xylyl group, and a cumenyl group. Examples of the alicyclic hydrocarbon group -alkanediyl group-* include cycloalkylalkyl groups such as a cyclohexylmethyl group, a cyclohexylethyl group, a 1-(adamantan-1-yl)methyl group, and a 1-(adamantan-1-yl)-1-methylethyl group. Examples of the alkyl group-alicyclic hydrocarbon group-* include cycloalkyl groups having an alkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, and a 2-alkyladamantan-2-yl group. Examples of the aromatic hydrocarbon group-alicyclic hydrocarbon group-* include a phenylcyclohexyl group. Examples of the alicyclic hydrocarbon group-aromatic hydrocarbon group-* include a cyclohexylphenyl group. In addition, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined, and any of the combined groups may be bonded to the benzene ring.

[0020] R 4 , R 5 , R 6 , R 7 , R 8 and R 9 When a -CH2- in a haloalkyl group or a hydrocarbon group represented by the formula (I) is replaced with -O-, -CO-, -S-, or -SO2-, the number of carbon atoms before the replacement is the total number of carbon atoms in the haloalkyl group or the hydrocarbon group. The number may be 1 or 2 or more. Examples of haloalkyl groups and groups in which -CH2- in a hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), and a hydroxyl group (a group in which -CH2- at any position in an alkyl group is replaced by -O-). a group in which -CH2-CH2- is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced by -CO-O-), an alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced by -S-), an alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced by -SO2-), an oxy group (a group in which -CH in a methylene group 2- is replaced by -O-), carbonyl group (a group in which -CH2- in a methylene group is replaced by -CO-), thio group (a group in which -CH2- in a methylene group is replaced by -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced by -SO2-), alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced by -O-), alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced by -O-CO-), a an alkanediylcarbonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced with -CO-O-), an alkanediylthio group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -S-), an alkanediylsulfonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -SO2-), a cycloalkoxy group, a cycloalkylalkoxy group,Examples of such groups include an alkoxycarbonyloxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, a haloalkoxy group (a group in which -CH- at any position in a haloalkyl group is replaced with -O-), a haloalkoxycarbonyl group (a group in which -CH-CH- at any position in a haloalkyl group is replaced with -O-CO-), a haloalkylcarbonyl group (a group in which -CH- at any position in a haloalkyl group is replaced with -CO-), a haloalkylcarbonyloxy group (a group in which -CH-CH- at any position in a haloalkyl group is replaced with -CO-O-), and a group in which two or more of these groups are combined. Examples of the alkoxy group include alkoxy groups having 1 to 17 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 17 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 18 carbon atoms, such as acetyl, propionyl, and butyryl. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 17 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The alkylcarbonyloxy group preferably has 2 to 11 carbon atoms, more preferably 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and even more preferably 2 or 3 carbon atoms. Examples of the alkylthio group include alkylthio groups having 1 to 17 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a 2-ethylhexylthio group, a nonylthio group, a decylthio group, an undecylthio group, etc. The number of carbon atoms in the alkylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 17 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a 2-ethylhexylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, etc. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 17 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 17 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 18 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 17 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 17 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 17 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 17 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 17 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 18 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 17 carbon atoms, such as a phenyloxy group. Examples of the haloalkoxy group, haloalkoxycarbonyl group, haloalkylcarbonyl group, and haloalkylcarbonyloxy group include haloalkoxy groups having 1 to 11 carbon atoms, haloalkoxycarbonyl groups having 2 to 11 carbon atoms, haloalkylcarbonyl groups having 2 to 12 carbon atoms, and haloalkylcarbonyloxy groups having 2 to 11 carbon atoms, and include groups in which one or more hydrogen atoms of the above-exemplified groups have been replaced with a halogen atom.

[0021] Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -SO2-, or -CO- include the groups shown below. Also included are groups in which, among the groups shown below, -O- is replaced with -S- and -CO- is replaced with -SO2-. The bonding site can be at any position. TIFF2023143845000019.tif46168

[0022] R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Examples of the substituent that the hydrocarbon group may have include a halogen atom, a cyano group, and an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-). Examples of the halogen atom include the same groups as those mentioned above. Examples of the alkyl group having 1 to 12 carbon atoms include the same groups as those mentioned above. When -CH2- in an alkyl group is replaced with -O- or -CO- as a substituent, the number of carbon atoms before the replacement is counted as the total number of carbon atoms in the alkyl group. Examples of the substituted group include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, and an alkylcarbonyloxy group. Examples of the alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, and alkylcarbonyloxy group include alkoxy groups having 1 to 11 carbon atoms, alkoxycarbonyl groups having 2 to 11 carbon atoms, alkylcarbonyl groups having 2 to 12 carbon atoms, and alkylcarbonyloxy groups having 2 to 11 carbon atoms, and include the same groups as those described above. The hydrocarbon group may have one or more substituents.

[0023] A 1 , A 2 and A 3 Examples of the hydrocarbon group include linear or branched chain hydrocarbon groups (e.g., alkanediyl groups, etc.), monocyclic or polycyclic alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be a combination of two or more of these groups. The number of carbon atoms in the hydrocarbon group is preferably 1 to 19, more preferably 1 to 18, even more preferably 1 to 16, still more preferably 1 to 14, and even more preferably 1 to 12. Examples of the chain hydrocarbon group include straight-chain alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl; Examples of branched alkanediyl groups include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 9, still more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups shown below: The bonding site may be at any position. TIFF2023143845000020.tif46168Specifically, monocyclic alicyclic hydrocarbon groups such as monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, and cyclooctane-1,5-diyl group; Examples of the polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group. The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms, even more preferably 3 to 12 carbon atoms, and even more preferably 3 to 10 carbon atoms. Examples of the aromatic hydrocarbon group include arylene groups such as a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, etc. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0024] Examples of groups formed by combining two or more groups include a group combining an alicyclic hydrocarbon group with an alkanediyl group, a group combining an aromatic hydrocarbon group with an alkanediyl group, and a group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group. The combinations may each comprise two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. Furthermore, any of the groups may be bonded to a benzene ring. Examples of groups combining an alicyclic hydrocarbon group and an alkanediyl group include -divalent alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent alicyclic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent alicyclic hydrocarbon group-. Examples of groups combining an aromatic hydrocarbon group and an alkanediyl group include -divalent aromatic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent aromatic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent aromatic hydrocarbon group-. Examples of groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group include -aromatic hydrocarbon group-alicyclic hydrocarbon group-, -alicyclic hydrocarbon group-aromatic hydrocarbon group-, and -alicyclic hydrocarbon group-aromatic hydrocarbon group-alicyclic hydrocarbon group-.

[0025] A 1 , A 2 and A 3 In the case where a -CH2- in the hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2-, the number of carbon atoms before the replacement is taken as the total number of carbon atoms in the hydrocarbon group. The number may be 1 or 2 or more, but is preferably 1 to 3. Examples of groups in which -CH2- in a hydrocarbon group is replaced by -O-, -CO-, -S-, or -SO2- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced by , -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), oxy group (a group in which -CH2- in a methylene group is replaced with -O- a carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), a thio group (a group in which -CH2- in a methylene group is replaced with -S-), a sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), an alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -O-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which an alkanediyl group in which -CH2- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -CO-O-), an alkanediylsulfonyl group (a group in which -CH2- at any position in an alkanediyl group is replaced with -SO2-), an alkanediylthio group (a group in which -CH2- at any position in an alkanediyl group is replaced with -S-), a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group,Examples include an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group formed by combining two or more of these groups. Examples of the alkoxy group include alkoxy groups having 1 to 19 carbon atoms, such as a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 19 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 20 carbon atoms, such as acetyl, propionyl, and butyryl. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 19 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The alkylcarbonyloxy group preferably has 2 to 11 carbon atoms, more preferably 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and even more preferably 2 or 3 carbon atoms. The alkylthio group includes alkylthio groups having 1 to 19 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, etc. The number of carbon atoms in the alkylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 19 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, etc. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 19 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 19 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 20 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 19 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 19 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 19 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 19 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 19 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 18 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 19 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 19 carbon atoms, such as a phenyloxy group.

[0026] Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2- include the groups shown below. Also included are groups in which, among the groups shown below, -O- is replaced with -S- and -CO- is replaced with -SO2-. The bonding site can be at any position. TIFF2023143845000021.tif47170A 1 , A 2 and A 3 The substituents that the hydrocarbon group may have include R 4 ~R 9 Examples of the groups include the same groups as those listed in the above.

[0027] A 1 , A 2 and A 3are each independently a hydrocarbon group having 1 to 20 carbon atoms (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-, provided that at least one of -CH2- contained in the hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2-). Specifically, A 1 is***-L 011 -X 01 -L 012 - and A 2 is***-L 021 -X 02 -L 022 - and A 3 is***-L 031 -X 03 -L 032 -is (X 01 , X 02 and X 03 each independently represents -O-, -CO-, -S- or -SO2-. 011 , L 012 , L 021 , L 022 , L 031 and L 032 are each independently a single bond or a hydrocarbon group having 1 to 19 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. 011 and L 012 The total number of carbon atoms is 0 to 19, and L 021 and L 022 The total number of carbon atoms is 0 to 19, and L 031 and L 032 The total number of carbon atoms is 0 to 19. *** indicates R 1 , R 2 and R 3 represents the bonding site with the benzene ring to which A is bonded. 1 is ***-X 01 -L 01 -or***-L 01 -X 01 - and A 2 is ***-X 02 -L02 -or***-L 02 -X 02 - and A 3 is ***-X 03 -L 03 -or***-L 03 -X 03 -is (X 01 , X 02 and X 03 each independently represents -O-, -CO-, -S- or -SO2-. 01 , L 02 and L 03 are each independently a single bond or a hydrocarbon group having 1 to 19 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. *** is R 1 , R 2 and R 3 represents the bonding site with the benzene ring to which A is bonded. 1 , A 2 and A 3 is preferably one that has no substituents other than substitution with -O-, -CO-, -S- or -SO2-. 011 , L 012 , L 021 , L 022 , L 031 , L 032 , L 01 , L 02 and L 03 The hydrocarbon group having 1 to 19 carbon atoms (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-) may be any of the hydrocarbon groups having 1 to 19 carbon atoms, 1 , A 2 and A 3 Examples of the groups include the same groups as those listed in the above. X 01 , X 02 and X 03 are each independently preferably -O- or -S-, more preferably -O-. L 011 , L 012 , L 021, L 022 , L 031 , L 032 , L 01 , L 02 and L 03 are each independently preferably a single bond or a hydrocarbon group having 1 to 18 carbon atoms (-CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-), more preferably a single bond or a hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-), and are each independently preferably a single bond or a chain hydrocarbon group having 1 to 9 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-). is more preferable, a single bond or an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), even more preferable, a single bond or an alkanediyl group having 1 to 4 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), and even more preferable, a single bond or an alkanediyl group having 1 to 3 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-). Among these, a single bond, a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-2,2-diyl group, a carbonyl group, a carbonyloxy group, a carbonyloxymethylene group, an ethyleneoxy group, a methylenecarbonyloxymethylene group, or an ethyleneoxycarbonyl group is preferred, and a single bond, a methylene group, or a carbonyl group is more preferred. A 1 The bonding positions of each of the groups to the benzene ring are independently + The bonding position may be either o-position, m-position or p-position. + More specifically, when m1 is 1, A 1 are each independently, S +It is preferably bonded to the p-position or m-position, more preferably to the p-position, relative to the bonding position of A. 1 are each independently, S + With respect to the bonding positions of A, it is preferable that one is bonded to the o-position or the m-position, and one is bonded to the o-position or the m-position, and it is more preferable that two are bonded to the m-position. 1 are each independently, S + With respect to the bonding positions of A, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position. 1 are each independently, S + With respect to the bonding positions of the above, it is preferred that two are bonded to the o-position or m-position and two are bonded to the p-position or m-position, and it is more preferred that two are bonded to the o-position and two are bonded to the m-position. A 2 and A 3 The bonding positions of each of the groups to the benzene ring are independently + The bonding position may be either o-position, m-position or p-position. + More specifically, when m2 and m3 are 1, A 2 and A 3 are each independently, S + Preferably, the bond is at the p-position or m-position relative to the bonding position of A, and more preferably at the p-position. 2 and A 3 are each independently, S + With respect to the bonding positions of A, it is preferred that one is bonded to the o-position or the m-position, and one is bonded to the o-position or the m-position, and it is more preferred that two are bonded to the m-position. 2 and A 3 are each independently, S +With respect to the bonding positions of the above, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position. m1 is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2, even more preferably 0 or 1, and even more preferably 1. m2 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. m3 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. At least one of m1, m2, and m3 is 1 or greater, and therefore m1 is preferably 1 or 2. m4 is preferably 0, 1, 2 or 4, and more preferably 0, 1 or 2. m5 is preferably 0, 1, 2 or 4, and more preferably 0, 1 or 2. m6 is preferably 0, 1, 2 or 4, and more preferably 0, 1 or 2. m7 is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1. m8 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. m9 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. Furthermore, since 0≦m1+m7≦5, 0≦m2+m8≦4, and 0≦m3+m9≦4, m7 is preferably 0, 1, or 2, and more preferably 0 or 1. R 4 , R 5 and R 6are each independently preferably a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), and are more preferably a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-). Any -CH2- contained therein may be replaced by -O- or -CO-.) It is more preferably a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, a hydroxy group, an alkoxy group having 1 to 3 carbon atoms or an alkyl group having 1 to 4 carbon atoms, it is even more preferably a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 3 carbon atoms, a hydroxy group or an alkoxy group having 1 to 3 carbon atoms, it is even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methoxy group, an ethoxy group or a hydroxy group. In another embodiment, one or more R 4 , R 5 and R 6 At least one of R may contain an acid labile group; 4 , R 5 , R 6 are each independently R 1 , R 2 , R 3 and R 1 -OR 10 In this case, one or two R 4 R 1 Same as -OR 10 Preferably, R 1 Ga-O-CO-OR 10 In this case, one or two R 4 R 1 Same as -O-CO-OR 10 Preferably, R 1 Ga-OL 1 -CO-OR 10 In this case, one or two R4 R 1 Same as -OL 1 -CO-OR 10 It is preferable that R 2 and R 5 Combination of R 3 and R 6 For each combination of 1 and R 4 The combination is similar to that of R 4 , R 5 and R 6 The bonding positions of A to the benzene ring are each independently 1 , A 2 and A 3 In particular, when m4, m5, and m6 are 1, R 4 , R 5 and R 6 are each independently, A 1 , A 2 and A 3 Preferably, m4, m5, and m6 are bonded to the p- or m-position, more preferably to the m-position, relative to the bonding position of R 4 , R 5 and R 6 are each independently, A 1 , A 2 and A 3 With respect to the bonding positions of R, it is preferred that one is bonded to the o-position or m-position, and one is bonded to the p-position or m-position, and it is more preferred that two are bonded to the m-position. 4 , R 5 and R 6 are each independently, A 1 , A 2 and A 3 With respect to the bonding positions of m4, m5, and m6, it is preferred that two of them are bonded to the o-position or m-position and one is bonded to the p-position or m-position, and it is more preferred that one is bonded to the o-position and two are bonded to the m-position. 4 , R 5 and R 6 are each independently, A 1 , A2 and A 3 With respect to the bonding positions of the above, it is preferred that two are bonded to the o-position or m-position and two are bonded to the p-position or m-position, and it is more preferred that two are bonded to the o-position and two are bonded to the m-position. R 7 , R 8 and R 9 are each independently preferably a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), still more preferably a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a hydroxy group, a methoxy group, a methyl group, or a t-butyl group. R 7 The bonding position of to the benzene ring is S + It may be at the o-position, m-position, or p-position relative to the bonding position of R 7 is S + It is preferably bonded to the p-position or m-position, more preferably to the p-position, relative to the bonding position of R 7 are each independently, S + With respect to the bonding positions of R, it is preferred that one is bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that one is bonded to the m-position and one is bonded to the p- or m-position. 7 are each independently, S + With respect to the bonding positions of R, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position. 7are each independently, S + With respect to the bonding positions of the above, it is preferred that two are bonded to the o-position or m-position and two are bonded to the p-position or m-position, and it is more preferred that two are bonded to the m-position, one is bonded to the o-position and one is bonded to the p-position. R 8 and R 9 The bonding positions of each of the groups to the benzene ring are independently + In particular, when m8 and m9 are 1, R 8 and R 9 are each independently, S + When m8 and m9 are 2, R 8 and R 9 are each independently, S + With respect to the bonding positions of R, it is preferred that one is bonded to the o-position or m-position and one is bonded to the p-position or m-position, and it is more preferred that one is bonded to the m-position and one is bonded to the p-position or m-position. 8 and R 9 are each independently, S + With respect to the bonding positions of the above, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position. X 4 is preferably a single bond, -CH2-, -O-, or -CO-, more preferably a single bond or -CH2-, and even more preferably a single bond.

[0028] Examples of the cation (I) represented by formula (IC) include the cation represented by formula (IC-1) (hereinafter sometimes referred to as "cation (IC-1)"). TIFF2023143845000022.tif81118[In formula (IC-1), R 1 , R 2 , R 3 , R 4 , R 5 , R6 , R 7 , R 8 , R 9 , X 4 , m1, m2, m3, m4, m5, m6, m7, m8, m9, L 01 , L 02 , L 03 , X 01 , X 02 and X 03 The symbols have the same meanings as above.] X 01 , X 02 and X 03 The bonding positions of A to the benzene ring are each independently 1 , A 2 and A 3 The bonding position to the benzene ring is the same as that of

[0029] Examples of the cation (I) of the salt (I) include cations represented by the following formulae (Ic-1) to (Ic-199).

[0030] TIFF2023143845000023.tif233144

[0031] TIFF2023143845000024.tif231161

[0032] TIFF2023143845000025.tif238154

[0033] TIFF2023143845000026.tif224156

[0034] TIFF2023143845000027.tif246162

[0035] TIFF2023143845000028.tif240149

[0036] TIFF2023143845000029.tif215166

[0037] TIFF2023143845000030.tif237161

[0038] TIFF2023143845000031.tif239164

[0039] TIFF2023143845000032.tif212158

[0040] TIFF2023143845000033.tif250144

[0041] TIFF2023143845000034.tif227161

[0042] TIFF2023143845000035.tif222160

[0043] TIFF2023143845000036.tif239167

[0044] TIFF2023143845000037.tif237163

[0045] TIFF2023143845000038.tif240159

[0046] TIFF2023143845000039.tif243163

[0047] [Anion (I)] The anion (I) of the salt represented by formula (I) is an anion represented by formula (IA). TIFF2023143845000040.tif2679 [In formula (IA), all symbols have the same meaning as in formula (I)] Q b1 and Q b2 Examples of the perfluoroalkyl group represented by the formula (I) include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, and a perfluorohexyl group. Q b1and Q b2 Examples of the alkyl group represented by include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Q b1 and Q b2 Preferably, at least one of the groups contains a fluorine atom or a perfluoroalkyl group, more preferably each independently is a fluorine atom or a perfluoroalkyl group, further preferably is a fluorine atom or a trifluoromethyl group, and even more preferably is both a fluorine atom.

[0048] L b1 Examples of the divalent saturated hydrocarbon group in include a linear alkanediyl group, a branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and may also be a group formed by combining two or more of these groups. Specific examples include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, a decane-1,10-diyl group, an undecane-1,11-diyl group, a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, and a heptadecane-1,17-diyl group; branched alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl; monocyclic divalent alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; Examples include polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group.

[0049] L b1 Examples of the group in which -CH2- in the divalent saturated hydrocarbon group represented by the formula (b1-1) is replaced with -O- or -CO- include groups represented by any of formulas (b1-1) to (b1-3). In the groups represented by formulas (b1-1) to (b1-3) and specific examples thereof, groups represented by formulas (b1-4) to (b1-11), * and ** represent bonding sites, * indicates -Y b1 represents the binding site with

[0050] TIFF2023143845000041.tif23103[In formula (b1-1), L b2 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b3 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, L b2 and L b3 The total number of carbon atoms is 22 or less. In formula (b1-2), L b4 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b5 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, L b4 and Lb5 The total number of carbon atoms is 22 or less. In formula (b1-3), L b6 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. L b7 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, L b6 and L b7 The total number of carbon atoms is 23 or less.

[0051] In the groups represented by formulae (b1-1) to (b1-3), when -CH2- contained in the saturated hydrocarbon group is replaced with -O- or -CO-, the number of carbon atoms before replacement is defined as the number of carbon atoms of the saturated hydrocarbon group. As the divalent saturated hydrocarbon group, L b1 Examples of the divalent saturated hydrocarbon group include the same as the divalent saturated hydrocarbon group.

[0052] L b2 is preferably a single bond, a methylene group, —CH(CF3)—, or —C(CF3)2—. L b3 is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b4 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom, and is more preferably a methylene group, -CH(CF3)-, or -C(CF3)2-. L b5 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b6 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. Lb7 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the divalent saturated hydrocarbon group may be substituted with -O- or -CO-.

[0053] L b1 As the divalent saturated hydrocarbon group represented by the formula (b1-1) or (b1-3), in which one --CH.sub.2-- contained in the group is replaced by --O-- or --CO--, a group represented by the formula (b1-1) or (b1-3) is preferred. Examples of the group represented by formula (b1-1) include groups represented by formulas (b1-4) to (b1-8). TIFF2023143845000042.tif48120[In 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 formula (b1-5), L b9 represents a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b10 represents a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b9 and L b10 The total number of carbon atoms is 20 or less. In formula (b1-6), L b11 represents a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b12 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b11 and L b12 The total number of carbon atoms is 21 or less. In formula (b1-7), L b13 represents a divalent saturated hydrocarbon group having 1 to 19 carbon atoms. L b14 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b15 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b13 ~L b15 The total number of carbon atoms is 19 or less. In formula (b1-8), L b16 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b17 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms. L b18 represents a single bond or a divalent saturated hydrocarbon group having 1 to 17 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b16 ~L b18 The total number of carbon atoms is 19 or less.

[0054] L b8 is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b9 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b10 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b11 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b12is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b13 is preferably a divalent saturated hydrocarbon group having 1 to 12 carbon atoms. L b14 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 6 carbon atoms. L b15 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b16 is preferably a divalent saturated hydrocarbon group having 1 to 12 carbon atoms. L b17 is preferably a divalent saturated hydrocarbon group having 1 to 6 carbon atoms. L b18 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 17 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms.

[0055] Examples of the group represented by formula (b1-3) include groups represented by formulas (b1-9) to (b1-11). TIFF2023143845000043.tif23140[In formula (b1-9), L b19 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b20 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxy group, or an alkylcarbonyloxy group. -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and a hydrogen atom contained in the alkylcarbonyloxy group may be substituted with a hydroxy group. However, L b19 and L b20 The total number of carbon atoms is 23 or less. In formula (b1-10), L b21represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b22 represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b23 represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxy group, or an alkylcarbonyloxy group. -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and a hydrogen atom contained in the alkylcarbonyloxy group may be substituted with a hydroxy group. However, L b21 , L b22 and L b23 The total number of carbon atoms is 21 or less. In formula (b1-11), L b24 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b25 represents a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b26 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom, a hydroxy group, or an alkylcarbonyloxy group. -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and a hydrogen atom contained in the alkylcarbonyloxy group may be substituted with a hydroxy group. However, L b24 , L b25 and L b26 The total number of carbon atoms is 21 or less.

[0056] In addition, in the groups represented by formulae (b1-9) to (b1-11), when a hydrogen atom contained in the saturated hydrocarbon group is substituted with an alkylcarbonyloxy group, the number of carbon atoms before substitution is regarded as the number of carbon atoms of the saturated hydrocarbon group. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, a cyclohexylcarbonyloxy group, and an adamantylcarbonyloxy group.

[0057] Examples of the group represented by formula (b1-4) include the following. TIFF2023143845000044.tif14134

[0058] Examples of the group represented by formula (b1-5) include the following. TIFF2023143845000045.tif60150

[0059] Examples of the group represented by formula (b1-6) include the following. TIFF2023143845000046.tif29165

[0060] Examples of the group represented by formula (b1-7) include the following. TIFF2023143845000047.tif41169

[0061] Examples of the group represented by formula (b1-8) include the following. TIFF2023143845000048.tif20123

[0062] Examples of the group represented by formula (b1-2) include the following. TIFF2023143845000049.tif31161

[0063] Examples of the group represented by formula (b1-9) include the following. TIFF2023143845000050.tif33152

[0064] Examples of the group represented by formula (b1-10) include the following. TIFF2023143845000051.tif80165

[0065] Examples of the group represented by formula (b1-11) include the following. TIFF2023143845000052.tif67153

[0066] Y b1 Examples of the alicyclic hydrocarbon group represented by the formula (Y1) to (Y11) and the formula (Y36) to (Y38) include groups represented by the formula (Y1) to (Y11) and the formula (Y36) to (Y38) in which -CH2- is not replaced by -O-, -S-, -SO2-, or -CO-. Y b1 When -CH2- contained in the alicyclic hydrocarbon group represented by the formula (Y12) is replaced by -O-, -S-, -SO2- or -CO-, the number may be one or more. Examples of such groups include groups represented by formulae (Y12) to (Y35) and (Y39) to (Y43). -O- or -CO- in the groups represented by formulae (Y12) to (Y35) and (Y39) to (Y43) may be replaced by -S- or -SO2-. The bonding site may be at any position.

[0067] TIFF2023143845000053.tif84167Y b1 The alicyclic hydrocarbon group represented by the formula (Y1) is preferably a group represented by any one of formulas (Y1) to (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39) to formula (Y43), more preferably a group represented by formula (Y11), formula (Y15), formula (Y16), formula (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39), formula (Y40), formula (Y42) or formula (Y43), and even more preferably a group represented by formula (Y11), formula (Y15), formula (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39), formula (Y40), formula (Y42) or formula (Y43).

[0068] Y b1Examples of the substituent of the alicyclic hydrocarbon group represented by the formula (I) include a halogen atom, a hydroxy group, a cyano group, an alkyl group having 1 to 16 carbon atoms which may be substituted with a hydroxy group (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, an aralkyl group having 7 to 21 carbon atoms, a glycidyloxy group, -(CH2) ja -CO-OR b1 group or -(CH2) ja -O-CO-R b1 group (in the formula, R 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, wherein -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, or the aromatic hydrocarbon group may be replaced by a hydroxy group or a fluorine atom. ja represents an integer of 0 to 4.

[0069] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, a dimethylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, a norbornyl group, and an adamantyl group. The alicyclic hydrocarbon group may have a chain hydrocarbon group, such as a methylcyclohexyl group or a dimethylcyclohexyl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 12, and more preferably 3 to 10. Examples of aromatic hydrocarbon groups include aryl groups such as phenyl, naphthyl, anthryl, biphenyl, and phenanthryl. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and aromatic hydrocarbon groups having a chain hydrocarbon group of 1 to 18 carbon atoms (such as tolyl, xylyl, cumenyl, mesityl, p-methylphenyl, p-ethylphenyl, p-tert-butylphenyl, 2,6-diethylphenyl, and 2-methyl-6-ethylphenyl) and aromatic hydrocarbon groups having an alicyclic hydrocarbon group of 3 to 18 carbon atoms (such as p-adamantylphenyl and p-cyclohexylphenyl) are preferred. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 14, and more preferably 6 to 10. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. Examples of the alkyl group substituted with a hydroxy group include hydroxyalkyl groups such as a hydroxymethyl group and a hydroxyethyl group. Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, a naphthylmethyl group, and a naphthylethyl group. Examples of groups in which -CH2- in an alkyl group is replaced by -O-, -SO2-, -CO-, etc. include an alkoxy group, an alkylsulfonyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, or a combination thereof. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group. The number of carbon atoms in the alkoxy group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, etc. The alkylsulfonyl group preferably has 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms. Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, etc. The alkoxycarbonyl group preferably has 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. The alkylcarbonyl group preferably has 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, etc. The alkylcarbonyloxy group preferably has 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms. Examples of the combined group include a group combining an alkoxy group and an alkyl group, a group combining an alkoxy group and an alkoxy group, a group combining an alkoxy group and an alkylcarbonyl group, and a group combining an alkoxy group and an alkylcarbonyloxy group. Examples of the group combining an alkoxy group and an alkyl group include alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, an ethoxyethyl group, an ethoxymethyl group, etc. The number of carbon atoms in the alkoxyalkyl group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of a group formed by combining an alkoxy group with another alkoxy group include alkoxyalkoxy groups such as a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, etc. The number of carbon atoms in the alkoxyalkoxy group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. Examples of the group combining an alkoxy group and an alkylcarbonyl group include alkoxyalkylcarbonyl groups such as a methoxyacetyl group, a methoxypropionyl group, an ethoxyacetyl group, an ethoxypropionyl group, etc. The number of carbon atoms in the alkoxyalkylcarbonyl group is preferably 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. Examples of the group combining an alkoxy group and an alkylcarbonyloxy group include alkoxyalkylcarbonyloxy groups such as a methoxyacetyloxy group, a methoxypropionyloxy group, an ethoxyacetyloxy group, an ethoxypropionyloxy group, etc. The number of carbon atoms in the alkoxyalkylcarbonyloxy group is preferably 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. Examples of the group in which one -CH2- in the alicyclic hydrocarbon group is replaced by -O-, -SO2-, -CO- or the like include groups represented by formulae (Y12) to (Y35) and formulae (Y39) to (Y43).

[0070] Y b1 The alicyclic hydrocarbon group in (wherein -CH2- may be replaced with -O-, -CO-, -S-, or -SO2-) is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- may be replaced with -O-, -CO-, -S-, or -SO2-), more preferably a group represented by any of formulas (w1-1) to (w1-24), even more preferably a group represented by any of formulas (w1-1) to (w1-6) and (w1-12) to (w1-24), and even more preferably a group represented by any of formulas (w1-1) to (w1-3), (w1-15), and (w1-22). TIFF2023143845000054.tif46168 [Formula (w1-1) to formula (w1-24), The —CH2— contained in the group may be replaced by —O—, —S—, —CO— or —SO2—. The bonding site may be at any position.]

[0071] Y b1 is preferably a single bond or an alicyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, more preferably a single bond or an alicyclic hydrocarbon group of 3 to 20 carbon atoms which may have a substituent, even more preferably a single bond or an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent, and even more preferably an optionally substituted cyclohexanediyl group, an optionally substituted adamantanediyl group, an optionally substituted norbornanediyl group, an optionally substituted adamantanelactonediyl group, or an optionally substituted norbornanelactonediyl group, wherein -CH2- constituting the alicyclic hydrocarbon group, cyclohexanediyl group, adamantanediyl group, or norbornanediyl group may be replaced by -O-, -S-, -CO-, or -SO2-. Y b1 The substituent that may be possessed by is preferably a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms which may be substituted with a hydroxy group (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), or an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. Examples of the halogen atom, alkyl group, alkoxy group, and alicyclic hydrocarbon group are the same as those mentioned above. Of these, a fluorine atom, a hydroxy group, a methyl group, or an ethyl group is preferred.

[0072] R bb1 The halogen atoms in R 4 ~R 9 The same halogen atoms as those listed in R are included. bb1 The alkyl group which may have a halogen atom is R 4 ~R 9 Examples of the alkyl group and the haloalkyl group include the same alkyl group and haloalkyl group as those mentioned above. R bb1is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, even more preferably a hydrogen atom or a methyl group, and even more preferably a methyl group. X 10 is a group represented by *-Ax-Ph-Ay-**, it is preferably a linking group represented by the following formula (X10). TIFF2023143845000055.tif3449In the formula (X10), Ax is R bb1 represents a bond type that bonds to a carbon atom to which is bonded, and represents one bond type selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. Ay is L 10 represents a bond species that bonds to the above, and represents one type of bond species selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. When either Ax or Ay is a single bond, the other is preferably one selected from the group consisting of an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. Among these, a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, or an ethyl group is preferred. mx represents an integer of 0 to 4, and is preferably 0, 1 or 2. When mx is an integer of 2 or more, multiple Rx's may be the same or different. The bonding position of Ay in the phenylene group is preferably the m-position or p-position relative to the bonding position of Ax, and more preferably the p-position. X 10 For example, the following formula (X 10 -1)~Formula(X 10 -10). * and ** represent binding sites, * represents R bb1 represents the bonding site with the carbon atom to which it is attached. TIFF2023143845000056.tif46170 expression (X 10 -3)~Formula(X 10 Specific examples of the group represented by -10) include the following groups: TIFF2023143845000057.tif75161Among them, X 10 is a single bond or a group of the formula (X 10 -1), formula (X 10 -3')~expression(X 10 -10'), and is preferably a single bond or a group represented by the formula (X 10 -1), formula (X 10 -4'), expression (X 10 -5'), expression (X 10 -6') and formula (X 10 -10'), and more preferably a single bond, a group represented by the formula (X 10 -1), a group represented by the formula (X 10 -5') or a group represented by the formula (X 10 -6') is more preferred.

[0073] L 10 Examples of the hydrocarbon group having 1 to 36 carbon atoms include divalent aliphatic hydrocarbon groups (divalent chain hydrocarbon groups and divalent alicyclic hydrocarbon groups such as alkanediyl groups, alkenediyl groups, and alkynediyl groups), divalent aromatic hydrocarbon groups, and the like, and may be divalent hydrocarbon groups formed by combining two or more of these groups.

[0074] Examples of the alkanediyl group include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, a decane-1,10-diyl group, an undecane-1,11-diyl group, and a dodecane-1,12-diyl group; Examples of branched alkanediyl groups include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. Examples of the alkenediyl group include an ethenediyl group, a propenediyl group, an isopropenediyl group, a butenediyl group, an isobutenediyl group, a tert-butenediyl group, a pentenediyl group, a hexenediyl group, a heptenediyl group, an octenediyl group, an isooctenediyl group, and a nonenediyl group. Examples of the alkynediyl group include an ethynediyl group, a propynediyl group, an isopropynediyl group, a butynediyl group, an isobutynediyl group, a tert-butynediyl group, a pentynediyl group, a hexynediyl group, an octynediyl group, and a nonynediyl group. The chain hydrocarbon group preferably has 1 to 12 carbon atoms, more preferably 1 to 9 carbon atoms, even more preferably 1 to 6 carbon atoms, even more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms. The divalent alicyclic hydrocarbon group may be monocyclic, polycyclic, or spirocyclic. Examples of the divalent alicyclic hydrocarbon group include the groups shown below. The bonding site can be any position. TIFF2023143845000058.tif47167Specific examples of monocyclic divalent alicyclic hydrocarbon groups include monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, cyclohexene-3,6-diyl, and cyclooctane-1,5-diyl.Examples of polycyclic divalent alicyclic hydrocarbon groups include polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, 5-norbornene-2,3-diyl, adamantane-1,5-diyl, and adamantane-2,6-diyl. The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms, and even more preferably 3 to 12 carbon atoms. Examples of the divalent aromatic hydrocarbon group include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, etc. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms. Examples of hydrocarbon groups that combine two or more types include groups that combine an alkanediyl group with an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group, such as -alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-aromatic hydrocarbon group-, and -aromatic hydrocarbon group-alkanediyl group-.

[0075] L 10 -CH2- contained in the hydrocarbon group having 1 to 36 carbon atoms may be replaced by -O-, -S-, -CO- or -SO2-. L 10 When the hydrocarbon group having 1 to 36 carbon atoms has a substituent, or when -CH2- contained in the hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2-, the number of carbon atoms before replacement is regarded as the number of carbon atoms of the hydrocarbon group. Examples of groups in which -CH2- in a hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced by , -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), oxy group (a group in which -CH2- in a methylene group is replaced with -O-), carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), thio group (a group in which -CH2- in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced with -S-), an alkanediyloxy group (an alkanediyl group in which any -CH2- at any position is replaced with -SO2-), an alkanediyloxycarbonyl group (an alkanediyl group in which any -CH2- at any position is replaced with -O-), an alkanediylcarbonyl group (an alkanediyl group in which any -CH2- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (an alkanediyl group in which any -CH2- at any position is replaced with -CO-O-), a group in which -CH2- at any position in an alkyl group is replaced with -S-), an alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), an alkanediylthio group (a group in which -CH2- at any position in an alkanediyl group is replaced with -S-), an alkanediylsulfonyl group (a group in which -CH2- at any position in an alkanediyl group is replaced with -SO2-), a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group,Examples include an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group formed by combining two or more of these groups. Examples of the alkoxy group include alkoxy groups having 1 to 17 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 17 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 18 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 17 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. The number of carbon atoms in the alkoxycarbonyl group, alkylcarbonyl group, and alkylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 17 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 17 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 18 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 17 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. The alkanediyloxycarbonyl group, alkanediylcarbonyl group, and alkanediylcarbonyloxy group preferably have 2 to 11 carbon atoms, more preferably 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and even more preferably 2 to 3 carbon atoms. Examples of the alkylthio group include alkylthio groups having 1 to 17 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, etc. The number of carbon atoms in the alkylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 17 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, etc. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 17 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 17 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 17 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as a butoxycarbonyloxy group. The number of carbon atoms in the cycloalkoxy group or cycloalkylalkoxy group is preferably 3 to 11, more preferably 3 to 6. The number of carbon atoms in the alkoxycarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 to 3. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 17 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 18 carbon atoms, such as a benzoyl group. Examples of the aromatic hydrocarbon group-oxy group include aromatic hydrocarbon group-oxy groups having 6 to 17 carbon atoms, such as a phenyloxy group. Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2- include the groups shown below. -O- or -CO- in the groups shown below may be replaced with -S- or -SO2-. The bonding site may be at any position. TIFF2023143845000059.tif46168

[0076] L 10The substituents that the hydrocarbon group may have include a halogen atom, a cyano group, and the like. L 10 The hydrocarbon group of the formula (I) is a group in which -CH2- is replaced by -O- or -CO-. 10 can substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, or an alkylcarbonyloxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L 10 The hydrocarbon group having 1 to 36 carbon atoms may have one or more substituents.

[0077] L 10represents a single bond, an alkanediyl group having 1 to 6 carbon atoms (provided that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and that -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-), or a group formed by combining an alkanediyl group having 1 to 6 carbon atoms with a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group has a substituent). and -CH2- in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-.) and is preferably a single bond, an alkanediyl group having 1 to 4 carbon atoms (wherein -CH2- in the alkanediyl group may be replaced with -O- or -CO-), or an alicyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, or -CO-). -, -S-, -SO2- or -CO-), an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, a group formed by combining an alkanediyl group having 1 to 4 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-, and -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-), or an alkanediyl group having 1 to 4 carbon atoms and a substituent and an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a carbon number of 6 to 18 (provided that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), more preferably a single bond, an alkanediyl group having 1 to 4 carbon atoms (provided that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), or an alicyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-).), a phenylene group which may have a substituent, a group formed by combining an alkanediyl group of 1 to 4 carbon atoms with an alicyclic hydrocarbon group of 3 to 18 carbon atoms (provided that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-, and -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), or a group formed by combining an alkanediyl group of 1 to 4 carbon atoms with a phenylene group which may have a substituent (provided that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), and even more preferably a single bond or an alkanediyl group of 1 to 4 carbon atoms (provided that -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-).

[0078] Examples of the anion (I) include the following anions: TIFF2023143845000060.tif116146

[0079] In the anions represented by formulas (Ia-1) to (Ia-14), R bb1 Specific examples of the anion (I) include anions in which the methyl group corresponding to the formula (Ia-1) is replaced with a hydrogen atom. Among these, the anions represented by formulas (Ia-1) to (Ia-6) and (Ia-14) are preferred.

[0080] Specific examples of the salt (I) include salts formed by any combination of the above-mentioned cations and anions. Specific examples of the salt (I) are shown in the table below. In the table below, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation, and "~" indicates that the salt (I) corresponds to the anion (I). For example, salt (I-1) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-1), and is the salt shown below. Furthermore, salt (I-2) is a salt consisting of an anion represented by formula (Ia-2) and a cation represented by formula (Ic-1), and salt (I-15) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-2). TIFF2023143845000061.tif53103 [Table 1] TIFF2023143845000063.tif223158 TIFF2023143845000064.tif223158 TIFF2023143845000065.tif223158 TIFF2023143845000066.tif218158

[0081] Among them, salt (I) is salt (I-1) to salt (I-6), salt (I-15) to salt (I-20), salt (I-29) to salt (I-34), salt (I-43) to salt (I-48), salt (I-57) to salt (I-62), salt (I-71) to salt (I-76), salt (I-85) to salt (I-90), salt (I-9 9) ~ Salt (I-104), Salt (I-113) ~ Salt (I-118), Salt (I-127) ~ Salt (I-132), Salt (I-141) ~ Salt (I-146), Salt (I-155) ~ Salt (I-160), Salt (I-169) ~ Salt (I-174), Salt (I-183) ~ Salt (I-188), Salt (I-1 97)~Salt(I-202), Salt(I-211)~Salt(I-216), Salt(I-225)~Salt(I-230), Salt(I-239)~Salt(I-244), Salt(I-253)~Salt(I-258), Salt(I-267)~Salt(I-272), Salt(I-281)~Salt(I-286), Salt(I- 295) ~ Salt (I-300), Salt (I-309) ~ Salt (I-314), Salt (I-323) ~ Salt (I-328), Salt (I-337) ~ Salt (I-342), Salt (I-351) ~ Salt (I-356), Salt (I-365) ~ Salt (I-370), Salt (I-379) ~ Salt (I-384), Salt (I -393)~Salt(I-398), Salt(I-407)~Salt(I-412), Salt(I-421)~Salt(I-426), Salt(I-435)~Salt(I-440), Salt(I-449)~Salt(I-454), Salt(I-463)~Salt(I-468), Salt(I-477)~Salt(I-482), Salt( I-491) ~ Salt (I-496), Salt (I-505) ~ Salt (I-510), Salt (I-519) ~ Salt (I-524), Salt (I-533) ~ Salt (I-538), Salt (I-547) ~ Salt (I-552), Salt (I-561) ~ Salt (I-566), Salt (I-575) ~ Salt (I-580), Salt (I-589)~Salt(I-594), Salt(I-603)~Salt(I-608), Salt(I-617)~Salt(I-622), Salt(I-631)~Salt(I-636), Salt(I-645)~Salt(I-650), Salt(I-659)~Salt(I-664), Salt(I-673)~Salt(I-678), Salt (I-687) ~ Salt (I-692), Salt (I-701) ~ Salt (I-706), Salt (I-715) ~ Salt (I-720), Salt (I-729) ~ Salt (I-734), Salt (I-743) ~ Salt (I-748), Salt (I-757) ~ Salt (I-762), Salt (I-771) ~ Salt (I-776),Salt (I-785) ~ Salt (I-790), Salt (I-799) ~ Salt (I-804), Salt (I-813) ~ Salt (I-818), Salt (I-827) ~ Salt (I-832), Salt (I-841) ~ Salt (I-846), Salt (I-855) ~ Salt (I-860), Salt (I-869) ~ Salt (I-87 4), salt (I-883) ~ salt (I-888), salt (I-897) ~ salt (I-902), salt (I-911) ~ salt (I-916), salt (I-925) ~ salt (I-930), salt (I-939) ~ salt (I-944), salt (I-953) ~ salt (I-958), salt (I-967) ~ salt (I- 972), Salt (I-981) ~ Salt (I-986), Salt (I-995) ~ Salt (I-1000), Salt (I-1009) ~ Salt (I-1014), Salt (I-1023) ~ Salt (I-1028), Salt (I-1037) ~ Salt (I-1042), Salt (I-1051) ~ Salt (I-1056), Salt (I-1065)~Salt(I-1070), Salt(I-1079)~Salt(I-1084), Salt(I-1093)~Salt(I-1098), Salt(I-1107)~Salt(I-1112), Salt(I-1121)~Salt(I-1126), Salt(I-1135)~Salt(I-1140), Salt(I-1 149)~Salt(I-1154), Salt(I-1163)~Salt(I-1168), Salt(I-1177)~Salt(I-1182), Salt(I-1191)~Salt(I-1196), Salt(I-1205)~Salt(I-1210), Salt(I-1219)~Salt(I-1224), Salt(I-1233) ) ~ Salt (I-1238), Salt (I-1247) ~ Salt (I-1252), Salt (I-1261) ~ Salt (I-1266), Salt (I-1275) ~ Salt (I-1280), Salt (I-1289) ~ Salt (I-1294), Salt (I-1303) ~ Salt (I-1308), Salt (I-1317) ~ Salt ( I-1322), Salt (I-1331) ~ Salt (I-1336), Salt (I-1345) ~ Salt (I-1350), Salt (I-1359) ~ Salt (I-1364), Salt (I-1373) ~ Salt (I-1378), Salt (I-1387) ~ Salt (I-1392), Salt (I-1401) ~ Salt (I-14 06), Salt (I-1415) ~ Salt (I-1420), Salt (I-1429) ~ Salt (I-1434), Salt (I-1443) ~ Salt (I-1448), Salt (I-1457) ~ Salt (I-1462), Salt (I-1471) ~ Salt (I-1476), Salt (I-1485) ~ Salt (I-1490),Salt (I-1499) ~ Salt (I-1504), Salt (I-1513) ~ Salt (I-1518), Salt (I-1527) ~ Salt (I-1532), Salt (I-1541) ~ Salt (I-1546), Salt (I-1555) ~ Salt (I-1560), Salt (I-1569) ~ Salt (I-1574), Salt (I-1 583)~Salt(I-1588), Salt(I-1597)~Salt(I-1602), Salt(I-1611)~Salt(I-1616), Salt(I-1625)~Salt(I-1630), Salt(I-1639)~Salt(I-1644), Salt(I-1653)~Salt(I-1658), Salt(I-1667)~ Salt (I-1672), Salt (I-1681) ~ Salt (I-1686), Salt (I-1695) ~ Salt (I-1700), Salt (I-1709) ~ Salt (I-1714), Salt (I-1723) ~ Salt (I-1728), Salt (I-1737) ~ Salt (I-1742), Salt (I-1751) ~ Salt (I-1 756), Salt (I-1765) ~ Salt (I-1770), Salt (I-1779) ~ Salt (I-1784), Salt (I-1793) ~ Salt (I-1798), Salt (I-1807) ~ Salt (I-1812), Salt (I-1821) ~ Salt (I-1826), Salt (I-1835) ~ Salt (I-1840), Salt (I-1849) ~ Salt (I-1854), Salt (I-1863) ~ Salt (I-1868), Salt (I-1877) ~ Salt (I-1882), Salt (I-1891) ~ Salt (I-1896), Salt (I-1905) ~ Salt (I-1910), Salt (I-1919) ~ Salt (I-1924), Salt (I-1 933)~Salt(I-1938), Salt(I-1947)~Salt(I-1952), Salt(I-1961)~Salt(I-1966), Salt(I-1975)~Salt(I-1980), Salt(I-1989)~Salt(I-1994), Salt(I-2003)~Salt(I-2008), Salt(I-2017)~ Salt (I-2022), Salt (I-2031) ~ Salt (I-2036), Salt (I-2045) ~ Salt (I-2050), Salt (I-2059) ~ Salt (I-2064), Salt (I-2073) ~ Salt (I-2078), Salt (I-2087) ~ Salt (I-2092), Salt (I-2101) ~ Salt (I-2 106), Salt (I-2115) ~ Salt (I-2120), Salt (I-2129) ~ Salt (I-2134), Salt (I-2143) ~ Salt (I-2148), Salt (I-2157) ~ Salt (I-2162), Salt (I-2171) ~ Salt (I-2176), Salt (I-2185) ~ Salt (I-2190),Salt(I-2199)~Salt(I-2204), Salt(I-2213)~Salt(I-2218), Salt(I-2227)~Salt(I-2232), Salt(I-2241)~Salt(I-2246), Salt(I-2254)~Salt(I-2260), Salt(I-2269)~Salt(I-2275), Salt(I-2283)~Salt(I-2288), Salt(I-2297)~Salt(I-2302), Salt(I-2310)~Salt(I-2315), Salt(I-2325)~Salt(I-2330), Salt(I-2339)~Salt( I-2344), salt(I-2353)~salt(I-2358), salt(I-2367)~salt(I-2372), salt(I-2381)~salt(I-2386), salt(I-2395)~salt(I-2400), salt(I-2409)~salt(I-2414), salt(I-2423)~salt(I-2428), salt(I-2437)~salt(I-2442), salt(I-2451)~salt(I-2456), salt(I-2465)~salt(I-2470), salt(I-2479)~salt(I-2484), salt(I-2 493)~Salt(I-2498), Salt(I-2507)~Salt(I-2512), Salt(I-2521)~Salt(I-2526), ​​Salt(I-2535)~Salt(I-2540), Salt(I-2549)~Salt(I-2554), Salt(I-2563)~Salt(I-2568), Salt(I-2577)~Salt(I-2582), Salt(I-2591)~Salt(I-2596), Salt(I-2605)~Salt(I-2610), Salt(I-2619)~Salt(I-2624), Salt(I-2633)~Salt(I-263 8), salt (I-2647) to salt (I-2652), salt (I-2661) to salt (I-2666), salt (I-2675) to salt (I-2680), salt (I-2689) to salt (I-2694), salt (I-2703) to salt (I-2708), salt (I-2717) to salt (I-2722), salt (I-2731) to salt (I-2736), salt (I-2745) to salt (I-2750), salt (I-2759) to salt (I-2764), salt (I-2773) to salt (I-2778).

[0082] <Method for producing salt (I)> The salt (I) can be produced by reacting a salt represented by formula (Ia) with a compound represented by formula (Ib) in a solvent in the presence of a catalyst. TIFF2023143845000067.tif117164 [where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R bb1 , m1, m2, m3, m4, m5, m6, m7, m8, m9, A 1 , A 2 , A 3 , X 4 , Q b1 , Q b2 , L b1 , Y b1 , L 10 , X 10 The symbols have the same meanings as above. L b2 L b1 From the end -(CO) (1-nn) represents a group excluding —O—, and nn represents 0 or 1.] Examples of the catalyst include carbonyldiimidazole and base catalysts (dimethylaminopyridine). Examples of the solvent include chloroform, monochlorobenzene, and acetonitrile. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.

[0083] Examples of salts represented by formula (Ia) include salts represented by the following formula: These salts can be easily produced by known production methods. TIFF2023143845000068.tif216164

[0084] TIFF2023143845000069.tif248163

[0085] TIFF2023143845000070.tif227162

[0086] TIFF2023143845000071.tif252159

[0087] TIFF2023143845000072.tif229149

[0088] Examples of the compound represented by formula (Ib) include compounds represented by the following formula: These compounds are readily available on the market or can be easily produced by known production methods. TIFF2023143845000073.tif43164

[0089] [Structural unit derived from a salt represented by formula (I)] The structural unit derived from the salt represented by formula (I) is a structural unit represented by formula (IP) (hereinafter sometimes referred to as "structural unit (IP)"). Such a structural unit (IP) functions as an acid generator like the salt (I), and also functions as a structural unit constituting a compound or resin.

[0090] [Resin containing a structural unit (IP) derived from a salt represented by formula (I)] The resin of the present invention is a resin containing a structural unit (IP) derived from a salt represented by formula (I) (hereinafter, sometimes referred to as "resin (Ap)"). TIFF2023143845000074.tif81154[In formula (IP), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R bb1 , m1, m2, m3, m4, m5, m6, m7, m8, m9, A 1 , A 2 , A 3 , X 4 , Q b1 , Q b2 , L b1 , Y b1 , X 10 , L 10 The symbols have the same meanings as above.] The structural unit (IP) is CH2=CR contained in salt (I). bb1 This shows the state in which the double bond is cleaved. The resin (Ap) may be a homopolymer containing one type of structural unit (IP), or a copolymer containing two or more types of structural units (IP). Furthermore, the resin (Ap) may contain a structural unit other than the structural unit (IP). Examples of structural units other than the structural unit (IP) include, as will be described later, a structural unit having an acid labile group (hereinafter sometimes referred to as "structural unit (a1)"), a structural unit not having an acid labile group (hereinafter sometimes referred to as "structural unit (s)"), other structural units (hereinafter sometimes referred to as "structural unit (t)"), and structural units known in the art. Here, the term "acid labile group" refers to a group that has a leaving group and that is eliminated upon contact with an acid, converting the structural unit into a structural unit having a hydrophilic group (e.g., a hydroxy group or a carboxy group). The content of the structural unit (IP) relative to all structural units in the resin (Ap) can be 0.1 mol% or more, preferably 0.5 mol% or more, more preferably 0.8 mol% or more, and even more preferably 1 mol% or more. It can also be 100 mol% or less, preferably 50 mol% or less, more preferably 30 mol% or less, and even more preferably 10 mol% or less. Specifically, it can be 0.1 to 100 mol%, preferably 0.5 to 50 mol%, more preferably 0.8 to 30 mol%, and even more preferably 1 to 10 mol%.

[0091] In particular, when the resin (Ap) is used in a resist composition, as described below, it may further contain the structural unit (a1) in addition to the structural unit (IP). Furthermore, as will be described later, when resin (Ap) is used in a resist composition, regardless of whether it contains the structural unit (a1), it may be used in combination with a resin containing the structural unit (a1) (hereinafter sometimes referred to as "resin (A)") and / or a resin other than resin (A). Hereinafter, resin (Ap) and / or resin (A) may be referred to as "resin (A), etc." It is preferable that the resin (Ap) and the resin (A) each further contain a structural unit other than the structural unit (a1). Examples of structural units other than the structural unit (a1) include structural units that do not have an acid labile group (hereinafter sometimes referred to as "structural unit (s)"), other structural units (hereinafter sometimes referred to as "structural unit (t)"), and structural units known in the art.

[0092] <Structural unit (a1)> The structural unit (a1) is derived from a monomer having an acid labile group (hereinafter sometimes referred to as "monomer (a1)"). The acid labile group contained in the resin (A) or the like 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)). TIFF2023143845000075.tif1988[In formula (1), R a1 , R a2 and R a3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining any of these; or R a1 and R a2 are bonded to each other to form a non-aromatic hydrocarbon ring having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded. ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * denotes a binding site.] TIFF2023143845000076.tif2171[In formula (2), R a1’ and R a2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R a2’ and R a3’ are bonded to each other to form a heterocyclic ring having 3 to 20 carbon atoms together with the carbon atom to which they are bonded and X, and -CH2- contained in the hydrocarbon group and the heterocyclic ring may be replaced with -O- or -S-. X represents an oxygen atom or a sulfur atom. na' represents 0 or 1. * denotes a binding site.]

[0093] R a1 , R a2 and R a3 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. R a1 , R a2 and R a3 Examples of the alkenyl group in the formula (I) include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. R a1 , R a2 and R a3 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (* indicates a bonding site): a1 , R a2 and R a3 The alicyclic hydrocarbon group preferably has 3 to 16 carbon atoms. TIFF2023143845000077.tif10150R a1 , R a2 and R a3 Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. Preferably, ma is 0 and na is 1. R a1 and R a2 -C(R a1 )(R a2 )(R a3 ) includes the following rings. The non-aromatic hydrocarbon ring preferably has 3 to 12 carbon atoms. * represents the bonding site with -O-. TIFF2023143845000078.tif30138

[0094] R a1’ , R a2’ and R a3’ Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. Alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups are R a1 , R a2 and R a3 Examples of the groups include the same as those listed in the above. R a2’ and R a3’ When they are bonded to each other to form a heterocycle together with the carbon atoms to which they are bonded and X, -C(R a1’ )(R a2’)-XR a3’ Examples of the ring include the following: * represents a binding site. TIFF2023143845000079.tif18130R a1’ and R a2’ At least one of these is preferably a hydrogen atom. na' is preferably 0.

[0095] Examples of the group (1) include the following groups. In formula (1), R a1 , R a2 and R a3 is an alkyl group, ma=0, and na=1. The group is preferably a tert-butoxycarbonyl group. In formula (1), R a1 , R a2 together with the carbon atom to which they are attached form an adamantyl group, and R a3 is an alkyl group, ma=0, and na=1. In formula (1), R a1 and R a2 are each independently an alkyl group, and R a3 is an adamantyl group, ma=0, and na=1. Specific examples of the group (1) include the following: * represents a binding site. TIFF2023143845000080.tif154163

[0096] Specific examples of group (2) include the following groups: * represents a binding site. TIFF2023143845000081.tif55153

[0097] The monomer (a1) is preferably a monomer having an acid labile group and an ethylenically unsaturated bond, more preferably a (meth)acrylic monomer having an acid labile group.

[0098] Of the (meth)acrylic monomers having an acid labile group, preferred are those having an alicyclic hydrocarbon group having 5 to 20 carbon atoms. The use of a resin (A) or the like having a structural unit derived from a monomer (a1) having a bulky structure such as an alicyclic hydrocarbon group in a resist composition can improve the resolution of the resist pattern.

[0099] Examples of structural units derived from a (meth)acrylic monomer having group (1) include a structural unit represented by formula (a1-0) (hereinafter sometimes referred to as structural unit (a1-0)), a structural unit represented by formula (a1-1) (hereinafter sometimes referred to as structural unit (a1-1)), or a structural unit represented by formula (a1-2) (hereinafter sometimes referred to as structural unit (a1-2)). Preferably, at least one structural unit selected from the group consisting of the structural unit (a1-0), the structural unit (a1-1), and the structural unit (a1-2) is used, and more preferably at least one structural unit selected from the group consisting of the structural unit (a1-1) and the structural unit (a1-2). These may be used alone or in combination of two or more. TIFF2023143845000082.tif44144 [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or -O-(CH2) k1 represents —CO—O—, k1 represents an integer of 1 to 7, and * represents the bonding site with —CO—. R a01 , R a4 and R a5 each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. R a6 and R a7each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these. m1' represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1' represents an integer of 0 to 3.

[0100] R a01 , R a4 and R a5 is preferably a hydrogen atom or a methyl group, more preferably a methyl group. L a01 , L a1 and L a2 is preferably an oxygen atom or —O—(CH2) k01 It is —CO—O— (wherein k01 is preferably an integer of any one of 1 to 4, more preferably 1), and more preferably an oxygen atom. R a02 , R a03 and R a04 The alkyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group and combination thereof in the group (1) R a1 , R a2 and R a3 Examples of the groups include the same groups as those listed in the above. R a6 and R a7 The alkyl group, alkenyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group and combinations thereof in the formula (1) include R a1 , R a2 and R a3 Examples of the groups include the same groups as those listed in the above. R a02 , R a03 , and R a04 The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a6 and R a7The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and even more preferably an ethyl group, an isopropyl group, or a t-butyl group. R a6 and R a7 The alkenyl group in the formula (I) is preferably an alkenyl group having 2 to 6 carbon atoms, and more preferably an ethenyl group, a propenyl group, an isopropenyl group, or a butenyl group. R a02 , R a03 , R a04 , R a6 and R a7 The alicyclic hydrocarbon group preferably has 5 to 12 carbon atoms, and more preferably 5 to 10 carbon atoms. R a02 , R a03 , R a04 , R a6 and R a7 The aromatic hydrocarbon group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms. In the group in which an alkyl group and an alicyclic hydrocarbon group are combined, the total number of carbon atoms in the combination of the alkyl group and the alicyclic hydrocarbon group is preferably 18 or less. In the group in which an alkyl group and an aromatic hydrocarbon group are combined, the total number of carbon atoms in the combination of the alkyl group and the aromatic hydrocarbon group is preferably 18 or less. R a02 and R a03 is preferably an alkyl group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, and more preferably a methyl group, an ethyl group, a phenyl group or a naphthyl group. R a04 is preferably an alkyl group having 1 to 6 carbon atoms or an alicyclic hydrocarbon group having 5 to 12 carbon atoms, and more preferably a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group. R a6 and R a7are each independently preferably an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, a phenyl group, or a naphthyl group, and even more preferably an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, or a phenyl group. m1' is preferably an integer of 0 to 3, and more preferably 0 or 1. n1 is preferably an integer of 0 to 3, and more preferably 0 or 1. n1' is preferably 0 or 1.

[0101] Examples of the structural unit (a1-0) include structural units represented by any one of formulas (a1-0-1) to (a1-0-18) and R a01 and structural units in which the methyl group corresponding to the formula (a1-0-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group, and structural units represented by any of formulas (a1-0-1) to (a1-0-10), (a1-0-13) and (a1-0-14) are preferred. TIFF2023143845000083.tif88160

[0102] Examples of the structural unit (a1-1) include structural units derived from monomers described in JP-A-2010-204646. Among these, structural units represented by any one of formulas (a1-1-1) to (a1-1-7) and R in the structural unit (a1-1) are preferred. a4 A structural unit in which the methyl group corresponding to the formula (a1-1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group is preferred, and a structural unit represented by any one of formulas (a1-1-1) to (a1-1-4) is more preferred. TIFF2023143845000084.tif38168

[0103] The structural unit (a1-2) includes a structural unit represented by any one of formulas (a1-2-1) to (a1-2-14) and R a5and structural units in which the methyl group corresponding to the formula (a1-2-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group, and structural units represented by any of formulas (a1-2-2), (a1-2-5), (a1-2-6), and (a1-2-10) to (a1-2-14) are preferred. TIFF2023143845000085.tif67163

[0104] When the resin (A) or the like contains the structural unit (a1-0) and / or the structural unit (a1-1) and / or the structural unit (a1-2), the total content of these, based on all structural units in the resin (A) or the like, can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, and even more preferably 30 mol% or more. Also, the total content can be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, and even more preferably 70 mol% or less. Specifically, the total content can be 10 to 95 mol%, preferably 15 to 90 mol%, more preferably 20 to 85 mol%, even more preferably 25 to 70 mol%, and even more preferably 30 to 70 mol%. When the resin (A) or the like contains the structural unit (a1-0), the content thereof is 5 mol % or more, preferably 10 mol % or more, based on the total structural units of the resin (A) or the like. Also, the content is 80 mol % or less, preferably 75 mol % or less, and more preferably 70 mol % or less. Specifically, the content is 5 to 80 mol %, preferably 5 to 75 mol %, and more preferably 10 to 70 mol %. When the resin (A) or the like contains the structural unit (a1-1) and / or the structural unit (a1-2), the total content of these structural units, based on all structural units in the resin (A) or the like, can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, and even more preferably 30 mol% or more. Also, the total content can be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, still more preferably 75 mol% or less, and even more preferably 70 mol% or less. Specifically, the total content can be 10 to 90 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, even more preferably 20 to 80 mol%, even more preferably 20 to 75 mol%, and even more preferably 20 to 70 mol%.

[0105] An example of the structural unit (a1) having the group (2) is a structural unit represented by formula (a1-4) (hereinafter, sometimes referred to as "structural unit (a1-4)"). TIFF2023143845000086.tif4564[In formula (a1-4), R a32 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a33 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a30 is a single bond or * -X a31 -(A a32 -X a32 ) nc - represents -R a32 represents the bonding site with the carbon atom to which it is bonded. A a32 represents an alkanediyl group having 1 to 8 carbon atoms. X a31 and X a32 each independently represents -O-, -CO-O- or -O-CO-. nc represents 0 or 1. la represents an integer of 0 to 4. When la is an integer of 2 or more, a plurality of R a33 may be the same or different from each other. R a34 and R a35 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a36 represents a hydrocarbon group having 1 to 20 carbon atoms, or R a35 and R a36 are bonded to each other to form, together with the -CO- to which they are bonded, a divalent hydrocarbon group having 2 to 20 carbon atoms, and the hydrocarbon group and the -CH2- contained in the divalent hydrocarbon group may be replaced with -O- or -S-.]

[0106] R a32 and R a33 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, and a bromine atom. R a32 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in the formula (I) include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, and a perfluorohexyl group. R a32 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a33Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a33 Examples of the alkoxy group in include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. R a33 Examples of the alkoxyalkyl group in the formula (I) include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group. R a33 Examples of the alkoxyalkoxy group in include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group. R a33 Examples of the alkylcarbonyl group in the formula (I) include an acetyl group, a propionyl group, a butyryl group, etc. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group. R a33Examples of the alkylcarbonyloxy group in the formula (I) include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group. R a33 is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0107] *-X a31 -(A a32 -X a32 ) nc -Examples include *-O-, *-CO-O-, *-O-CO-, *-CO-OA a32 -CO-O-, *-O-CO-A a32 -O-, *-OA a32 -CO-O-, *-CO-OA a32 -O-CO-, *-O-CO-A a32 -O-CO-, and *-CO-O- and *-CO-OA are particularly mentioned. a32 -CO-O- or *-OA a32 -CO-O- is preferred.

[0108] 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, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. A a32 is preferably a methylene group or an ethylene group.

[0109] A a30is a single bond, *-CO-O- or *-CO-OA a32 -CO-O- is preferred, a single bond, *-CO-O- or *-CO-O-CH2-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.

[0110] la is preferably 0, 1 or 2, more preferably 0 or 1, and even more preferably 0. R a34 , R a35 and R a36 Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group consisting of a combination thereof. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (* indicates a bonding site): TIFF2023143845000087.tif10151 Examples of aromatic hydrocarbon groups include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. In particular, R a36 Examples of the group include an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these groups.

[0111] R a34 is preferably a hydrogen atom. R a35 is preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a methyl group or an ethyl group. R a36 The hydrocarbon group in R is preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these, and more preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms. a36 The alkyl group and alicyclic hydrocarbon group in R are preferably unsubstituted. a36 The aromatic hydrocarbon group in is preferably an aromatic ring having an aryloxy group having 6 to 10 carbon atoms. -OC(R a34 )(R a35 )-OR a36is eliminated on contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxy group. -OC(R a34 )(R a35 )-OR a36 is preferably bonded to the m-position or p-position of the benzene ring, and more preferably to the p-position.

[0112] Examples of the structural unit (a1-4) include structural units derived from monomers described in JP-A-2010-204646. Preferred are structural units represented by formulas (a1-4-1) to (a1-4-24) and R in the structural unit (a1-4). a32 and more preferably, the structural units represented by formulae (a1-4-1) to (a1-4-5), (a1-4-10), (a1-4-13), (a1-4-14), (a1-4-19), and (a1-4-20). TIFF2023143845000088.tif126158

[0113] When the resin (A) or the like contains the structural unit (a1-4), the content thereof is preferably 3 to 80 mol %, more preferably 5 to 75 mol %, even more preferably 7 to 70 mol %, still more preferably 7 to 65 mol %, and even more preferably 10 to 60 mol %, based on the total amount of all structural units in the resin (A) or the like.

[0114] Examples of the structural unit derived from a (meth)acrylic monomer having the group (2) include a structural unit represented by formula (a1-5) (hereinafter, sometimes referred to as "structural unit (a1-5)"). TIFF2023143845000089.tif4558[In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom. Z a1 is a single bond or -(CH2)h3 -CO-L 54 -, h3 represents an integer of 1 to 4, * represents L 51 represents the binding site with L 51 , L 52 , L 53 and L 54 each independently represents -O- or -S-. s1 represents an integer of 1 to 3. s1' represents an integer of 0 to 3.

[0115] Examples of halogen atoms include fluorine atoms and chlorine atoms, with fluorine atoms being preferred. Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a fluoromethyl group, and a trifluoromethyl group. In formula (a1-5), R a8 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. L 51 is preferably an oxygen atom. L 52 and L 53 Among these, it is preferred that one is —O— and the other is —S—. s1 is preferably 1. s1' is preferably an integer of 0 to 2. Z a1 is preferably a single bond or —CH2—CO—O—.

[0116] Examples of the structural unit (a1-5) include structural units derived from monomers described in JP-A-2010-61117. Among these, the structural units represented by formulas (a1-5-1) to (a1-5-4) are preferred, and the structural unit represented by formula (a1-5-1) or (a1-5-2) is more preferred. TIFF2023143845000090.tif33133

[0117] When the resin (A) or the like contains the structural unit (a1-5), the content thereof is preferably 1 to 50 mol %, more preferably 3 to 45 mol %, even more preferably 5 to 40 mol %, and even more preferably 5 to 30 mol %, based on all structural units of the resin (A) or the like.

[0118] Further, examples of the structural unit (a1) include the following structural units. TIFF2023143845000091.tif31162

[0119] When the resin (A) or the like contains structural units such as (a1-3-1) to (a1-3-7), the content thereof is preferably 10 to 95 mol %, more preferably 15 to 90 mol %, even more preferably 20 to 85 mol %, even more preferably 20 to 70 mol %, and particularly preferably 20 to 60 mol %, based on all structural units in the resin (A) or the like.

[0120] Further, examples of the structural unit (a1) include the following structural units. TIFF2023143845000092.tif5195 When the resin (A) or the like contains structural units such as (a1-6-1) to (a1-6-3), the content thereof is preferably 10 to 60 mol %, more preferably 15 to 55 mol %, even more preferably 20 to 50 mol %, even more preferably 20 to 45 mol %, and particularly preferably 20 to 40 mol %, based on the total structural units of the resin (A) or the like.

[0121] <Structural unit(s)> The structural unit (s) is derived from a monomer (hereinafter sometimes referred to as "monomer (s)") that does not have an acid labile group. As the monomer from which the structural unit (s) is derived, a monomer that does not have an acid labile group known in the resist field can be used. The structural unit (s) preferably has a hydroxy group or a lactone ring. The use of a resin containing a structural unit having a hydroxy group but no acid labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring but no acid labile group (hereinafter sometimes referred to as "structural unit (a3)") in the resist composition of the present invention can improve the resolution of the resist pattern and the adhesion to the substrate.

[0122] <Structural unit (a2)> The structural unit (a2) is a structural unit represented by formula (a2) and has an alcoholic hydroxy group or a phenolic hydroxy group. TIFF2023143845000093.tif3095[In formula (a2), 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. A a50 is a single bond or * -X a51 -(A a52 -X a52 ) nb - represents -R a50 represents the bonding site with the carbon atom to which it is bonded. A a52 represents an alkanediyl group having 1 to 8 carbon atoms. X a51 and X a52 each independently represents -O-, -CO-O- or -O-CO-. nb represents 0 or 1. W a50 represents a cyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent. L a50 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms which may contain a fluorine atom. ma50 represents an integer from 1 to 5. R a50 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, and a bromine atom. R a50Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, and a perfluorohexyl group. The number of carbon atoms in the alkyl group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. R 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.

[0123] A a50 A in a52 Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The number of carbon atoms in the alkanediyl group is preferably 1 to 6, more preferably 1 to 4, even more preferably 1 to 3, and even more preferably 1 or 2. A a52 is preferably a methylene group or an ethylene group. *-X a51 -(A a52 -X a52 ) nb -Examples include *-O-, *-CO-O-, *-O-CO-, *-CO-OA a52 -CO-O-, *-O-CO-A a52 -O-, *-OA a52-CO-O-, *-CO-OA a52 -O-CO-, *-O-CO-A a52 -O-CO-, and *-CO-O- and *-CO-OA are particularly mentioned. a52 -CO-O- or *-OA a52 -CO-O- is preferred. A a50 is a single bond, *-CO-O- or *-CO-OA a52 -CO-O- is preferred, a single bond, *-CO-O- or *-CO-O-CH2-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.

[0124] W a50 Examples of the cyclic hydrocarbon group include a divalent alicyclic hydrocarbon group and a divalent aromatic hydrocarbon group. W a50 Examples of the monocyclic divalent alicyclic hydrocarbon group in the formula (I) include monocyclic cycloalkanediyl groups such as cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl. Examples of the polycyclic divalent alicyclic hydrocarbon group in the formula (I) include polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, and adamantane-2,6-diyl. The alicyclic hydrocarbon group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms. W a50 Examples of the divalent aromatic hydrocarbon group in the formula include a phenylene group and a phenylene group. The aromatic hydrocarbon group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms. W a50Examples of the substituent that the cyclic hydrocarbon group having 5 to 12 carbon atoms may have include a halogen atom, a hydroxy group, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. a50 The number of substituents that may be present may be one or two or more. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. Examples of haloalkyl groups include trifluoromethyl, difluoromethyl, perfluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, perfluoropropyl, 2,2,3,3,3-pentafluoropropyl, perfluorobutyl, 1,1,2,2,3,3,4,4-octafluorobutyl, perfluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, perfluorohexyl, chloromethyl, bromomethyl, and iodomethyl. The number of carbon atoms in the haloalkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group. The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. Examples of the alkoxyalkyl group include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group. Examples of the alkoxyalkoxy group include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group. W a50 The substituent of the cyclic hydrocarbon group is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0125] L a50Examples of the chain hydrocarbon group having 1 to 12 carbon atoms include straight-chain alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl. branched alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, 1-methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-dimethylpropane-1,3-diyl, pentane-2,4-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. The chain hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, even more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms. L a50 may have one or more fluorine atoms. ma50 is preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.

[0126] When producing a resist pattern from the resist composition of the present invention, if a high-energy ray such as a KrF excimer laser (248 nm), an electron beam, or EUV (extreme ultraviolet) is used as an exposure light source, the structural unit (a2) preferably has a phenolic hydroxy group, and more preferably the structural unit (a2-A) described below. Furthermore, if an ArF excimer laser (193 nm) or the like is used, the structural unit (a2) preferably has an alcoholic hydroxy group, and more preferably the structural unit (a2-1) described below. The structural unit (a2) may contain one type alone or two or more types.

[0127] In the structural unit (a2), an example of a structural unit having a phenolic hydroxy group is a structural unit represented by formula (a2-A) (hereinafter, sometimes referred to as "structural unit (a2-A)"). TIFF2023143845000094.tif4653[In formula (a2-A), R a50 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a50 is a single bond or *-X a51 -(A a52 -X a52 ) nb - represents -R a50 represents the bonding site with the carbon atom to which it is bonded. A a52 represents an alkanediyl group having 1 to 8 carbon atoms. X a51 and X a52 each independently represents -O-, -CO-O- or -O-CO-. nb represents 0 or 1. mb represents an integer of 0 to 4. When mb is an integer of 2 or more, a plurality of R a51 may be the same or different from each other.

[0128] R a50 and A a50 The groups include the same groups as those exemplified in formula (a2). R a51 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, and a bromine atom. R a51Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a51 Examples of the alkoxy group in include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. R a51 Examples of the alkoxyalkyl group in the formula (I) include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group. R a51 Examples of the alkoxyalkoxy group in include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group. R a51 Examples of the alkylcarbonyl group in the formula (I) include an acetyl group, a propionyl group, a butyryl group, etc. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group. R a51 Examples of the alkylcarbonyloxy group in the formula (I) include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group. R a51 is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0129] mb is preferably 0, 1 or 2, and more preferably 0 or 1. At least one hydroxy group is preferably bonded to the m-position or p-position of the benzene ring. When two or more hydroxy groups are contained, two hydroxy groups are preferably bonded to the m-position and p-position, respectively.

[0130] Examples of the structural unit (a2-A) include structural units derived from monomers described in JP-A Nos. 2010-204634 and 2012-12577. The structural unit (a2-A) includes structural units represented by formulas (a2-2-1) to (a2-2-24) and R in the structural unit (a2-A) in the structural units represented by formulas (a2-2-1) to (a2-2-24). a50 The structural unit (a2-A) includes structural units represented by formulas (a2-2-1) to (a2-2-4), structural units represented by formula (a2-2-6), structural units represented by formula (a2-2-8), structural units represented by formulas (a2-2-12) to (a2-2-18), and structural units represented by formulas (a2-2-1) to (a2-2-4), structural units represented by formula (a2-2-6), structural units represented by formula (a2-2-8), and structural units represented by formulas (a2-2-12) to (a2-2-18), in which R in the structural unit (a2-A) is a50In the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-4), the structural unit represented by formula (a2-2-8), the structural unit represented by formula (a2-2-12) to formula (a2-2-14), the structural unit represented by formula (a2-2-18), and the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-4), the structural unit represented by formula (a2-2-8), the structural unit represented by formula (a2-2-12) to formula (a2-2-14), and the structural unit represented by formula (a2-2-18), a50 In the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-4), the structural unit represented by formula (a2-2-8), and the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-4), and the structural unit represented by formula (a2-2-8), a50 More preferably, the structural unit is a structural unit in which a methyl group corresponding to the following formula is replaced with a hydrogen atom: TIFF2023143845000095.tif79169

[0131] When the structural unit (a2-A) is contained in the resin (A) or the like, the content of the structural unit (a2-A) relative to all structural units is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 15 mol% or more, and even more preferably 20 mol% or more. It is also preferably 80 mol% or less, more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, even more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%. The structural unit (a2-A) can be incorporated into the resin (A) by, for example, polymerizing the structural unit (a1-4) and then treating with an acid such as p-toluenesulfonic acid. Alternatively, the structural unit (a2-A) can be incorporated into the resin (A) by polymerizing the structural unit (a1-4) and then treating with an alkali such as tetramethylammonium hydroxide.

[0132] Examples of the structural unit (a2-A) include a structural unit represented by the following formula (a2-A1) (hereinafter sometimes referred to as "structural unit (a2-A1)") and a structural unit represented by the following formula (a2-A2) (hereinafter sometimes referred to as "structural unit (a2-A2)"). TIFF2023143845000096.tif52136 [In formula (a2-A1) and formula (a2-A2), R a50 and A a50 have the same meaning as in formula (a2). mb1 represents an integer of 0 to 4. R a52 represents a halogen atom. R a53 represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. mb2 and mb3 each independently represent an integer of 0 to 4, and when mb2 is 2 or more, a plurality of R a52 may be the same or different, and when mb3 is 2 or more, multiple R a53 may be the same or different, and satisfy 1≦mb2+mb3≦4. R a52 The halogen atoms in a50 The substituents of the cyclic hydrocarbon group and R a51 The halogen atoms in R are the same as those in R. a52 The halogen atom is preferably a fluorine atom or an iodine atom. Ra53 The alkyl group having 1 to 6 carbon atoms, the alkoxy group having 1 to 6 carbon atoms, the alkoxyalkyl group having 2 to 12 carbon atoms, the alkoxyalkoxy group having 2 to 12 carbon atoms, the alkylcarbonyl group having 2 to 4 carbon atoms, the alkylcarbonyloxy group having 2 to 4 carbon atoms, the acryloyloxy group or the methacryloyloxy group is, respectively, W a50 The substituents of the cyclic hydrocarbon group and R a51 Examples thereof include the same as the alkyl group, alkoxy group, alkoxyalkyl group, alkoxyalkoxy group, alkylcarbonyl group, alkylcarbonyloxy group, acroyloxy group, and methacryloyloxy group in the above formula (1), more preferably a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a methoxy group or an ethoxyethoxy group. mb1 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and further preferably 0 or 1. mb2 is preferably an integer of 0 to 3, more preferably an integer of 1 to 3, and further preferably 1 or 2. mb3 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and further preferably 0 or 1.

[0133] An example of the structural unit (a2) having an alcoholic hydroxy group is a structural unit represented by formula (a2-1) (hereinafter, sometimes referred to as "structural unit (a2-1)"). TIFF2023143845000097.tif4562[In formula (a2-1), L a3 is -O- or *-O-(CH2) k2 represents -CO-O-, k2 represents an integer of 1 to 7. * represents the bonding site with —CO—. R a14 represents a hydrogen atom or a methyl group. R a15 and R a16 each independently represents a hydrogen atom, a methyl group, or a hydroxy group. o1 represents an integer between 0 and 10.

[0134] In equation (a2-1), L a3 is preferably -O-, -O-(CH2) f1 It is —CO—O— (wherein f1 represents an integer of 1 to 4), and more preferably —O—. R a14 is preferably a methyl group. R a15 is preferably a hydrogen atom. R a16 is preferably a hydrogen atom or a hydroxy group. o1 is preferably an integer of 0 to 3, and more preferably 0 or 1.

[0135] Examples of the structural unit (a2-1) include structural units derived from monomers described in JP 2010-204646 A. A structural unit represented by any one of formulas (a2-1-1) to (a2-1-6) is preferred, a structural unit represented by any one of formulas (a2-1-1) to (a2-1-4) is more preferred, and a structural unit represented by formula (a2-1-1) or formula (a2-1-3) is even more preferred. TIFF2023143845000098.tif53146

[0136] When the resin (A) or the like contains the structural unit (a2-1), the content thereof is 1 mol% or more, preferably 2 mol% or more, based on the total structural units of the resin (A) or the like. It may also be 45 mol% or less, preferably 40 mol% or less, more preferably 35 mol% or less, even more preferably 20 mol% or less, and even more preferably 10 mol% or less. Specifically, it may be 1 to 45 mol%, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, even more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol%.

[0137] An example of the structural unit (a2) having an alcoholic hydroxy group is a structural unit represented by formula (a2-B) (hereinafter, sometimes referred to as "structural unit (a2-B)"). TIFF2023143845000099.tif50104[In formula (a2-B), R a50 and A a50 have the same meaning as in formula (a2). R a54 and R a55 each independently represents a fluorinated alkyl group having 1 to 4 carbon atoms. L a51 represents a single bond or an alkanediyl group having 1 to 3 carbon atoms, and the alkanediyl group may be substituted with a fluorine atom. R a56 represents a halogen atom, a hydroxy group, a haloalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkyl group may be replaced by -O- or -CO-. mb4 represents an integer of 1 to 3, and when mb4 is 2 or more, multiple R a54 , R a55 and L a51 may be the same or different from each other. mb5 represents an integer from 0 to 4, and when mb5 is 2 or more, multiple R a56 may be the same or different, provided that 1≦mb4+mb5≦5.

[0138] R a54 and R a55 Examples of the fluorinated alkyl groups having 1 to 4 carbon atoms in R each independently include a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, and a 4,4,4-trifluorobutyl group. a54 and R a55 As the aryl group, a trifluoromethyl group is preferred. L a51 Examples of the alkanediyl group having 1 to 3 carbon atoms include a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group. a51 is preferably a single bond or a methylene group. R a56Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R a56 The haloalkyl group having 1 to 4 carbon atoms represents an alkyl group having 1 to 4 carbon atoms and a halogen atom, and examples thereof include a chloromethyl group, a bromomethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a perfluorobutyl group. R a56 Examples of the alkyl group having 1 to 12 carbon atoms in the formula include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, octyl group, nonyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 9, more preferably 1 to 6, and even more preferably 1 to 4. R a56 When -CH2- in the alkyl group represented by R is replaced with -O- or -CO-, the number of carbon atoms before the replacement is the total number of carbon atoms in the alkyl group. a56 may have a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a carboxyl group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), an alkoxy group having 1 to 11 carbon atoms (a group in which -CH2- in an alkyl group having 2 to 12 carbon atoms is replaced with -O-), an alkoxycarbonyl group having 2 to 11 carbon atoms (a group in which -CH2-CH2- in an alkyl group having 3 to 12 carbon atoms is replaced with -O-CO-), an alkylcarbonyl group having 2 to 12 carbon atoms (a group in which -CH2- in an alkyl group having 2 to 12 carbon atoms is replaced with -CO-), or an alkylcarbonyloxy group having 2 to 11 carbon atoms (a group in which -CH2-CH2- in an alkyl group having 3 to 12 carbon atoms is replaced with -CO-O-). R a56 Among these, a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced by -O- or -CO-) is preferred. mb4 is preferably 1 or 2, and more preferably 1. Even more preferably, mb4 is 1 and the group in parentheses is bonded to the para position. mb5 is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0139] The structural unit (a2-B) is more preferably a structural unit represented by the following formula (a2-B1) (hereinafter, sometimes referred to as "structural unit (a2-B1)"). TIFF2023143845000100.tif4686[In formula (a2-B1), R a57 represents a hydrogen atom or a methyl group. A a53 is a single bond or * -CO-O-, * represents -R a57 represents the bonding site with the carbon atom to which it is bonded. R a56 , mb4 and mb5 have the same meanings as in formula (a2-B).

[0140] In formula (a2-B1), R a57 is preferably a hydrogen atom. A a53 is preferably a single bond.

[0141] Examples of the structural unit (a2-B) include the structural units shown below. TIFF2023143845000101.tif62168

[0142] In the structural units represented by formulae (a2-B-1) to (a2-B-8), R a57 In the structural units represented by formulae (a2-B-9) to (a2-B-16), the structural unit in which the hydrogen atom corresponding to R is replaced with a methyl group is also a57Specific examples of the structural unit (a2-B) include structural units in which a methyl group corresponding to the following formula is replaced with a hydrogen atom. Among these, structural units represented by formulas (a2-B-1) to (a2-B-8) are preferred, structural units represented by formulas (a2-B-1) to (a2-B-4) are more preferred, and structural unit represented by formula (a2-B-1) is even more preferred.

[0143] When the resin (A) or the like contains the structural unit (a2-B), its content relative to all structural units in the resin (A) or the like is preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more. It is also preferably 80 mol% or less, more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, even more preferably 10 to 70 mol%, and even more preferably 10 to 65 mol%.

[0144] <Structural unit (a3)> The lactone ring contained in the structural unit (a3) ​​may be a monocyclic ring such as a β-propiolactone ring, a γ-butyrolactone ring, or a δ-valerolactone ring, or a condensed ring of a monocyclic lactone ring with another ring. Preferred examples include a γ-butyrolactone ring, an adamantane lactone ring, or a bridged ring containing a γ-butyrolactone ring structure (for example, a structural unit represented by the following formula (a3-2)).

[0145] The structural unit (a3) ​​is preferably a structural unit represented by formula (a3-1), formula (a3-2), formula (a3-3), or formula (a3-4). One of these may be contained alone, or two or more may be contained. TIFF2023143845000102.tif50161 [In formula (a3-1), formula (a3-2), formula (a3-3) and formula (a3-4), L a4 , L a5 and L a6 are each independently -O- or -O-(CH2) k3It represents a group represented by —CO—O— (k3 represents an integer of 1 to 7). L a7 -O-, *-OL a8 -O-, *-OL a8 -CO-O-, *-OL a8 -CO-OL a9 -CO-O- or *-OL a8 -O-CO-L a9 Represents -O-. L a8 and L a9 each independently represents an alkanediyl group having 1 to 6 carbon atoms. * indicates the bonding site with the carbonyl group. R a18 , R a19 , R a20 and R a24 each independently represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom, or a halogen atom. X a3 represents -CH2- or an oxygen atom. R a21 represents an aliphatic hydrocarbon group having 1 to 4 carbon atoms. R a22 , R a23 and R a25 each independently represents a carboxy group, a cyano group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms. p1 represents an integer of 0 to 5. q1 represents an integer of 0 to 3. r1 represents an integer of 0 to 3. w1 represents an integer of 0 to 8. When p1, q1, r1 and / or w1 are 2 or more, multiple R a21 , R a22 , R a23 and / or R a25 may be the same or different from each other.

[0146] R a21 , R a22 , R a23 and R a25Examples of the aliphatic hydrocarbon group in include alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, and a tert-butyl group. R a18 , R a19 , R a20 and R a24 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R a18 , R a19 , R a20 and R a24 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group, and preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. R a18 , R a19 , R a20 and R a24 Examples of the alkyl group having a halogen atom in the formula (I) include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group.

[0147] L a8 and L a9 Examples of the alkanediyl group in the formula (I) include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group.

[0148] In formulas (a3-1) to (a3-3), L a4 ~L a6are each independently preferably -O- or -O-(CH2) k3 In -CO-O-, k3 is a group in which k3 is any integer of 1 to 4, more preferably -O- and *-O-CH2-CO-O-, and even more preferably an oxygen atom. R a18 ~R a21 is preferably a methyl group. R a22 and R a23 are each independently preferably a carboxy group, a cyano group, or a methyl group. p1, q1 and r1 each independently represent an integer of preferably 0 to 2, and more preferably 0 or 1.

[0149] In formula (a3-4), R a24 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a25 is preferably a carboxy group, a cyano group or a methyl group. L a7 is preferably -O- or *-OL a8 It is —CO—O—, and more preferably —O—, —O—CH 2 —CO—O— or —O—C 2 H 4 —CO—O—. w1 is preferably an integer of 0 to 2, and more preferably 0 or 1. In particular, the formula (a3-4) is preferably the formula (a3-4)'. TIFF2023143845000103.tif3848 (in the formula, R a24 , L a7 has the same meaning as above.)

[0150] Examples of the structural unit (a3) ​​include structural units derived from monomers described in JP 2010-204646 A, JP 2000-122294 A, and JP 2012-41274 A. Examples of the structural unit (a3) ​​include structural units represented by any of formulas (a3-1-1), (a3-1-2), (a3-2-1), (a3-2-2), (a3-3-1), (a3-3-2), and (a3-4-1) to (a3-4-12), and in the structural units, R in formulas (a3-1) to (a3-4) a18 , R a19 , R a20 and R a24 A structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom is preferred.

[0151] TIFF2023143845000104.tif116165

[0152] When the resin (A) or the like contains the structural unit (a3), the total content thereof is, relative to all structural units in the resin (A) or the like, 1 mol % or more, preferably 3 mol % or more, more preferably 5 mol % or more, and even more preferably 10 mol % or more. Also, it is, for example, 70 mol % or less, preferably 65 mol % or less, and more preferably 60 mol % or less. Specifically, it is, for example, 1 to 70 mol %, preferably 3 to 65 mol %, and more preferably 5 to 60 mol %. The content of the structural unit (a3-1), the structural unit (a3-2), the structural unit (a3-3), or the structural unit (a3-4) is preferably 1 mol% or more, more preferably 3 mol% or more, and even more preferably 5 mol% or more, based on the total structural units of the resin (A). It is also preferably 60 mol% or less, more preferably 55 mol% or less, and even more preferably 50 mol% or less. Specifically, it is preferably 1 to 60 mol%, more preferably 3 to 55 mol%, and even more preferably 5 to 50 mol%.

[0153] <Structural unit (a4)> Examples of the structural unit (a4) include the following structural units. TIFF2023143845000105.tif2962[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 halogen atom, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.] R 42 Examples of the saturated hydrocarbon group represented by the formula (I) include a chain saturated hydrocarbon group, a monocyclic or polycyclic alicyclic saturated hydrocarbon group, and a group formed by combining these groups.

[0154] Examples of the chain saturated hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group. Examples of the monocyclic or polycyclic alicyclic saturated hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group; and polycyclic alicyclic saturated hydrocarbon groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following groups (* indicates a bonding site): TIFF2023143845000106.tif10146 Examples of groups formed by this combination include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic saturated hydrocarbon groups, such as -alkanediyl group-alicyclic saturated hydrocarbon group, -alicyclic saturated hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic saturated hydrocarbon group-alkyl group.

[0155] Examples of the structural unit (a4) include a structural unit represented by formula (a4-0), a structural unit represented by formula (a4-1), and a structural unit represented by formula (a4-4). TIFF2023143845000107.tif4551[In formula (a4-0), R 54 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 perfluorocycloalkanediyl group having 3 to 12 carbon atoms. R 64 represents a hydrogen atom or a fluorine atom.

[0156] L 4a Examples of the alkanediyl group in the formula (I) include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, and a butane-1,4-diyl group, and branched alkanediyl groups such as an ethane-1,1-diyl group, a propane-1,2-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group.

[0157] L 3a Examples of the perfluoroalkanediyl group in the formula (I) include a difluoromethylene group, a perfluoroethylene group, a perfluoroethylfluoromethylene group, a perfluoropropane-1,3-diyl group, a perfluoropropane-1,2-diyl group, a perfluoropropane-2,2-diyl group, a perfluorobutane-1,4-diyl group, a perfluorobutane-2,2-diyl group, a perfluorobutane-1,2-diyl group, a perfluoropentane-1,5-diyl group, a perfluoropentane-2,2-diyl group, a perfluoropentane-3 ,3-diyl group, perfluorohexane-1,6-diyl group, perfluorohexane-2,2-diyl group, perfluorohexane-3,3-diyl group, perfluoroheptane-1,7-diyl group, perfluoroheptane-2,2-diyl group, perfluoroheptane-3,4-diyl group, perfluoroheptane-4,4-diyl group, perfluorooctane-1,8-diyl group, perfluorooctane-2,2-diyl group, perfluorooctane-3,3-diyl group, and perfluorooctane-4,4-diyl group. L 3aExamples of the perfluorocycloalkanediyl group in the formula (I) include a perfluorocyclohexanediyl group, a perfluorocyclopentanediyl group, a perfluorocycloheptanediyl group, and a perfluoroadamantanediyl group.

[0158] L 4a is preferably a single bond, a methylene group, or an ethylene group, and more preferably a single bond or a methylene group. L 3a is preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0159] The structural unit (a4-0) includes the structural units shown below and R in the structural unit (a4-0) in the structural units shown below. 54 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2023143845000108.tif98165

[0160] TIFF2023143845000109.tif4866[In formula (a4-1), R a41 represents a hydrogen atom or a methyl group. R a42 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. A a41 represents an alkanediyl group having 1 to 6 carbon atoms which may have a substituent or a group represented by formula (a-g1), a41 and R a42 At least one of the groups has a halogen atom (preferably a fluorine atom) as a substituent. TIFF2023143845000110.tif1487 [In formula (a-g1), s represents 0 or 1. A a42 and A a44each independently represents a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. A a43 represents a single bond or a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. X a41 and X a42 each independently represents -O-, -CO-, -CO-O- or -O-CO-. However, A a42 , A a43 , A a44 , X a41 and X a42 The total number of carbon atoms is 7 or less. * indicates the binding site, and the * on the right is -O-CO-R a42 ]

[0161] R a42 Examples of the saturated hydrocarbon group in include a chain saturated hydrocarbon group, a monocyclic or polycyclic alicyclic saturated hydrocarbon group, and groups formed by combining these groups.

[0162] Examples of the chain saturated hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group. Examples of the monocyclic or polycyclic alicyclic saturated hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group; and polycyclic alicyclic saturated hydrocarbon groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following groups (* indicates a bonding site): TIFF2023143845000111.tif10160 Examples of groups formed by this combination include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic saturated hydrocarbon groups, such as -alkanediyl group-alicyclic saturated hydrocarbon group, -alicyclic saturated hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic saturated hydrocarbon group-alkyl group.

[0163] R a42 The substituent that may be included in the formula (a-g3) is at least one selected from the group consisting of a halogen atom and a group represented by formula (a-g3): Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferred. TIFF2023143845000112.tif855[In formula (a-g3), X a43 represents an oxygen atom, a carbonyl group, *-O-CO- or *-CO-O-. A a45 represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. * denotes R a42 represents the binding site with However, R a42 -X a43 -A a45 In R a42 If A does not have a halogen atom, a45 represents a saturated hydrocarbon group having 1 to 17 carbon atoms and at least one halogen atom.

[0164] A a45 Examples of the saturated hydrocarbon group in the formula (I) include alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, a dodecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group; Examples include monocyclic alicyclic hydrocarbon groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; and polycyclic alicyclic hydrocarbon groups such as decahydronaphthyl, adamantyl, and norbornyl groups, and the following groups (* indicates a bonding site): TIFF2023143845000113.tif10160 Examples of groups formed by combination include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic hydrocarbon group-alkyl group.

[0165] R a42 is preferably a saturated hydrocarbon group which may have a halogen atom, and more preferably a saturated hydrocarbon group having an alkyl group having a halogen atom and / or a group represented by formula (a-g3). R a42 When 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 perfluorocycloalkyl group, still more preferably a perfluoroalkyl group having 1 to 6 carbon atoms, and particularly preferably a perfluoroalkyl group having 1 to 3 carbon atoms. Examples of perfluoroalkyl groups include a perfluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, and a perfluorooctyl group. Examples of perfluorocycloalkyl groups include a perfluorocyclohexyl group. R a42 is a saturated hydrocarbon group having a group represented by formula (a-g3), the number of carbon atoms contained in the group represented by formula (a-g3) is a42 The total number of carbon atoms is preferably 15 or less, more preferably 12 or less. When the group represented by formula (a-g3) is contained as a substituent, the number thereof is preferably 1.

[0166] R a42 is a saturated hydrocarbon group having a group represented by formula (a-g3), R a42 is more preferably a group represented by formula (a-g2). TIFF2023143845000114.tif871[In formula (a-g2), 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 A a46 represents the binding site with ). A a47represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. However, A a46 , A a47 and X a44 The total number of carbon atoms in A is 18 or less. a46 and A a47 At least one of the groups has at least one halogen atom. * indicates the bonding site with the carbonyl group.]

[0167] A a46 The saturated hydrocarbon group preferably has 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. A a47 The saturated hydrocarbon group preferably has 4 to 15 carbon atoms, more preferably 5 to 12 carbon atoms, and A a47 is more preferably a cyclohexyl group or an adamantyl group.

[0168] A preferred structure of the group represented by formula (a-g2) is the following structure (* indicates the bonding site with the carbonyl group): TIFF2023143845000115.tif14164

[0169] A a41 Examples of the alkanediyl group in the formula (I) include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and branched alkanediyl groups such as propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-methylbutane-1,4-diyl, and 2-methylbutane-1,4-diyl. A a41 Examples of the substituent in the alkanediyl group represented by the formula (I) include a hydroxy group and an alkoxy group having 1 to 6 carbon atoms. A a41 is preferably an alkanediyl group having 1 to 4 carbon atoms, more preferably an alkanediyl group having 2 to 4 carbon atoms, and even more preferably an ethylene group.

[0170] A in the group represented by formula (a-g1) a42 , A a43 and A a44 Examples of the divalent saturated hydrocarbon group represented by include a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and a divalent saturated hydrocarbon group formed by combining an alkanediyl group with a divalent alicyclic saturated hydrocarbon group. Specific examples include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group. A a42 , A a43 and A a44 Examples of the substituent of the divalent saturated hydrocarbon group represented by the formula include a hydroxy group and an alkoxy group having 1 to 6 carbon atoms. Preferably, s is 0.

[0171] In the group represented by formula (a-g1), X a42 In the following examples, * and ** each represent a bonding site, and ** represents -O-CO-R a42 This is the binding site for TIFF2023143845000116.tif47140

[0172] The structural unit represented by formula (a4-1) includes the structural units shown below and R in the structural unit represented by formula (a4-1) in the structural units shown below. a41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. JPEG2023143845000117.jpg99145

[0173] TIFF2023143845000118.tif132150

[0174] Examples of the structural unit represented by formula (a4-1) include a structural unit represented by formula (a4-2) and a structural unit represented by formula (a4-3). TIFF2023143845000119.tif4356[In formula (a4-2), R f5 represents a hydrogen atom or a methyl group. L 44 represents an alkanediyl group having 1 to 6 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-. R f6 represents a saturated hydrocarbon group having 1 to 20 carbon atoms and containing a fluorine atom. However, L 44 and R f6 The maximum total carbon number is 21.]

[0175] L 44 The alkanediyl group having 1 to 6 carbon atoms is A a41 Examples of the groups include the same groups as those exemplified in R f6 The saturated hydrocarbon group of R 42 Examples of the groups include the same groups as those exemplified in L 44 The alkanediyl group in the formula (I) is preferably an alkanediyl group having 2 to 4 carbon atoms, more preferably an ethylene group.

[0176] Examples of the structural unit represented by formula (a4-2) include structural units represented by formulas (a4-1-1) to (a4-1-11). f5 The structural unit represented by formula (a4-2) also includes a structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom:

[0177] TIFF2023143845000120.tif5671[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 contain a fluorine atom. X f12 represents *-O-CO- or *-CO-O- (* represents A f13 represents the binding site with ). A f14 represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may contain a fluorine atom. However, A f13 and A f14 At least one of L has a fluorine atom, 5 , A f13 and A f14 The total number of carbon atoms in a molecule is limited to 20.

[0178] L 5 The alkanediyl group in a41 Examples of the alkanediyl group include the same groups as those exemplified as the alkanediyl group.

[0179] A f13 The divalent saturated hydrocarbon group optionally having a fluorine atom in the formula (I) is preferably a divalent chain saturated hydrocarbon group optionally having a fluorine atom and a divalent alicyclic saturated hydrocarbon group optionally having a fluorine atom, and more preferably a perfluoroalkanediyl group. Examples of the divalent chain saturated hydrocarbon group which may have a fluorine atom include alkanediyl groups such as a methylene group, an ethylene group, a propanediyl group, a butanediyl group, and a pentanediyl group; and perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropanediyl group, a perfluorobutanediyl group, and a perfluoropentanediyl group. The divalent alicyclic saturated hydrocarbon group optionally having a fluorine atom may be either monocyclic or polycyclic. Examples of the monocyclic group include a cyclohexanediyl group and a perfluorocyclohexanediyl group. Examples of the polycyclic group include an adamantanediyl group, a norbornanediyl group, and a perfluoroadamantanediyl group.

[0180] A f14The saturated hydrocarbon group and the saturated hydrocarbon group which may have a fluorine atom are R a42 Among these, a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, Preferred are fluorinated alkyl groups such as a hexyl group, a perfluorohexyl group, a heptyl group, a perfluoroheptyl group, an octyl group, and a perfluorooctyl group, a cyclopropylmethyl group, a cyclopropyl group, a cyclobutylmethyl group, a cyclopentyl group, a cyclohexyl group, a perfluorocyclohexyl group, an adamantyl group, an adamantylmethyl group, an adamantyldimethyl group, a norbornyl group, a norbornylmethyl group, a perfluoroadamantyl group, and a perfluoroadamantylmethyl group.

[0181] In formula (a4-3), L 5 is preferably an ethylene group. A f13 The divalent saturated hydrocarbon group is preferably a group containing a divalent chain saturated hydrocarbon group having 1 to 6 carbon atoms and a divalent alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a divalent chain saturated hydrocarbon group having 2 to 3 carbon atoms. A f14 The saturated hydrocarbon group is preferably a group containing a chain saturated hydrocarbon group having 3 to 12 carbon atoms and a group containing an alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a group containing a chain saturated hydrocarbon group having 3 to 10 carbon atoms and a group containing an alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms. f14 is preferably a group containing an alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a cyclopropylmethyl group, a cyclopentyl group, a cyclohexyl group, a norbornyl group, or an adamantyl group.

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

[0183] The structural unit (a4) also includes a structural unit represented by formula (a4-4). TIFF2023143845000121.tif4466[In formula (a4-4), R f21 represents a hydrogen atom or a methyl group. A f21 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -or-(CH2) j4 -CO-O-(CH2) j5 - represents. j1 to j5 each independently represent an integer of 1 to 6. R f22 represents a saturated hydrocarbon group having 1 to 10 carbon atoms and containing a fluorine atom.]

[0184] R f22 The saturated hydrocarbon group of R a42 R f22 is preferably an alkyl group having 1 to 10 carbon atoms and containing a fluorine atom or an alicyclic saturated hydrocarbon group having 1 to 10 carbon atoms and containing a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms and containing a fluorine atom, and even more preferably an alkyl group having 1 to 6 carbon atoms and containing a fluorine atom.

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

[0186] Examples of the structural unit represented by formula (a4-4) include the following structural units and structural units represented by the following formulas: f21 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2023143845000122.tif90164

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

[0188] <Structural unit (a5)> The non-leaving hydrocarbon group contained in the structural unit (a5) may be a group containing a linear, branched, or cyclic hydrocarbon group, and among these, the structural unit (a5) is preferably a group containing an alicyclic hydrocarbon group. Examples of the structural unit (a5) include a structural unit represented by formula (a5-1). TIFF2023143845000123.tif3351[In formula (a5-1), R 51 represents a hydrogen atom or a methyl group. R 52 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group may be substituted with an aliphatic hydrocarbon group having 1 to 8 carbon atoms. L 55 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.]

[0189] R 52 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of polycyclic alicyclic hydrocarbon groups include adamantyl and norbornyl. Examples of the aliphatic hydrocarbon group having 1 to 8 carbon atoms include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl. Examples of the alicyclic hydrocarbon group having a substituent include a 3-methyladamantyl group. R 52 is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, and more preferably an adamantyl group, a norbornyl group, or a cyclohexyl group.

[0190] L 55 The divalent saturated hydrocarbon group in the formula (I) includes a divalent saturated chain hydrocarbon group and a divalent saturated alicyclic hydrocarbon group, and is preferably a divalent saturated chain hydrocarbon group. Examples of the divalent chain saturated hydrocarbon group include a methylene group, an ethylene group, and an alkanediyl group such as a propanediyl group, a butanediyl group, and a pentanediyl group. The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic saturated hydrocarbon group include cycloalkanediyl groups such as cyclopentanediyl and cyclohexanediyl. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include adamantanediyl and norbornanediyl.

[0191] L 55 Examples of the divalent saturated hydrocarbon group represented by formula (L1-1) in which one -CH2- is replaced with -O- or -CO- include groups represented by formula (L1-1) to formula (L1-4). In the following formulae, * and ** each represent a bonding site, and * represents a bonding site to an oxygen atom. TIFF2023143845000124.tif18164[In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents L x1 represents the binding site with ). L x1 represents a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. L x2 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. However, L x1 and L x2 The total number of carbon atoms is 16 or less. In formula (L1-2), L x3 represents a divalent aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms. L x4 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. However, L x3 and L x4 The total number of carbon atoms is 17 or less. In formula (L1-3), L x5 represents a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. L x6 and L x7 each independently represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 14 carbon atoms. However, L x5 , L x6 and L x7 The total number of carbon atoms is 15 or less. In formula (L1-4), L x8 and L x9 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms. W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, L x8 , L x9 and W x1 The total number of carbon atoms is 15 or less.

[0192] 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 x3is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x6 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x7 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x8 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. L x9 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. W x1 is preferably a divalent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, more preferably a cyclohexanediyl group or an adamantanediyl group.

[0193] Examples of the group represented by formula (L1-1) include the divalent groups shown below. TIFF2023143845000125.tif37147 Examples of the group represented by formula (L1-2) include the divalent groups shown below. TIFF2023143845000126.tif23130 Examples of the group represented by formula (L1-3) include the divalent groups shown below. TIFF2023143845000127.tif16147Examples of the group represented by formula (L1-4) include the divalent groups shown below. TIFF2023143845000128.tif13168L 55 is preferably a single bond or a group represented by formula (L1-1).

[0194] The structural unit (a5-1) includes the structural units shown below and R in the structural unit (a5-1) in the structural units shown below. 51 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. When the resin (A) or the like contains the structural unit (a5), the content thereof is preferably 1 to 30 mol %, more preferably 2 to 20 mol %, and even more preferably 3 to 15 mol %, based on all structural units in the resin (A) or the like.

[0195] <Structural unit (a6)> The structural unit (a6) is a structural unit having an -SO2- group, and preferably has an -SO2- group in a side chain. The structural unit having an -SO2- group may have a linear structure having an -SO2- group, a branched structure having an -SO2- group, or a cyclic structure (monocyclic or polycyclic structure) having an -SO2- group. A structural unit having a cyclic structure having an -SO2- group is preferred, and a structural unit having a cyclic structure containing an -SO2-O- group (sultone ring) is more preferred.

[0196] The sultone ring may be a ring having the following formula (T 1 -1), formula (T 1 -2), formula (T 1 -3) and the formula (T 1 The bonding site can be any position. The sultone ring may be monocyclic, but is preferably polycyclic. A polycyclic sultone ring refers to a bridged ring containing -SO2-O- as an atomic group constituting the ring, and is represented by the formula (T 1 -1) and the formula (T 1 The sultone ring is represented by the formula (T 1 As in the ring represented by formula (2), the atomic group constituting the ring may further contain a heteroatom in addition to —SO—O—. Examples of the heteroatom include an oxygen atom, a sulfur atom, and a nitrogen atom, and an oxygen atom is preferred. TIFF2023143845000130.tif3087

[0197] The sultone ring may have a substituent, and examples of the substituent include an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, and an alkylcarbonyl group having 2 to 4 carbon atoms.

[0198] Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, and a decyl group, and preferably an alkyl group having 1 to 6 carbon atoms, and more preferably a methyl group. Examples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group, and preferably a trifluoromethyl group. Examples of the alkyl group having a hydroxy group include a hydroxymethyl group and a 2-hydroxyethyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a p-methylphenyl group, a p-tert-butylphenyl group, a p-adamantylphenyl group, a tolyl group, a xylyl group, a cumyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group. Aralkyl groups include benzyl, phenethyl, phenylpropyl, naphthylmethyl, and naphthylethyl groups. Examples of the alkoxycarbonyl group include groups in which an alkoxy group, such as a methoxycarbonyl group or an ethoxycarbonyl group, is bonded to a carbonyl group, and preferred are alkoxycarbonyl groups having 6 or less carbon atoms, more preferably a methoxycarbonyl group. Alkylcarbonyl groups include acetyl, propionyl and butyryl groups.

[0199] From the viewpoint of ease of production of the monomer from which the structural unit (a6) is derived, a sultone ring having no substituent is preferred. The sultone ring is preferably a ring represented by the following formula (T1'). TIFF2023143845000131.tif3072[In formula (T1'), X 11 represents an oxygen atom, a sulfur atom or a methylene group. R 41 represents an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, or an alkylcarbonyl group having 2 to 4 carbon atoms. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41 may be the same or different. The binding site is at any position.] X 11 is preferably an oxygen atom or a methylene group, more preferably a methylene group. R 41 Examples of the substituent include the same as the substituent on the sultone ring, and an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group is preferred. ma is preferably 0 or 1, and more preferably 0.

[0200] Examples of the ring represented by formula (T1') include the following rings: The binding site may be any position, and the binding site is preferably the 1st or 3rd position. TIFF2023143845000132.tif47147

[0201] The structural unit having an -SO2- group preferably further has a group derived from a polymerizable group, such as a vinyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, an acryloylthio group, or a methacryloylthio group. Among these, the monomer from which the structural unit (a6) is derived is preferably a monomer having an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer.

[0202] The structural unit (a6) is preferably a structural unit represented by the formula (a6-0). TIFF2023143845000133.tif4963[In formula (a6-0), R x represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom. A xx is an oxygen atom, -N(R c )- or a sulfur atom. A x represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group is not -O-, -CO- or -N(R d )- may be replaced. X 11 , R 41 and ma have the same meanings as above. R c and R d each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0203] R x Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R x Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group, and are preferably alkyl groups having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. R x Examples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group. R x is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group.

[0204] A x Examples of the divalent saturated hydrocarbon group include a linear alkanediyl group, a branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and may be a combination of two or more of these groups. Specifically, methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group linear alkanediyl groups such as a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, a heptadecane-1,17-diyl group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group; branched alkanediyl groups such as butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl; monocyclic divalent alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; Examples include polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group. A x The bonding position of to the sultone ring can be any position, but the 1-position is preferred.

[0205] Examples of the structural unit (a6-0) include the following structural units. TIFF2023143845000134.tif93150

[0206] Of these, structural units represented by formula (a6-1), formula (a6-2), formula (a6-6), formula (a6-7), formula (a6-8), and formula (a6-12) are preferred, and structural units represented by formula (a6-1), formula (a6-2), formula (a6-7), and formula (a6-8) are more preferred. When the resin (A) or the like contains the structural unit (a6), the content thereof is preferably 1 to 50 mol %, more preferably 2 to 40 mol %, and even more preferably 3 to 30 mol %, based on all structural units in the resin (A) or the like.

[0207] The resin (A) and the like are preferably resins containing the structural unit (a1). In particular, the resin (Ap) is more preferably a resin consisting of the structural unit (IP), the structural unit (a1), and the structural unit (s), i.e., a copolymer of the salt (I), the monomer (a1), and the monomer (s). The resin (A) not containing the structural unit (IP) is preferably a resin consisting of the structural unit (a1) and the structural unit (s), i.e., a copolymer of the monomer (a1) and the monomer (s).

[0208] The structural unit (a1) is preferably at least one selected from the group consisting of the structural unit (a1-0), the structural unit (a1-1), and the structural unit (a1-2) (preferably the structural unit having a cyclohexyl group or a cyclopentyl group), more preferably at least two selected from the group consisting of the structural unit (a1-1) and the structural unit (a1-2). The structural unit (s) is preferably at least one selected from the group consisting of the structural unit (a2) and the structural unit (a3). The structural unit (a2) is preferably the structural unit (a2-1) or the structural unit (a2-A). The structural unit (a3) ​​is preferably at least one selected from the group consisting of the structural unit represented by formula (a3-1), the structural unit represented by formula (a3-2), and the structural unit represented by formula (a3-4).

[0209] Each structural unit constituting the resin (A) etc. may be used alone or in combination of two or more, and can be produced by a known polymerization method (e.g., radical polymerization method) using a monomer that leads to these structural units. The content of each structural unit contained in the resin (A) etc. can be adjusted by the amount of monomer used in polymerization. The weight-average molecular weight of resin (A) and resin (Ap) is preferably 2,000 or more (more preferably 2,500 or more, even more preferably 3,000 or more) and 50,000 or less (more preferably 30,000 or less, even more preferably 15,000 or less). In this specification, the weight-average molecular weight is a value determined by gel permeation chromatography under the conditions described in the Examples. The structural unit (IP) may constitute a dimer, trimer, or compound having a weight-average molecular weight of less than 2,000.

[0210] [Acid Generator] The acid generator of the present invention is an acid generator containing a salt (I) or a structural unit (IP). The structural unit (IP) can be contained as a compound or resin in which a plurality of units are polymerized. In the acid generator, the salt (I) may be used alone or in combination of two or more. The compound or resin containing the structural unit (IP) may be used alone or in combination of two or more. The acid generator of the present invention may also contain both the salt (I) and the structural unit (IP). The acid generator of the present invention may contain, in addition to the salt (I), an acid generator known in the resist field (hereinafter, sometimes referred to as "acid generator (B)" or "second acid generator"). The acid generator (B) will be described later. When the acid generator contains a salt (I) and an acid generator (B), the ratio of the salt (I) to the acid generator (B) (mass ratio, salt (I):acid generator (B)) is usually 1:99 to 99:1, preferably 2:98 to 98:2, more preferably 5:95 to 95:5, even more preferably 10:90 to 90:10, still more preferably 15:85 to 85:15, and particularly preferably 40:60 to 60:40.

[0211] [Resist Composition] The resist composition of the present invention contains an acid generator of the present invention. The acid generator may be a resin (Ap) containing the structural unit (IP). The resist composition of the present invention may contain an acid generator (B) that does not contain an acid generator of the present invention, or may contain a resin that does not contain the structural unit (IP). The resin that does not contain the structural unit (IP) may be a resin that contains a structural unit (a1) having an acid labile group, or a resin that does not contain the structural unit (a1). The resist composition of the present invention, however, contains at least one of the salt (I) and the structural unit (IP), and may contain both. That is, the resist composition of the present invention only needs to contain an acid generator that contains the structural unit (IP) of the present invention or the salt (I) of the present invention. The structural unit (IP) may be in the form of a compound, a resin, or the like. In other words, the resist composition of the present invention may contain a resin (Ap) and / or a resin (A) and a salt (I) as an acid generator. The resist composition of the present invention preferably contains a resin that contains the structural unit (a1) having an acid labile group. That is, at least (a) a salt (I) and a resin (A) containing a structural unit (a1) having an acid labile group, (b) a resin (Ap) containing the structural unit (IP) and the structural unit (a1) having an acid labile group; (c) It is preferable to contain a resin (Ap) containing the structural unit (IP) and a resin (A) containing a structural unit (a1) having an acid labile group. Among these, a resist composition containing a resin (Ap) containing the structural unit (IP) and the structural unit (a1) having an acid labile group is preferred. Two or more types of resins (A) and / or resins (Ap) may be contained. The resist composition of the present invention preferably further contains a quencher (hereinafter sometimes referred to as "quencher (C)") and / or a solvent (hereinafter sometimes referred to as "solvent (E)"). The resist composition of the present invention may further contain a resin other than the above-mentioned resin (A) and the like.

[0212] <Resins other than Resin (A), etc.> The resist composition of the present invention may contain a resin other than the resin (Ap) and the resin (A). Examples of the resin other than the resin (Ap) and the resin (A) include a resin (AX) having the same structural units as the resin (A) except that it does not contain the structural unit (a1), and a resin containing the structural unit (a4) and / or the structural unit (a5) (however, it does not contain the structural unit (IP) and the structural unit (a1); hereinafter, this may be referred to as "resin (X)").

[0213] Examples of the resin (AX) include resins containing the structural unit (a2), and resins containing the structural unit (a2-A) are preferred. In the resin (AX), the content of the structural unit (a2-A) is preferably 5 mol% or more, more preferably 10 mol% or more, and even more preferably 15 mol% or more, based on the total of all structural units in the resin (AX), and is preferably 80 mol% or less, more preferably 70 mol% or less. Examples of structural units that the resin (X) may further have include the structural unit (a2), the structural unit (a3), and structural units derived from other known monomers. Among these, the resin (X) is preferably a resin consisting only of the structural unit (a4) and / or the structural unit (a5), and more preferably a resin consisting only of the structural unit (a4). When resin (X) contains structural unit (a4), the content of structural unit (a4) in resin (X) is, based on the total of all structural units in resin (X), 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more. Also, it may be 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, even more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, it may be 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, even more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. When resin (X) contains structural unit (a5), the content of structural unit (a5) in resin (X) is, based on the total of all structural units in resin (X), 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more. Further, it may be 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, even more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specific examples include 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, even more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. Furthermore, when the resin (X) contains the structural unit (a4) and the structural unit (a5), the total content of the structural unit (a4) and the structural unit (a5) relative to the total of all structural units in the resin (X) may be 40 mol% or more, preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more. Further, it may be 100 mol% or less. Specific examples include 40 to 100 mol%, preferably 60 to 100 mol%, more preferably 70 to 100 mol%, and even more preferably 80 to 100 mol%. The structural units constituting resins (AX) and (X) may be used singly or in combination of two or more, and can be produced by known polymerization methods (e.g., radical polymerization) using monomers that derive these structural units. The content of each structural unit in resins (AX) and (X) can be adjusted by the amount of monomer used in polymerization. The weight-average molecular weight of resin (AX) and 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), but they may contain oligomers or the like having a weight-average molecular weight of less than 6,000. The means for measuring the weight-average molecular weight of resin (AX) and resin (X) is the same as for resin (A) and the like.

[0214] When the resist composition of the present invention contains resin (X), the content thereof is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, even more preferably 1 to 40 parts by mass, still more preferably 1 to 30 parts by mass, and even more preferably 1 to 8 parts by mass, relative to 100 parts by mass in total of resin (A) and the like.

[0215] The content of resin (A) etc. in the resist composition is preferably 80% to 99% by mass, and more preferably 90% to 99% by mass, based on the solid content of the resist composition. The content of resin (Ap) is preferably 80% to 99% by mass, and more preferably 90% to 99% by mass, based on the solid content of the resist composition. Furthermore, when a resin other than resin (A) etc. is contained, the total content of resin (A etc.) and the resin other than resin (A) etc. is preferably 80% to 99% by mass, and more preferably 90% to 99% by mass, based on the solid content of the resist composition. In this specification, the "solid content of the resist composition" refers to the sum of all components excluding the solvent (E), which will be described later, from the total amount of the resist composition. The solid content of the resist composition and the resin content relative to the solid content can be measured using known analytical methods such as liquid chromatography or gas chromatography.

[0216] <Acid generator> The acid generator of the present invention may be either an acid generator containing only the salt (I) and / or the structural unit (IP), or an acid generator containing the salt (I) and / or the structural unit (IP) and an acid generator (B) known in the resist field. The acid generators used in the resist composition of the present invention may be used either alone or in combination of two or more.

[0217] The acid generator (B) may be either nonionic or ionic. Nonionic acid generators include sulfonate esters (e.g., 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxyketone, diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfone, ketosulfone, sulfonyldiazomethane), etc. Ionic acid generators include onium salts containing onium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts, iodonium salts). Anions of onium salts include sulfonate anions, sulfonylimide anions, sulfonylmethide anions, etc.

[0218] The acid generator (B) may be a compound that generates an acid when exposed to radiation, as described in JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, JP-A-63-146029, U.S. Pat. No. 3,779,778, U.S. Pat. No. 3,849,137, German Patent No. 3,914,407, or European Patent No. 126,712. Compounds produced by known methods may also be used. Two or more types of acid generator (B) may be used in combination.

[0219] The acid generator (B) is preferably a salt represented by formula (B1) (hereinafter, sometimes referred to as "acid generator (B1)"). TIFF2023143845000135.tif2958[In formula (B1), Q b1 and Q b2 each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L b1represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, wherein -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and wherein a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y represents an optionally substituted methyl group or an optionally substituted alicyclic hydrocarbon group having 3 to 24 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-. Z + represents an organic cation.

[0220] Q in formula (B1) b1 , Q b2 and L b1 As for Q in formula (I), b1 , Q b2 and L b1 The same examples as those mentioned above can be mentioned.

[0221] Examples of the alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent in Y (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-) include Y in formula (I): b1 The same examples as those mentioned above can be mentioned. When the alicyclic hydrocarbon group represented by Y is a spiro ring having an oxygen atom such as those of 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. Furthermore, among the alkanediyl groups contained in the ketal structure, it is preferred that the methylene group adjacent to the oxygen atom is not substituted with a fluorine atom.

[0222] The substituent of the methyl group represented by Y is a halogen atom, a hydroxy group, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, a glycidyloxy group, -(CH2) ja -CO-OR b1 group or -(CH2) ja -O-CO-Rb1 group (in the formula, R b1 represents an alkyl group having 1 to 16 carbon atoms, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a combination thereof. ja represents an integer of 0 to 4. -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced by -O-, -SO2-, or -CO-, and a hydrogen atom contained in the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may be replaced by a hydroxy group or a fluorine atom. Y is preferably an alicyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, more preferably an alicyclic hydrocarbon group of 3 to 20 carbon atoms which may have a substituent, even more preferably an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent, and even more preferably an adamantyl group which may have a substituent or a norbornyl group which may have a substituent, wherein -CH2- constituting the alicyclic hydrocarbon group, adamantyl group or norbornyl group may be replaced by -O-, -S-, -SO2- or -CO-. Specific examples include the following. JPEG2023143845000136.jpg117158

[0223] TIFF2023143845000137.tif54155

[0224] Among these, Y is preferably an adamantyl group, a hydroxyadamantyl group, an oxoadamantyl group, a norbornane lactone group, or a group represented by any of the formulae (Y42), (Y100) to (Y114), and (Y134) to (Y139), and particularly preferably a hydroxyadamantyl group, an oxoadamantyl group, a group containing these, or a group represented by any of the formulae (Y42), (Y100) to (Y114), and (Y134) to (Y139).

[0225] The anion in the salt represented by formula (B1) is preferably an anion represented by formula (B1-A-1) to formula (B1-A-65) (hereinafter, sometimes referred to as "anion (B1-A-1)" depending on the formula number).), and more preferably an anion 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), and formula (B1-A-47) to formula (B1-A-65).

[0226] TIFF2023143845000138.tif205163

[0227] JPEG2023143845000139.jpg247165

[0228] TIFF2023143845000140.tif213163 Here R i2 ~R i7 are each independently, for example, an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group. i8 is, for example, a chain hydrocarbon group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a group formed by combining these, more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. A41 Q is a single bond or an alkanediyl group having 1 to 4 carbon atoms. b1 and Q b2 has the same meaning as above. Specific examples of the anion in the salt represented by formula (B1) include the anions described in JP-A-2010-204646.

[0229] Preferable anions in the salt represented by formula (B1) include anions represented by formulas (B1a-1) to (B1a-43). TIFF2023143845000141.tif236167

[0230] TIFF2023143845000142.tif114154

[0231] Among these, anions represented by any one of formulas (B1a-1) to (B1a-4), (B1a-7) to (B1a-11), (B1a-14) to (B1a-30), and (B1a-35) to (B1a-43) are preferred. Examples of the sulfonylimide anion include the following: TIFF2023143845000143.tif23137 Examples of sulfonylmethide anions include the following: TIFF2023143845000144.tif26131

[0232] Z + Examples of the organic cation include organic onium cations, organic sulfonium cations, organic iodonium cations, organic ammonium cations, benzothiazolium cations, and organic phosphonium cations. Among these, organic sulfonium cations and organic iodonium cations are preferred, and arylsulfonium cations are more preferred. Specific examples include cations represented by any of formulas (b2-1) to (b2-4) (hereinafter, sometimes referred to as "cation (b2-1)" depending on the formula number).

[0233] TIFF2023143845000145.tif48169In equations (b2-1) to (b2-4), R b4 ~R b6each independently represent a chain hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms, a hydrogen atom contained in the chain hydrocarbon group may be substituted with a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, a hydrogen atom contained in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a glycidyloxy group, and a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b4 and R b5 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b7 and R b8 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. m2 and n2 each independently represent an integer of 0 to 5; When m2 is 2 or more, multiple R b7 may be the same or different, and when n2 is 2 or more, multiple R b8 may be the same or different. R b9 and R b10 each independently represents a chain hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b11represents a hydrogen atom, a chain hydrocarbon group having 1 to 36 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. R b12 represents a chain hydrocarbon group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 12 carbon atoms or an alkylcarbonyloxy group having 1 to 12 carbon atoms. R b11 and R b12 may be bonded to each other to form a ring including the -CH-CO- to which they are bonded, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. R b13 ~R b18 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b13 and R b14 and may be bonded to each other to form a ring containing a sulfur atom together with the benzene ring to which they are attached, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. L b31 represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent an integer of 0 to 5. q2 and r2 each independently represent an integer of 0 to 4; u2 represents 0 or 1. When o2 is 2 or more, multiple R b13 are the same or different, and when p2 is 2 or more, multiple R b14 are the same or different, and when q2 is 2 or more, multiple R b15 are the same or different, and when r2 is 2 or more, multiple R b16 are the same or different, and when s2 is 2 or more, multiple R b17 are the same or different, and when t2 is 2 or more, multiple Rb18 are the same or different. When u2 is 0, any one of o2, p2, q2, and r2 is 1 or more, and R b13 ~R b16 At least one of o2, p2, s2, t2, q2, and r2 is preferably a halogen atom, and when u2 is 1, any one of o2, p2, s2, t2, q2, and r2 is 1 or more, and R b13 ~R b18 At least one of these is preferably a halogen atom. Furthermore, when u2 is 0, r2 is preferably 1 or more, and more preferably 1. When u2 is 0 and r2 is 1 or more, R b16 is preferably a halogen atom. The aliphatic hydrocarbon group refers to a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of the chain hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl. In particular, R b9 ~R b12 The chain hydrocarbon group preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups: TIFF2023143845000146.tif10158 In particular, R b9 ~R b12 The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, and more preferably has 4 to 12 carbon atoms. Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include a methylcyclohexyl group, a dimethylcyclohexyl group, a 2-methyladamantan-2-yl group, a 2-ethyladamantan-2-yl group, a 2-isopropyladamantan-2-yl group, a methylnorbornyl group, an isobornyl group, etc. In the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group, the total number of carbon atoms in the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 20 or less. The fluorinated alkyl group refers to an alkyl group having 1 to 12 carbon atoms and a fluorine atom, and examples thereof include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluorobutyl group, etc. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 9, more preferably 1 to 6, and even more preferably 1 to 4. Examples of aromatic hydrocarbon groups include aryl groups such as phenyl, biphenyl, naphthyl, and phenanthryl. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples thereof include aromatic hydrocarbon groups having a chain hydrocarbon group of 1 to 18 carbon atoms (such as tolyl, xylyl, cumenyl, mesityl, p-ethylphenyl, p-tert-butylphenyl, 2,6-diethylphenyl, and 2-methyl-6-ethylphenyl) and aromatic hydrocarbon groups having an alicyclic hydrocarbon group of 3 to 18 carbon atoms (such as p-cyclohexylphenyl and p-adamantylphenyl). When the aromatic hydrocarbon group has a chain hydrocarbon group or an alicyclic hydrocarbon group, chain hydrocarbon groups having 1 to 18 carbon atoms and alicyclic hydrocarbon groups having 3 to 18 carbon atoms are preferred. Examples of aromatic hydrocarbon groups in which hydrogen atoms are substituted with alkoxy groups include p-methoxyphenyl groups. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as benzyl, phenethyl, phenylpropyl, trityl, naphthylmethyl, and naphthylethyl. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkylcarbonyloxy group include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, an isopropylcarbonyloxy group, a butylcarbonyloxy group, a sec-butylcarbonyloxy group, a tert-butylcarbonyloxy group, a pentylcarbonyloxy group, a hexylcarbonyloxy group, an octylcarbonyloxy group, and a 2-ethylhexylcarbonyloxy group. R b4 and R b5 and bond to each other together with the sulfur atom to which they are bonded to form a ring which may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. This ring may be a ring having 3 to 18 carbon atoms, preferably a ring having 4 to 18 carbon atoms. The ring containing a sulfur atom may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring, for example, the following rings. * represents a bonding site. TIFF2023143845000147.tif23144R b9 and R b10 The ring formed by these together may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. This ring may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring. Examples thereof include a thiolan-1-ium ring (tetrahydrothiophenium ring), a thian-1-ium ring, and a 1,4-oxathian-4-ium ring. R b11 and R b12 The ring formed by combining these may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of this ring include a 3- to 12-membered ring, and preferably a 3- to 7-membered ring. Examples include an oxocycloheptane ring, an oxocyclohexane ring, an oxonorbornane ring, and an oxoadamantane ring.

[0234] Among the cations (b2-1) to (b2-4), the cation (b2-1) is preferred. Examples of the cation (b2-1) include the following cations. TIFF2023143845000148.tif129162Examples of the cation (b2-2) include the following cations. TIFF2023143845000149.tif18150Examples of the cation (b2-3) include the following cations. TIFF2023143845000150.tif26140Examples of the cation (b2-4) include the following cations. TIFF2023143845000151.tif120170

[0235] The acid generator (B) is a combination of the above-mentioned anions and the above-mentioned organic cations, which can be combined arbitrarily. Preferred examples of the acid generator (B) include a combination of an anion represented by any of formulas (B1a-1) to (B1a-4), (B1a-7) to (B1a-11), (B1a-14) to (B1a-30), and (B1a-35) to (B1a-43) with a cation (b2-1), (b2-2), (b2-3), or (b2-4).

[0236] Preferred examples of the acid generator (B) include those represented by formulas (B1-1) to (B1-60). Among these, those containing an arylsulfonium cation are preferred, and those represented by formulas (B1-1) to (B1-3), (B1-5) to (B1-7), (B1-11) to (B1-14), (B1-20) to (B1-26), (B1-29), and (B1-31) to (B1-60) are particularly preferred. JPEG2023143845000152.jpg214167

[0237] TIFF2023143845000153.tif235159

[0238] TIFF2023143845000154.tif237165

[0239] In the resist composition of the present invention, the content of the acid generator is preferably from 0.1 to 99.9% by mass, more preferably from 1 to 45% by mass, even more preferably from 1 to 40% by mass, and even more preferably from 3 to 40% by mass, relative to the solid content of the resist composition. When a resin (A) or the like is contained, the content of the acid generator is preferably from 1 to 45 parts by mass, more preferably from 1 to 40 parts by mass, and even more preferably from 3 to 35 parts by mass, relative to 100 parts by mass of the resin (A) or the like.

[0240] <Solvent (E)> The content of the solvent (E) in the resist composition is usually from 90 to 99.9% by mass, preferably from 92 to 99% by mass, and more preferably from 94 to 99% by mass. The content of the solvent (E) can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0241] Examples of the solvent (E) include glycol ether esters such as ethyl cellosolve acetate, methyl cellosolve acetate, and propylene glycol monomethyl ether acetate; glycol ethers such as propylene glycol monomethyl ether; esters such as ethyl lactate, butyl acetate, amyl acetate, and ethyl pyruvate; ketones such as acetone, methyl isobutyl ketone, 2-heptanone, and cyclohexanone; cyclic esters such as γ-butyrolactone; etc. One type of solvent (E) may be used alone, or two or more types may be used.

[0242] <Quencher (C)> Examples of the quencher (C) include salts that generate an acid with a lower acidity than the acid generated from the acid generator (salt (I), structural unit (IP), and acid generator (B1)), and basic nitrogen-containing organic compounds. The content of the quencher (C) is preferably about 0.01 to 15% by mass, more preferably about 0.01 to 10% by mass, still more preferably about 0.1 to 8% by mass, and even more preferably about 0.1 to 7% by mass, based on the solid content of the resist composition.

[0243] The acidity of the salt that generates an acid with a lower acidity than the acid generated from the acid generator is represented by the acid dissociation constant (pKa). The salt that generates an acid with a lower acidity than the acid generated from the acid generator is a salt having an acid dissociation constant of the acid generated from the salt usually of -3 < pKa, preferably -1 < pKa < 7, and more preferably 0 < pKa < 5. Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator include salts represented by the following formula, salts represented by formula (D) described in JP-A-2015-147926 (hereinafter sometimes referred to as "weak acid inner salt (D)"), and salts described in JP-A-2012-229206, JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-39502, and JP-A-2011-191745. As the salt that generates an acid with a lower acidity than the acid generated from the acid generator, preferably, it is a salt that generates a carboxylic acid with a lower acidity than the acid generated from the acid generator (a salt having a carboxylic acid anion), more preferably a weak acid inner salt (D), and still more preferably, among the weak acid inner salts (D), a diphenyliodonium salt containing a phenyl group substituted with a carboxylic acid anion. TIFF2023143845000155.tif96153

[0244] The weak acid inner salt (D) is preferably a diphenyliodonium salt having an iodonium cation to which two phenyl groups are bonded and a carboxylate anion substituted on at least one of the two phenyl groups bonded to the iodonium cation, and examples thereof include salts represented by the following formula: TIFF2023143845000156.tif1695[In formula (D), R D1 and R D2 each independently represents a hydrocarbon group having 1 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 7 carbon atoms, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a nitro group, or a halogen atom. m' and n' each independently represent an integer of 0 to 4, and when m' is 2 or more, a plurality of R D1 may be the same or different, and when n' is 2 or more, a plurality of R D2 may be the same or different.] R D1 and R D2 Examples of the hydrocarbon group include a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. Examples of the chain hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, and nonyl groups. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and may be either saturated or unsaturated. Examples of the alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclononyl, and cyclododecyl, norbornyl, and adamantyl. Examples of aromatic hydrocarbon groups include aryl groups such as a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a 4-propylphenyl group, a 4-isopropylphenyl group, a 4-butylphenyl group, a 4-t-butylphenyl group, a 4-hexylphenyl group, a 4-cyclohexylphenyl group, an anthryl group, a p-adamantylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group. Examples of groups formed by combining these groups include alkyl-cycloalkyl groups, cycloalkyl-alkyl groups, and aralkyl groups (e.g., phenylmethyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl-1-propyl group, 1-phenyl-2-propyl group, 2-phenyl-2-propyl group, 3-phenyl-1-propyl group, 4-phenyl-1-butyl group, 5-phenyl-1-pentyl group, and 6-phenyl-1-hexyl group). Examples of the alkoxy group include a methoxy group and an ethoxy group. Examples of the acyl group include an acetyl group, a propanoyl group, a benzoyl group, and a cyclohexanecarbonyl group. Examples of the acyloxy group include groups in which an oxy group (—O—) is bonded to the above-mentioned acyl group. Examples of the alkoxycarbonyl group include a group in which a carbonyl group (—CO—) is bonded to the above alkoxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. R D1 and R D2 are each independently preferably an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 4 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 4 carbon atoms, a nitro group, or a halogen atom. m' and n' are each preferably an integer of 0 to 2, more preferably 0. When m' is 2 or more, multiple RD1 may be the same or different, and when n' is 2 or more, a plurality of R D2 may be the same or different. More specifically, the following salts are included: TIFF2023143845000157.tif72165

[0245] The basic nitrogen-containing organic compound includes amines and ammonium salts. The amines include aliphatic amines and aromatic amines. The aliphatic amines include primary amines, secondary amines, and tertiary amines. Amines include 1-naphthylamine, 2-naphthylamine, aniline, diisopropylaniline, 2-, 3- or 4-methylaniline, 4-nitroaniline, N-methylaniline, N,N-dimethylaniline, diphenylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, triethylamine, trimethylamine, tripropylamine, tributylamine, Amine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, methyldibutylamine, methyldipentylamine, methyldihexylamine, methyldicyclohexylamine, methyldiheptylamine, methyldioctylamine, methyldinonylamine, methyldidecylamine, ethyldibutylamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine, ethyldioctylamine, ethyldinonylamine, ethyldidecylamine amine, dicyclohexylmethylamine, tris[2-(2-methoxyethoxy)ethyl]amine, triisopropanolamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4'-diamino-1,2-diphenylethane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 4,4'-diamino-3,3'-diethyldiphenylmethane, 2,2'-methylenebisaniline, imidazole, 4-methylimidazole, pyridine, 4-methylpyridine, 1,2-di(2-pyridyl)ethane Examples of the amines include 1,2-di(4-pyridyl)ethane, 1,2-di(2-pyridyl)ethene, 1,2-di(4-pyridyl)ethene, 1,3-di(4-pyridyl)propane, 1,2-di(4-pyridyloxy)ethane, di(2-pyridyl)ketone, 4,4'-dipyridyl sulfide, 4,4'-dipyridyl disulfide, 2,2'-dipyridylamine, 2,2'-dipicolylamine, and bipyridine. Preferred are aromatic amines such as diisopropylaniline, and more preferred is 2,6-diisopropylaniline. Examples of ammonium salts include tetramethylammonium hydroxide, tetraisopropylammonium hydroxide, tetrabutylammonium hydroxide, tetrahexylammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethylammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium hydroxide, tetra-n-butylammonium salicylate, and choline.

[0246] <Other ingredients> The resist composition of the present invention may optionally contain components other than those described above (hereinafter, these may be referred to as "other components (F)"). There are no particular limitations on the other components (F), and additives known in the resist field, such as sensitizers, dissolution inhibitors, surfactants, stabilizers, and dyes, can be used.

[0247] <Preparation of Resist Composition> The resist composition of the present invention can be prepared by mixing a salt represented by formula (I) or a compound or resin containing a structural unit represented by formula (IP), and optionally a resin (A) or the like, an acid generator (B), a resin other than the resin (A) or the like, a solvent (E), a quencher (C), and other components (F). The order of mixing is arbitrary and is not particularly limited. The temperature during mixing can be selected from 10 to 40°C as appropriate depending on the type of resin, the solubility of the resin in the solvent (E), and the like. The mixing time can be selected from 0.5 to 24 hours as appropriate depending on the mixing temperature. The mixing method is also not particularly limited, and stirring and mixing can be used. After mixing the components, it is preferable to filter the mixture using a filter with a pore size of about 0.003 to 0.2 μm.

[0248] <Method for producing a resist pattern> The method for producing a resist pattern of the present invention comprises the steps of: (1) applying the resist composition of the present invention onto a substrate; (2) drying the applied composition to form a composition layer; (3) exposing the composition layer to light; (4) heating the composition layer after exposure; and (5) A step of developing the composition layer after heating is included. The resist composition can be applied to a substrate using a commonly used device such as a spin coater. Examples of the substrate include inorganic substrates such as silicon wafers and organic substrates having a resist film or the like formed on their surfaces. Before applying the resist composition, the substrate may be cleaned, and an anti-reflective film or the like may be formed on the substrate. The composition after coating is dried to remove the solvent and form a composition layer. Drying is carried out, for example, by evaporating the solvent using a heating device such as a hot plate (so-called pre-baking), or by using a vacuum device. The heating temperature is preferably 50 to 200°C, and the heating time is preferably 10 to 180 seconds. The pressure during vacuum drying is preferably 1 to 1.0 x 10 5 It is preferable that the pressure is about Pa. The resulting composition layer is typically exposed using an exposure machine. The exposure machine may be an immersion exposure machine. Various exposure light sources can be used, including those that emit ultraviolet laser light such as KrF excimer laser (wavelength 248 nm), ArF excimer laser (wavelength 193 nm), and F2 excimer laser (wavelength 157 nm); those that convert the wavelength of laser light from a solid-state laser source (such as a YAG or semiconductor laser) to emit harmonic laser light in the far ultraviolet or vacuum ultraviolet range; and those that irradiate with electron beams or extreme ultraviolet light (EUV). In this specification, irradiation with these types of radiation may be collectively referred to as "exposure." During exposure, exposure is typically performed through a mask corresponding to the desired pattern. When the exposure light source is an electron beam, exposure may be performed by direct writing without using a mask. The composition layer after exposure is subjected to a heat treatment (so-called post-exposure bake) to promote the deprotection reaction of the acid labile groups. The heating temperature is usually about 50 to 200°C, preferably about 70 to 150°C. A chemical treatment (silylation) may be performed to adjust the hydrophilicity or hydrophobicity of the resin on the surface side of the heated composition. Furthermore, before development, the steps of applying a resist composition, drying, exposing, and heating may be repeated on the composition layer after exposure. The heated composition layer is usually developed using a developer in a developing device. Development methods include dipping, puddling, spraying, and dynamic dispensing. The development temperature is preferably, for example, 5 to 60°C, and the development time is preferably, for example, 5 to 300 seconds. By selecting the type of developer as follows, a positive resist pattern or a negative resist pattern can be produced. When a positive resist pattern is produced from the resist composition of the present invention, an alkaline developer is used as the developer. The alkaline developer may be any of various alkaline aqueous solutions used in this field. Examples include aqueous solutions of tetramethylammonium hydroxide and (2-hydroxyethyl)trimethylammonium hydroxide (commonly known as choline). The alkaline developer may also contain a surfactant. After development, the resist pattern is preferably washed with ultrapure water, and then water remaining on the substrate and pattern is removed. When a negative resist pattern is produced from the resist composition of the present invention, a developer containing an organic solvent (hereinafter sometimes referred to as an "organic developer") is used as the developer. Examples of organic solvents contained in organic developers include ketone solvents such as 2-hexanone and 2-heptanone; glycol ether ester solvents such as propylene glycol monomethyl ether acetate; ester solvents such as butyl acetate; glycol ether solvents such as propylene glycol monomethyl ether; amide solvents such as N,N-dimethylacetamide; and aromatic hydrocarbon solvents such as anisole. The content of the organic solvent in the organic developer is preferably 90% by mass or more and 100% by mass or less, more preferably 95% by mass or more and 100% by mass or less, and even more preferably substantially only the organic solvent. Among these, the organic developer is preferably a developer containing butyl acetate and / or 2-heptanone. The total content of butyl acetate and 2-heptanone in the organic developer is preferably 50% by mass or more and 100% by mass or less, more preferably 90% by mass or more and 100% by mass or less, and even more preferably substantially only butyl acetate and / or 2-heptanone. The organic developer may contain a surfactant and a small amount of water. During development, development may be stopped by replacing the organic developer with a different type of solvent. The developed resist pattern is preferably washed with a rinse solution. There are no particular limitations on the rinse solution as long as it does not dissolve the resist pattern, and a solution containing a general organic solvent can be used, preferably an alcohol solvent or an ester solvent. After cleaning, it is preferable to remove the rinse liquid remaining on the substrate and the pattern.

[0249] <Application> The resist composition of the present invention is suitable as a resist composition for KrF excimer laser exposure, a resist composition for ArF excimer laser exposure, a resist composition for electron beam (EB) exposure, or a resist composition for EUV exposure, and is particularly suitable as a resist composition for electron beam (EB) exposure or a resist composition for EUV exposure, and is useful for semiconductor microfabrication. [Example]

[0250] The present invention will be explained in more detail with reference to examples. In the examples, "%" and "parts" representing the content or amount used are by mass unless otherwise specified. The weight-average molecular weight is a value determined by gel permeation chromatography under the following analytical conditions: Column: TSKgel Multipore HXL-M x 3 + guard column (Tosoh Corporation) Eluent: tetrahydrofuran Flow rate: 1.0mL / min Detector: RI detector Column temperature: 40℃ Injection volume: 100μl Molecular weight standard: Standard polystyrene (Tosoh Corporation) The structure of the compound was confirmed by measuring the molecular ion peak using mass spectrometry (LC: Agilent 1100, MASS: Agilent LC / MSD). In the following examples, the value of this molecular ion peak is indicated by "MASS".

[0251] Example 1: Synthesis of salt represented by formula (I-912) TIFF2023143845000158.tif68161 2.64 parts of the compound represented by formula (I-2-c) and 50 parts of chloroform were mixed and stirred at 23 ° C for 30 minutes, after which 1.62 parts of the compound represented by formula (I-2-b) were added, the temperature was raised to 50 ° C, and the mixture was stirred at 50 ° C for 2 hours. 8.54 parts of the salt represented by formula (I-912-a) were added to the resulting reaction mixture and stirred at 50 ° C for 10 hours. The resulting reaction mixture was cooled to 23 ° C, 25 parts of ion-exchanged water was added, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was isolated. 25 parts of ion-exchanged water was added to the resulting organic layer, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was isolated and the organic layer was isolated. This water washing procedure was repeated five times. The obtained organic layer was concentrated, and 3 parts of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue. After stirring at 23°C for 30 minutes, the supernatant was removed and the mixture was concentrated to obtain 9.01 parts of the salt represented by formula (I-912). MASS(ESI(+)Spectrum):M + 693.0 MASS(ESI(-)Spectrum):M - 407.1

[0252] Example 2: Synthesis of salt represented by formula (I-898) 2.64 parts of the compound represented by formula (I-2-c) and 50 parts of chloroform were mixed and stirred at 23°C for 30 minutes. Then, 1.62 parts of the compound represented by formula (I-2-b) were added, and the mixture was heated to 50°C and stirred at 50°C for 2 hours. 7.82 parts of the salt represented by formula (I-898-a) were added to the resulting reaction mixture and stirred at 50°C for 10 hours. The resulting reaction mixture was cooled to 23°C, and 25 parts of ion-exchanged water was added. The mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated and isolated. 25 parts of ion-exchanged water was added to the resulting organic layer, and the mixture was stirred at 23°C for 30 minutes. The organic layer was separated and isolated. This water washing procedure was repeated five times. The obtained organic layer was concentrated, and 3 parts of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue. After stirring at 23°C for 30 minutes, the supernatant was removed and the mixture was concentrated to obtain 7.96 parts of the salt represented by formula (I-898). MASS(ESI(+)Spectrum):M + 620.9 MASS(ESI(-)Spectrum):M - 407.1

[0253] Example 3: Synthesis of salt represented by formula (I-1990) TIFF2023143845000160.tif68161 2.64 parts of the compound represented by formula (I-2-c) and 50 parts of chloroform were mixed and stirred at 23 ° C for 30 minutes, after which 1.62 parts of the compound represented by formula (I-2-b) were added, the temperature was raised to 50 ° C, and the mixture was stirred at 50 ° C for 2 hours. 8.54 parts of the salt represented by formula (I-1990-a) were added to the resulting reaction mixture and stirred at 50 ° C for 10 hours. The resulting reaction mixture was cooled to 23 ° C, 25 parts of ion-exchanged water was added, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was extracted. 25 parts of ion-exchanged water was added to the resulting organic layer, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was extracted. This water washing procedure was repeated five times. The obtained organic layer was concentrated, and 3 parts of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue. After stirring at 23°C for 30 minutes, the supernatant was removed and the mixture was concentrated to obtain 9.16 parts of the salt represented by formula (I-1990). MASS(ESI(+)Spectrum):M + 693.0 MASS(ESI(-)Spectrum):M - 407.1

[0254] Example 4: Synthesis of salt represented by formula (I-2116) TIFF2023143845000161.tif58161 2.64 parts of the compound represented by formula (I-2-c) and 50 parts of chloroform were mixed and stirred at 23 ° C for 30 minutes, after which 1.62 parts of the compound represented by formula (I-2-b) were added, the temperature was raised to 50 ° C, and the mixture was stirred at 50 ° C for 2 hours. 8.54 parts of the salt represented by formula (I-2116-a) were added to the resulting reaction mixture and stirred at 50 ° C for 10 hours. The resulting reaction mixture was cooled to 23 ° C, 25 parts of ion-exchanged water was added, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was isolated. 25 parts of ion-exchanged water was added to the resulting organic layer, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was isolated. This water washing procedure was repeated five times. The obtained organic layer was concentrated, and 3 parts of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue. After stirring at 23°C for 30 minutes, the supernatant was removed and the mixture was concentrated to obtain 8.89 parts of the salt represented by formula (I-2116). MASS(ESI(+)Spectrum):M + 693.0 MASS(ESI(-)Spectrum):M - 407.1

[0255] Example 5: Synthesis of salt represented by formula (I-2102) TIFF2023143845000162.tif59161 2.64 parts of the compound represented by formula (I-2-c) and 50 parts of chloroform were mixed and stirred at 23 ° C for 30 minutes, after which 1.62 parts of the compound represented by formula (I-2-b) were added, the temperature was raised to 50 ° C, and the mixture was stirred at 50 ° C for 2 hours. 10.02 parts of the salt represented by formula (I-2102-a) were added to the resulting reaction mixture and stirred at 50 ° C for 10 hours. The resulting reaction mixture was cooled to 23 ° C, 25 parts of ion-exchanged water was added, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was isolated. 25 parts of ion-exchanged water was added to the resulting organic layer, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was isolated. This water washing procedure was repeated five times. The obtained organic layer was concentrated, and 3 parts of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue. After stirring at 23°C for 30 minutes, the supernatant was removed and the mixture was concentrated to obtain 11.44 parts of the salt represented by formula (I-2102). MASS(ESI(+)Spectrum):M + 841.0 MASS(ESI(-)Spectrum):M - 407.1

[0256] Example 6: Synthesis of salt represented by formula (I-2088) 2.64 parts of the compound represented by formula (I-2-c) and 50 parts of chloroform were mixed and stirred at 23 ° C for 30 minutes, after which 1.62 parts of the compound represented by formula (I-2-b) were added, the mixture was heated to 50 ° C, and stirred at 50 ° C for 2 hours. 7.96 parts of the salt represented by formula (I-2088-a) were added to the resulting reaction mixture and stirred at 50 ° C for 10 hours. The resulting reaction mixture was cooled to 23 ° C, 25 parts of ion-exchanged water was added, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was extracted. 25 parts of ion-exchanged water was added to the resulting organic layer, and the mixture was stirred at 23 ° C for 30 minutes, after which the organic layer was separated and the organic layer was extracted. This water washing procedure was repeated five times. The obtained organic layer was concentrated, and 3 parts of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue. After stirring at 23°C for 30 minutes, the supernatant was removed and the mixture was concentrated to obtain 9.24 parts of the salt represented by formula (I-2088). MASS(ESI(+)Spectrum):M + 634.9 MASS(ESI(-)Spectrum):M - 407.1

[0257] Resin synthesis The compounds (monomers) used in the synthesis of resin (A) are shown below. Hereinafter, these compounds will be referred to as "monomer (a1-1-3)" etc. according to their formula numbers. TIFF2023143845000164.tif103168

[0258] Example 7 [Synthesis of Resin A1] Monomers (a1-1-3), (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-898) were mixed in a molar ratio of 20:35:3:12:25:5 (monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-898)). 1.5 times the total mass of all monomers was mixed with this monomer mixture. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, and the mixture was heated at 73°C for approximately 5 hours. After that, a 25% aqueous solution of tetramethylammonium hydroxide was added to the polymerization reaction solution, and after stirring for 12 hours, the layers were separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate a resin, which was then filtered and recovered to give a resin with a weight-average molecular weight of approximately 5.6 × 10 3 Resin A1 having the following structural units was obtained in a yield of 63%. TIFF2023143845000165.tif64161

[0259] Example 8 [Synthesis of Resin A2] Monomers (a1-1-3), (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-912) were mixed in a molar ratio of 20:35:3:12:25:5 (monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-912)). 1.5 times the total mass of all monomers was mixed with this monomer mixture. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, and the mixture was heated at 73°C for approximately 5 hours. After that, a 25% aqueous solution of tetramethylammonium hydroxide was added to the polymerization reaction solution, and after stirring for 12 hours, the layers were separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate a resin, which was then filtered and recovered to give a resin with a weight-average molecular weight of approximately 5.4 × 10 3 Resin A2 having the following structural units was obtained in a yield of 65%. JPEG2023143845000166.jpg75158

[0260] Example 9 [Synthesis of Resin A3] Monomers (a1-1-3), (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-1990) were mixed in a molar ratio of 20:35:3:12:25:5 (monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-1990)). This monomer mixture was then mixed with 1.5 times the total mass of all monomers of methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, and the mixture was heated at 73°C for approximately 5 hours. After that, a 25% aqueous solution of tetramethylammonium hydroxide was added to the polymerization reaction solution, and after stirring for 12 hours, the layers were separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate a resin, which was then filtered and recovered to give a resin with a weight-average molecular weight of approximately 5.3 × 10 3 Resin A3 having the following structural units was obtained in a yield of 65%. JPEG2023143845000167.jpg76159

[0261] Example 10 [Synthesis of Resin A4] Monomers (a1-1-3), (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-2116) were mixed in a molar ratio of 20:35:3:12:25:5 (monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-2116)). This monomer mixture was then mixed with 1.5 times the total mass of all monomers of methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, and the mixture was heated at 73°C for approximately 5 hours. After that, a 25% aqueous solution of tetramethylammonium hydroxide was added to the polymerization reaction solution, and after stirring for 12 hours, the layers were separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate a resin, which was then filtered and recovered to give a resin with a weight-average molecular weight of approximately 5.4 × 10 3 Resin A4 having the following structural units was obtained in a yield of 62%. JPEG2023143845000168.jpg64159

[0262] Example 11 [Synthesis of Resin A5] Monomers (a1-1-3), (a1-2-6), (a2-1-3), (a3-4-2), 3,4-diacetoxystyrene, and (I-912) were mixed in a molar ratio of 20:35:3:12:25:5 (monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):3,4-diacetoxystyrene:monomer (I-912)). This monomer mixture was then mixed with 1.5 times the total mass of all monomers of methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, and the mixture was heated at 73°C for approximately 5 hours. After that, a 25% aqueous solution of tetramethylammonium hydroxide was added to the polymerization reaction solution, and after stirring for 12 hours, the layers were separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate a resin, which was then filtered and recovered to give a resin with a weight-average molecular weight of approximately 5.4 × 10 3 Resin A5 having the following structural units was obtained in a yield of 64%. JPEG2023143845000169.jpg79165

[0263] Example 12 [Synthesis of Resin A6] Monomers (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-912) were used and mixed in a molar ratio of 55:3:12:25:5 (monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-912)). This monomer mixture was then mixed with 1.5 times the total mass of all monomers in methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, relative to the total monomer mass. The mixture was heated at 73°C for approximately 5 hours. A 25% aqueous solution of tetramethylammonium hydroxide was then added to the polymerization reaction mixture, which was then stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered and recovered to obtain a resin with a weight-average molecular weight of approximately 5.4 × 10 3 Resin A6 having the following structural units was obtained in a yield of 89%. JPEG2023143845000170.jpg63159

[0264] Example 13 [Synthesis of Resin A7] Monomers (a1-2-6), (a2-1-3), (a3-4-2), 3,4-diacetoxystyrene, and (I-912) were mixed in a molar ratio of 55:3:12:25:5 (monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):3,4-diacetoxystyrene:monomer (I-912)). This monomer mixture was then mixed with 1.5 times the total weight of all monomers of methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, relative to the total monomer amount, and the mixture was heated at 73°C for approximately 5 hours. A 25% aqueous solution of tetramethylammonium hydroxide was then added to the polymerization reaction mixture, which was then stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered and recovered to obtain a resin with a weight-average molecular weight of approximately 5.4 × 10 3 Resin A7 having the following structural units was obtained in a yield of 86%. JPEG2023143845000171.jpg82156

[0265] Example 14 [Synthesis of Resin A8] Monomers (a1-2-6), (a2-1-3), (a3-4-2), 3-acetoxystyrene, and (I-912) were used and mixed in a molar ratio of 55:3:12:25:5 (monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):3-acetoxystyrene:monomer (I-912)). This monomer mixture was then mixed with 1.5 times the total mass of all monomers in methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators to the resulting mixture at 1.2 mol% and 3.6 mol%, respectively, based on the total monomer mass. The mixture was heated at 73°C for approximately 5 hours. A 25% aqueous solution of tetramethylammonium hydroxide was then added to the polymerization reaction mixture, which was then stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered and recovered to obtain a resin with a weight-average molecular weight of approximately 5.3 × 10 3 Resin A8 having the following structural units was obtained in a yield of 79%. JPEG2023143845000172.jpg81159

[0266] Example 15 [Synthesis of Resin A9] Monomers (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-2102) were used and mixed in a molar ratio of 55:3:12:25:5 (monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-2102)). This monomer mixture was then mixed with 1.5 times the total weight of all monomers of methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, relative to the total monomer amount, and the mixture was heated at 73°C for approximately 5 hours. A 25% aqueous solution of tetramethylammonium hydroxide was then added to the polymerization reaction mixture, which was then stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered and recovered to obtain a resin with a weight-average molecular weight of approximately 5.6 × 10 3 Resin A9 having the following structural units was obtained in a yield of 86%. JPEG2023143845000173.jpg71161

[0267] Example 16 [Synthesis of Resin A10] Monomers (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-2088) were used and mixed in a molar ratio of 55:3:12:25:5 (monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-2088)). This monomer mixture was then mixed with 1.5 times the total mass of all monomers in methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, relative to the total monomer mass. The mixture was heated at 73°C for approximately 5 hours. A 25% aqueous solution of tetramethylammonium hydroxide was then added to the polymerization reaction mixture, which was then stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered and recovered to obtain a resin with a weight-average molecular weight of approximately 5.4 × 10 3 Resin A10 having the following structural units was obtained in a yield of 82%. JPEG2023143845000174.jpg72159

[0268] Example 17 [Synthesis of Resin A11] Monomers (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-2116) were used and mixed in a molar ratio of 55:3:12:25:5 (monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-2116)). This monomer mixture was then mixed with 1.5 times the total mass of all monomers in methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, relative to the total monomer mass. The mixture was heated at 73°C for approximately 5 hours. A 25% aqueous solution of tetramethylammonium hydroxide was then added to the polymerization reaction mixture, which was then stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered and recovered to obtain a resin with a weight-average molecular weight of approximately 5.6 × 10 3 Resin A11 having the following structural units was obtained in a yield of 84%. JPEG2023143845000175.jpg64139

[0269] Example 18 [Synthesis of Resin A12] Monomers (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (I-2116) were used and mixed in a molar ratio of 50:3:10:25:12 (monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (I-2116)). This monomer mixture was then mixed with 1.5 times the total mass of all monomers in methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, relative to the total monomer mass. The mixture was heated at 73°C for approximately 5 hours. A 25% aqueous solution of tetramethylammonium hydroxide was then added to the polymerization reaction mixture, which was then stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered and recovered to obtain a resin with a weight-average molecular weight of approximately 5.9 × 10 3 Resin A12 having the following structural units was obtained in a yield of 84%. JPEG2023143845000176.jpg45149

[0270] Synthesis Example 1 [Synthesis of Resin AX1] Monomers (a1-1-3), (a1-2-6), (a2-1-3), (a3-4-2), 4-acetoxystyrene, and (IX-1) were mixed in a molar ratio of 20:35:3:12:25:5 (monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene:monomer (IX-1)). 1.5 times the total mass of all monomers was mixed with methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, and the mixture was heated at 73°C for approximately 5 hours. After that, a 25% aqueous solution of tetramethylammonium hydroxide was added to the polymerization reaction solution, and after stirring for 12 hours, the layers were separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate a resin, which was then filtered and recovered to give a resin with a weight-average molecular weight of approximately 5.5 × 10 3 Resin AX1 having the following structural units was obtained in a yield of 63%. TIFF2023143845000177.tif36162

[0271] Synthesis Example 2 [Synthesis of Resin AA1] Monomers (a1-1-3), (a1-2-6), (a2-1-3), (a3-4-2), and 4-acetoxystyrene were mixed in a molar ratio of 20:35:3:15:27 (monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1-3):monomer (a3-4-2):4-acetoxystyrene). This monomer mixture was then mixed with 1.5 times the total mass of all monomers in methyl isobutyl ketone. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators to the resulting mixture at 1.2 mol% and 3.6 mol%, respectively, based on the total monomer mass. The mixture was heated at 73°C for approximately 5 hours. A 25% aqueous solution of tetramethylammonium hydroxide was then added to the polymerization reaction mixture, which was then stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered and recovered to obtain a resin with a weight-average molecular weight of approximately 5.5 × 10 3 Resin AA1 having the following structural units was obtained in a yield of 68%. JPEG2023143845000178.jpg38161

[0272] <Preparation of Resist Composition> As shown in Table 2, the following components were mixed and the resulting mixture was filtered through a fluororesin filter with a pore size of 0.2 μm to prepare a resist composition. [Table 2]

[0273] <Resin> A1 to A12, AX1, AA1: Resin A1 to Resin A12, Resin AX1, Resin AA1 <Salt (I)> I-898: A salt represented by the formula (I-898) I-912: A salt represented by the formula (I-912) I-1990: A salt represented by the formula (I-1990) I-2116: A salt represented by the formula (I-2116) <Acid generator> B1-25: Salt represented by formula (B1-25); synthesized by the method described in JP 2011-126869 A TIFF2023143845000180.tif2667IX-1: Synthesized by the method described in JP-A-2011-38092 TIFF2023143845000181.tif4762<Quencher (C)> C1: Synthesized by the method described in JP 2011-39502 A TIFF2023143845000182.tif4349<solvent> Compositions 1-17, 20, comparative compositions 1-4 Propylene glycol monomethyl ether acetate 400 parts Propylene glycol monomethyl ether 100 parts γ-butyrolactone 5 parts Compositions 18, 19 400 parts of methyl 2-hydroxyisobutyrate Propylene glycol monomethyl ether 100 parts γ-butyrolactone 5 parts

[0274] ...

Claims

1. An acid generator containing a salt represented by formula (I) or a structural unit represented by formula (IP). [In formula (I) and formula (IP), R １ , R ２ and R ３ are each independently a hydroxy group, —O—R １０ , -O-CO-OR １０ or -OL １ -CO-O-R １０ Represents. L １ represents an alkanediyl group having 1 to 6 carbon atoms. R ４ , R ５ , R ６ , R ７ , R ８ and R ９ each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. R １０ represents an acid labile group. A １ , A ２ and A ３ each independently represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. m1 represents an integer of 0 to 5, and when m1 is 2 or more, the groups in the parentheses may be the same or different. m2 represents an integer of 0 to 4, and when m2 is 2 or more, the groups in the parentheses may be the same or different. m3 represents an integer of 0 to 4, and when m3 is 2 or more, the groups in the parentheses may be the same or different. m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R ４ may be the same or different from each other. m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R ５ may be the same or different from each other. m6 represents an integer of 0 to 4, and when m6 is 2 or more, a plurality of R ６ may be the same or different from each other. m7 represents an integer of 0 to 5, and when m7 is 2 or more, a plurality of R ７ may be the same or different from each other. m8 represents an integer of 0 to 4, and when m8 is 2 or more, a plurality of R ８ may be the same or different from each other. m9 represents an integer of 0 to 4, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 0≦m1+m7≦5, 0≦m2+m8≦4, and 0≦m3+m9≦4. At least one of m1, m2, and m3 represents an integer of 1 or more. X ４ is a single bond, -CH 2 -, -O-, -S-, -CO-, -SO- or -SO ２ Represents -. Q ｂ１ and Q ｂ２ each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L ｂ１ represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ The - may be replaced by -O- or -CO-, and the hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y ｂ１ represents a single bond or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH ２ - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. R ｂｂ１ represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X １０ represents a single bond, *-O-**, *-CO-O-**, *-O-CO-O-** or *-Ax-Ph-Ay-**. Ph represents a phenylene group which may have a substituent. Ax represents one type of bond selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. Ay represents one type of bond selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. * and ** represent binding sites, * represents R ｂｂ１ represents the bonding site with the carbon atom to which it is attached. L １０ represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -SO ２ - or -CO- may be substituted.]

2. A １ But, ***-X ０１ -L ０１ - or ***-L ０１ -X ０１ - and A ２ But, ***-X ０２ -L ０２ - or ***-L ０２ -X ０２ - and A ３ But, ***-X ０３ -L ０３ - or ***-L ０３ -X ０３ - and X ０１ , X ０２ and X ０３ each independently represents —O—, —CO—, —S—, or —SO ２ represents -, L ０１ , L ０２ and L ０３ each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent. 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -, *** is R １ , R ２ or R ３ represents a bonding site with the benzene ring to which it is bonded.

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

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

5. R １ , R ２ and R ３ each independently represents a hydroxy group, —O—R １０ or -OL １ -CO-O-R １０ 2. The acid generator according to claim 1, wherein

6. R １０ 2. The acid generator according to claim 1, wherein the acid labile group is a group represented by formula (1a) or a group represented by formula (2a). [In formula (1a), R aa1 , R aa2 and R aa3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms. * indicates a binding site.] [In formula (2a), R aa1’ and R aa2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R aa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa2’ and R aa3’ are bonded to each other and bonded to -C-X ａ - together with - to form a heterocyclic group having 3 to 20 carbon atoms, and -CH contained in the hydrocarbon group and the heterocyclic group ２ - may be replaced by -O- or -S-. X a represents an oxygen atom or a sulfur atom. * indicates a binding site.]

7. Y ｂ１ is a single bond or an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (the —CH ２ - represents -O-, -CO-, -S- or -SO ２ 2. The acid generator according to claim 1, wherein:

8. Y ｂ１ 8. The acid generator according to claim 7, wherein is a cyclohexanediyl group, an adamantanediyl group, a norbornanediyl group, an adamantanelactonediyl group, or a norbornanelactonediyl group.

9. X １０ is a single bond or a group represented by the formula (X １０ -1) ~Formula (X １０ 2. The acid generator according to claim 1, wherein the acid generator is a group represented by any one of the following formulas: [Formula (X)] １０ -1) ~ Equation (X) １０ -10) in the middle, *, ** are binding sites, * is R ｂｂ１ represents the bonding site with the carbon atom to which it is attached. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4.

10. X １０ is a single bond or a group represented by the formula (X １０ -1), formula (X １０ -5') and formula (X １０ 10. The acid generator according to claim 9, wherein the acid generator is a group represented by any one of the following formulas: [Formula (X １０ -1), formula (X １０ -5') and formula (X １０ -6') medium, *, ** are binding sites, * is R ｂｂ１ represents the bonding site with the carbon atom to which the

11. L １０ is a single bond, an alkanediyl group having 1 to 6 carbon atoms (provided that the —CH 2 - may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms (however, the cyclic hydrocarbon group may have a substituent, and the -CH 2 - is -O-, -S-, -SO ２ - or -CO-) or a group formed by combining an alkanediyl group having 1 to 6 carbon atoms with a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and the -CH contained in the alkanediyl group may be replaced by - or -CO-). 2 - may be replaced by -O- or -CO-, and -CH contained in the cyclic hydrocarbon group 2 - is -O-, -S-, -SO ２ 2. The acid generator according to claim 1, wherein:

12. A resist composition comprising the acid generator according to any one of claims 1 to 11.

13. A salt represented by formula (I) The resist composition according to claim 12, further comprising a resin containing a structural unit (a1) having an acid labile group.

14. Contains a resin containing a structural unit represented by formula (IP), 13. The resist composition according to claim 12, wherein the resin containing the structural unit represented by formula (IP) further contains a structural unit (a1) having an acid labile group.

15. 15. The resist composition according to claim 14, further comprising a salt represented by formula (I).

16. 14. The resist composition according to claim 13, wherein the structural unit (a1) having an acid labile group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), and a structural unit represented by formula (a1-2): [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L ａ１ and L ａ２ are each independently —O— or *—O—(CH ２ ) ｋ１ represents —CO—O—, k1 represents an integer of 1 to 7, and * represents the bonding site with —CO—. R a01 , R ａ４ and R ａ５ each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. R ａ６ and R ａ７ each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these. m1' represents an integer of 0 to 14; n1 represents an integer of 0 to 10. n1′ represents an integer of 0 to 3.]

17. 14. The resist composition according to claim 13, wherein the resin containing the structural unit (a1) having an acid labile group further contains a structural unit represented by formula (a2-A): [In formula (a2-A), R a50 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a50 is a single bond or *-X a51 - (A a52 -X a52 ) nｂ -, * represents -R a50 represents the bonding site with the carbon atom to which it is bonded. A a52 represents an alkanediyl group having 1 to 8 carbon atoms. X a51 and X a52 each independently represents —O—, —CO—O—, or —O—CO—. nb represents 0 or 1. mb represents an integer of 0 to 4. When mb is an integer of 2 or more, a plurality of R a51 may be the same or different.]

18. The resist composition according to claim 12, further comprising a salt represented by formula (B1): [In formula (B1), Q ｂ１ and Q ｂ２ each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L ｂ１ represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ The - may be replaced by -O- or -CO-, and the hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y represents an optionally substituted methyl group or an optionally substituted alicyclic hydrocarbon group having 3 to 24 carbon atoms, and —CH ２ - is -O-, -S-, -SO ２ It may be replaced by - or -CO-. Z ＋ represents an organic cation.

19. 13. The resist composition according to claim 12, further comprising a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator.

20. (1) a step of applying the resist composition according to claim 12 onto a substrate; (2) a step of drying the applied composition to form a composition layer; (3) exposing the composition layer to light; (4) a step of heating the composition layer after exposure; and (5) developing the composition layer after heating; A method for producing a resist pattern comprising:

21. A salt represented by formula (I): [In formula (I), R １ , R ２ and R ３ are each independently a hydroxy group, —O—R １０ , -O-CO-OR １０ or -OL １ -CO-O-R １０ Represents. L １ represents an alkanediyl group having 1 to 6 carbon atoms. R ４ , R ５ , R ６ , R ７ , R ８ and R ９ each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. R １０ represents an acid labile group. A １ , A ２ and A ３ each independently represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. m1 represents an integer of 0 to 5, and when m1 is 2 or more, the groups in the parentheses may be the same or different. m2 represents an integer of 0 to 4, and when m2 is 2 or more, the groups in the parentheses may be the same or different. 。 m3 represents an integer of 0 to 4, and when m3 is 2 or more, the groups in the parentheses may be the same or different. stomach. m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R ４ may be the same or different good. m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R ５ are the same but different Good too. m6 represents an integer of 0 to 4, and when m6 is 2 or more, a plurality of R ６ are the same but different That's fine. m7 represents an integer of 0 to 5, and when m7 is 2 or more, a plurality of R ７ are the same but different It is also possible. m8 represents an integer of 0 to 4, and when m8 is 2 or more, a plurality of R ８ are the same but different It may be so. m9 represents an integer of 0 to 4, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 0≦m1+m7≦5, 0≦m2+m8≦4, and 0≦m3+m9≦4. At least one of m1, m2, and m3 represents an integer of 1 or more. X ４ is a single bond, -CH 2 -, -O-, -S-, -CO-, -SO- or -SO ２ Represents -. Q ｂ１ and Q ｂ２ each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L ｂ１ represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ The - may be replaced by -O- or -CO-, and the hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y ｂ１ represents a single bond or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH ２ - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. R ｂｂ１ represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X １０ represents a single bond, *-O-**, *-CO-O-**, *-O-CO-O-** or *-Ax-Ph-Ay-**. Ph is a phenyl group which may have a substituent. represents an ylene group. Ax is one selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. Represents the bond species of a species. Ay represents one type of bond selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. * and ** represent binding sites, * represents R ｂｂ１ represents the bonding site with the carbon atom to which it is attached. L １０ represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -SO ２ - or -CO- replaced It may be possible to do so.]

22. A １ But, ***-X ０１ -L ０１ - or ***-L ０１ -X ０１ - and A ２ But, ***-X ０２ -L ０２ - or ***-L ０２ -X ０２ - and A ３ But, ***-X ０３ -L ０３ - or ***-L ０３ -X ０３ - and X ０１ , X ０２ and X ０３ each independently represents —O—, —CO—, —S—, or —SO ２ represents -, L ０１ , L ０２ and L ０３ each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent. 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -, *** is R １ , R ２ or R ３ The salt according to claim 21, wherein represents a bonding site with the benzene ring to which it is attached.

23. X ０１ , X ０２ and X ０３ The salt according to claim 22, wherein each of the groups independently represents -O- or -S-.

24. L ０１ , L ０２ and L ０３ each independently represents a single bond or an alkanediyl group having 1 to 6 carbon atoms (the —CH 2 The salt according to claim 22 or 23, wherein - may be replaced by -O- or -CO-.

25. R １ , R ２ and R ３ each independently represents a hydroxy group, —O—R １０ or -OL １ -CO-O-R １０ 23. The salt according to claim 21 or 22, wherein

26. R １０ The salt according to claim 21 or 22, wherein the acid labile group is a group represented by formula (1a) or a group represented by formula (2a). [In formula (1a), R aa1 , R aa2 and R aa3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms. * indicates a binding site.] [In formula (2a), R aa1’ and R aa2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R aa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa2’ and R aa3’ are bonded to each other and bonded to -C-X ａ - together with - to form a heterocyclic group having 3 to 20 carbon atoms, and -CH contained in the hydrocarbon group and the heterocyclic group ２ - may be replaced by -O- or -S-. X a represents an oxygen atom or a sulfur atom. * indicates a binding site.]

27. Y ｂ１ is a single bond or an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (the —CH ２ - represents -O-, -CO-, -S- or -SO ２ 23. The salt according to claim 21 or 22, wherein:

28. Y ｂ１ The salt according to claim 27, wherein is a cyclohexanediyl group, an adamantanediyl group, a norbornanediyl group, an adamantanelactonediyl group, or a norbornanelactonediyl group.

29. X １０ is a single bond or a group represented by the formula (X １０ -1) ~Formula (X １０ The salt according to claim 21 or 22, wherein the group is a group represented by any one of the following: [Formula (X)] １０ -1) ~ Equation (X) １０ -10) in the middle, *, ** are binding sites, * is R ｂｂ１ represents the bonding site with the carbon atom to which it is attached. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4.

30. X １０ is a single bond or a group represented by the formula (X １０ -1), formula (X １０ -5') and formula (X １０ The salt according to claim 29, wherein the group is a group represented by any one of the following: [Formula (X １０ -1), formula (X １０ -5') and formula (X １０ -6') medium, *, ** are binding sites, * is R ｂｂ１ represents the bonding site with the carbon atom to which the

31. L １０ is a single bond, an alkanediyl group having 1 to 6 carbon atoms (provided that the —CH 2 - may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms (however, the cyclic hydrocarbon group may have a substituent, and the -CH 2 - is -O-, -S-, -SO ２ - or -CO-) or a group formed by combining an alkanediyl group having 1 to 6 carbon atoms with a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and the -CH contained in the alkanediyl group may be replaced by - or -CO-). 2 - may be replaced by -O- or -CO-, and -CH contained in the cyclic hydrocarbon group 2 - is -O-, -S-, -SO ２ 23. The salt according to claim 21 or 22, wherein:

32. A resin comprising a structural unit represented by formula (IP): [In the formula (IP), R １ , R ２ and R ３ are each independently a hydroxy group, —O—R １０ , -O-CO-OR １０ or -OL １ -CO-O-R １０ Represents. L １ represents an alkanediyl group having 1 to 6 carbon atoms. R ４ , R ５ , R ６ , R ７ , R ８ and R ９ each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. R １０ represents an acid labile group. A １ , A ２ and A ３ each independently represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. m1 represents an integer of 0 to 5, and when m1 is 2 or more, the groups in the parentheses may be the same or different. m2 represents an integer of 0 to 4, and when m2 is 2 or more, the groups in the parentheses may be the same or different. 。 m3 represents an integer of 0 to 4, and when m3 is 2 or more, the groups in the parentheses may be the same or different. stomach. m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R ４ may be the same or different good. m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R ５ are the same but different Good too. m6 represents an integer of 0 to 4, and when m6 is 2 or more, a plurality of R ６ are the same but different That's fine. m7 represents an integer of 0 to 5, and when m7 is 2 or more, a plurality of R ７ are the same but different It is also possible. m8 represents an integer of 0 to 4, and when m8 is 2 or more, a plurality of R ８ are the same but different It may be so. m9 represents an integer of 0 to 4, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 0≦m1+m7≦5, 0≦m2+m8≦4, and 0≦m3+m9≦4. At least one of m1, m2, and m3 represents an integer of 1 or more. X ４ is a single bond, -CH 2 -, -O-, -S-, -CO-, -SO- or -SO ２ Represents -. Q ｂ１ and Q ｂ２ each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L ｂ１ represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ The - may be replaced by -O- or -CO-, and the hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y ｂ１ represents a single bond or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH ２ - represents -O-, -CO-, -S- or -SO ２ It may be replaced with -. R ｂｂ１ represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X １０ represents a single bond, *-O-**, *-CO-O-**, *-O-CO-O-** or *-Ax-Ph-Ay-**. Ph is a phenyl group which may have a substituent. represents an ylene group. Ax is one selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. Represents the bond species of a species. Ay represents one type of bond selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, and a carbonate ester bond. * and ** represent binding sites, * represents R ｂｂ１ represents the bonding site with the carbon atom to which it is attached. L １０ represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -SO ２ - or -CO- replaced It may be possible to do so.]

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