Phenol generator, phenol salt, resist composition, and method for producing resist pattern

Abstract

To provide a phenol generator, a resist composition and the like which allow a resist pattern having good line edge roughness to be produced.SOLUTION: The phenol generator contains a phenol salt represented by formula (I) [where R4 represents a halogen atom or a hydrocarbon group, the hydrocarbon group may have a substituent, -CH2- contained in the hydrocarbon group may be substituted with -O-, -CO-, -S- or -SO2-, and the hydrocarbon group may contain a phenoxy anion; R5 represents an alkoxyalkyl group or a hydroxyalkyl group; m4 represents an integer of 0-4 and m5 represents an integer of 1-4, provided that 1≤m4+m5≤5 is satisfied; m2 represents an integer of 1-8; and Z+ represents an organic cation].SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] Patent Document 1 describes a resist composition containing a phenol salt represented by the following formula as a phenol generator. TIFF2025105524000001.tif2837

[0003] Patent Document 2 describes a resist composition containing a phenol salt represented by the following formula as a phenol generator. TIFF2025105524000002.tif3048

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] The present invention provides a carboxylate that forms a resist pattern with better line edge roughness (LER) than a resist pattern formed by a resist composition containing the above carboxylate.

Means for Solving the Problems

[0006] The present invention includes the following inventions. [1] A phenol generator containing a phenol salt represented by formula (I). TIFF2025105524000003.tif24116[In formula (I), R 4 represents a halogen atom or a hydrocarbon group having 1 to 72 carbon atoms, and the hydrocarbon group is *-O - (* represents the bonding site with R 4 .) or may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-, -S-, -SO2-. R 5 represents an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms. m4 represents any integer from 0 to 4, and when m4 is 2 or more, a plurality of R 4 may be the same as or different from each other. m5 represents any integer from 1 to 4, and when m5 is 2 or more, a plurality of R 5 may be the same as or different from each other. However, 1 ≦ m4 + m5 ≦ 5. Z + represents an organic cation. m2 represents any integer from 1 to 8, and when m2 is 2 or more, a plurality of Z + may be the same as or different from each other.] [2] When m4 is an integer of 1 or more, and one of the one or more R 4 is an alkyl group having 1 to 6 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-, -S-, -SO2-), the phenol generator according to [1]. [3] When m4 is an integer of 1 or more, and one of the one or more R 4 is a hydrocarbon group containing a benzene ring bonded to at least one group selected from *-O - , a hydroxy group, an alkoxyalkyl group having 2 to 6 carbon atoms, and a hydroxyalkyl group having 1 to 6 carbon atoms, and the benzene ring may have a substituent other than *-O - , a hydroxy group, an alkoxy group having 2 to 6 carbon atoms, and a hydroxyalkyl group having 1 to 6 carbon atoms, the phenol generator according to [1] or [2]. [4] m4 is an integer of 1 or more, 1 or more R 4 One of them is the phenol-generating agent according to [3], which is a group represented by any one of formula (R4-1) to formula (R4-5). TIFF2025105524000004.tif93162 [In formula (R4-1) to formula (R4-5), R 4A represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. R 5A represents an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms. m4A, m4B, and m4C each independently represent an integer of any one of 0 to 4. When m4A + m4B + m4C is 2 or more, a plurality of R 4A may be the same as or different from each other. m5A, m5B, and m5C each independently represent an integer of 1 to 4, satisfying 1 ≤ m4A + m5A ≤ 4, 1 ≤ m4B + m5B ≤ 4, and 1 ≤ m4C + m5C ≤ 4, and a plurality of R 5A may be the same as or different from each other. R 6A and R 6B each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 7 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. m7 represents an integer of any one of 0 to 4. L 1 , L 1A and L 1B each independently represent a single bond, a methylene group, a methylmethylene group, a dimethylmethylene group, a carbonyl group, or a sulfonyl group. X 1 represents a hydroxy group or *-O - represents. * represents the bonding site with the benzene ring. The total number of carbon atoms contained in each group represented by formula (R4-1) to formula (R4-5) does not exceed 60.] [5][1] A resist composition containing a phenol generator according to any one of [1] to [4] and an acid generator other than the phenol generator. [6] The resist composition according to [5], wherein the acid generator contains a salt represented by formula (B1) or a salt represented by formula (B3). TIFF2025105524000005.tif1396[In formula (B1), L b1 represents a single bond or an (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 of any one of 1 to 6. When nb1 is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. Z1 + represents an organic cation. ] TIFF2025105524000006.tif1293[In formula (B3), 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 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-, and two -SO2-Lb2’ -Y b1’ may combine together to form a ring containing A 1 if possible. nb5 represents 2 or 3. When nb5 is 2, A 1 represents a nitrogen atom, and when nb5 is 3, A 1 represents a carbon atom. The groups within multiple parentheses may be the same or different from each other. Z2 + represents an organic cation.] [7] Further, a resist composition according to [5] or [6], which contains a compound having a phenolic hydroxyl group or a benzoic acid carboxy group and / or a compound in which the hydroxyl group of the phenolic hydroxyl group or the carboxy group of the benzoic acid carboxy group is protected with an acid-labile group. [8] The resist composition according to [7], wherein the compound is a resin, and the resin contains a resin containing a structural unit represented by formula (a2-A) or a structural unit represented by formula (a1-4). TIFF2025105524000007.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 any integer from 1 to 5. When nA2 is 2 or more, the groups within the plurality of parentheses may be the same as or different from each other. na21 represents any 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 any integer from 0 to 2. TIFF2025105524000008.tif31118 [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, and 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. When na1 is 2 or more, the groups within the plurality of parentheses may be the same as or different from each other. na11 represents any integer from 0 to 4. When na11 is 2 or more, the plurality of Rs a17 may be the same as or different from each other. mc represents any integer from 0 to 2.] [9] The resin further contains a structural unit having an acid-labile group other than the structural unit represented by formula (a1-4), and the structural unit having an acid-labile group other than the structural unit represented by formula (a1-4) is at least one selected from the group consisting of the structural unit represented by formula (a1-0), the structural unit represented by formula (a1-1), the structural unit represented by formula (a1-2), the structural unit represented by formula (a1-5), and the structural unit represented by formula (a1-6). The resist composition according to [8]. TIFF2025105524000009.tif43144 [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 any integer from 1 to 7, and * represents the bonding site with -CO-. R a01 、R a4 and R a5 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 、R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, and the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. R a6 and R a7each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. m1’ represents any integer from 0 to 14. n1 represents any integer from 0 to 10. n1’ represents any integer from 0 to 3. TIFF2025105524000010.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 represents a single bond or *-(CH2) h3 -CO-L 54 -, h3 represents any integer from 1 to 4, and * represents the bonding site with 51 L. L 51 L 52 L 53 and L 54 each independently represents -O- or -S-. s1 represents any integer from 1 to 3. s1’ represents any integer from 0 to 3. TIFF2025105524000011.tif3681[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 a62 R a63 and R X a61represents a single bond, -CO-O-* or -CO-NR a65 -*, where * represents a bond to 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 -, where * represents a bond to Ar, and L a61 and L a62 each independently represent 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.

[10] A step of applying the resist composition according to any one of [5] to [9] 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, which is a method for manufacturing a resist pattern.

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

[12] m4 is an integer of 1 or more, One of the one or more R 4 is an alkyl group having 1 to 6 carbon atoms (where -CH2- contained in the alkyl group may be replaced by -O- or -CO-, -S-, -SO2-). The phenol salt according to

[11] .

[13] m4 is an integer of 1 or more, One of the one or more R 4 is a hydrocarbon group containing a benzene ring bonded to at least one group selected from *-O - , a hydroxy group, an alkoxyalkyl group having 2 to 6 carbon atoms, and a hydroxyalkyl group having 1 to 6 carbon atoms, and the benzene ring may have a substituent other than *-O - , a hydroxy group, an alkoxy group having 2 to 6 carbon atoms, and a hydroxyalkyl group having 1 to 6 carbon atoms. The phenol salt according to

[11] or

[12] .

[14] m4 is an integer of 1 or more, One of the one or more R4 One of them is the phenol salt described in

[13] , which is a group represented by any of the above-described formulas (R4-1) to (R4-5).

Advantages of the Invention

[0007] By using a resist composition containing a phenol generator containing the phenol salt of the present invention, a resist pattern can be produced with good line edge roughness (LER).

Embodiments for Carrying Out the Invention

[0008] In this specification, the term “(meth)acrylic monomer” means “at least one of acrylic monomers and methacrylic monomers”. Notations such as “(meth)acrylate” and “(meth)acrylic acid” also represent the same meaning. In the groups described in this specification, those that can take both a linear structure and a branched structure may be either of them. When -CH2- contained in a hydrocarbon group or the like is replaced by -O-, -S-, -CO-, -SO-, -NR X -(X is an arbitrary symbol) or -SO2-, the same examples are applied to each group, and the number of carbon atoms before replacement is defined as the number of carbon atoms of the hydrocarbon group or 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” means that the polymerizable C=C bond contained in the molecule becomes a -C-C- group (single bond) by polymerization. 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 is eliminated to form a hydrophilic group (e.g., a hydroxy group or a carboxy group). The base-labile group means a group that, when contacted with a base (e.g., trimethylamine, tetramethylammonium hydroxide, etc.), the leaving group is eliminated to form a hydrophilic group (e.g., a carboxy group or a hydroxy group). 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, etc. 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.

[0009] [Phenol salt represented by formula (I)] The present invention relates to a phenol salt represented by formula (I) (hereinafter sometimes referred to as "phenol salt (I)" or "salt (I)"). Among the salts (I), the side having a negative charge may be referred to as "anion (I)", and the side having a positive charge may be referred to as "cation (I)". TIFF2025105524000012.tif24116 [In formula (I), all symbols have the same meanings as described above.]

[0010] In formula (I), R 4 Examples of the halogen atom of R include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like. R 4 Examples of the hydrocarbon group having 1 to 72 carbon atoms of R include a chain hydrocarbon group such as an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these. The alkyl group is a linear or branched alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 9, still more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups represented below. The bonding site can be at any position. TIFF2025105524000013.tif46168Specifically, examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, etc. Examples of the polycyclic alicyclic hydrocarbon group include cycloalkyl groups such as decahydronaphthyl group, adamantyl group, norbornyl group, spirocyclohexane-1,2’-cyclopentane, spiroadamantane-2,3’-cyclopentane group, etc., and spiro rings having a cycloalkyl group bonded to a norbornyl group or an adamantyl group by spiro bonding respectively. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. Examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, biphenyl group, anthryl group, phenanthryl group, binaphthyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10.

[0011] Examples of the group formed by combination include a group formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, aromatic hydrocarbon group - alkane diyl group - *, alkyl group - aromatic hydrocarbon group - *, and -CH2- contained in the alkane diyl group and the alkyl group may be replaced by -O-, -CO-, -S- or -SO2-), a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group - alkane diyl group - *, alkyl group - alicyclic hydrocarbon group - *, and -CH2- contained in the alkane diyl group and the alkyl group may be replaced by -O-, -CO-, -S- or -SO2-), and a group formed by combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, aromatic hydrocarbon group - alicyclic hydrocarbon group - *, alicyclic hydrocarbon group - aromatic hydrocarbon group - *). * represents a bonding site. Examples of the aromatic hydrocarbon group - alkane diyl group - * include aralkyl groups such as benzyl group and phenethyl group. Examples of the alkyl group - aromatic hydrocarbon group - * include tolyl group, xylyl group, cumenyl group, etc. Examples of the alicyclic hydrocarbon group-alkanediyl group-* include cycloalkylalkyl groups such as cyclohexylmethyl group, cyclohexylethyl group, 1-(adamantan-1-yl)methyl group, 1-(adamantan-1-yl)-1-methylethyl group, and the like. Examples of the alkyl group-alicyclic hydrocarbon group-* include cycloalkyl groups having an alkyl group such as methylcyclohexyl group, dimethylcyclohexyl group, 2-alkyladamantan-2-yl group, and the like. Examples of the aromatic hydrocarbon group-alicyclic hydrocarbon group-* include phenylcyclohexyl group and the like. Examples of the alicyclic hydrocarbon group-aromatic hydrocarbon group-* include cyclohexylphenyl group and the like. In the combination, two or more alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined with each other. Also, any of these groups may be bonded to the benzene ring.

[0012] R 4 When -CH2- contained in the hydrocarbon group represented by [R] is replaced by -O-, -CO-, -S- or -SO2-, the carbon number before replacement is taken as the total carbon number of the haloalkyl group or the hydrocarbon group. Also, the number may be one or two or more. 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 thiol group (a group in which -CH2- contained in a methyl group is replaced by -S-), a carboxy group (a group in which -CH2-CH2- contained in an ethyl group is replaced by -O-CO-), an alkoxy group (a group in which -CH2- at any position contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in an alkyl group is replaced by -O-CO-), 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 alkoxycarbonyloxy group (a group in which -CH2-CH2-CH2- at any position contained in an alkyl group is replaced by -O-CO-O-), an alkylthio group (a group in which -CH2- at any position contained in an alkyl group is replaced by -S-), an alkylsulfonyl group (a group in which -CH2- at any position contained in an alkyl group is replaced by -SO2-), 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 alkanediylthio group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -S-),An alkanediylsulfonyl group (a group in which any -CH2- at an arbitrary position in the alkanediyl group is replaced by -SO2-), a cycloalkoxy group, a cycloalkylalkoxy group, an aromatic hydrocarbon group-carbonyl-oxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, a haloalkoxy group (a group in which any -CH2- at an arbitrary position in the haloalkyl group is replaced by -O-), a haloalkoxycarbonyl group (a group in which any -CH2-CH2- at an arbitrary position in the haloalkyl group is replaced by -O-CO-), a haloalkylcarbonyl group (a group in which any -CH2- at an arbitrary position in the haloalkyl group is replaced by -CO-), a haloalkylcarbonyloxy group (a group in which any -CH2-CH2- at an arbitrary position in the haloalkyl group is replaced by -CO-O-), a group formed by combining two or more of these groups, etc. can be mentioned. Examples of the alkoxy group include alkoxy groups having 1 to 71 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group and the like. The number of carbon atoms of the alkoxy group may be 1 to 48, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even 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 71 carbon atoms, such as butoxycarbonyloxy group and the like. The carbon number of the alkoxycarbonyl group may be 2 to 48, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The carbon number of the alkylcarbonyl group may be 2 to 48, preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The carbon numbers of the alkylcarbonyloxy group and the alkoxycarbonyloxy group may each be 2 to 48, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 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 carbon number of the alkylthio group may be 1 to 48, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 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 number of carbon atoms of the alkylsulfonyl group may be 1 to 48, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkanediyl-oxy group include alkanediyl-oxy groups having 1 to 71 carbon atoms, such as methyleneoxy group, ethyleneoxy group, propanediyl-oxy group, butanediyl-oxy group, pentanediyl-oxy group and the like. The number of carbon atoms of the alkanediyl-oxy group may be 1 to 48, preferably 1 to 11, more preferably 1 to 6, still 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 propane diyl oxycarbonyl group, and a butane diyl 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 propane diyl carbonyl group, a butane diyl carbonyl group, and a pentane diyl carbonyl group. Examples of the alkanediyl carbonyl oxy group include alkanediyl carbonyl oxy groups having 2 to 71 carbon atoms, such as a methylene carbonyl oxy group, an ethylene carbonyl oxy group, a propane diyl carbonyl oxy group, and a butane diyl carbonyl oxy group. The number of carbon atoms in the alkanediyl oxycarbonyl group may be 2 to 48, preferably 2 to 11, more preferably 2 to 6, still 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 48, preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyl carbonyl oxy group may be 2 to 48, preferably 2 to 11, more preferably 2 to 6, still 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 48, preferably 1 to 11, more preferably 1 to 6, still 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 methylenesulfonyl group, ethylenesulfonyl group, propylenesulfonyl group and the like. The number of carbon atoms of the alkanediylsulfonyl group may be 1 to 48, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 71 carbon atoms, such as cyclohexyloxy group and the like. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 71 carbon atoms, such as cyclohexylmethoxy group and the like. Examples of the aromatic hydrocarbon group-carbonyloxy group include aromatic hydrocarbon group-carbonyloxy groups having 7 to 71 carbon atoms, such as benzoyloxy group and the like. Examples of the aromatic hydrocarbon group-carbonyl group include aromatic hydrocarbon group-carbonyl groups having 7 to 72 carbon atoms, such as benzoyl group and the like. Examples of the aromatic hydrocarbon group-oxy group include aromatic hydrocarbon group-oxy groups having 6 to 72 carbon atoms, such as phenyloxy group and the like.

[0013] In addition, examples of the group in which -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -S- or -CO- include the groups represented below. The bonding site can be at any position. TIFF2025105524000014.tif46168 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 and the like. The bonding site can be at any position. TIFF2025105524000015.tif26164

[0014] R 4 Examples of the substituent that the hydrocarbon group of - (* represents the bonding site with R 4 ) may have include -O 4When it is a group combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group with an alkyl group, the alkyl group can be a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. Also, R 4 In the alkyl group contained in R, when -CH2- contained in the alkyl group is replaced by -O-, -CO-, -S- or -SO2-, the hydrocarbon group of R 4 can substantially have substituents such as a hydroxy group, a hydroxyalkyl group, a carboxy group, an alkoxy group, an alkoxyalkyl group, an alkylcarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, a thiol group, a sulfonyl group and the like. Examples of the halogen atom include the same groups as those described above. R 4 The number of substituents that the hydrocarbon group of R may have may be one or a plurality of two or more. In particular, the hydrocarbon group of R 4 may have one or more phenoxy anions. R 4 is a halogen atom, an alkyl group having 1 to 6 carbon atoms (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-), a haloalkyl group having 1 to 4 carbon atoms or *-O - , a hydroxy group, an alkoxyalkyl group having 2 to 6 carbon atoms and a benzene ring bonded to at least one group selected from hydroxyalkyl groups having 1 to 6 carbon atoms (the benzene ring may have substituents other than a phenoxy anion, a hydroxy group, an alkoxy group having 2 to 6 carbon atoms and a hydroxyalkyl group having 1 to 6 carbon atoms).), and preferably a hydrocarbon group containing an iodine atom, a fluorine atom, a hydroxy group, an alkoxyalkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, a carboxy group, a fluorinated alkyl group having 1 to 4 carbon atoms or *-O -Or a benzene ring bonded to a hydroxy group and also bonded to an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms (the benzene ring may have substituents other than a phenoxy anion, a hydroxy group, an alkoxy group having 2 to 6 carbon atoms, and a hydroxyalkyl group having 1 to 6 carbon atoms). It is more preferably a hydrocarbon group containing the same, and more preferably an iodine atom, a fluorine atom, a hydroxy group, a methyl group, a methoxymethyl group, a hydroxymethyl group, a carboxy group, a perfluoroalkyl group having 1 to 3 carbon atoms, or a group represented by any of formula (R4-1) to formula (R4-5), and still more preferably an iodine atom, a fluorine atom, a hydroxy group, a methyl group, a methoxymethyl group, a hydroxymethyl group, or a group represented by any of formula (R4-1) to formula (R4-5). TIFF2025105524000016.tif93162[In formula (R4-1) to formula (R4-5), all symbols have the same meanings as described above.] In formula (R4-1) to formula (R4-5), R 6A and R 6B are each preferably independently a hydrogen atom. L 1 is preferably a single bond. m2 is preferably represented by an integer of 1 to 4.

[0015] R 5 Examples of the alkoxyalkyl group having 1 to 6 carbon atoms or the hydroxyalkyl group having 1 to 6 carbon atoms of R include a group formed by combining the above-described alkoxy group and alkyl group or a group formed by combining a hydroxy group and an alkyl group. R 5 is preferably an alkoxyalkyl group having 2 to 4 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms, and more preferably a methoxymethyl group or a hydroxymethyl group. m4 is preferably represented by any integer of 0 to 3, and more preferably represented by any integer of 0, 1, or 2. m5 is preferably any integer represented by 1 to 3, and more preferably any integer of 2 or 3.

[0016] As the anion (I), for example, it is more preferably a group represented by any of the formulas (I-A) to (I-F). TIFF2025105524000017.tif75167[In the formulas (I-A) to (I-F), L 1 , L 1A , L 1B , R 6 , R 7 , m7, and X 1 represent the same meaning as in the formulas (R4-1) to (R4-5). A plurality of R 5B each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms, and at least one R 5B represents an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms. A plurality of R 5C each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms, and at least one R 5C represents an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms. X 1 represents a hydroxy group or -O - .

[0017] Examples of the anion (I) include the following anions. Among them, anions represented by the formulas (Ia-1), (Ia-2), (Ia-4), (Ia-9), (Ia-10), (Ia-13), (Ia-14), (Ia-17), (Ia-18), (Ia-21), and (Ia-22) are preferred. TIFF2025105524000018.tif249160

[0018] TIFF2025105524000019.tif144165

[0019] [[Cation (I)]] Z in formula (I) + Examples of the organic cation include organic onium cations, organic sulfonium cations, organic iodonium cations, organic ammonium cations, benzothiazolium cations, and organic phosphonium cations. Among these, organic sulfonium cations and organic iodonium cations are preferred, and arylsulfonium cations are more preferred. Specifically, cations represented by any of formula (b2-1) to formula (b2-5) (hereinafter may be referred to as "cation (b2-1)" etc. according to the formula number) are included. TIFF2025105524000020.tif83159[In formula (b2-1) to formula (b2-5), R b4 ~R b6 each independently represents a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms. The hydrogen atoms contained in the linear 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 and may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R b7 and R b8Each 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, a plurality of R b7 may be the same or different, and when n2 is 2 or more, a plurality of R b8 may be the same or different. R b9 and R b10 each independently represent a chain hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and -CH2- contained in the ring may be replaced by -O-, -S-, or -CO-. R b11 represents a hydrogen atom, a chain hydrocarbon group having 1 to 36 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. R b12 represents a chain hydrocarbon group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and 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 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 by -O-, -S-, or -CO-. R b13 ~R b18 and R b21 ~R b26 each independently represent 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. Rb13 and R b14 and R b21 and R b22 and R 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 by -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 an integer from 0 to 5. q2 and r2 each independently represent an integer from 0 to 4. u2 represents 0 or 1. When o2 is 2 or more, a plurality of R b13 are the same or different, when p2 is 2 or more, a plurality of R b14 are the same or different, when q2 is 2 or more, a plurality of R b15 are the same or different, when r2 is 2 or more, a plurality of R b16 are the same or different, when s2 is 2 or more, a plurality of R b17 are the same or different, when t2 is 2 or more, a plurality of R b18 are the same or different. u3 represents an integer from 1 to 3 and satisfies 1 ≦ u3 + q23 ≦ 5. u4 and u5 each independently represent an 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 an integer from 0 to 4. When u3, u4, and u5 are each 2 or more, the groups in parentheses are each the same or different. When o21, p22, q23, r24, t25, and s26 are each 2 or more, a plurality of R b21 ~R b26 are each the same or different. When u3, u4, and u5 are each 2 or more, the groups in parentheses are each the same or different. When u2 is 0, at least one of o2, p2, q2, and r2 is 1 or more, and b13 ~R b16 it is preferable that at least one of them is a halogen atom. When u2 is 1, at least one of o2, p2, s2, t2, q2, and r2 is 1 or more, and b13 ~R b18 it is preferable that at least one of them is 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, b16 it is preferable that R is a halogen atom.

[0020] 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, the chain hydrocarbon group of b9 ~R b12 is preferably C1-C12. 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 group. TIFF2025105524000021.tif11157In particular, the b9 ~R b12 alicyclic hydrocarbon group is preferably C3-C18, more preferably C4-C12.

[0021] Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include a methylcyclohexyl group, a dimethylcyclohexyl group, a 2-methyladamantan-2-yl group, a 2-ethyladamantan-2-yl group, a 2-isopropyladamantan-2-yl group, a methylnorbornil group, an isobornyl group, and the like. 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 a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, and a perfluorobutyl group. The number of carbon atoms of the alkyl fluoride group is preferably 1 to 9, more preferably 1 to 6, and still more preferably 1 to 4.

[0022] Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a biphenyl group, a naphthyl group, and a 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 a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a p-ethylphenyl group, a p-tert-butylphenyl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group, and examples of the aromatic hydrocarbon group having an alicyclic hydrocarbon group include a p-cyclohexylphenyl group and a p-adamantylphenyl group. 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 a p-methoxyphenyl group. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as a benzyl group, a phenethyl group, a phenylpropyl group, a trityl group, a naphthylmethyl group, and a naphthylethyl group.

[0023] 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, a dodecyloxy group, and the like. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, a butyryl group, and the like. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. Examples of the alkylcarbonyloxy group include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, an isopropylcarbonyloxy group, a butylcarbonyloxy group, a sec-butylcarbonyloxy group, a tert-butylcarbonyloxy group, a pentylcarbonyloxy group, a hexylcarbonyloxy group, an octylcarbonyloxy group, a 2-ethylhexylcarbonyloxy group, and the like.

[0024] R b4 and R b5 The ring formed by R and R bonding to each other together with the sulfur atom to which they are bonded may be any of a monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated ring. Examples of this ring include rings having 3 to 18 carbon atoms, preferably rings having 4 to 18 carbon atoms. Further, examples of the ring containing a sulfur atom include 3-membered to 12-membered rings, preferably 3-membered to 7-membered rings. For example, the following rings can be mentioned. * represents a bonding site. TIFF2025105524000022.tif24142

[0025] R b9 and R b10 The ring formed by R and R together may be any of a monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated ring. Examples of this ring include 3-membered to 12-membered rings, preferably 3-membered to 7-membered rings. For example, a thiolan-1-ium ring (tetrahydrothiophenium ring), a thian-1-ium ring, a 1,4-oxathian-4-ium ring, and the like can be mentioned. R b11 and R b12The ring formed by combining them may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. This ring includes 3-membered rings to 12-membered rings, preferably 3-membered rings to 7-membered rings. Examples include oxocycloheptane ring, oxocyclohexane ring, oxonorbornane ring, oxoadamantane ring, etc. R b27 ~R b29 Examples of the group containing an acid-labile group of ~R c30 include -R c30 , -CO-O-R c10 or -L c30 -CO-O-R c10 (where L c30 represents an alkanediyl group having 1 to 6 carbon atoms, and R R b27 ~R b29 The acid-labile groups of include the following group (1) and / or group (2).

[0026] 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. TIFF2025105524000023.tif149164 Examples of cation (b2-2) include the following cations. TIFF2025105524000024.tif14136 Examples of cation (b2-3) include the following cations. TIFF2025105524000025.tif21129 Examples of cation (b2-4) include the following cations. TIFF2025105524000026.tif123163 Examples of cation (b2-5) include the following cations. TIFF2025105524000027.tif115157

[0027] The phenolic salt (I) is a combination of the above-mentioned anion and the above-mentioned organic cation, and these can be arbitrarily combined. As the salt (I), preferably, an anion represented by any of formula (Ia-1), formula (Ia-2), formula (Ia-4), formula (Ia-9), formula (Ia-10), formula (Ia-13), formula (Ia-14), formula (Ia-17), formula (Ia-18), formula (Ia-21), formula (Ia-22), and a combination with cation (b2-1), cation (b2-2), cation (b2-3), cation (b2-4) or cation (b2-5) are mentioned.

[0028] Specific examples of the phenolic salt (I) include salts obtained by arbitrarily combining the above-mentioned cations and anions. Specific examples of the salt (I) are shown in the following table. In the following table, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation, and "~" indicates that each of the phenolic salt (I) and the anion (I) corresponds. For example, the phenolic salt (I-1) is a salt composed of an anion represented by formula (I-a-1) and a cation represented by formula (b2-c-1), the salt (I-2) is a salt composed of an anion represented by formula (I-a-2) and a cation represented by formula (b2-c-1), and the phenolic salt (I-31) is a salt composed of an anion represented by formula (I-a-1) and a cation represented by formula (b2-c-10). Examples of the phenolic salt (I) include the salts described in Table 1. In the following table, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation. For example, the phenolic salt (I-1) means a salt composed of an anion represented by formula (Ia-1) and a cation represented by formula (b2-c-1), and represents the salts shown below. TIFF2025105524000028.tif3363

Table 1

[0029] Among them, as the phenol salt (I), a salt combining an anion represented by any of formula (Ia-1), formula (Ia-2), formula (Ia-4), formula (Ia-9), formula (Ia-10), formula (Ia-13), formula (Ia-14), formula (Ia-17), formula (Ia-18), formula (Ia-21), formula (Ia-22) and a cation represented by any of formula (b2-c-1), formula (b2-c-10), formula (b2-c-13), formula (b2-c-14), formula (b2-c-18) to formula (b2-c-20), formula (b2-c-27), formula (b2-c-30), formula (b2-c-31), formula (b2-c-50) to formula (b2-c-79) is preferred.

[0030] <Method for producing phenol salt (I)> The salt (I) can be obtained by reacting a compound represented by formula (I-a) with sodium hydroxide in a solvent and then further reacting with a salt represented by formula (I-b). TIFF2025105524000030.tif27126 (In the formula, all the symbols have the same meanings as described above.) Examples of the solvent include acetonitrile, chloroform, tetrahydrofuran, and water. The reaction is usually carried out in a temperature range of 15 to 80 °C for 0.5 to 24 hours.

[0031] Examples of the compound represented by formula (I-a) include compounds represented by the following formula, etc., and they can be easily obtained from the market. TIFF2025105524000031.tif71140

[0032] Examples of the salt represented by formula (I-b) include salts represented by the following formula, etc., and they can be easily obtained from the market. TIFF2025105524000032.tif63123

[0033] 〔Phenol generator〕 The phenol generator of the present invention is a phenol generator containing a phenolate (I). The phenolate (I) of the present invention can act as a quencher in a resist composition. When the phenolate (I) is used as a quencher in the resist composition, the phenol generator may contain only one type or two or more types of phenolates (I). The phenol generator of the present invention may contain a phenolate known in the resist field other than the phenolate (I). In this case, the content ratio (mass ratio) of the phenolate (I) to the phenolate other than the phenolate (I) is usually 1:99 to 100:0, preferably 1:99 to 99:1, more preferably 2:98 to 98:2, and even more preferably 5:95 to 95:5.

[0034] 〔Resist composition〕 The resist composition of the present invention contains a phenol generator containing the phenolate (I) of the present invention and an acid generator other than the phenol generator (hereinafter sometimes referred to as "acid generator (B)"). The acid generator (B) may be used alone or in combination of two or more. The resist composition of the present invention may contain a compound having a phenolic hydroxyl group or a benzoic acid carboxyl group and / or a compound in which the hydroxyl group of the phenolic hydroxyl group or the carboxyl group of the benzoic acid carboxyl group is protected by an acid-labile group (hereinafter sometimes referred to as "phenolic hydroxyl group-containing compound etc. (L)" or "compound (L)"). The phenolic hydroxyl group-containing compound etc. (L) may be in any form such as a low molecular weight compound, an oligomer, a resin, etc. The resist composition preferably further contains a quencher (hereinafter sometimes referred to as "quencher (C)") and / or a solvent (hereinafter sometimes referred to as "solvent (E)"). In the resist composition of the present invention, the content rate of the phenolate (I) is preferably 0.1 mass% or more and 35 mass% or less, more preferably 0.5 mass% or more and 30 mass% or less, and even more preferably 1 mass% or more and 25 mass% or less with respect to the solid content of the resist composition.

[0035] <Acid generator (B)> In the resist composition of the present invention, the total content of the acid generator (B) is preferably 0.1% by mass or more and 99.9% by mass or less, more preferably 1% by mass or more, more preferably 45% by mass or less, more preferably 1% by mass or more and 40% by mass or less, and still more preferably 3% by mass or more and 40% by mass or less, based on the solid content of the resist composition. When the resin (A) described later is included, the total content of the acid generator (B) is preferably 1 part by mass or more (more preferably 3 parts by mass or more) and preferably 55 parts by mass or less (more preferably 50 parts by mass or less, still more preferably 45 parts by mass or less) with respect to 100 parts by mass of the resin (A).

[0036] As the acid generator (B), 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, sulfonylimide anion, sulfonylmethide anion, and carboxylic acid anion, etc. Further, the acid generator (B) may be one of the structural units constituting the resin contained in the resist composition of the present invention, such as the above-described structural unit (a7).

[0037] As the acid generator (B), compounds that generate acid by radiation described in, for example, JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, JP-A-63-146029, U.S. Patent No. 3,779,778, U.S. Patent No. 3,849,137, German Patent No. 3914407, European Patent No. 126,712, etc. can be used. Further, compounds produced by known methods may also be used. 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 below. When the resist composition of the present invention has a compound having an acid-labile group, a resin containing a structural unit having an acid-labile group may not be included.

[0038] As a preferred form of the acid generator (B), salts represented by formula (B1) (hereinafter sometimes referred to as "acid generator (B1)") and salts represented by formula (B3) (hereinafter sometimes referred to as "acid generator (B3)") can be mentioned. TIFF2025105524000033.tif1392[In formula (B1), all symbols have the same meanings as described above respectively.]

[0039] L b1 As the (nb1 + 1)-valent hydrocarbon group of L, from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group combining two or more of these groups, nb1 hydrogen atoms are removed, and a group bonding to one or more Ls can be mentioned. b2 is mentioned. The number of carbon atoms of the hydrocarbon group is preferably 1 to 48, more preferably 1 to 42, even more preferably 1 to 36, still more preferably 1 to 30, and even more preferably 1 to 24. 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, 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, decanyl group, undecanyl group, dodecanyl group, tridecanyl group, tetradecanyl group, pentadecanyl group, heptadecanyl group, etc. 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 in the chain hydrocarbon group is preferably 1 to 36, more preferably 1 to 24, still more preferably 1 to 20, even more preferably 1 to 18, still even more preferably 1 to 12, and still more preferably 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, cyclopentane group, cyclohexane group, cyclopentyl group, cyclooctyl group, etc. 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, adamantanyl group, etc. Examples of the cycloalkyl group in which two or more rings are condensed include bicyclo[4.4.0]decanyl group, steroid group (steroid skeleton), etc. Examples of the ring 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. Further, a double bond may be formed between two carbon atoms included in the alicyclic hydrocarbon group. More specifically, examples of the alicyclic hydrocarbon group include those represented by the following formula. TIFF2025105524000034.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, still even more preferably 3 to 10, and still 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 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. TIFF2025105524000035.tif1185 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 still 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 taken as the number of carbon atoms of the hydrocarbon group. L b1Among the hydrocarbon groups, examples of groups in which -CH2- contained in a chain hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2- 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 carbonyl group (a group in which -CH2- contained in a methylene group is replaced by -CO-), an oxy group (a group in which -CH2- contained in a methylene group is replaced by -O-), a thiol 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 alkoxy group (a group in which -CH2- at any position contained in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position contained in an alkyl group is replaced by -O-CO-), 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 alkylthio group (a group in which -CH2- at any position contained in an alkyl group is replaced by -S-), an alkylsulfonyl group (a group in which -CH2- at any position contained in an alkyl group is replaced by -SO2-), an alkoxycarbonyloxy group (a group in which -CH2-CH2-CH2- at any position contained in an alkyl group is replaced by -O-CO-O-), 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 alkanediylthio group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -S-), an alkanediylsulfonyl group (a group in which -CH2- at any position contained in an alkanediyl group is-SO2- and other groups that have replaced it). 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 b1 Among the hydrocarbon groups of b1 , as groups in which -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2-, cyclic ethers, cyclic ketones, cyclic esters (lactones), cyclic thioethers, cyclic acetals, cyclic sultones, etc. can be mentioned. 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. TIFF2025105524000036.tif48165L b1 Among the hydrocarbon groups of b1 , -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-. As groups in which -CH2- is replaced by -O- or -S-, a furan ring or a thiophene ring can be mentioned respectively. As groups 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-, those similar to the groups exemplified in this specification are included within the range allowed by the upper limit of the number of carbon atoms. As groups combining two or more of a chain hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group, there can be mentioned 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. As groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, a condensed ring may be used. L b2 As the divalent hydrocarbon group of b2 , one hydrogen atom is removed from 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 the group that binds to Y b1 is mentioned. 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, within the range permitted by the number of carbon atoms, are each L b1 Examples include the groups obtained by removing one hydrogen atom from the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and the group formed by combining two or more of these groups exemplified by b1 . L b1 and L b2 Examples of the substituents 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 b1 and L b2 When and are groups 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 the aromatic hydrocarbon group has. Also, when the -CH2- of the chain hydrocarbon group contained in the hydrocarbon group of and is replaced by -O-, -CO-, -S-, or -SO2-, the hydrocarbon groups of and 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. b1 and L b2 The number of substituents that and may have is not particularly limited, and they may have a plurality of substituents. b1 and L b2 Examples of the cyclic hydrocarbon group of Y include an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group of an alicyclic hydrocarbon group and an aromatic hydrocarbon group. L b1 and L b2 The alicyclic hydrocarbon group and aromatic hydrocarbon group of Y are each the same as the alicyclic hydrocarbon group and aromatic hydrocarbon group exemplified by b1 , and when they have no substituents, they may be a monovalent alicyclic hydrocarbon group and aromatic hydrocarbon group. Y b1 Examples of the cyclic hydrocarbon group of Y include an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group of an alicyclic hydrocarbon group and an aromatic hydrocarbon group. Y b1 The alicyclic hydrocarbon group and aromatic hydrocarbon group of Y are each the same as the alicyclic hydrocarbon group and aromatic hydrocarbon group exemplified by b1 , and when they have no substituents, they may be a monovalent alicyclic hydrocarbon group and aromatic hydrocarbon group. b1 Examples of the alicyclic hydrocarbon group and aromatic hydrocarbon group of Y are the same as those exemplified by b1 , and when they have no substituents, they may be a monovalent alicyclic hydrocarbon group and aromatic hydrocarbon group. Y b1The substituents that the methyl group may have include a halogen atom, a cyano group, a hydroxy group, and a nitro group. Y b1 The substituents that the cyclic hydrocarbon group of Y may have include a halogen atom, a cyano group, a nitro group, or a hydrocarbon group having 1 to 18 carbon atoms which may have a halogen atom, a cyano group, and a nitro group. -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-. Y b1 The hydrocarbon group having 1 to 18 carbon atoms that the cyclic hydrocarbon group of Y may have as a substituent includes a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group combining these groups. Examples of the chain hydrocarbon group, the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and a group combining two or more of these groups include, within the range permitted by the upper limit of the number of carbon atoms, L b1 The same groups as the chain hydrocarbon group, the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and a group combining two or more of these groups exemplified in L are included. 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 Y may have as a substituent is replaced by -O-, -S-, -CO-, or -SO2- include, within the range permitted by the upper limit of the number of carbon atoms, L b1 The same groups as the groups exemplified by the group in which -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -CO-, or -SO2-. Also, Y b1 The hydrocarbon group having 1 to 18 carbon atoms that the cyclic hydrocarbon group of Y 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.

[0040] The anion of the salt represented by formula (B1) is preferably an anion represented by the following formula (B1-A1) or an anion represented by formula (B1-A2). TIFF2025105524000037.tif31125[In formula (I-A1), L b2 and Y b1 have the same meanings as in formula (I-A). Q b1 Qb2 , 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 within 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 within 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 preferably such that at least one of Q and Q contains 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. b1 and Q b2 are preferably such that at least one of Q and Q contains 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 is preferably, independently of one another, 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. z1 is preferably any integer from 0 to 3, more preferably 0, 1 or 2. X 1 is preferably -O-CO- or -CO-O-.

[0041] L b3 As the hydrocarbon group in, within the range allowed by the upper limit of the number of carbon atoms, L of formula (I-A) b1 is exemplified by the same hydrocarbon groups as those of L of formula (I-A). In formula (B1-A1), L b3 is preferably a single bond, a chain hydrocarbon group having 1 to 12 carbon atoms which may have a substituent (in the chain hydrocarbon group, -CH2- may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (in the alicyclic hydrocarbon group, -CH2- may be replaced by -O-, -S-, -CO- or -SO2-), an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent (in the aromatic hydrocarbon group, -CH2- may be replaced by -O- or -S-), or a group formed by combining two or more of these groups, more 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-. TIFF2025105524000038.tif1582 [In formula (Lb3-1), nb2 represents the same meaning as in formula (I-A1). L b31 represents a single bond or an acyclic hydrocarbon group having 1 to 12 carbon atoms, in which -CH2- contained in the acyclic hydrocarbon group may be replaced by -O- or -CO-, and the acyclic 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, in which -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 is represented by the bonding site with.] In formula (Lb3-1), the acyclic hydrocarbon group of L b31 , as long as the upper limit of the number of carbon atoms permits, is the same group as the acyclic hydrocarbon group exemplified by L b1 . In formula (Lb3-1), the alicyclic hydrocarbon group and the aromatic hydrocarbon group of W b3 , as long as the upper limit of the number of carbon atoms permits, is the same group as the alicyclic hydrocarbon group and the aromatic hydrocarbon group exemplified by L b1 . In formula (Lb3-1), the substituent that the acyclic hydrocarbon group of L b31 may have and the substituent that the alicyclic hydrocarbon group and the aromatic hydrocarbon group of W b3 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- may be replaced by -O- or -CO-). Among them, as the alicyclic hydrocarbon group and the aromatic hydrocarbon group of W b3 , the alicyclic hydrocarbon group and the aromatic hydrocarbon group represented below are preferred. In the alicyclic hydrocarbon group and the aromatic hydrocarbon group represented below, * and ** represent bonding sites, and * represents X 1 or L b31represents a binding site with, and ** represents a hydrogen atom, a substituent, or L b2 represents a binding site with, and at least one ** is L b2 represents a binding site with. Further, in the alicyclic hydrocarbon group represented by the following, -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), a carbonate ester ring, a sulfonic acid ester ring (sultone), or an acetal ring is formed. In formula (B1-A1), L b2 is preferably 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 is 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 binding sites, and ** represents the binding site with Y b1 However, the total number of carbon atoms of L b21 , X 2 and L b22 is 12 or less.) is more preferable. In formula (B1-A1), Y b1is 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, R Yc represents a hydrogen atom or a substituent which the cyclic hydrocarbon group of Y b1 may have, and * represents a bonding site with L b2 . The alicyclic hydrocarbon group and aromatic hydrocarbon group represented by the following formulae may have, although not particularly illustrated in the following formulae, other substituents which the cyclic hydrocarbon group of Y b1 may have. TIFF2025105524000040.tif94164

[0042] As the anion in the salt represented by formula (B1), anions represented by formula (B1-A1-1) to formula (B1-A1-85) [hereinafter, may be referred to as "anion (B1-A1-1)" etc. according to the formula number] are preferable, and an anion represented by any of formula (B1-A1-1) to formula (B1-A1-4), formula (B1-A1-9), formula (B1-A1-10), formula (B1-A1-24) to formula (B1-A1-33), formula (B1-A1-36) to formula (B1-A1-40), formula (B1-A1-47) to formula (B1-A1-85) is more preferable. TIFF2025105524000041.tif216161

[0043] TIFF2025105524000042.tif249151

[0044] TIFF2025105524000043.tif254163

[0045] 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 described above. Specific examples of the anion represented by the formula (B1-A1) include the anions described in JP-A-2010-204646.

[0046] Preferred anions in the salt represented by the formula (B1) include the anions represented by the formulas (B1a-1) to (B1a-70), respectively. TIFF2025105524000044.tif185163

[0047] TIFF2025105524000045.tif252166

[0048] TIFF2025105524000046.tif69166

[0049] Among them, anions represented by any of the formulas (B1a-1) to (B1a-3), (B1a-7) to (B1a-19), and (B1a-22) to (B1a-70) are preferred.

[0050] The anion represented by the formula (B1-A2) is represented by the following formula. TIFF2025105524000047.tif23100[In the formula (B1-A2), L b2 and Y b1 have the same meanings as in the 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, a plurality of -L b2 -Y b1 may be the same as or different from each other. nb3 represents any integer from 0 to 4. When nb3 is 2 or more, a plurality of R b1 may be the same as or different from each other. However, 1 ≦ nb4 + nb3 ≦ 5 is satisfied.]

[0051] In the formula (B1-A2), the hydrocarbon group of L b2 and the cyclic hydrocarbon group of Y b1 are exemplified by the same ones as the examples of the hydrocarbon group of L b2 in the formula (B1) and the examples of the cyclic hydrocarbon group of Y b1 within the range allowed by the upper limit of the number of carbon atoms. For the hydrocarbon group of L b2 , the methyl group of Y b1 and the substituents that the cyclic hydrocarbon group may have, the same ones as the examples of the hydrocarbon group of L b2 in the formula (B1), the methyl group of Y b1 and the examples of the substituents that the cyclic hydrocarbon group may have are exemplified. These hydrocarbon groups, methyl groups and cyclic hydrocarbon groups may have one substituent or a plurality of substituents. In the formula (B1-A2), L b2 is preferably a chain hydrocarbon group having 1 to 12 carbon atoms (where -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), more preferably, *-CO-O-L b41 -(L b41is a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-. * is SO3 - represents the bonding site with the benzene ring to which - is bonded. L b41 is preferably a single bond or a chain hydrocarbon group having 1 to 3 carbon atoms. ), and more preferably, *-CO-O-. 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 Y in the formula (B1-A1) b1 or L b1 is more preferably an alicyclic hydrocarbon group or an aromatic hydrocarbon group exemplified by b1 . 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).

[0052] In the 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 is preferably in the following structure which is the m-position substitution of the benzene ring with respect to the bonding position of SO3 - TIFF2025105524000048.tif24105[In the above formula, L b2 , Y b1 , R b1 , nb3 represent the same meanings as in the formula (B1-A2).] In the formula (B1-A2), when nb4 is 2 or more, a plurality of L b2 and Y b1 preferably represent the same group as each other.​

[0053] R b1 Examples of the alkyl group having 1 to 6 carbon atoms for R include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group and the like. The number of carbon atoms of the alkyl group is preferably 1 to 4, more preferably 1 to 3. R b1 Examples of the halogen atom for R include fluorine atom, chlorine atom, bromine atom, iodine atom and the like. 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 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. R b1 Each R is preferably independently 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 any integer from 0 to 4 (that is, nb3 - 1 is any integer from 0 to 3), 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, it is preferable that nb3 is 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, it is preferable that one of R b1 is a halogen atom and the other is a halogen atom or an alkyl group having 1 to 4 carbon atoms, and R b1It is more preferable that one of them is a fluorine atom or an iodine atom, and the other is a fluorine atom, an iodine atom or an alkyl group having 1 to 3 carbon atoms.

[0054] Examples of the anion (B1-A2) include, for example, the following anions. Among them, anions represented by formula (B2a-1) to formula (B2a-20) are preferable, and anions represented by formula (B2a-1) to formula (B2a-11), formula (B2a-16) to formula (B2a-20) are more preferable. TIFF2025105524000049.tif94162

[0055] TIFF2025105524000050.tif1293[In formula (B3), all symbols have the same meanings as described above respectively.] In formula (B3), L b2 ’ and Y b1 ’ Examples of the hydrocarbon group, cyclic hydrocarbon group and their substituents are the same groups as L b2 and Y b1 in formula (B1). In formula (B3), L b2’ is a single bond, *-L b23 -X 2 - or *-L b23 -X 2 -W 2 -X 3 -(L b23 represents an alkanediyl group having 1 to 6 carbon atoms which may have a fluorine atom, X 2 and X 3 each independently represent -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-, and * represents a bonding site with SO2.). It is preferably this. In formula (B3), Y b1’is preferably a trifluoromethyl group, an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, or a phenyl group which may have a substituent, and more preferably a trifluoromethyl group or a group represented by Formula (Y1) to Formula (Y36) in Formula (B1). nb5 is preferably 2 or 3. In Formula (B3), two SO2-L b2’ -Y b1’ together form a ring containing A 1 For example, an anion represented by Formula (B3’) can be mentioned. TIFF2025105524000051.tif21113 [In Formula (B3’), A 1 nb5 has the same meaning as in Formula (B3). Y b1 L b2 has the same meaning as in Formula (B1). W b4 represents a disulfonylimide ring or a disulfonylmethide ring having 3 to 12 carbon atoms which may have a fluorine atom.] W b4 The disulfonylimide ring or disulfonylmethide ring of W preferably has 3 to 6 carbon atoms, and the hydrogen atoms of the methylene groups contained in the ring are preferably replaced by fluorine atoms.

[0056] Examples of the anion represented by Formula (B3) include the following. Among them, anions represented by Formula (B3a-1) and Formula (B3a-2) are preferred. TIFF2025105524000052.tif189164

[0057] In another embodiment of the acid generator (B), examples include those in which the anion of the acid generator (B) is a carboxylic acid anion. Examples of the carboxylic acid anion include the following. TIFF2025105524000053.tif41155

[0058] Z1 + and Z2 +Examples of the organic cation include the same organic cations as those of the organic cation of the phenol salt (I). The acid generator (B) is a combination of the above-mentioned anion and the above-mentioned organic cation, and these can be arbitrarily combined. Preferred examples of the acid generator (B) include a combination of an anion represented by any one of the anions represented by any of formula (B1a-1) to formula (B1a-3), formula (B1a-7) to formula (B1a-19), formula (B1a-22) 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 the cation (b2-1), the cation (b2-2), the cation (b2-3), the cation (b2-4) or the cation (b2-5).

[0059] Preferred examples of the acid generator (B) include 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). 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. TIFF2025105524000054.tif198167

[0060] TIFF2025105524000055.tif244163

[0061] TIFF2025105524000056.tif254165

[0062] TIFF2025105524000057.tif254160

[0063] TIFF2025105524000058.tif249163

[0064] TIFF2025105524000059.tif249150

[0065] TIFF2025105524000060.tif186160

[0066] <Compound (L) containing phenolic hydroxyl group, etc.> The resist composition of the present invention preferably further contains a compound having a phenolic hydroxyl group or a benzoic acid carboxy group and / or a compound in which the hydroxyl group of the phenolic hydroxyl group or the carboxy group of the benzoic acid carboxy group is protected by an acid-labile group. The compound (L) contains at least one structure represented by the formula (L0) as a partial structure. TIFF2025105524000061.tif2470[In the formula (L0), Ar lk represents an aromatic hydrocarbon ring having 6 to 18 carbon atoms which may have a substituent. X lk represents a single bond or a carbonyl group. R lk represents a hydrogen atom or an acid-labile group. lk represents an integer of 1 or more, and when lk is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. * represents a bonding site. lo represents an integer of 1 or more.] Ar lk Examples of the aromatic hydrocarbon ring of Ar include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and the like. Ar lk Examples of the substituent that the aromatic hydrocarbon ring of Ar may have include the same groups as the groups exemplified by R lk11 and R lk22 and the like. Ar lk is preferably a benzene ring or a naphthalene ring which may have a substituent, and more preferably a benzene ring which may have a substituent. R lkExamples of the acid-labile group include a group represented by the formula (1a) (hereinafter, sometimes referred to as "acid-labile group (1a)") and a group represented by the formula (2a) (hereinafter, sometimes referred to as "acid-labile group (2a)"). Among them, the group represented by the formula (2a) is preferred. TIFF2025105524000062.tif2156[In the formula (1a), R aa1 、R aa2 and R aa3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with the carbon atom 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. * represents a bonding site.] TIFF2025105524000063.tif2160[In the formula (2a), R aa1’ and R aa2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R aa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa2’ and R aa3’ are bonded to each other to form a heterocyclic group having 3 to 20 carbon atoms together with the -C-X a - to which they are bonded, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom. X a represents an oxygen atom or a sulfur atom. * represents a bonding site.]

[0067] Examples of the alkyl group of R aa1 、R aa2 and R aa3 include a methyl group, an ethyl group, a propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, etc. R aa1 、Raa2 and R aa3 The number of carbon atoms of the alkyl group of is 1 to 8, preferably 1 to 6, more preferably 1 to 4, and still more preferably 1 to 3. R aa1 R aa2 and R aa3 Examples of the alkenyl group of are 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. R aa1 R aa2 and R aa3 The alicyclic hydrocarbon group of 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. Examples of the polycyclic alicyclic hydrocarbon group include, for example, decahydronaphthyl group, adamantyl group, norbornyl group and the following group (* represents the bonding site). R aa1 R aa2 and R aa3 The number of carbon atoms of the alicyclic hydrocarbon group of is 3 to 20, preferably 3 to 18, more preferably 3 to 16, and still more preferably 3 to 12. TIFF2025105524000064.tif9159R aa1 R aa2 and R aa3 Examples of the aromatic hydrocarbon group of include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group. R aa1 R aa2 and R aa3 The number of carbon atoms of the aromatic hydrocarbon group of is 6 to 18, preferably 6 to 14, more preferably 6 to 10. Examples of the combined group include a group combining the above-described alkyl group and alicyclic hydrocarbon group (e.g., an alkylcycloalkyl group or cycloalkylalkyl group such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornil group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), 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, etc.), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), an aryl-cycloalkyl group such as phenylcyclohexyl group, and the like.

[0068] R aa1 and R aa2 When they are bonded to each other to form an alicyclic hydrocarbon group together with the carbon atom to which they are bonded, examples of -C(R aa1 )(R aa2 )(R aa3 ) include the following groups. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and still more preferably 3 to 12. * represents the bonding site with -O-. TIFF2025105524000065.tif27138

[0069] Examples of the group represented by formula (1a) include a 1,1,1-trialkyl group (a group in which R aa1 , R aa2 and R aa3 are alkyl groups in formula (1a), preferably a tert-butyl group), a 2-alkyladamantan-2-yl group (in formula (1a), R aa1 , R aa2 and the carbon atom to which they are bonded form an adamantyl group, and R aa3 is an alkyl group), and a 1-(adamantan-1-yl)-1,1-dialkyl group (in formula (1a), R aa1 and R aa2 are alkyl groups, and R aa3is an adamantyl group).

[0070] R aa1' , R aa2' and R aa3' Examples of the hydrocarbon group include chain hydrocarbon groups such as alkyl groups, alicyclic hydrocarbon groups, cyclic hydrocarbon groups such as aromatic hydrocarbon groups, and groups formed by combining these groups. Alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining these groups are R aa1 , R aa2 and R aa3 Examples of the groups include the same groups as those listed in 1. R aa2' and R aa3' are bonded to each other and the carbon atom to which they are bonded and X a When forming a heterocyclic group together with -C(R aa1' )(R aa2' )-X a -(R aa3' ) includes the following groups. * represents a bonding site. The heterocyclic group may have 3 to 20 carbon atoms, preferably 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms, and further preferably 3 to 12 carbon atoms. TIFF2025105524000066.tif21143R aa1 , R aa2 , R aa3 , R aa1' , R aa2' and R aa3' The halogen atom which may be contained includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R aa1' and R aa2' At least one of these is preferably a hydrogen atom.

[0071] Specific examples of the acid labile group (1a) include the following groups, where * represents a bonding site. TIFF2025105524000067.tif60162Specific examples of the acid labile group (2a) include the following groups: * represents a binding site. TIFF2025105524000068.tif59148

[0072] lk may be any integer of 2 or more. Further, lk may be, for example, any integer of 13 or less. Among them, lk is preferably any integer of 1 to 11, more preferably any integer of 1 to 9, still more preferably any integer of 1 to 7, even more preferably any integer of 1 to 6, yet even more preferably any integer of 1 to 5, and even still more preferably any integer of 1 to 4. lo may be any integer of 2 or more. Further, lo may be, for example, any integer of 13 or less. Among them, lo is preferably any integer of 1 to 11, more preferably any integer of 1 to 9, still more preferably any integer of 1 to 7, even more preferably any integer of 1 to 6, yet even more preferably any integer of 1 to 5, and even still more preferably any integer of 1 to 4.

[0073] Examples of the compound (L) containing one or more of the structures represented by the formula (L0) as partial structures include the compound represented by the formula (LX). TIFF2025105524000069.tif23130 [In the formula (LX), Ar k1 and Ar k2 each independently represents an aromatic hydrocarbon ring having 6 to 18 carbon atoms. X lk1 and X lk2 each independently represents a single bond or a carbonyl group. R lk1 and R lk2 each independently represents a hydrogen atom or an acid-labile group. Lx represents a hydrocarbon group having 1 to 80 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. R lk11 and R lk22Each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a halogen atom or a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. R lk11 and R lk22 , R lk11 and Lx or R lk22 and Lx may each form a ring by bonding, the ring may have a substituent, and -CH2- contained in the ring may be replaced by -O-, -S-, -CO-, -SO- or -SO2-. lx2 represents an integer of any one of 1 to 6, and when lx2 is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. lk1’ represents an integer of any one of 1 to 13, and when lk1’ is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. lk11’ represents an integer of any one of 0 to 12, and when lk11’ is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. lk2’ represents an integer of any one of 1 to 13, and when lk2’ is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. lk22’ represents an integer of any one of 0 to 12, and when lk22’ is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other.] Ar k1 and Ar k2 Examples of the aromatic hydrocarbon ring of Ar lk include the same groups as those exemplified for the group of the aromatic hydrocarbon ring of Ar R lk1 and R lk2 Examples of the acid-labile group of R lk include the same groups as those exemplified for the acid-labile group of R Examples of the hydrocarbon group for Lx include a chain hydrocarbon group, an alicyclic hydrocarbon group which is monocyclic or polycyclic (including a spiro ring, a condensed ring, a bridged ring, etc.), and an aromatic hydrocarbon group. 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. The hydrocarbon group for Lx is a (lx2 + 1)-valent hydrocarbon group, and depending on lx2, it can be a 2- to 7-valent hydrocarbon group. The number of carbon atoms in the hydrocarbon group is preferably 1 to 72, more preferably 1 to 60, further preferably 1 to 48, even more preferably 1 to 36, and even further preferably 1 to 24. Examples of the chain hydrocarbon group include an alkanediyl 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. Note that the terminal of the branched alkanediyl group may be a methyl group. In addition, examples of the chain hydrocarbon group also include a group in which one or more hydrogen atoms of the above-described groups are replaced by a bonding site. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, preferably 1 to 10, even more preferably 1 to 9, even further preferably 1 to 8, even more preferably 1 to 6, and even further preferably 1 to 4. Examples of the alicyclic hydrocarbon group include 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; 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; spirocyclic alicyclic hydrocarbon groups such as spirocyclohexane-1,2′-cyclopentane group, spiroadamantane-2,3′-cyclopentane group; and spiro ring groups having a cycloalkyl group spiro-bonded to a norbornyl group or an adamantyl group respectively. In addition, examples of the alicyclic hydrocarbon group include groups in which one or more hydrogen atoms of the above-described groups are replaced at the bonding site. Examples of the alicyclic hydrocarbon group include the following groups. The bonding site can be at any position. TIFF2025105524000070.tif44163 The number of carbon atoms of the alicyclic hydrocarbon group is, for example, 3 to 72, may be 3 to 60, preferably 3 to 24, more preferably 3 to 20, still more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 3 to 12. Examples of the aromatic hydrocarbon group include arylene groups such as phenylene group, naphthylene group, anthrylene group, biphenylene group, phenanthrylene group and the like. In addition, examples of the aromatic hydrocarbon group include groups in which one or more hydrogen atoms of the above-described groups are replaced at the bonding site. The number of carbon atoms of the aromatic hydrocarbon group is, for example, 6 to 72, may be 6 to 60, preferably 6 to 24, more preferably 6 to 20, still more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Examples of a group formed by combining two or more of them 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, and a group formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group. In the combination, two or more of the alicyclic hydrocarbon group, aromatic hydrocarbon group, and chain hydrocarbon group may be combined with each other. Also, any of the groups may be bonded to Ar k1 or Ar k2 . Examples of a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group include, for example, -alicyclic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-alicyclic hydrocarbon group-, etc. Examples of a group formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group include, for example, -aromatic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-aromatic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-aromatic hydrocarbon group-, etc. Examples of a group formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group include -aromatic hydrocarbon group-alicyclic hydrocarbon group-, -alicyclic hydrocarbon group-aromatic hydrocarbon group-, -alicyclic hydrocarbon group-aromatic hydrocarbon group-alicyclic hydrocarbon group-, etc. Also, examples of the combined group include a group in which one or more hydrogen atoms of the above-described group are replaced with a bonding site. -CH2- contained in the hydrocarbon group of Lx may be replaced with -O-, -S-, -SO2- or -CO-. As described above, examples of the group in which -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include a hydroxy group, a carboxy group, a thiol group, an oxy group, a carbonyl group, a thio group, a sulfonyl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkanediyl-oxy group, an alkanediyl-oxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, an aromatic hydrocarbon group-carbonyl-oxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy 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. In addition, 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 permits. Examples of the group in which -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- also include a group in which one or more hydrogen atoms of the above-described groups are replaced at the bonding site. Examples of the substituent that Lx may have include, for example, a halogen atom, a cyano group, and the like. When Lx is a group formed by combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group with a chain hydrocarbon group such as an alkyl group, the chain hydrocarbon group such as an alkyl group can be a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. When -CH2- contained in the chain hydrocarbon group such as an alkyl group contained in Lx is replaced by -O-, -CO-, -S- or -SO2-, Lx can 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, a sulfonyl group, and the like. Examples of the substituent that Lx may have include R described below lk11 and Rlk22 Groups similar to the groups exemplified by etc. are also included.

[0074] R lk11 and R lk22 Examples of the halogen atoms of and R include fluorine atom, chlorine atom, bromine atom, iodine atom, etc. R lk11 and R lk22 Examples of the hydrocarbon groups of and R include chain hydrocarbon groups such as alkyl groups and alkanediyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. The alkyl group is a straight-chain or branched alkyl group. For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc. are included. The alkanediyl group is a straight-chain or branched alkanediyl group. Examples of straight-chain alkanediyl groups include methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, 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, etc. Examples of branched alkanediyl groups include ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, etc. The terminal of the branched alkanediyl group may be a methyl group. The number of carbon atoms in the chain hydrocarbon group is preferably from 1 to 12, more preferably from 1 to 9, still more preferably from 1 to 6, even more preferably from 1 to 4, and even more preferably from 1 to 3. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the alicyclic hydrocarbon group include the groups represented below. The bonding site can be at any position. TIFF2025105524000071.tif43163Specifically, examples of the monocyclic alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, cyclododecyl group and the like. Examples of the polycyclic alicyclic hydrocarbon group include polycyclic cycloalkyl groups such as decahydronaphthyl group, adamantyl group, norbornyl group and the like. Examples of the spirocyclic alicyclic hydrocarbon group include cycloalkyl groups such as spirocyclohexane-1,2′-cyclopentane group, spiroadamantane-2,3’-cyclopentane group, and spiro rings having a cycloalkyl group spiro-bonded to a norbornyl group or an adamantyl group respectively. The number of carbon atoms in the alicyclic hydrocarbon group is preferably from 3 to 18, more preferably from 3 to 16, and still more preferably from 3 to 12. Examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, biphenyl group, anthryl group, phenanthryl group, binaphthyl group and the like. The number of carbon atoms in the aromatic hydrocarbon group is preferably from 6 to 18, more preferably from 6 to 14, and still more preferably from 6 to 10. Examples of the group formed by combining two or more groups include a group formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, an aromatic hydrocarbon group - alkane diyl group - *, an alkyl group - aromatic hydrocarbon group - *, an alkyl group - aromatic hydrocarbon group - alkane diyl group - *, and the -CH2- contained in the alkane diyl group and the alkyl group may be replaced by -O-, -CO-, -S- or -SO2-.), a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, an alicyclic hydrocarbon group - alkane diyl group - *, an alkyl group - alicyclic hydrocarbon group - *, an alkyl group - alicyclic hydrocarbon group - alkane diyl group - *, and the -CH2- contained in the alicyclic hydrocarbon group, the alkane diyl group and the alkyl group may be replaced by -O-, -CO-, -S- or -SO2-.), and a group formed by combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, an aromatic hydrocarbon group - alicyclic hydrocarbon group - *, an alicyclic hydrocarbon group - aromatic hydrocarbon group - *, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-.). * represents a bonding site. Examples of the aromatic hydrocarbon group - alkane diyl group - * include aralkyl groups such as a benzyl group and a phenethyl group. Examples of the alkyl group - aromatic hydrocarbon group - * include a tolyl group, a xylyl group, and a cumenyl group. Examples of the alicyclic hydrocarbon group - alkane diyl group - * include cycloalkylalkyl groups such as a cyclohexylmethyl group, a cyclohexylethyl group, a 1-(adamantan-1-yl)methyl group, and a 1-(adamantan-1-yl)-1-methylethyl group. Examples of the alkyl group - alicyclic hydrocarbon group - * include cycloalkyl groups having an alkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, and a 2-alkyladamantan-2-yl group. Examples of the aromatic hydrocarbon group - alicyclic hydrocarbon group - * include a phenylcyclohexyl group. Examples of the alicyclic hydrocarbon group - aromatic hydrocarbon group - * include a cyclohexylphenyl group. In the combination, the alicyclic hydrocarbon group, aromatic hydrocarbon group, and chain hydrocarbon group may each be combined with two or more types. Also, any of the groups may be bonded to the benzene ring. R lk11 and R lk22 When -CH2- contained in the hydrocarbon group represented by is replaced by -O-, -CO-, -S- or -SO2-, the carbon number before replacement is defined as the total carbon number of the hydrocarbon group. Also, the number may be one or two or more. Examples of the group in which -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include the same groups as those exemplified by Lx within the range where the upper limit of the carbon number permits. R lk11 and R lk22 Examples of the substituent that the hydrocarbon group of may have include a halogen atom, a cyano group, and the like. R lk11 and R lk22 When is a hydrocarbon group having a halogen atom, lk11 and R lk22 Examples of the hydrocarbon group having a halogen atom of include a chain hydrocarbon group having a halogen atom such as a haloalkyl group, an alicyclic hydrocarbon group having a halogen atom, and an aromatic hydrocarbon group having a halogen atom. The haloalkyl group represents an alkyl group having a halogen atom. Examples of the haloalkyl group 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. Specific examples of the haloalkyl group include perfluoroalkyl groups having 1 to 12 carbon atoms (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. -CH2- contained in the haloalkyl group may be replaced by -O- or -CO- or the like. Examples of such groups include haloalkoxy groups, haloalkoxycarbonyl groups, haloalkylcarbonyl groups, haloalkylcarbonyloxy groups, etc. Specifically, haloalkoxy groups having 1 to 11 carbon atoms, haloalkoxycarbonyl groups having 2 to 11 carbon atoms, haloalkylcarbonyl groups having 2 to 12 carbon atoms, haloalkylcarbonyloxy groups having 2 to 11 carbon atoms, etc. are included. For example, groups in which one or more hydrogen atoms of the groups exemplified above are replaced by halogen atoms are included. The hydrocarbon group may have one substituent or a plurality of substituents.

[0075] Examples of the compound (LX) include a compound represented by the formula (LX-0) (hereinafter sometimes referred to as "compound (LX-0)"). As the compound (LX-0), a compound represented by the formula (LX-1) (hereinafter sometimes referred to as "compound (LX-1)") is preferable. TIFF2025105524000072.tif23125[In the formula (LX-0), symbols other than the following have the same meanings as described above. lk1 represents any integer from 1 to 5. When lk1 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk11 represents any integer from 0 to 4, satisfies 1 ≦ lk1 + lk11 ≦ 5, and when lk11 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk2 represents any integer from 1 to 5, and when lk2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk22 represents any integer from 0 to 4, satisfies 1 ≦ lk2 + lk22 ≦ 5, and when lk22 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. In formula (LX-1), symbols other than the following represent the same meaning as described above. X lk3 represents a single bond or a carbonyl group. R lk3 represents a hydrogen atom or an acid-labile group. Lx1 and Lx2 each independently represent a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. R lk33 represents a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. lx3 represents any integer from 0 to 6, and when lx3 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk3 represents any integer from 1 to 4, and when lk3 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk33 represents any integer from 0 to 3, satisfies 1 ≦ lk3 + lk33 ≦ 4, and when lk33 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. The hydrocarbon group which may have substituents Lx1 and Lx2 (wherein -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-) includes, within the range permitted by the upper limit of the number of carbon atoms and the like, hydrocarbon groups which may have substituents exemplified by Lx (wherein -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-), and the like. R lk33 The halogen atom or hydrocarbon group which may have a substituent of lk33 (wherein -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-) includes, within the range permitted by the upper limit of the number of carbon atoms and the like, hydrocarbon groups which may have a halogen atom or substituents exemplified by R lk11 and R lk22 and the like, which may have a halogen atom or substituents exemplified by R R lk11 and Lx1, or R lk22 and Lx2 may each be bonded to each other to form a ring. In this case, the ring is a condensed ring condensed with the benzene ring or a spiro ring spiro-bonded to the benzene ring because R lk11 and R lk22 are each bonded to the benzene ring. Examples of the condensed ring or spiro ring include those having a total carbon number of 3 to 28, which may be 3 to 24, and are preferably 3 to 20. The condensed ring or spiro ring may be a ring containing one or more of -O-, -CO-, -S- or -SO2-. In the benzene ring (-R lk11 )-Lx1- or benzene ring (-R lk22 )-Lx2-, examples of the ring formed by the bonding of R lk11 and Lx1 or R lk22 and Lx2 include, for example, the following groups and the like. Although the description of the following groups is omitted, they have at least one R lk1 -O-X lk1 - or R lk2 -O-X lk2 -, and may have other R lk11 or R lk22 . * represents the bonding site to the benzene ring. TIFF2025105524000074.tif20123R lk11 and R lk22 may be combined with each other to form a ring. Examples of the ring in this case include a ring having a structure represented by the formula (LX-13) described later, etc.

[0076] As the compound (LX-1), compounds represented by the formula (LX-11), the formula (LX-12), and the formula (LX-13) (hereinafter, may be referred to as "compound (LX-11)", "compound (LX-12)", and "compound (LX-13)", respectively) are preferable. TIFF2025105524000075.tif142158[In the formula (LX-11), the formula (LX-12), and the formula (LX-13), symbols other than the following represent the same meaning as described above. Ly represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-. Examples of the hydrocarbon group having a substituent which may be possessed by Ly (wherein -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-) include hydrocarbon groups which may have a substituent exemplified by Lx within the range allowed by the upper limit of the number of carbon atoms, etc. (wherein -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO2-). lk1 and lk2 are each independently preferably any integer from 1 to 4, more preferably any integer from 1 to 3, and still more preferably 1 or 2. lk11 and lk22 are each independently preferably any integer from 0 to 3, and more preferably any integer from 0 to 2. lk3 is preferably any integer from 1 to 3, and more preferably 1 or 2. lk33 is preferably any integer from 0 to 2. lx2 is preferably an integer of 1 to 5, more preferably an integer of 1 to 4, even more preferably an integer of 1 to 3, and even more preferably 1 or 2. lx3 is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, even more preferably an integer of 0 to 3, and even more preferably an integer of 0 to 2. R lk11 , R lk22 and R lk33 are each independently preferably a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the haloalkyl group or the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), even more preferably an iodine atom, a fluorine atom, a fluorinated alkyl group having 1 to 3 carbon atoms, a hydroxy group, a carboxy group, an alkoxy group having 1 to 3 carbon atoms, a hydroxyalkyl group having 1 to 3 carbon atoms, or an alkyl group having 1 to 3 carbon atoms, and even more preferably an iodine atom, a fluorine atom, a trifluoromethyl group, a hydroxy group, a carboxy group, a methoxy group, or a methyl group. Lx1, Lx2 and Ly are each independently a chain hydrocarbon group having 1 to 10 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), or a combination of a chain hydrocarbon group having 1 to 6 carbon atoms and a cyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced by -O- or -CO-), preferably a chain hydrocarbon group having 1 to 8 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), or a combination of a chain hydrocarbon group having 1 to 4 carbon atoms and a cyclic hydrocarbon group having 3 to 16 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced by -O- or -CO-), more preferably a chain hydrocarbon group having 1 to 6 carbon atoms or a combination of a chain hydrocarbon group having 1 to 4 carbon atoms and a cyclic hydrocarbon group having 3 to 12 carbon atoms. Also, R lk11 and Lx1 or R lk22 and Lx2 are each preferably bonded to form a ring, and R lk11 and R lk22 are preferably bonded to form a ring.

[0077] In one embodiment, the compound (L) may be a low molecular weight compound. A low molecular weight compound is a compound having a molecular weight of less than 10,000. When the compound (L) is a low molecular weight compound, the weight average molecular weight is preferably 7,500 or less, more preferably 5,000 or less, further preferably 4,000 or less, still more preferably 3,000 or less, still further preferably 2,500 or less, still further preferably 2,000 or less, still more preferably 1,500 or less. Also, it is preferably 100 or more, more preferably 120 or more, further preferably 150 or more, still more preferably 300 or more.

[0078] Among the compounds (L), the compound (X) containing an aromatic hydrocarbon ring having a hydroxy group lkis a single bond, and R lk Examples of the compound in which is a hydrogen atom) include compounds represented by the following formula. TIFF2025105524000076.tif180164 Among the compounds (L), the compound (X) containing an aromatic hydrocarbon ring having a carboxy group lk is a carbonyl group, and R lk Examples of the compound in which is a hydrogen atom) include compounds in which at least one hydroxy group of the above compound is replaced with a carboxy group. In the compound (L), both a hydroxy group and a carbonyl group may be present.

[0079] Examples of the low molecular weight compound in which the hydroxy group of the phenolic hydroxy group is protected with an acid-labile group and the low molecular weight compound in which the carboxy group of benzoic acid is protected with an acid-labile group include compounds represented by the following formula. TIFF2025105524000077.tif205165 Examples of the compound in which the carboxy group of the compound (L) containing an aromatic hydrocarbon ring having a carboxy group is protected with an acid-labile group include compounds in which at least one ethoxyethoxy group of the above compound is replaced with an ethoxyethoxycarbonyl group. In the compound (L), both an ethoxyethoxy group and an ethoxyethoxycarbonyl group may be present.

[0080] In the resist composition of the present invention, when the low molecular weight compound of the compound (L) is included, the total content of the low molecular weight compound having a phenolic hydroxy group, the low molecular weight compound having a phenylcarboxy group, the low molecular weight compound in which the hydroxy group of the phenolic hydroxy group is protected with an acid-labile group, and the low molecular weight compound in which the carboxy group of the phenylcarboxy group is protected with an acid-labile group is 0.1% by mass or more and 90% by mass or less, preferably 0.3% by mass or more and 45% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, and even more preferably 1% by mass or more and 35% by mass or less with respect to the solid content of the resist composition.

[0081] In another embodiment, the compound having a phenolic hydroxyl group or a benzoic acid carboxy group and / or the compound (L) in which the hydroxyl group of the phenolic hydroxyl group or the carboxy group of the benzoic acid carboxy group is protected with an acid-labile group may be a resin. When the compound (L) is a resin, it is preferably a resin (A) containing a structural unit represented by the formula (a2-A) (hereinafter sometimes referred to as the structural unit (a2-A)) and / or a structural unit represented by the formula (a1-4) (hereinafter sometimes referred to as the structural unit (a1-4)). TIFF2025105524000078.tif30128[In the formula (a2-A), all the symbols have the same meanings as described above respectively.] TIFF2025105524000079.tif31119[In the formula (a1-4), all the symbols have the same meanings as described above respectively.] R a2 and R a1 、R a27 and R a17 Examples of the halogen atom for R, R, R and R include a fluorine atom, a chlorine atom, and a bromine atom. R a2 and R a1 、R a27 and R a17 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom for R, R, R and 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, and 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 and R a1is 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.

[0082] A a21 and A a11 Examples of the alkanediyl group of A and A 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, etc. The number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 8, even more preferably 1 to 6, still more preferably 1 to 4, even still more preferably 1 to 3, and even more preferably 1 or 2. R a28 and R a18 Examples of the alkyl group of R and R include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group. A a21 and A a11 When -CH2- contained in the alkanediyl group of A and A is replaced by -O-, -CO- or -NR a28 - or -NR a18 -, the number of carbon atoms before replacement is taken as the number of carbon atoms of the hydrocarbon group. A a21 and A a11The group in which -CH2- contained in the alkanediyl group is replaced by -O- or -CO- includes 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 amino group (a group in which -CH2- contained in the alkanediyl group is replaced by -NR a28 - or -NR a18 - (a group replaced by -), an alkoxy group (a group in which any -CH2- contained in the alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which any -CH2-CH2- contained in the alkyl group is replaced by -O-CO-), an alkylcarbonyl group (a group in which any -CH2- contained in the alkyl group is replaced by -CO-), an alkylamino group (a group in which -CH2- contained in the alkyl group is replaced by -NR a28 - or -NR a18 - (a group replaced by -), etc. 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. 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. Among them, -CH2- contained in the alkanediyl group of A a21 is replaced by -O-, -CO- or -NR a28The groups replaced 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-, etc. Among them, *-CO-O-, *-CO-O-A a22 -CO-O- or *-O-A a22 -CO-O-, *-CO-NR a28 - is preferred. Here, A a22 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents the bonding site bonded to the carbon atom to which R a2 is bonded. The alkanediyl group of A a22 includes, within the range allowed by the upper limit of the number of carbon atoms, the same alkanediyl group as A a21 Also, the -CH2- contained in the alkanediyl group of A a11 is replaced by -O-, -CO- or -NR a18 - The groups replaced are *-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 - etc. Among them, *-CO-O-, *-CO-O-A a12 -CO-O-, *-O-A a12 -CO-O-, *-CO-NR a18 - is preferred. Here, A a12 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents the bonding site with the carbon atom to which R a1 is bonded. The alkanediyl group of A a12 includes, within the range allowed by the upper limit of the number of carbon atoms, the same alkanediyl group as A a11 A a21 is a single bond, *-CO-O- or *-CO-O-A a22 ​​-CO-O- is preferred, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-. A a11 is a single bond, *-CO-O- or *-CO-O-A a12 -CO-O- is preferred, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-.

[0083] R a27 and R a17 Examples of the alkoxy group of R and R include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group, and tert-butoxy group. The number of carbon atoms of the alkoxy group is preferably 1 to 4, more preferably 1 to 3, even more preferably methoxy group or ethoxy group, and still more preferably methoxy group. R a27 and R a17 Examples of the alkoxyalkyl group of R and R include methoxymethyl group, ethoxyethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxymethyl group, and tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably methoxymethyl group or ethoxyethyl group, and even more preferably methoxymethyl group. R a27 and R a17 Examples of the alkoxyalkoxy group of R and R include methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, propoxymethoxy group, isopropoxymethoxy group, butoxymethoxy group, sec-butoxymethoxy group, and tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably methoxyethoxy group or ethoxyethoxy group. R a27 and R a17Examples 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, more preferably an acetyl group. R a27 and R a17 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, more preferably an acetyloxy group. R a27 and R a17 is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an 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. 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, may be bonded to any of the o-position, m-position, or p-position with respect to the bonding position of A a21 . Among them, at least one is preferably bonded to the m-position or p-position, more preferably bonded to the m-position. In the case of a naphthalene ring, when the bonding position of A a21 is at the 1-position, it may be bonded to any of the 2nd to 8th positions, and when the bonding position of A a21 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 a21 is at the 1st position, at least one is preferably bonded to the 3rd to 6th positions, more preferably bonded to the 3rd or 4th position. A a21When the bonding position is the 2nd position, it is preferably bonded to the 4th to 7th positions, and more preferably bonded to the 5th or 6th position.

[0084] 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), R in the structural unit (a2-A) a2 Examples include structural units in which the methyl group corresponding to is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. TIFF2025105524000080.tif107169

[0085] When the structural unit (a2-A) is contained in the resin, 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 with respect to 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. 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) is a compound that induces the structural unit (a2-A) (for example, -CH2-C(-R of the structural unit (a2-A) a2 )- is the CH2=C(-R of the double bond before cleavage a2The structural unit (a2-A) can be incorporated into the resin (A) by polymerizing a compound (a2-A') in the state of (a1-4) or the like. Alternatively, the structural unit (a2-A) can be incorporated into the resin by polymerizing the structural unit (a1-4) and then treating with an acid such as p-toluenesulfonic acid. Alternatively, the structural unit (a2-A) can be incorporated into the resin by polymerizing the structural unit (a1-4) and then treating with an alkali such as tetramethylammonium hydroxide.

[0086] 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 further preferably 0 or 1. mc is preferably 0 or 1. R a34 , R a35 and R a36 Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group consisting of a combination thereof. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (* indicates a bonding site): TIFF2025105524000082.tif10151 Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group combining the above-described alkyl group and alicyclic hydrocarbon group (e.g., an alkylcycloalkyl group or cycloalkylalkyl group such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornil group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), 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, etc.), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), an aryl-cycloalkyl group such as phenylcyclohexyl group, etc. 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 and together with the -C-O- to which they are bonded include, for example, the following groups. * represents the bonding site, and one is the bonding site with R a34 TIFF2025105524000083.tif15105

[0087] 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 a36 ​The alkyl group and alicyclic hydrocarbon group in are preferably unsubstituted. R a36 The aromatic hydrocarbon group in preferably has an aromatic ring having an aryloxy group with 6 to 10 carbon atoms.

[0088] -OC(R a34 )(R a35 )-O-R a36 in the structural unit (a1-4) eliminates upon contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxy group or a carboxy group. -X a1 -OC(R a34 )(R a35 )-O-R a36 is In the case of a benzene ring, it 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 2-position to 8-position, and when the bonding position of A a11 is at the 2-position, it may be bonded to any of the 1-position and 3-position to 8-position. 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 3-position to 6-position, and more preferably bonded to the 3-position or 4-position. When the bonding position of A a11 is at the 2-position, it is preferable that it is bonded to the 4-position to 7-position, and more preferably bonded to the 5-position or 6-position.

[0089] Examples of the structural unit (a1-4) include structural units derived from the monomers described in JP-A-2010-204646. Preferably, the structural units represented by formula (a1-4-1) to formula (a1-4-42) and the structural units in which the hydrogen atom corresponding to R a1 in the structural unit (a1-4) is replaced with a halogen atom, a haloalkyl group, or an alkyl group are mentioned, and more preferably, the structural units represented by formula (a1-4-1) to formula (a1-4-5), formula (a1-4-10), formula (a1-4-13), and formula (a1-4-14) are mentioned. TIFF2025105524000084.tif117160

[0090] TIFF2025105524000085.tif77168 When the resin contains the structural unit (a1-4), its content is 5 to 95 mol%, 5 to 60 mol%, 5 to 50 mol% based on the total of all the structural units of the resin, and preferably 10 to 40 mol%, 10 to 95 mol%, more preferably 15 to 90 mol%, still more preferably 20 to 85 mol%, still even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.

[0091] When the resist composition of the present invention contains a resin, the resin may contain a structural unit represented by the formula (a2-A) and a structural unit other than the structural unit represented by the formula (a1-4). Examples of the structural unit other than the structural unit represented by the formula (a2-A) and the structural unit represented by the formula (a1-4) include a structural unit having an acid-labile group other than the structural unit represented by the formula (a1-4) (hereinafter sometimes referred to as "structural unit (a1)"), a structural unit having no acid-labile group other than the structural unit represented by the formula (a2-A) (hereinafter sometimes referred to as "structural unit (s)"), and a structural unit derived from other monomers known in the art, and the like.

[0092] 〈Structural unit (a1)〉 The structural unit (a1) is derived from a monomer having an acid-labile group (hereinafter sometimes referred to as "monomer (a1)"). The acid-labile group contained in the resin 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)). TIFF2025105524000086.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 Ra1 and R a2 are 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, alkenyl group, alicyclic hydrocarbon group, and 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.] TIFF2025105524000087.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 by -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.]

[0093] 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 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 groups (* represents the bonding site). R a1 , R a2 and R a3 The number of carbon atoms of the alicyclic hydrocarbon group of is preferably 3 to 16. TIFF2025105524000088.tif10159R a1 , R a2 and R a3 Examples of the aromatic hydrocarbon group in include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group and the like. Examples of the combined groups include groups combining the above-mentioned alkyl group and alicyclic hydrocarbon group (for example, alkylcycloalkyl groups or cycloalkylalkyl groups such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group and the like), 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 and the like), aromatic hydrocarbon groups having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group and the like), aryl-cycloalkyl groups such as phenylcyclohexyl group and the like. Preferably, ma is 0 and na is 1. R a1 and R a2 When and are bonded to each other to form an alicyclic hydrocarbon group, examples of -C(R a1 )(R a2 )(R a3 ) include the following groups. The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms. * represents a bond to -O-. TIFF2025105524000089.tif28138

[0094] R a1’ 、R a2’ and R a3’ Examples of the hydrocarbon group in R a1’ a2’ a3’ include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups, etc. The alkyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and the group formed by combining these groups are the same as the groups exemplified for R a1 a2 a3 a1 R a2 and R a3 include the same groups as those exemplified for R R a2’ and R a3’ When R a2’ and R a3’ are bonded to each other to form a heterocyclic ring together with the carbon atom to which they are bonded and X, examples of -C(R a1’ )(R a2’ )-X-R a3’ include the following rings. * represents the bonding site. TIFF2025105524000090.tif19124R a1 、R a2 、R a3 、R a1 、R a2’ and R a3’ The halogen atom that R a1 a2 a3 a1 a2’ a3’ may have include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. R a1’ and R a2’ Preferably, at least one of them is a hydrogen atom. na’ is preferably 0.

[0095] Examples of the group (1) include the following groups. In formula (1), when R a1 a2 a3 are alkyl groups, ma = 0, and na = 1. Preferred examples of such a group include a tert-butoxycarbonyl group. In formula (1), R a1 a2together with the carbon atom to which they are attached form an adamantyl group, and R a3 is an alkyl group, ma = 0, and na = 1. In formula (1), R a1 and R a2 are each independently an alkyl group, R a3 is an adamantyl group, ma = 0, and na = 1. Specific examples of group (1) include the following groups. * represents a bond. TIFF2025105524000091.tif150162

[0096] Specific examples of group (2) include the following groups. * represents a bond. TIFF2025105524000092.tif55153

[0097] 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 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.

[0098] As the structural unit derived from the (meth)acrylic monomer having the group (1), there are mentioned a structural unit represented by the formula (a1-0) (hereinafter, may be referred to as structural unit (a1-0)), a structural unit represented by the formula (a1-1) (hereinafter, may be referred to as structural unit (a1-1)), or a structural unit represented by the formula (a1-2) (hereinafter, may be referred to as structural unit (a1-2)). Preferably, it is at least one structural unit selected from the group consisting of the structural unit (a1-0), the structural unit (a1-1), and the structural unit (a1-2), and more preferably, it is at least one or two structural units selected from the group consisting of the structural unit (a1-1) and the structural unit (a1-2). These may be used alone or in combination of two or more. TIFF2025105524000093.tif44141[In the formula (a1-0), the formula (a1-1), and the formula (a1-2), all the symbols have the same meanings as described above respectively.]

[0099] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. R a01 、R a4 、R a5 Examples of the alkyl group of R R a01 、R a4 and R a5 are preferably a hydrogen atom or a methyl group, and more preferably a methyl group. L a01 、L a1 and L a2 are preferably an oxygen atom or *-O-(CH2) k01 -CO-O- (wherein k01 is preferably any integer from 1 to 4, and more preferably 1), and more preferably an oxygen atom. R a02 、R a03 、R a04 、R a6 and R a7 Examples of the alkyl group, alkenyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and the group formed by combining these in R a1, R a2 and R a3 include the same groups as those exemplified above. 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 alkenyl group in R R a02 , R a03 , R a04 , R a6 and R a7 The alicyclic hydrocarbon group of R R a02 , R a03 , R a04 , R a6 and R a7 has preferably 5 to 12 carbon atoms, more preferably 5 to 10 carbon atoms. The group formed by combining an alkyl group and an alicyclic hydrocarbon group preferably has a total carbon number of 18 or less when these alkyl group and alicyclic hydrocarbon group are combined. The group formed by combining an alkyl group and an aromatic hydrocarbon group preferably has a total carbon number of 18 or less when these alkyl group and aromatic hydrocarbon group are combined. R a02 and R a03is preferably an alkyl group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, which may have a halogen atom, and more preferably is a methyl group, an ethyl group, a phenyl group or a naphthyl group, which may have a halogen atom and may have a halogen atom. R a04 is preferably an alkyl group having 1 to 6 carbon atoms or an alicyclic hydrocarbon group having 5 to 12 carbon atoms, which may have a halogen atom, and more preferably is a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group, which may have a halogen atom. R a6 and R a7 is preferably an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, which may have a halogen atom, and more preferably is 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, and even more preferably is 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, and more preferably is 0 or 1. n1 is preferably any integer from 0 to 3, and more preferably is 0 or 1. n1’ is preferably 0 or 1.

[0100] Examples of the structural unit (a1-0) include structural units represented by any of formula (a1-0-1) to formula (a1-0-24) and structural units in which the methyl group corresponding to R a01 in the structural unit (a1-0) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group (an alkyl group having a halogen atom) or another alkyl group, and structural units represented by any of formula (a1-0-1) to formula (a1-0-10), formula (a1-0-13), formula (a1-0-14), formula (a1-0-19) to formula (a1-0-21) are preferred. JPEG2025105524000094.jpg119159

[0101] 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 formulas (a1-1-1) to (a1-1-7) and the methyl group corresponding to R in the structural unit (a1-1) a4 in which the methyl group is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group are preferred, and the structural units represented by any of formulas (a1-1-1) to (a1-1-4) are more preferred. TIFF2025105524000095.tif39169

[0102] Examples of the structural unit (a1-2) include structural units represented by any of formulas (a1-2-1) to (a1-2-20) and structural units in which the methyl group corresponding to R in the structural unit (a1-2) a5 is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group, and the structural units represented by any of formula (a1-2-2), formula (a1-2-5), formula (a1-2-6) and formulas (a1-2-10) to (a1-2-20) are preferred. TIFF2025105524000096.tif91163 When the resin 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, and even still more preferably 40 mol% or more, based on all the structural units of the resin. 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 contains the structural unit (a1-0), its content 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. Also, it is 80 mol% or less, preferably 75 mol% or less, more preferably 70 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 contains the structural unit (a1-1) and / or the structural unit (a1-2), their total content 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. 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 95 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, still more preferably 20 to 80 mol%, and even more preferably 20 to 75 mol%.

[0103] Examples of the structural unit derived from the (meth)acrylic monomer having the group (2) also include the structural unit represented by the formula (a1-5) (hereinafter sometimes referred to as "structural unit (a1-5)"). TIFF2025105524000097.tif4659[In the formula (a1-5), all the symbols have the same meanings as described above.]

[0104] R in the formula (a1-5) a8Examples of the halogen atom and the alkyl group which may have a halogen atom in [reference] include the same ones as exemplified by R in Formula (a1-0) to Formula (a1-2). a01 , R a4 , R a5 as exemplified by those described above. 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 are preferably such that one of them 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-.

[0105] Examples of the structural unit (a1-5) include structural units derived from monomers described in JP-A-2010-61117. Among them, the structural units represented by Formula (a1-5-1) to Formula (a1-5-4) are preferred, and the structural unit represented by Formula (a1-5-1) or Formula (a1-5-2) is more preferred. When the TIFF2025105524000098.tif31130 resin contains the structural unit (a1-5), the content thereof 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. Also, the content 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 preferred, 3 to 45 mol% is more preferred, 5 to 40 mol% is still more preferred, and 5 to 30 mol% is even more preferred.

[0106] Examples of the structural unit having the group (1) in the structural unit (a1) include the structural unit represented by the formula (a1-6) (hereinafter sometimes referred to as "structural unit (a1-6)"). TIFF2025105524000099.tif3479[In the formula (a1-6), all the symbols have the same meanings as described above.]

[0107] R in the formula (a1-6) a61 Examples of the halogen atom and the alkyl group which may have a halogen atom in include R of the formula (a1-0) to the formula (a1-2) a01 R a4 R a5 and those similar to those exemplified by. 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 and the like. 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 still more preferably a methyl group or an ethyl group. R a62 R a63 and R a64 Examples of the cyclic hydrocarbon group in include 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, a cyclooctyl group and the like. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group and the like. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 16, more preferably 3 to 12. Examples of the aromatic hydrocarbon group include a phenylene group, a naphthylene group and the like. 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, a methacryloyloxy group, and the like. R a62 and R a63 The ring formed by bonding with each other is preferably having 3 to 12 carbon atoms. Examples of the ring include an adamantane ring, a cyclohexane ring, and the like. Specifically, when R a62 and R a63 bond with each other to form a ring, examples of -C(R a62 )(R a63 )(R a64 ) include the following groups. * represents the bonding site with an oxygen atom. TIFF2025105524000100.tif33109L a61 and L a62 Examples of the alkanediyl group having 1 to 4 carbon atoms in and L 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-*, more preferably a single bond. X a62 is preferably a single bond or *-O-L 1 -, more preferably a single bond. Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms in 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.

[0108] Examples of the halogen atom, alkyl group, alkoxy group, alkoxyalkyl group, alkoxyalkoxy group, alkylcarbonyl group, and alkylcarbonyloxy group include those similar to those exemplified in this specification.

[0109] 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. In the following structural units, the hydrogen atom corresponding to R a61 replaced by a methyl group or the like, and in the following structural units, the methyl group corresponding to R a61 replaced by a hydrogen atom are also included as the structural unit (a1-6). TIFF2025105524000101.tif226161

[0110] When the resin contains the structural unit (a1-6), the content 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. Also, 80 mol% or less is mentioned, 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%, still even more preferably 7 to 65 mol%, and particularly preferably 10 to 60 mol%.

[0111] Also, examples of the structural unit (a1) include the following structural units. TIFF2025105524000102.tif33167

[0112] When the resin contains the structural units represented by the formulas (a1-7-1) to (a1-7-7), the content 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. Also, 95 mol% or less is mentioned, 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 60 mol% or less. Specifically, it is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, still more preferably 20 to 85 mol%, still even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.

[0113] Also, examples of the structural unit (a1) include the following structural units. When the resin contains the 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, 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. 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 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.

[0114] 〈Structural unit(s)〉 The structural unit(s) is derived from a monomer having no acid-labile group (hereinafter sometimes referred to as "monomer(s)"). As the monomer that leads to the structural unit(s), a monomer having no acid-labile group known in the resist field can be used. As the structural unit(s), it is preferable to have 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 not having an acid-labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and not having an 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.

[0115] 〈Structural unit (a2)〉 The structural unit (a2) is a structural unit represented by the formula (a2) excluding the structural unit of the structural unit (a2-A), and has an alcoholic hydroxy, phenolic hydroxy group or phenolic carboxy group. TIFF2025105524000104.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 4 carbon atoms. L a21 represents a single bond 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-. L a22represents a linear hydrocarbon group having 1 to 12 carbon atoms which may have a single bond or a fluorine atom, and -CH2- contained in the linear hydrocarbon group may be replaced by -O- or -CO-. na2 represents any integer from 1 to 4.] R a2 and A a21 are the same as those exemplified for R a2 and A a21 in formula (a2 - A). The hydrocarbon group in L a21 is a (na2 + 1)-valent hydrocarbon group, and examples include linear hydrocarbon groups, alicyclic hydrocarbon groups which are monocyclic or polycyclic (including spiro rings, condensed rings, bridged rings, etc.), 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 linear hydrocarbon group) may also be used. As the linear hydrocarbon group in L a21 there may be mentioned divalent to pentavalent linear hydrocarbon groups such as alkanediyl groups, alkanetriyl groups, alkanetetrayl groups, alkanepentayl groups and the like. As the alkanediyl group in L a21 for example, there may be mentioned the same alkanediyl group as A a21 As the alkanetriyl group in L a21 there may be mentioned methanetriyl group, ethanetriyl group, propanetriyl group, butanetriyl group, pentanetriyl group, hexanetriyl group, heptanetriyl group, octanetriyl group, nonanetriyl group, decanetriyl group, undecanetriyl group, dodecanetriyl group, tridecanetriyl group, tetradecanetriyl group, pentadecanetriyl group, hexadecanetriyl group, 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, and a heptadecanetetrayl group. Examples of the alkanepentayl group include a methanepentayl group, an ethanepentayl group, a propanepentayl group, a butanepentayl group, a pentanepentayl group, and a hexanepentayl group. Examples also include a group in which one or more hydrogen atoms of the above-described group are replaced with a bonding site. L a21 The number of carbon atoms in the chain hydrocarbon group of L 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, even still more preferably 1 to 6, even still even more preferably 1 to 5, and particularly preferably 1 to 4. L a21 Examples of the monocyclic and polycyclic divalent alicyclic hydrocarbon groups in L include the following alicyclic hydrocarbon groups. The bonding site can be at any position. TIFF2025105524000105.tif46168For example, monocyclic alicyclic hydrocarbon groups such as a cyclobutane-1,3-diyl group, a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, a cyclooctane-1,5-diyl group, a cyclopropanetriyl group, a cyclobutanetriyl group, a cyclopentanetriyl group, a cyclohexanetriyl group, a cycloheptanetriyl group, a cyclooctanetriyl group, a cyclodecanetriyl group, a cyclopropanetetrayl group, a cyclobutanetetrayl group, a cyclopentanetetrayl group, a cyclohexanetetrayl group, a cycloheptanetetrayl group, a cyclooctanetetrayl group, and a cyclodecanetetrayl group, and Examples of the polycyclic alicyclic hydrocarbon group include 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, norbornanetril group, adamantanetril group, decahydronaphthalenetril group, bicyclo[3.3.0]octanetril group, norbornanetetrayl group, adamantanetetrayl group, decahydronaphthalenetetrayl group, bicyclo[3.3.0]octanetetrayl group, and the like. 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 Examples of the divalent aromatic hydrocarbon group in L include phenylene group, naphthylene group, anthrylene group, biphenylene group, phenanthrylene group, benzenetriyl group, naphthalenetriyl group, anthracenetriyl group, biphenylenetriyl group, phenanthrenetriyl group, benzenetetrayl group, naphthalenetetrayl group, anthracenetetrayl group, biphenylenetetrayl group, phenanthrenetetrayl group, and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, still more preferably 6 to 14, even more preferably 6 to 12, and still even more preferably 6 to 10. Examples of the group formed by combining two or more of them 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 of them. Also, any group may be bonded to A a21 and L a22 and may be bonded. L a21 Examples of the alkanediyl group of L may be replaced by -O- or -CO-, and La21 When the alkandiyl group of a23 -X a21 -(L a23 represents an alkandiyl 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 X a2 .), it is preferably the case. Examples of the group in which -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include a hydroxy group, a carboxy group, a thiol group, an amino group (, a carboxy group, an oxy group, a carbonyl group (, a thio group, a sulfonyl group (, an alkoxy group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfonyl group, an alkylcarbonyl group, an alkylamino group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an alkanediyl-oxy group, an alkanediyl-oxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, an alkanediylamino group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, an aromatic hydrocarbon group-carbonyl-oxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, a group formed by combining two or more of these groups, etc. Further, groups in which one or more hydrogen atoms of these groups are replaced by a bonding site, etc. are also included. 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.

[0116] Also, examples of the group in which -CH2- contained in the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and the group formed by combining the alicyclic hydrocarbon group and the aromatic hydrocarbon group is replaced by -O-, -S-, -CO-, -SO-, -NR 11 - 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. L a21The hydrocarbon group in may have one or more substituents. Examples of the substituent include a halogen atom, a haloalkyl group having 1 to 6 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-), an acryloyloxy group, a methacryloyloxy group, and the like. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. L a21 By having a halogen atom as a substituent, the hydrocarbon group in can substantially have a substituent such as a haloalkyl group. Examples of the haloalkyl group include a chloromethyl group, a bromomethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluorobutyl group, etc. A haloalkyl group having 1 to 4 carbon atoms is preferable, and a haloalkyl group having 1 to 3 carbon atoms is more preferable. L a21 By including a branched structure, the hydrocarbon group of enables a21 to substantially have a substituent 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 of the alkyl group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 4, and even still more preferably 1 to 3. L a21 Due to the group in which -CH2- contained in the hydrocarbon group of is replaced by -O- or -CO-, a21 can substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, etc. L a21Examples of the substituent that the hydrocarbon group may have include a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 6 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 preferable. 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 preferable. 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 ethoxymethoxy group is even more preferably. A fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, or a methoxy group is even more preferably. L a21 is a single bond, 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-), 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-, -S-, -CO-, -SO-, -NR 11 -, or -SO2-), or a group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group having 3 to 20 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 cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR 11 -, or -CO-). It is preferably a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (wherein -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11-Or it may be replaced by -SO2-. ) Or a group formed by combining an optionally substituted linear hydrocarbon group having 1 to 6 carbon atoms and an optionally substituted cyclic hydrocarbon group having 3 to 18 carbon atoms (however, -CH2- contained in the linear hydrocarbon group may be replaced by -O- or -CO-, and -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 11 -Or it may be replaced by -CO-. ) is more preferably the case.

[0117] L a22 Examples of the linear hydrocarbon group having 1 to 12 carbon atoms for L L a22 may have one or two or more fluorine atoms. L a22 -CH2- contained in the linear hydrocarbon group of may be replaced by -O- or -CO-, and these replaced groups may be the same as those exemplified for L a21 within the range allowed by the upper limit of the number of carbon atoms. na2 is preferably any integer from 1 to 4, and more preferably any integer from 1 to 3. La21 When the structural unit (a2) is a single bond or a chain hydrocarbon group, examples of the structural unit (a2) include the following structural units. Among the following groups, the methyl group corresponding to R a2 and the structural unit in which the methyl group is replaced by a hydrogen atom or the like are also preferred structural units of the structural unit (a2) in the same manner as the following structural units. TIFF2025105524000106.tif68168

[0118] 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 preferred, and it is more preferable to use the structural unit (a2-A). 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 preferred, and it is more preferable to use the structural unit (a2-B), the structural unit (a2-C), and the structural unit (a2-D) described below. The structural unit (a2) may be included alone or in two or more kinds.

[0119] In the structural unit (a2), L a21 When it 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 the formula (a2-B) (hereinafter sometimes referred to as the "structural unit (a2-B)"), the structural unit represented by the formula (a2-C) (hereinafter sometimes referred to as the "structural unit (a2-C)"), or the structural unit represented by the formula (a2-D) (hereinafter sometimes referred to as the "structural unit (a2-D)"). TIFF2025105524000107.tif45100[In the formula (a2-B) and the formula (a2-C), R a2 represents the same meaning as in the formula (a2). R a27 represents the same meaning as in the formula (a2-A). L a25 is -O- or *-O-(CH2) k2-CO-O- represents, and k2 represents any integer from 1 to 7. * represents the bonding position 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- (wherein f1 represents any integer from 1 to 4), and 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 a27 is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an 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.

[0120] 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 a2 which are replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group. 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. When the TIFF2025105524000108.tif80164 resin contains the structural unit (a2-B) or the formula (a2-C), the content thereof is 1 mol% or more, preferably 2 mol% or more, based on all the structural units of the resin. 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% or 2 to 20 mol%, and still more preferably 1 to 10 mol% or 2 to 10 mol%.

[0121] TIFF2025105524000109.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 a fluoroalkyl group having 1 to 4 carbon atoms. L a24represents 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 within 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 Rs a27 may be the same as or different from each other. ] R a21 and R a22 are preferably a trifluoromethyl group. L a24 Examples of the alkanediyl group of include a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-2,2-diyl group, and the like. L a24 is preferably a single bond or a methylene 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. 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. Also, preferably, nD2 is 1 and the group within the parentheses is bonded at 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.

[0122] The structural unit (a2-D) is more preferably a structural unit represented by the following formula (a2-D1) (hereinafter sometimes referred to as "structural unit (a2-D1)"). TIFF2025105524000110.tif51107[In formula (a2-D1), all symbols have the same meanings as described above.] In formula (a2-D1), R a2 is preferably a hydrogen atom or a methyl group. A a21 is preferably a single bond.

[0123] Examples of the structural unit (a2-D) include the structural units described below. TIFF2025105524000111.tif62167

[0124] In the structural units represented by formulae (a2-D-1) to (a2-D-8), the structural units in which the hydrogen atom corresponding to R a2 is replaced with a methyl group or the like, and in the structural units represented by formulae (a2-D-9) to (a2-D-16), the structural units in which the methyl group corresponding to R a2 is replaced with a hydrogen atom or the like can also be cited as specific examples of the structural unit (a2-D). Among them, 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.

[0125] When the resin contains the structural unit (a2-D), its content is preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more with respect to all the structural units of the resin. Also, it is preferably 80 mol% or less, more preferably 75 mol% or less, even more preferably 70 mol% or less, and still 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 still more preferably 10 to 65 mol%.

[0126] 〈Structural unit (a3)〉 The lactone ring contained in the structural unit (a3) may be a monocyclic ring such as a β-propiolactone ring, γ-butyrolactone ring, or δ-valerolactone ring, or may be a condensed ring of a monocyclic lactone ring and another ring. Preferably, examples thereof include a γ-butyrolactone ring, an adamantanlactone ring, or a bridged ring containing a γ-butyrolactone ring structure (for example, a structural unit represented by the following formula (a3-2)).

[0127] The structural unit (a3) is preferably a structural unit represented by formula (a3-1), formula (a3-2), formula (a3-3), or formula (a3-4). These may be contained alone or in combination of two or more. TIFF2025105524000112.tif51164[In formula (a3-1), formula (a3-2), formula (a3-3), and formula (a3-4), L a4 、L a5 and L a6 each independently represents a group represented by -O- or *-O-(CH2) k3 -CO-O- (where k3 represents an integer of 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 of 0 to 5. q1 represents an integer of 0 to 3. r1 represents an integer of 0 to 3. w1 represents an integer of 0 to 8. When p1, q1, r1 and / or w1 are 2 or more, multiple R a21 , R a22 , R a23 and / or R a25 may be the same or different.]

[0128] R a21 , R a22 , R a23 and R a25 Examples of the aliphatic hydrocarbon group in include alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, and a tert-butyl group. R a18 , R a19 , R a20 and R a24 Examples of the halogen atom and the alkyl group which may have a halogen atom in the formula (a1-0) to the formula (a1-2) include R a01 , R a4 , R a5 Examples of the above-mentioned examples are the same as those given above. L a8 and L a9 Examples of the alkanediyl group in the formula (I) include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. L a4 ~L a6is, independently of each other, 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 R a25 are each independently preferably a carboxy group, a cyano group or a methyl group. p1, q1 and r1 are each independently preferably an integer of any one of 0 to 2, more preferably 0 or 1. w1 is preferably an integer of any one of 0 to 2, more preferably 0 or 1. In particular, formula (a3-4) is preferably formula (a3-4)'. TIFF2025105524000113.tif4051 (wherein R a24 and L a7 represent the same meaning as described above.)

[0129] Examples of the structural unit (a3) include structural units derived from the monomers described in JP-A-2010-204646, JP-A-2000-122294, and 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 said structural units, R in formula (a3-1) to formula (a3-4) a18 , R a19 , R a20 and R a24 in which the methyl groups corresponding to are replaced by hydrogen atoms are preferred. When the resin contains the structural unit (a3), the total content thereof is 1 mol% or more, preferably 3 mol% or more, more preferably 5 mol% or more, still more preferably 10 mol% or more, based on all the structural units of the resin. Also, 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 1 to 65 mol%, more preferably 1 to 60 mol%, still more preferably 3 to 60 mol%. In addition, the content rate of structural unit (a3-1), structural unit (a3-2), structural unit (a3-3) or structural unit (a3-4) is preferably 1 mol% or more, more preferably 3 mol% or more, still more preferably 5 mol% or more, and even more preferably 10 mol% or more, respectively, based on all the structural units of the resin. Also, 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, even more preferably 25 mol% or less, and even more preferably 20 mol% or less. Specifically, 1 to 60 mol% is preferable, 3 to 50 mol% is more preferable, and 5 to 50 mol% is still more preferable.

[0130] 〈Structural unit (a4)〉 The structural unit represented by formula (a4) is shown below. TIFF2025105524000115.tif2770[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 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-.

[0131] R 42 The aliphatic hydrocarbon group represented by includes linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these. 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 that are monocyclic cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group; and polycyclic alicyclic hydrocarbon groups that are polycyclic cycloalkyl groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following group (* represents a bonding site). Examples of the group formed by the combination of TIFF2025105524000116.tif10146 include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic hydrocarbon group-alkyl group. 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, and a hexane-1,6-diyl group; and branched alkanediyl groups such as a propane-1,2-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a 1-methylbutane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The terminal of the branched alkanediyl group may be a methyl group. R 42 Examples of the halogen atom included in the aliphatic hydrocarbon group contained in R 42 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 contained in R 42 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 alkanediyl oxy group, an alkanediyl oxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, a cycloalkoxy group, a cycloalkylalkoxy group, and a group formed by combining two or more of these groups. These replaced groups include those similar to the groups exemplified in this specification as long as the upper limit of the number of carbon atoms permits.

[0132] As the structural unit (a4), R 42 is preferably an aliphatic hydrocarbon group having a fluorine atom, and R 42 Examples of the structural unit (a4) in which is an aliphatic hydrocarbon group having a fluorine atom include a structural unit represented by the formula (a4-1) (hereinafter sometimes referred to as "structural unit (a4-1)"), a structural unit represented by the formula (a4-2) (hereinafter sometimes referred to as "structural unit (a4-2)"), a structural unit represented by the formula (a4-3) (hereinafter sometimes referred to as "structural unit (a4-3)"), and a structural unit represented by the formula (a4-A) (hereinafter sometimes referred to as "structural unit (a4-A)"). The structural unit represented by the formula (a4-1) is the structural unit shown below. TIFF2025105524000117.tif3092[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 42f represents a hydrogen atom or a fluorine atom.]

[0133] L 41 Examples of the alkanediyl group in include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, and a butane-1,4-diyl group, and branched alkanediyl groups such as an ethane-1,1-diyl group, a propane-1,2-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group. The terminal of the branched alkanediyl group may be a methyl group. L 42fExamples of the alkanediyl group having a fluorine atom in [specific context] include linear alkanediyl groups having a fluorine atom such as a methylene group having a fluorine atom, an ethylene group having a fluorine atom, a propane-1,3-diyl group having a fluorine atom, a butane-1,4-diyl group having a fluorine atom, a pentane-1,5-diyl group having a fluorine atom, a hexane-1,6-diyl group having a fluorine atom, a heptane-1,7-diyl group having a fluorine atom, an octane-1,8-diyl group having a fluorine atom; branched alkanediyl groups having a fluorine atom such as an ethane-1,1-diyl group having a fluorine atom, a propane-1,1-diyl group having a fluorine atom, a propane-1,2-diyl group having a fluorine atom, a propane-2,2-diyl group having a fluorine atom, a pentane-2,4-diyl group having a fluorine atom, a 2-methylpropane-1,3-diyl group having a fluorine atom, a 2-methylpropane-1,2-diyl group having a fluorine atom, a pentane-1,4-diyl group having a fluorine atom, a 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 42f Examples of the cycloalkanediyl group having a fluorine atom in [specific context] include monocyclic cycloalkanediyl groups 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 cyclooctane-1,5-diyl group having a fluorine atom, and polycyclic cycloalkanediyl groups having a fluorine atom such as 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, 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 [specific context] may be 1 or more, and preferably 2 or more. L42f The alkandiyl group and cycloalkandiyl group having a fluorine atom in are preferably a perfluoroalkandiyl group and a perfluorocycloalkandiyl group, respectively.

[0134] L 42f Examples of the perfluoroalkandiyl group in 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 perfluorocycloalkandiyl group in include a perfluorocyclohexanediyl group, a perfluorocyclopentanediyl group, a perfluorocycloheptanediyl group, a perfluoroadamantanediyl group, and the like.

[0135] L 41 is preferably a single bond or an alkandiyl 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 42fis 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 still more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0136] Examples of the structural unit (a4-1) include the structural units shown below and the structural units in the structural unit (a4-1) in the following structural units where the methyl group corresponding to R 41 is replaced by a hydrogen atom. The structural unit represented by the formula (a4-2) is the structural unit shown below. TIFF2025105524000119.tif33101 [In the 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 by -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 by -O- or -CO-. However, at least one of L 43f and R 43f has a fluorine atom, and the upper limit of the total number of carbon atoms of L 43f and R 43f is 21.

[0137] Examples of the aliphatic hydrocarbon group in L 43f and R 43f include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these. Examples of the aliphatic hydrocarbon group in L 43f and R 43f are, as long as the upper limit of the total number of carbon atoms of L 43f and R 43f allows it, R in the formula (a4)42 Examples of the aliphatic hydrocarbon group of 42 include the same groups as the exemplified aliphatic hydrocarbon groups.

[0138] L 43f As the aliphatic hydrocarbon group of 43f , an alkanediyl group having 1 to 6 carbon atoms or a group represented by the formula (L43f-1) is preferable. TIFF2025105524000120.tif14120 [In the formula (L43f-1), s represents 0 or 1. L 45f and L 46f each independently represent 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 represent -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 .

[0139] Examples of the divalent aliphatic hydrocarbon group represented by L 45f 、L 46f and L 47f in the group represented by the formula (L43f-1) include linear or branched alkanediyl groups, monocyclic or polycyclic divalent alicyclic hydrocarbon groups, and divalent aliphatic hydrocarbon groups formed by combining an alkanediyl group and a divalent alicyclic hydrocarbon group. Specifically, methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, 1-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, etc. may be mentioned. s is preferably 0.

[0140] 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 -O-CO-R 43f and is the bonding site with -O-CO-R. TIFF2025105524000121.tif47140

[0141] R 43f is preferably an aliphatic hydrocarbon group having a fluorine atom. In this case, examples of the structural unit represented by formula (a4-2) include the structural units represented by formula (a4-2A) or (formula a4-2B). TIFF2025105524000122.tif41157[In formula (a4-2A) and formula (a4-2B), R 41 and L 43f represent the same as those in 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 formula (a4-2A), the total number of carbon atoms of L 43f and R 43fA is 21 or less, and in formula (a4-2B), the total number of carbon atoms of L 43f , A 43f , X 43 and R 43fB is 21 or less, and at least one of A 43f and R 43fB has at least one fluorine atom. R 43fA The aliphatic hydrocarbon group of R, 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 and includes the same aliphatic hydrocarbon groups as those exemplified by the aliphatic hydrocarbon groups in R R 43fA is preferably an alkyl group having 1 to 13 carbon atoms and having fluorine atoms, a cycloalkyl group having 3 to 12 carbon atoms and having fluorine atoms, or a group combining them, *-(CF2) n43f -R 42’ (* represents the bonding site with the carbonyl group. n43f represents any integer from 1 to 6. R 42’ represents a hydrogen atom or a fluorine atom.) or a perfluorocycloalkyl group having 3 to 12 carbon atoms is more preferable. A 43f and the aliphatic hydrocarbon group of R, 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 in formula (a4) 43fB and includes the same aliphatic hydrocarbon groups as those exemplified by the aliphatic hydrocarbon groups in R 42 and includes the same aliphatic hydrocarbon groups as those exemplified by the aliphatic hydrocarbon groups in R A 43f is preferably a divalent chain hydrocarbon group which may have fluorine atoms, a divalent alicyclic hydrocarbon group, or a group combining them, more preferably a divalent chain hydrocarbon group having fluorine atoms, and even more preferably a fluoroalkanediyl group having 1 to 6 carbon atoms. R 43fBThe aliphatic hydrocarbon group which may have a fluorine atom is preferably a chain hydrocarbon group, an alicyclic hydrocarbon group or a combination thereof which may have a fluorine atom, more preferably an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms or a combination thereof which may have a fluorine atom, and 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 alkyl fluoride 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 and the like.

[0142] 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). TIFF2025105524000123.tif14170

[0143] Examples of the structural unit represented by formula (a4-2A) include the following structural units and the structural units in which the methyl group corresponding to R in the structural unit represented by formula (a4-2A) below is replaced by a hydrogen atom. 41 TIFF2025105524000124.tif99167

[0144] ​Examples of the structural unit represented by formula (a4-2B) include the structural units shown below and the structural unit in the following structural units where the methyl group corresponding to R in the structural unit represented by formula (a4-2B) is replaced by a hydrogen atom. 41 Examples include the structural unit in which the methyl group corresponding to R in the structural unit represented by formula (a4-2B) is replaced by a hydrogen atom. TIFF2025105524000125.tif111163

[0145] Examples of the structural unit (a4) also include the structural unit represented by formula (a4-3). TIFF2025105524000126.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 the upper limit of the total number of carbon atoms of L 44f and R 44f is 21.]

[0146] Examples of the aliphatic hydrocarbon group in L 44f and R 44f include linear or branched chain aliphatic hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these. Examples of the aliphatic hydrocarbon group in L 44f and R 44f are, as long as the upper limit of the total number of carbon atoms of L 44f and R 44f allows, the same groups as the aliphatic hydrocarbon groups exemplified as the aliphatic hydrocarbon group of R 42 in formula (a4). L 44fis 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 - represented groups (j1 to j5 each independently represent an integer of 1 to 6).) is more preferable. Further, an alkanediyl group having 1 to 4 carbon atoms (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-) is even more preferable. 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, even more preferably an alkyl group having 1 to 10 carbon atoms having a fluorine atom, and still more preferably an alkyl group having 1 to 6 carbon atoms having a fluorine atom.

[0147] Examples of the structural unit represented by the 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 the structural unit (a4-3) is replaced by a hydrogen atom. 41 The structural unit obtained by replacing the methyl group corresponding to R in the structural unit (a4-3) with a hydrogen atom is mentioned. TIFF2025105524000127.tif85170

[0148] Examples of the structural unit (a4) also include a structural unit represented by the formula (a4-A). TIFF2025105524000128.tif3686[In the formula (a4-A), all the symbols have the same meaning as described above.]

[0149] R 1The alkyl group having 1 to 6 carbon atoms in [X] includes 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 [X] 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 [X] 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, and a dibromomethyl group. 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.

[0150] L 1 Examples of the aliphatic hydrocarbon group in [X] 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). Examples of the chain hydrocarbon group include a divalent to pentavalent chain hydrocarbon group 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 methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, and heptadecane-1,17-diyl group, 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, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group. Examples also include groups in which one or more hydrogen atoms of the above-described groups are replaced with a bonding site. The number of carbon atoms in 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.

[0151] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following alicyclic hydrocarbon groups. The bonding site can be at any position. TIFF2025105524000129.tif45164 For example, alicyclic hydrocarbon groups such as cycloalkanediyl groups. 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, and Polycyclic alicyclic hydrocarbon groups such as spiro rings having a cycloalkanediyl group such as a norbornane-1,4-diyl group, a norbornane-2,5-diyl group, an adamantane-1,5-diyl group, an adamantane-2,6-diyl group, a decahydronaphthalenediyl group, a bicyclo[3.3.0]octanediyl group, a spirocyclohexane-1,2'-cyclopentane-diyl group, a spiroadamantane-2,3'-cyclopentane-diyl group, etc., or a cycloalkanediyl group spiro-bonded to a norbornyl group or an adamantyl group respectively. 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.

[0152] Examples of the group combined with two or more kinds include a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group. In the combination, two or more kinds of alicyclic hydrocarbon groups and chain hydrocarbon groups may be combined respectively. Also, any group may be bonded to X 11 . Examples of the 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 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 - 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 a chain hydrocarbon group, an alicyclic 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 an alicyclic hydrocarbon group are bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - etc.), etc. * represents the bonding site with X 11 .

[0153] L 1 In the aliphatic hydrocarbon group having 1 to 28 carbon atoms of L, -CH2- may be replaced by -O-, -S-, -SO2- or -CO-. L 1 When -CH2- contained in the aliphatic hydrocarbon group of 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, an alkoxycarbonyloxy 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 the present specification within the range allowed by the upper limit of the carbon number. 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 the present specification within the range allowed by the upper limit of the carbon number.

[0154] L 1 The aliphatic hydrocarbon group in 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 (in the alkyl group or the alicyclic hydrocarbon group, -CH2- 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 group having 1 to 4 carbon atoms includes a fluoroalkyl group having 1 to 4 carbon atoms, a chloroalkyl group having 1 to 4 carbon atoms, a bromoalkyl group having 1 to 4 carbon atoms, an iodoalkyl group having 1 to 4 carbon atoms and the like. Examples of the haloalkyl group include a perfluoroalkyl group having 1 to 4 carbon atoms (such as a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a nonafluorobutyl group, etc.), a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, a 3,3,4,4,4-pentafluorobutyl group, a chloromethyl group, a bromomethyl group, an 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 a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a 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 a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group and the like. L 1Examples of the substituent that the aliphatic hydrocarbon group in [substance] may have include a halogen atom, a haloalkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, or an 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-). Preferred are a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 3 carbon atoms, 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 preferred are a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, or a methoxy group. L 1 is R 3When it does not form an alkyl fluoride group and an alicyclic hydrocarbon group, 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-), is preferred; 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-), is more preferred; 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-), is even more preferred.

[0155] R 2Examples of the C1-C8 fluoroalkyl group in [reference] 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, perfluorooctyl group. The carbon number of the fluoroalkyl group is preferably 1-6, more preferably 1-5, still more preferably 1-4, and even more preferably 1-3. R 3 In [reference], the C1-C6 fluoroalkyl group, as long as the upper limit of the carbon number permits, includes the C1-C6 fluoroalkyl groups exemplified for the fluoroalkyl group of 2 R. R 2 When 3 R is a C1-C6 fluoroalkyl group, it is preferably a C1-C6 fluoroalkyl group, more preferably a C1-C3 fluoroalkyl group, still more preferably a trifluoromethyl group, a perfluoroethyl group or a perfluoropropyl group, and even more preferably a trifluoromethyl group. R2 is R 3 When R is a hydrogen atom, it is 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 L 1 When combined with L to form an alicyclic hydrocarbon group having 3 to 6 carbon atoms, R 3 is L 1 Examples of the group formed by the combination with L include groups represented by the following formulas. In the following formulas, * and ** represent bonding sites, and the two ** represent that one represents the bonding site with a hydroxy group and the other represents the bonding site with R 2 and L 1A is L 1 is a part of the hydrocarbon group of L, and represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. TIFF2025105524000130.tif22138R 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.

[0156] 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 with 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 with a halogen atom, a haloalkyl group or an alkyl group can also be cited as specific examples of the structural unit (a4-A). TIFF2025105524000131.tif192167

[0157] When the resin has the structural unit (a4), its content is preferably 1 to 97 mol%, more preferably 2 to 95 mol%, and still more preferably 3 to 90 mol% based on all the structural units of the resin.

[0158] <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). TIFF2025105524000132.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 an aliphatic hydrocarbon group having 1 to 8 carbon atoms. L 55 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.]

[0159] 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 52 is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, more preferably an adamantyl group, a norbornyl group or a cyclohexyl group. L 55Examples of the divalent saturated hydrocarbon group in [compound name] 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 methylene group, ethylene group, propane diyl group, butane diyl group, and pentane diyl group. The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic divalent alicyclic saturated hydrocarbon group include cycloalkane diyl groups such as cyclopentane diyl group and cyclohexane diyl group. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include adamantane diyl group and norbornane diyl group.

[0160] L 55 Examples of the group in which -CH2- contained in the divalent saturated hydrocarbon group represented by L 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. TIFF2025105524000133.tif18165[In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents the bonding site with L x1 .). L x1 represents a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. L x2 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. However, the total number of carbon atoms of L x1 and L x2 is 16 or less. In formula (L1-2), L x3 represents a divalent aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms. L x4 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. However, the total number of carbon atoms of L x3 and L x4 is 17 or less. In formula (L1-3), L x5 represents a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. L x6 and L x7 each independently represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 14 carbon atoms. However, the total number of carbon atoms of L x5 , L x6 and L x7 is 15 or less. In formula (L1-4), L x8 and L x9 each represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms. W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, the total number of carbon atoms of L x8 , L x9 and W x1 is 15 or less.

[0161] L x1 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x2 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond. L x3 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x6 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x7 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x8 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. L x9 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. W x1 is preferably a divalent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, more preferably a cyclohexanediyl group or an adamantanediyl group.

[0162] Examples of the group represented by the formula (L1-1) include the following divalent groups. TIFF2025105524000134.tif36147 Examples of the group represented by the formula (L1-2) include the following divalent groups. TIFF2025105524000135.tif23130 Examples of the group represented by the formula (L1-3) include the following divalent groups. TIFF2025105524000136.tif16147 Examples of the group represented by the formula (L1-4) include the following divalent groups. TIFF2025105524000137.tif13168L 55 is preferably a single bond or a group represented by the formula (L1-1).

[0163] Examples of the structural unit (a5-1) include the following structural units and the structural units in the following structural units where the methyl group corresponding to R in the structural unit (a5-1) is replaced by a hydrogen atom. 51 are mentioned. TIFF2025105524000138.tif104151 When the resin 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.

[0164] 〈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-.

[0165] 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. TIFF2025105524000139.tif2977

[0166] 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.

[0167] 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 included. 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 a group 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 less carbon atoms is included, and more preferably a methoxycarbonyl group is included. 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.

[0168] As the sultone ring, a ring represented by the following formula (T1’) is preferable. TIFF2025105524000140.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, more preferably a methylene group. R 41 is the same as the substituent 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, more preferably 0.

[0169] Examples of the ring represented by the formula (T1’) include the following rings. The bonding site is at an arbitrary position. Among them, those having the bonding site at the 1-position or the 3-position are preferable. TIFF2025105524000141.tif44147

[0170] 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, etc. Among them, the monomer leading to the structural unit (a6) is preferably a monomer having an ethylenically unsaturated bond, more preferably a (meth)acrylic monomer.

[0171] The structural unit (a6) is preferably a structural unit represented by the formula (a6-0). TIFF2025105524000142.tif4075[In the 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.]

[0172] Examples of the halogen atom of R x include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. R x Examples of the alkyl groups of R c and R d 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 an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. R xExamples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group. R x is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and still 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 a combination of two or more of these groups may also be used. Specifically, linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a 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, a heptadecane-1,17-diyl group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group; branched alkanediyl groups such as a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group; monocyclic divalent alicyclic saturated hydrocarbon groups which are cycloalkanediyl groups such as a cyclobutane-1,3-diyl group, a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, and a cyclooctane-1,5-diyl group; Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include a norbornane-1,4-diyl group, a norbornane-2,5-diyl group, an adamantane-1,5-diyl group, an adamantane-2,6-diyl group, and the like. A x The bonding position to the sultone ring of A can be an arbitrary position, but the position at the 1-position is preferred.

[0173] Examples of the structural unit (a6-0) include the following structural units. TIFF2025105524000143.tif93150

[0174] Among them, the structural units represented by the formula (a6-1), the formula (a6-2), the formula (a6-6), the formula (a6-7), the formula (a6-8), and the formula (a6-12) are preferred, and the structural units represented by the formula (a6-1), the formula (a6-2), the formula (a6-7), and (a6-8) are more preferred. When the resin has 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.

[0175] <Structural unit (a7)> The resin 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 a structural unit having a sulfonate group or a carboxylate group and an organic cation in the side chain or a structural unit having a sulfonio group and an organic anion in the side chain is preferred. 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). TIFF2025105524000144.tif26117[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 a71represents 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 bond. * and ** represent bonding sites, and * represents the bonding site with the carbon atom to which R a7 is bonded. L a71 and L a72 each independently represent 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-, and *** represents the bonding site with L a71 na7 represents any integer from 0 to 2. When na7 is an integer of 2 or more, the groups in the plurality of parentheses may be the same or different from each other. RA - represents a sulfonate anion or a carboxylate anion. ZA + represents an organic cation.]

[0176] R a7 and R a71 Examples of the alkyl group having 1 to 6 carbon atoms in 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 a7 Examples of the halogen atom in include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.​ R a7 Examples of the alkyl group having 1 to 6 carbon atoms and a halogen atom in R include trifluoromethyl group, difluoromethyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, perfluorohexyl group, trichloromethyl group, dichloromethyl group, triiodomethyl group, diiodomethyl group, tribromomethyl group, dibromomethyl group and the like. 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 still more preferably a hydrogen atom or a methyl group.

[0177] X a71 When X is a group represented by *-Ax-Ph-Ay-*, it is preferably a linking group represented by the following formula (X10). TIFF2025105524000145.tif3351[In the formula (X10), Ax represents a 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 a bonding species that binds to L a71 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. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms or an alkoxy group having 1 to 6 carbon atoms. mx represents any integer from 0 to 4, and when mx is an integer of 2 or more, a plurality of Rx may be the same as or different from each other.] When either Ax or Ay is a single bond, the other is preferably at least one selected from the group consisting of an ether bond, a thioether bond, an ester bond, a carbonate bond, and an amide bond. When either of Ax and Ay is an amide bond, the bond represented by -CO-NR a71 - is preferred. The bonding position of Ay in the phenylene group is preferably the m-position or the p-position, more preferably the p-position, relative to the bonding position of Ax. Among others, 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 As, for example, a single bond, the following formula (X 10 -1) to formula (X 10 -10) represent the groups. * 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 -. TIFF2025105524000146.tif43162 The specific examples of the groups represented by formula (X 10 -1) to formula (X 10 -10) include the following groups. TIFF2025105524000147.tif87163 Among others, X 10 is preferably a single bond or a group represented by formula (X 10 -1’) and formula (X 10 -3’) to formula (X 10 -10’), more preferably a single bond or a group represented by formula (X 10 -1’), formula (X 10 -4’), formula (X 10 -5’), formula (X 10 -6’), and formula (X 10 -10’), still more preferably a single bond, a group represented by formula (X 10 -1’), a group represented by formula (X 10 -5’), or formula (X10 It is more preferable that it is a group represented by -6’).

[0178] L a71 As the hydrocarbon group of L, one hydrogen atom is removed from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups, and X a71 and X a72 and a group bonded to X a72 As the hydrocarbon group of L, one hydrogen atom is removed from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups, and X a72 and RA - and a group bonded to RA L a71 and L a72 As the chain hydrocarbon group of L and L, a group obtained by removing one hydrogen atom from an alkyl group or an alkenyl group can be mentioned. The alkyl group may be linear or branched, and specifically, methyl group, ethyl group, 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, decanyl group, undecanyl group, dodecanyl group, tridecanyl group, tetradecanyl group, pentadecanyl group, heptadecanyl group, etc. can be mentioned. As the alkenyl group, 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 can be mentioned. The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 36, more preferably 1 to 20, and even more preferably 1 to 10. L a71 and L a72 As the alicyclic hydrocarbon group of L and L, a group obtained by removing one hydrogen atom from a monocyclic or polycyclic cycloalkyl group can be mentioned. As the monocyclic cycloalkyl group, cyclobutyl group, cyclopentane group, cyclohexane group, cyclopentyl group, cyclooctyl group, etc. can be mentioned. L a71 and La72 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 and an adamantanyl group. Examples of the cycloalkyl group in which two or more rings are condensed include a bicyclo[4.4.0]decanyl group and a steroid group (steroid skeleton). Examples of the ring in which two rings are spiro-bonded include a spirocycloalkyl 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 is spiro-bonded to a cycloalkyl group having 5 to 8 carbon atoms. Also, a double bond may be formed between two carbon atoms included in the alicyclic hydrocarbon group. More specifically, examples of the alicyclic hydrocarbon group represented by the following formula can be given. TIFF2025105524000148.tif28158 When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 12, more preferably 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms of the alicyclic hydrocarbon group is preferably 7 to 12. L a71 and L a72 Examples of the aromatic hydrocarbon group of and L include an aryl group from which one hydrogen atom has been removed. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a fluorene group. The number of carbon atoms of the aromatic hydrocarbon group is preferably 5 to 14, more preferably 5 to 10. L a71 and L a72 When -CH2- included 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 a72Among 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 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, etc. These replaced groups include those similar to the above-mentioned ones within the range allowed by the upper limit of the number of carbon atoms. L a71 and L a72 Among 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 a cyclic ether, a cyclic ketone, a cyclic ester (lactone), a cyclic thioether, a cyclic acetal, a cyclic sultone, 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. TIFF2025105524000149.tif46146L a71 and L a72 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 a furan ring or a thiophene ring, respectively. L a71 and L a72 Examples of the group formed by combining two or more of the chain hydrocarbon group, alicyclic hydrocarbon group and aromatic hydrocarbon group include the group formed by combining the above-mentioned chain hydrocarbon group and the above-mentioned alicyclic hydrocarbon group, the group formed by combining the above-mentioned chain hydrocarbon group and the above-mentioned aromatic hydrocarbon group, the group formed by combining the above-mentioned alicyclic hydrocarbon group and the above-mentioned aromatic hydrocarbon group, and the group formed by combining the above-mentioned chain hydrocarbon group, the above-mentioned alicyclic hydrocarbon group and the above-mentioned aromatic hydrocarbon group. The group formed by combining the above-mentioned groups can be mentioned. The group formed by combining the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be a condensed ring. 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-, -CO-, -S- or -SO2- include the same groups as those exemplified in the present specification within the range allowed by the upper limit of the number of carbon atoms. L a71 and L a72 Examples of the substituent that the hydrocarbon group of a71 and a72 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 a71 and a72 are a group combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group, substantially, the chain hydrocarbon group may be regarded as a substituent that the alicyclic hydrocarbon group or the aromatic hydrocarbon group has. Also, when a71 and L a72 the -CH2- of the chain hydrocarbon group contained in the hydrocarbon group of a71 and a72 is replaced by -O-, -CO-, -S- or -SO2-, a71 and L a72 the hydrocarbon group of a71 and a72 can substantially have substituents such as a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, a thiol group, and a sulfonyl group. ZA in formula (a7-A) + includes the same ones as the cation Z1 in the salt represented by the above-described formula (B1). +

[0179] Examples of the structural unit represented by formula (a7-A) include, for example, the following structural units, groups corresponding to the methyl group of R a7 in which the group corresponding to the methyl group of a7 is replaced by a hydrogen atom, a halogen atom (for example, a fluorine atom), or an alkyl group having 1 to 6 carbon atoms that may have a halogen atom (for example, a trifluoromethyl group, etc.), and the structural units described in International Publication No. 2012 / 050015. ZA + represents an organic cation. TIFF2025105524000150.tif244163

[0180] ​ TIFF2025105524000151.tif131157

[0181] 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). TIFF2025105524000152.tif28104[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 combine with each other to form a ring together with the sulfur atom to which they are attached. 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 atoms and alkyl groups 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 are the same as those described above. A b7Examples of the divalent linking group represented by include divalent saturated hydrocarbon groups 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 linear or branched alkanediyl groups, monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups, or combinations thereof. Specific examples 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; 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; cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group; and divalent polycyclic alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group. 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 formulas, * and ** represent bonding sites, and * represents the bonding site with R b71 and represents the bonding site with R. TIFF2025105524000153.tif123161[wherein 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 5represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms. X 6 represents a divalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 7 represents a trivalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 8 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.

[0182] Examples of the structural unit containing the cation in the formula (a7-B) include the structural unit represented by the following and a group corresponding to the methyl group of R a7 in which the methyl group is replaced with a hydrogen atom, a halogen atom (for example, a fluorine atom), or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (for example, a trifluoromethyl group, etc.). TIFF2025105524000154.tif75163

[0183] A - Examples of the organic anion represented by include sulfonate anions, sulfonylimide anions, and sulfonylmethide anions. A - The organic anion represented by is preferably a sulfonate anion, and more preferably an anion contained in the salt represented by the above formula (B1). Examples of the sulfonylimide anion, sulfonylmethide anion, and carboxylate anion are the same as those exemplified as the anions of the acid generator (B) and the salt represented by the formula (B3).

[0184] Examples of the structural unit represented by the formula (a7-B) include the structural unit represented by the following. TIFF2025105524000155.tif95157

[0185] When the resin contains the structural unit (a7), the structural unit (a7) may be contained alone or in combination of two or more. The total content of the structural unit (a7) is preferably 1 to 30 mol%, more preferably 2 to 25 mol%, still more preferably 3 to 20 mol%, and even more preferably 3 to 15 mol% based on all the structural units of the resin.

[0186] The resin contained in the resist composition of the present invention is preferably a resin containing the structural unit (a2-A) and / or the structural unit (a1-4). Each structural unit constituting the resin 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 lead to these structural units. The content of each structural unit of the resin can be adjusted by the amount of the monomers used in the polymerization. The weight average molecular weight of the resin is preferably 2,000 or more (more preferably 2,500 or more, still more preferably 3,000 or more), and 50,000 or less (more preferably 30,000 or less, still more preferably 15,000 or less). In this specification, the weight average molecular weight is the value determined by gel permeation chromatography under the conditions described in the examples. In the resist composition of the present invention, when the resin is contained, the total content of the resin is preferably 1 mass% or more and 80 mass% or less, more preferably 3 mass% or more and 60 mass% or less, and still more preferably 5 mass% or more and 50 mass% or less based on the solid content of the resist composition. The solid content of the resist composition and the content of the resin relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0187] <Other Resins> The resist composition of the present invention may further contain a resin regardless of the presence or absence of a resin such as a phenolic hydroxyl group-containing compound (L). Examples of such resins include resins that do not contain a structural unit represented by formula (a2-A) and a structural unit represented by formula (a1-4), for example, a resin that contains a structural unit (a1) and does not contain a structural unit (a2) (hereinafter sometimes referred to as resin (AA)), a resin that contains a structural unit (a4) and / or a structural unit (a5) (hereinafter sometimes referred to as resin (X)), and the like. In addition to the structural unit (a1), resin (AA) may contain a structural unit (a3), a structural unit (a4), a structural unit (a5), a structural unit (a6), a structural unit (a7), and the like. Also, in resin (AA), the content ratio of each of the structural unit (a1), the structural unit (a3), the structural unit (a4), the structural unit (a5), the structural unit (a6), and / or the structural unit (a7) may be the same as the content ratio with respect to all the structural units of the resin described above.

[0188] Among resins (X), a resin containing a structural unit (a4) is preferable. That is, it is preferably a resin containing a structural unit having a fluorine atom. Examples of the structural unit that resin (X) may further have include a structural unit (a3), a structural unit (a6), a structural unit (a7), and a structural unit derived from other known monomers. Among them, resin (X) is preferably a resin composed only of a structural unit (a4) and / or a structural unit (a5), and more preferably a resin composed only of a structural unit (a4). 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, still more preferably 45 mol% or more, based on the total of all the structural units of the resin (X). Further, 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, still more preferably 45 mol% or more, based on the total of all the structural units of the resin (X). Further, 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, still more preferably 80 mol% or more, based on the total of all the structural units of the resin (X). Further, it is 100 mol% or less. Specifically, it is 40 to 100 mol%, preferably 60 to 100 mol%, more preferably 70 to 100 mol%, still more preferably 80 to 100 mol%. Further, the content of the structural unit (a2) which may be further contained is 1 to 45 mol%, preferably 2 to 30 mol%, more preferably 2 to 20 mol%, based on the total of all the structural units of the resin (X).

[0189] Each structural unit constituting the resin (AA) and 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 monomers that induce these structural units. The content of each structural unit of the resin (AA) and the resin (X) can be adjusted by the amount of monomers used in the polymerization. The weight average molecular weight of the resin (AA) is preferably 2,000 or more (more preferably 2,500 or more, still more preferably 3,000 or more) and 50,000 or less (more preferably 30,000 or less, still more preferably 15,000 or less). 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). The means for measuring the weight average molecular weight of the resin (AA) and the resin (X) is the same as that for the resin. When the resist composition contains the resin (AA) and / or the resin (X), the 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 2 to 30 parts by mass, and still even more preferably 2 to 8 parts by mass, respectively, based on 100 parts by mass of the resin.

[0190] <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.

[0191] <Quencher (C)> The quencher (C) includes basic nitrogen-containing organic compounds or salts that generate an acid having a lower acidity than the acid generated from the acid generator (acid generator (B)) (excluding the phenol salts represented by formula (I)). 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 compounds 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 and the like. Aromatic amines such as diisopropylaniline are preferred, and 2,6-diisopropylaniline is more preferred. 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.

[0192] 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. Preferably, it is a salt that generates a carboxylic acid with a lower acidity than the acid generated from the acid generator (a salt having a carboxylic acid anion), more preferably a weak acid inner salt (D), and still more preferably a diphenyliodonium salt containing a phenyl group substituted with a carboxylic acid anion among the weak acid inner salts (D). TIFF2025105524000156.tif97153

[0193] 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, salts represented by the following formula are included. TIFF2025105524000157.tif1874[In formula (D), R D1 and R D2 each independently represents a hydrocarbon group having 1 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 7 carbon atoms, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a nitro group or a halogen atom. m' and n' each independently represent an integer of any one of 0 to 4. When m' is 2 or more, a plurality of R D1 may be the same or different, and when n' is 2 or more, a plurality of R D2 may be the same or different.] R D1 and R D2 Examples of the hydrocarbon group include a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these. 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 and the like. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and may be either saturated or unsaturated. Examples thereof include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclononyl group, cyclododecyl group, norbornyl group, adamantyl group and the like. 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 and the like. Groups 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 groups in which an oxy group (-O-) is bonded to the above acyl group, etc. Examples of the alkoxycarbonyl group include groups 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, and 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.

[0194] More specifically, the following salts are included. TIFF2025105524000158.tif72166

[0195] 〈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.

[0196] 〈Preparation of Resist Composition〉 The resist composition of the present invention can be prepared by mixing salt (I), acid generator (B), and, if necessary, a resin containing compound (L) or a structural unit derived from these compounds, resin (A), a resin other than resin (A), solvent (E), 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 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 with a pore size of about 0.003 to 0.2 μm.

[0197] 〈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 using 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 formed on the surface. Before applying the resist composition, the substrate may be washed, or an antireflection film, etc. may be formed on the substrate. By drying the applied 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 KrF excimer laser (wavelength 248 nm), ArF excimer laser (wavelength 193 nm), F2 excimer laser (wavelength 157 nm), those that convert laser light from a solid laser light source (YAG or semiconductor laser, etc.) 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 at 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 developer in a developing device. Examples of the developing method include dip method, paddle method, spray method, dynamic dispense method, etc. The developing temperature is preferably, for example, 5 to 60 °C, and the developing time is preferably, for example, 5 to 300 seconds. By selecting the type of developer as follows, a positive resist pattern or a negative resist pattern can be manufactured. When 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, an aqueous solution 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 moisture. 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.

[0198] <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, particularly as a resist composition for electron beam (EB) exposure or a resist composition for EUV exposure, and is useful for microfabrication of semiconductors.

Examples

[0199] The present invention will be described more specifically with reference to examples. In the examples, “%” and “parts” representing the content or the amount used are based on mass unless otherwise specified. The weight average molecular weight is a value determined by gel permeation chromatography. The analysis conditions for gel permeation chromatography are as follows. Column: TSKgel Multipore HXL-M x 3 + guard column (manufactured by Tosoh Corporation) Eluent: Tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI detector Column temperature: 40 °C Injection volume: 100 μl Molecular weight standard: Standard polystyrene (manufactured by Tosoh Corporation) The structure of the compound was confirmed by measuring the molecular ion peak using mass spectrometry (LC is Agilent 1100 type, MASS is Agilent LC / MSD type). In the following examples, the value of this molecular ion peak is indicated by “MASS”.

[0200] Example 1: Synthesis of the salt represented by formula (I-1) 1.25 parts of the compound represented by formula (I-1-a), 10 parts of acetonitrile and 5 parts of ion-exchanged water were mixed and stirred at 23 °C for 30 minutes. Then, 0.31 part of sodium hydroxide was added, and the mixture was further stirred at 23 °C for 1 hour. To the resulting reaction mixture, 2.09 parts of the salt represented by formula (I-1-b), 30 parts of chloroform and 10 parts of ion-exchanged water were added, and the mixture was stirred at 23 °C for 1 hour. After liquid separation, the organic layer was taken out. 15 parts of ion-exchanged water were added to the obtained organic layer, 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. The obtained organic layer was concentrated, 10 parts of tert-butyl methyl ether was added to the concentrated residue, and the mixture was stirred at 23 °C for 30 minutes. Then, the supernatant was removed and concentrated to obtain 0.68 part of the salt represented by formula (I-1). MASS(ESI(+)Spectrum):M + 263.1 MASS(ESI(-)Spectrum):M - 195.1

[0201] Example 2: Synthesis of the salt represented by formula (I-2) 1.96 parts of the compound represented by formula (I-2-a), 20 parts of acetonitrile and 10 parts of ion-exchanged water were mixed and stirred at 23 °C for 30 minutes. Then, 0.40 part of sodium hydroxide was added, and the mixture was further stirred at 23 °C for 1 hour. To the resulting reaction mixture, 2.99 parts of the salt represented by formula (I-1-b), 50 parts of chl...

Claims

1. A phenol generator containing a phenol salt represented by formula (I). [In formula (I), R ４ represents a halogen atom or a hydrocarbon group having 1 to 72 carbon atoms, and the hydrocarbon group is *-O － (* represents the bonding site with R ４ and may have a substituent. The -CH 2 - contained in the hydrocarbon group may be replaced by -O- or -CO-, -S-, -SO ２ -. R ５ represents an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms. m4 represents any integer from 0 to 4, and when m4 is 2 or more, a plurality of Rs ４ may be the same as or different from each other. m5 represents any integer from 1 to 4, and when m5 is 2 or more, the plurality of Rs ５ may be the same as or different from each other. However, 1 ≤ m4 + m5 ≤ 5. Z ＋ represents an organic cation. m2 represents any integer from 1 to 8, and when m2 is 2 or more, the plurality of Z ＋ may be the same as or different from each other.]

2. m4 is an integer of 1 or more, R of 1 or more ４ One of them is an alkyl group having 1 to 6 carbon atoms (—CH contained in the alkyl group 2 — may be replaced by —O— or —CO—, —S—, —SO ２ —). The phenol generator according to claim 1.

3. m4 is an integer of 1 or more, R of 1 or more ４ One of them is a hydrocarbon group containing a benzene ring bonded to at least one group selected from *-O － , a hydroxy group, an alkoxyalkyl group having 2 to 6 carbon atoms, and a hydroxyalkyl group having 1 to 6 carbon atoms, and the benzene ring is *-O － , a hydroxy group, an alkoxy group having 2 to 6 carbon atoms, and a phenol generator according to claim 1 which may have a substituent other than a hydroxyalkyl group having 1 to 6 carbon atoms.

4. m4 is an integer of 1 or more, R of 1 or more ４ The phenol generator according to claim 1, wherein one of them is a group represented by any one of formula (R4-1) to formula (R4-5). [In formulas (R4-1) to (R4-5), R ４Ａ represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. R ５Ａ represents an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms. m4A, m4B, and m4C each independently represent any integer from 0 to 4, and when m4A + m4B + m4C is 2 or more, a plurality of Rs ４Ａ may be the same as or different from each other. m5A, m5B, and m5C each independently represent an integer from 1 to 4, satisfy 1 ≦ m4A + m5A ≦ 4, 1 ≦ m4B + m5B ≦ 4, and 1 ≦ m4C + m5C ≦ 4, and a plurality of Rs ５Ａ may be the same as or different from each other. R ６Ａ and R ６Ｂ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R ７ represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. m7 represents any integer from 0 to 4. L １ , L １Ａ and L １Ｂ each independently represents a single bond, a methylene group, a methylmethylene group, a dimethylmethylene group, a carbonyl group or a sulfonyl group. X １ represents a hydroxy group or *-O － . * represents the bonding site with the benzene ring. The total number of carbon atoms contained in each group represented by formulas (R4-1) to (R4-5) does not exceed 60.]

5. A resist composition containing the phenol generator according to any one of Claims 1 to 4 and an acid generator other than the phenol generator.

6. The resist composition according to Claim 5, wherein the acid generator contains a salt represented by formula (B1) or a salt represented by formula (B3). [In formula (B1), L b1 represents a (nb1 + 1)-valent hydrocarbon group which may have a single bond or substituents, and the -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -. L b2 represents a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a single bond or a substituent, and -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -. 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 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-. nb1 represents any integer from 1 to 6. When nb1 is 2 or more, the groups in the plurality of parentheses may be the same or different from each other. Z1 ＋ represents an organic cation.] [In formula (B3), A １ represents a nitrogen atom or a carbon atom. L ｂ２ ' represents a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a single bond or a substituent, and -CH 2 - may be replaced by -O-, -S-, -CO- or -SO 2 -. 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 contained in the cyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -SO 2 - or -CO-, and two -SO 2 -L ｂ２’ -Y ｂ１’ may combine together to form a ring containing A １ and may be formed. nb5 represents 2 or 3. When nb5 is 2, A １ represents a nitrogen atom, and when nb5 is 3, A １ represents a carbon atom. The groups within the plurality of parentheses may be the same as or different from each other. Z2 ＋ represents an organic cation.

7. Furthermore, the resist composition according to Claim 5, which further contains a compound having a phenolic hydroxyl group or a benzoic acid carboxy group and / or a compound in which the hydroxyl group of the phenolic hydroxyl group or the carboxy group of the benzoic acid carboxy group is protected by an acid-labile group.

8. The resist composition according to Claim 5, wherein the compound is a resin, and the resin contains a resin containing a structural unit represented by formula (a2-A) or a structural unit represented by formula (a1-4). [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 -CH ２ - 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 any integer from 1 to 5. When nA2 is 2 or more, the groups in the plurality of parentheses may be the same or different from each other. na21 represents any integer from 0 to 4, and when na21 is 2 or more, a plurality of Rs ａ２７ may be the same as or different from each other. mc represents any integer from 0 to 2.] [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 -CH ２ - 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 represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and 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 -CH 2 - in the hydrocarbon group and the divalent hydrocarbon group may be replaced by -O- or -S-. na1 represents any integer from 1 to 5. When na1 is 2 or more, the groups in the plurality of parentheses may be the same or different from each other. na11 represents any integer from 0 to 4, and when na11 is 2 or more, a plurality of Rs ａ１７ may be the same as or different from each other. mc represents any integer from 0 to 2.]

9. The resin further includes a structural unit having an acid-labile group other than the structural unit represented by formula (a1-4), and the structural unit having an acid-labile group other than the structural unit represented by formula (a1-4) includes at least one selected from the group consisting of the structural unit represented by formula (a1-0), the structural unit represented by formula (a1-1), the structural unit represented by formula (a1-2), the structural unit represented by formula (a1-5), and the structural unit represented by formula (a1-6). The resist composition according to claim 8. [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L ａ１ and L ａ２ each independently represents -O- or *-O-(CH ２ ), ｋ１ -CO-O-, k1 represents any integer from 1 to 7, and * represents the bonding site with -CO-. R a01 , R ａ４ and R ａ５ each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, 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. ] [In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. Z a1 represents a single bond or *-(CH 2 ) h3 -CO-L 54 -, h3 represents an integer from 1 to 4, and * represents the bonding site with 51 L. L 51 , L 52 , L 53 and L 54 each independently represents -O- or -S-. s1 represents an integer of any one of 1 to 3. s1′ represents an integer of any one 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 represents a single bond, -CO-O-*, or -CO-NR a65 -*, where * represents a bond to 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 -, where * represents a bond to 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. ]

10. (1) A step of applying the resist composition according to claim 5 onto a substrate, (2) A step of drying the applied composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the exposed composition layer, and (5) A step of developing the heated composition layer, A method for manufacturing a resist pattern including these steps.

11. A phenol salt represented by formula (I). [In formula (I), R ４ represents a halogen atom or a hydrocarbon group having 1 to 72 carbon atoms, and the hydrocarbon group is *-O － (* represents the bonding site with R ４ and may have a substituent. The -CH 2 - contained in the hydrocarbon group may be replaced by -O- or -CO-, -S-, -SO ２ -. R ５ represents an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms. m4 represents any integer from 0 to 4, and when m4 is 2 or more, the plurality of Rs ４ may be the same as or different from each other. m5 represents any integer from 1 to 4, and when m5 is 2 or more, the plurality of Rs ５ may be the same as or different from each other. However, 1 ≦ m4 + m5 ≦ 5. Z ＋ represents an organic cation. m2 represents any integer from 1 to 8, and when m2 is 2 or more, the plurality of Z ＋ may be the same as or different from each other.]

12. m4 is an integer of 1 or more, R of 1 or more ４ One of them is an alkyl group having 1 to 6 carbon atoms (in the alkyl group, -CH 2 - may be replaced by -O-, -CO-, -S-, -SO ２ -.). The phenol salt according to claim 11.

13. m4 is an integer of 1 or more, R of 1 or more ４ One of them is a hydrocarbon group containing a benzene ring bonded to at least one group selected from *-O － , a hydroxy group, an alkoxyalkyl group having 2 to 6 carbon atoms, and a hydroxyalkyl group having 1 to 6 carbon atoms, and the benzene ring is *-O － , a hydroxy group, an alkoxy group having 2 to 6 carbon atoms, and a phenol salt according to claim 11 which may have a substituent other than a hydroxyalkyl group having 1 to 6 carbon atoms.

14. m4 is an integer of 1 or more, R of 1 or more ４ The phenol salt according to claim 11, wherein one of them is a group represented by any one of formula (R4-1) to formula (R4-5). [In formula (R4-1) to formula (R4-5), R ４Ａ represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. R ５Ａ represents an alkoxyalkyl group having 2 to 6 carbon atoms or a hydroxyalkyl group having 1 to 6 carbon atoms. m4A, m4B, and m4C each independently represent an integer of any one of 0 to 4, and when m4A + m4B + m4C is 2 or more, a plurality of Rs ４Ａ may be the same as or different from each other. m5A, m5B, and m5C each independently represent an integer from 1 to 4, satisfy 1 ≦ m4A + m5A ≦ 4, 1 ≦ m4B + m5B ≦ 4, and 1 ≦ m4C + m5C ≦ 4, and a plurality of Rs ５Ａ may be the same as or different from each other. R ６Ａ and R ６Ｂ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R ７ represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 6 carbon atoms. m7 represents an integer of any one of 0 to 4. L １ , L １Ａ and L １Ｂ each independently represents a single bond, a methylene group, a methylmethylene group, a dimethylmethylene group, a carbonyl group or a sulfonyl group. X １ represents a hydroxy group or *-O － and is as defined above. * represents a bonding site with the benzene ring. The total number of carbon atoms contained in each group represented by formula (R4-1) to formula (R4-5) does not exceed 60. ]

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