Resist composition and method for producing resist pattern

Abstract

To provide a resist composition and the like which allow a resist pattern having good line edge roughness to be produced.SOLUTION: The resist composition contains a compound represented by formula (I) and an acid generator. [In the formula (I), X0 represents a C1-72 hydrocarbon group having a halogen atom, -CH2- contained in the hydrocarbon group may be substituted with -O-, -S-, -CO- or -SO2-, and the hydrocarbon group may have a substituent other than a halogen atom; Rc1, Rc2 and Rc3 each independently represent a hydrogen atom, a halogen atom or a C1-48 hydrocarbon group, the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be substituted with -O-, -CO-, -S- or -SO2-; nc1 represents an integer of 1-6; and when nc1 is 2 or more, a plurality of groups in parentheses may be the same as or different from each other.]SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] Patent Document 1 describes a resist composition containing a compound represented by the following structural formula, a resin having an acid-labile group, and an acid generator. TIFF2025097318000001.tif1684

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] An object of the present invention is to provide a resist composition that forms a resist pattern having better line edge roughness (LER) than a resist pattern formed from the above resist composition.

Means for Solving the Problems

[0005] The present invention includes the following inventions. 〔1〕A resist composition containing a compound represented by formula (I) and an acid generator. TIFF2025097318000002.tif2684[In formula (I), X 0 represents a hydrocarbon group having 1 to 72 carbon atoms having a halogen atom, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and the hydrocarbon group may have a substituent other than a halogen atom. R c1 , R c2 and Rc3 each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 48 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-. nc1 represents any integer from 1 to 6. When nc1 is 2 or more, the groups within the plurality of parentheses may be the same as or different from each other. [2] X 0 is an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group formed by combining two or more selected from a chain hydrocarbon group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, and an aromatic hydrocarbon group having 6 to 36 carbon atoms (the alicyclic hydrocarbon group and the aromatic hydrocarbon group have a fluorine atom, an iodine atom, or a fluorinated alkyl group having 1 to 4 carbon atoms, and may have a hydroxy group, the chain hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group, and -CH2- contained in the alicyclic hydrocarbon group and the chain hydrocarbon group may be replaced by -O- or -CO-). The resist composition according to [1]. [3] The resist composition according to [1] or [2], wherein the acid generator is a salt represented by formula (B1). TIFF2025097318000003.tif1392[In formula (B1), L b1 represents a single bond or a (nb1 + 1)-valent hydrocarbon group which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-. L b2 represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-. Y b1 represents a methyl group which may have a substituent or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, or -CO-. nb1 represents an integer from 1 to 6. When nb1 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. Z + represents an organic cation. further contains a [4] resin, and the resin is the resist composition according to any one of [1] to [3] containing a structural unit represented by formula (a2 - A). TIFF2025097318000004.tif30128 [In formula (a2 - A), R a2 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a27 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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 a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced by -O-, -CO-, or -NR a28 -. R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a2 represents a single bond or a carbonyl group. nA2 represents an integer from 1 to 5. When nA2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. na21 represents an integer from 0 to 4. When na21 is 2 or more, the plurality of R a27 may be the same as or different from each other. mc represents an integer from 0 to 2. [5] The resin further contains a structural unit having an acid-labile group, and the structural unit having an acid-labile group includes 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), a structural unit represented by formula (a1-2), a structural unit represented by formula (a1-4), a structural unit represented by formula (a1-5), and a structural unit represented by formula (a1-6). The resist composition according to any one of [1] to [4]. TIFF2025097318000005.tif44143 [In formula (a1-0), formula (a1-1), and formula (a1-2), L a01 、L a1 and L a2 each independently represents -O- or *-O-(CH2) k1 -CO-O-, k1 represents an integer of any one of 1 to 7, and * represents a 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 formed by combining these, and the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. 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, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. m1’ represents an integer of any one of 0 to 14. n1 represents an integer of any one of 0 to 10. n1’ represents an integer of any one of 0 to 3. ] TIFF2025097318000006.tif31117[In formula (a1-4), R a1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a17 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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 a11 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a18 -. R a18 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a1 represents a single bond or a carbonyl group. R a34 and R a35 each independently represent 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 a divalent hydrocarbon group having 2 to 20 carbon atoms together with the -C-O- to which they are bonded, and -CH2- contained in the hydrocarbon group and the divalent hydrocarbon group may be replaced by -O- or -S-. na1 represents any integer from 1 to 5, and when na1 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. na11 represents any integer from 0 to 4, and when na11 is 2 or more, the plurality of R a17 may be the same as or different from each other. mc represents any integer from 0 to 2.] TIFF2025097318000007.tif4558[In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. Z a1 is a single bond or *-(CH2) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, and * represents the bonding site with L 51 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.] TIFF2025097318000008.tif3682[In formula (a1-6), R a61 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a62 R a63 and R a64 each independently represents an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, or R a62 and R a63 are bonded to each other to form a ring having 3 to 20 carbon atoms together with the carbon atom to which they are bonded. X a61 represents a single bond, -CO-O-* or -CO-NR a65 -*, * represents the bonding site with Ar, and R a65 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 represents a single bond, *-O-L a61 - or *-CO-O-L a62 -, * represents the bonding site with Ar, and L a61 and L a62 each independently represents an alkanediyl group having 1 to 4 carbon atoms. Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.] ​The step of applying the resist composition according to any one of [6][1] to [5] onto a substrate, (2) The step of drying the applied resist composition to form a composition layer, (3) The step of exposing the composition layer, (4) The step of heating the exposed composition layer, and (5) The step of developing the heated composition layer, a method for manufacturing a resist pattern including the above steps. [Advantages of the Invention]

[0006] By using the resist composition of the present invention, a resist pattern can be manufactured with good line edge roughness (LER). [Modes for Carrying Out the Invention]

[0007] In this specification, the term "(meth)acrylic monomer" means "at least one of acrylic monomers and methacrylic monomers". Similarly, notations such as "(meth)acrylate" and "(meth)acrylic acid" also represent the same meaning. Among the groups described in this specification, those that can take both a linear structure and a branched structure may be either of them. For -CH2- contained in a hydrocarbon group or the like, it is -O-, -S-, -CO-, -SO-, -NR XWhen replaced by -(X is any sign) or -SO2-, the same examples shall apply to each group, and the number of carbon atoms before replacement shall be taken as the number of carbon atoms of hydrocarbon groups and the like. The "combined group" means a group formed by bonding two or more of the exemplified groups, and the valences of these groups may be appropriately changed depending on the bonding form. "Derived from" or "induced from" means that the polymerizable C=C bond contained in the molecule becomes a single bond (-C-C- group) by polymerization or any hydrogen atom becomes a bonding site. When stereoisomers exist, all stereoisomers are included. The "acid-labile group" means a group that, when contacted with an acid (e.g., trifluoromethanesulfonic acid, etc.), the leaving group leaves to form a hydrophilic group (e.g., hydroxy group or carboxy group, etc.). The "base-labile group" means a group that, when contacted with a base (e.g., trimethylamine, tetramethylammonium hydroxide, etc.), the leaving group leaves to form a hydrophilic group (e.g., carboxy group or hydroxy group, etc.). Each group may have any position and number of hydrogen atoms contained in the group replaced by a bond depending on the number of substituents and the like. The number of carbon atoms in the substituent is not included in the number of carbon atoms of the group being substituted. In this specification, the "solid content of the resist composition" means the total of the components excluding the solvent (E) described later from the total amount of the resist composition.

[0008] [Resist Composition] The resist composition of the present invention contains a compound represented by formula (I) (hereinafter sometimes referred to as "compound (I)") and an acid generator (hereinafter sometimes referred to as "acid generator (B)"). The resist composition of the present invention may further contain a resin. Examples of the resin include resins containing structural units having acid-labile groups (hereinafter sometimes referred to as "resin (A)"). The "acid-labile group" here means a group having a leaving group that, upon contact with an acid, the leaving group leaves to convert to a structural unit having a hydrophilic group (e.g., hydroxy group or carboxy group). Further, resins other than resin (A) may be contained. The resist composition of the present invention preferably further contains a quencher (hereinafter sometimes referred to as "quencher (C)") such as a salt that generates an acid having a lower acidity than the acid generated from the acid generator, and more preferably contains a solvent (hereinafter sometimes referred to as "solvent (E)").

[0009] <Compound (I)> The resist composition of the present invention contains Compound (I). TIFF2025097318000009.tif2684[In formula (I), all symbols have the same meanings as described above.]

[0010] In formula (I), X 0 Examples of the (nc1)-valent hydrocarbon group of include a group obtained by removing (nc1-1) hydrogen atoms from a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group (monocyclic or polycyclic such as a spiro ring, a condensed ring, or a bridged ring), a monovalent aromatic hydrocarbon group, and a monovalent group formed by combining two or more of these groups. The number of carbon atoms of the hydrocarbon group is preferably 1 to 48, more preferably 1 to 42, still more preferably 1 to 36, even more preferably 1 to 30, and even still more preferably 1 to 24. Examples of the chain hydrocarbon group include a group obtained by removing (nc1-1) hydrogen atoms from an alkyl group or an alkenyl group. The alkyl group may be linear or branched, and specifically includes a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a heptadecyl group, etc. Examples of the alkenyl group include an ethenyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, an isooctenyl group, and a nonenyl group. The number of carbon atoms in the chain hydrocarbon group is preferably from 1 to 36, more preferably from 1 to 24, still more preferably from 1 to 20, even more preferably from 1 to 18, yet even more preferably from 1 to 12, and still even more preferably from 1 to 10. Examples of the alicyclic hydrocarbon group include a group obtained by removing (nc1-1) hydrogen atoms from a monocyclic or polycyclic cycloalkyl group. Examples of the monocyclic cycloalkyl group include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. Examples of the polycyclic cycloalkyl group include a cycloalkyl group having a crosslinked structure, a cycloalkyl group in which two or more rings are condensed, or a cycloalkyl group in which two rings are spiro-bonded. Examples of the cycloalkyl group having a crosslinked structure include a norbornyl group, an adamantyl group, and the like. Examples of the cycloalkyl group in which two or more rings are condensed include a bicyclo[4,4,0]decane group, a steroid group (steroid skeleton), and the like. Examples of the cycloalkyl group in which two rings are spiro-bonded include a spirocyclic cycloalkyl group in which one cycloalkyl group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group and a cycloalkyl group having 5 to 8 carbon atoms are spiro-bonded. Further, a double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group. More specifically, examples of the alicyclic hydrocarbon group include those represented by the following formula. When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 20, still more preferably 3 to 18, even more preferably 3 to 12, still even more preferably 3 to 10, and yet even more preferably 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 6 to 24, more preferably 6 to 20, still more preferably 6 to 18, even more preferably 6 to 12, and still even more preferably 7 to 12. Examples of the aromatic hydrocarbon group include a group obtained by removing (nc1 - 1) hydrogen atoms from an aryl group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a fluorenyl group, and the like. More specifically, examples of the aromatic hydrocarbon group include those represented by the following formula. TIFF2025097318000011.tif1384 The number of carbon atoms in the aromatic hydrocarbon group is preferably 4 to 24, more preferably 4 to 20, still more preferably 4 to 18, even more preferably 5 to 14, still even more preferably 5 to 10, and yet even more preferably 6 to 10. X 0 When -CH2- contained in the hydrocarbon group of X is replaced by -O-, -CO-, -S- or -SO2-, the number of carbon atoms before replacement is taken as the number of carbon atoms of the hydrocarbon group. X 0Among the hydrocarbon groups, examples of the group in which -CH2- contained in the chain hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2- include a hydroxy group (a group in which -CH2- contained in the methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in the ethyl group is replaced by -O-CO-), a carbonyl group (a group in which -CH2- contained in the methylene group is replaced by -CO-), an oxy group (a group in which -CH2- contained in the methylene group is replaced by -O-), a thiol group (a group in which -CH2- contained in the methyl group is replaced by -S-), a sulfonyl group (a group in which -CH2- contained in the methylene group is replaced by -SO2-), an alkoxy group (a group in which -CH2- at any position contained in the alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -CO-), an alkylthio group (a group in which -CH2- at any position contained in the alkyl group is replaced by -S-), an alkylsulfonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -SO2-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -CO-O-), an alkoxycarbonyloxy group (a group in which -CH2-CH2-CH2- at any position contained in the alkyl group is replaced by -O-CO-O-), an alkanedioxy group (a group in which -CH2- at any position contained in the alkanedioyl group is replaced by -O-), an alkanedioxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkanedioyl group is replaced by -O-CO-), an alkanedioylcarbonyl group (a group in which -CH2- at any position contained in the alkanedioyl group is replaced by -CO-), an alkanedioylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in the alkanedioyl group is replaced by -CO-O-), an alkanedithio group (a group in which -CH2- at any position contained in the alkanedioyl group is replaced by -S-), an alkanediosulfonyl group (a group in which -CH2- at any position contained in the alkanedioyl group isGroups replaced by -SO2-, etc. Examples of the alkoxy group include alkoxy groups having 1 to 71 carbon atoms, such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group and the like. The number of carbon atoms of the alkoxy group may be 1 to 36 or 1 to 12, preferably 1 to 6, more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkylthio group include alkylthio groups having 1 to 71 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, undecylthio group and the like. The number of carbon atoms of the alkylthio group may be 1 to 36 or 1 to 12, preferably 1 to 6, more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 71 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group and the like. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 72 carbon atoms, such as acetyl group, propionyl group and butyryl group and the like. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 71 carbon atoms, such as acetyloxy group, propionyloxy group, butyryloxy group and the like. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 70 carbon atoms, such as butoxycarbonyloxy group and the like. The carbon number of the alkoxycarbonyl group may be 2 to 36 or 2 to 12, preferably 2 to 6, more preferably 2 to 4, and still more preferably 2 or 3. The carbon number of the alkylcarbonyl group may be 2 to 36 or 1 to 12, preferably 2 to 6, more preferably 2 to 4, and still more preferably 2 or 3. The carbon number of the alkylcarbonyloxy group may be 2 to 36 or 2 to 12, preferably 2 to 6, more preferably 2 to 4, and still more preferably 2 or 3. The carbon number of the alkoxycarbonyloxy group may be 2 to 34 or 2 to 12, preferably 2 to 6, more preferably 2 to 4, and still more preferably 2 or 3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 71 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, octylsulfonyl group, 2-ethylhexylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group and the like. The carbon number of the alkylsulfonyl group may be 1 to 36 or 1 to 12, preferably 1 to 6, more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyl oxy group include alkanediyl oxy groups having 1 to 71 carbon atoms, such as a methylene oxy group, an ethylene oxy group, a propanediyl oxy group, a butanediyl oxy group, and a pentanediyl oxy group. The number of carbon atoms in the alkanediyl oxy group may be 1 to 36 or 1 to 12, preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkanediyl oxycarbonyl group include alkanediyl oxycarbonyl groups having 2 to 71 carbon atoms, such as a methylene oxycarbonyl group, an ethylene oxycarbonyl group, a propanediyl oxycarbonyl group, and a butanediyl oxycarbonyl group. Examples of the alkanediyl carbonyl group include alkanediyl carbonyl groups having 2 to 72 carbon atoms, such as a methylene carbonyl group, an ethylene carbonyl group, a propanediyl carbonyl group, a butanediyl carbonyl group, and a pentanediyl carbonyl group. Examples of the alkanediyl carbonyloxy group include alkanediyl carbonyloxy groups having 2 to 71 carbon atoms, such as a methylene carbonyloxy group, an ethylene carbonyloxy group, a propanediyl carbonyloxy group, and a butanediyl carbonyloxy group. The number of carbon atoms in the alkanediyl oxycarbonyl group may be 2 to 36 or 2 to 12, preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyl carbonyl group may be 2 to 36 or 2 to 12, preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyl carbonyloxy group may be 2 to 36 or 2 to 12, preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3. Examples of the alkanediyl thio group include alkanediyl thio groups having 1 to 71 carbon atoms, such as a methylene thio group, an ethylene thio group, and a propylene thio group. The number of carbon atoms in the alkanediyl thio group may be 1 to 36 or 1 to 12, preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 71 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, and a propylenesulfonyl group. The number of carbon atoms of the alkanediylsulfonyl group may be 1 to 36 or 1 to 12, preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. X 0 Among the hydrocarbon groups of 0 , examples of the group in which -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2- include groups containing structures such as cyclic ethers, cyclic ketones, cyclic esters (lactones), cyclic thioethers, cyclic acetals, and cyclic sulfonic acid esters (sultones). Specifically, alicyclic hydrocarbon groups represented by the following formulas can be mentioned. The bonding position of the alicyclic hydrocarbon groups mentioned in the following formulas can be any position. TIFF2025097318000012.tif49165X 0 Among the hydrocarbon groups of 0 , -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-. Examples of the group in which -CH2- is replaced by -O- or -S- include groups derived from a furan ring or a thiophene ring, respectively. Specifically, aromatic hydrocarbon groups represented by the following formulas can be mentioned. TIFF2025097318000013.tif1326 Examples of the group in which -CH2- contained in the group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- also include the following groups. The bonding site can be any position. As a group combining two or more of the linear hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group, examples include a group combining the above linear hydrocarbon group and the above alicyclic hydrocarbon group, a group combining the above linear hydrocarbon group and the above aromatic hydrocarbon group, a group combining the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group, and a group combining the above linear hydrocarbon group, the above alicyclic hydrocarbon group, and the above aromatic hydrocarbon group. As a group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, it may be a condensed ring. X 0 The hydrocarbon group has a halogen atom as a substituent. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. X 0 Examples of substituents other than the halogen atom that the hydrocarbon group of X 0 may have include a cyano group, a nitro group, etc. X 0 When X 0 is a group combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a linear hydrocarbon group such as an alkyl group, the linear hydrocarbon group such as an alkyl group may be substantially regarded as a substituent that the alicyclic hydrocarbon group or the aromatic hydrocarbon group has. Also, X 0 When -CH2- contained in the linear hydrocarbon group contained in the hydrocarbon group of X 0 is replaced by -O-, -CO-, -S-, or -SO2-, the hydrocarbon group of X 0 can substantially have substituents such as a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, a thiol group, an alkylthio group, an alkylsulfonyl group, etc. The hydrogen atoms contained in an alkyl group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, etc. may be replaced by a halogen atom. Examples of the alkyl group having a halogen atom include haloalkyl groups having 1 to 12 carbon atoms such as alkyl fluoride groups having 1 to 12 carbon atoms, alkyl chloride groups having 1 to 12 carbon atoms, alkyl bromide groups having 1 to 12 carbon atoms, and alkyl iodide groups having 1 to 12 carbon atoms. Examples of the haloalkyl group include perfluoroalkyl groups having 1 to 12 carbon atoms (such as trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, iodomethyl group, etc. The number of carbon atoms of the haloalkyl group is preferably 1 to 9, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0011] X 0 The hydrocarbon group represented by 0 is preferably an aliphatic hydrocarbon group having 2 to 72 carbon atoms having a halogen atom or a perfluoroalkyl group having 1 to 6 carbon atoms (wherein -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and the aliphatic hydrocarbon group may have a substituent other than a halogen atom), or a hydrocarbon group having 6 to 72 carbon atoms containing an aromatic hydrocarbon group having 6 to 36 carbon atoms having a halogen atom or a perfluoroalkyl group having 1 to 6 carbon atoms (wherein -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and the hydrocarbon group may have a substituent other than a halogen atom). More preferably, it is a group formed by combining two or more selected from an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a chain hydrocarbon group having 1 to 18 carbon atoms, each having a halogen atom or a C1-C4 fluoroalkyl group (the alicyclic hydrocarbon group, the chain hydrocarbon group, and the aromatic hydrocarbon group may have a hydroxy group, and -CH2- contained in the alicyclic hydrocarbon group and the chain hydrocarbon group may be replaced by -O- or -CO-). In each of the above groups, the halogen atom is preferably a fluorine atom or an iodine atom. In formula (I), X 0 is more preferably a group represented by formula (X 0 -1). TIFF2025097318000015.tif4494[In formula (X 0 -1), nc2 represents an integer from 0 to 6. When nc2 is 2 or more, the groups within the plurality of parentheses may be the same or different from each other. nc3 represents an integer from 0 to 6, satisfying 1 ≦ nc2 + nc3 ≦ 6. When nc3 is 2 or more, the groups within the plurality of parentheses may be the same or different from each other. R c11 and R c22 each independently represent a halogen atom or a C1-C6 fluoroalkyl group, and -CH2- contained in the fluoroalkyl group may be replaced by -O- or -CO-. nc4 and nc5 each represent any integer from 0 to 5, and at least one of nc4 and nc5 of 1 or more is 1 or more. L c1 、L c2 and L c3Each independently represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms, wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent. W c1 and W c2 Each independently represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, -CH= or -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a substituent. ** represents a bonding site with an oxygen atom. The total number of carbon atoms of each group does not exceed 72. R c11 and R c22 The halogen atoms of are the same halogen atoms as those exemplified by X 0 In addition, the alkyl fluoride groups of and are alkyl groups in which one or more hydrogen atoms of the alkyl groups exemplified by X c11 and R c22 are replaced by fluorine atoms within the range allowed by the upper limit of the number of carbon atoms. 0 L c1 L c2 and L c3 The chain hydrocarbon groups of are groups similar to the chain hydrocarbon groups exemplified by X 0 as long as the upper limit of the number of carbon atoms is allowed. W c1 and W c2 The alicyclic hydrocarbon groups and aromatic hydrocarbon groups of are groups similar to the alicyclic hydrocarbon groups and aromatic hydrocarbon groups exemplified by X 0 as long as the upper limit of the number of carbon atoms is allowed. L c1 L c2 and L c3 The substituents that the chain hydrocarbon groups of may have and the substituents that the alicyclic hydrocarbon groups and aromatic hydrocarbon groups of W c1 and W c2 may have are X 0Examples of the substituent that the hydrocarbon group may have include the same groups as those exemplified as the substituent. R c11 and R c22 are each independently preferably an iodine atom, a fluorine atom, or a perfluoroalkyl group having 1 to 3 carbon atoms. nc4 is preferably any integer from 1 to 5. nc5 is preferably any integer from 0 to 4, and more preferably any integer from 0 to 3. L c1 、L c2 and L c3 are each independently preferably a single bond or an alkanediyl group having 1 to 6 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by -O- or -CO-. The alkanediyl group may be substituted by a fluorine atom). L c1 and L c2 are each independently preferably a single bond, a methylene group, an ethylene group, or a group in which an ester bond bonded to W c1 is combined with an alkanediyl group having 1 to 3 carbon atoms, and L c3 is preferably a single bond, a methylene group, an ethylene group, or a group in which an ester bond bonded to W c2 is combined with an alkanediyl group having 1 to 3 carbon atoms. In formula (X 0 -1), the alicyclic hydrocarbon group and the aromatic hydrocarbon group of W c1 and W c2 are each independently preferably the alicyclic hydrocarbon group and the aromatic hydrocarbon group represented below. In the alicyclic hydrocarbon group and the aromatic hydrocarbon group represented below, * and ** represent the bonding sites. In the case of W c1 , * represents a hydrogen atom or the bonding site with R c11 , and in the case of W c2 , * represents the bonding site with L c2 . In the case of W c1 , ** represents a hydrogen atom, a substituent, or the bonding site with L c1 , and at least one of ** is L c1represents the binding site to. W c2 In the case of, ** is a hydrogen atom, R c22 , a substituent or L c3 represents the binding site to, and at least one of ** is L c3 represents the binding site to. In addition, in the alicyclic hydrocarbon group represented below, -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-. When -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2-, it is preferable that an ether ring, an ester ring (lactone ring), a carbonate ester ring, a sulfonic acid ester ring (sultone ring) or an acetal ring is formed. TIFF2025097318000016.tif36168W c1 and W c2 are each independently preferably a group derived from a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a norbornane ring, a norbornane lactone ring, an adamantane ring, an adamantane lactone ring, a benzene ring, a naphthalene ring, or a combination of these rings. In the cyclopentane ring, the cyclohexane ring, the cycloheptane ring and the cyclooctane ring, two -CH2- contained in the cyclopentane ring, the cyclohexane ring, the cycloheptane ring and the cyclooctane ring may be replaced by -O- or -S- to form an acetal ring or a thioacetal ring. In the norbornane ring, -CH2- contained in the norbornane ring may be replaced by -O- or -S- to form an oxonorbornane ring or a thionorbornane ring. The cyclopentane ring, the cyclohexane ring, the cycloheptane ring, the cyclooctane ring, the norbornane ring, the norbornane lactone ring, the adamantane ring, the adamantane lactone ring, the benzene ring and the naphthalene ring may have a substituent such as a hydroxy group, a methoxy group or an ethoxy group in addition to R c11 and R c22 In addition, it may have a substituent such as a hydroxy group, a methoxy group or an ethoxy group. Also, W c1is preferably a spirocyclic alicyclic hydrocarbon group in which a cyclopentane ring, a cyclohexane ring, a norbornane ring or an adamantane ring is bonded to a cyclopentane ring, a cyclohexane ring, a cycloheptane ring or a cyclooctane ring. In the spirocyclic alicyclic hydrocarbon group, two -CH2- groups contained in the cyclopentane ring, the cyclohexane ring, the cycloheptane ring or the cyclooctane ring may be each replaced by -O- or -S- to form an acetal ring or a thioacetal ring. The cyclopentane ring, the cyclohexane ring, the norbornane ring and the adamantane ring may have a substituent such as a hydroxy group, a methoxy group or an ethoxy group other than R c11 In addition, the cyclopentane ring, the cyclohexane ring, the norbornane ring and the adamantane ring may have a substituent such as a hydroxy group, a methoxy group or an ethoxy group.

[0012] R c1 、R c2 and R c3 Examples of the halogen atoms of R R c1 、R c2 and R c3 include fluorine atom, chlorine atom, bromine atom, iodine atom and the like. R c1 、R c2 and R c3 The monovalent chain hydrocarbon group, monovalent alicyclic hydrocarbon group, monovalent aromatic hydrocarbon group and monovalent group formed by combining two or more of these groups of R 0 are the same groups as those exemplified for the hydrocarbon group of X c1 、R c2 and R c3 In the hydrocarbon group of R 0 the groups in which -CH2- contained in the hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2- are also the same groups as those in which -CH2- contained in the hydrocarbon group of X R c1 、R c2 and Rc3 Examples of the substituent that the hydrocarbon group may have include a halogen atom, a cyano group, a nitro group, and the like. R c1 、R c2 and R c3 When R 0 etc. are hydrocarbon groups having a halogen atom, examples of such groups include chain hydrocarbon groups having a halogen atom such as a haloalkyl group, alicyclic hydrocarbon groups having a halogen atom, and aromatic hydrocarbon groups having a halogen atom (in each group, -CH2- contained may be replaced by -O- or -CO- or the like). Examples of these groups include the same groups as those exemplified by X 0 etc. within the range where the upper limit of the number of carbon atoms permits. R c1 、R c2 and R c3 are each independently preferably a hydrogen atom, a halogen atom or a hydrocarbon group having 1 to 28 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-), more preferably a hydrogen atom, a halogen atom, a chain hydrocarbon group having 1 to 10 carbon atoms (the chain hydrocarbon group may have a substituent, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), or a group combining a chain hydrocarbon group having 1 to 8 carbon atoms and a cyclic hydrocarbon group having 3 to 18 carbon atoms (the chain hydrocarbon group and the cyclic hydrocarbon group may have a substituent, and -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced by -O- or -CO-), still more preferably a hydrogen atom, a halogen atom or a chain hydrocarbon group having 1 to 8 carbon atoms (the chain hydrocarbon group may have a halogen atom, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), and still more preferably a hydrogen atom, a fluorine atom, an iodine atom, an alkyl group having 1 to 6 carbon atoms, a fluorinated alkyl group having 1 to 6 carbon atoms, a hydroxy group or an alkoxy group having 1 to 5 carbon atoms.

[0013] Compound (I) includes compounds represented by the following formula. TIFF2025097318000017.tif242161

[0014] The compound (I) contained in the resist composition of the present invention may be used alone or in combination of two or more. The total content of the compound (I) is usually 0.001 to 20% by mass, preferably 0.005 to 15% by mass, more preferably 0.01 to 10% by mass based on the solid content of the resist composition. The compound (I) can be obtained from commercially available compounds or synthesized and obtained by conventionally known methods.

[0015] <Acid generator (B)> As the acid generator (B) contained in the resist composition of the present invention, either a nonionic compound or an ionic compound may be used. Examples of the nonionic compound include sulfonate esters (e.g., 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxy ketone, diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfone, ketosulfone, sulfonyldiazomethane), etc. Representative examples of the ionic compound include onium salts containing an onium cation (e.g., diazonium salt, phosphonium salt, sulfonium salt, iodonium salt). Examples of the anion of the onium salt include sulfonic acid anion, benzenesulfonyl anion, sulfonylimide anion, sulfonylmethide anion, and carboxylic acid anion, etc. Further, the acid generator (B) may be a structural unit having an acid generating function, for example, it may be a resin containing a structural unit (a7) described later.

[0016] As the acid generator (B), compounds that generate acid upon irradiation, 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, US Patent No. 3,779,778, US Patent No. 3,849,137, German Patent No. 3914407, European Patent No. 126,712, etc., can be used. Further, compounds produced by known methods may also be used. The acid generator (B) may be used alone or in combination of two or more. The acid generator (B) may be an acid generator having an acid-labile group. For example, the compound or resin serving as the acid generator may contain a partial structure that becomes an acid-labile group, and the acid-labile group preferably contains the group (1) or group (2) described later. When the resist composition of the present invention contains a compound having an acid-labile group, a resin containing a structural unit having an acid-labile group may not be included.

[0017] A preferred form of the acid generator (B) includes a salt represented by the formula (B1) (hereinafter sometimes referred to as "salt (B1)" or "acid generator (B1)"). TIFF2025097318000018.tif1392[In the formula, all symbols represent the same meaning as described above.] L b1 As the (nb1 + 1)-valent hydrocarbon group of, hydrogen atoms are removed from a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, a monovalent aromatic hydrocarbon group, and a monovalent group formed by combining two or more of these groups, and one or more L b2 groups that bond to are mentioned. The number of carbon atoms of the hydrocarbon group is preferably 1 to 48, more preferably 1 to 42, still more preferably 1 to 36, even more preferably 1 to 30, still even more preferably 1 to 24, and even more preferably 1 to 18. Examples of the chain hydrocarbon group include a group obtained by removing nb1 hydrogen atoms from an alkyl group or an alkenyl group. The alkyl group may be linear or branched, and specific examples include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, iso-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, heptadecyl group, and the like. Examples of the alkenyl group include ethenyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, tert-butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, isooctenyl group, nonenyl group. The number of carbon atoms of the chain hydrocarbon group is preferably from 1 to 36, more preferably from 1 to 24, still more preferably from 1 to 20, even more preferably from 1 to 18, even still more preferably from 1 to 12, and even more preferably from 1 to 10. Examples of the alicyclic hydrocarbon group include a group obtained by removing nb1 hydrogen atoms from a monocyclic or polycyclic cycloalkyl group. Examples of the monocyclic cycloalkyl group include cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like. Examples of the polycyclic cycloalkyl group include a cycloalkyl group having a crosslinked structure, a cycloalkyl group in which two or more rings are condensed, or a cycloalkyl group in which two rings are spiro-bonded. Examples of the cycloalkyl group having a crosslinked structure include norbornyl group, adamantyl group, and the like. Examples of the cycloalkyl group in which two or more rings are condensed include bicyclo[4,4,0]decane group, steroid group (steroid skeleton), and the like. Examples of the cycloalkyl group in which two rings are spiro-bonded include a spirocyclic cycloalkyl group in which one cycloalkyl group selected from the group consisting of cyclopentyl group, cyclohexyl group, norbornyl group, and adamantyl group and a cycloalkyl group having 5 to 8 carbon atoms are spiro-bonded. A double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group. More specifically, examples of the alicyclic hydrocarbon group include those represented by the following formula. TIFF2025097318000019.tif26168 When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 20, still more preferably 3 to 18, even more preferably 3 to 12, even still more preferably 3 to 10, and even more preferably 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 6 to 24, more preferably 6 to 20, still more preferably 6 to 18, even more preferably 6 to 12, and even still more preferably 7 to 12. Examples of the aromatic hydrocarbon group include a group obtained by removing nb1 hydrogen atoms from an aryl group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a fluorenyl group, and the like. More specifically, examples of the aromatic hydrocarbon group include those represented by the following formula. TIFF2025097318000020.tif1184 The number of carbon atoms in the aromatic hydrocarbon group is preferably 4 to 24, more preferably 4 to 20, still more preferably 4 to 18, even more preferably 5 to 14, even still more preferably 5 to 10, and even more preferably 6 to 10. L b1 When -CH2- contained in the hydrocarbon group of L is replaced by -O-, -CO-, -S- or -SO2-, the number of carbon atoms before replacement is defined as the number of carbon atoms in the hydrocarbon group. L b1Among the hydrocarbon groups, examples of the group in which -CH2- contained in the chain hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2- include a hydroxy group (a group in which -CH2- contained in the methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in the ethyl group is replaced by -O-CO-), a carbonyl group (a group in which -CH2- contained in the methylene group is replaced by -CO-), an oxy group (a group in which -CH2- contained in the methylene group is replaced by -O-), an alkoxy group (a group in which -CH2- at any position contained in the alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -O-CO-), an alkylthio group (a group in which -CH2- at any position contained in the alkyl group is replaced by -S-), an alkylcarbonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in the alkyl group is replaced by -CO-O-), an alkylsulfonyl group (a group in which -CH2- at any position contained in the alkyl group is replaced by -SO2-), an alkanediyl-oxy group (a group in which -CH2- at any position contained in the alkanediyl group is replaced by -O-), an alkanediyl-oxycarbonyl group (a group in which -CH2-CH2- at any position contained in the alkanediyl group is replaced by -O-CO-), an alkanediyl-carbonyl group (a group in which -CH2- at any position contained in the alkanediyl group is replaced by -CO-), an alkanediyl-carbonyloxy group (a group in which -CH2-CH2- at any position contained in the alkanediyl group is replaced by -CO-O-), an alkanediyl-thio group (a group in which -CH2- at any position contained in the alkanediyl group is replaced by -S-), an alkanediyl-sulfonyl group (a group in which -CH2- at any position contained in the alkanediyl group is replaced by -SO2-), and the like. These replaced groups include those similar to the groups exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms. L b1Among the hydrocarbon groups, examples of the group in which -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2- include groups containing structures such as cyclic ethers, cyclic ketones, cyclic esters (lactones), cyclic thioethers, cyclic acetals, cyclic sulfonic acid esters (sultones), etc. Specifically, alicyclic hydrocarbon groups represented by the following formulas can be mentioned. The bonding position of the alicyclic hydrocarbon group mentioned in the following formulas can be any position. TIFF2025097318000021.tif49165L b1 Among the hydrocarbon groups, -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-. Examples of the group in which -CH2- is replaced by -O- or -S- include groups derived from a furan ring or a thiophene ring, respectively. Specifically, aromatic hydrocarbon groups represented by the following formulas can be mentioned. TIFF2025097318000022.tif1326Examples of the group in which -CH2- contained in a group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- include those similar to the groups exemplified in this specification within the range where the upper limit of the number of carbon atoms permits. Examples of the group combining two or more of a chain hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group include a group combining the above chain hydrocarbon group and the above alicyclic hydrocarbon group, a group combining the above chain hydrocarbon group and the above aromatic hydrocarbon group, a group combining the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group, and a group combining the above chain hydrocarbon group, the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group. The group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group may be a condensed ring. L b2 Examples of the divalent hydrocarbon group include a divalent chain hydrocarbon group, a divalent alicyclic hydrocarbon group, a divalent aromatic hydrocarbon group, and a group combining two or more of these groups, and a group obtained by removing one hydrogen atom from a monovalent hydrocarbon group and bonding to Y b1 and bonding groups. L b2The divalent chain hydrocarbon group, divalent alicyclic hydrocarbon group, divalent aromatic hydrocarbon group, and divalent group formed by combining two or more of these groups are each, within the range permitted by the upper limit of the number of carbon atoms, L b1 Examples include groups obtained by removing one hydrogen atom from the monovalent chain hydrocarbon group, monovalent alicyclic hydrocarbon group, monovalent aromatic hydrocarbon group, and monovalent group formed by combining two or more of these groups exemplified by b1 . L b1 and L b2 Examples of the substituent that the hydrocarbon group of may have include a halogen atom, a cyano group, a nitro group, etc. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. L b1 and L b2 When is a group formed by combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group with a chain hydrocarbon group, substantially, the chain hydrocarbon group may be regarded as a substituent that the alicyclic hydrocarbon group or aromatic hydrocarbon group has. Also, when the -CH2- of the chain hydrocarbon group contained in the hydrocarbon group of L b1 and L b2 is replaced by -O-, -CO-, -S-, or -SO2-, the hydrocarbon group of L b1 and L b2 can substantially have substituents such as a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, a thiol group, an alkylthio group, an alkylsulfonyl group, etc. Y b1 Examples of the cyclic hydrocarbon group of include an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group. Y b1 The alicyclic hydrocarbon group and aromatic hydrocarbon group of are each the same as the alicyclic hydrocarbon group and aromatic hydrocarbon group exemplified by L b1 and, when having no substituent, may be a monovalent alicyclic hydrocarbon group and aromatic hydrocarbon group. Y b1 Examples of the substituent that the methyl group of may have include a halogen atom, a cyano group, a hydroxy group, a nitro group, etc. Yb1 Examples of the substituent that the cyclic hydrocarbon group of may have include a halogen atom, a cyano group, a nitro group, or a hydrocarbon group having 1 to 18 carbon atoms that may have a halogen atom, a cyano group or a nitro group. -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-. Y b1 The number of carbon atoms of the hydrocarbon group that the cyclic hydrocarbon group of may have is Y b1 is not included in the number of carbon atoms of the cyclic hydrocarbon group of. Y b1 Examples of the hydrocarbon group having 1 to 18 carbon atoms that the cyclic hydrocarbon group of may have as a substituent include a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group combining these groups. Examples of a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group combining two or more of these groups include, within the range allowed by the upper limit of the number of carbon atoms, L b1 are the same groups as those exemplified for the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and a group combining two or more of these groups exemplified in L. Also, Y b1 Examples of the group in which -CH2- contained in the hydrocarbon group having 1 to 18 carbon atoms that the cyclic hydrocarbon group of may have as a substituent is replaced by -O-, -S-, -CO- or -SO2- include, within the range allowed by the upper limit of the number of carbon atoms, the same groups as those exemplified for the group in which -CH2- contained in the hydrocarbon group of Lb1 is replaced by -O-, -S-, -CO- or -SO2-. Also, Y b1 Examples of the hydrocarbon group having 1 to 18 carbon atoms that the cyclic hydrocarbon group of may have as a substituent may constitute a protecting group or a leaving group (an acid-labile group or a base-labile group) generally used in the art. Examples of the anion of the salt represented by the formula (B1) include, for example, an anion represented by the following formula (B1-A1) (hereinafter sometimes referred to as "anion (B1-A1)") or an anion represented by the formula (B1-A2) (hereinafter sometimes referred to as "anion (B1-A2)"). TIFF2025097318000023.tif31125[In the formula (B1-A1), L b2 and Y b1represents the same meaning as formula (B1). Q b1 、Q b2 、Q b3 and Q b4 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. z1 represents any integer from 0 to 6. When z1 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. X 1 represents -O-CO-, -CO-O-, -O-CO-O-, or -O-. L b3 represents a single bond or an (nb2 + 1)-valent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-. nb2 represents any integer from 1 to 3. When nb2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other.] Q b1 、Q b2 、Q b3 and Q b4 Examples of the alkyl group of Q, Q, Q, and Q 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 、Q b2 、Q b3 and Q b4 Examples of the perfluoroalkyl group of Q, Q, Q, and Q include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, and a perfluorohexyl group. Q b1 and Q b2 are Q b1 and Q b2It is preferably included in at least one of them with a fluorine atom or a perfluoroalkyl group, more preferably a fluorine atom or a perfluoroalkyl group, still more preferably a fluorine atom or a trifluoromethyl group, and even more preferably both are fluorine atoms. Q b3 and Q b4 are each independently preferably a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, and Q b3 is preferably a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, and Q b4 is preferably a hydrogen atom or a fluorine atom.

[0018] z1 is preferably any integer from 0 to 3, and more preferably 0, 1 or 2. X 1 is preferably -O-CO- or -CO-O-.

[0019] L b3 As the hydrocarbon group in, within the range allowed by the upper limit of the number of carbon atoms, the same hydrocarbon groups as exemplified for L in formula (B1) can be mentioned. b1 can be mentioned. L b3is a single bond, an optionally substituted chain hydrocarbon group having 1 to 12 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an optionally substituted alicyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms (wherein -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-), or a group formed by combining two or more of these groups, and is preferably a single bond, a chain hydrocarbon group having 1 to 6 carbon atoms or a group represented by the following formula (Lb3-1). When -CH2- contained in the chain hydrocarbon group is replaced by -O- or -CO-, the number thereof is preferably 1 to 4, and preferably one -CH2-CH2- contained in the chain hydrocarbon group is replaced by -O-CO- or -CO-O-, or one -CH2-CH2-CH2- contained in the chain hydrocarbon group is replaced by -O-CO-O-. TIFF2025097318000024.tif1682[In the formula (Lb3-1), nb2 represents the same meaning as the formula (B1-A1). L b31 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms, -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent. W b3 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a substituent. * and ** represent bonding sites, and * represents the bonding site with X 1 and represents the bonding site with.] In the formula (Lb3-1), L b31 The chain hydrocarbon group of is, as long as the upper limit of the number of carbon atoms permits, L b1Examples thereof include the same groups as the chain hydrocarbon groups exemplified above. In formula (Lb3-1), W b3 The alicyclic hydrocarbon group and the aromatic hydrocarbon group of, as long as the upper limit of the number of carbon atoms permits, are the same groups as the alicyclic hydrocarbon groups and the aromatic hydrocarbon groups exemplified above for L b1 Examples thereof include the same groups as the alicyclic hydrocarbon groups and the aromatic hydrocarbon groups exemplified above. In formula (Lb3-1), L b31 The substituents that the chain hydrocarbon group of may have and W b3 The substituents that the alicyclic hydrocarbon group and the aromatic hydrocarbon group of may have are the same groups as the substituents exemplified as the substituents that the hydrocarbon group of L b1 may have. L b31 is preferably a single bond or an alkanediyl group having 1 to 6 carbon atoms (in the alkanediyl group, -CH2- contained therein may be replaced by -O- or -CO-). Among them, the alicyclic hydrocarbon group and the aromatic hydrocarbon group of W b3 are preferably the alicyclic hydrocarbon group and the aromatic hydrocarbon group represented below. In the alicyclic hydrocarbon group and the aromatic hydrocarbon group represented below, * and ** represent the bonding sites, * represents the bonding site with X 1 or L b31 and ** represents a hydrogen atom, a substituent or the bonding site with L b2 and at least one ** represents the bonding site with L b2 In addition, in the alicyclic hydrocarbon group represented below, -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-. When -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2-, it is preferably to form an ether ring, an ester ring (lactone), a carbonate ester ring, a sulfonic acid ester ring (sultone) or an acetal ring. In formula (B1-A1), L b2is a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), preferably a single bond, -O-, -O-CO-, -CO-O-, -O-CO-O- or *-L b21 -X 2 -L b22 -**(L b21 and L b22 One of them represents a chain hydrocarbon group having 1 to 6 carbon atoms, and the other represents a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms. X 2 represents -O-, -CO-O-, -O-CO- or -O-CO-O-. * and ** represent bonding sites, and ** represents the bonding site with Y b1 But L b21 X 2 and L b22 The total number of carbon atoms of is 12 or less.) is more preferable. In formula (B1-A1), Y b1 is preferably a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (wherein -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-), more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-) or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and still more preferably an alicyclic hydrocarbon group having 3 to 16 carbon atoms which may have a substituent (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-) or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. Specifically, it is preferably a group represented by the following formula (Y1) to formula (Y36). In formula (Y1) to formula (Y36), R Yb represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms among the substituents which the cyclic hydrocarbon group of Y b1 may have, and R Yc represents a hydrogen atom or a substituent which the cyclic hydrocarbon group of Y b1 may have, and * represents L b2represents a binding site with. The alicyclic hydrocarbon group and aromatic hydrocarbon group represented by the following formula are not particularly shown in the following formula, but may have substituents that the cyclic hydrocarbon group of Y b1 may also have. TIFF2025097318000026.tif84158

[0020] As the anion represented by the formula (B1-A1), anions represented by the formulas (B1-A1-1) to (B1-A1-85) [hereinafter, may be referred to as "anion (B1-A1-1)" etc. according to the formula number] are preferable, and anions represented by any of the formulas (B1-A1-1) to (B1-A1-4), formula (B1-A1-9), formula (B1-A1-10), formulas (B1-A1-24) to (B1-A1-33), formulas (B1-A1-36) to (B1-A1-40), and formulas (B1-A1-47) to (B1-A1-85) are more preferable. TIFF2025097318000027.tif216161

[0021] TIFF2025097318000028.tif249151

[0022] TIFF2025097318000029.tif254163

[0023] Here, R i2 ~R i7 are, independently of each other, for example, an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group. R i8 is, for example, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a group formed by combining these, more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. L A41 is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Q b1 and Q b2 represent the same meaning as above. Examples of the anion represented by formula (B1-A1) specifically include the anions described in JP-A-2010-204646.

[0024] Preferred anions represented by formula (B1-A1) include anions represented by formula (B1a-1) to formula (B1a-70). Among them, anions represented by any of formula (B1a-1) to formula (B1a-4), formula (B1a-7) to formula (B1a-11), formula (B1a-14) to formula (B1a-30), and formula (B1a-31) to formula (B1a-70) are preferred. TIFF2025097318000030.tif186163

[0025] TIFF2025097318000031.tif252165

[0026] TIFF2025097318000032.tif69165

[0027] The anion represented by formula (B1-A2) is represented by the following formula. TIFF2025097318000033.tif2399[In formula (B1-A2), L b2 and Y b1 have the same meanings as in formula (B1). R b1 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and -CH2- contained in the alkyl group may be replaced by -O- or -CO-. nb4 represents any integer from 1 to 5. When nb4 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. nb3 represents any integer from 0 to 4. When nb3 is 2 or more, the plurality of R b1 may be the same as or different from each other. However, 1 ≦ nb4 + nb3 ≦ 5 is satisfied.]

[0028] In formula (B1-A2), L b2 hydrocarbon group of and Y b1Examples of the cyclic hydrocarbon group include, within the range permitted by the upper limit of the number of carbon atoms, L in formula (B1) b2 The hydrocarbon group of and Y b1 Examples of the cyclic hydrocarbon group of are the same as those exemplified for the hydrocarbon group of L b2 The hydrocarbon group of, Y b1 Regarding the methyl group of and the substituents that the cyclic hydrocarbon group may have, L in formula (B1) b2 The hydrocarbon group of, Y b1 Examples of the substituents that the methyl group of and the cyclic hydrocarbon group may have are the same as those exemplified for the substituents that the hydrocarbon group of L These hydrocarbon groups, methyl group and cyclic hydrocarbon group may have one substituent or a plurality of substituents. In formula (B1-A2), L b2 is preferably a chain hydrocarbon group having 1 to 12 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), more preferably *-CO-O-L b41 -(L b41 is a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms, and the -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-. * represents the bonding site with the benzene ring to which SO3 - is bonded. L b41 is preferably a single bond or a chain hydrocarbon group having 1 to 3 carbon atoms.). More preferably, it is *-CO-O-. Y b1 is preferably a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (the -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-), more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-) or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. Y in formula (B1-A1) b1 or L b1It is more preferable that it is an alicyclic hydrocarbon group or an aromatic hydrocarbon group exemplified above. Specifically, it is preferably a group represented by the above-described formulas (Y1) to (Y36), and more preferably a group represented by the above-described formulas (Y1) to (Y19). In formula (B1-A2), nb4 is preferably any integer from 1 to 4, more preferably any integer from 1 to 3, still more preferably 1 or 2, and even more preferably 2. When nb4 is 1 or 2, -L b2 -Y b1 The bonding position of is preferably the following structure which is the m-position substitution of the benzene ring with respect to the bonding position of SO3 - .

[0029] TIFF2025097318000034.tif2399[In the above formula, L b2 , Y b1 , R b1 , and nb3 represent the same meanings as in formula (B1-A2).] In formula (B1-A2), when nb4 is 2 or more, a plurality of L b2 and Y b1 are preferably the same group as each other.

[0030] R b1 Examples of the alkyl group having 1 to 6 carbon atoms for R include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, and hexyl group. The number of carbon atoms of the alkyl group is preferably 1 to 4, and more preferably 1 to 3. R b1 Examples of the halogen atom for R include fluorine atom, chlorine atom, bromine atom, and iodine atom. Examples of the group in which -CH2- contained in the alkyl group is replaced by -O- or -CO- include hydroxy group, carboxy group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, oxy group, carbonyl group, etc. These replaced groups include those similar to the groups exemplified in the present specification as long as the upper limit of the number of carbon atoms allows. R b1is independently preferably a halogen atom or an alkyl group having 1 to 4 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-), more preferably a fluorine atom, an iodine atom or an alkyl group having 1 to 3 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methoxy group or a methyl group. nb3 is preferably any integer from 0 to 3, more preferably any integer from 0 to 2. In one embodiment, nb3 is preferably 0. In another embodiment, nb3 is preferably 1 or 2. When nb3 is 1, R b1 is preferably a halogen atom, and R b1 is more preferably a fluorine atom or an iodine atom. When nb3 is 2, one of R b1 is preferably a halogen atom and the other is preferably a halogen atom or an alkyl group having 1 to 4 carbon atoms, and one of R b1 is more preferably a fluorine atom or an iodine atom and the other is more preferably a fluorine atom, an iodine atom or an alkyl group having 1 to 3 carbon atoms.

[0031] Examples of the anion represented by formula (B1-A2) include the following anions. Among them, the anions represented by formula (B2a-1) to formula (B2a-20) are preferred, and the anions represented by formula (B2a-1) to formula (B2a-11), formula (B2a-16) to formula (B2a-20) are more preferred. In the following anions, some of R b1 are omitted and may contain substituents not shown. TIFF2025097318000035.tif94163

[0032] In another form of the acid generator (B), a salt in which the anion of the salt represented by the formula (B1) is replaced with a sulfonylimide anion, a sulfonylmethide anion, or a carboxylic acid anion is also preferably used as the acid generator (B). Examples of the salt in which the anion is replaced with a sulfonylimide anion or a sulfonylmethide anion include a salt represented by the formula (B2) (hereinafter sometimes referred to as "salt (B2)" or "acid generator (B2)"). TIFF2025097318000036.tif1192[In the formula (B2), A 1 represents a nitrogen atom or a carbon atom. L b2’ represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-. Y b1’ represents a methyl group which may have a substituent or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-. nb5 represents an integer of 2 or 3. When A 1 is a nitrogen atom, nb5 is 2, and when A 1 is a carbon atom, nb5 is 3. The groups in a plurality of parentheses may be the same as or different from each other, and the groups in two parentheses may be bonded to form a ring containing A 1 . Z2 + represents an organic cation.]

[0033] In the formula (B2), examples of the hydrocarbon group, cyclic hydrocarbon group, and substituent of L b2’ and Y b1’ are the same groups as L b2 and Y b1 in the formula (B1-A1). L b2 ' is a single bond, *-L b23 -, *-L b23 -X 2 -, or *-L b23 -X 2 -W2 -X 3 -(L b23 represents a chain hydrocarbon group having 1 to 6 carbon atoms which may have a fluorine atom. X 2 and X 3 each independently represents -O-, -CO-O-, -O-CO-, -O-CO-O- or -O-. W 2 represents an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O- or -CO-. * represents the bonding site with SO2. It is preferably (). Y b1 ' is preferably a methyl group having a fluorine atom or a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (-CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-).), more preferably a trifluoromethyl group, 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-, -S-, -CO- or -SO2-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. Specifically, it is more preferably a trifluoromethyl group or a group represented by formula (Y1) to formula (Y36) exemplified in formula (B1-A1).

[0034] In formula (B2), when two -SO2-L b2 '-Y b1 ' together form a ring containing A 1 For example, an anion represented by formula (B2') can be mentioned. TIFF2025097318000037.tif21112[In formula (B2'), A 1 、Y b1 ’、L b2 ’ and nb5 have the same meanings as in formula (B2). W b4 represents a disulfonylimide ring or a disulfonylmethide ring having 2 to 12 carbon atoms which may have a fluorine atom.] W b4The disulfonylimide ring or disulfonylmethide ring has 3 to 12 carbon atoms, preferably 3 to 6 carbon atoms, and the hydrogen atom of the methylene group contained in the ring is preferably replaced by a fluorine atom.

[0035] Examples of the anion in the salt represented by formula (B2) include the following. Among them, the anions represented by formula (B3a-1) and formula (B3a-2) are preferred. Examples of the carboxylic acid anion include the following. However, the acid generator (B) having a carboxylic acid anion excludes the salt of formula (I). TIFF2025097318000039.tif41155

[0036] Z1 + and Z2 + Examples of the organic cation of and include organic onium cation, organic sulfonium cation, organic iodonium cation, organic ammonium cation, benzothiazolium cation, and organic phosphonium cation. Among these, organic sulfonium cation and organic iodonium cation are preferred, and arylsulfonium cation or aryl iodonium cation is more preferred. Specifically, cations represented by any of formula (b2-1) to formula (b2-5) (hereinafter, may be referred to as "cation (b2-1)" etc. according to the formula number) are included. TIFF2025097318000040.tif82161[In formula (b2-1) to formula (b2-5), R b4 ~R b6Each independently represents an aliphatic hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms, and the hydrogen atoms contained in the aliphatic hydrocarbon group may be substituted with a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. The hydrogen atoms contained in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a glycidyloxy group. The hydrogen atoms 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 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and the -CH2- contained in the ring may be replaced by -O-, -S-, or -CO-. R 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 any integer from 0 to 5. When m2 is 2 or more, the plurality of R b7 may be the same or different, and when n2 is 2 or more, the plurality of R b8 may be the same or different. R b9 and R b10 each independently represents an aliphatic hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and the -CH2- contained in the ring may be replaced by -O-, -S-, or -CO-. R 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, and 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 and may be bonded to each other to form a ring including -CH-CO- to which they are bonded, and -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R b13 ~R b18 and R b21 ~R b26 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 R b21 and R b22 and may be bonded to each other to form a ring containing a sulfur atom together with the benzene ring to which they are bonded, and -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R b27 ~R b29 each independently represents a hydrogen atom or a group containing an acid-labile group. L b31 and L b41 ~L b43 each independently represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent any integer from 0 to 5. q2 and r2 each independently represent any integer from 0 to 4. u2 represents 0 or 1. When o2 is 2 or more, a plurality of R b13are the same or different, and when p2 is 2 or more, a plurality of Rs b14 are the same or different, and when q2 is 2 or more, a plurality of Rs b15 are the same or different, and when r2 is 2 or more, a plurality of Rs b16 are the same or different, and when s2 is 2 or more, a plurality of Rs b17 are the same or different, and when t2 is 2 or more, a plurality of Rs b18 are the same or different. u3 represents any integer from 1 to 3 and satisfies 1 ≦ u3 + q23 ≦ 5. u4 and u5 each independently represent any integer from 0 to 3 and satisfy 0 ≦ u4 + o21 ≦ 5 and 0 ≦ u5 + p22 ≦ 5. o21, p22, q23, r24, t25, and s26 each independently represent any integer from 0 to 4. When u3, u4, and u5 are each 2 or more, the groups within the plurality of parentheses are each the same or different. When o21, p22, q23, r24, t25, and s26 are each 2 or more, a plurality of Rs b21 ~R b26 are each the same or different.] When u2 is 0, any one of o2, p2, q2, and r2 is 1 or more, and at least one of R b13 ~R b16 is preferably a halogen atom. When u2 is 1, any one of o2, p2, s2, t2, q2, and r2 is 1 or more, and at least one of R b13 ~R b18 is preferably a halogen atom. Furthermore, when u2 is 0, r2 is preferably 1 or more, more preferably 1. Also, when u2 is 0 and r2 is 1 or more, R b16 is preferably a halogen atom.

[0037] The aliphatic hydrocarbon group represents a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of the chain hydrocarbon group include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, and 2-ethylhexyl group. In particular, R b9 ~R b12 The chain hydrocarbon group is preferably a group having 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and cyclodecyl group. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl group, adamantyl group, norbornyl group, and the following groups. TIFF2025097318000041.tif11157 In particular, R b9 ~R b12 The alicyclic hydrocarbon group is preferably a group having 3 to 18 carbon atoms, more preferably a group having 4 to 12 carbon atoms.

[0038] Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include methylcyclohexyl group, dimethylcyclohexyl group, 2-methyladamantan-2-yl group, 2-ethyladamantan-2-yl group, 2-isopropyladamantan-2-yl group, methylnorbornyl group, and isobornyl group. In the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group, the total number of carbon atoms of the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 20 or less. The alkyl fluoride group represents an alkyl group having 1 to 12 carbon atoms and having a fluorine atom, and examples thereof include fluoromethyl group, difluoromethyl group, trifluoromethyl group, and perfluorobutyl group. The number of carbon atoms of the alkyl fluoride group is preferably 1 to 9, more preferably 1 to 6, and even more preferably 1 to 4.

[0039] Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, biphenyl group, naphthyl group, and phenanthryl group. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples of the aromatic hydrocarbon group having a chain hydrocarbon group include tolyl group, xylyl group, cumenyl group, mesityl group, p-ethylphenyl group, p-tert-butylphenyl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc., and examples of the aromatic hydrocarbon group having an alicyclic hydrocarbon group include p-cyclohexylphenyl group, p-adamantylphenyl group, etc. When the aromatic hydrocarbon group has a chain hydrocarbon group or an alicyclic hydrocarbon group, a chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms are preferred. Examples of the aromatic hydrocarbon group in which a hydrogen atom is substituted with an alkoxy group include p-methoxyphenyl group, etc. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as benzyl group, phenethyl group, phenylpropyl group, trityl group, naphthylmethyl group, naphthylethyl group, etc.

[0040] Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group, and dodecyloxy group, etc. Examples of the alkylcarbonyl group include acetyl group, propionyl group, and butyryl group, etc. Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom, and iodine atom, etc. Examples of the alkylcarbonyloxy group include methylcarbonyloxy group, ethylcarbonyloxy group, propylcarbonyloxy group, isopropylcarbonyloxy group, butylcarbonyloxy group, sec-butylcarbonyloxy group, tert-butylcarbonyloxy group, pentylcarbonyloxy group, hexylcarbonyloxy group, octylcarbonyloxy group, and 2-ethylhexylcarbonyloxy group, etc.

[0041] Rb4 and R b5 The ring formed by the combination of and the sulfur atom to which they are attached may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of such rings include those having 3 to 18 carbon atoms, preferably 4 to 18 carbon atoms. The ring containing a sulfur atom includes 3-membered to 12-membered rings, preferably 3-membered to 7-membered rings, and examples thereof include the following rings. * represents a bonding site. TIFF2025097318000042.tif24142

[0042] R b9 and R b10 The ring formed by the combination of and may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of such rings include 3-membered to 12-membered rings, preferably 3-membered to 7-membered rings. Examples include thiolan-1-ium ring (tetrahydrothiophenium ring), thian-1-ium ring, 1,4-oxathian-4-ium ring, etc. R b11 and R b12 The ring formed by the combination of and may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of such rings include 3-membered to 12-membered rings, preferably 3-membered to 7-membered rings. Examples include oxocycloheptane ring, oxocyclohexane ring, oxonorbornane ring, oxoadamantane ring, etc. R b27 ~R b29 Examples of the group containing an acid-labile group of ~ include -R c30 , -CO-O-R c30 or -L c10 -CO-O-R c30 The group represented by (L c10 represents an alkanediyl group having 1 to 6 carbon atoms, and R c30 represents an acid-labile group.). etc. are included. R b27 ~R b29 Examples of the acid-labile group of ~ include, for example, the group (1) or group (2) described later.

[0043] Among cations (b2-1) to (b2-5), preferably, cation (b2-1), cation (b2-4) or cation (b2-5). Examples of cation (b2-1) include the following cations. TIFF2025097318000043.tif150165 Examples of cation (b2-2) include the following cations. TIFF2025097318000044.tif16135 Examples of cation (b2-3) include the following cations. TIFF2025097318000045.tif21130 Examples of cation (b2-4) include the following cations. TIFF2025097318000046.tif122163 Examples of cation (b2-5) include the following cations. TIFF2025097318000047.tif115158

[0044] The acid generator (B) is a combination of the above-mentioned anion and the above-mentioned organic cation, and these can be arbitrarily combined. Examples of the acid generator (B) preferably include a combination of an anion represented by any of formula (B1a-1) to formula (B1a-4), formula (B1a-7) to formula (B1a-11), formula (B1a-14) to formula (B1a-30), formula (B1a-35) to formula (B1a-70), formula (B2a-1) to formula (B2a-11), formula (B2a-16) to formula (B2a-20), formula (B3a-1) to formula (B3a-3) or formula (B3a-11) to formula (B3a-14), and cation (b2-1), cation (b2-2), cation (b2-3), cation (b2-4) or cation (b2-5).

[0045] As the acid generator (B), those represented by formula (B1-1) to formula (B1-105), formula (B2-1) to formula (B2-20), and formula (B3-1) to formula (B3-28) are preferably mentioned. Among them, those containing an arylsulfonium cation are preferred, and those represented by formula (B1-1) to formula (B1-3), formula (B1-5) to formula (B1-7), formula (B1-11) to formula (B1-14), formula (B1-20) to formula (B1-26), formula (B1-29), formula (B1-31) to formula (B1-105), formula (B2-1) to formula (B2-20), and formula (B3-1) to formula (B3-28) are particularly preferred. TIFF2025097318000048.tif173168

[0046] TIFF2025097318000049.tif254163

[0047] TIFF2025097318000050.tif254165

[0048] TIFF2025097318000051.tif252161

[0049] TIFF2025097318000052.tif249163

[0050] TIFF2025097318000053.tif247150

[0051] TIFF2025097318000054.tif184158

[0052] In the resist composition of the present invention, the content of the acid generator (B) is 1% by mass or more and 45% by mass or less, preferably 1% by mass or more and 40% by mass or less, more preferably 3% by mass or more and 35% by mass or less, based on the solid content of the resist composition. Further, when the resist composition of the present invention contains the resin (A) described later, the content of the acid generator (B) is preferably 1 part by mass or more and 45 parts by mass or less, more preferably 1 part by mass or more and 40 parts by mass or less, still more preferably 3 parts by mass or more and 35 parts by mass or less, per 100 parts by mass of the resin (A). The resist composition of the present invention may contain one kind of the acid generator (B) alone or a plurality of kinds thereof.

[0053] <Resin (A)> The resin (A) contains a structural unit having an acid-labile group (hereinafter sometimes referred to as "structural unit (a1)"). The resin (A) preferably further contains a structural unit other than the structural unit (a1). Examples of the structural unit other than the structural unit (a1) include a structural unit having no acid-labile group (hereinafter sometimes referred to as "structural unit (s)") and a structural unit derived from other monomers known in the art.

[0054] 〈Structural unit (a1)〉 The structural unit (a1) is derived from a monomer having an acid-labile group (hereinafter sometimes referred to as "monomer (a1)"). The acid-labile group contained in the resin (A) is preferably a group represented by the formula (1) (hereinafter also referred to as "group (1)") and / or a group represented by the formula (2) (hereinafter also referred to as "group (2)"). TIFF2025097318000055.tif2298[In the 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 these, or R a1 and R a2are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * represents a bonding site. TIFF2025097318000056.tif2278[In formula (2), R a1’ and R a2’ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and 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 group having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded and X, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced with -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom. X represents an oxygen atom or a sulfur atom. na’ represents 0 or 1. * represents a bonding site.

[0055] R a1 , R a2 and R a3 Examples of the alkyl group in R R a1 , R a2 and R a3 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, etc. R a1 , R a2 and R a3The alicyclic hydrocarbon group in [compound] may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl group, adamantyl group, norbornyl group and the following group (* represents the bonding site). R a1 and R a2 and R a3 The number of carbon atoms of the alicyclic hydrocarbon group in [compound] is preferably 3 to 16. TIFF2025097318000057.tif10159R a1 and R a2 and R a3 Examples of the aromatic hydrocarbon group in [compound] include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group and the like. Examples of the combined group include a group formed by combining the above-mentioned alkyl group and alicyclic hydrocarbon group (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group and the like), an aralkyl group such as benzyl group, an aromatic hydrocarbon group having an alkyl group (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group and the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group and the like), an aryl-cycloalkyl group such as phenylcyclohexyl group and the like. Preferably, ma is 0 and na is 1. R a1 and R a2 When R a1 and R a2 and R a3 are bonded to each other to form an alicyclic hydrocarbon group, examples of -C(R TIFF2025097318000058.tif28138

[0056] 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 combining these groups are R a1 , R a2 and R a3 Examples of the groups include the same groups as those listed in the above. R a2’ and R a3’ When they are bonded to each other to form a heterocyclic group together with the carbon atom to which they are bonded and X, -C(R a1’ )(R a2’ )-XR a3’ Examples of the groups include the following: * represents a binding site. TIFF2025097318000059.tif19124R a1’ and R a2’ At least one of these is preferably a hydrogen atom. na' is preferably 0. R a1 , R a2 , R a3 , R a1 , R a2’ and R a3’ The halogen atom which may be contained includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0057] 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. As the group, a tert-butoxycarbonyl group is preferable. In formula (1), R a1 , R a2 together with the carbon atom to which they are attached form an adamantyl group, Ra3 A group in which R is an alkyl group, ma = 0, and na = 1. In formula (1), R a1 and R a2 are each independently an alkyl group, R a3 is an adamantyl group, ma = 0, and na = 1. Specific examples of the group (1) include the following groups. * represents the bonding site. TIFF2025097318000060.tif150163

[0058] Specific examples of the group (2) include the following groups. * represents the bonding site. TIFF2025097318000061.tif56153

[0059] 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. Among the (meth)acrylic monomers having an acid-labile group, those having an alicyclic hydrocarbon group with 5 to 20 carbon atoms are preferably mentioned. If a resin (A) having a structural unit derived from a monomer (a1) having a bulky structure such as an alicyclic hydrocarbon group is used in the resist composition, the resolution of the resist pattern can be improved.

[0060] Examples of the structural unit derived from the (meth)acrylic monomer having the 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, it is at least one structural unit selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2), more preferably at least one or two structural units selected from the group consisting of structural unit (a1-1) and structural unit (a1-2). These may be used alone or in combination of two or more. TIFF2025097318000062.tif44143 [In formula (a1-0), formula (a1-1) and formula (a1-2), all symbols have the same meaning as defined above.]

[0061] R a01 , R a4 and R a5 The halogen atom in the formula (I) includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R a01 , R a4 and R a5 Examples of the alkyl group which may have a halogen atom in the above formula 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, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, and an iodomethyl 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. The alkyl group is preferably a methyl group or an ethyl group, and more preferably a methyl group. R a01 , R a4 and R a5 is preferably a hydrogen atom or a methyl group, and more preferably a methyl group. L a01 , L a1 and L a2 is preferably an oxygen atom or *-O-(CH2) k01 It is -CO-O- (wherein k01 is preferably an integer of any one of 1 to 4, more preferably 1), and more preferably an oxygen atom. R a02 , R a03 , R a04 , R a6 and R a7Examples of the alkyl group, alkenyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and a group combining these groups in formula (1) are the groups represented by R a1 , R a2 and R a3 . R a02 , R a03 , and R a04 . The alkyl group in R , R a6 and R a7 is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and still more preferably a methyl group. R a6 and R a7 . The alkyl group in R , R a02 , R a03 , R a04 , R a6 and R a7 is preferably an alkenyl group having 2 to 6 carbon atoms, more preferably an ethenyl group, a propenyl group, an isopropenyl group, or a butenyl group. R a02 , R a03 , R a04 , R a6 and R a7 . The number of carbon atoms of the alicyclic hydrocarbon group of R , R a02 , R a03 , R a04 , R a6 and R a7 is preferably 5 to 12, and more preferably 5 to 10. . The number of carbon atoms of the aromatic hydrocarbon group of R . The number of carbon atoms of the aromatic hydrocarbon group of R , R a02 and R a03 is preferably 6 to 12, and more preferably 6 to 10. . For the group combining an alkyl group and an alicyclic hydrocarbon group, it is preferable that the total number of carbon atoms of the combined alkyl group and alicyclic hydrocarbon group is 18 or less. . For the group combining an alkyl group and an aromatic hydrocarbon group, it is preferable that the total number of carbon atoms of the combined alkyl group and aromatic hydrocarbon group is 18 or less. R a02 and R a03is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, more preferably a methyl group, an ethyl group, a phenyl group or a naphthyl group which may have a halogen atom. R a04 is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom or an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a halogen atom, more preferably a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group which may have a halogen atom. R a6 and R a7 are preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkenyl group having 2 to 6 carbon atoms which may have a halogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, 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 which may have a halogen atom, still more preferably an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group or a phenyl group which may have a halogen atom. m1 is preferably any integer from 0 to 3, more preferably 0 or 1. n1 is preferably any integer from 0 to 3, more preferably 0 or 1. n1’ is preferably 0 or 1.

[0062] Examples of the structural unit (a1-0) include a structural unit represented by any of the formulas (a1-0-1) to (a1-0-24) and a structural unit in which the methyl group corresponding to R a01 in the structural unit (a1-0) is replaced by a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group, and a structural unit represented by any of the formulas (a1-0-1) to (a1-0-10), (a1-0-13), (a1-0-14), (a1-0-19) to (a1-0-24) is preferred. TIFF2025097318000063.tif120161

[0063] Examples of the structural unit (a1-1) include structural units derived from the monomers described in JP-A-2010-204646. Among them, the structural units represented by any of formulae (a1-1-1) to (a1-1-7) and the methyl group corresponding to R in the structural unit (a1-1) a4 is preferably a structural unit in which the methyl group is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group, and more preferably a structural unit represented by any of formulae (a1-1-1) to (a1-1-4). TIFF2025097318000064.tif34168

[0064] Examples of the structural unit (a1-2) include structural units represented by any of formulae (a1-2-1) to (a1-2-20) and the methyl group corresponding to R in the structural unit (a1-2) a5 is preferably a structural unit in which the methyl group is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group, and more preferably a structural unit represented by any of formula (a1-2-2), formula (a1-2-5), formula (a1-2-6) and formulae (a1-2-10) to (a1-2-20). TIFF2025097318000065.tif92163

[0065] When the resin (A) contains the structural unit (a1-0) and / or the structural unit (a1-1) and / or the structural unit (a1-2), the total content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Also, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is 10 to 95 mol%, preferably 15 to 90 mol%, more preferably 20 to 85 mol%, still more preferably 25 to 70 mol%, and even more preferably 30 to 70 mol%. When the resin (A) contains the structural unit (a1-0), the content thereof is 5 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more, still more preferably 20 mol% or more, even more preferably 25 mol% or more, still even more preferably 30 mol% or more, and even more preferably 35 mol% or more, based on all the structural units of the resin (A). Also, it is 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less, even more preferably 60 mol% or less. Specifically, it is 5 to 80 mol%, preferably 5 to 75 mol%, and more preferably 10 to 70 mol%. When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), the total content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Also, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is 10 to 90 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, still more preferably 20 to 80 mol%, even more preferably 20 to 75 mol%, and still even more preferably 20 to 70 mol%.

[0066] Examples of the structural unit having the group (2) in the structural unit (a1) include the structural unit represented by the formula (a1-4) (hereinafter sometimes referred to as "structural unit (a1-4)"). TIFF2025097318000066.tif31117[In the formula (a1-4), all the symbols have the same meanings as described above.]

[0067] R a1 and R a17 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R a01 include the same ones as those exemplified by the like of R of formula (a1-0). R a1 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 a17 Examples of the alkoxy group in R 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 an alkoxy group having 1 to 3 carbon atoms, even more preferably a methoxy group or an ethoxy group, and still more preferably a methoxy group. R a17 Examples of the alkoxyalkyl group in R 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 an alkoxyalkyl group having 2 to 4 carbon atoms, even more preferably a methoxymethyl group or an ethoxyethyl group, and still more preferably a methoxymethyl group. R a17 Examples of the alkoxyalkoxy group in R 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, more preferably an alkoxyalkoxy group having 2 to 4 carbon atoms, and even more preferably a methoxyethoxy group or an ethoxyethoxy group. R a17Examples of the alkylcarbonyl group in [context] include an acetyl group, a propionyl group, a butyryl group and the like. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 4 carbon atoms, more preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and even more preferably an acetyl group. R a17 Examples of the alkylcarbonyloxy group in [context] include an acetyloxy group, a propionyloxy group and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 4 carbon atoms, more preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and even more preferably an acetyloxy group. R a17 is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, 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.

[0068] A a11Examples of the alkanediyl group include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, and branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, heptane-1,6-diyl group, octane-1,7-diyl group, nonane-1,8-diyl group, decane-1,9-diyl group, undecane-1,10-diyl group. The number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 4, still even more preferably 1 to 3, and even more preferably 1 or 2. R a18 Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, and tert-butyl group. A a11 When -CH2- contained in the alkanediyl group of A is replaced by -O-, -CO- or -NR a18 -, the number of carbon atoms before replacement is defined as the number of carbon atoms of the alkanediyl group. A a11 Examples of the group in which -CH2- contained in the alkanediyl group of A is replaced by -O-, -CO- or -NR a18 - include hydroxy group, carboxy group, carbonyl group, oxy group, amino group (the group in which -CH2- contained in the methyl group is replaced by -NR a18 -), alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylamino group (the group in which any -CH2- contained in the alkyl group is replaced by -NR a18 -), peptide group (the group in which -CH2-CH2- contained in the ethylene group is replaced by -CO-NR a18-replaced group), an alkanediyl-oxy group, an alkanediyl-oxycarbonyl group, an alkanediyl-carbonyl group, an alkanediyl-carbonyl-oxy group, an alkanediyl-sulfonyl group, an alkanediyl-thio group, an alkanediyl-amino group (where any -CH2- at any position in the alkanediyl group is -NR a18 -replaced group), etc. are mentioned. These replaced groups include those similar to the examples shown in this specification within the range allowed by the upper limit of the number of carbon atoms. Examples of the alkylamino group include alkylamino groups having 1 to 11 carbon atoms, such as methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, octylamino group, etc. The number of carbon atoms of the alkylamino group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkanediylamino group include alkanediylamino groups having 1 to 11 carbon atoms, such as methyleneamino group, ethyleneamino group, propyleneamino group, etc. The number of carbon atoms of the alkanediylamino group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. For example, A a11 -replaced group where the -CH2- contained in the alkanediyl group of is -O-, -CO- or -NR a18 -include *-O-, *-CO-O-, *-O-CO-, *-CO-O-A a12 -CO-O-, *-O-CO-A a12 -O-, *-O-A a12 -CO-O-, *-CO-O-A a12 -O-CO-, *-O-CO-A a12 -O-CO-, *-CO-NR a18 -are mentioned. Among them, *-CO-O-, *-CO-O-A a12 -CO-O-, *-O-A a12 -CO-O-, *-CO-NR a18 -are preferred. Here, A a12 represents an alkanediyl group having 1 to 8 carbon atoms, and * is R a1represents the bonding site with the carbon atom to which it is attached. A a12 The alkandiyl group of a11 includes the same alkandiyl groups as A within the range permitted by the upper limit of the number of carbon atoms. A a11 is preferably a single bond, *-CO-O- or *-CO-O-A a12 -CO-O-, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-. na1 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. na11 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. mc is preferably 0 or 1.

[0069] 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 combining these. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, etc. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following group (* represents the bonding site.). Examples of the combined group include a group formed by combining the above-described alkyl group and alicyclic hydrocarbon group (e.g., alkylcycloalkyl groups or cycloalkylalkyl groups such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornil group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having an alkyl group (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), aromatic hydrocarbon groups having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), aryl-cycloalkyl groups such as phenylcyclohexyl group, etc. In particular, R a36 Examples of R 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. R a35 and R a36 Examples of the divalent hydrocarbon group having 2 to 20 carbon atoms formed by R and R bonding to each other together with the -C-O- to which they are bonded include, for example, the following groups. * represents a bonding site, and one side is the bonding site with R a34 and the other side is the bonding site with R. TIFF2025097318000068.tif15105

[0070] 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 of 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 groups, 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. R a36The alkyl group and alicyclic hydrocarbon group in [it] are preferably unsubstituted. R a36 The aromatic hydrocarbon group in [it] preferably has an aromatic ring having an aryloxy group with 6 to 10 carbon atoms.

[0071] -O-C(R a34 )(R a35 )-O-R a36 in the structural unit (a1-4) eliminates upon contact with an acid (for example, p-toluenesulfonic acid) to form a hydroxy group or a carboxy group. -X a1 -O-C(R a34 )(R a35 )-O-R a36 in the case of a benzene ring, may be bonded to any of the o-position, m-position, or p-position with respect to the bonding position of A a11 . Among them, it is preferable that at least one is bonded to the o-position or p-position, and more preferably bonded to the p-position. In the case of a naphthalene ring, when the bonding position of A a11 is at the 1-position, it may be bonded to any of the 2nd to 8th positions, and when the bonding position of A a11 is at the 2nd position, it may be bonded to any of the 1st and 3rd to 8th positions. Among them, when the bonding position of A a11 is at the 1-position, it is preferable that at least one is bonded to the 3rd to 6th positions, and more preferably bonded to the 3rd or 4th position. When the bonding position of A a11 is at the 2nd position, it is preferable that it is bonded to the 4th to 7th positions, and more preferably bonded to the 5th or 6th position.

[0072] Examples of the structural unit (a1-4) include structural units derived from the monomers described in JP-A-2010-204646. Preferably, the structural units represented by the formulas (a1-4-1) to (a1-4-42) and R in the structural unit (a1-4) a1Examples of the structural unit in which the hydrogen atom corresponding to is replaced with a halogen atom, a haloalkyl group, or an alkyl group include, more preferably, the structural units represented by formula (a1-4-1) to formula (a1-4-5), formula (a1-4-10), formula (a1-4-13), formula (a1-4-14), formula (a1-4-19), and formula (a1-4-20). TIFF2025097318000069.tif228165

[0073] When the resin (A) contains the structural unit (a1-4), the content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on the total of all the structural units of the resin (A). Further, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is 5 to 95 mol%, preferably 10 to 95 mol%, more preferably 15 to 90 mol%, still more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.

[0074] Examples of the structural unit derived from the (meth)acrylic monomer having the group (2) also include the structural unit represented by formula (a1-5) (hereinafter sometimes referred to as "structural unit (a1-5)"). TIFF2025097318000070.tif4558[In formula (a1-5), all the symbols have the same meanings as described above.]

[0075] R a8 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in are the same as those exemplified for R in formula (a1-0). a01 The same ones as those exemplified above can be mentioned. 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 them, it is preferable that one is -O- and the other is -S-. s1 is preferably 1. s1' is preferably any integer from 0 to 2. Z a1 is preferably a single bond or *-CH2-CO-O-.

[0076] Examples of the structural unit (a1-5) include structural units derived from the monomers described in JP-A-2010-61117. Among them, the structural units represented by formulas (a1-5-1) to (a1-5-4) are preferable, and the structural unit represented by formula (a1-5-1) or formula (a1-5-2) is more preferable. When the resin (A) contains the structural unit (a1-5), its content is 1 mol% or more, preferably 2 mol% or more, more preferably 3 mol% or more, still more preferably 5 mol% or more, even more preferably 10 mol% or more, still even more preferably 20 mol% or more, and even more preferably 25 mol% or more, based on all the structural units of the resin (A). Also, it is 80 mol% or less, preferably 70 mol% or less, more preferably 60 mol% or less, still more preferably 50 mol% or less, even more preferably 45 mol% or less, still even more preferably 40 mol% or less, and even more preferably 30 mol% or less. Specifically, 1 to 50 mol% is preferable, 3 to 45 mol% is more preferable, 5 to 40 mol% is still more preferable, and 5 to 30 mol% is even more preferable.

[0077] Examples of the structural unit having the group (1) in the structural unit (a1) include the structural unit represented by formula (a1-6) (hereinafter sometimes referred to as "structural unit (a1-6)"). TIFF2025097318000072.tif3481 [In formula (a1-6), all symbols have the same meaning as defined above.]

[0078] R a61 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in the formula (a1-0) include R a01 The same examples as those exemplified above are included. R a61 is preferably a hydrogen atom, a methyl group, or a trifluoromethyl group. R a62 , R a63 , R a64 and R a65 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, etc. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and further preferably a methyl group or an ethyl group. R a62 , R a63 and R a64 The cyclic hydrocarbon group in the formula (I) includes an alicyclic hydrocarbon group and an aromatic hydrocarbon group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, and a norbornyl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16, and more preferably 3 to 12. Examples of the aromatic hydrocarbon group include a phenylene group and a naphthylene group. Examples of the substituent that the cyclic hydrocarbon group may have include 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. Ra62 and R a63 Examples of the ring formed by the combination of R a62 and R a63 include an adamantane ring, a cyclopentane ring, a cyclohexane ring, and the like. Specifically, when R a62 and R a63 are combined with each other to form a ring, examples of -C(R a64 )(R TIFF2025097318000073.tif32110

[0079] L a61 and L a62 Examples of the C1-C4 alkanediyl group in 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 butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, and the like. L a61 and L a62 are each independently preferably a methylene group or an ethylene group. X a61 is preferably a single bond or -CO-O-*, and more preferably a single bond. X a62 is preferably a single bond or *-O-L a61 -, and more preferably a single bond.

[0080] Examples of the C6-C20 aromatic hydrocarbon group of Ar include a phenylene group, a 1-naphthylene group, a 2-naphthylene group, a 1-anthrylene group, a 9-anthrylene group, a biphenylene group, a 1-phenanthrylene group, and a 2-phenanthrylene group. Examples of the substituent that the aromatic hydrocarbon group may have include 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.

[0081] Examples of the halogen atom include a fluorine atom, an iodine 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 alkyl group preferably has 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. 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, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. The alkoxy group preferably has 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 preferably has 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 preferably has 2 to 8 carbon atoms, 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. Preferred substituents include 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 preferred are 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. Even more preferred are a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group. Ar is preferably a phenylene group which may have a substituent, and more preferably a phenylene group which may have a hydroxy group.

[0082] Examples of the structural unit (a1-6) include structural units represented by Formula (a1-6-1) to Formula (a1-6-44). Structural units represented by Formula (a1-6-1) to Formula (a1-6-9) are preferred, structural units represented by Formula (a1-6-1), Formula (a1-6-2), Formula (a1-6-4), Formula (a1-6-5), Formula (a1-6-7), or Formula (a1-6-8) are more preferred, and structural units represented by Formula (a1-6-1) or Formula (a1-6-2) are even more preferred. TIFF2025097318000074.tif227165

[0083] In the structural units represented by Formula (a1-6-1) to Formula (a1-6-9), Formula (a1-6-16) to Formula (a1-6-21), Formula (a1-6-28) to Formula (a1-6-30), and Formula (a1-6-37) to Formula (a1-6-44), R a61A structural unit in which a hydrogen atom corresponding to is replaced with a methyl group, a halogen atom, a haloalkyl group, etc., and in the structural units represented by formula (a1-6-10) to formula (a1-6-15), formula (a1-6-22) to formula (a1-6-27), and formula (a1-6-31) to formula (a1-6-36), R a61 A structural unit in which a methyl group corresponding to a61 is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, etc. is also cited as the structural unit (a1-6).

[0084] When the resin (A) contains the structural unit (a1-6), the content thereof is 3 mol% or more, preferably 5 mol% or more, more preferably 7 mol% or more, still more preferably 10 mol% or more, even more preferably 20 mol% or more, still even more preferably 30 mol% or more, and even more preferably 40 mol% or more, based on all the structural units of the resin (A). Also, 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, still more preferably 7 to 70 mol%, even more preferably 7 to 65 mol%, and particularly preferably 10 to 65 mol%.

[0085] Also, as the structural unit (a1), the following structural units are also cited. TIFF2025097318000075.tif33167

[0086] When the resin (A) contains structural units represented by the formulas (a1-7-1) to (a1-7-7), the content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, yet even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Further, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, yet even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, 10 to 95 mol% is preferable, 15 to 90 mol% is more preferable, 20 to 85 mol% is still more preferable, 20 to 70 mol% is even more preferable, and 20 to 60 mol% is particularly preferable.

[0087] In addition, examples of the structural unit (a1) also include the following structural units. TIFF2025097318000076.tif51120 When the resin (A) contains structural units represented by the formulas (a1-8-1) to (a1-8-3), the content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, yet even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Further, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, yet even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, 10 to 60 mol% is preferable, 15 to 55 mol% is more preferable, 20 to 50 mol% is still more preferable, 20 to 45 mol% is even more preferable, and 20 to 40 mol% is particularly preferable.

[0088] 〈Structural unit (s)〉 The structural unit(s) is / are derived from monomers having no acid-labile group (hereinafter sometimes referred to as "monomer(s)"). As the monomer(s) from which the structural unit(s) is / are derived, monomers having no acid-labile group known in the resist field can be used. The structural unit(s) preferably has a hydroxy group, a carboxy group or a lactone ring. By using a resin containing a structural unit having a hydroxy group or a carboxy group and no acid-labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and no acid-labile group (hereinafter sometimes referred to as "structural unit (a3)") in the resist composition of the present invention, the resolution of the resist pattern and the adhesion to the substrate can be improved. In addition to the above-described structural units, the structural unit(s) includes a structural unit having a halogen atom (hereinafter sometimes referred to as "structural unit (a4)"), a structural unit having a non-leaving hydrocarbon group (hereinafter sometimes referred to as "structural unit (a5)"), a structural unit having a sultone structure (hereinafter sometimes referred to as "structural unit (a6)"), or a structural unit that decomposes upon exposure to generate an acid (hereinafter sometimes referred to as "structural unit (a7)"), and the like.

[0089] 〈Structural unit (a2)〉 The structural unit (a2) is a structural unit represented by the formula (a2) and has an alcoholic hydroxy group, a phenolic hydroxy group or a carboxy group. TIFF2025097318000077.tif4194[In the formula (a2), R a2 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a28 -. R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L a21represents a single bond or a hydrocarbon group having 1 to 28 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-. L a22 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-. na2 represents any integer from 1 to 5. When na2 is any integer of 2 or more, a plurality of Ls a22 may be the same as or different from each other.

[0090] R a2 Examples of the halogen atom in R include a fluorine atom, an iodine atom, a chlorine atom, a bromine atom and the like. R a2 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group. The number of carbon atoms of the alkyl group is preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 or 2. R a2 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 still more preferably a hydrogen atom or a methyl group.

[0091] A a21Examples of the alkanediyl group include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, etc., and branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, heptane-1,6-diyl group, octane-1,7-diyl group, nonane-1,8-diyl group, decane-1,9-diyl group, undecane-1,10-diyl group, etc. The number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 4, still even more preferably 1 to 3, and even more preferably 1 or 2. R a28 Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, and tert-butyl group. A a21 When -CH2- contained in the alkanediyl group of A is replaced by -O-, -CO- or -NR a28 -, the number of carbon atoms before replacement is defined as the number of carbon atoms of the alkanediyl group. A a21 Examples of the group in which -CH2- contained in the alkanediyl group of A is replaced by -O-, -CO- or -NR a28 - include hydroxy group, carboxy group, carbonyl group, oxy group, amino group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylamino group, peptide group, alkanediyl-oxy group, alkanediyl-oxycarbonyl group, alkanediyl-carbonyl group, alkanediyl-carbonyl-oxy group, alkanediyl-sulfonyl group, alkanediyl-thio group, alkanediyl-amino group, etc. These replaced groups include those similar to those exemplified in this specification as long as the upper limit of the number of carbon atoms permits. For example, A a21 In the alkanediyl group of, the -CH2- contained in it is replaced by -O-, -CO- or -NR a28 The groups replaced by - are *-O-, *-CO-O-, *-O-CO-, *-CO-O-A a22 -CO-O-, *-O-CO-A a22 -O-, *-O-A a22 -CO-O-, *-CO-O-A a22 -O-CO-, *-O-CO-A a22 -O-CO-, *-CO-NR a28 - are included. Among them, *-CO-O-, *-CO-O-A a22 -CO-O-, *-O-A a22 -CO-O-, *-CO-NR a28 - are preferred. Here, A a22 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents the bonding site with the carbon atom to which R a2 is bonded. The alkanediyl group of A a22 is, within the range allowed by the upper limit of the number of carbon atoms, an alkanediyl group similar to A a21 is included. A a21 is preferably a single bond, *-CO-O- or *-CO-O-A a22 -CO-O-, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-.

[0092] L a21 The hydrocarbon group in is a (na2 + 1)-valent hydrocarbon group, and examples include linear or branched chain hydrocarbon groups, monocyclic or polycyclic (including spiro rings, condensed rings, bridged rings, etc.) alicyclic hydrocarbon groups, and cyclic hydrocarbon groups such as aromatic hydrocarbon groups. A group formed by combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group) may also be used. L a21 Examples of the chain hydrocarbon group of include divalent to hexavalent chain hydrocarbon groups such as alkanediyl groups, alkanetriyl groups, alkanetetrayl groups, alkanepentayl groups, and alkanexayl groups. Examples of the alkanediyl group include, for example, A a21 and the same alkanediyl groups as those described above. Examples of the alkanetriyl group include a methanetriyl group, an ethanetriyl group, a propanetriyl group, a butanetriyl group, a pentanetriyl group, a hexanetriyl group, a heptanetriyl group, an octanetriyl group, a nonanetriyl group, a decanetriyl group, an undecanetriyl group, a dodecanetriyl group, a tridecanetriyl group, a tetradecanetriyl group, a pentadecanetriyl group, a hexadecanetriyl group, a heptadecanetriyl group, and the like. Examples of the alkanetetrayl group include a methanetetrayl group, an ethanetetrayl group, a propanetetrayl group, a butanetetrayl group, a pentanetetrayl group, a hexanetetrayl group, a heptanetetrayl group, an octanetetrayl group, a nonanetetrayl group, a decanetetrayl group, an undecanetetrayl group, a dodecanetetrayl group, a tridecanetetrayl group, a tetradecanetetrayl group, a pentadecanetetrayl group, a hexadecanetetrayl group, a heptadecanetetrayl group, and the like. Examples of the alkanepentayl group include a methanepentayl group, an ethanepentayl group, a propanepentayl group, a butanepentayl group, a pentanepentayl group, a hexanepentayl group, and the like. Examples also include groups in which one or more hydrogen atoms of the above-described groups are replaced with a bonding site, and the like. The number of carbon atoms in the chain hydrocarbon group is preferably from 1 to 18, more preferably from 1 to 12, still more preferably from 1 to 10, even more preferably from 1 to 9, still even more preferably from 1 to 8, still more preferably from 1 to 6, still even more preferably from 1 to 5, and particularly preferably from 1 to 4. L a21 Examples of the monocyclic and polycyclic alicyclic hydrocarbon groups in TIFF2025097318000078.tif46168For example, divalent to hexavalent alicyclic hydrocarbon groups such as cycloalkanediyl groups, cycloalkanetriyl groups, cycloalkanetetrayl groups, cycloalkanepentayl groups, cycloalkanhexayl groups, etc. can be mentioned. Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, cyclopropanetriyl group, cyclobutanetriyl group, cyclopentanetriyl group, cyclohexanetriyl group, cycloheptanetriyl group, cyclooctanetriyl group, cyclodecanetriyl group, cyclopropanetetrayl group, cyclobutanetetrayl group, cyclopentanetetrayl group, cyclohexanetetrayl group, cycloheptanetetrayl group, cyclooctanetetrayl group, cyclodecanetetrayl group and polycyclic alicyclic hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, decahydronaphthalenediyl group, bicyclo[3.3.0]octanediy group, norbornanetriyl group, adamantanetriyl group, decahydronaphthalenetriyl group, bicyclo[3.3.0]octanetriyl group, norbornanetetrayl group, adamantanetetrayl group, decahydronaphthalenetetrayl group, bicyclo[3.3.0]octanetetrayl group can be mentioned. Moreover, groups in which one or more hydrogen atoms of the above-mentioned groups are replaced by bonding sites, etc. can also be mentioned. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 18, still more preferably 3 to 16, even more preferably 3 to 12, still even more preferably 6 to 12, and particularly preferably 6 to 10. L a21 As the aromatic hydrocarbon group in, divalent to hexavalent aromatic hydrocarbon groups such as arylene groups, arenetriyl groups, arenetetrayl groups, arenepentayl groups, arenhexayl groups, etc. can be mentioned. Specifically, examples include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, a benzenetriyl group, a naphthalenetriyl group, an anthracenetriyl group, a biphenylenetriyl group, a phenanthrenetriyl group, a benzenetetrayl group, a naphthalenetetrayl group, an anthracenetetrayl group, a biphenylenetetrayl group, a phenanthrenetetrayl group, and the like. Also included are groups in which one or more hydrogen atoms of the above-described groups are replaced with bonding sites, and the like. The number of carbon atoms in the aromatic hydrocarbon group is preferably from 6 to 20, more preferably from 6 to 18, still more preferably from 6 to 14, even more preferably from 6 to 12, and even more preferably from 6 to 10. Examples of the group formed by combining two or more types include a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group, a group formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group, a group formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, a group formed by combining an alicyclic hydrocarbon group, a chain hydrocarbon group, and an aromatic hydrocarbon group, and the like. In the combination, the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and the chain hydrocarbon group may each be combined with two or more types. Also, any group may be bonded to A a21 and L a22 and may be bonded thereto. Examples of groups in which -CH2- contained in a hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include a hydroxy group (a group in which -CH2- contained in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH2- contained in a methyl group is replaced by -S-), an alkoxy group (a group in which -CH2- at any position contained in an alkyl group is replaced by -O-), an alkylthio group (a group in which -CH2- at any position contained in an alkyl group is replaced by -S-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in an alkyl group is replaced by -O-CO-), an alkylsulfonyl group (a group in which -CH2- at any position contained in an alkyl group is replaced by -SO2-), an alkylcarbonyl group (a group in which -CH2- at any position contained in an alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in an alkyl group is replaced by -CO-O-), an oxy group (a group in which -CH2- contained in a methylene group is replaced by -O-), a carbonyl group (a group in which -CH2- contained in a methylene group is replaced by -CO-), a thio group (a group in which -CH2- contained in a methylene group is replaced by -S-), a sulfonyl group (a group in which -CH2- contained in a methylene group is replaced by -SO2-), an alkanedioxy group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -O-), an alkanedioxycarbonyl group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced by -O-CO-), an alkanediylcarbonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced by -CO-O-), an alkanediylsulfonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -SO2-), an alkanediylthio group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -S-), a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group,Examples include an aromatic hydrocarbon group-carbonyl oxy 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. Also included are groups in which one or more hydrogen atoms of these groups are replaced at the bonding site. These replaced groups include those similar to the groups exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms.

[0093] Examples of groups in which -CH2- contained in an alicyclic hydrocarbon group and a group formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- include those similar to the groups exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms. L a21 The hydrocarbon group in L may have one or more substituents. Examples of the substituent include a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, an alkyl group having 1 to 16 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-), an acryloyloxy group or a methacryloyloxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. L a21 By having a halogen atom as a substituent, the hydrocarbon group in L can substantially have a substituent such as a haloalkyl group. Examples of the haloalkyl group include an alkyl fluoride group, an alkyl chloride group, an alkyl bromide group, an alkyl iodide group, etc., such as a chloromethyl group, a bromomethyl group, an iodomethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, etc. The number of carbon atoms of the haloalkyl group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. L a21 The hydrocarbon group of L includes a branched structure, whereby L a21can substantially have substituents such as an alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 10, still more preferably 1 to 8, even more preferably 1 to 6, yet even more preferably 1 to 4, and still even more preferably 1 to 3. L a21 is substantially a group in which -CH2- contained in the hydrocarbon group is replaced by a group such as -O- or -CO-, a21 can substantially have substituents such as a hydroxy group, a carboxy group, an alkoxy group, a thiol group, a sulfonyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxyalkyl group, an alkoxyalkoxy group, an acryloyloxy group, and a methacryloyloxy group. The number of carbon atoms in the alkoxy group is preferably 1 to 12, more preferably 1 to 6, still more preferably 1 to 4, and still even more preferably 1 to 3. The number of carbon atoms in the alkoxycarbonyl group, the alkylcarbonyl group, and the alkylcarbonyloxy group is preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and still even more preferably 2 to 3. The number of carbon atoms in the alkoxyalkyl group and the alkoxyalkoxy group is preferably 2 to 12, more preferably 2 to 8, still more preferably 2 to 6, and still even more preferably 2 to 4. These groups include those similar to those exemplified in this specification. L a21Examples of the substituent that the hydrocarbon group in [compound name] may have include a halogen atom, a haloalkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 12 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-). A halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 10 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-) is more preferred. A halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms is even more preferred. A fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxy methoxy group is still more preferred. A fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, a methoxy group, or an ethoxyethoxy group is yet still more preferred. Also, when a21 the alkanediyl group of L a23 is replaced by -O- or -CO- etc., for example, *-L a21 -X a23 wherein L represents an alkanediyl group having 1 to 8 carbon atoms, and X a21 represents -O-, -O-CO-, -CO-O-, or -O-CO-O-, and * represents the bonding site with A a21 .) is also preferred. L a21is preferably a group formed by combining a single bond, an optionally substituted chain hydrocarbon group having 1 to 12 carbon atoms (provided that -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an optionally substituted cyclic hydrocarbon group having 3 to 20 carbon atoms (provided that -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), or an optionally substituted chain hydrocarbon group having 1 to 8 carbon atoms and an optionally substituted cyclic hydrocarbon group having 3 to 20 carbon atoms (provided that -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-); more preferably, it is a group formed by combining an optionally substituted chain hydrocarbon group having 1 to 10 carbon atoms (provided that -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an optionally substituted cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), or an optionally substituted chain hydrocarbon group having 1 to 6 carbon atoms and an optionally substituted cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-).

[0094] L a22Examples of the chain hydrocarbon group having 1 to 12 carbon atoms include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, etc., and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, 1-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-dimethylpropane-1,3-diyl group, pentane-2,4-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, etc. The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6, and even more preferably 1 to 4. Examples of the group in which -CH2- contained in the chain hydrocarbon group is replaced by -O- or -CO- include those similar to those exemplified herein within the range allowed by the upper limit of the number of carbon atoms. L a22 The fluorine atom(s) that L has may be one or two or more. na2 is preferably any integer from 1 to 4, and more preferably any integer from 1 to 3. L a21 Examples of the structural unit (a2) when L is a single bond or a chain hydrocarbon group include, for example, the following structural units. Among the following structural units, the methyl group corresponding to R a2 replaced by a hydrogen atom or the like is also a preferred structural unit of the structural unit (a2) in the same manner as the following structural units. TIFF2025097318000079.tif67163

[0095] When producing a resist pattern from the resist composition of the present invention, when using a high-energy ray such as a KrF excimer laser (248 nm), an electron beam, or EUV (extreme ultraviolet light) as an exposure light source, as the structural unit (a2), a structural unit (a2) having a phenolic hydroxy group is preferable, and it is more preferable to use the structural unit (a2-A) described later. When using an ArF excimer laser (193 nm) or the like, as the structural unit (a2), a structural unit (a2) having an alcoholic hydroxy group is preferable, and it is more preferable to use the structural unit (a2-C) described later. The structural unit (a2) may contain one kind alone or two or more kinds.

[0096] In the structural unit (a2), L a21 When it is a cyclic hydrocarbon group, examples of the structural unit having a phenolic hydroxy group or a carboxy group include a structural unit represented by the formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A)"). TIFF2025097318000080.tif30128[In the formula (a2-A), all the symbols have the same meanings as described above.] R a2 and A a21 are each a group similar to those exemplified in the formula (a2). R a27 Examples of the halogen atom of R include a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom. R a27Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include trifluoromethyl group, difluoromethyl group, methyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, ethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, butyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, pentyl group, hexyl group, perfluorohexyl group, chloromethyl group, bromomethyl group, iodomethyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a27 Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group, tert-butoxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, still more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. R a27 Examples of the alkoxyalkyl group include methoxymethyl group, ethoxyethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxymethyl group, tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably an alkoxyalkyl group having 2 to 4 carbon atoms, still more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group. R a27Examples 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, more preferably an alkoxyalkoxy group having 2 to 4 carbon atoms, and even more preferably a methoxyethoxy group or an ethoxyethoxy group. R a27 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 4 carbon atoms, more preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and even more preferably an acetyl group. R a27 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 4 carbon atoms, more preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and even more preferably an acetyloxy group. R a27 is preferably a halogen atom, a hydroxy group, a carboxy group, an optionally halogenated 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. nA2 is preferably 1, 2, 3, or 4, more preferably 1, 2, or 3, and even more preferably 1 or 2. na21 is preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, and even more preferably 0 or 1. mc is preferably 0 or 1. -X a2 -OH, in the case of a benzene ring, A a21It may be bonded to any of the o-position, m-position or p-position with respect to the bonding position. Among them, at least one is preferably bonded to the m-position or p-position, and more preferably bonded to the m-position. In the case of a naphthalene ring, A a21 When the bonding position of A a21 is the 1-position, it may be bonded to any of the 2-position to 8-position, and A a21 When the bonding position of A a21 is the 2-position, it is preferably bonded to the 4-position to 7-position, and more preferably bonded to the 5-position or 6-position.

[0097] Examples of the structural unit (a2-A) include structural units derived from monomers described in JP-A-2010-204634 and JP-A-2012-12577. Examples of the structural unit (a2-A) include structural units represented by formula (a2-2-1) to formula (a2-2-32), formula (a2-3-1) to formula (a2-3-24), and in the structural units represented by formula (a2-2-1) to formula (a2-2-32), formula (a2-3-1) to formula (a2-3-24), the methyl group corresponding to R a2 in the structural unit (a2-A) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group. TIFF2025097318000081.tif107170

[0098] When the structural unit (a2-A) is included in the resin (A), the content of the structural unit (a2-A) is preferably 5 mol% or more, more preferably 10 mol% or more, still more preferably 15 mol% or more, and even more preferably 20 mol% or more, based on all the structural units. Also, it is preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less, even more preferably 60 mol% or less, still even more preferably 50 mol% or less, still more preferably 45 mol% or less, and even more preferably 40 mol% or less. Specifically, it is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, still more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%. The structural unit (a2-A) can be incorporated into the resin (A) by polymerizing a compound that induces the structural unit (a2-A) (for example, a compound (a2-A') in which the -CH2-C(-R a2 )- of the structural unit (a2-A) is in the state of CH2=C(-R a2 ) before cleavage). Further, for example, after polymerization using the structural unit (a1-4), it can be incorporated into the resin (A) by treatment with an acid such as p-toluenesulfonic acid. Also, after polymerization using acetoxystyrene or the like, the structural unit (a2-A) can be incorporated into the resin (A) by treatment with an alkali such as tetramethylammonium hydroxide.

[0099] In the structural unit (a2), when L a21 is a cyclic hydrocarbon group, examples of the structural unit having an alcoholic hydroxy group or a carboxy group include the structural unit represented by formula (a2-B) (hereinafter sometimes referred to as "structural unit (a2-B)"), the structural unit represented by formula (a2-C) (hereinafter sometimes referred to as "structural unit (a2-C)"), or the structural unit represented by formula (a2-D) (hereinafter sometimes referred to as "structural unit (a2-D)"). In formulas (a2-B) and (a2-C), R a2 represents the same meaning as in formula (a2). R a27 represents the same meaning as in formula (a2-A). L a25 represents -O- or *-O-(CH2) k2 -CO-O-, k2 represents any integer from 1 to 7. * represents the bonding site with -CO-. X a2 represents a single bond or -CO-. R a25 and R a26 each independently represent a hydrogen atom, a methyl group, or a hydroxy group. nB2 represents any integer from 1 to 5. When nB2 is 2 or more, the plurality of X a2 may be the same as or different from each other. nB22 represents any integer from 0 to 8. When nB22 is 2 or more, the plurality of R a27 may be the same as or different from each other. nC22 represents any integer from 0 to 10. When nC22 is 2 or more, the plurality of R a27 may be the same as or different from each other.] L a25 is preferably -O-, -O-(CH2) f1 -CO-O- (where f1 represents any integer from 1 to 4), more preferably -O-. R a2 is preferably a methyl group. X a2 is preferably a single bond. R a25 is preferably a hydrogen atom. R a26 is preferably a hydrogen atom or a hydroxy group. R a27is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, 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 ethoxy methoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group or an ethoxyethoxy group. nB2 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. nB22 is preferably any integer from 0 to 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. nC22 is preferably any integer from 0 to 6, more preferably any integer from 0 to 3, and even more preferably 0 or 1.

[0100] Examples of the structural unit (a2-B) and the structural unit (a2-C) include structural units derived from the monomers described in JP-A-2010-204646, the following structural units, and methyl groups or hydrogen atoms corresponding to R in the following structural units replaced with hydrogen atoms, halogen atoms, haloalkyl groups or other alkyl groups. Among them, the structural units represented by any of formula (a2-B-1) to formula (a2-B-5) and formula (a2-C-1) to formula (a2-C-9) are preferable. a2 When the resin (A) contains the structural unit (a2-B) or the structural unit (a2-C), the content thereof is 1 mol% or more, preferably 2 mol% or more, based on all the structural units of the resin (A). Further, it is 45 mol% or less, preferably 40 mol% or less, more preferably 35 mol% or less, even more preferably 20 mol% or less, and still more preferably 10 mol% or less. Specifically, 1 to 45 mol% is mentioned, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, even more preferably 1 to 20 mol%, and still more preferably 1 to 10 mol%. TIFF2025097318000084.tif80164 When the resin (A) contains the structural unit (a2-B) or the structural unit (a2-C), the content thereof is 1 mol% or more, preferably 2 mol% or more, based on all the structural units of the resin (A). Further, it is 45 mol% or less, preferably 40 mol% or less, more preferably 35 mol% or less, even more preferably 20 mol% or less, and still more preferably 10 mol% or less. Specifically, 1 to 45 mol% is mentioned, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, even more preferably 1 to 20 mol%, and still more preferably 1 to 10 mol%.

[0101] TIFF2025097318000085.tif51106[in formula (a2-D), R a2 and A a21 each represent the same meaning as in formula (a2). R a27 represents the same meaning as in formula (a2-A). R a21 and R a22 each independently represent an alkyl fluoride group having 1 to 4 carbon atoms. L a24 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. nD2 represents any integer from 1 to 5. When nD2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. nD22 represents any integer from 0 to 4. When nD22 is 2 or more, the plurality of R a27 may be the same as or different from each other. However, 1 ≦ nD2 + nD22 ≦ 5.] R a21 and R a22 As the alkyl fluoride groups having 1 to 4 carbon atoms of R R a21 and R a22 each independently include a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, etc. L a24 As the alkanediyl group of L L a24 is preferably a single bond or a methylene group. R a27is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, 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 ethoxy methoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group or an ethoxyethoxy group. nD2 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, even more preferably 1 or 2, and even more preferably 1. Further, preferably, nD2 is 1 and the group in parentheses is bonded to the para position. nD22 is preferably any integer from 0 to 3, more preferably any integer from 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0102] As the structural unit (a2-D), a structural unit represented by the following formula (a2-D1) (hereinafter sometimes referred to as "structural unit (a2-D1)") is more preferable. TIFF2025097318000086.tif51108[In formula (a2-D1), R a2 、A a21 、R a27 、nD2 and nD22 represent the same meanings as in formula (a2-D).] In formula (a2-D1), R a2 is preferably a hydrogen atom or a methyl group. A a21 is preferably a single bond.

[0103] Examples of the structural unit (a2-D) include the structural units described below. TIFF2025097318000087.tif62167

[0104] In the structural units represented by formula (a2-D-1) to formula (a2-D-8), R a2In the structural units represented by formulae (a2-D-9) to (a2-D-16), the hydrogen atom corresponding to R a2 Specific examples of the structural unit (a2-D) include structural units in which the methyl group corresponding to the following formula is replaced with a hydrogen atom, etc. Among these, the structural units represented by formulae (a2-D-1) to (a2-D-8) are preferred, the structural units represented by formulae (a2-D-1) to (a2-D-4) are more preferred, and the structural unit represented by formula (a2-D-1) is even more preferred.

[0105] When the resin (A) contains the structural unit (a2-D), the content thereof is preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, based on the total structural units of the resin (A). Also, it is preferably 80 mol% or less, more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, even more preferably 10 to 70 mol%, and even more preferably 10 to 65 mol%.

[0106] <Structural unit (a3)> The lactone ring of the structural unit (a3) ​​may be a monocyclic ring such as a β-propiolactone ring, a γ-butyrolactone ring, or a δ-valerolactone ring, or may be a condensed ring of a monocyclic lactone ring and 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)). The structural unit (a3) ​​is preferably a structural unit represented by formula (a3-1), (a3-2), (a3-3) or (a3-4). One of these may be contained alone, or two or more of them may be contained. TIFF2025097318000088.tif51164 [In formula (a3-1), formula (a3-2), formula (a3-3) and formula (a3-4), L a4 , L a5 and L a6Each independently represents a group represented by -O- or *-O-(CH2) k3 -CO-O- (where k3 represents an integer from 1 to 7). L a7 represents -O-, *-O-L a8 -O-, *-O-L a8 -CO-O-, *-O-L a8 -CO-O-L a9 -CO-O- or *-O-L a8 -O-CO-L a9 -O-. L a8 and L a9 each independently represents an alkanediyl group having 1 to 6 carbon atoms. * represents the bonding site with the carbonyl group. R a18 , R a19 , R a20 and R a24 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X a3 represents -CH2- or an oxygen atom. R a21 represents an aliphatic hydrocarbon group having 1 to 4 carbon atoms. R a22 , R a23 and R a25 each independently represents a carboxy group, a cyano group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms. p1 represents an integer from 0 to 5. q1 represents an integer from 0 to 3. r1 represents an integer from 0 to 3. w1 represents an integer from 0 to 8. When p1, q1, r1, and / or w1 is 2 or more, the plurality of R a21 , R a22 , R a23 and / or R a25 may be the same as or different from each other.]

[0107] R a21 , R a22 , Ra23 and R a25 Examples of the aliphatic hydrocarbon group in and R include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group and tert-butyl group. R a18 、R a19 、R a20 and R a24 Examples of the halogen atom and the alkyl group which may have a halogen atom in and R include the same ones as those exemplified by R of formula (a1-0). a01 and the like. L a8 and L a9 Examples of the alkanediyl group in and L include methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group and 2-methylbutane-1,4-diyl group and the like. L a4 ~L a6 are each independently preferably -O- or, *-O-(CH2) k3 -CO-O- wherein k3 is an integer of any one of 1 to 4, more preferably -O- and, *-O-CH2-CO-O-, still more preferably an oxygen atom. L a7 is preferably -O- or *-O-L a8 -CO-O-, more preferably -O-, -O-CH2-CO-O- or -O-C2H4-CO-O-. R a18 、R a19 、R a20 and R a24 are preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, still more preferably a hydrogen atom or a methyl group. R a21 is preferably a methyl group. R a22 、R a23 and Ra25 Each is independently preferably a carboxy group, a cyano group or a methyl group. p1, q1 and r1 are each independently preferably any integer from 0 to 2, more preferably 0 or 1. w1 is preferably any integer from 0 to 2, more preferably 0 or 1. In particular, formula (a3-4) is preferably formula (a3-4)'. TIFF2025097318000089.tif4051 (wherein R a24 , L a7 represents the same meaning as above.)

[0108] Examples of the structural unit (a3) include structural units derived from the monomers described in JP-A-2010-204646, the monomers described in JP-A-2000-122294, and the monomers described in JP-A-2012-41274. Examples of the structural unit (a3) include structural units represented by any of formula (a3-1-1), formula (a3-1-2), formula (a3-2-1), formula (a3-2-2), formula (a3-3-1), formula (a3-3-2), and formula (a3-4-1) to formula (a3-4-12), and, in the above structural units, structural units in which the methyl groups corresponding to R a18 , R a19 , R a20 and R a24 are replaced by hydrogen atoms are preferred. When the resin (A) contains the structural unit (a3), the total content is 1 mol% or more, preferably 3 mol% or more, more preferably 5 mol% or more, and still more preferably 10 mol% or more based on all the structural units of the resin (A). Further, it is 70 mol% or less, preferably 65 mol% or less, more preferably 60 mol% or less, still more preferably 50 mol% or less, even more preferably 40 mol% or less, still even more preferably 30 mol% or less, still more preferably 25 mol% or less, and still even more preferably 20 mol% or less. Specifically, it is 1 to 70 mol%, preferably 3 to 70 mol%, more preferably 3 to 65 mol%, still more preferably 5 to 65 mol%, even more preferably 5 to 60 mol%, and still even more preferably 10 to 60 mol%. Further, 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, still more preferably 5 mol% or more, and still more preferably 10 mol% or more based on all the structural units of the resin (A). Further, it is preferably 60 mol% or less, more preferably 55 mol% or less, still more preferably 50 mol% or less, even more preferably 40 mol% or less, still even more preferably 30 mol% or less, still more preferably 25 mol% or less, and still even more preferably 20 mol% or less. Specifically, 1 to 60 mol% is preferable, 3 to 60 mol% is more preferable, 3 to 55 mol% is still more preferable, 5 to 55 mol% is still more preferably, 5 to 50 mol% is even more preferably, and 10 to 50 mol% is still even more preferably.

[0109] 〈Structural unit (a4)〉 The structural unit represented by the formula (a4) is shown below. TIFF2025097318000091.tif2869[In the formula (a4), R 41 represents a hydrogen atom or a methyl group. R42 represents an aliphatic hydrocarbon group having a halogen atom with 1 to 48 carbon atoms, and -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O- or -CO-.

[0110] R 42 The aliphatic hydrocarbon group represented by R includes a linear or branched chain hydrocarbon group, a monocyclic or polycyclic alicyclic hydrocarbon group, and a group formed by combining these, etc. Examples of the chain hydrocarbon group include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, pentadecyl group, hexadecyl group, heptadecyl group and octadecyl group, and branched alkyl groups such as isopropyl group and isobutyl group. Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include monocyclic alicyclic hydrocarbon groups which are monocyclic cycloalkyl groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group; polycyclic alicyclic hydrocarbon groups which are polycyclic cycloalkyl groups such as decahydronaphthyl group, adamantyl group, norbornyl group and the following group (* represents the bonding site). Examples of the group 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, -alkanediyl group-alicyclic hydrocarbon group-alkyl group, etc. Examples of the alkanediyl group include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group and hexane-1,6-diyl group; branched alkanediyl groups such as propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-methylbutane-1,4-diyl group and 2-methylbutane-1,4-diyl group. The terminal of the branched alkanediyl group may be a methyl group. R42 Examples of the halogen atom included in the aliphatic hydrocarbon group include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. R 42 Examples of the group in which -CH2- of the aliphatic hydrocarbon group included in is replaced by -O- or -CO- include a hydroxy group, a carboxy group, a carbonyl group, an oxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkanedioxy group, an alkanedioxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, a cycloalkoxy group, a cycloalkylalkoxy group, a group formed by combining two or more of these groups, and the like. These replaced groups include those similar to the groups exemplified in this specification within the range where the upper limit of the number of carbon atoms permits.

[0111] As the structural unit (a4), R 42 is preferably an aliphatic hydrocarbon group having a fluorine atom, and an example of the structural unit (a4) in which R 42 is an aliphatic hydrocarbon group having a fluorine atom includes a structural unit represented by the formula (a4-1) (hereinafter, may be referred to as "structural unit (a4-1)"), a structural unit represented by the formula (a4-2) (hereinafter, may be referred to as "structural unit (a4-2)"), a structural unit represented by the formula (a4-3) (hereinafter, may be referred to as "structural unit (a4-3)"), and a structural unit represented by the formula (a4-A) (hereinafter, may be referred to as "structural unit (a4-A)"). The structural unit represented by the formula (a4-1) is the structural unit shown below. TIFF2025097318000093.tif3192[In the formula (a4-1), R 41 represents a hydrogen atom or a methyl group. L 41 represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. L 42f represents an alkanediyl group having 1 to 8 carbon atoms having a fluorine atom or a cycloalkanediyl group having 3 to 12 carbon atoms having a fluorine atom. R 42frepresents a hydrogen atom or a fluorine atom.

[0112] L 41 Examples of the alkanediyl group in L include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, etc., and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, and 2-methylpropane-1,2-diyl group. The terminal of the branched alkanediyl group may be a methyl group. L 42f Examples of the alkanediyl group having a fluorine atom in L include linear alkanediyl groups having a fluorine atom such as methylene group having a fluorine atom, ethylene group having a fluorine atom, propane-1,3-diyl group having a fluorine atom, butane-1,4-diyl group having a fluorine atom, pentane-1,5-diyl group having a fluorine atom, hexane-1,6-diyl group having a fluorine atom, heptane-1,7-diyl group having a fluorine atom, octane-1,8-diyl group having a fluorine atom; branched alkanediyl groups having a fluorine atom such as ethane-1,1-diyl group having a fluorine atom, propane-1,1-diyl group having a fluorine atom, propane-1,2-diyl group having a fluorine atom, propane-2,2-diyl group having a fluorine atom, pentane-2,4-diyl group having a fluorine atom, 2-methylpropane-1,3-diyl group having a fluorine atom, 2-methylpropane-1,2-diyl group having a fluorine atom, pentane-1,4-diyl group having a fluorine atom, 2-methylbutane-1,4-diyl group having a fluorine atom. The terminal of the branched alkanediyl group may be a methyl group which may have a fluorine atom. L 42fExamples of the cycloalkanediyl group having a fluorine atom in [L] include monocyclic cycloalkanediyl groups having a fluorine atom such as a cyclobutane-1,3-diyl group having a fluorine atom, a cyclopentane-1,3-diyl group having a fluorine atom, a cyclohexane-1,4-diyl group having a fluorine atom, a cyclohexene-3,6-diyl group having a fluorine atom, a cycloheptane-1,4-diyl group having a fluorine atom, and a cyclooctane-1,5-diyl group having a fluorine atom. Examples of the polycyclic cycloalkanediyl group having a fluorine atom include a norbornane-1,4-diyl group having a fluorine atom, a norbornane-2,5-diyl group having a fluorine atom, a 5-norbornene-2,3-diyl group having a fluorine atom, an adamantane-1,5-diyl group having a fluorine atom, and an adamantane-2,6-diyl group having a fluorine atom. L 42f The number of fluorine atoms in the alkanediyl group and the cycloalkanediyl group having a fluorine atom in [L] may be 1 or more, and is preferably 2 or more. L 42f The alkanediyl group and the cycloalkanediyl group having a fluorine atom in [L] are preferably a perfluoroalkanediyl group and a perfluorocycloalkanediyl group, respectively.

[0113] L 42fExamples of the perfluoroalkanediyl group in [the compound] 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, a perfluorohexane-1,6-diyl group, a perfluorohexane-2,2-diyl group, a perfluorohexane-3,3-diyl group, a perfluoroheptane-1,7-diyl group, a perfluoroheptane-2,2-diyl group, a perfluoroheptane-3,4-diyl group, a perfluoroheptane-4,4-diyl group, a perfluorooctane-1,8-diyl group, a perfluorooctane-2,2-diyl group, a perfluorooctane-3,3-diyl group, a perfluorooctane-4,4-diyl group, and the like. L 42f Examples of the perfluorocycloalkanediyl group in [the compound] include a perfluorocyclohexanediyl group, a perfluorocyclopentanediyl group, a perfluorocycloheptanediyl group, a perfluoroadamantanediyl group, and the like.

[0114] L 41 is preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms, more preferably a single bond, a methylene group, or an ethylene group, and even more preferably a single bond or a methylene group. L 42f is preferably a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluorocycloalkanediyl group having 3 to 12 carbon atoms, more preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and even more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0115] Examples of the structural unit (a4-1) include the structural units shown below and R in the structural unit (a4-1) in the following structural units. 41Examples thereof include structural units in which a methyl group corresponding thereto is replaced with a hydrogen atom. TIFF2025097318000094.tif56168 The structural unit represented by formula (a4-2) is the structural unit shown below. TIFF2025097318000095.tif34102[In formula (a4-2), R 41 represents a hydrogen atom or a methyl group. L 43f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. R 43f represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. However, at least one of 43f L 43f and 43f R 43f has a fluorine atom, and the upper limit of the total number of carbon atoms of

[0116] L 43f and 43f R 43f and 43f R 43f and 43f R 42 in formula (a4) is 21.]

[0117] L 43f The aliphatic hydrocarbon group of TIFF2025097318000096.tif13120[In formula (L43f-1), s represents 0 or 1. L 45f and L 46f each independently represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a fluorine atom. L 47f represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a fluorine atom. X 46f and X 47f each independently represents -O-, -CO-, -CO-O- or -O-CO-. However, the total number of carbon atoms of L 45f , L 46f , L 47f , X 46f and X 47f is 7 or less. * and ** are bonding sites, and ** is the bonding site with -O-CO-R 43f .

[0118] In the group represented by formula (L43f-1), L 45f , L 46f and L 47f Examples of the divalent aliphatic hydrocarbon group represented include a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic hydrocarbon group, and a divalent aliphatic hydrocarbon group formed by combining an alkanediyl group and a divalent alicyclic hydrocarbon group. Specifically, a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, etc. can be mentioned. s is preferably 0.

[0119] Examples of the group represented by formula (L43f-1) include the following groups. In the following examples, * and ** each represent a bonding site, and ** is the bonding site with -O-CO-R 43f . TIFF2025097318000097.tif47140

[0120] R43f An aliphatic hydrocarbon group having a fluorine atom is preferred. The structural unit represented by the formula (a4-2) in this case includes, for example, the structural unit represented by the formula (a4-2A) or (formula a4-2B). TIFF2025097318000098.tif41158 [In the formula (a4-2A) and the formula (a4-2B), R 41 and L 43f represent the same as those in the formula (a4-2). R 43fA represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and having a fluorine atom. A 43f represents a divalent aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O- or -CO-. X 43 represents **-O-CO- or **-CO-O-, and ** represents the bonding site with A 43f and represents the bonding site with A. R 43fB represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom. However, in the formula (a4-2A), the total number of carbon atoms of L 43f and R 43fA is 21 or less, and in the formula (a4-2B), the total number of carbon atoms of L 43f , A 43f , X 43 and R 43fB is 21 or less, and among A 43f and R 43fB at least one has at least one fluorine atom. R 43fA The aliphatic hydrocarbon group of R is, as long as the upper limit of the number of carbon atoms allows, the same aliphatic hydrocarbon group as the aliphatic hydrocarbon group exemplified by R 42 . R 43fA is preferably an alkyl group having a fluorine atom and having 1 to 13 carbon atoms, a cycloalkyl group having a fluorine atom and having 3 to 12 carbon atoms, or a group combining them, *-(CF2) n43f -R 42’(* represents the bonding site with the carbonyl group. n43f represents an integer from 1 to 6. R 42’ is more preferably a hydrogen atom, a fluorine atom, or a perfluorocycloalkyl group having 3 to 12 carbon atoms. A 43f and R 43fB 's aliphatic hydrocarbon group, as long as the upper limit of the number of carbon atoms permits, is an aliphatic hydrocarbon group similar to the aliphatic hydrocarbon group exemplified by R 42 in formula (a4). A 43f is preferably a divalent chain hydrocarbon group, a divalent alicyclic hydrocarbon group which may have a fluorine atom, or a group combining them, more preferably a divalent chain hydrocarbon group having a fluorine atom, and even more preferably a fluoroalkanediyl group having 1 to 6 carbon atoms. R 43fB 's aliphatic hydrocarbon group which may have a fluorine atom is preferably a chain hydrocarbon group, an alicyclic hydrocarbon group which may have a fluorine atom, or a group combining them, more preferably an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms which may have a fluorine atom, or a group combining them, and even more preferably a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, a perfluorohexyl group, a heptyl group, a perfluoroheptyl group, an octyl group, a perfluorooctyl group and other fluoroalkyl groups, 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, a perfluoroadamantylmethyl group, etc.

[0121] In formula (a4-2B), *-A f43 -X 43 -R f43B An example of the structure that the group represented by can take is the following structure (* is the bonding site with the carbonyl group). TIFF2025097318000099.tif16170

[0122] Examples of the structural unit represented by formula (a4-2A) include the following structural units and the structural units represented by formula (a4-2A) in the following structural units where the methyl group corresponding to R 41 is replaced by a hydrogen atom. TIFF2025097318000100.tif99165

[0123] Examples of the structural unit represented by formula (a4-2B) include the following structural units and the structural units represented by formula (a4-2B) in the following structural units where the methyl group corresponding to R 41 is replaced by a hydrogen atom. TIFF2025097318000101.tif110163

[0124] Examples of the structural unit (a4) also include the structural unit represented by formula (a4-3). TIFF2025097318000102.tif3689[In formula (a4-3), R 41 represents a hydrogen atom or a methyl group. L 44f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-. R 44f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O- or -CO-. However, at least one of L 44f and R 44f has a fluorine atom, and L 44f and R44f The upper limit of the total carbon number is 21.

[0125] L 44f and R 44f Examples of the aliphatic hydrocarbon group in L 44f and R 44f include linear or branched chain aliphatic hydrocarbon groups, monocyclic or polycyclic alicyclic aliphatic hydrocarbon groups, and groups formed by combining these, etc. 44f and R 44f As long as the upper limit of the total carbon number in L 42 and R permits, examples of the aliphatic hydrocarbon group of R in formula (a4) include the same groups as the exemplified aliphatic hydrocarbon groups. L 44f is preferably an alkanediyl group having 1 to 14 carbon atoms (wherein -CH2- contained in the alkanediyl group may be replaced by -O- or -CO-), and -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 - or -(CH2) j4 -CO-O-(CH2) j5 - (where j1 to j5 each independently represent an integer from 1 to 6). More preferably, it is an alkanediyl group having 1 to 4 carbon atoms (wherein one -CH2- contained in the alkanediyl group may be replaced by -O-, and one -CH2-CH2- contained in the alkanediyl group may be replaced by -CO-O- or -O-CO-). R 44f is preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms having a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms having a fluorine atom, an alicyclic hydrocarbon group having 3 to 10 carbon atoms having a fluorine atom, or a group combining them, still more preferably an alkyl group having 1 to 10 carbon atoms having a fluorine atom, and even more preferably an alkyl group having 1 to 6 carbon atoms having a fluorine atom.

[0126] Examples of the structural unit represented by formula (a4-3) include structural units represented by the following structural units and the following formulas, in which the methyl group corresponding to R in structural unit (a4-3) is replaced by a hydrogen atom. 41 Examples thereof include a structural unit in which the methyl group corresponding to R is replaced by a hydrogen atom. TIFF2025097318000103.tif86170

[0127] Examples of the structural unit (a4) also include a structural unit represented by formula (a4-A). TIFF2025097318000104.tif3686 [In formula (a4-A), all symbols have the same meaning as described above.]

[0128] R 1 Examples of the alkyl group having 1 to 6 carbon atoms in R include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. R 1 Examples of the halogen atom in R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 1 Examples of the alkyl group having 1 to 6 carbon atoms and having a halogen atom in R include a trifluoromethyl group, a difluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a dichloromethyl group, a triiodomethyl group, a diiodomethyl group, a tribromomethyl group, a dibromomethyl group, and the like. R 1 R is 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, still more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group.

[0129] L1 Examples of the aliphatic hydrocarbon group in [description] include a chain hydrocarbon group, a monocyclic or polycyclic (including a spiro ring, a condensed ring, a bridged ring, etc.) alicyclic hydrocarbon group, and a group formed by combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and a chain hydrocarbon group) may also be used. Examples of the chain hydrocarbon group include divalent to pentavalent chain hydrocarbon groups such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, and an alkanepentayl group. 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, 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, and branched alkanediyl groups such as 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. Also, groups in which one or more hydrogen atoms of the above-described groups are replaced with a bonding site, etc. are also included. The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, still more preferably 1 to 10, even more preferably 1 to 9, still even more preferably 1 to 8, still more preferably 1 to 6, still even more preferably 1 to 5, and particularly preferably 1 to 4.

[0130] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following alicyclic hydrocarbon groups, etc. The bonding site can be at any position. TIFF2025097318000105.tif45164For example, divalent to pentavalent alicyclic hydrocarbon groups such as cycloalkanediyl groups, cycloalkanetriyl groups, cycloalkanetetrayl groups, cycloalkanepentayl groups, etc. can be mentioned. Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, etc. and Polycyclic alicyclic hydrocarbon groups such as spiro rings having a cycloalkanediyl group, norbornanediyl group or adamantanediyl group each having a cycloalkanediyl group, norbornanediyl group or adamantanediyl group spiro-bonded thereto, such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, decahydronaphthalenediyl group, bicyclo[3.3.0]octanediy group, spirocyclohexane-1,2'-cyclopentane-diyl group, spiroadamantane-2,3'-cyclopentane-diyl group, etc. can be mentioned. Moreover, groups in which one or more of the hydrogen atoms of the above-mentioned groups are replaced at the bonding site, etc. can also be mentioned. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12.

[0131] Examples of the group formed by combining two or more types include a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group. In the combination, the alicyclic hydrocarbon group and the chain hydrocarbon group may each be combined with two or more types. Also, any group may be bonded to X 11 It may be bonded. Examples of a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group include a group in which an alicyclic hydrocarbon group is bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group - alicyclic hydrocarbon group - etc.), a group in which a chain hydrocarbon group is bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group - chain hydrocarbon group - etc.), a group in which an alicyclic hydrocarbon group and a chain hydrocarbon group are bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - etc.), a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - etc.), a group in which an alicyclic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group are bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - etc.), a group in which a chain hydrocarbon group, an alicyclic hydrocarbon group, and a chain hydrocarbon group are bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - etc.), and the like. * represents the bonding site with X. 11 Also included are groups in which one or more hydrogen atoms of the above-described groups are replaced with a bonding site.

[0132] L 1 In the aliphatic hydrocarbon group having 1 to 28 carbon atoms in L, -CH2- may be replaced by -O-, -S-, -SO2- or -CO-. L 1 When -CH2- contained in the aliphatic hydrocarbon group having 1 to 28 carbon atoms in L is replaced by -O-, -S-, -SO2- or -CO-, the carbon number before replacement is taken as the carbon number of the aliphatic hydrocarbon group. Examples of the group in which -CH2- contained in the aliphatic hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include a hydroxy group, a carboxy group, a thiol group, an alkoxy group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an oxy group, a carbonyl group, a thio group, a sulfonyl group, an alkanedioxy group, an alkanedioxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, a cycloalkoxy group, a cycloalkylalkoxy group, a group formed by combining two or more of these groups, and the like. These replaced groups include those similar to the groups exemplified in this specification within the range where the upper limit of the number of carbon atoms is allowed. Examples also include a group in which one or more hydrogen atoms of the above-described group are replaced by a bonding site. Examples of the group in which -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- include those similar to the groups exemplified in this specification within the range where the upper limit of the number of carbon atoms is allowed.

[0133] L 1 The aliphatic hydrocarbon group in L may have one or more substituents. Examples of the substituent include a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl 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 (wherein -CH2- contained in the alkyl group or the alicyclic hydrocarbon group may be replaced by -O- or -CO-). Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. The haloalkyl groups having 1 to 4 carbon atoms include fluoroalkyl groups having 1 to 4 carbon atoms, chloroalkyl groups having 1 to 4 carbon atoms, bromoalkyl groups having 1 to 4 carbon atoms, iodoalkyl groups having 1 to 4 carbon atoms, and the like. Examples of the haloalkyl group include perfluoroalkyl groups having 1 to 4 carbon atoms (such as trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, iodomethyl group, and the like. The number of carbon atoms of the haloalkyl group is preferably 1 to 3, more preferably 1 or 2. Examples of the alkyl group having 1 to 12 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, and the like. The number of carbon atoms of the alkyl group is preferably 1 to 9, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. When -CH2- contained in the alkyl group is replaced by -O- or -CO-, the total number of carbon atoms before replacement is defined as the total number of carbon atoms of the alkyl group. Examples of the replaced group include hydroxy group, carboxy group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkoxycarbonyloxy group, and the like. L 1 Examples of the substituent that the aliphatic hydrocarbon group in L may have include halogen atom, haloalkyl group having 1 to 3 carbon atoms, alkyl group having 1 to 6 carbon atoms, alicyclic hydrocarbon group having 3 to 10 carbon atoms, or aromatic hydrocarbon group having 6 to 10 carbon atoms (wherein -CH2- contained in the alkyl group or the alicyclic hydrocarbon group may be replaced by -O- or -CO-). Fluorine atom, iodine atom, perfluoroalkyl group having 1 to 3 carbon atoms, or alkyl group having 1 to 4 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-) are more preferred. Fluorine atom, iodine atom, trifluoromethyl group, methyl group, hydroxy group, or methoxy group are even more preferred. L1 is, when it does not form an alkyl fluoride group and an alicyclic hydrocarbon group of R 3 a chain hydrocarbon group having 1 to 12 carbon atoms which may have a substituent (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O- or -CO-), or a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent and an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O- or -CO-), preferably, a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 12 carbon atoms which may have a substituent, or a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent and an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), more preferably, a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent, a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms and an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), or a group formed by combining an alicyclic hydrocarbon group having 5 to 12 carbon atoms, a chain hydrocarbon group having 1 to 6 carbon atoms and an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), still more preferably.

[0134] R 2Examples of the alkyl fluoride group having 1 to 8 carbon atoms include difluoromethyl group, trifluoromethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 1,1,2,2-tetrafluoropropyl group, 1,1,2,2,3,3-hexafluoropropyl group, perfluoroethylmethyl group, 1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl group, perfluoropropyl group, 1,1,2,2-tetrafluorobutyl group, 1,1,2,2,3,3-hexafluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, perfluorobutyl group, 1,1-bis(trifluoro)methyl-2,2,2-trifluoroethyl group, 2-(perfluoropropyl)ethyl group, 1,1,2,2,3,3,4,4-octafluoropentyl group, perfluoropentyl group, 1,1,2,2,3,3,4,4,5,5-decafluoropentyl group, 1,1-bis(trifluoromethyl)-2,2,3,3,3-pentafluoropropyl group, perfluoropentyl group, 2-(perfluorobutyl)ethyl group, 1,1,2,2,3,3,4,4,5,5-decafluorohexyl group, 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexyl group, perfluoropentylmethyl group, perfluorohexyl group, perfluoroheptyl group, and perfluorooctyl group. The number of carbon atoms of the alkyl fluoride group is preferably 1 to 6, more preferably 1 to 5, still more preferably 1 to 4, and even more preferably 1 to 3. R 3 When the alkyl fluoride group having 1 to 6 carbon atoms is R 2 the alkyl fluoride groups having 1 to 6 carbon atoms exemplified in the examples of the alkyl fluoride group of R R 2 is preferably an alkyl fluoride group having 1 to 6 carbon atoms, more preferably an alkyl fluoride group having 1 to 3 carbon atoms, still more preferably a trifluoromethyl group, a perfluoroethyl group or a perfluoropropyl group, and even more preferably a trifluoromethyl group when R 3 is an alkyl fluoride group having 1 to 6 carbon atoms. R2 is, when R 3 is a hydrogen atom, preferably an alkyl fluoride group having 1 to 6 carbon atoms, more preferably an alkyl fluoride group having 1 to 5 carbon atoms, and still more preferably an alkyl fluoride group having 3 to 5 carbon atoms. R 3 is bonded to L 1 to form an alicyclic hydrocarbon group having 3 to 12 carbon atoms, R 3 is bonded to L 1 Examples of the group formed by the bond include groups represented by the following formulae. In the following formulae, * and ** represent bonding sites, two ** represent one as the bonding site with a hydroxy group and the other as the bonding site with R 2 and L 1A is a part of the hydrocarbon group of L 1 and represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. R 3 is bonded to L 1 The number of carbon atoms of the alicyclic hydrocarbon group formed by the bond is preferably 3 to 10, more preferably 3 to 8, and still more preferably 3 to 6. TIFF2025097318000106.tif21138R 3 is preferably a hydrogen atom or an alkyl fluoride group having 1 to 3 carbon atoms. mi is preferably any integer from 1 to 3, more preferably 1 or 2, and still more preferably 1.

[0135] Examples of the structural unit (a4-A) include the following structural units and the like. In the following structural units, structural units in which the methyl group corresponding to R 1 is replaced by a hydrogen atom, a halogen atom, a haloalkyl group or an alkyl group other than a methyl group, and structural units in which the hydrogen atom corresponding to R 1 is replaced by a halogen atom, a haloalkyl group or an alkyl group can also be cited as specific examples of the structural unit (a4-A). TIFF2025097318000107.tif191168

[0136] When the resin (A) contains the structural unit (a4), its content is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and still more preferably 3 to 10 mol% based on all the structural units of the resin (A).

[0137] 〈Structural unit (a5)〉 Examples of the non-detachable hydrocarbon group contained in the structural unit (a5) include groups having a linear, branched or cyclic hydrocarbon group. Among them, the structural unit (a5) preferably has a group having an alicyclic hydrocarbon group. Examples of the structural unit (a5) include a structural unit represented by the formula (a5-1). TIFF2025097318000108.tif3971[In the 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 the hydrogen atoms contained in the alicyclic hydrocarbon group may be substituted with aliphatic hydrocarbon groups having 1 to 8 carbon atoms. L 55 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.]

[0138] R 52 The alicyclic hydrocarbon group in R may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the polycyclic alicyclic hydrocarbon group include an adamantyl group and a norbornyl group. Examples of the aliphatic hydrocarbon group having 1 to 8 carbon atoms include alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, and a 2-ethylhexyl group. Examples of the alicyclic hydrocarbon group having a substituent include a 3-methyladamantyl group. R 52is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, more preferably an adamantyl group, a norbornyl group or a cyclohexyl group. L 55 Examples of the divalent saturated hydrocarbon group in include divalent chain saturated hydrocarbon groups and divalent alicyclic saturated hydrocarbon groups, preferably divalent chain saturated hydrocarbon groups. Examples of the divalent chain saturated hydrocarbon group include alkane diyl groups such as a methylene group, an ethylene group, 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 cycloalkane diyl groups such as a cyclopentanediyl group and a cyclohexanediyl group. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include an adamantanediyl group and a norbornanediyl group.

[0139] L 55 Examples of the group in which -CH2- contained in the divalent saturated hydrocarbon group represented by is replaced by -O- or -CO- include the groups represented by formula (L1-1) to formula (L1-4). In the following formulas, * and ** each represent a bonding site, and * represents a bonding site with an oxygen atom. TIFF2025097318000109.tif18165[In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents the bonding site with L x1 represents the bonding 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, the total number of carbon atoms of L x1 and L x2 is 16 or less. In formula (L1-2), L x3 represents a divalent aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms. L x4represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. However, the total number of carbon atoms in L x3 and L x4 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 represent a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 14 carbon atoms. However, the total number of carbon atoms in L x5 , L x6 and L x7 is 15 or less. In formula (L1-4), L x8 and L x9 represent a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms. W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, the total number of carbon atoms in L x8 , L x9 and W x1 is 15 or less. L x1 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x2 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond. L x3 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x6is 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.

[0140] Examples of the group represented by the formula (L1-1) include the following divalent groups. TIFF2025097318000110.tif36148 Examples of the group represented by the formula (L1-2) include the following divalent groups. TIFF2025097318000111.tif23130 Examples of the group represented by the formula (L1-3) include the following divalent groups. TIFF2025097318000112.tif16147 Examples of the group represented by the formula (L1-4) include the following divalent groups. TIFF2025097318000113.tif13168L 55 is preferably a single bond or a group represented by the formula (L1-1).

[0141] Examples of the structural unit (a5-1) include the following structural units and the structural units in which the methyl group corresponding to R in the following structural units of the structural unit (a5-1) is replaced by a hydrogen atom. 51 are mentioned. When the resin (A) contains the structural unit (a5), its content is preferably 1 to 30 mol%, more preferably 2 to 20 mol%, and still more preferably 3 to 15 mol% based on all the structural units of the resin (A).

[0142] 〈Structural unit (a6)〉 The structural unit (a6) is a structural unit having a -SO2- group, and preferably has a -SO2- group in the side chain. The structural unit having a -SO2- group may have a linear structure having a -SO2- group, a branched structure having a -SO2- group, or a cyclic structure (monocyclic and polycyclic structures) having a -SO2- group. Preferably, it is a structural unit having a cyclic structure having a -SO2- group, and more preferably, it is a structural unit having a cyclic structure (sultone ring) containing -SO2-O-.

[0143] Examples of the sultone ring include the following formula (T 1 -1), formula (T 1 -2), formula (T 1 -3) and formula (T 1 -4). The bonding site can be at any position. The sultone ring may be monocyclic, but is preferably polycyclic. The polycyclic sultone ring means a bridged ring containing -SO2-O- as an atomic group constituting the ring, and examples include the rings represented by formula (T 1 -1) and formula (T 1 -2). The sultone ring may further contain a heteroatom in addition to -SO2-O- as an atomic group constituting the ring, like the ring represented by formula (T 1 -2). Examples of the heteroatom include an oxygen atom, a sulfur atom or a nitrogen atom, and preferably an oxygen atom. TIFF2025097318000115.tif3177

[0144] 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.

[0145] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. 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. Preferably, it is 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. Preferably, a trifluoromethyl group is mentioned. Examples of the alkyl group having a hydroxy group include a hydroxymethyl group and a hydroxyalkyl group such as 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. Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, a naphthylmethyl group, and a naphthylethyl group. 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, preferably an alkoxycarbonyl group having 6 or fewer carbon atoms, and more preferably a methoxycarbonyl group. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. From the viewpoint that the production of the monomer leading to the structural unit (a6) is easy, a sultone ring having no substituent is preferable.

[0146] As the sultone ring, a ring represented by the following formula (T1') is preferable. TIFF2025097318000116.tif2666[In the 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 any integer from 0 to 9. When ma is 2 or more, a plurality of R 41 may be the same or different. The bonding site is at an arbitrary position.] X 11 is preferably an oxygen atom or a methylene group, and more preferably a methylene group. R 41 includes the same ones as the substituents of the sultone ring, and an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group is preferable. ma is preferably 0 or 1, and more preferably 0.

[0147] Examples of the ring represented by formula (T1’) include the following rings. The bonding site can be at any position. Among them, the bonding site is preferably at the 1-position or 3-position. TIFF2025097318000117.tif44148

[0148] The structural unit having a -SO2- group preferably further has a group derived from a polymerizable group. Examples of the polymerizable group include a vinyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, an acryloylthio group, a methacryloylthio group, and the like. Among them, the monomer that leads to the structural unit (a6) is preferably a monomer having an ethylenically unsaturated bond, more preferably a (meth)acrylic monomer.

[0149] The structural unit (a6) is preferably a structural unit represented by formula (a6-0). TIFF2025097318000118.tif4177[In formula (a6-0), R x represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom, or a halogen atom. A xx represents 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 may be replaced by -O-, -CO-, or -N(R d )-. X 11 represents an oxygen atom, a sulfur atom, or a methylene group. R 41 represents the same group as described above. ma represents any integer from 0 to 9. When ma is 2 or more, a plurality of R 41 may be the same or different. R c and R d each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0150] R x Examples of the halogen atom of R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R x Examples of the alkyl group of R include, for example, 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, etc. Preferably, it is an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. R x Examples of the alkyl group having a halogen atom of R include, for example, 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, etc. R x R 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. A x Examples of the divalent saturated hydrocarbon group of A include a linear alkanediyl group, a branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and combinations of two or more of these groups may also be used. Specifically, linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, heptadecane-1,17-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group and propane-2,2-diyl group; Branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group; Monocyclic divalent alicyclic saturated hydrocarbon groups which are cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group; Polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc. can be mentioned. A x The bonding position to the sultone ring of A can be any position, but the one at the 1-position is preferred.

[0151] Examples of the structural unit (a6-0) include the following structural units. TIFF2025097318000119.tif93150

[0152] Among them, the 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 the structural units represented by formula (a6-1), formula (a6-2), formula (a6-7) and (a6-8) are more preferred. When the resin (A) contains the structural unit (a6), its content is preferably 1 to 50 mol%, more preferably 2 to 40 mol%, and still more preferably 3 to 30 mol% based on all the structural units of the resin (A).

[0153] <Structural unit (a7)> The resin (A) may further contain a structural unit that decomposes upon exposure to generate an acid (hereinafter sometimes referred to as "structural unit (a7)"). Specific examples of the structural unit (a7) include the structural units described in JP-A-2016-79235, and it is preferably a structural unit having a sulfonate group or a carboxylate group and an organic cation in the side chain or a structural unit having a sulfonio group and an organic anion in the side chain.

[0154] The structural unit having a sulfonate group or a carboxylate group and an organic cation in the side chain is preferably a structural unit represented by the formula (a7-A). TIFF2025097318000120.tif26125[In the formula (a7-A), R a7 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X a71 represents a single bond, *-O-*, *-CO-O-*, *-O-CO-O-*, *-CO-NR a71 -*, *-NR a71 -CO-O-*, *-O-CO-NR a71 -* or *-Ax-Ph-Ay-*. R a71 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ph represents a phenylene group which may have a substituent. Ax and Ay each independently represent one or more bond types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond. * and ** represent bonding sites, and * represents the bonding site with the carbon atom to which R a7 is bonded. L a71and L a72 each independently represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-. X a72 represents ***-CO-O-, ***-O-CO-, ***-O-CO-O-, ***-O-, where *** represents L a71 and represents the bonding site with na7 represents any integer from 0 to 2. When na7 is 2, the groups within multiple parentheses may be the same as or different from each other. RA - represents a sulfonate anion or a carboxylate anion. ZA + represents an organic cation.

[0155] R a7 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R are the same as those exemplified by R of formula (a1-0). a01 and the like can be mentioned. R a7 is 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, still more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group.

[0156] X a71 When X is a group represented by *-Ax-Ph-Ay-**, it is preferably a linking group represented by the following formula (X10). TIFF2025097318000121.tif3251 [In formula (X10), Ax represents the bonding species that binds to the carbon atom to which R a7 is bonded, and represents one or more bonding species selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, a carbonate ester bond, and an amide bond. Ay represents L a71Represents a bonding type that binds to, and represents one or more bonding types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, a carbonate bond, and an amide bond. Rx represents a halogen atom, a hydroxy group, a C1-C6 fluoroalkyl group, a C1-C18 alkyl group, or a C1-C6 alkoxy group. mx represents any integer from 0 to 4, and when mx is an integer of 2 or more, the plurality of Rx may be the same as or different from each other. When either Ax or Ay is a single bond, it is preferable that the other is one or more selected from the group consisting of an ether bond, a thioether bond, an ester bond, a carbonate bond, and an amide bond. When either Ax or Ay is an amide bond, it is preferably a bond represented by -CO-NR a71 -. The bonding position of Ay in the phenylene group is preferably the m-position or the p-position with respect to the bonding position of Ax, and more preferably the p-position. Among them, Rx is preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, or an ethyl group. mx is preferably 0, 1, or 2. X a71 Examples of X 10 -1) to the group represented by the formula (X 10 -10). * represents the bonding site with the carbon atom to which -R a7 is bonded. ** represents the bonding site with L a71 . X 20 represents -O- or -NR a71 -. TIFF2025097318000122.tif44163 The groups represented by the formula (X 10 -1) to the formula (X 10 -10) include the following groups as specific examples. TIFF2025097318000123.tif87163 Among them, X a71 is a single bond or the formula (X 10 -1’) and the formula (X 10 -3’) to the formula (X10 It is preferably a group represented by any one of -10’), and is a single bond or formula (X 10 -1’), formula (X 10 -4’), formula (X 10 -5’), formula (X 10 -6’) and formula (X 10 -10’), more preferably a single bond, a group represented by formula (X 10 -1’), a group represented by formula (X 10 -5’) or a group represented by formula (X 10 -6’).

[0157] L a71 Examples of the hydrocarbon group of include a group obtained by removing one hydrogen atom from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups, and combining with X a71 and X a72 . Further, examples of the hydrocarbon group of L a72 include a group obtained by removing one hydrogen atom from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups, and combining with X a72 and RA - . L a71 and L a72 Examples of the chain hydrocarbon group of include a group obtained by removing one hydrogen atom from an alkyl group or an alkenyl group. The alkyl group may be linear or branched, and specifically includes a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a heptadecyl group, etc. Examples of the alkenyl group include an ethenyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, an isooctenyl group, a nonenyl group, etc. The number of carbon atoms in the chain hydrocarbon group is preferably from 1 to 20, more preferably from 1 to 18, and even more preferably from 1 to 10. L a71 and L a72 Examples of the alicyclic hydrocarbon group of a72 include a group obtained by removing one hydrogen atom from a monocyclic or polycyclic cycloalkyl group. Examples of the monocyclic cycloalkyl group include a cyclobutyl group, a cycloheptyl group, a cyclohexyl group, a cyclopentyl group, a cyclooctyl group, and the like. L a71 and L a72 Examples of the polycyclic cycloalkyl group of a72 include a cycloalkyl group having a crosslinked structure, a cycloalkyl group in which two or more rings are condensed, or a cycloalkyl group in which two rings are spiro-bonded. Examples of the cycloalkyl group having a crosslinked structure include a norbornyl group, an adamantyl group, and the like. Examples of the cycloalkyl group in which two or more rings are condensed include a bicyclo[4,4,0]decane group, a steroid group (steroid skeleton), and the like. Examples of the cycloalkyl group in which two rings are spiro-bonded include a spirocyclic cycloalkyl group in which one or more cycloalkyl groups selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group and a cycloalkyl group having 5 to 8 carbon atoms are spiro-bonded. Further, a double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group. More specifically, the alicyclic hydrocarbon groups represented by the following formulas can be mentioned. TIFF2025097318000124.tif28158 When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably from 3 to 18, more preferably from 3 to 12, and even more preferably from 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably from 6 to 18, more preferably from 7 to 12. L a71 and L a72Examples of the aromatic hydrocarbon group include a group obtained by removing one hydrogen atom from an aryl group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a fluorenyl group, and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 5 to 14, more preferably 6 to 14, and even more preferably 6 to 10. L a71 and L a72 When -CH2- contained in the hydrocarbon group of and L is replaced by -O-, -CO-, -S- or -SO2-, the number of carbon atoms before replacement is defined as the number of carbon atoms of the hydrocarbon group. L a71 and L a72 Examples of the group in which -CH2- contained in the chain hydrocarbon group among the hydrocarbon groups of and L is replaced by -O-, -CO-, -S- or -SO2- include a hydroxy group, a carboxy group, a thiol group, a carbonyl group, an oxy group, a thio group, a sulfonyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkanedioxy group, an alkanedioxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, and the like. These replaced groups include those similar to the groups exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms. L a71 and L a72 Examples of the group in which -CH2- contained in the group combining an alicyclic hydrocarbon group or an alicyclic saturated hydrocarbon group and an aromatic hydrocarbon group among the hydrocarbon groups of and L is replaced by -O-, -CO-, -S- or -SO2- include those similar to the groups exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms. L a71 and L a72 Among the hydrocarbon groups of and L, -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-. Examples of the group in which -CH2- is replaced by -O- or -S- include groups derived from a furan ring or a thiophene ring, respectively. L a71 and L a72Examples of a group formed by combining two or more of an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group include a group formed by combining the above aliphatic hydrocarbon group and the above alicyclic hydrocarbon group, a group formed by combining the above aliphatic hydrocarbon group and the above aromatic hydrocarbon group, a group formed by combining the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group, and a group formed by combining the above aliphatic hydrocarbon group, the above alicyclic hydrocarbon group, and the above aromatic hydrocarbon group. The group formed by combining the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be a condensed ring. L a71 and L a72 Examples of the substituent that the hydrocarbon group of may have include a halogen atom, a cyano group, and a nitro group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L a71 and L a72 When and are a group formed by combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group and an aliphatic hydrocarbon group, substantially, the aliphatic hydrocarbon group may be regarded as a substituent that the alicyclic hydrocarbon group or the aromatic hydrocarbon group has. Also, L a71 and L a72 When the -CH2- of the aliphatic hydrocarbon group contained in the hydrocarbon group of is replaced by -O-, -CO-, -S-, or -SO2-, L a71 and L a72 The hydrocarbon group of may substantially have substituents such as a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a thiol group, and a sulfonyl group. na7 is preferably 0 or 1. ZA in formula (a7-A) + is the same as those exemplified for the cation in the salt represented by formula (B1) and the like.

[0158] In formula (a7-A), L a71 and L a72 When the hydrocarbon group of is a saturated hydrocarbon group, in formula (a7-B) described later, A b7 may contain the same groups as those exemplified as the divalent linking group of. Examples of the structural unit represented by formula (a7-A) include the structural unit represented by formula (a7-A1). TIFF2025097318000125.tif31138[In formula (a7-A1), R a7 、X a71 、L a71 、X a72 、na7、RA - and ZA + have the same meanings as defined above. z7 represents any integer from 0 to 6. Q a7 、Q b7 、R z71 and R z72 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. When z7 is 2 or more, a plurality of R z71 and R z72 may be the same as or different from each other.] Q a7 、Q b7 、R z71 and R z72 Examples of the perfluoroalkyl group having 1 to 6 carbon atoms or the alkyl group having 1 to 6 carbon atoms in include the same groups as those exemplified for R a7 .

[0159] Examples of the structural unit represented by formula (a7-A) include, for example, the following structural units, a group corresponding to the methyl group of R a7 wherein the hydrogen atom, a halogen atom (e.g., a fluorine atom), or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (e.g., a trifluoromethyl group, etc.) is replaced, and the structural units described in WO 2012 / 050015. ZA + represents an organic cation. TIFF2025097318000126.tif244163

[0160] TIFF2025097318000127.tif130158

[0161] The structural unit having a sulfonio group and an organic anion in the side chain is preferably a structural unit represented by the formula (a7-B). TIFF2025097318000128.tif28105[In the formula (a7-B), R a7 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. A b7 represents a single bond or a divalent linking group. R b71 represents a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. R b72 and R b73 each independently represent a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and R b72 and R b73 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded. A - represents an organic anion.] R a7 Examples of the halogen atom and the alkyl group which may have a halogen atom of R include the same halogen atom and the alkyl group which may have a halogen atom as those in the formula (a7-A). R b71 Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by include a phenylene group and a naphthylene group. R b72 and R b73 Examples of the hydrocarbon group represented by include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these. Examples of the alkyl group, the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and the group formed by combining these include the same as those described above. A b7 Examples of the divalent linking group represented by include a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O-, -S-, or -CO-. Examples of the divalent saturated hydrocarbon group include a divalent chain-like saturated hydrocarbon group such as a linear or branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and combinations thereof may also be used. Specifically, linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group; branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group; divalent monocyclic alicyclic saturated hydrocarbon groups which are monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group; divalent polycyclic alicyclic saturated hydrocarbon groups which are polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc. may be mentioned. Examples of the group in which -CH2- contained in the saturated hydrocarbon group is replaced by -O-, -S- or -CO- include the following divalent groups. However, the number of carbon atoms before -CH2- contained in the saturated hydrocarbon group is replaced by -O-, -S- or -CO- is 17 or less respectively. In the following formula, * and ** represent bonding sites, and * represents the bonding site with R b71 and represents the bonding site with R. TIFF2025097318000129.tif122161[In the formula, X 3 represents a divalent saturated hydrocarbon group having 1 to 16 carbon atoms. X 4 represents a divalent saturated hydrocarbon group having 1 to 15 carbon atoms. X 5 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms. X 6represents a divalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 7 represents a trivalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 8 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.

[0162] Examples of the structural unit containing the cation in formula (a7-B) include the structural units represented below and groups corresponding to the methyl group of R a7 wherein the hydrogen atom, halogen atom (e.g., fluorine atom) or alkyl group having 1 to 6 carbon atoms which may have a halogen atom (e.g., trifluoromethyl group, etc.) is substituted for the methyl group of R, etc. JPEG2025097318000130.jpg72163

[0163] A - Examples of the organic anion represented by A include sulfonate anions, sulfonylimide anions, sulfonylmethide anions, carboxylic acid anions, etc. - The organic anion represented by A is preferably a sulfonate anion, and more preferably the same as the anion exemplified by the acid generator (B). Examples of the sulfonylimide anion, sulfonylmethide anion and carboxylic acid anion include the same as the anion exemplified by the acid generator (B).

[0164] Examples of the structural unit represented by formula (a7-B) include the structural units represented below. TIFF2025097318000131.tif95157

[0165] When the resin (A) contains the structural unit (a7), the structural unit (a7) may be contained alone or in combination of two or more. The content of the total structural unit (a7) is preferably 1 to 30 mol%, more preferably 2 to 25 mol%, still more preferably 3 to 20 mol%, even more preferably 3 to 15 mol%, and even more preferably 3 to 10 mol% based on all the structural units of the resin (A).

[0166] The resin (A) may contain structural units other than the above-mentioned structural units, and examples of such structural units include structural units well-known in the art.

[0167] The resin (A) is preferably a resin composed of the structural unit (a1) and the structural unit (s), that is, a copolymer of the monomer (a1) and the monomer (s). The structural unit (a1) is preferably at least one selected from the group consisting of the structural unit (a1-0), the structural unit (a1-1), the structural unit (a1-2) (preferably the structural unit having a cyclohexyl group or a cyclopentyl group), the structural unit represented by the formula (a1-4), the structural unit represented by the formula (a1-5), and the structural unit represented by the formula (a1-6), and more preferably at least one 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 represented by the formula (a2-A) or the structural unit represented by the formula (a2-C). The structural unit (a3) is preferably at least one selected from the group consisting of the structural unit represented by the formula (a3-1), the structural unit represented by the formula (a3-2), and the structural unit represented by the formula (a3-4).

[0168] Each structural unit constituting the resin (A) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using monomers that lead to these structural units. The content of each structural unit of the resin (A) can be adjusted by the amount of monomers used in the polymerization. The weight average molecular weight of the resin (A) is preferably 2,000 or more (more preferably 2,500 or more, still more preferably 3,000 or more), 50,000 or less (more preferably 30,000 or less, still more preferably 15,000 or less), but may contain oligomers having a weight average molecular weight smaller than this. In this specification, the weight average molecular weight is a value determined by gel permeation chromatography under the conditions described in the examples.

[0169] <Resin other than resin (A)> The resist composition of the present invention may be used in combination with a resin other than the resin (A). Examples of the resin other than the resin (A) include resins containing the structural unit (a2), the structural unit (a4), or the structural unit (a5) (hereinafter sometimes referred to as resin (X)). Among them, examples of the resin (X) include resins composed only of the structural unit (a2), resins composed only of the structural unit (a4), and resins composed of the structural unit (a4) and the structural unit (a5). Examples of the structural unit that the resin (X) may further have include the structural unit (a3) and structural units derived from other known monomers. When the resin (X) contains the structural unit (a2), the structural unit (a2) is preferably the structural unit (a2-A) or the structural unit (a2-B). When the resin (X) contains the structural unit (a4), in the resin (X), the content of the structural unit (a4) is 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and still more preferably 45 mol% or more, based on the total of all the structural units of the resin (X). Also, it is 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, it is 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, still more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. When the resin (X) contains the structural unit (a5), the content of the structural unit (a5) is 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and still more preferably 45 mol% or more, based on the total of all the structural units of the resin (X). Also, it is 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, it is 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, still more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. Further, 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) is 40 mol% or more, preferably 60 mol% or more, more preferably 70 mol% or more, and still more preferably 80 mol% or more, based on the total of all the structural units of the resin (X). Also, it is 100 mol% or less. Specifically, it is 40 to 100 mol%, preferably 60 to 100 mol%, more preferably 70 to 100 mol%, and still more preferably 80 to 100 mol%. Among them, the resin (X) is preferably a resin composed of only the structural unit (a4) and / or the structural unit (a5). In this case, the ratio of the structural unit (a4): the structural unit (a5) is 0:100 to 100:0, preferably 10:90 to 90:10, and more preferably 30:70 to 70:30 or 40:60 to 60:40. Each structural unit constituting the resin (X) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using the monomers that induce these structural units. The content of each structural unit of the resin (X) can be adjusted by the amount of monomers used in the polymerization. The weight average molecular weight of the 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 may contain oligomers having a weight average molecular weight smaller than this. The measuring means of the weight average molecular weight of the resin (X) is the same as that of the resin (A).

[0170] When the resist composition of the present invention contains the resin (X), its content is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, still more preferably 1 to 40 parts by mass, even more preferably 1 to 30 parts by mass, and particularly preferably 1 to 8 parts by mass with respect to 100 parts by mass of the resin (A).

[0171] The content of the resin (A) in the resist composition is preferably 60% by mass or more and 99% by mass or less, more preferably 70% by mass or more and 99% by mass or less, still more preferably 80% by mass or more and 99% by mass or less, and even more preferably 90% by mass or more and 99% by mass or less with respect to the solid content of the resist composition. When containing a resin other than the resin (A), the total content of the resin (A) and the resin other than the resin (A) is preferably 60% by mass or more and 99% by mass or less, more preferably 70% by mass or more and 99% by mass or less, still more preferably 80% by mass or more and 99% by mass or less, and even more preferably 90% by mass or more and 99% by mass or less with respect to the solid content of the resist composition. The solid content of the resist composition and the content of the resin with respect thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0172] <Solvent (E)> The content of the solvent (E) in the resist composition is usually 90% by mass or more and 99.9% by mass or less, preferably 92% by mass or more and 99% by mass or less, and more preferably 94% by mass or more and 99% by mass or less. The content of the solvent (E) can be measured by known analytical means such as liquid chromatography or gas chromatography. 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; and the like. One kind of the solvent (E) may be used alone, or two or more kinds may be used.

[0173] <Quencher (C)> Examples of the quencher (C) include salts that generate an acid having a lower acidity than the acid generated from a basic nitrogen-containing organic compound or an acid generator (for example, the acid generator (B), etc.). When the resist composition contains the quencher (C), the content of the quencher (C) is preferably about 0.01 to 15% by mass, more preferably about 0.01 to 10% by mass, further 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. Examples of the basic nitrogen-containing organic compound include amines and ammonium salts. Examples of the amines include aliphatic amines and aromatic amines. Examples of the aliphatic amines include primary amines, secondary amines, and tertiary amines. Examples of the amine 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, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, methyldibutylamine, methyldipentylamine, methyldihexylamine, methyldicyclohexylamine, methyldiheptylamine, methyldioctylamine, methyldinonylamine, methyldidecylamine, ethyldibutylamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine, ethyldioctylamine, ethyldinonylamine, ethyldidecylamine, 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, 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'-dipyridylsulfide, 4,4'-dipyridyldisulfide, 2,2'-dipyridylamine, 2,2'-dipicolylamine, bipyridine, etc. Aromatic amines such as diisopropylaniline are preferable, and 2,6-diisopropylaniline is more preferable. Examples of the ammonium salt include tetramethylammonium hydroxide, tetraisopropylammonium hydroxide, tetrabutylammonium hydroxide, tetrahexylammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethylammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium hydroxide, tetra-n-butylammonium salicylate, choline, and the like.

[0174] The acidity of a salt that generates an acid with a lower acidity than the acid generated from the acid generator is indicated by the acid dissociation constant (pKa). A salt that generates an acid with a lower acidity than the acid generated from the acid generator is a salt having an acid dissociation constant of the acid generated from the salt usually of -3 < pKa, preferably -1 < pKa < 7, and more preferably 0 < pKa < 5. Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator include salts represented by the following formula, salts represented by formula (D) described in JP-A-2015-147926 (hereinafter sometimes referred to as "weak acid inner salt (D)"), and salts described in JP-A-2012-229206, JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-39502, and JP-A-2011-191745. The salt that generates an acid with a lower acidity than the acid generated from the acid generator is preferably a salt that generates a carboxylic acid with a lower acidity than the acid generated from the acid generator (a salt having a carboxylic acid anion), more preferably a weak acid inner salt (D), and even more preferably a diphenyliodonium salt containing a phenyl group substituted with a carboxylic acid anion among the weak acid inner salts (D). TIFF2025097318000132.tif97153

[0175] The weak acid inner salt (D) is preferably a diphenyliodonium salt having an iodonium cation to which two phenyl groups are bonded and a carboxylic acid anion substituted for at least one of the two phenyl groups bonded to the iodonium cation, and specifically, examples include salts represented by the following formula.

[0176] TIFF2025097318000133.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 any integer from 0 to 4. When m' is 2 or more, the plurality of R D1 may be the same or different, and when n' is 2 or more, the 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. Examples of the chain hydrocarbon group include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, nonyl group, etc. The alicyclic hydrocarbon group may be monocyclic or polycyclic, and may be saturated or unsaturated. Examples include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclononyl group, cyclododecyl group, etc., norbornyl group, adamantyl group, etc. Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, 1-naphthyl group, 2-naphthyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, 4-propylphenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-t-butylphenyl group, 4-hexylphenyl group, 4-cyclohexylphenyl group, anthryl group, p-adamantylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, biphenyl group, phenanthryl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc. Examples of the group formed by combining these include alkyl-cycloalkyl groups, cycloalkyl-alkyl groups, 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, 6-phenyl-1-hexyl group, etc.). Examples of the alkoxy group include methoxy group, ethoxy group, etc. Examples of the acyl group include acetyl group, propanoyl group, benzoyl group, cyclohexanecarbonyl group, etc. Examples of the acyloxy group include a group in which an oxy group (-O-) is bonded to the above acyl group, etc. Examples of the alkoxycarbonyl group include a group in which a carbonyl group (-CO-) is bonded to the above alkoxy group, etc. Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom, etc. 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 independently preferably any integer from 0 to 2, more preferably 0. When m' is 2 or more, the plurality of R D1 may be the same or different, and when n' is 2 or more, the plurality of R D2 may be the same or different.

[0177] More specifically, the following salts can be mentioned. TIFF2025097318000134.tif72165

[0178] 〈Other components〉 The resist composition of the present invention may contain, if necessary, components other than the above-described components (hereinafter sometimes referred to as "other components (F)"). There are no particular limitations on the other components (F), and additives known in the resist field, such as sensitizers, dissolution inhibitors, surfactants, stabilizers, dyes, etc., can be used.

[0179] 〈Preparation of Resist Composition〉 The resist composition of the present invention can be prepared by mixing compound (I), an acid generator (B), and, if necessary, resin (A), a resin other than resin (A), a solvent (E), a quencher (C), and other components (F). The mixing order is arbitrary and is not particularly limited. The temperature during mixing can be appropriately selected from 10 to 40°C according to the type of resin, etc. and the solubility of the resin, etc. in the solvent (E). The mixing time can be appropriately selected from 0.5 to 24 hours according to the mixing temperature. Note that the mixing means is also not particularly limited, and stirring and mixing, etc. can be used. After mixing the respective components, it is preferable to filter using a filter having a pore size of about 0.003 to 0.2 μm.

[0180] 〈Method for Manufacturing Resist Pattern〉 The method for manufacturing a resist pattern of the present invention (1) A step of applying the resist composition of the present invention onto a substrate, (2) A step of drying the applied composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the exposed composition layer, and (5) A step of developing the heated composition layer. To apply the resist composition onto a substrate, it can be carried out by a commonly used apparatus 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 the surface. Before applying the resist composition, the substrate may be washed, or an antireflection film or the like may be formed on the substrate. By drying the coated composition, the solvent is removed to form a composition layer. Drying is performed, for example, by evaporating the solvent using a heating device such as a hot plate (so-called pre-bake), or by using a decompression device. The heating temperature is preferably 50 to 200 °C, and the heating time is preferably 10 to 180 seconds. Also, the pressure during vacuum drying is preferably about 1 to 1.0×10 5 Pa. The obtained composition layer is usually exposed using an exposure machine. The exposure machine may be an immersion exposure machine. As the exposure light source, those that emit laser light in the ultraviolet region such as a KrF excimer laser (wavelength 248 nm), an ArF excimer laser (wavelength 193 nm), an F2 excimer laser (wavelength 157 nm), those that convert the laser light from a solid laser light source (such as a YAG or semiconductor laser) into harmonic laser light in the far ultraviolet region or vacuum ultraviolet region and emit it, those that irradiate electron beams, extreme ultraviolet light (EUV), etc., various ones can be used. In this specification, irradiating these radiations may be collectively referred to as "exposure". During exposure, usually, exposure is performed through a mask corresponding to the required pattern. When the exposure light source is an electron beam, exposure may be performed by direct drawing without using a mask. The exposed composition layer is heat-treated (so-called post-exposure bake) to promote the deprotection reaction in the acid-labile group. The heating temperature is usually about 50 to 200 °C, preferably about 70 to 150 °C. Chemical treatment (silylation) may be performed to adjust the hydrophilicity or hydrophobicity of the resin on the surface side of the composition after heating. Also, before development, the steps of coating, drying, exposing, and heating the resist composition may be repeated on the exposed composition layer. The heated composition layer is usually developed using a developing solution with a developing device. Examples of the developing method include the dip method, paddle method, spray method, dynamic dispense method, etc. The developing temperature is preferably, for example, 5 to 60 °C, and the developing time is preferably, for example, 5 to 300 seconds. By selecting the type of developing solution as follows, a positive resist pattern or a negative resist pattern can be manufactured. When producing a positive resist pattern from the resist composition of the present invention, an alkaline developer is used as the developer. The alkaline developer may be any of various alkaline aqueous solutions used in this field. For example, aqueous solutions of tetramethylammonium hydroxide, (2-hydroxyethyl)trimethylammonium hydroxide (commonly known as choline), etc. can be mentioned. The alkaline developer may contain a surfactant. After development, it is preferable to wash the resist pattern with ultrapure water and then remove the water remaining on the substrate and the pattern. When producing a negative resist pattern from the resist composition of the present invention, a developer containing an organic solvent (hereinafter sometimes referred to as an "organic-based developer") is used as the developer. Examples of the organic solvent contained in the organic-based developer include ketone solvents such as 2-hexanone and 2-heptanone; glycol ether 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; aromatic hydrocarbon solvents such as anisole, etc. In the organic-based developer, the content of the organic solvent is preferably 90% by mass or more and 100% by mass or less, more preferably 95% by mass or more and 100% by mass or less, and even more preferably substantially only the organic solvent. Among them, as the organic-based developer, a developer containing butyl acetate and / or 2-heptanone is preferable. In the organic-based developer, the total content of butyl acetate and 2-heptanone 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-based developer may contain a surfactant. Also, the organic-based developer may contain a small amount of water. During development, development may be stopped by substituting with a solvent of a different type from the organic-based developer. It is preferable to wash the developed resist pattern with a rinse solution. The rinse solution is not particularly limited as long as it does not dissolve the resist pattern, and a solution containing a general organic solvent can be used, preferably an alcohol solvent or an ester solvent. After washing, it is preferable to remove the rinse solution remaining on the substrate and the pattern.

[0181] <Usage> 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 useful for fine processing of semiconductors.

Examples

[0182] The present invention will be further specifically described with reference to examples. In the examples, “%” and “parts” representing content or usage amount are based on mass unless otherwise specified. The weight average molecular weight is a value determined by gel permeation chromatography under the following conditions. Apparatus: HLC-8120GPC type (manufactured by Tosoh Corporation) Column: TSKgel Multipore H XL -M x 3 + guardcolumn (manufactured by Tosoh Corporation) Eluent: Tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI detector Column temperature: 40 °C Injection volume: 100 μl Molecular weight standard: Standard polystyrene (manufactured by Tosoh Corporation) Also, the structure of the compound was confirmed by measuring the molecular ion peak using mass spectrometry (LC is Agilent 1100 type, MASS is Agilent LC / MSD type). In the following examples, the value of this molecular ion peak is indicated by “MASS”.

[0183] Synthesis Example 1: Synthesis of the compound represented by formula (I-1) 2.78 parts of the compound represented by formula (I-1-a) and 50 parts of acetonitrile were mixed and stirred at 23°C for 30 minutes. To the resulting mixed solution, 1.62 parts of carbonyldiimidazole was added, and the mixture was further stirred at 70°C for 2 hours. To the resulting mixture, 100 parts of chloroform and 50 parts of a 5% aqueous oxalic acid solution were added, and the mixture was stirred at 23°C for 30 minutes. After liquid separation, the organic layer was taken out. To the recovered organic layer, 50 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes. After liquid separation, the organic layer was taken out. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue, and the mixture was stirred and then filtered to obtain 2.66 parts of the compound represented by formula (I-1). MASS: 373.0 [M+H] +

[0184] Synthesis Example 2: Synthesis of the compound represented by formula (I-2) 4.04 parts of the compound represented by formula (I-2-a) and 50 parts of acetonitrile were mixed and stirred at 23°C for 30 minutes. To the resulting mixed solution, 1.62 parts of carbonyldiimidazole was added, and the mixture was further stirred at 70°C for 2 hours. To the resulting mixture, 100 parts of chloroform and 50 parts of a 5% aqueous oxalic acid solution were added, and the mixture was stirred at 23°C for 30 minutes. After liquid separation, the organic layer was taken out. To the recovered organic layer, 50 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes. After liquid separation, the organic layer was taken out. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue, and the mixture was stirred and then filtered to obtain 3.68 parts of the compound represented by formula (I-2). MASS: 498.9 [M+H] +

[0185] Synthesis Example 3: Synthesis of the compound represented by formula (I-3) 2.20 parts of the compound represented by formula (I-3-a) and 50 parts of acetonitrile were mixed and stirred at 23 °C for 30 minutes. To the resulting mixed solution, 1.62 parts of carbonyldiimidazole was added, and the mixture was further stirred at 70 °C for 2 hours. To the resulting mixture, 100 parts of chloroform and 50 parts of 5% aqueous oxalic acid solution were added, and the mixture was stirred at 23 °C for 30 minutes, followed by liquid separation to obtain the organic layer. To the recovered organic layer, 50 parts of ion-exchanged water was added, and the mixture was stirred at 23 °C for 30 minutes, followed by liquid separation to obtain the organic layer. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred, followed by filtration to obtain 3.08 parts of the compound represented by formula (I-3). MASS: 315.0 [M+H] +

[0186] Synthesis Example 4: Synthesis of the compound represented by formula (I-16) 4.12 parts of the compound represented by formula (I-16-a) and 50 parts of chloroform were mixed and stirred at 23 °C for 30 minutes. To the resulting mixed solution, 1.62 parts of carbonyldiimidazole was added, and the mixture was further stirred at 70 °C for 2 hours. To the resulting mixture, 100 parts of chloroform and 50 parts of 5% aqueous oxalic acid solution were added, and the mixture was stirred at 23 °C for 30 minutes, followed by liquid separation to obtain the organic layer. To the recovered organic layer, 50 parts of ion-exchanged water was added, and the mixture was stirred at 23 °C for 30 minutes, followed by liquid separation to obtain the organic layer. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred, followed by filtration to obtain 4.19 parts of the compound represented by formula (I-16). MASS: 507.0 [M+H] +

[0187] Synthesis Example 5: Synthesis of the compound represented by formula (I-18) 6.06 parts of the compound represented by TIFF2025097318000139.tif31107 (I-18-a) and 50 parts of chloroform were mixed and stirred at 23 °C for 30 minutes. 1.62 parts of carbonyldiimidazole was added to the obtained mixed solution, and the mixture was further stirred at 70 °C for 2 hours. 100 parts of chloroform and 50 parts of 5% aqueous oxalic acid solution were added to the obtained mixture, and the mixture was stirred at 23 °C for 30 minutes, followed by liquid separation to obtain the organic layer. 50 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 °C for 30 minutes, followed by liquid separation to obtain the organic layer. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue, stirred, and then filtered to obtain 5.12 parts of the compound represented by formula (I-18). MASS: 700.8 [M+H] +

[0188] Synthesis Example 6: Synthesis of the compound represented by formula (I-8) 3.46 parts of the compound represented by TIFF2025097318000140.tif2889 (I-8-a) and 50 parts of chloroform were mixed and stirred at 23 °C for 30 minutes. 1.62 parts of carbonyldiimidazole was added to the obtained mixed solution, and the mixture was further stirred at 70 °C for 2 hours. 100 parts of chloroform and 50 parts of 5% aqueous oxalic acid solution were added to the obtained mixture, and the mixture was stirred at 23 °C for 30 minutes, followed by liquid separation to obtain the organic layer. 50 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 °C for 30 minutes, followed by liquid separation to obtain the organic layer. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue, stirred, and then filtered to obtain 3.93 parts of the compound represented by formula (I-8). MASS: 440.9 [M+H] +

[0189] Synthesis Example 7: Synthesis of the compound represented by formula (I-13) 1.84 parts of the compound represented by formula (I-13-a) and 50 parts of chloroform were mixed and stirred at 23 °C for 30 minutes. 1.62 parts of carbonyldiimidazole was added to the resulting mixed solution, and the mixture was further stirred at 70 °C for 2 hours. 100 parts of chloroform and 50 parts of 5% aqueous oxalic acid solution were added to the resulting mixture, and the mixture was stirred at 23 °C for 30 minutes, then separated to obtain the organic layer. 50 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 °C for 30 minutes, then separated to obtain the organic layer. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred, and then filtered to obtain 2.25 parts of the compound represented by formula (I-13). MASS: 279.0 [M+H] +

[0190] Synthesis Example 8: Synthesis of the compound represented by formula (I-19) 5.70 parts of the compound represented by formula (I-19-a) and 50 parts of chloroform were mixed and stirred at 23 °C for 30 minutes. 1.62 parts of carbonyldiimidazole was added to the resulting mixed solution, and the mixture was further stirred at 70 °C for 2 hours. 100 parts of chloroform and 50 parts of 5% aqueous oxalic acid solution were added to the resulting mixture, and the mixture was stirred at 23 °C for 30 minutes, then separated to obtain the organic layer. 50 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 °C for 30 minutes, then separated to obtain the organic layer. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred, and then filtered to obtain 5.91 parts of the compound represented by formula (I-19). MASS: 664.8 [M+H] +

[0191] Synthesis Example 9: Synthesis of the compound represented by formula (I-23) 2.30 parts of the compound represented by TIFF2025097318000143.tif2894 formula (I-23-a) and 50 parts of chloroform were mixed and stirred at 23 °C for 30 minutes. To the resulting mixed solution, 1.62 parts of carbonyldiimidazole was added, and further stirred at 70 °C for 2 hours. To the resulting mixture, 100 parts of chloroform and 50 parts of 5% aqueous oxalic acid solution were added and stirred at 23 °C for 30 minutes, then separated to obtain the organic layer. To the recovered organic layer, 50 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, then separated to obtain the organic layer. This water washing operation was repeated 3 times. After concentrating the obtained organic layer, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred, then filtered to obtain 3.03 parts of the compound represented by formula (I-23). MASS: 325.0 [M+H] +

[0192] Synthesis of resin The compounds (monomers) used for the synthesis of resin (A) are shown below. Hereinafter, these compounds are referred to as "monomer (a1-2-6)" etc. according to their formula numbers. TIFF2025097318000144.tif3892

[0193] Synthesis Example 10 [Synthesis of Resin A1] As monomers, monomer (a1-2-6), monomer (a2-1-3), monomer (a3-4-2) and monomer (a1-4-2) were used, and their molar ratio [monomer (a1-2-6): monomer (a2-1-3): monomer (a3-4-2): monomer (a1-4-2)] was mixed at a ratio of 55:3:15:27. Further, 1.5 times the mass of methyl isobutyl ketone with respect to the total mass of all monomers was mixed into this monomer mixture. To the obtained mixture, azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1.2 mol% and 3.6 mol%, respectively, with respect to the total monomer amount, and these were heated at 73 °C for about 5 hours. Thereafter, an aqueous solution of p-toluenesulfonic acid (2.5 wt%) 2.0 times the mass with respect to the total mass of the total monomer amount was added to the polymerization reaction solution, and after stirring for 12 hours, liquid separation was performed. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, and the resin was obtained by filtration and recovery, and resin A1 having a weight average molecular weight of about 5.5×10 3 was obtained with a yield of 88%. This resin A1 has the following structural units. TIFF2025097318000145.tif38127

[0194] <Preparation of Resist Composition> As shown in Table 1, the following components were mixed, and the obtained mixture was filtered through a fluororesin filter with a pore size of 0.2 μm to prepare a resist composition.

Table 1

[0195] <Resin> A1: Resin A1 <Acid Generator (B)> B1-43: Salt represented by formula (B1-43) (synthesized according to the examples of JP-A-2016-47815) TIFF2025097318000147.tif44115<Compound (I), etc.> I-1: Compound represented by formula (I-1) I-2: Compound represented by formula (I-2) I-3: Compound represented by formula (I-3) I-8: Compound represented by formula (I-8) I-13: Compound represented by formula (I-13) I-16: Compound represented by formula (I-16) I-18: Compound represented by formula (I-18) I-19: Compound represented by formula (I-19) I-23: Compound represented by formula (I-23) <Quencher (C)> IX-1: Synthesized by the method described in JP-A-2012-008553 IX-2: Synthesized by the method described in JP-A-2012-008553 JPEG2025097318000148.jpg2367 <Solvent> 400 parts of propylene glycol monomethyl ether acetate 100 parts of propylene glycol monomethyl ether 5 parts of γ-butyrolactone

[0196] (Electron beam exposure evaluation of resist composition: Butyl acetate development) A 6-inch silicon wafer was treated on a direct hot plate with hexamethyldisilazane at 90 °C for 60 seconds. The resist composition was spin-coated on this silicon wafer so that the film thickness of the composition layer was 0.04 μm. Then, it was prebaked on a direct hot plate at the temperature shown in the "PB" column of Table 1 for 60 seconds to form a composition layer. A line and space pattern was directly drawn on the composition layer formed on the wafer using an electron beam lithography machine ["HL-800D 50 keV" manufactured by Hitachi, Ltd.] while changing the exposure dose stepwise. After exposure, post-exposure baking was performed on a hot plate at the temperature shown in the "PEB" column of Table 1 for 60 seconds. Next, the composition layer on this silicon wafer was developed at 23 °C for 20 seconds by the dynamic dispense method using butyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) as a developer to obtain a resist pattern. The obtained resist pattern (line and space pattern) was observed with a scanning electron microscope, and the exposure dose at which the line width and space width of the 60 nm line and space pattern were 1:1 was defined as the effective sensitivity.

[0197] Line edge roughness evaluation (LER): The line edge roughness was determined by measuring the amplitude of the unevenness on the side wall surface of the resist pattern fabricated at the effective sensitivity with a scanning electron microscope. The results are shown in Table 2.

Table 2

Industrial Applicability

[0198] Since the resist composition of the present invention is excellent in the line edge roughness (LER) of the obtained resist pattern, it is suitable for semiconductor microfabrication and is extremely useful industrially.

Claims

1. A resist composition comprising a compound represented by formula (I) and an acid generator. [In formula (I), X ０ represents a hydrocarbon group having 1 to 72 carbon atoms and containing a halogen atom, and the —CH 2 - is -O-, -S-, -CO- or -SO ２ The hydrocarbon group may be substituted with -, and the hydrocarbon group may have a substituent other than a halogen atom. R ｃ１ , R ｃ２ and R ｃ３ each independently represents a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 48 carbon atoms, the hydrocarbon group optionally having a substituent, ２ - is -O-, -CO-, -S- or -SO ２ May be replaced with -. nc1 represents an integer of 1 to 6. When nc1 is 2 or more, the groups in the parentheses may be the same or different.]

2. X ０ a group formed by combining two or more selected from an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, and an aromatic hydrocarbon group having 6 to 36 carbon atoms (the alicyclic hydrocarbon group and the aromatic hydrocarbon group have a fluorine atom, an iodine atom, or a fluorinated alkyl group having 1 to 4 carbon atoms, and may have a hydroxy group, the chain hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group, and the -CH contained in the alicyclic hydrocarbon group and the chain hydrocarbon group ２ 2. The resist composition according to claim 1, wherein - may be replaced by -O- or -CO-.

3. 2. The resist composition according to claim 1, wherein the acid generator is a salt represented by formula (B1). [In formula (B1), L b1 represents a single bond or a (nb1+1)-valent hydrocarbon group which may have a substituent, and —CH 2 - is -O-, -S-, -CO- or -SO 2 It may be replaced with -. L b2 represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the —CH 2 - is -O-, -S-, -CO- or -SO 2 It may be replaced with -. Y b1 represents a methyl group which may have a substituent or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -SO 2 It may be replaced by --or --CO--. nb1 represents an integer of 1 to 6. When nb1 is 2 or more, the groups in the parentheses may be the same or different. Z ＋ represents an organic cation.

4. The composition further comprises a resin, The resist composition according to claim 1, which comprises a structural unit represented by formula (a2-A): [In formula (a2-A), R ａ２ represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R ａ２７ represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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 ａ２１ represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and the —CH ２ - is -O-, -CO- or -NR ａ２８ May be replaced with -. R ａ２８ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X ａ２ represents a single bond or a carbonyl group. nA2 represents an integer of 1 to 5, and when nA2 is 2 or more, the groups in the parentheses may be the same or different. na21 represents an integer of 0 to 4, and when na21 is 2 or more, a plurality of R ａ２７ may be the same or different from each other. mc represents an integer of 0 to 2.

5. the resin further comprises structural units having acid labile groups; The resist composition according to claim 4, wherein the structural unit having an acid labile group includes 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), a structural unit represented by formula (a1-2), a structural unit represented by formula (a1-4), a structural unit represented by formula (a1-5), and a structural unit represented by formula (a1-6). [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 combination thereof, and the alkyl group, alicyclic hydrocarbon group and aromatic hydrocarbon group may contain a halogen atom. 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, and the alkyl group, alkenyl group, alicyclic hydrocarbon group and aromatic hydrocarbon group may have a halogen atom. m1′ represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1' represents an integer of 0 to 3. [In formula (a1-4), R ａ１ represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R ａ１７ represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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 ａ１１ represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and the —CH ２ - is -O-, -CO- or -NR ａ１８ May be replaced with -. R ａ１８ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X ａ１ represents a single bond or a carbonyl group. 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 a divalent hydrocarbon group having 2 to 20 carbon atoms together with the -C-O- to which they are bonded, and the hydrocarbon group and the -CH 2 - may be replaced by -O- or -S-. na1 represents an integer of 1 to 5, and when na1 is 2 or more, the groups in the parentheses may be the same or different. na11 represents an integer of 0 to 4, and when na11 is 2 or more, a plurality of R ａ１７ may be the same or different from each other. mc represents an integer of 0 to 2. [In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. Z a1 is a single bond or *-(CH 2 ) 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.] [In formula (a1-6), R a61 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a6２ , R a63 and R a6４ each independently represents an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, or R a6２ and R a63 are bonded to each other to form, together with the carbon atoms to which they are attached, a ring having 3 to 20 carbon atoms. X a61 is a single bond, -CO-O-* or -CO-NR a65 - represents *, * represents a bonding site with Ar, R a65 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 is a single bond, *-O-L a61 - or *-CO-OL a62 -, * represents a bonding site with Ar, L a61 and L a62 each independently represents an alkanediyl group having 1 to 4 carbon atoms. Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.]

6. (1) A step of applying the resist composition according to any one of claims 1 to 5 onto a substrate; (2) A step of drying the applied resist 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 the steps of:

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