Resist composition and method for producing resist pattern
The resist composition, featuring specific structural units, enhances line edge roughness in resist patterns, overcoming the challenges faced by existing compositions.
Patent Information
- Application Number
- JP2024206434
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-11-29
- Filing Date
- 2024-11-27
- Publication Date
- 2025-06-10
AI Technical Summary
Existing resist compositions struggle to produce resist patterns with improved line edge roughness (LER).
A resist composition comprising a resin with structural units represented by formulas (I), (II-x), and an acid-labile group, which are specifically designed to enhance the formation of resist patterns with better LER.
The resist composition effectively produces resist patterns with improved line edge roughness, addressing the limitations of existing technologies.
Smart Images

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Abstract
Description
Technical Field
[0001] The present invention relates to a resist composition, a method for producing a resist pattern using the resist composition, and the like.
Background Art
[0002] Patent Document 1 describes a resist composition containing a resin having the following structural unit and a structural unit having an acid-labile group. TIFF2025087629000001.tif3740
[0003] Patent Document 2 describes a resist composition containing a resin having the following structural unit and a structural unit having an acid-labile group. JPEG2025087629000002.jpg2421
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 resist composition that forms a resist pattern with better line edge roughness (LER) than a resist pattern formed by the above resist composition.
[0006] The present invention includes the following inventions. [1] A resist composition containing a resin including a structural unit represented by formula (I), a structural unit having a group represented by formula (II-x), and a structural unit having an acid-labile group. TIFF2025087629000003.tif3488[In formula (I), X 0 represents a hydrocarbon group having 1 to 72 carbon atoms which may have a single bond or a substituent, and the -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -. L 10 represents a hydrocarbon group having 1 to 36 carbon atoms which may have a single bond or a substituent, and the -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-. R 10 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. X 10 represents a single bond, *-O-**, *-CO-O-**, *-O-CO-O-**, *-CO-NR 3 -**, *-NR 3 -CO-O-**, *-O-CO-NR 3 -** or *-Ax-Ph-Ay-**. R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ph represents a phenylene group which may have a substituent. Ax and Ay each independently represent one or more bond types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond and a carbonate ester bond. * and ** represent bonding sites, and * represents the bonding site with the carbon atom to which R 10 is bonded. Z1 + represents an organic cation.] TIFF2025087629000004.tif2958[In formula (II-x), ring W 1 represents a heterocyclic ring having 2 to 36 carbon atoms, and the hydrogen atoms contained in the heterocyclic ring may be substituted with a halogen atom or a hydrocarbon group having 1 to 24 carbon atoms, and the -CH 2 - contained in the heterocyclic ring and the hydrocarbon group may be replaced by -O-, -S-, -CO- or -NR c- may be replaced by R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. * represents a bonding site. [2]X 10 is a single bond or a group represented by formula (X 10 - 1) to formula (X 10 - 10) according to [1] of the resist composition. TIFF2025087629000005.tif43162[In formula (X 10 - 1) to formula (X 10 - 10), *, ** are bonding sites, and * is the bonding site with the carbon atom to which R 10 is bonded. 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. X 20 is -O- or -NR 3 -. R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. [3]L 10 is a single bond, an optionally substituted chain hydrocarbon group having 1 to 10 carbon atoms (provided that -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms (provided that -CH 2 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), or a group formed by combining an optionally substituted chain hydrocarbon group having 1 to 8 carbon atoms and an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms (provided that -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH 2 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO 2-or may be replaced by -CO-. The resist composition according to [1] or [2]. [4]X 0 is a single bond, a chain hydrocarbon group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, a group combining an alicyclic hydrocarbon group having 3 to 36 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group combining an aromatic hydrocarbon group having 6 to 36 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms, The -CH 2 - in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -. The chain hydrocarbon group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. The resist composition according to any one of [1] to [3]. [5] The resist composition according to any one of [1] to [4], wherein the structural unit having a group represented by formula (II-x) is a structural unit represented by formula (IIA). TIFF2025087629000006.tif4056 [In formula (IIA), ring W 1 represents the same meaning as formula (II-x). 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 X is a single bond, -A X1 -* or -CO-O-A X1 -* (* represents the bonding site with the carbonyl group). A X1 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH 2 - in the saturated hydrocarbon group may be replaced by -O-, -CO- or -N(R d ). R d represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. [6] The resist composition according to any one of [1] to [5], wherein the structural unit having an acid-labile group contains at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), a structural unit represented by formula (a1-2), a structural unit represented by formula (a1-4), a structural unit represented by formula (a1-5), and a structural unit represented by formula (a1-6). TIFF2025087629000007.tif44140In 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 an integer of 1 to 7, and * represents the bonding site with -CO-. R a01 、R a4 and R a5 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 、R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these, and the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. R a6 and R a7 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. m1 represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1’ represents an integer of 0 to 3.] TIFF2025087629000008.tif31119[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 - contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a18 -. R a18 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a1 represents a single bond or a carbonyl group. R a34 and R a35 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R a36 represents a hydrocarbon group having 1 to 20 carbon atoms, or R a35 and R a36 are bonded to each other to form a divalent hydrocarbon group having 2 to 20 carbon atoms together with the -C-O- to which they are bonded, and -CH 2 - contained in the hydrocarbon group and the divalent hydrocarbon group may be replaced by -O- or -S-. na1 represents any integer from 1 to 5, and when na1 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. na11 represents any integer from 0 to 4, and when na11 is 2 or more, the plurality of R a17 may be the same as or different from each other. mc represents any integer from 0 to 2.] TIFF2025087629000009.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 *-(CH 2 ) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, and * represents the bonding site with L 51 . L 51 , L 52 , L 53 and L 54 each independently represent -O- or -S-. s1 represents an integer of 1 to 3. s1’ represents an integer of 0 to 3. ] TIFF2025087629000010.tif3479[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 represent an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, or R a62 and R a63 are bonded to each other to form a ring having 3 to 20 carbon atoms together with the carbon atom to which they are bonded. X a61 represents a single bond, -CO-O-* or -CO-NR a65 -*, * represents the bonding site with Ar, and R a65 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 represents a single bond, *-O-L a61 - or *-CO-O-L a62 -, * represents the bonding site with Ar, and L a61 and L a62 each independently 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. [7] The resist composition according to any one of [1] to [6], wherein the resin further contains a structural unit represented by formula (a2-A). TIFF2025087629000011.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 -CH 2 - 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, and when nA2 is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. na21 represents any integer from 0 to 4, and when na21 is 2 or more, a plurality of R a27 may be the same as or different from each other. mc represents any integer from 0 to 2. [8] The resist composition according to any one of [1] to [7], further containing an acid generator, wherein the acid generator contains a salt represented by formula (B1). TIFF2025087629000012.tif1392 [In formula (B1), L b1represents a (nb1 + 1)-valent hydrocarbon group which may have a single bond or a substituent, and -CH contained in the hydrocarbon group 2 - 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 contained in the hydrocarbon group 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-. 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 as or different from each other. Z + represents an organic cation.] A method for producing a resist pattern, comprising: (1) a step of applying the resist composition according to any one of [9](1)[1] to [8] on a substrate; (2) a step of drying the applied resist 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.
Advantages of the Invention
[0007] By using the resist composition 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 member selected from acrylic monomers and methacrylic monomers. The notations such as “(meth)acrylate” and “(meth)acrylic acid” also represent the same meaning. For the groups described in this specification that can take both a linear structure and a branched structure, either of them is acceptable. For -CH 2 - in a hydrocarbon group or the like being replaced with -O-, -S-, -CO-, -SO-, -NR X -(where X is an arbitrary symbol) or -SO 2 -, the same examples are applicable 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 term “combined group” means a group formed by combining two or more of the exemplified groups with appropriate changes in their valences, bonding forms, etc. The terms “derived from” or “induced from” refer to the polymerizable C═C bond contained in the molecule becoming a single bond (-C-C-) through polymerization. When stereoisomers exist, all stereoisomers are included. The term “acid-labile group” means a group having a leaving group, and upon contact with an acid (e.g., trifluoromethanesulfonic acid, etc.), the leaving group detaches to form a hydrophilic group (e.g., a hydroxy group or a carboxy group, etc.). The term “base-labile group” means a group having a leaving group, and upon contact with a base (e.g., trimethylamine, etc.), the leaving group detaches to form a hydrophilic group (e.g., a hydroxy group or a carboxy group, etc.). Each group may have any position and number of hydrogen atoms contained in the group replaced by a bonding site 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 below from the total amount of the resist composition.
[0009] [Resist Composition] The resist composition of the present invention contains a resin (hereinafter sometimes referred to as “resin (A)”) including a structural unit represented by formula (I) (hereinafter sometimes referred to as “structural unit (I)”), a structural unit having a group represented by formula (II-x) (hereinafter sometimes referred to as “structural unit (II)”), and a structural unit having an acid-labile group (hereinafter sometimes referred to as “structural unit (a1)”). The resist composition of the present invention preferably further contains a resin other than resin (A) (hereinafter sometimes referred to as resin (X)), an acid generator (hereinafter sometimes referred to as "acid generator (B)"), a quencher (hereinafter sometimes referred to as "quencher (C)") and / or a solvent (hereinafter sometimes referred to as "solvent (E)").
[0010] <Resin (A)> Resin (A) may contain structural units known in the art other than structural unit (I), structural unit (II) and structural unit (a1). Examples of structural units other than structural unit (I), structural unit (II) and structural unit (a1) include structural units having no acid-labile group (hereinafter sometimes referred to as "structural unit (s)"), other structural units (hereinafter sometimes referred to as "structural unit (t)"), and structural units known in the art.
[0011] 〈Structural unit (I)〉 Structural unit (I) is a structural unit represented by the following formula (I), and is derived from, for example, a salt represented by the following formula (I-s) that can function as an acid generator (hereinafter sometimes referred to as salt (I-s)), and the CH 2 =C-R 10 is in a state where the double bond has cleaved. Among salts (I-s), the side having a negative charge may be referred to as "anion (I-a)", and the side having a positive charge may be referred to as "cation (I-c)". TIFF2025087629000013.tif38108[In formula (I) and formula (I-s), all symbols have the same meanings as described above respectively.]
[0012] X 0 Examples of the hydrocarbon group represented by include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkanediyl groups, alkenediyl groups, and alkynediyl groups, and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, and groups combining these. -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -. In the hydrocarbon group, CO 2- The atom adjacent to it is preferably a carbon atom. In the aliphatic hydrocarbon group, for CO 2 - it is more preferable that the atom adjacent to it is a carbon atom. 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; 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, etc. The terminal of the branched alkanediyl group may be a methyl group. Examples of the alkenediyl group include ethenediyl group, propenediyl group, isopropenediyl group, butenediyl group, isobutenediyl group, tert-butenediyl group, pentenediyl group, hexenediyl group, heptenediyl group, octenediyl group, isooctenediyl group, nonenediyl group. Examples of the alkynediyl group include ethynediyl group, propynediyl group, isopropynediyl group, butynediyl group, isobutynediyl group, tert-butynediyl group, pentynediyl group, hexynediyl group, octynediyl group, nonynediyl group, etc. The number of carbon atoms of the chain hydrocarbon group is, for example, 1 to 48, preferably 1 to 18, more preferably 1 to 12, still more preferably 1 to 9, even more preferably 1 to 6, still even more preferably 1 to 4, and particularly preferably 1 to 3.
[0013] X 0 When the chain hydrocarbon group of 2- is -O-, -S-, -CO- or -SO 2 When it is replaced by -, the number of carbon atoms before replacement is taken as the number of carbon atoms of the hydrocarbon group. -CH contained in the chain hydrocarbon group 2 - is -O-, -S-, -CO- or -SO 2 Examples of the group in which - is replaced by -O-, -S-, -CO- or -SO include a hydroxy group (a group in which -CH contained in a methyl group 2 - is replaced by -O-), a carboxy group (a group in which -CH contained in an ethyl group 2 -CH 2 - is replaced by -O-CO-), a thiol group (a group in which -CH contained in a methyl group 2 - is replaced by -S-), a carbonyl group (a group in which -CH contained in a methylene group 2 - is replaced by -CO-), a sulfonyl group (a group in which -CH contained in a methylene group 2 - is -SO 2 - is replaced by -O-), an oxy group (a group in which -CH contained in a methylene group 2 - is replaced by -O-), an alkoxy group (a group in which -CH at any position contained in an alkyl group 2 - is replaced by -O-), an alkoxycarbonyl group (a group in which -CH at any position contained in an alkyl group 2 -CH 2 - is replaced by -O-CO-), an alkylcarbonyl group (a group in which -CH at any position contained in an alkyl group 2 - is replaced by -CO-), an alkylthio group (a group in which -CH at any position contained in an alkyl group 2 - is replaced by -S-), an alkylsulfonyl group (a group in which -CH at any position contained in an alkyl group 2 - is -SO 2 - is replaced by -O-), an alkylcarbonyloxy group (a group in which -CH at any position contained in an alkyl group 2 -CH 2 - is replaced by -CO-O-), an alkoxycarbonyloxy group (a group in which -CH at any position contained in an alkyl group 2 -CH 2 -CH 2- is a group replaced by -O-CO-O-, an alkanediyl-oxy group (any -CH at any position contained in the alkanediyl group) 2 - is a group replaced by -O-, an alkanediyl-oxycarbonyl group (any -CH at any position contained in the alkanediyl group) 2 -CH 2 - is a group replaced by -O-CO-, an alkanediyl-carbonyl group (any -CH at any position contained in the alkanediyl group) 2 - is a group replaced by -CO-, an alkanediyl-carbonyl-oxy group (any -CH at any position contained in the alkanediyl group) 2 -CH 2 - is a group replaced by -CO-O-, an alkanediyl-sulfonyl group (any -CH at any position contained in the alkanediyl group) 2 - is 2 - replaced by -SO, an alkanediyl-thio group (any -CH at any position contained in the alkanediyl group) 2 - is a group replaced by -S-, and groups 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 methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group and the like. The number of carbon atoms of the alkoxy group is preferably 1 to 47, more preferably 1 to 35, still more preferably 1 to 11, yet more preferably 1 to 6, still yet more preferably 1 to 4, and most 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. The number of carbon atoms of the alkoxycarbonyl group is preferably 2 to 47, more preferably 2 to 35, still more preferably 2 to 11, yet more preferably 2 to 6, still yet more preferably 2 to 4, and most preferably 2 or 3. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 72 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. The number of carbon atoms in the alkylcarbonyl group may be 2 to 48, may be 2 to 36, is preferably 2 to 12, 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 a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a 2-ethylhexylthio group, a nonylthio group, a decylthio group, and an undecylthio group. The number of carbon atoms in the alkylthio group may be 1 to 47, may be 1 to 35, is 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 a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a 2-ethylhexylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, and an undecylsulfonyl group. The number of carbon atoms in the alkylsulfonyl group may be 1 to 47, may be 1 to 35, is 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 alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 71 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. The number of carbon atoms in the alkylcarbonyloxy group may be 2 to 47, may be 2 to 35, is 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 alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 70 carbon atoms, such as a butoxycarbonyloxy group. The number of carbon atoms of the alkoxycarbonyloxy group is preferably 2 to 46, more preferably 2 to 11, still more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 to 3. Examples of the alkanediyl-oxy group include alkanediyl-oxy groups having 1 to 71 carbon atoms, such as a methylene-oxy group, an ethylene-oxy group, a propanediyl-oxy group, a butanediyl-oxy group, and a pentanediyl-oxy group. The number of carbon atoms of the alkanediyl-oxy group is preferably 1 to 47, may be 1 to 35, more preferably 1 to 11, still more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkanediyl-oxycarbonyl group include alkanediyl-oxycarbonyl groups having 2 to 71 carbon atoms, such as a methylene-oxycarbonyl group, an ethylene-oxycarbonyl group, a propanediyl-oxycarbonyl group, and a butanediyl-oxycarbonyl group. The number of carbon atoms of the alkanediyl-oxycarbonyl group is preferably 2 to 47, may be 2 to 35, more preferably 2 to 11, still more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of the alkanediyl-carbonyl group include alkanediyl-carbonyl groups having 2 to 72 carbon atoms, such as a methylene-carbonyl group, an ethylene-carbonyl group, a propanediyl-carbonyl group, a butanediyl-carbonyl group, and a pentanediyl-carbonyl group. The number of carbon atoms of the alkanediyl-carbonyl group is preferably 2 to 48, may be 2 to 36, more preferably 2 to 12, still more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of the alkanediylcarbonyl-oxy group include alkanediylcarbonyl-oxy groups having 2 to 71 carbon atoms, such as a methylenecarbonyl-oxy group, an ethylenecarbonyl-oxy group, a propanediylcarbonyl-oxy group, and a butanediylcarbonyl-oxy group. The number of carbon atoms in the alkanediylcarbonyl-oxy group is preferably 2 to 47, more preferably 2 to 35, still more preferably 2 to 11, even more preferably 2 to 6, and even more preferably 2 to 4, and most preferably 2 or 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 71 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, and a propylenesulfonyl group. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 47, more preferably 1 to 35, still more preferably 1 to 11, even more preferably 1 to 6, and even more preferably 1 to 4, and most preferably 1 to 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 71 carbon atoms, such as a methylenethio group, an ethylenethio group, and a propylenethio group. The number of carbon atoms in the alkanediylthio group is preferably 1 to 47, more preferably 1 to 35, still more preferably 1 to 11, even more preferably 1 to 6, and even more preferably 1 to 4, and most preferably 1 to 3. Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 71 carbon atoms, such as a cyclohexyloxy group. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 71 carbon atoms, such as a cyclohexylmethoxy group. The number of carbon atoms in the cycloalkoxy group and the cycloalkylalkoxy group is preferably 3 to 11, more preferably 3 to 6. Examples of the aromatic hydrocarbon group-carbonyl oxy group include aromatic hydrocarbon group-carbonyl oxy groups having 7 to 71 carbon atoms, such as a benzoyloxy group. Examples of the aromatic hydrocarbon group-carbonyl group include aromatic hydrocarbon group-carbonyl groups having 7 to 72 carbon atoms, such as a benzoyl group. Examples of the aromatic hydrocarbon group-oxy group include aromatic hydrocarbon group-oxy groups having 6 to 71 carbon atoms, such as a phenyloxy group. In addition, substitution in the alkenediyl group and the alkynediyl group may be any one that contains a carbon-carbon double bond or a carbon-carbon triple bond at an arbitrary position in the exemplified substitution in the above-described alkanediyl group.
[0014] The alicyclic hydrocarbon group may be monocyclic, polycyclic or spirocyclic. Examples of the alicyclic hydrocarbon group include the groups represented below. The bonding site can be at any position. TIFF2025087629000014.tif58166Specifically, examples of the monocyclic divalent alicyclic hydrocarbon group include monocyclic cycloalkanediyl groups such as a cyclobutane-1,3-diyl group, a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, a cyclohexene-3,6-diyl group, and a cyclooctane-1,5-diyl group. Examples of the polycyclic divalent alicyclic hydrocarbon group include polycyclic cycloalkanediyl groups such as a norbornane-1,4-diyl group, a norbornane-2,5-diyl group, a 5-norbornene-2,3-diyl group, an adamantane-1,5-diyl group, and an adamantane-2,6-diyl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably from 3 to 48, more preferably from 3 to 36, still more preferably from 3 to 24, yet more preferably from 3 to 18, even more preferably from 3 to 16, and still even more preferably from 3 to 12. -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 - to form an ether ring, a ketone ring, a lactone ring, a sultone ring or an acetal ring. Specific examples of such groups include the following groups. The bonding site can be at any position. As the alicyclic hydrocarbon group, a group represented by any of formula (y1) to formula (y11), formula (y44) to formula (y48), and formula (y59) to formula (y61) is preferable, and a group represented by any of formula (y3), formula (y4), formula (y9), and formula (y11) is more preferable. -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 - to form a group represented by any of formula (y12) to formula (y20), formula (y26), formula (y27), formula (y30), formula (y31), formula (y39) to formula (y43), and formula (y49) to formula (y71) is preferable, and a group represented by any of formula (y14), formula (y15), formula (y16), formula (y20), formula (y26), formula (y27), formula (y30), formula (y31), formula (y39), formula (y40), formula (y42), formula (y43), formula (y49) to formula (y58), and formula (y62) to formula (y71) is more preferable.
[0015] Examples of the aromatic hydrocarbon group include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, and a phenanthrylene group. The number of carbon atoms in the aromatic hydrocarbon group is preferably from 6 to 36, more preferably from 6 to 24, still more preferably from 6 to 18, yet more preferably from 6 to 14, and even more preferably from 6 to 10. Examples of hydrocarbon groups combined with two or more types include groups combining an alkanediyl group with an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group, such as -alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-aromatic hydrocarbon group-, -aromatic hydrocarbon group-alkanediyl group-, etc. X 0 In the hydrocarbon group represented by, the -CH 2 - When - is replaced by -O-, -S-, -CO- or -SO 2 -, the total number of carbon atoms of the hydrocarbon group before replacement is taken as the total number of carbon atoms of the hydrocarbon group. Also, when X 0 A substituent is bonded to the hydrocarbon group represented by, the total number of carbon atoms before substitution is taken as the total number of carbon atoms of the hydrocarbon group. In the group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, the -CH 2 - When - is replaced by -O-, -S-, -CO- or -SO 2 - Examples of the group after replacement also include the following groups, etc. The bonding site can be at any position. TIFF2025087629000016.tif26164
[0016] X 0 The hydrocarbon group represented by may have one or more substituents. Examples of the substituent include a hydroxy group, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a group combining these, etc. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a nonyl group, etc. Examples of the alkoxy group having 1 to 12 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group and the like. Examples of the alkoxycarbonyl group having 2 to 13 carbon atoms include a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group and the like. Examples of the alkylcarbonyl group having 2 to 13 carbon atoms include an acetyl group, a propionyl group, a butyryl group and the like. Examples of the alkylcarbonyloxy group having 2 to 13 carbon atoms include an acetyloxy group, a propionyloxy group, a butyryloxy group and the like. Examples of the alicyclic hydrocarbon group having 3 to 12 carbon atoms include the groups shown below. ** represents the bonding site with X 0 and. TIFF2025087629000017.tif17162 Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include aryl groups such as a phenyl group and a naphthyl group. Examples of the combined groups include a group formed by combining a hydroxy group and an alkyl group having 1 to 12 carbon atoms, a group formed by combining an alkyl group having 1 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms, a group formed by combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms, a group formed by combining an alkyl group having 1 to 12 carbon atoms and an alicyclic hydrocarbon group having 3 to 12 carbon atoms, a group formed by combining a halogen atom and an alkyl group having 1 to 12 carbon atoms and the like. Examples of the group formed by combining a hydroxy group and an alkyl group having 1 to 12 carbon atoms include hydroxyalkyl groups having 1 to 12 carbon atoms such as a hydroxymethyl group and a hydroxyethyl group. Examples of the group formed by combining an alkyl group having 1 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include aralkyl groups having 7 to 22 carbon atoms such as a benzyl group, and alkylaryl groups having 7 to 22 carbon atoms such as a tolyl group and a xylyl group. Examples of the group formed by combining an alicyclic hydrocarbon group having 3 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atoms include a cyclohexylphenyl group and the like. Examples of the group formed by combining an alkyl group having 1 to 12 carbon atoms and an alicyclic hydrocarbon group having 3 to 12 carbon atoms include cycloalkylalkyl groups having 4 to 24 carbon atoms such as cyclohexylmethyl group, and alkylcycloalkyl groups having 4 to 24 carbon atoms such as methylcyclohexyl group. Examples of the group formed by combining a halogen atom and an alkyl group having 1 to 12 carbon atoms include perfluoroalkyl groups having 1 to 12 carbon atoms such as trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, and nonafluorobutyl group.
[0017] X 0 The hydrocarbon group represented by is preferably an aliphatic hydrocarbon group having 1 to 72 carbon atoms which may have a substituent (wherein -CH 2 - in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), or an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent, more preferably, a chain hydrocarbon group having 1 to 18 carbon atoms which may have a substituent (wherein -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 36 carbon atoms which may have a substituent (wherein -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), a group formed by combining an alicyclic hydrocarbon group having 3 to 36 carbon atoms which may have a substituent and a chain hydrocarbon group having 1 to 18 carbon atoms which may have a substituent (wherein -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -, and -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent or a group formed by combining an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent and a chain hydrocarbon group having 1 to 18 carbon atoms which may have a substituent (wherein -CH 2- may be replaced by -O- or -CO-. It includes More preferably, *- chain hydrocarbon group -, *- alicyclic hydrocarbon group -, *- group combining an alicyclic hydrocarbon group and a chain hydrocarbon group -, *- alicyclic hydrocarbon group - chain hydrocarbon group -, *- chain hydrocarbon group - alicyclic hydrocarbon group -, *- group combining an alicyclic hydrocarbon group and a chain hydrocarbon group - chain hydrocarbon group -, *- chain hydrocarbon group - alicyclic hydrocarbon group and a group combining a chain hydrocarbon group -, *- aromatic hydrocarbon group -, *- chain hydrocarbon group - aromatic hydrocarbon group -, *- aromatic hydrocarbon group - chain hydrocarbon group -, *- alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group -, *- chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group -, *- group combining an alicyclic hydrocarbon group and a chain hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group -, *- chain hydrocarbon group - alicyclic hydrocarbon group and a group combining a chain hydrocarbon group - chain hydrocarbon group -, *- chain hydrocarbon group - alicyclic hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group -, or *- chain hydrocarbon group - alicyclic hydrocarbon group and a group combining a chain hydrocarbon group - chain hydrocarbon group - alicyclic hydrocarbon group - (the -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO- or -SO 2 - may be replaced by -O- or -CO-, and the -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group, the aromatic hydrocarbon group and the chain hydrocarbon group may have substituents. * is -COO - represents the bonding site with the carbon atom of).) and is Even more preferably, *- alicyclic hydrocarbon group - (the -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO- or -SO 2 - may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of).), *- alicyclic hydrocarbon group - chain hydrocarbon group - (the -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO- or -SO2 - may be replaced, and -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group and the chain hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.)., *-chain hydrocarbon group-alicyclic hydrocarbon group-( -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO-, or -SO 2 - and the chain hydrocarbon group and the alicyclic hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.)., *-aromatic hydrocarbon group-(the aromatic hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.). or *-chain hydrocarbon group-aromatic hydrocarbon group-( -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the chain hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.)., and even more preferably, *-monocyclic alicyclic hydrocarbon group-( -CH contained in the monocyclic alicyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO-, or -SO 2 - and the monocyclic alicyclic hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.)., *-polycyclic alicyclic hydrocarbon group-( -CH contained in the polycyclic alicyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO-, or -SO 2- may be replaced, and the polycyclic alicyclic hydrocarbon group may have a halogen atom, a C1-C4 perfluoroalkyl group or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.)., *- polycyclic alicyclic hydrocarbon group - chain hydrocarbon group - (-CH contained in the polycyclic alicyclic hydrocarbon group 2 - is -O-, -S-, -CO- or -SO 2 - may be replaced, and -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the polycyclic alicyclic hydrocarbon group and the chain hydrocarbon group may have a halogen atom, a C1-C4 perfluoroalkyl group or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.)., *- chain hydrocarbon group - polycyclic alicyclic hydrocarbon group - (-CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and -CH contained in the polycyclic alicyclic hydrocarbon group 2 - is -O-, -S-, -CO- or -SO 2 - may be replaced, and the chain hydrocarbon group and the polycyclic alicyclic hydrocarbon group may have a halogen atom, a C1-C4 perfluoroalkyl group or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.)., *- aromatic hydrocarbon group - (the aromatic hydrocarbon group may have a halogen atom, a C1-C4 perfluoroalkyl group or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.) or *- chain hydrocarbon group - aromatic hydrocarbon group - (-CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the chain hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom, a C1-C4 perfluoroalkyl group or a hydroxy group. * is -COO - represents the bonding site with the carbon atom of.). On the basis described above, the number of carbon atoms of the alicyclic hydrocarbon group is preferably from 3 to 36, more preferably from 3 to 24, still more preferably from 3 to 18, even more preferably from 3 to 16, and even more preferably from 3 to 12. The number of carbon atoms of the chain hydrocarbon group is preferably from 1 to 18, more preferably from 1 to 12, still more preferably from 1 to 9, even more preferably from 1 to 6, and even more preferably from 1 to 4. The number of carbon atoms of the aromatic hydrocarbon group is preferably from 6 to 36, more preferably from 6 to 24, still more preferably from 6 to 18, even more preferably from 6 to 14, and even more preferably from 6 to 10. In the above group, the alicyclic hydrocarbon group or the aromatic hydrocarbon group is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms (—CH 2 — in the group may be replaced by —O—, —S—, —CO— or —SO 2 —). More preferably, it is a group represented by any one of formula (w1-1) to formula (w1-28), still more preferably a group represented by any one of formula (w1-1) to formula (w1-6) and formula (w1-12) to formula (w1-26), and even more preferably a group represented by any one of formula (w1-1) to formula (w1-3), formula (w1-6), formula (w1-15) to formula (w1-17), formula (w1-22) and formula (w1-25). TIFF2025087629000018.tif55150 [In formula (w1-1) to formula (w1-28), —CH contained in the group 2 — may be replaced by —O—, —S—, —CO— or —SO 2 —. The bonding site is at an arbitrary position.] More specifically, the above monocyclic alicyclic hydrocarbon group is a cycloalkanediyl group having 5 or 6 carbon atoms (—CH contained in the cycloalkanediyl group 2- may be replaced by -O- or -CO-. It is preferably so, and the above polycyclic alicyclic hydrocarbon group is preferably an adamantandiyl group, a norbornandiyl group, an adamantanlactonediyl group, a norbornanlactonediyl group, or a polycyclic alicyclic hydrocarbon group in which a C5 or C6 cycloalkanediyl group and a C5 - C8 cycloalkanediyl group are spiro - bonded, a polycyclic alicyclic hydrocarbon group in which a norbornandiyl group and a C5 - C8 cycloalkanediyl group are spiro - bonded or a polycyclic alicyclic hydrocarbon group in which an adamantandiyl group and a C5 - C8 cycloalkanediyl group are spiro - bonded. The above aromatic hydrocarbon group is preferably a phenylene group. Here, -CH contained in the adamantandiyl group and the norbornandiyl group 2 -CH 2 - may be replaced by -O - CO-, and the cycloalkanediyl group may be an acetal ring.
[0018] In the above group, the chain hydrocarbon group is preferably a chain hydrocarbon group having 1 - 12 carbon atoms (where -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-). More preferably, it is a chain hydrocarbon group having 1 - 8 carbon atoms (where -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-). Even more preferably, it is an alkanediyl group having 1 - 6 carbon atoms (where -CH contained in the alkanediyl group 2 - may be replaced by -O- or -CO-). It is also preferably having a fluorine atom. In the above group, the substituent is preferably a halogen atom, a hydroxy group, an alkyl group having 1 - 4 carbon atoms, an alicyclic hydrocarbon group having 3 - 10 carbon atoms or a group combining these. More preferably, it is a fluorine atom, a hydroxy group or a perfluoroalkyl group having 1 - 4 carbon atoms. More specifically, X 0 is preferably a single bond or an aliphatic hydrocarbon group having 1 - 72 carbon atoms which may have a substituent (where -CH contained in the aliphatic hydrocarbon group 2- may be replaced by -O-, -S-, -CO- or -SO 2 ), or it may contain an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent, more preferably, it is a single bond, or a chain hydrocarbon group having 1 to 18 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (in the -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), a halogen atom, an alicyclic hydrocarbon group having 3 to 36 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (in the -CH 2 - may be replaced by -O-, -S-, -CO- or -SO 2 -), a group combining an alicyclic hydrocarbon group having 3 to 36 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms (in the -CH 2 - may be replaced by -O-, -S-, -CO- or -SO 2 - in the alicyclic hydrocarbon group and the chain hydrocarbon group may be replaced by -O- or -CO-, and the -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group and the chain hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group), a halogen atom, an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, or a group combining an aromatic hydrocarbon group having 6 to 36 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms (in the -CH 2 - in the aromatic hydrocarbon group and the chain hydrocarbon group may be replaced by -O- or -CO-, and the aromatic hydrocarbon group and the chain hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group). Even more preferably, it is a single bond, or a chain hydrocarbon group having 1 to 12 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (in the -CH 2- may be replaced by -O- or -CO-.), an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (-CH contained in the alicyclic hydrocarbon group 2 - may be -O-, -S-, -CO- or -SO 2 - may be replaced by -).), a group combining an alicyclic hydrocarbon group having 3 to 18 carbon atoms and a chain hydrocarbon group having 1 to 8 carbon atoms (-CH contained in the alicyclic hydrocarbon group 2 - may be -O-, -S-, -CO- or -SO 2 - may be replaced by - and -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group and the chain hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group.).), an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, or a group combining an aromatic hydrocarbon group having 6 to 18 carbon atoms and a chain hydrocarbon group having 1 to 8 carbon atoms (-CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the aromatic hydrocarbon group and the chain hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group.).) is included, More preferably, it is a single bond, an alkanediyl group having 1 to 6 carbon atoms, a cycloalkanediyl group having 5 or 6 carbon atoms, an adamantanediyl group, a norbornanediyl group, an adamantanlactonediyl group, a norbornanlactonediyl group, a phenylene group, a group combining an alkanediyl group having 1 to 6 carbon atoms with a cycloalkanediyl group having 5 to 6 carbon atoms, an adamantanediyl group, a norbornanediyl group or a phenylene group, a polycyclic alicyclic hydrocarbon group in which a cycloalkanediyl group having 5 to 6 carbon atoms and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded, a polycyclic alicyclic hydrocarbon group in which a norbornanediyl group and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded or a polycyclic alicyclic hydrocarbon group in which an adamantanediyl group and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded (the -CH 2 - in the alkanediyl group, the cycloalkanediyl group, the adamantanediyl group, the norbornanediyl group, the adamantanlactonediyl group, the norbornanlactonediyl group and the phenylene group may be replaced by -O- or -CO-, and the alkanediyl group, the cycloalkanediyl group, the adamantanediyl group, the norbornanediyl group, the adamantanlactonediyl group, the norbornanlactonediyl group and the phenylene group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group.). Even more preferably, it is a cyclohexanediyl group, an adamantanediyl group, a hydroxyadamantanediyl group, a norbornanlactonediyl group, a group combining an alkanediyl group having 1 to 6 carbon atoms with an adamantanediyl group (the -CH 2 - in the alkanediyl group may be replaced by -O- or -CO-), a phenylene group, or a hydroxyphenylene group. Also, X 0contains an alicyclic hydrocarbon group, and the alicyclic hydrocarbon group is a cycloalkanediyl group having 5 or 6 carbon atoms, an adamantanediyl group, a norbornanediyl group, an adamantanlactonediyl group, a norbornanlactonediyl group, a polycyclic alicyclic hydrocarbon group in which a cycloalkanediyl group having 5 or 6 carbon atoms and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded, a polycyclic alicyclic hydrocarbon group in which a norbornanediyl group and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded, or a polycyclic alicyclic hydrocarbon group in which an adamantanediyl group and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded (the adamantanediyl group, the norbornanediyl group, and the cycloalkanediyl group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group, and -CH 2 - in the adamantanediyl group, the norbornanediyl group, and the cycloalkanediyl group may be replaced by -O- or -CO-). It is also preferable that it contains such a group. Here, -CH 2 -CH 2 - in the adamantanediyl group and the norbornanediyl group may be replaced by -O-CO-, and the cycloalkanediyl group may be an acetal ring.
[0019] L 10 Examples of the hydrocarbon group having 1 to 36 carbon atoms of L include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkanediyl groups, alkenediyl groups, and alkynediyl groups and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, etc., and a hydrocarbon group obtained by combining two or more of these groups may also be used. 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; Examples of the branched alkanediyl group include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, a 2-methylbutane-1,4-diyl group, etc. The terminal of the branched alkanediyl group may be a methyl group. Examples of the alkenediyl group include an ethenediyl group, a propenediyl group, an isopropenediyl group, a butenediyl group, an isobutenediyl group, a tert-butenediyl group, a pentenediyl group, a hexenediyl group, a heptenediyl group, an octenediyl group, an isooctenediyl group, a nonenediyl group. Examples of the alkynediyl group include an ethynediyl group, a propynediyl group, an isopropynediyl group, a butynediyl group, an isobutynediyl group, a tert-butynediyl group, a pentynediyl group, a hexynediyl group, an octynediyl group, a nonynediyl group, etc. The number of carbon atoms of the chain hydrocarbon 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 divalent alicyclic hydrocarbon group may be monocyclic, polycyclic or spirocyclic. Examples of the divalent alicyclic hydrocarbon group include the groups represented below. The bonding site can be at any position. TIFF2025087629000019.tif47168Specifically, examples of the monocyclic divalent alicyclic hydrocarbon group include monocyclic cycloalkanediyl groups such as a cyclobutane-1,3-diyl group, a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, a cyclohexene-3,6-diyl group, a cyclooctane-1,5-diyl group, etc. Examples of the polycyclic divalent alicyclic hydrocarbon group include polycyclic cycloalkanediyl groups such as a norbornane-1,4-diyl group, a norbornane-2,5-diyl group, a 5-norbornene-2,3-diyl group, an adamantane-1,5-diyl group, an adamantane-2,6-diyl group, etc. 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. Examples of the divalent aromatic hydrocarbon group include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and still more preferably 6 to 10. Examples of the hydrocarbon group formed by combining two or more types include a group formed by combining an alkanediyl group with an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group, such as -alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-aromatic hydrocarbon group-, -aromatic hydrocarbon group-alkanediyl group-, etc. Also, in the case of a group formed by combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group with an alkanediyl group, the terminal of the alkanediyl group may be an alkyl group such as a methyl group.
[0020] L 10 In the hydrocarbon group having 1 to 36 carbon atoms of 2 -CH 2 - may be replaced by -O-, -S-, -CO- or -SO L 10 When the hydrocarbon group having 1 to 36 carbon atoms of 2 has a substituent or -CH 2 - in the hydrocarbon group is replaced by -O-, -S-, -CO- or -SO - in the hydrocarbon group, the number of carbon atoms before replacement is taken as the number of carbon atoms of the hydrocarbon group. 2 Examples of the group in which -CH 2 - in the hydrocarbon group is replaced by -O-, -S-, -SO 2 - or -CO- include a hydroxy group (a group in which -CH 2 -CH 2 - in a methyl group is replaced by -O-), a carboxy group (a group in which -CH 2- is a group replaced by -S-), a carbonyl group (-CH contained in a methylene group 2 - is a group replaced by -CO-), a sulfonyl group (-CH contained in a methylene group 2 - is replaced by -SO 2 - is a group replaced by -SO-), an oxy group (-CH contained in a methylene group 2 - is a group replaced by -O-), a thio group (-CH contained in a methylene group 2 - is a group replaced by -S-), an alkoxy group (-CH at any position contained in an alkyl group 2 - is a group replaced by -O-), an alkoxycarbonyl group (-CH at any position contained in an alkyl group 2 -CH 2 - is a group replaced by -O-CO-), an alkylcarbonyl group (-CH at any position contained in an alkyl group 2 - is a group replaced by -CO-), an alkylcarbonyloxy group (-CH at any position contained in an alkyl group 2 -CH 2 - is a group replaced by -CO-O-), an alkanedioxy group (-CH at any position contained in an alkanedioyl group 2 - is a group replaced by -O-), an alkanedioxycarbonyl group (-CH at any position contained in an alkanedioyl group 2 -CH 2 - is a group replaced by -O-CO-), an alkanedioylcarbonyl group (-CH at any position contained in an alkanedioyl group 2 - is a group replaced by -CO-), an alkanedioylcarbonyloxy group (-CH at any position contained in an alkanedioyl group 2 -CH 2 - is a group replaced by -CO-O-), an alkylthio group (-CH at any position contained in an alkyl group 2 - is a group replaced by -S-), an alkylsulfonyl group (-CH at any position contained in an alkyl group 2 - is replaced by -SO 2 - is a group replaced by -SO-), an alkanedioylsulfonyl group (-CH at any position contained in an alkanedioyl group 2 - is replaced by -SO2 -replaced group), an alkanediylthio group (any position -CH in the alkanediyl group 2 - replaced by -S-), a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, an aromatic hydrocarbon group-carbonyloxy 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. Examples of the alkoxy group include alkoxy groups having 1 to 35 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 17, 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 35 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, and the like. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 36 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 35 carbon atoms, such as an acetyloxy group, a propionyloxy group, a butyryloxy group, and the like. The number of carbon atoms of the alkoxycarbonyl group, the alkylcarbonyl group, and the alkylcarbonyloxy group may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3. Examples of the alkanediyl-oxy group include alkanediyl-oxy groups having 1 to 35 carbon atoms, such as a methylene-oxy group, an ethylene-oxy group, a propanediyl-oxy group, a butanediyl-oxy group, and a pentanediyl-oxy group. The number of carbon atoms in the alkanediyl-oxy group may be 1 to 17, 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 35 carbon atoms, such as a methylene-oxycarbonyl group, an ethylene-oxycarbonyl group, a propanediyl-oxycarbonyl group, and a butanediyl-oxycarbonyl group. Examples of the alkanediyl-carbonyl group include alkanediyl-carbonyl groups having 2 to 36 carbon atoms, such as a methylene-carbonyl group, an ethylene-carbonyl group, a propanediyl-carbonyl group, a butanediyl-carbonyl group, and a pentanediyl-carbonyl group. Examples of the alkanediyl-carbonyloxy group include alkanediyl-carbonyloxy groups having 2 to 35 carbon atoms, such as a methylene-carbonyloxy group, an ethylene-carbonyloxy group, a propanediyl-carbonyloxy group, and a butanediyl-carbonyloxy group. The number of carbon atoms in the alkanediyl-oxycarbonyl group, the alkanediyl-carbonyl group, and the alkanediyl-carbonyloxy group may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3. Examples of the alkylthio group include alkylthio groups having 1 to 35 carbon atoms, such as a methylthio group, an ethylthio group, and a propylthio group. The number of carbon atoms in the alkylthio group may be 1 to 17, 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 35 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group and the like. The number of carbon atoms of the alkylsulfonyl group may be 1 to 17, 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 35 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 17, 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 alkanediylthio group include alkanediylthio groups having 1 to 35 carbon atoms, such as methylenethio group, ethylenethio group, propylenethio group and the like. The number of carbon atoms of the alkanediylthio group may be 1 to 17, 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 35 carbon atoms, such as a cyclohexyloxy group. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 35 carbon atoms, such as a cyclohexylmethoxy group. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 34 carbon atoms, such as a butoxycarbonyloxy group. The number of carbon atoms of the cycloalkoxy group and the cycloalkylalkoxy group is preferably 3 to 11, more preferably 3 to 6. The number of carbon atoms of the alkoxycarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3. Examples of the aromatic hydrocarbon group-carbonyl oxy group include aromatic hydrocarbon group-carbonyl oxy groups having 7 to 35 carbon atoms, such as a benzoyloxy group. Examples of the aromatic hydrocarbon group-carbonyl group include aromatic hydrocarbon group-carbonyl groups having 7 to 36 carbon atoms, such as a benzoyl group. Examples of the aromatic hydrocarbon group-oxy group include aromatic hydrocarbon group-oxy groups having 6 to 35 carbon atoms, such as a phenyloxy group. In addition, -CH 2 - contained in the alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO 2 - Examples of the resulting group include the groups represented below. -O- or -CO- in the groups represented below may be replaced with -S- or -SO 2 -. The bonding site can be at any position. TIFF2025087629000020.tif45168 -CH 2 - contained in the group combining the alicyclic hydrocarbon group and the aromatic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO 2 - Examples of the resulting group include the same groups as those exemplified in this specification within the range where the upper limit of the number of carbon atoms is allowed.
[0021] L 10 Examples of the substituent that the hydrocarbon group of may have include a halogen atom, a cyano group, a nitro group, and the like. L 10 When L contains a group formed by combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group with a chain hydrocarbon group such as an alkanediyl group (the ends of the alkanediyl group may be an alkyl group such as a methyl group), the chain hydrocarbon group such as the alkanediyl group bonded to the alicyclic hydrocarbon group or the aromatic hydrocarbon group can be substantially regarded as a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. L 10 In the hydrocarbon group of 2 L, when -CH 10 - is replaced by a group such as -O- or -CO-, L Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L 10 The hydrocarbon group having 1 to 36 carbon atoms of L may have one substituent or a plurality of substituents.
[0022] L 10 is a single bond, a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (provided that -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (provided that -CH 2 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), 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 24 carbon atoms which may have a substituent (provided that -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH 2 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-). Preferably, it is a single bond, a chain hydrocarbon group having 1 to 6 carbon atoms (provided that -CH 2- may be replaced by -O- or -CO. ), a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and -CH contained in the cyclic hydrocarbon group 2 - may be -O-, -S-, -SO 2 - or -CO. ) or a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms and a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO, and -CH contained in the cyclic hydrocarbon group 2 - may be -O-, -S-, -SO 2 - or -CO. ) is more preferably, a single bond, a chain hydrocarbon group having 1 to 4 carbon atoms (provided that -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO. ), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH contained in the alicyclic hydrocarbon group 2 - may be -O-, -S-, -SO 2 - or -CO. ), an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, a group formed by combining a chain hydrocarbon group having 1 to 4 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO, and -CH contained in the alicyclic hydrocarbon group 2 - may be -O-, -S-, -SO 2 - or -CO. ) or a group formed by combining a chain hydrocarbon group having 1 to 4 carbon atoms and an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent (provided that -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO. ) is even more preferably, a single bond, a chain hydrocarbon group having 1 to 4 carbon atoms (provided that -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO. ), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH contained in the alicyclic hydrocarbon group 2- may be replaced by -O- or -CO). A phenylene group which may have a substituent, a group formed by combining an acyclic hydrocarbon group having 1 to 4 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (however, -CH contained in the acyclic hydrocarbon group) 2 - may be replaced by -O- or -CO, and -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O- or -CO). Or a group formed by combining an acyclic hydrocarbon group having 1 to 4 carbon atoms and a phenylene group which may have a substituent (however, -CH contained in the acyclic hydrocarbon group) 2 - may be replaced by -O- or -CO). It is more preferably this, and a single bond or an acyclic hydrocarbon group having 1 to 4 carbon atoms (however, -CH contained in the acyclic hydrocarbon group) 2 - may be replaced by -O- or -CO). It is even more preferably this.
[0023] R 10 Examples of the halogen atom of R include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like. R 10 Examples of the alkyl group of R include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group. R 10 Examples of the alkyl group having 1 to 6 carbon atoms having a halogen atom of R include an alkyl fluoride group having 1 to 6 carbon atoms, an alkyl chloride group having 1 to 6 carbon atoms, an alkyl bromide group having 1 to 6 carbon atoms, an alkyl iodide group having 1 to 6 carbon atoms and the like. Specifically, 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 perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a perchloromethyl group, a perbromomethyl group and a periodomethyl group. The number of carbon atoms in the alkyl group, alkyl fluoride group, alkyl chloride group, alkyl bromide group, and alkyl iodide group is preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 or 2. R 10 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 or a methyl group, and even more preferably a methyl group.
[0024] X 10 When it is a group represented by *-Ax-Ph-Ay-*, it is preferably a linking group represented by the following formula (X10). TIFF2025087629000021.tif3449[In the formula (X10), Ax represents the type of bond that binds to the carbon atom to which R 10 is bonded, and represents one or more types of bonds selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond. Ay represents the type of bond that binds to L 10 and represents one or more types of bonds selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond. Rx represents a halogen atom, a hydroxy group, an alkyl fluoride 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. When mx is an integer of 2 or more, the plurality of Rx may be the same as or different from each other.] When either Ax or Ay is a single bond, the other is preferably one or more selected from the group consisting of an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond. When either Ax or Ay is an amide bond, it is preferably a bond represented by -CO-NR 3 -. R 3 The alkyl group of 10 is the same as those exemplified by 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. The bonding position of Ay in the phenylene group is preferably the m-position or p-position relative to the bonding position of Ax, more preferably the p-position. X 10 Examples of [X 10 -1) to formula (X 10 -10). * represents the bonding site with the carbon atom to which R 10 is bonded. ** represents the bonding site with the L 10 side. TIFF2025087629000022.tif45170 [In formula (X 10 -1) to formula (X 10 -10), *, ** are bonding sites, and * represents the bonding site with the carbon atom to which R 10 is bonded. Rx represents a halogen atom, a hydroxy group, a C1-C6 fluoroalkyl group, a C1-C18 alkyl group or a C1-C6 alkoxy group. mx represents any integer from 0 to 4. X 20 is -O- or -NR 3 -. R 3 represents a hydrogen atom or a C1-C6 alkyl group. Specific examples of the group represented by formula (X 10 -1) to formula (X 10 -10) include the following groups. TIFF2025087629000023.tif87163 Among them, 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 (X10 -6’) and a group represented by formula (X 10 -10’) is more preferably a single bond, a group represented by formula (X 10 -1’), a group represented by formula (X 10 -5’) or a group represented by formula (X 10 -6’).
[0025] Examples of the anion (I-a) include the following anions. TIFF2025087629000024.tif249164
[0026] TIFF2025087629000025.tif78159
[0027] In the anions represented by formula (I-a-1) to formula (I-a-40), an anion in which the methyl group corresponding to R in formula (I) is replaced by a hydrogen atom can also be mentioned as a specific example of the anion (I-a). Among them, anions represented by formula (I-a-1) to formula (I-a-12) and formula (I-a-32) to formula (I-a-36) are preferred. 10
[0028] Z1 + Examples of the organic cation of TIFF2025087629000026.tif82160[In formula (b2-1) to formula (b2-5), R b4 ~R b6Each independently represents an aliphatic hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms, and the hydrogen atoms contained in the aliphatic hydrocarbon group may be substituted with a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. The hydrogen atoms contained in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a glycidyloxy group. The hydrogen atoms contained in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b4 and R b5 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and the —CH 2 — in the ring may be replaced by —O—, —S—, or —CO—. R b7 and R b8 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. m2 and n2 each independently represent any integer from 0 to 5. When m2 is 2 or more, the plurality of R b7 may be the same or different, and when n2 is 2 or more, the plurality of R b8 may be the same or different. R b9 and R b10 each independently represents an aliphatic hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded, and the —CH 2 — in the ring may be replaced by —O—, —S—, or —CO—. R b11represents a hydrogen atom, a chain hydrocarbon group having 1 to 36 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. R b12 represents a chain hydrocarbon group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 12 carbon atoms or an alkylcarbonyloxy group having 1 to 12 carbon atoms. R b11 and R b12 and may be bonded to each other to form a ring including -CH-CO- to which they are bonded, and -CH 2 - in the ring may be replaced with -O-, -S- or -CO-. R b13 ~R b18 and R b21 ~R b26 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b13 and R b14 and R b21 and R b22 and may be bonded to each other to form a ring containing a sulfur atom together with the benzene ring to which they are bonded, and -CH 2 - in the ring may be replaced with -O-, -S- or -CO-. R b27 ~R b29 each independently represents a hydrogen atom or a group containing an acid-labile group. L b31 and L b41 ~L b43 each independently represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent an integer of 0 to 5. q2 and r2 each independently represent an integer of 0 to 4. u2 represents 0 or 1. When o2 is 2 or more, a plurality of Rs b13 are the same or different, and when p2 is 2 or more, a plurality of Rs b14 are the same or different, and when q2 is 2 or more, a plurality of Rs b15 are the same or different, and when r2 is 2 or more, a plurality of Rs b16 are the same or different, and when s2 is 2 or more, a plurality of Rs b17 are the same or different, and when t2 is 2 or more, a plurality of Rs b18 are the same or different. u3 represents any integer from 1 to 3 and satisfies 1 ≦ u3 + q23 ≦ 5. u4 and u5 each independently represent any integer from 0 to 3 and satisfy 0 ≦ u4 + o21 ≦ 5 and 0 ≦ u5 + p22 ≦ 5. When u3, u4, and u5 are each 2 or more, the groups within the plurality of parentheses are each the same or different. o21, p22, q23, r24, t25, and s26 each independently represent any integer from 0 to 4. When o21, p22, q23, r24, t25, and s26 are each 2 or more, a plurality of Rs b21 ~R b26 are each the same or different. When u2 is 0, any one of o2, p2, q2, and r2 is 1 or more, and at least one of Rs b13 ~R b16 is preferably a halogen atom. When u2 is 1, any one of o2, p2, s2, t2, q2, and r2 is 1 or more, and at least one of Rs b13 ~R b18 is preferably a halogen atom. Furthermore, when u2 is 0, r2 is preferably 1 or more, more preferably 1. Also, when u2 is 0 and r2 is 1 or more, R b16 is preferably a halogen atom.
[0029] 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, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl groups. In particular, R b9 ~R b12 The chain hydrocarbon group is preferably a C1-C12 group. The alicyclic hydrocarbon group may be monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl groups. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl, adamantyl, norbornyl, and the following groups. TIFF2025087629000027.tif11157In particular, R b9 ~R b12 The alicyclic hydrocarbon group is preferably a C3-C18 group, more preferably a C4-C12 group.
[0030] Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include methylcyclohexyl, dimethylcyclohexyl, 2-methyladamantan-2-yl, 2-ethyladamantan-2-yl, 2-isopropyladamantan-2-yl, methylnorbornyl, and isobornyl groups. 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.
[0031] The alkyl fluoride group represents an alkyl group having 1 to 12 carbon atoms and having a fluorine atom, and examples thereof include fluoromethyl, difluoromethyl, trifluoromethyl, and perfluorobutyl groups. 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.
[0032] Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, biphenyl group, naphthyl group, and phenanthryl group. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples of the aromatic hydrocarbon group having a chain hydrocarbon group include tolyl group, xylyl group, cumenyl group, mesityl group, p-ethylphenyl group, p-tert-butylphenyl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc., and examples of the aromatic hydrocarbon group having an alicyclic hydrocarbon group include p-cyclohexylphenyl group, p-adamantylphenyl group, etc. When the aromatic hydrocarbon group has a chain hydrocarbon group or an alicyclic hydrocarbon group, a chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms are preferred. Examples of the aromatic hydrocarbon group in which a hydrogen atom is substituted with an alkoxy group include p-methoxyphenyl group, etc. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as benzyl group, phenethyl group, phenylpropyl group, trityl group, naphthylmethyl group, naphthylethyl group, etc.
[0033] Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group, and dodecyloxy group, etc. Examples of the alkylcarbonyl group include acetyl group, propionyl group, and butyryl group, etc. Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom, and iodine atom, etc. Examples of the alkylcarbonyloxy group include methylcarbonyloxy group, ethylcarbonyloxy group, propylcarbonyloxy group, isopropylcarbonyloxy group, butylcarbonyloxy group, sec-butylcarbonyloxy group, tert-butylcarbonyloxy group, pentylcarbonyloxy group, hexylcarbonyloxy group, octylcarbonyloxy group, and 2-ethylhexylcarbonyloxy group, etc.
[0034] Rb4 and R b5 The ring formed by the combination of and the sulfur atom to which they are attached may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of 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, and examples thereof include the following rings. * represents a bonding site. TIFF2025087629000028.tif24142
[0035] R b9 and R b10 The ring formed by combining and may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of this ring include 3-membered to 12-membered rings, preferably 3-membered to 7-membered rings. Examples thereof include thiolan-1-ium ring (tetrahydrothiophenium ring), thian-1-ium ring, 1,4-oxathian-4-ium ring and the like. R b11 and R b12 The ring formed by combining and may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of this ring include 3-membered to 12-membered rings, preferably 3-membered to 7-membered rings. Examples thereof include oxocycloheptane ring, oxocyclohexane ring, oxonorbornane ring, oxoadamantane ring and the like. R b27 ~R b29 Examples of the group containing an acid-labile group of ~ include -R c30 , -CO-O-R c30 or -L c10 -CO-O-R c30 wherein the group represented by L c10 represents an alkanediyl group having 1 to 6 carbon atoms, and R c30 represents an acid-labile group.) and the like. R b27 ~R b29 Examples of the acid-labile group of ~ include group (1) or group (2).
[0036] Among cations (b2-1) to (b2-5), preferably, cation (b2-1), cation (b2-4), or cation (b2-5) is used. Examples of cation (b2-1) include the following cations. TIFF2025087629000029.tif158165 Examples of cation (b2-2) include the following cations. TIFF2025087629000030.tif14136 Examples of cation (b2-3) include the following cations. TIFF2025087629000031.tif21130 Examples of cation (b2-4) include the following cations. TIFF2025087629000032.tif130167 Examples of cation (b2-5) include the following cations. TIFF2025087629000033.tif114159
[0037] Salt (I-s) is a combination of the above-mentioned anion (I-a) and the above-mentioned organic cation Z1 + (cation (I-c)), and these can be arbitrarily combined. Examples of salt (I-s) preferably include a combination of an anion represented by any of formula (I-a-1) to formula (I-a-12), formula (I-a-32) to formula (I-a-36), and cation (b2-1), cation (b2-2), cation (b2-3), cation (b2-4), or cation (b2-5).
[0038] Examples of salt (I-s) 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, and "~" indicates that each of salt (I-s) and anion (I) or cation (I) corresponds. For example, salt (I-s-1) means a salt composed of an anion represented by formula (I-a-1) and a cation represented by formula (b2-c-1), and represents the salts shown below. TIFF2025087629000034.tif31121
Table 1
[0039] 〈Structural unit (II)〉 The structural unit (II) is a structural unit having a group represented by the formula (II-x), and preferably a structural unit having a group represented by the formula (II-x) in the side chain. TIFF2025087629000037.tif2958[In the formula (II-x), all the symbols have the same meanings as described above.]
[0040] Ring W 1 represents a ring structure containing a nitrogen atom as an atom constituting the ring, and one of the carbon atoms constituting the ring forms a carbonyl group together with an oxo group (=O). Ring W 1 The heterocyclic ring of 2 for example, the -CH c - constituting the ring may be further replaced by -O-, -S-, -CO- or -NR crepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ring W 1 The heterocyclic ring of 1 may be an aromatic heterocyclic ring or an alicyclic heterocyclic ring having no aromaticity. Further, it may be either monocyclic or polycyclic.
[0041] The following formula Examples of the group represented by TIFF2025087629000038.tif1923 specifically include the following. * represents a bond to the carbon atom of the carbonyl group. TIFF2025087629000039.tif130162
[0042] Ring W 1 The hydrogen atoms contained in the heterocyclic ring having 2 to 36 carbon atoms represented by 1 may be substituted with a halogen atom or a hydrocarbon group having 1 to 24 carbon atoms (the -CH 2 - in the hydrocarbon group may be replaced by an -O-, -S-, -CO- or -NR c - group). Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like. Examples of the hydrocarbon group include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a group combining these. The -CH 2 - in the hydrocarbon group may be replaced by an -O-, -S-, -CO-, -NR c - group (R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), and is preferably replaced by -O- or -CO-. The aliphatic hydrocarbon group represents a chain hydrocarbon group, an alicyclic hydrocarbon group, and a group combining a chain hydrocarbon group and an alicyclic hydrocarbon group. The chain hydrocarbon group may be saturated or unsaturated, and may be linear or branched. For example, linear saturated alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, octyl group, decyl group, dodecyl group, pentadecyl group and hexadecyl group; branched saturated alkyl groups such as isopropyl group, sec-butyl group, tert-butyl group and 2-ethylhexyl group; linear unsaturated alkyl groups such as vinyl group, propenyl group, hexenyl group and octenyl group; and branched unsaturated alkyl groups such as 3-methyl-2-butenyl group. The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 12, more preferably 1 to 10, still more preferably 1 to 8, even more preferably 1 to 6, and even more preferably 1 to 4. The alicyclic hydrocarbon group may be monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as cyclopentyl group, cyclohexyl group, methylcyclohexyl group, dimethylcyclohexyl group, cycloheptyl group and cyclooctyl group. Examples of the polycyclic alicyclic hydrocarbon group include polycyclic cycloalkyl groups such as decahydronaphthyl group, adamantyl group, norbornyl group, methylnorbornyl group and groups as follows. TIFF2025087629000040.tif9159 The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and still more preferably 3 to 12. Examples of the group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group include groups formed by bonding the above-mentioned chain hydrocarbon group and the above-mentioned alicyclic hydrocarbon group, groups formed by bonding the above-mentioned alicyclic hydrocarbon group and the above-mentioned chain hydrocarbon group, and groups formed by bonding the above-mentioned chain hydrocarbon group, the above-mentioned alicyclic hydrocarbon group and the above-mentioned chain hydrocarbon group, etc., within the range allowed by the upper limit of the number of carbon atoms. Examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, anthryl group and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and still more preferably 6 to 10. Examples of a group combining an aliphatic hydrocarbon group and an aromatic hydrocarbon group include, within the range allowed by the upper limit of the number of carbon atoms, for example, a group formed by bonding the above-described chain hydrocarbon group and the above-described aromatic hydrocarbon group, a group formed by bonding the above-described aromatic hydrocarbon group and the above-described chain hydrocarbon group, a group formed by bonding the above-described aromatic hydrocarbon group and the above-described alicyclic hydrocarbon group via a single bond or the above-described chain hydrocarbon group, and the like. -CH 2 - in the hydrocarbon group being replaced by -O-, -S-, -CO- or -NR c - include a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkylthio group, an amino group, a thiol group, an alkoxycarbonyl group, an alkylsulfonyl group, and an alkylamino 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. The number of carbon atoms in the alkoxy group is, for example, 1 to 12, 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 alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. The number of carbon atoms in the alkylcarbonyl group is, for example, 2 to 12, preferably 2 to 8, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, and an isobutyryloxy group. The number of carbon atoms in the alkylcarbonyloxy group is, for example, 2 to 12, preferably 2 to 8, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3. Examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, and a butylthio group. The number of carbon atoms in the alkylthio group is, for example, 1 to 12, 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 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, etc. The number of carbon atoms of the alkoxycarbonyl group is preferably from 2 to 12, more preferably from 2 to 8, still more preferably from 2 to 6, yet more preferably from 2 to 4, and even more preferably from 2 to 3. Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, etc. The number of carbon atoms of the alkylsulfonyl group is preferably from 1 to 12, more preferably from 1 to 8, still more preferably from 1 to 6, yet more preferably from 1 to 4, and even more preferably from 1 to 3. Examples of the alkylamino group include a methylamino group, an ethylamino group, a propylamino group, a butylamino group, etc. The number of carbon atoms of the alkylamino group is preferably from 1 to 12, more preferably from 1 to 8, still more preferably from 1 to 6, yet more preferably from 1 to 4, and even more preferably from 1 to 3.
[0043] Ring W 1 is preferably a 4- to 12-membered heterocyclic ring containing a nitrogen atom or a heterocyclic ring containing the 4- to 12-membered ring, more preferably a 4- to 7-membered heterocyclic ring containing a nitrogen atom or a heterocyclic ring containing the 4- to 7-membered ring, still more preferably a 4- to 6-membered heterocyclic ring containing a nitrogen atom or a heterocyclic ring containing the 4- to 6-membered ring, and even more preferably a 4- to 6-membered heterocyclic ring containing a nitrogen atom or a polycyclic structure containing the 4- to 6-membered heterocyclic ring. -CO- is arranged at a position adjacent to the nitrogen atom, that is, Ring W 1 is preferably a lactam ring, and more preferably a lactam ring having a polycyclic structure. Ring W 1When the hydrogen atom contained in the complex ring is replaced with a halogen atom, a hydrocarbon group, or the like, it is preferably substituted with a halogen atom, a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or an alkylcarbonyloxy group having 2 to 4 carbon atoms, and more preferably substituted with an iodine atom, a fluorine atom, a hydroxy group, an alkylcarbonyl group having 2 to 4 carbon atoms, or an alkylcarbonyloxy group having 2 to 4 carbon atoms.
[0044] The structural unit having the group represented by the formula (II-x) 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, and a methacryloylthio group. Among them, the monomer that leads to the structural unit (II) is preferably a monomer having an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer.
[0045] The structural unit (II) is preferably a structural unit represented by the formula (IIA). TIFF2025087629000041.tif4056 [In the formula (IIA), all the symbols have the same meanings as described above.]
[0046] R x Examples of the halogen atom of R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R x Examples of the alkyl group of R include 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. It is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. R xExamples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, a triiodomethyl group, and the like. 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.
[0047] A X1 Examples of the divalent saturated hydrocarbon group of A include chain saturated hydrocarbon groups such as linear or branched alkanediyl groups, and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups, and those obtained by combining two or more of these groups may also be used. Specifically, methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, heptadecane-1,17-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group, propane-2,2-diyl group and other linear alkanediyl groups; Branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group; Monocyclic divalent alicyclic saturated hydrocarbon groups which are 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; Examples thereof include polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, and the like. The number of carbon atoms of the chain saturated hydrocarbon group is preferably 1 to 12, more preferably 1 to 8, still more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms of the alicyclic saturated hydrocarbon group is preferably 3 to 16, more preferably 3 to 12, and still more preferably 3 to 10. -CH 2 - in the saturated hydrocarbon group is replaced by -O-, -CO- or -NR d - Examples of the resulting group include a hydroxy group, a carboxy group, an amino group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkylamino group, an oxy group, a carbonyl group, an alkanedioxy group, an alkanedioxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylamino group, -CH 2 - in the alicyclic saturated hydrocarbon group is replaced by -O-, -CO- or -NR d - resulting group, a group formed by combining two or more of these groups, and the like. These replaced groups include the same groups as those exemplified in the present specification within the range where the upper limit of the number of carbon atoms permits. A X1 is preferably an alkanediyl group having 1 to 6 carbon atoms (where -CH 2 - in the alkanediyl group may be replaced by -O-, -CO- or -N(R d ))-), and more preferably a linear alkanediyl group having 1 to 4 carbon atoms (where -CH 2 - in the alkanediyl group may be replaced by -O-, -CO- or -N(R d ))-). A X is a single bond, -CO-O-(CH 2 )gg-*, -CO-NH-(CH 2 )gg-*, -CO-O-(CH 2) gg-O-* (* represents the bonding site with the carbonyl group. gg represents an integer from 1 to 4.) is preferably a single bond, -CO-O-(CH 2 ) gg-* (* represents the bonding site with the carbonyl group. gg represents an integer from 1 to 4.) is more preferably a single bond, and even more preferably a single bond.
[0048] Examples of the structural unit (II) include the following structural units. TIFF2025087629000042.tif42163
[0049] TIFF2025087629000043.tif55166 In the structural units represented by Formula (II-1) to Formula (II-10), R X Structural units in which the methyl group corresponding to is replaced by a hydrogen atom can also be cited as specific examples of the structural unit (II). Among them, the structural units represented by Formula (II-1), Formula (II-6) to Formula (II-9) are preferred, and the structural units represented by Formula (II-1) and Formula (II-7) are more preferred.
[0050] In the resin (A), the content of the structural unit represented by the formula (II) is 0.1 mol% or more, preferably 0.5 mol% or more, more preferably 0.8 mol% or more, even more preferably 1 mol% or more, still more preferably 3 mol% or more, even still more preferably 5 mol% or more, and even still more preferably 7 mol% or more, based on all the structural units of the resin (A). Also, 60 mol% or less, preferably 50 mol% or less, more preferably 40 mol% or less, even more preferably 30 mol% or less, still more preferably 25 mol% or less, even still more preferably 20 mol% or less, and even still more preferably 15 mol% or less. Specifically, 1 to 60 mol% can be mentioned, preferably 3 to 50 mol%, more preferably 5 to 40 mol%, even more preferably 5 to 30 mol%, still more preferably 5 to 25 mol%, even still more preferably 5 to 20 mol%, and even still more preferably 5 to 15 mol%.
[0051] 〈Structural unit (a1)〉 The structural unit (a1) is derived from a monomer having an acid-labile group (hereinafter sometimes referred to as "monomer (a1)"). The acid-labile group contained in the resin (A) is preferably a group represented by the formula (1) (hereinafter also referred to as group (1)) and / or a group represented by the formula (2) (hereinafter also referred to as group (2)). TIFF2025087629000044.tif2298[In the formula (1), R a1 , R a2 and R a3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R a1 and R a2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with the carbon atom to which they are bonded, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * represents a bonding site.] TIFF2025087629000045.tif2278[In the formula (2), R a1’ and R a2’ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R a3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R a2’ and R a3’ are bonded to each other to form a heterocyclic group having 3 to 20 carbon atoms together with the carbon atom to which they are bonded and X, and the -CH 2 - 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.]
[0052] R a1 , Ra2 and R a3 Examples of the alkyl group in 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, and the like. R a1 、R a2 and R a3 Examples of the alkenyl group in a3 include an ethenyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, an isooctenyl group, a nonenyl group. R a1 、R a2 and R a3 The alicyclic hydrocarbon group in a3 may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following group (* represents the bonding site), and the like. R a1 、R a2 and R a3 The number of carbon atoms of the alicyclic hydrocarbon group of a3 is preferably 3 to 16. TIFF2025087629000046.tif10159R a1 、R a2 and R a3 Examples of the aromatic hydrocarbon group in a3 include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a phenanthryl group, and the like. As the combined group, there are groups formed by 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, etc.), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having an alkyl group (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), aromatic hydrocarbon groups having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), aryl-cycloalkyl groups such as phenylcyclohexyl group, etc. Preferably, ma is 0 and na is 1. R a1 and R a2 When they 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 the bonding site with -O-. TIFF2025087629000047.tif27138
[0053] R a1’ 、R a2’ and R a3’ Examples of the hydrocarbon group in R a1 、R a2 and R a3 include alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. R a2’ and R a3’ When they are bonded to each other to form a heterocyclic group together with the carbon atom to which they are bonded and X, -C(R a1’ )(R a2’)-XR a3’ Examples of the group include the following: * represents a binding site. TIFF2025087629000048.tif19124R a1’ and R a2’ At least one of these is preferably a hydrogen atom. na' is preferably 0. R a1 , R a2 , R a3 , R a1 , R a2’ and R a3’ The halogen atom which may be contained includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0054] Examples of the group (1) include the following groups. In formula (1), R a1 , R a2 and R a3 is an alkyl group, ma = 0, and na = 1. As the group, a tert-butoxycarbonyl group is preferable. In formula (1), R a1 , R a2 together with the carbon atom to which they are attached form an adamantyl group, 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 the group (1) include the following groups: * represents a binding site. TIFF2025087629000049.tif150162
[0055] Specific examples of the group (2) include the following groups: * represents a bonding site. TIFF2025087629000050.tif55153
[0056] The monomer (a1) is preferably a monomer having an acid-labile group and an ethylenically unsaturated bond, more preferably a (meth)acrylic monomer having an acid-labile group. Among the (meth)acrylic monomers having an acid-labile group, those having an alicyclic hydrocarbon group with 5 to 20 carbon atoms are preferable. If a resin (A) having a structural unit derived from a monomer (a1) having a bulky structure such as an alicyclic hydrocarbon group is used in the resist composition, the resolution of the resist pattern can be improved.
[0057] As the structural unit derived from the (meth)acrylic monomer having the group (1), there may be mentioned a structural unit represented by the formula (a1-0) (hereinafter sometimes referred to as the structural unit (a1-0)), a structural unit represented by the formula (a1-1) (hereinafter sometimes referred to as the structural unit (a1-1)), or a structural unit represented by the formula (a1-2) (hereinafter sometimes referred to as the 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), more preferably 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. TIFF2025087629000051.tif45148 [In the formula (a1-0), the formula (a1-1), and the formula (a1-2), all the symbols have the same meanings as described above.]
[0058] R a01 、R a4 and R a5 The halogen atoms in are fluorine atom, chlorine atom, bromine atom or iodine atom. R a01 、R a4 and R a5Examples of the alkyl group which may have a halogen atom in the above formula include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, and an iodomethyl group. The number of carbon atoms in the alkyl group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. The alkyl group is preferably a methyl group or an ethyl group, and more preferably a methyl group. R a01 , R a4 and R a5 is preferably a hydrogen atom or a methyl group, and more preferably a methyl group. L a01 , L a1 and L a2 is preferably an oxygen atom or -O-(CH 2 ) k01 It is -CO-O- (wherein k01 is preferably an integer of any one of 1 to 4, more preferably 1), and more preferably an oxygen atom. R a02 , R a03 , R a04 , R a6 and R a7 The alkyl group, alkenyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and combinations thereof in the formula (1) include R a1 , R a2 and R a3 Examples of the groups include the same groups as those listed in the above. R a02 , R a03 , and R a04 The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. Ra6 and R a7 The alkyl group in is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, an isopropyl group or a t-butyl group, and still more preferably an ethyl group, an isopropyl group or a t-butyl group. R a6 and R a7 The alkenyl group in is preferably an alkenyl group having 2 to 6 carbon atoms, more preferably an ethenyl group, a propenyl group, an isopropenyl group or a butenyl group. R a02 、R a03 、R a04 、R a6 and R a7 The number of carbon atoms of the alicyclic hydrocarbon group of and R is preferably 5 to 12, more preferably 5 to 10. R a02 、R a03 、R a04 、R a6 and R a7 The number of carbon atoms of the aromatic hydrocarbon group of and R is preferably 6 to 12, more preferably 6 to 10. For the group formed by combining an alkyl group and an alicyclic hydrocarbon group, it is preferable that the total number of carbon atoms of these alkyl group and alicyclic hydrocarbon group is 18 or less. For the group formed by combining an alkyl group and an aromatic hydrocarbon group, it is preferable that the total number of carbon atoms of these alkyl group and aromatic hydrocarbon group is 18 or less. R a02 and R a03 are preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, more preferably a methyl group, an ethyl group, a phenyl group or a naphthyl group which may have a halogen atom. R a04 is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom or an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a halogen atom, more preferably a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group which may have a halogen atom. R a6and R a7 is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkenyl group having 2 to 6 carbon atoms which may have a halogen atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, more preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, a phenyl group or a naphthyl group which may have a halogen atom, and still more preferably an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group or a phenyl group which may have a halogen atom. m1 is preferably any integer from 0 to 3, more preferably 0 or 1. n1 is preferably any integer from 0 to 3, more preferably 0 or 1. n1’ is preferably 0 or 1.
[0059] Examples of the structural unit (a1-0) include structural units represented by any of formula (a1-0-1) to formula (a1-0-24) and the methyl group corresponding to R in the structural unit (a1-0) a01 which is replaced by a hydrogen atom, a halogen atom, a haloalkyl group 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 (a1-0-24) are preferred. TIFF2025087629000052.tif119160
[0060] Examples of the structural unit (a1-1) include structural units derived from the monomers described in JP-A-2010-204646. Among them, structural units represented by any of formula (a1-1-1) to formula (a1-1-7) and the methyl group corresponding to R in the structural unit (a1-1) a4 which is replaced by a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group are preferred, and structural units represented by any of formula (a1-1-1) to formula (a1-1-4) are more preferred. JPEG2025087629000053.jpg39169
[0061] Examples of the structural unit (a1-2) include a structural unit represented by any of Formula (a1-2-1) to Formula (a1-2-20) and a structural unit in which the methyl group corresponding to R in the structural unit (a1-2) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. The structural unit represented by any of Formula (a1-2-2), Formula (a1-2-5), Formula (a1-2-6), and Formula (a1-2-10) to Formula (a1-2-20) is preferred. a5 When the resin (A) contains the structural unit (a1-0) and / or the structural unit (a1-1) and / or the structural unit (a1-2), the total content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Also, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 70 mol% or less, even more preferably 65 mol% or less. Specifically, it is 10 to 95 mol%, preferably 15 to 90 mol%, more preferably 20 to 85 mol%, still more preferably 25 to 70 mol%, and even more preferably 30 to 70 mol%. When the resin (A) contains the structural unit (a1-0), the content thereof is 5 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more, still more preferably 20 mol% or more, even more preferably 25 mol% or more, still even more preferably 30 mol% or more, and even more preferably 35 mol% or more, based on all the structural units of the resin (A). Also, it is 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less, and even more preferably 60 mol% or less. Specifically, it is 5 to 80 mol%, preferably 5 to 75 mol%, and more preferably 10 to 70 mol%. When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), the total content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Further, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is 10 to 95 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, still more preferably 20 to 80 mol%, even more preferably 20 to 75 mol%, still even more preferably 20 to 70 mol%, and even more preferably 20 to 55 mol%.
[0062] Examples of the structural unit having the group (2) in the structural unit (a1) include a structural unit represented by the formula (a1-4) (hereinafter sometimes referred to as "structural unit (a1-4)"). TIFF2025087629000055.tif31119[In the formula (a1-4), all the symbols have the same meanings as described above.]
[0063] R a1 and R a17 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R a01 are the same as those exemplified by R R a1 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and still more preferably a hydrogen atom or a methyl group. R a17Examples of the alkoxy group in [compound name] include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, and hexyloxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, still more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. R a17 Examples of the alkoxyalkyl group in [compound name] 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 an alkoxyalkyl group having 2 to 4 carbon atoms, still more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group. R a17 Examples of the alkoxyalkoxy group in [compound name] 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 an alkoxyalkoxy group having 2 to 4 carbon atoms, still more preferably a methoxyethoxy group or an ethoxyethoxy group. R a17 Examples of the alkylcarbonyl group in [compound name] include acetyl group, propionyl group, and butyryl group. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 4 carbon atoms, more preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and still more preferably an acetyl group. R a17 Examples of the alkylcarbonyloxy group in [compound name] include acetyloxy group, propionyloxy group, and butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 4 carbon atoms, more preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and still more preferably an acetyloxy group. Ra17 is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 4 carbon atoms or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an 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.
[0064] A a11 Examples of the alkanediyl group of include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, etc., and branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, heptane-1,6-diyl group, octane-1,7-diyl group, nonane-1,8-diyl group, decane-1,9-diyl group, undecane-1,10-diyl group, etc. The number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 8, 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 a18 Examples of the alkyl group of include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group. A a11 When -CH 2 - contained in the alkanediyl group of is replaced by -O-, -CO- or -NR a18 -, the number of carbon atoms before replacement is taken as the number of carbon atoms of the alkanediyl group. A a11 -CH contained in the alkanediyl group of2 - is, -O-, -CO- or -NR a18 - as the replaced group include a hydroxy group, a carboxy group, a carbonyl group, an oxy group, an amino group (the -CH included in the methyl group 2 - is, -NR a18 - as the replaced group), an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylamino group (any -CH at any position included in the alkyl group 2 - is, -NR a18 - as the replaced group), a peptide group (the -CH included in the ethylene group 2 -CH 2 - is, -CO-NR a18 - as the replaced group), an alkanediyl-oxy group, an alkanediyl-oxycarbonyl group, an alkanediyl-carbonyl group, an alkanediyl-carbonyl-oxy group, an alkanediyl-sulfonyl group, an alkanediyl-thio group, an alkanediyl-amino group (any -CH at any position included in the alkanediyl group 2 - is, -NR a18 - as the replaced group), etc. These replaced groups include those similar to those exemplified herein within the range permitted by the upper limit of the number of carbon atoms. Examples of the alkylamino group include alkylamino groups having 1 to 11 carbon atoms, such as methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, octylamino group, etc. The number of carbon atoms of the alkylamino group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkanediylamino group include alkanediylamino groups having 1 to 11 carbon atoms, such as methyleneamino group, ethyleneamino group, propyleneamino group, etc. The number of carbon atoms of the alkanediylamino group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. For example, A a11 the -CH included in the alkanediyl group of 2 - is, -O-, -CO- or -NR a18-As the group replaced by, *-O-, *-CO-O-, *-O-CO-, *-CO-O-A a12 -CO-O-, *-O-CO-A a12 -O-, *-O-A a12 -CO-O-, *-CO-O-A a12 -O-CO-, *-O-CO-A a12 -O-CO-, *-CO-NR a18 - are mentioned. Among them, *-CO-O-, *-CO-O-A a12 -CO-O-, *-O-A a12 -CO-O-, *-CO-NR a18 - are preferred. Here, A a12 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents the bonding site with the carbon atom to which R a1 is bonded. The alkanediyl group of A a12 includes the same alkanediyl groups as A a11 within the range allowed by the upper limit of the number of carbon atoms. A a11 is preferably a single bond, *-CO-O- or *-CO-O-A a12 -CO-O-, more preferably a single bond, *-CO-O- or *-CO-O-CH 2 -CO-O-, and even more preferably a single bond or *-CO-O-. na1 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. na11 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. mc is preferably 0 or 1.
[0065] R a34 、R a35 and R a36 The hydrocarbon groups in include alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups and groups combining these. Examples of the alkyl group include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as 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). Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group and the like. Examples of the combined group include a group formed by combining the above-mentioned alkyl group and alicyclic hydrocarbon group (for example, 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. In particular, R a36 Examples thereof 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. R a35 and R a36 Examples of the divalent hydrocarbon group having 2 to 20 carbon atoms formed by 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 TIFF2025087629000057.tif15105
[0066] 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, more preferably a methyl group or an ethyl group. R a36 The hydrocarbon group of is preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these, more preferably 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 the alicyclic hydrocarbon group in are preferably unsubstituted. R a36 The aromatic hydrocarbon group in preferably has an aromatic ring having an aryloxy group having 6 to 10 carbon atoms.
[0067] -O-C(R a34 )(R a35 )-O-R a36 in the structural unit (a1-4) is eliminated by contact with an acid (for example, p-toluenesulfonic acid) to form a hydroxy group or a carboxy group. -X a1 -O-C(R a34 )(R a35 )-O-R a36 In the case of a benzene ring, 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, at least one is preferably bonded to the o-position or p-position, more preferably bonded to the p-position. In the case of a naphthalene ring, when the bonding position of A a11 is at the 1-position, it may be bonded to any of the 2nd to 8th positions, and when the bonding position of A a11 is at the 2nd position, it may be bonded to any of the 1st and 3rd to 8th positions. Among them, when the bonding position of A a11 is at the 1st position, at least one is preferably bonded to the 3rd to 6th positions, more preferably bonded to the 3rd or 4th position. When the bonding position of A a11 is at the 2nd position, it is preferably bonded to the 4th to 7th positions, more preferably bonded to the 5th or 6th position.
[0068] Examples of the structural unit (a1-4) include structural units derived from monomers described in JP-A-2010-204646. Preferably, the structural units represented by formula (a1-4-1) to formula (a1-4-42) and the hydrogen atom corresponding to R in the structural unit (a1-4) a1 are replaced by a halogen atom, a haloalkyl group or an alkyl group, 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), formula (a1-4-14), formula (a1-4-19), and formula (a1-4-20). When the resin (A) contains the structural unit (a1-4), the content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on the total of all the structural units of the resin (A). Also, 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 preferably 10 to 95 mol%, more preferably 15 to 90 mol%, still more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and still even more preferably 20 to 60 mol%.
[0069] Examples of the structural unit derived from the (meth)acrylic monomer having the group (2) also include the structural unit represented by formula (a1-5) (hereinafter sometimes referred to as "structural unit (a1-5)"). TIFF2025087629000059.tif4558[In formula (a1-5), all the symbols have the same meanings as described above.]
[0070] Ra8 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in (a1-0) are the same as those exemplified for R in the formula (a1-0). a01 The same ones as those exemplified above can be mentioned. In the formula (a1-5), R a8 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. L 51 is preferably an oxygen atom. L 52 and L 53 Among them, it is preferable that one is -O- and the other is -S-. s1 is preferably 1. s1' is preferably any integer from 0 to 2. Z a1 is preferably a single bond or *-CH 2 -CO-O-.
[0071] 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 the formulas (a1-5-1) to (a1-5-4) are preferable, and the structural unit represented by the formula (a1-5-1) or the formula (a1-5-2) is more preferable. When the resin (A) 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 (A). Also, it is 80 mol% or less, preferably 70 mol% or less, more preferably 60 mol% or less, still more preferably 50 mol% or less, even more preferably 45 mol% or less, still even more preferably 40 mol% or less, and even more preferably 30 mol% or less. Specifically, 1 to 50 mol% is preferable, 3 to 45 mol% is more preferable, 5 to 40 mol% is still more preferable, and 5 to 30 mol% is even more preferable.
[0072] 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)"). TIFF2025087629000061.tif3481[In the formula (a1-6), all the symbols have the same meanings as described above.]
[0073] R a61 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R a01 are the same as those exemplified above, such as the R of the formula (a1-0). 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 even 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, or a methacryloyloxy group. R a62 and R a63 Examples of the ring formed by R a62 and R a63 bonding to each other include an adamantane ring, a cyclopentane ring, or a cyclohexane ring. Specifically, when R a62 and R a63 bond to each other to form a ring, examples of -C(R a64 )(R TIFF2025087629000062.tif32110
[0074] L a61 and L a62 Examples of the alkanediyl group having 1 to 4 carbon atoms in L L a61 and L a62 are preferably each independently a methylene group or an ethylene group. X a61 is preferably a single bond or -CO-O-*, and more preferably a single bond. X a62 is preferably a single bond or *-O-L a61 -, and more preferably a single bond.
[0075] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms for Ar include a phenylene group, 1-naphthylene group, 2-naphthylene group, 1-anthrylene group, 9-anthrylene group, biphenylene group, 1-phenanthrylene group, 2-phenanthrylene group, and the like. Examples of the substituent that the aromatic hydrocarbon group may have include a halogen atom, hydroxy group, alkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkoxyalkyl group having 2 to 12 carbon atoms, alkoxyalkoxy group having 2 to 12 carbon atoms, alkylcarbonyl group having 2 to 4 carbon atoms, alkylcarbonyloxy group having 2 to 4 carbon atoms, acryloyloxy group, or methacryloyloxy group.
[0076] Examples of the halogen atom include a fluorine atom, iodine atom, chlorine atom, bromine atom, and the like. Examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group. The alkyl group preferably has 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. Examples of the alkoxy group include a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group. The alkoxy group preferably has 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. Examples of the alkoxyalkyl group include a methoxymethyl group, ethoxyethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxymethyl group, tert-butoxymethyl group. The alkoxyalkyl group preferably has 2 to 8 carbon atoms, more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group. Examples of the alkoxyalkoxy group include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a methoxyethoxy group or an ethoxyethoxy group. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, more preferably an acetyl group. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, more preferably an acetyloxy group. Examples of the substituent include a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms. More preferably, the substituent is a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group. Even more preferably, the substituent is a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group. Ar is preferably a phenylene group which may have a substituent, more preferably a phenylene group which may have a hydroxy group.
[0077] 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, R a61A structural unit in which a hydrogen atom corresponding to the following is replaced by a methyl group or the like, and in the following structural unit, R a61 A structural unit in which a methyl group corresponding to the following is replaced by a hydrogen atom or the like is also cited as the structural unit (a1-6). TIFF2025087629000063.tif226161
[0078] When the resin (A) contains the structural unit (a1-6), the content thereof is 3 mol% or more, preferably 5 mol% or more, more preferably 7 mol% or more, still more preferably 10 mol% or more, even more preferably 20 mol% or more, still even more preferably 30 mol% or more, and even more preferably 40 mol% or more, based on all the structural units of the resin (A). Also, 80 mol% or less is cited, preferably 75 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, still more preferably 7 to 70 mol%, even more preferably 7 to 65 mol%, and particularly preferably 10 to 65 mol%.
[0079] Also, examples of the structural unit (a1) include the following structural units. TIFF2025087629000064.tif33167
[0080] When the resin (A) contains structural units represented by the formulas (a1-7-1) to (a1-7-7), the content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Also, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, 10 to 95 mol% is preferable, 15 to 90 mol% is more preferable, 20 to 85 mol% is still more preferable, 20 to 70 mol% is even more preferable, and 20 to 60 mol% is particularly preferable.
[0081] In addition, examples of the structural unit (a1) also include the following structural units. TIFF2025087629000065.tif51120 When the resin (A) contains structural units represented by the formulas (a1-8-1) to (a1-8-3), the content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Also, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and even more preferably 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.
[0082] 〈Structural unit (s)〉 The structural unit(s) is / are derived from monomers having no acid-labile group (hereinafter sometimes referred to as "monomer(s)"). As the monomer(s) from which the structural unit(s) is / are derived, monomers having no acid-labile group known in the resist field can be used. The structural unit(s) preferably has a hydroxy group, a carboxy group or a lactone ring. By using a resin containing a structural unit having a hydroxy group or a carboxy group and no acid-labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and no acid-labile group (hereinafter sometimes referred to as "structural unit (a3)") in the resist composition of the present invention, the resolution of the resist pattern and the adhesion to the substrate can be improved. In addition to the above-described structural units, the structural unit(s) includes a structural unit having a halogen atom (hereinafter sometimes referred to as "structural unit (a4)"), provided that the structural unit represented by formula (I) is excluded), 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.
[0083] 〈Structural unit (a2)〉 The structural unit (a2) is a structural unit represented by formula (a2) and has an alcoholic hydroxy group, a phenolic hydroxy group or a carboxy group. TIFF2025087629000066.tif4094[In 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 -CH 2 - contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a28 -. R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L a21represents a single bond or a hydrocarbon group having 1 to 28 carbon atoms, and the hydrocarbon group may have a substituent, and -CH 2 - may be replaced by -O-, -CO-, -S- or -SO 2 -. L a22 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom, and -CH 2 - may be replaced by -O- or -CO-. na2 represents any integer from 1 to 5. When na2 is 2 or more, a plurality of L a22 may be the same as or different from each other.]
[0084] R a2 Examples of the halogen atom in R include a fluorine atom, an iodine atom, a chlorine atom, a bromine atom and the like. R a2 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group. The number of carbon atoms of the alkyl group is preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 or 2. R a2 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and still more preferably a hydrogen atom or a methyl group.
[0085] A a21Examples of the alkanediyl group include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, and branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, heptane-1,6-diyl group, octane-1,7-diyl group, nonane-1,8-diyl group, decane-1,9-diyl group, undecane-1,10-diyl group. The number of carbon atoms in the alkanediyl group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 4, even still more preferably 1 to 3, and even more preferably 1 or 2. R a28 Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, and tert-butyl group. A a21 When -CH 2 - contained in the alkanediyl group of A is replaced by -O-, -CO- or -NR a28 -, the number of carbon atoms before replacement is defined as the number of carbon atoms of the alkanediyl group. A a21 Examples of the group in which -CH 2 - contained in the alkanediyl group of A is replaced by -O-, -CO- or -NR a28 - include hydroxy group (the group in which -CH 2 - contained in the methyl group is replaced by -O-), carboxy group (the group in which -CH 2 -CH 2 - contained in the ethyl group is replaced by -O-CO-), carbonyl group (the group in which -CH 2 - contained in the methylene group is replaced by -CO-), and oxy group (the group in which -CH 2- is a group replaced by -O-), an amino group (-CH contained in the methyl group) 2 - is -NR a28 - replaced by -), an alkoxy group (-CH at any position contained in the alkyl group) 2 - is a group replaced by -O-), an alkoxycarbonyl group (-CH at any position contained in the alkyl group) 2 -CH 2 - is a group replaced by -O-CO-), an alkylcarbonyl group (-CH at any position contained in the alkyl group) 2 - is a group replaced by -CO-), an alkylcarbonyloxy group (-CH at any position contained in the alkyl group) 2 -CH 2 - is a group replaced by -CO-O-), an alkylamino group (-CH at any position contained in the alkyl group) 2 - is -NR a28 - replaced by -), a peptide group (-CH contained in the ethylene group) 2 -CH 2 - is -CO-NR a28 - replaced by -), an alkanediyl-oxy group (-CH contained in the alkanediyl group) 2 - is a group replaced by -O-), an alkanediyl-oxycarbonyl group (-CH at any position contained in the alkanediyl group) 2 -CH 2 - is a group replaced by -O-CO-), an alkanediyl-carbonyl group (-CH at any position contained in the alkanediyl group) 2 - is a group replaced by -CO-), an alkanediyl-carbonyl-oxy group (-CH at any position contained in the alkanediyl group) 2 -CH 2 - is a group replaced by -CO-O-), an alkanediyl-amino group (-CH at any position contained in the alkanediyl group) 2 - is -NR a28 - replaced by -), etc. are 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. Among them, -CH contained in the alkanediyl group of A a21 2 - is, -O-, -CO- or -NR a28 - as the replaced group includes, *-O-, *-CO-O-, *-O-CO-, *-CO-O-A a22 -CO-O-, *-O-CO-A a22 -O-, *-O-A a22 -CO-O-, *-CO-O-A a22 -O-CO-, *-O-CO-A a22 -O-CO-, *-CO-NR a28 - are included. Among them, *-CO-O-, *-CO-O-A a22 -CO-O-, *-O-A a22 -CO-O-, *-CO-NR a28 - are preferred. Here, A a22 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents the bonding site with the carbon atom to which R a2 is bonded. The alkanediyl group of A a22 includes the same alkanediyl group as A a21 within the range allowed by the upper limit of the number of carbon atoms. A a21 is preferably a single bond, *-CO-O- or *-CO-O-A a22 -CO-O-, more preferably a single bond, *-CO-O- or *-CO-O-CH 2 -CO-O-, and even more preferably a single bond or *-CO-O-.
[0086] L a21 The hydrocarbon group in is a (na2 + 1)-valent hydrocarbon group, and examples include linear or branched chain hydrocarbon groups, monocyclic or polycyclic (including spiro rings, condensed rings, bridged rings, etc.) alicyclic hydrocarbon groups, cyclic hydrocarbon groups such as aromatic hydrocarbon groups, and groups formed by combining two or more of these groups (for example, hydrocarbon groups formed from alicyclic hydrocarbon groups or aromatic hydrocarbon groups and chain hydrocarbon groups) may also be used. Examples of the chain hydrocarbon group include divalent to hexavalent chain hydrocarbon groups such as alkanediyl groups, alkanetriyl groups, alkanetetrayl groups, alkanepentayl groups, and alkanhexayl groups. Examples of the alkanediyl group include, for example, Aa21 Examples thereof include the same alkandiyl groups. Examples of the alkanetriyl group include a methanetriyl group, an ethanetriyl group, a propanetriyl group, a butanetriyl group, a pentanetriyl group, a hexanetriyl group, a heptanetriyl group, an octanetriyl group, a nonanetriyl group, a decanetriyl group, an undecanetriyl group, a dodecanetriyl group, a tridecanetriyl group, a tetradecanetriyl group, a pentadecanetriyl group, a hexadecanetriyl group, a heptadecanetriyl group, and the like. Examples of the alkanetetrayl group include a methanetetrayl group, an ethanetetrayl group, a propanetetrayl group, a butanetetrayl group, a pentanetetrayl group, a hexanetetrayl group, a heptanetetrayl group, an octanetetrayl group, a nonanetetrayl group, a decanetetrayl group, an undecanetetrayl group, a dodecanetetrayl group, a tridecanetetrayl group, a tetradecanetetrayl group, a pentadecanetetrayl group, a hexadecanetetrayl group, a heptadecanetetrayl group, and the like. Examples of the alkanepentayl group include a methanepentayl group, an ethanepentayl group, a propanepentayl group, a butanepentayl group, a pentanepentayl group, a hexanepentayl group, and the like. Examples also include groups in which one or more hydrogen atoms of the above-described groups are replaced with a bonding site, and the like. L a21 The number of carbon atoms of 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, still more preferably 1 to 6, still even more preferably 1 to 5, and particularly preferably 1 to 4. L a21 Examples of the monocyclic and polycyclic alicyclic hydrocarbon groups in L include the following alicyclic hydrocarbon groups and the like. The bonding site can be at any position. TIFF2025087629000067.tif46168For example, divalent to hexavalent alicyclic hydrocarbon groups such as cycloalkanediyl groups, cycloalkanetriyl groups, cycloalkanetetrayl groups, cycloalkanepentayl groups, cycloalkanhexayl groups, etc. can be mentioned. Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, cyclopropanetriyl group, cyclobutanetriyl group, cyclopentanetriyl group, cyclohexanetriyl group, cycloheptanetriyl group, cyclooctanetriyl group, cyclodecanetriyl group, cyclopropanetetrayl group, cyclobutanetetrayl group, cyclopentanetetrayl group, cyclohexanetetrayl group, cycloheptanetetrayl group, cyclooctanetetrayl group, cyclodecanetetrayl group, etc. and polycyclic alicyclic hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, decahydronaphthalenediyl group, bicyclo[3.3.0]octanediy group, norbornanetriyl group, adamantanetriyl group, decahydronaphthalenetriyl group, bicyclo[3.3.0]octanetriyl group, norbornanetetrayl group, adamantanetetrayl group, decahydronaphthalenetetrayl group, bicyclo[3.3.0]octanetetrayl group, etc. can be mentioned. In addition, groups in which one or more hydrogen atoms of the above-mentioned groups are replaced at the bonding site, etc. can also be mentioned. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 18, still more preferably 3 to 16, even more preferably 3 to 12, still even more preferably 6 to 12, and particularly preferably 6 to 10. L a21 Examples of the aromatic hydrocarbon group in L include divalent to hexavalent aromatic hydrocarbon groups such as arylene groups, arenetriyl groups, arenetetrayl groups, arenepentayl groups, arenexayl groups, etc. Specifically, examples include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, a benzenetriyl group, a naphthalenetriyl group, an anthracenetriyl group, a biphenylenetriyl group, a phenanthrenetriyl group, a benzenetetrayl group, a naphthalenetetrayl group, an anthracenetetrayl group, a biphenylenetetrayl group, a phenanthrenetetrayl group, and the like. In addition, examples also include a group in which one or more hydrogen atoms of the above-described group are replaced with a bonding site, 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 even more preferably 6 to 10. Examples of the group combined with two or more types include a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group, a group combining an aromatic hydrocarbon group and a chain hydrocarbon group, a group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, a group combining an alicyclic hydrocarbon group, a chain hydrocarbon group, and an aromatic hydrocarbon group, and the like. In the combination, the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and the chain hydrocarbon group may each be combined with two or more types. Also, any group may be bonded to A a21 and L a22 and may be bonded thereto. Examples of the group in which -CH 2 - contained in the hydrocarbon group is replaced with -O-, -S-, -SO 2 -, or -CO- include a hydroxy group (a group in which -CH 2 - contained in the methyl group is replaced with -O-), a carboxy group (a group in which -CH 2 -CH 2 - contained in the ethyl group is replaced with -O-CO-), a thiol group (a group in which -CH 2 - contained in the methyl group is replaced with -S-), an alkoxy group (a group in which -CH 2 - at any position contained in the alkyl group is replaced with -O-), an alkylthio group (a group in which -CH 2 - at any position contained in the alkyl group is replaced with -S-), an alkoxycarbonyl group (a group in which -CH 2 -CH2 - is a group replaced by -O-CO-, an alkylsulfonyl group (any -CH at any position in the alkyl group) 2 - is 2 - replaced by -SO 2 - is a group replaced by -CO-, an alkylcarbonyl group (any -CH at any position in the alkyl group) 2 -CH 2 - is a group replaced by -CO-O-, an alkoxycarbonyloxy group, (any -CH at any position in the alkyl group) 2 -CH 2 -CH 2 - is a group replaced by -O-CO-O-, an oxy group (any -CH in the methylene group) 2 - is a group replaced by -O-, a carbonyl group (any -CH in the methylene group) 2 - is a group replaced by -CO-, a thio group (any -CH in the methylene group) 2 - is a group replaced by -S-, a sulfonyl group (any -CH in the methylene group) 2 - is 2 - replaced by -SO 2 - is a group replaced by -O-, an alkanedioxy group (any -CH at any position in the alkanedioxy group) 2 -CH 2 - is a group replaced by -O-CO-, an alkanediylcarbonyl group (any -CH at any position in the alkanediyl group) 2 - is a group replaced by -CO-, an alkanediylcarbonyl group (any -CH at any position in the alkanediyl group) 2 -CH 2 - is a group replaced by -CO-O-, an alkanediylsulfonyl group (any -CH at any position in the alkanediyl group) 2 - is 2 - replaced by -SO 2- is a group replaced by -S-, 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 group formed by combining two or more of these groups, etc. Also included are groups in which one or more hydrogen atoms of these groups are replaced by a bonding site, etc. Examples of the alkoxy group include alkoxy groups having 1 to 27 carbon atoms, such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group, etc. The number of carbon atoms of the alkoxy group is 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 alkylthio group include alkylthio groups having 1 to 27 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, etc. The number of carbon atoms of the alkylthio group is 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 27 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group and the like. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 28 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 27 carbon atoms, such as acetyloxy group, propionyloxy group, butyryloxy group and the like. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 26 carbon atoms, such as butoxycarbonyloxy group and the like. The number of carbon atoms of the alkoxycarbonyl group is 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 of the alkylcarbonyl group is 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 of the alkylcarbonyloxy group and the alkoxycarbonyloxy group is each 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 alkylsulfonyl group include alkylsulfonyl groups having 1 to 27 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group and the like. The number of carbon atoms of the alkylsulfonyl group is 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 alkanedioxy group include alkanedioxy groups having 1 to 27 carbon atoms, such as methyleneoxy group, ethyleneoxy group, propanedioxy group, butanedioxy group, pentanedioxy group and the like. The number of carbon atoms of the alkanedioxy group is 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 27 carbon atoms, such as a methylene-oxycarbonyl group, an ethylene-oxycarbonyl group, a propanediyl-oxycarbonyl group, and a butanediyl-oxycarbonyl group. Examples of the alkanediyl-carbonyl group include alkanediyl-carbonyl groups having 2 to 28 carbon atoms, such as a methylene-carbonyl group, an ethylene-carbonyl group, a propanediyl-carbonyl group, a butanediyl-carbonyl group, and a pentanediyl-carbonyl group. Examples of the alkanediyl-carbonyloxy group include alkanediyl-carbonyloxy groups having 2 to 27 carbon atoms, such as a methylene-carbonyloxy group, an ethylene-carbonyloxy group, a propanediyl-carbonyloxy group, and a butanediyl-carbonyloxy group. The number of carbon atoms of the alkanediyl-oxycarbonyl group is 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 of the alkanediyl-carbonyl group is 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 of the alkanediyl-carbonyloxy group is 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 27 carbon atoms, such as a methylene-thio group, an ethylene-thio group, and a propanediyl-thio group. The number of carbon atoms of the alkanediyl-thio group is 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-sulfonyl group include alkanediyl-sulfonyl groups having 1 to 27 carbon atoms, such as a methylene-sulfonyl group, an ethylene-sulfonyl group, and a propylene-sulfonyl group. The number of carbon atoms of the alkanediyl-sulfonyl group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.
[0087] Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 27 carbon atoms, such as a cyclohexyloxy group. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 27 carbon atoms, such as a cyclohexylmethoxy group. Examples of the aromatic hydrocarbon group-carbonyl oxy group include aromatic hydrocarbon group-carbonyl oxy groups having 7 to 27 carbon atoms, such as a benzoyloxy group. Examples of the aromatic hydrocarbon group-carbonyl group include aromatic hydrocarbon group-carbonyl groups having 7 to 28 carbon atoms, such as a benzoyl group. Examples of the aromatic hydrocarbon group-oxy group include aromatic hydrocarbon group-oxy groups having 6 to 27 carbon atoms, such as a phenyloxy group.
[0088] In addition, -CH 2 - contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO 2 - to give groups such as the following. Among the groups represented below, groups in which -O- is replaced with -S- and -CO- is replaced with -SO 2 - are also included. The bonding site can be at any position. TIFF2025087629000068.tif47168 -CH contained in the group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group 2 - may be replaced with -O-, -S-, -CO- or -SO 2 - to give groups such as the following. The bonding site can be at any position. TIFF2025087629000069.tif26164L a21 The hydrocarbon group in L may have one or more substituents. Examples of the substituent include a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, an alkyl group having 1 to 16 carbon atoms (wherein -CH 2 - contained in the alkyl group may be replaced with -O- or -CO-), an acryloyloxy group or a methacryloyloxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. L a21 In the hydrocarbon group in L, by having a halogen atom as a substituent, it can substantially have a substituent such as a haloalkyl group. Examples of the haloalkyl group include an alkyl fluoride group, an alkyl chloride group, an alkyl bromide group, an alkyl iodide group, etc. For example, a chloromethyl group, a bromomethyl group, an iodomethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, etc. can be mentioned. The number of carbon atoms of the haloalkyl group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. L a21 Since the hydrocarbon group of L contains a branched structure, L a21 can 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, etc. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 10, still more preferably 1 to 8, even more preferably 1 to 6, still even more preferably 1 to 4, and even more preferably 1 to 3. L a21 When the -CH 2 - contained in the hydrocarbon group of L is replaced by a group such as -O- or -CO-, L a21can substantially have substituents such as a hydroxy group, a carboxy group, an alkoxy group, a thiol group, a sulfonyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxyalkyl group, an alkoxyalkoxy group, an acryloyloxy group, a methacryloyloxy group, etc. The number of carbon atoms of the alkoxy group is preferably 1 to 12, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. The number of carbon atoms of the alkoxycarbonyl group, the alkylcarbonyl group, and the alkylcarbonyloxy group is preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3. The number of carbon atoms of the alkoxyalkyl group and the alkoxyalkoxy group is preferably 2 to 12, more preferably 2 to 8, still more preferably 2 to 6, and even more preferably 2 to 4. Examples of the above groups include those similar to those exemplified in this specification. L a21 Examples of the substituent that the hydrocarbon group in may optionally have include a halogen atom, a haloalkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 12 carbon atoms (the -CH 2 - contained in the alkyl group may be replaced by -O- or -CO-).) are preferred, a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 10 carbon atoms (the -CH 2 - contained in the alkyl group may be replaced by -O- or -CO-).) are more preferred, a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms are still more preferred, a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group are even more preferred, and a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, a methoxy group, or an ethoxyethoxy group are still even more preferred. Also, when the alkanediyl group of L a21 is replaced by -O- or -CO-, etc., for example, *-L a23-X a21 -(L a23 represents an alkanediyl group having 1 to 8 carbon atoms, and X a21 represents -O-, -O-CO-, -CO-O- or -O-CO-O-, and * represents the bonding site with A a21 .) It is also preferable that it is so. L a21 is a single bond, an optionally substituted chain hydrocarbon group having 1 to 12 carbon atoms (however, -CH 2 - contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an optionally substituted cyclic hydrocarbon group having 3 to 20 carbon atoms (however, -CH 2 - contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), or a group formed by combining an optionally substituted chain hydrocarbon group having 1 to 8 carbon atoms and an optionally substituted cyclic hydrocarbon group having 3 to 20 carbon atoms (however, -CH 2 - contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH 2 - contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-).) It is preferable that it is so, an optionally substituted chain hydrocarbon group having 1 to 10 carbon atoms (however, -CH 2 - contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an optionally substituted cyclic hydrocarbon group having 3 to 18 carbon atoms (however, -CH 2 - contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), or a group formed by combining an optionally substituted chain hydrocarbon group having 1 to 6 carbon atoms and an optionally substituted cyclic hydrocarbon group having 3 to 18 carbon atoms (however, -CH 2 - contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH 2 - contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-).) It is more preferable that it is so.
[0089] L a22 Examples of the chain hydrocarbon group having 1 to 12 carbon atoms for L include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, etc., and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, 1-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-dimethylpropane-1,3-diyl group, pentane-2,4-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, pentane-2,4-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, etc. The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6, and even more preferably 1 to 4. The group in which -CH 2 - in the chain hydrocarbon group is replaced by -O- or -CO- includes those similar to those exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms. L a22 The fluorine atom that L has may be one or two or more. na2 is preferably any integer from 1 to 4, and more preferably any integer from 1 to 3. L a21 Examples of the structural unit (a2) when L is a single bond or a chain hydrocarbon group include, for example, the following structural units. Among the following structural units, the structural units in which the methyl group corresponding to R a2 is replaced by a hydrogen atom or the like are also suitable structural units of the structural unit (a2) in the same manner as the following structural units. TIFF2025087629000070.tif67168
[0090] When producing a resist pattern from the resist composition of the present invention, when using a high-energy ray such as a KrF excimer laser (248 nm), an electron beam, or EUV (extreme ultraviolet light) as the exposure light source, as the structural unit (a2), a structural unit (a2) having a phenolic hydroxy group is preferable, and it is more preferable to use the structural unit (a2-A) described later. Further, when using an ArF excimer laser (193 nm) or the like, as the structural unit (a2), a structural unit (a2) having an alcoholic hydroxy group is preferable, and it is more preferable to use the structural unit (a2-C) described later. The structural unit (a2) may contain one kind alone or two or more kinds.
[0091] In the structural unit (a2), L a21 When it is a cyclic hydrocarbon group, examples of the structural unit having a phenolic hydroxy group or a carboxy group include a structural unit represented by the formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A)"). TIFF2025087629000071.tif30128[In the formula (a2-A), all the symbols have the same meanings as described above.] R a2 and A a21 are the same groups as those exemplified by the formula (a2), respectively. R a27 Examples of the halogen atom of R include a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom. R a27Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include trifluoromethyl group, difluoromethyl group, methyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, ethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, butyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, pentyl group, hexyl group, perfluorohexyl group, chloromethyl group, bromomethyl group, iodomethyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a27 Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group, tert-butoxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, still more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. R a27 Examples of the alkoxyalkyl group include methoxymethyl group, ethoxyethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxymethyl group, tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably a methoxymethyl group or an ethoxyethyl group, and still more preferably a methoxymethyl group. R a27 Examples of the alkoxyalkoxy group include methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, propoxymethoxy group, isopropoxymethoxy group, butoxymethoxy group, sec-butoxymethoxy group, tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group. R a27 Examples of the alkylcarbonyl group of R 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 Examples of the alkylcarbonyloxy group of R 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 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, 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, even more preferably 1 or 2. na21 is preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, 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 2-position to 8-position, and when the bonding position of A a21 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 a21 is at the 1-position, at least one is preferably bonded to the 3-position to 6-position, more preferably bonded to the 3-position or 4-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.
[0092] 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 formulas (a2-2-1) to (a2-2-32), formulas (a2-3-1) to (a2-3-24), and structural units represented by formulas (a2-2-1) to (a2-2-32), formulas (a2-3-1) to (a2-3-24), where the methyl group corresponding to R in the structural unit (a2-A) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. a2 Examples thereof include structural units in which the methyl group corresponding to R in the structural unit (a2-A) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. TIFF2025087629000072.tif107170
[0093] When the resin (A) contains the structural unit (a2-A), the content of the structural unit (a2-A) is preferably 5 mol% or more, more preferably 10 mol% or more, still more preferably 15 mol% or more, and even more preferably 20 mol% or more, based on all the structural units. Also, it is preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less, even more preferably 60 mol% or less, still even more preferably 50 mol% or less, still more preferably 45 mol% or less, and even more preferably 40 mol% or less. Specifically, it is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, still more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%. The structural unit (a2-A) is a compound that induces the structural unit (a2-A) (for example, the -CH 2 -C(-R a2 )- of the structural unit (a2-A) is the CH of the double bond before cleavage 2 =C(-R a2) in the state of a compound (such as (a2-A’)) can be polymerized and incorporated into the resin (A). Further, for example, after polymerization using the structural unit (a1-4), it can be incorporated into the resin (A) by treatment with an acid such as p-toluenesulfonic acid. Also, after polymerization using acetoxystyrene or the like, the structural unit (a2-A) can be incorporated into the resin (A) by treatment with an alkali such as tetramethylammonium hydroxide.
[0094] In the structural unit (a2), when L a21 is a cyclic hydrocarbon group, examples of the structural unit having an alcoholic hydroxy group or a carboxy group include the structural unit represented by the formula (a2-B) (hereinafter sometimes referred to as "structural unit (a2-B)"), the structural unit represented by the formula (a2-C) (hereinafter sometimes referred to as "structural unit (a2-C)"), and the structural unit represented by the formula (a2-D) (hereinafter sometimes referred to as "structural unit (a2-D)"). TIFF2025087629000074.tif45100 [In the formulas (a2-B) and (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-(CH 2 ) k2 -CO-O- represents, and k2 represents an integer of 1 to 7. * represents the bonding site with -CO-. X a2 represents a single bond or -CO-. R a25 and R a26 each independently represent a hydrogen atom, a methyl group, or a hydroxy group. nB2 represents an integer of 1 to 5. When nB2 is 2 or more, a plurality of X a2 may be the same as or different from each other. nB22 represents an integer of 0 to 8. When nB22 is 2 or more, a 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, a plurality of Rs a27 may be the same as or different from each other.]
[0095] L a25 is preferably -O-, -O-(CH 2 ) 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, a carboxy group, an optionally halogenated C1-4 alkyl group, a C1-4 alkoxy group or a C2-8 alkoxyalkoxy group, 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. 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.
[0096] 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 Rs in the following structural units a2Examples of the structural unit in which the methyl group or hydrogen atom corresponding to it is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group include those. 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 preferred. When the resin (A) contains the structural unit (a2-B) or the structural unit (a2-C), the content thereof is 1 mol% or more, preferably 2 mol% or more, based on all the structural units of the resin (A). Further, it is 45 mol% or less, preferably 40 mol% or less, more preferably 35 mol% or less, still more preferably 20 mol% or less, and even more preferably 10 mol% or less. Specifically, 1 to 45 mol% is mentioned, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, still more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol%.
[0097] Examples of the structural unit having an alcoholic hydroxy group in the structural unit (a2) include the structural unit represented by formula (a2-D) (hereinafter sometimes referred to as "structural unit (a2-D)"). TIFF2025087629000076.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 fluorinated alkyl group having 1 to 4 carbon atoms. L a24 represents a single bond or an alkanediyl group having 1 to 3 carbon atoms, and the alkanediyl group may be substituted with a fluorine atom. nD2 represents any integer from 1 to 5. When nD2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. nD22 represents any integer from 0 to 4. When nD22 is 2 or more, the plurality of Ra27 may be the same as or different from each other. However, 1 ≦ nD2 + nD22 ≦ 5.
[0098] R a21 and R a22 Examples of the alkyl fluoride groups of R and R include, independently of each other, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, and the like. R a21 and R a22 is preferably a trifluoromethyl group. L a24 Examples of the alkanediyl group of L 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 alkyl group having 1 to 4 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group. 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 in parentheses is bonded to the para position. nD22 is preferably any integer from 0 to 3, more preferably any integer from 0 to 2, even more preferably 0 or 1, and even more preferably 0. As the structural unit (a2-D), a structural unit represented by the following formula (a2-D1) (hereinafter, may be referred to as "structural unit (a2-D1)") is more preferable. TIFF2025087629000077.tif51108In formula (a2-D1), R a2 , A a21 , R a27 , nD2 and nD22 have the same meaning as in formula (a2-D).] In formula (a2-D1), R a2 is preferably a hydrogen atom or a methyl group. A a21 is preferably a single bond.
[0099] Examples of the structural unit (a2-D) include the structural units described below. TIFF2025087629000078.tif62167In the structural units represented by formula (a2-D-1) to formula (a2-D-8), structural units in which the hydrogen atom corresponding to R a2 is replaced by a methyl group or the like, and in the structural units represented by formula (a2-D-9) to formula (a2-D-16), structural units in which the methyl group corresponding to R a2 is replaced by 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 formula (a2-D-1) to formula (a2-D-8) are preferred, the structural units represented by formula (a2-D-1) to formula (a2-D-4) are more preferred, and the structural unit represented by formula (a2-D-1) is even more preferred.
[0100] When the resin (A) contains the structural unit (a2-D), its content is 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 (A). Also, it is preferably 80 mol% or less, more preferably 75 mol% or less, still more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, still more preferably 10 to 70 mol%, and even more preferably 10 to 65 mol%.
[0101] 〈Structural unit (a3)〉 The lactone ring of the structural unit (a3) may be a monocyclic ring such as a β-propiolactone ring, γ-butyrolactone ring, or δ-valerolactone ring, or a condensed ring of a monocyclic lactone ring and another ring. Preferably, 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)) can be mentioned.
[0102] The structural unit (a3) is preferably a structural unit represented by the 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. TIFF2025087629000079.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-(CH 2 ) k3 -CO-O- (where k3 represents an integer from 1 to 7). L a7 represents -O-, *-O-L a8 -O-, *-O-L a8 -CO-O-, *-O-L a8 -CO-O-L a9 -CO-O- or *-O-L a8 -O-CO-L a9 -O-. L a8 and L a9 each independently represents an alkanediyl group having 1 to 6 carbon atoms. * represents the bonding site with the carbonyl group. R a18 、R a19 、R a20 and R a24 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X a3 represents -CH 2 - or an oxygen atom. R a21represents an aliphatic hydrocarbon group having 1 to 4 carbon atoms. R a22 、R a23 and R a25 each independently represent a carboxy group, a cyano group or an aliphatic hydrocarbon group having 1 to 4 carbon atoms. p1 represents any integer from 0 to 5. q1 represents any integer from 0 to 3. r1 represents any integer from 0 to 3. w1 represents any integer from 0 to 8. When p1, q1, r1 and / or w1 is 2 or more, a plurality of R a21 、R a22 、R a23 and / or R a25 may be the same as or different from each other.
[0103] R a21 、R a22 、R a23 and R a25 Examples of the aliphatic hydrocarbon group in R a18 、R a19 、R a20 and R a24 include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group and tert-butyl group. a01 Examples of the halogen atom and the alkyl group which may have a halogen atom in L a8 and L a9 include the same as those exemplified by R of formula (a1-0) L a4 ~L a6is, independently of each other, preferably -O- or, *-O-(CH 2 ) k3 -CO-O-, where k3 is an integer from 1 to 4, more preferably -O- and, *-O-CH 2 -CO-O-, even more preferably an oxygen atom. L a7 is preferably -O- or *-O-L a8 -CO-O-, more preferably -O-, -O-CH 2 -CO-O- or -O-C 2 H 4 -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, even 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 from 0 to 2, more preferably 0 or 1. w1 is preferably an integer from 0 to 2, more preferably 0 or 1. In particular, formula (a3-4) is preferably formula (a3-4)’. TIFF2025087629000080.tif4051 (wherein R a24 and L a7 have the same meanings as described above.)
[0104] Examples of the structural unit (a3) include structural units derived from the monomers described in JP-A-2010-204646, the monomers described in JP-A-2000-122294, and the monomers described in JP-A-2012-41274. Examples of the structural unit (a3) include structural units represented by any of formula (a3-1-1), formula (a3-1-2), formula (a3-2-1), formula (a3-2-2), formula (a3-3-1), formula (a3-3-2), and formula (a3-4-1) to formula (a3-4-12), and in the said structural units, R in formula (a3-1) to formula (a3-4) a18 , R a19 , R a20 and R a24 The structural units in which the methyl groups corresponding to are replaced by hydrogen atoms are preferred. When the resin (A) 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 (A). Further, it is 70 mol% or less, preferably 65 mol% or less, more preferably 60 mol% or less, still more preferably 50 mol% or less, even more preferably 40 mol% or less, still even more preferably 30 mol% or less, still even more preferably 25 mol% or less, and still even more preferably 20 mol% or less. Specifically, it is 1 to 70 mol%, preferably 3 to 70 mol%, more preferably 3 to 65 mol%, still more preferably 5 to 65 mol%, even more preferably 5 to 60 mol%, and still even more preferably 10 to 60 mol%. In addition, the content ratio 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 resin (A). Further, it is preferably 60 mol% or less, more preferably 55 mol% or less, still more preferably 50 mol% or less, even more preferably 40 mol% or less, still even more preferably 30 mol% or less, even more preferably 25 mol% or less, and even more preferably 20 mol% or less. Specifically, 1 to 60 mol% is preferable, 3 to 60 mol% is more preferable, 3 to 55 mol% is still more preferable, 5 to 55 mol% is even more preferable, 5 to 50 mol% is even more preferably, and 10 to 50 mol% is still even more preferable.
[0105] <Structural unit (a4)> The structural unit represented by formula (a4) is shown below. TIFF2025087629000082.tif3255[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 represents a saturated hydrocarbon group having a halogen atom with 1 to 24 carbon atoms, and -CH 2 - contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.]
[0106] R 42 The saturated hydrocarbon group represented by is a linear or branched chain saturated hydrocarbon group, a monocyclic or polycyclic alicyclic saturated hydrocarbon group, and a group formed by combining these, etc. Examples of the chain saturated 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 saturated hydrocarbon group include monocyclic alicyclic saturated hydrocarbon groups which are monocyclic cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.; polycyclic alicyclic saturated hydrocarbon groups which are polycyclic cycloalkyl groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group and the following group (* represents the bonding site). Examples of the group formed by the combination of TIFF2025087629000083.tif10146 include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic saturated hydrocarbon groups, such as -alkanediyl group-alicyclic saturated hydrocarbon group, -alicyclic saturated hydrocarbon group-alkyl group, -alkanediyl group-alicyclic saturated hydrocarbon group-alkyl group, etc. 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, etc.; 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, a 2-methylbutane-1,4-diyl group, etc. The terminal of the branched alkanediyl group may be a methyl group. R 42 Examples of the halogen atom contained in the saturated hydrocarbon group included in R include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. R 42 Examples of the group in which -CH 2 - in the saturated hydrocarbon group contained in R is replaced by -O- or -CO- include a hydroxy group (-CH 2 - in the methyl group is replaced by -O-), a carboxy group (-CH 2 -CH 2 - in the ethyl group is replaced by -O-CO-), a carbonyl group (-CH 2 - in the methylene group is replaced by -CO-), an oxy group (-CH 2- is a group replaced by -O-), an alkoxy group (-CH at any position in the alkyl group 2 - is a group replaced by -O-), an alkoxycarbonyl group (-CH at any position in the alkyl group 2 -CH 2 - is a group replaced by -O-CO-), an alkylcarbonyl group (-CH at any position in the alkyl group 2 - is a group replaced by -CO-), an alkylcarbonyloxy group (-CH at any position in the alkyl group 2 -CH 2 - is a group replaced by -CO-O-), an alkanediyl-oxy group (-CH at any position in the alkanediyl group 2 - is a group replaced by -O-), an alkanediyl-oxycarbonyl group (-CH at any position in the alkanediyl group 2 -CH 2 - is a group replaced by -O-CO-), an alkanediylcarbonyl group (-CH at any position in the alkanediyl group 2 - is a group replaced by -CO-), an alkanediylcarbonyl-oxy group (-CH at any position in the alkanediyl group 2 -CH 2 - is a group replaced by -CO-O-), a cycloalkoxy group, a cycloalkylalkoxy group, a group formed by combining two or more of these groups, etc. may be mentioned. 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.
[0107] As the structural unit (a4), R 42 is preferably a saturated hydrocarbon group having a fluorine atom, R 42Examples of the structural unit (a4) which is a saturated 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. TIFF2025087629000084.tif4864[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.]
[0108] Examples of the alkanediyl group in 41 L 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 [description] 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, and an octane-1,8-diyl group having a fluorine atom; Examples of the branched alkanediyl group having a fluorine atom include 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, and 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 [description] include monocyclic cycloalkanediyl groups having a fluorine atom such as a cyclobutane-1,3-diyl group having a fluorine atom, a cyclopentane-1,3-diyl group having a fluorine atom, a cyclohexane-1,4-diyl group having a fluorine atom, a cyclohexene-3,6-diyl group having a fluorine atom, a cycloheptane-1,4-diyl group having a fluorine atom, and a cyclooctane-1,5-diyl group having a fluorine atom, Examples of the polycyclic cycloalkanediyl group having a fluorine atom include a norbornane-1,4-diyl group having a fluorine atom, a norbornane-2,5-diyl group having a fluorine atom, a 5-norbornene-2,3-diyl group having a fluorine atom, an adamantane-1,5-diyl group having a fluorine atom, and an adamantane-2,6-diyl group having a fluorine atom. L 42fThe number of fluorine atoms in the alkanediyl group and the cycloalkanediyl group having a fluorine atom is preferably 1 or more, and more preferably 2 or more. L 42f The alkanediyl group and the cycloalkanediyl group having a fluorine atom in are preferably a perfluoroalkanediyl group and a perfluorocycloalkanediyl group, respectively.
[0109] L 42f Examples of the perfluoroalkanediyl 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 perfluorocycloalkanediyl group in include a perfluorocyclohexanediyl group, a perfluorocyclopentanediyl group, a perfluorocycloheptanediyl group, a perfluoroadamantanediyl group, and the like.
[0110] L 41 is preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms, more preferably a single bond, a methylene group or an ethylene group, and even more preferably a single bond or a methylene group. L 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.
[0111] Examples of the structural unit (a4-1) include the structural units shown below and the structural units in which the methyl group corresponding to R in the following structural units is replaced by a hydrogen atom. 41 The structural unit represented by the formula (a4-2) is the structural unit shown below. TIFF2025087629000086.tif5574[In the formula (a4-2), R 41 represents a hydrogen atom or a methyl group. L 43f represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH 2 - contained in the saturated 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 -CH 2 - 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.]
[0112] Examples of the saturated hydrocarbon group in L 43f and R 43f include linear or branched chain saturated hydrocarbon groups, monocyclic or polycyclic alicyclic saturated hydrocarbon groups, and groups formed by combining these. Examples of the saturated hydrocarbon group in L 43f and R 43f are as follows for L 43f and R 43f As long as the upper limit of the total carbon number permits, R in formula (a4) 42 includes groups similar to the saturated hydrocarbon groups exemplified as the saturated hydrocarbon groups of 42 .
[0113] L 43f As the saturated hydrocarbon group of 43f , an alkanediyl group having 1 to 6 carbon atoms or a group represented by formula (L43f-1) is preferable. TIFF2025087629000087.tif14119 [In formula (L43f-1), s represents 0 or 1. L 45f and L 46f each independently represent a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may have a fluorine atom. L 47f represents a single bond or a divalent saturated 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 carbon number 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 .
[0114] As the divalent saturated hydrocarbon group represented by L 45f , L 46f and L 47f in the group represented by formula (L43f-1), there may be mentioned a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and a divalent saturated hydrocarbon group formed by combining an alkanediyl group and a divalent alicyclic saturated hydrocarbon group. Specifically, there may be mentioned a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group and the like. s is preferably 0.
[0115] 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. TIFF2025087629000088.tif47140
[0116] R 43f is preferably a saturated 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). TIFF2025087629000089.tif69102 [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 a saturated hydrocarbon group having 1 to 20 carbon atoms and having a fluorine atom. A 43f represents a divalent saturated hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom, and -CH 2 - contained in the saturated 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. R 43fB represents a saturated 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 the total number of carbon atoms of A 43f and R 43fBAt least one of them has at least one fluorine atom. R 43fA The saturated hydrocarbon group of is, as long as the upper limit of the number of carbon atoms permits, a saturated hydrocarbon group similar to the saturated hydrocarbon group exemplified by R 42 and includes saturated hydrocarbon groups similar to the saturated hydrocarbon groups exemplified by R. R 43fA is preferably an alkyl group having 1 to 13 carbon atoms and having a fluorine atom, a cycloalkyl group having 3 to 12 carbon atoms and having a fluorine atom, or a group combining them, *-(CF 2 ) 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 saturated hydrocarbon group of R 43fB are, as long as the upper limit of the number of carbon atoms permits, saturated hydrocarbon groups similar to the saturated hydrocarbon groups exemplified by R in formula (a4). 42 and includes saturated hydrocarbon groups similar to the saturated hydrocarbon groups exemplified by R. A 43f is preferably a divalent chain-like saturated hydrocarbon group which may have a fluorine atom, a divalent alicyclic saturated hydrocarbon group, or a group combining them, more preferably a divalent chain-like saturated hydrocarbon group having a fluorine atom, and even more preferably a fluorinated alkanediyl group having 1 to 6 carbon atoms. R 43fBThe saturated hydrocarbon group which may have a fluorine atom is preferably a chain saturated hydrocarbon group, an alicyclic saturated 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 trifluoromethyl group, difluoromethyl group, methyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, ethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, butyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, pentyl group, hexyl group, perfluorohexyl group, heptyl group, perfluoroheptyl group, octyl group, perfluorooctyl group and other alkyl fluoride groups, cyclopropylmethyl group, cyclopropyl group, cyclobutylmethyl group, cyclopentyl group, cyclohexyl group, perfluorocyclohexyl group, adamantyl group, adamantylmethyl group, adamantyldimethyl group, norbornyl group, norbornylmethyl group, perfluoroadamantyl group, perfluoroadamantylmethyl group and the like are more preferable.
[0117] In formula (a4-2B), *-A 43f -X 43 -R 43fB An example of the structure that the group represented by can take is the following structure (* is the bonding site with the carbonyl group). TIFF2025087629000090.tif14169
[0118] 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 are mentioned. TIFF2025087629000091.tif99167
[0119] Examples of the structural unit represented by formula (a4-2B) 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 represented by formula (a4-2B) is replaced by a hydrogen atom. 41 include structural units in which the methyl group corresponding to R in the structural unit represented by formula (a4-2B) is replaced by a hydrogen atom. TIFF2025087629000092.tif111163
[0120] Examples of the structural unit (a4) also include the structural unit represented by formula (a4-3). TIFF2025087629000093.tif5576[In formula (a4-3), R 41 represents a hydrogen atom or a methyl group. L 44f represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH 2 - contained in the saturated hydrocarbon group may be replaced by -O- or -CO-. R 44f represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH 2 - contained in the saturated 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.]
[0121] L 44f and R 44f Examples of the saturated hydrocarbon group in include linear or branched chain saturated hydrocarbon groups, monocyclic or polycyclic alicyclic saturated hydrocarbon groups, and groups formed by combining these. Examples of the saturated hydrocarbon group in L 44f and R 44f include, as long as the upper limit of the total number of carbon atoms of L 44f and R 44f allows, groups similar to the exemplified saturated hydrocarbon groups as the saturated hydrocarbon group of R 42 in formula (a4). L 44fis an alkanediyl group having 1 to 14 carbon atoms (the -CH contained in the alkanediyl group 2 - may be replaced by -O- or -CO-).), and it is preferably -(CH 2 ) j1 -, -(CH 2 ) j2 -O-(CH 2 ) j3 - or -(CH 2 ) j4 -CO-O-(CH 2 ) j5 - (where j1 to j5 each independently represent an integer from 1 to 6).) is more preferable. Further, an alkanediyl group having 1 to 4 carbon atoms (one -CH contained in the alkanediyl group 2 - may be replaced by -O-, and one -CH contained in the alkanediyl group 2 -CH 2 - may be replaced by -CO-O- or -O-CO-).) is even more preferable. R 44f is preferably a saturated hydrocarbon group having 1 to 10 carbon atoms with a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms with a fluorine atom, an alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms with a fluorine atom, or a group combining them, even more preferably an alkyl group having 1 to 10 carbon atoms with a fluorine atom, and still more preferably an alkyl group having 1 to 6 carbon atoms with a fluorine atom.
[0122] Examples of the structural unit represented by formula (a4-3) include structural units in which, in the following structural units and the following formulas, the methyl group corresponding to R 41 in structural unit (a4-3) is replaced by a hydrogen atom. TIFF2025087629000094.tif85165
[0123] TIFF2025087629000095.tif3686[In formula (a4-A), R 1represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X 11 represents a single bond or *-CO-O-. * represents the bonding site with the carbon atom to which R 1 is bonded. L 1 represents an aliphatic hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH 2 - in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-. R 2 represents a fluorinated alkyl group having 1 to 8 carbon atoms. R 3 represents a hydrogen atom or a fluorinated alkyl group having 1 to 6 carbon atoms, and the fluorinated alkyl group may be bonded to L 1 to form an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-. mi represents any integer from 1 to 4. When mi is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other.
[0124] R 1 Examples of the halogen atom and the alkyl group which may have a halogen atom in R a01 include those similar to R a4 and R a5 illustrated by. R 1 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.
[0125] L 1Examples of the aliphatic hydrocarbon group in [the compound of formula (I)] include a chain hydrocarbon group, a monocyclic or polycyclic (including a spiro ring, a condensed ring, a bridged ring, etc.) alicyclic hydrocarbon group, and a group formed by combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and a chain hydrocarbon group) may also be used. Examples of the chain hydrocarbon group include divalent to pentavalent chain hydrocarbon groups such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, and an alkanepentayl group. Examples of the alkanediyl group include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, a decane-1,10-diyl group, an undecane-1,11-diyl group, a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, and a heptadecane-1,17-diyl group, and branched alkanediyl groups such as an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. Examples also include a group in which one or more hydrogen atoms of the above-described group are replaced with a bonding site. The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, still more preferably 1 to 10, even more preferably 1 to 9, still even more preferably 1 to 8, still more preferably 1 to 6, still even more preferably 1 to 5, and particularly preferably 1 to 4.
[0126] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following alicyclic hydrocarbon groups. The bonding site can be at any position. TIFF2025087629000096.tif46164For example, divalent to pentavalent alicyclic hydrocarbon groups such as cycloalkanediyl groups, cycloalkanetriyl groups, cycloalkanetetrayl groups, cycloalkanepentayl groups, etc. can be mentioned. Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, etc. and Polycyclic alicyclic hydrocarbon groups such as spiro rings having a cycloalkanediyl group, norbornanediyl group or adamantanediyl group each spiro-bonded to a norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, decahydronaphthalenediyl group, bicyclo[3.3.0]octanediy group, spirocyclohexane-1,2'-cyclopentane-diyl group, spiroadamantane-2,3'-cyclopentane-diyl group, etc. can be mentioned. In addition, groups in which one or more hydrogen atoms of the above-mentioned groups are replaced at the bonding site, etc. can be mentioned. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12.
[0127] Examples of the group combined with two or more types include a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group. In the combination, two or more types of alicyclic hydrocarbon groups and chain hydrocarbon groups may be combined respectively. Also, any group may be bonded to X 11 No matter which group is bonded to X, it is okay. Examples of a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group include a group in which an alicyclic hydrocarbon group is bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-), a group in which a chain hydrocarbon group is bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-), a group in which an alicyclic hydrocarbon group and a chain hydrocarbon group are bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-), 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-), a group in which an alicyclic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group are bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-), a group in which a chain hydrocarbon group, an alicyclic hydrocarbon group, and a chain hydrocarbon group are bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-), and the like. * represents X 11 and represents the bonding site. Examples also include a group in which one or more hydrogen atoms of the above-described group are replaced with a bonding site.
[0128] L 1 The -CH in the aliphatic hydrocarbon group having 1 to 28 carbon atoms of 2 - may be replaced with -O-, -S-, -SO 2 - or -CO-. L 1 When the -CH in the aliphatic hydrocarbon group having 1 to 28 carbon atoms of 2 - is replaced with -O-, -S-, -SO 2 - or -CO-, the number of carbon atoms before replacement is defined as the number of carbon atoms of the aliphatic hydrocarbon group. The -CH in the aliphatic hydrocarbon group 2 - is -O-, -S-, -SO 2-Or as the group replaced by -CO-, there are 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 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, 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. Also, there are groups in which one or more hydrogen atoms of the above-described groups are replaced by a bonding site, and the like. -CH 2 - included in the alicyclic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO 2 - As the group replaced, those similar to the groups exemplified in this specification are included within the range where the upper limit of the number of carbon atoms permits. Also, -CH 2 - included in the alicyclic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO 2 - As the group replaced, those similar to the groups exemplified in this specification are included within the range where the upper limit of the number of carbon atoms permits.
[0129] 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 (-CH 2 - included in the alkyl group or the alicyclic hydrocarbon group may be replaced by -O- or -CO-). Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. The haloalkyl groups having 1 to 4 carbon atoms include fluoroalkyl groups having 1 to 4 carbon atoms, chloroalkyl groups having 1 to 4 carbon atoms, bromoalkyl groups having 1 to 4 carbon atoms, iodoalkyl groups having 1 to 4 carbon atoms, and the like. Examples of the haloalkyl group include perfluoroalkyl groups having 1 to 4 carbon atoms (such as trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, iodomethyl group, and the like. The number of carbon atoms of the haloalkyl group is preferably 1 to 3, more preferably 1 or 2. Examples of the alkyl group having 1 to 12 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, and the like. The number of carbon atoms of the alkyl group is preferably 1 to 9, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alicyclic hydrocarbon group having 3 to 18 carbon atoms include monocyclic cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, and polycyclic cycloalkyl groups such as decahydronaphthyl group, adamantyl group, 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, and still more preferably 3 to 10. Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include phenyl group, naphthyl group, biphenyl group, anthryl group, phenanthryl group, binaphthyl group, and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 14, more preferably 6 to 12, and still more preferably 6 to 10. -CH contained in the alkyl group 2- When replaced by -O- or -CO-, the total number of carbon atoms of the alkyl group is the number of carbon atoms before replacement. 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, etc. These replaced groups include those similar to the groups exemplified in this specification within the range permitted by the upper limit of the number of carbon atoms. The number of carbon atoms of the alkoxy group is preferably 1 to 9, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. The number of carbon atoms of the alkoxycarbonyl group is preferably 2 to 9, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyl group is preferably 2 to 10, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyloxy group and the alkoxycarbonyloxy group is each preferably 2 to 9, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. In addition, as the group in which -CH 2 - in the alicyclic hydrocarbon group is replaced by -O- or -CO-, those similar to the groups exemplified in this specification are included within the range permitted by the upper limit of the number of carbon atoms. L 1 Examples of the substituent that the aliphatic hydrocarbon group in may optionally 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 -CH 2 - in the alkyl group or the alicyclic hydrocarbon group may be replaced by -O- or -CO-). Fluorine atom, iodine atom, perfluoroalkyl group having 1 to 3 carbon atoms, or alkyl group having 1 to 4 carbon atoms (wherein -CH 2 - in the alkyl group may be replaced by -O- or -CO-) are more preferred, and fluorine atom, iodine atom, trifluoromethyl group, methyl group, hydroxy group, or methoxy group are even more preferred. L 1 is, when it does not form an alkyl fluoride group and an alicyclic hydrocarbon group of R 3 a chain hydrocarbon group having 1 to 12 carbon atoms which may have a substituent (in the chain hydrocarbon group, -CH 2 - 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, -CH 2 - 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 (in the chain hydrocarbon group, -CH 2 - may be replaced by -O- or -CO-, and in the alicyclic hydrocarbon group, -CH 2 - may be replaced by -O- or -CO-), preferably, a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent (in the chain hydrocarbon group, -CH 2 - 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 (in the chain hydrocarbon group, -CH 2 - may be replaced by -O- or -CO-), more preferably, a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent (in the chain hydrocarbon group, -CH 2 - 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 (in the chain hydrocarbon group, -CH 2 - may be replaced by -O- or -CO-), or a group formed by combining an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent, 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 (in the chain hydrocarbon group, -CH2 - may be replaced by -O- or -CO-. It is more preferable that it is).
[0130] R 2 Examples of the C1-C8 fluoroalkyl group in 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 number of carbon atoms 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 The C1-C6 fluoroalkyl group in, as long as the upper limit of the number of carbon atoms permits, the C1-C6 fluoroalkyl groups exemplified in the examples of the fluoroalkyl group of R 2 are similarly exemplified. R 2 is R 3When it is an alkyl fluoride group having 1 to 6 carbon atoms, it is preferably an alkyl fluoride group having 1 to 6 carbon atoms, more preferably an alkyl fluoride group having 1 to 3 carbon atoms, still more preferably a trifluoromethyl group, a perfluoroethyl group or a perfluoropropyl group, and even more preferably a trifluoromethyl group. R 2 When R 3 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, still more preferably an alkyl fluoride group having 3 to 5 carbon atoms. R 3 When R 1 is bonded to L 3 to form an alicyclic hydrocarbon group having 3 to 6 carbon atoms, examples of the group formed by the bonding of R 1 and L 2 include, for example, groups represented by the following formulas. Among 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 1A L 1 is a part of the hydrocarbon group of L 3 and represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. The number of carbon atoms of the alicyclic hydrocarbon group formed by the bonding of R 1 and L TIFF2025087629000097.tif25130R 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.
[0131] Examples of the structural unit (a4-A) include the following structural units and the like. TIFF2025087629000098.tif120167
[0132] TIFF2025087629000099.tif74168
[0133] In the above structural unit, R 1 A structural unit in which the methyl group corresponding to is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or an alkyl group other than a methyl group, and R 1 A structural unit in which the hydrogen atom corresponding to is replaced with a halogen atom, a haloalkyl group, or an alkyl group can also be cited as a specific example of the structural unit (a4-A).
[0134] When the resin (A) contains the structural unit (a4), its content is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and even more preferably 3 to 10 mol% based on all the structural units of the resin (A).
[0135] 〈Structural unit (a5)〉 Examples of the non-leaving hydrocarbon group contained in the structural unit (a5) include groups having a linear, branched, or cyclic hydrocarbon group. Among them, the structural unit (a5) is preferably a group having an alicyclic hydrocarbon group. Examples of the structural unit (a5) include, for example, the structural unit represented by the formula (a5-1). TIFF2025087629000100.tif3971[In the formula (a5-1), R 51 represents a hydrogen atom or a methyl group. R 52 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and the hydrogen atoms contained in the alicyclic hydrocarbon group may be substituted with aliphatic hydrocarbon groups having 1 to 8 carbon atoms. L 55 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH 2 - contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.]
[0136] R 52The alicyclic hydrocarbon group in [the compound] 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, etc. 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, etc. R 52 is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, and more preferably an adamantyl group, a norbornyl group, or a cyclohexyl group. L 55 Examples of the divalent saturated hydrocarbon group in [the compound] include a divalent chain saturated hydrocarbon group and a divalent alicyclic saturated hydrocarbon group, and preferably a divalent chain saturated hydrocarbon group. Examples of the divalent chain saturated hydrocarbon group include alkanediyl groups such as a methylene group, an ethylene group, a propanediyl group, a butanediyl group, and a pentanediyl group. The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic saturated hydrocarbon group include cycloalkanediyl groups such as a cyclopentanediyl group and a cyclohexanediyl group. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include an adamantanediyl group and a norbornanediyl group, etc.
[0137] L 55 Examples of the group in which -CH 2 - contained in the divalent saturated hydrocarbon group represented by L is replaced with -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. TIFF2025087629000101.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.] 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.
[0138] Examples of the group represented by the formula (L1-1) include the following divalent groups. Examples of the group represented by the formula (L1-2) include the following divalent groups. Examples of the group represented by the formula (L1-3) include the following divalent groups. Examples of the group represented by the formula (L1-4) include the following divalent groups. TIFF2025087629000105.tif13168L 55 is preferably a single bond or a group represented by the formula (L1-1).
[0139] Examples of the structural unit (a5-1) include the following structural units and structural units in which the methyl group corresponding to R in the structural unit (a5-1) is replaced by a hydrogen atom. 51 TIFF2025087629000106.tif111150 When the resin (A) contains the structural unit (a5), its content is preferably 1 to 30 mol%, more preferably 2 to 20 mol%, and still more preferably 3 to 15 mol% with respect to all the structural units of the resin (A).
[0140] 〈Structural unit (a6)〉 The structural unit (a6) is a structural unit having a -SO 2 - group, and preferably has a -SO 2 - group in the side chain. -SO 2 The structural unit having a - group may have a linear structure having a -SO 2 - group, or may have a branched structure having a -SO 2 - group, or may have a cyclic structure (monocyclic and polycyclic structures) having a -SO 2 - group. Preferably, it is a structural unit having a cyclic structure having a -SO 2 - group, and more preferably, it is a structural unit having a cyclic structure (sultone ring) containing -SO 2 -O-.
[0141] Examples of the sultone ring include rings represented by 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 -SO 2 -O- as an atomic group constituting the ring, and the formula (T1 -1) and formula (T 1 -2). Examples of the sultone ring include the ring represented by formula (T 1 -2). As an atomic group constituting the ring, like the ring represented by formula (T 2 -O-, may further contain a heteroatom. Examples of the heteroatom include an oxygen atom, a sulfur atom or a nitrogen atom, preferably an oxygen atom. TIFF2025087629000107.tif3077
[0142] The sultone ring may have a substituent. 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, etc. 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 an alkyl group having 1 to 6 carbon atoms, 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 perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group and a triiodomethyl group, preferably a trifluoromethyl group. 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, naphthyl group, anthryl group, p-methylphenyl group, p-tert-butylphenyl group, p-adamantylphenyl group, tolyl group, xylyl group, cumyl group, mesityl group, biphenyl group, phenanthryl group, 2,6-diethylphenyl group, and 2-methyl-6-ethylphenyl group. Examples of the aralkyl group include a benzyl group, phenethyl group, phenylpropyl group, naphthylmethyl group, and 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, more preferably a methoxycarbonyl group. Examples of the alkylcarbonyl group include an acetyl group, propionyl group, and butyryl group. From the viewpoint of easy production of the monomer leading to the structural unit (a6), a sultone ring having no substituent is preferred.
[0143] As the sultone ring, a ring represented by the following formula (T1') is preferred. TIFF2025087629000108.tif2665[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 Examples thereof include the same as the substituents of the sultone ring, and an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group is preferable. ma is preferably 0 or 1, more preferably 0.
[0144] Examples of the ring represented by formula (T1’) include the following rings. The bonding site may be at any position. Among them, the bonding site is preferably at the 1-position or 3-position. TIFF2025087629000109.tif44147-SO 2 The structural unit having a - group preferably further has a group derived from a polymerizable group. Examples of the polymerizable group include a vinyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, an acryloylthio group, a methacryloylthio group, and the like. Among them, the monomer that leads to the structural unit (a6) is preferably a monomer having an ethylenically unsaturated bond, more preferably a (meth)acrylic monomer.
[0145] The structural unit (a6) is preferably a structural unit represented by formula (a6-0). TIFF2025087629000110.tif4177[In formula (a6-0), R x represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom, or a halogen atom. A xx represents an oxygen atom, -N(R c )-, or a sulfur atom. A x represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH 2 - 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 41represents the same group as described above. ma represents an integer from 0 to 9. When ma is 2 or more, a plurality of Rs 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.
[0146] Examples of the halogen atom of R x include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkyl group of R x include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group, etc. Preferably, it is an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. Examples of the alkyl group having a halogen atom of R x include, for example, a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group, etc. R x is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. A x Examples of the divalent saturated hydrocarbon group of A include a linear alkanediyl group, a branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and a combination of two or more of these groups may also be used. Specifically, linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, heptadecane-1,17-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group and propane-2,2-diyl group; Branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group; Monocyclic divalent alicyclic saturated hydrocarbon groups which are cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group; Polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc. may be mentioned. A x The bonding position to the sultone ring of A can be any position, but the one at the 1-position is preferred.
[0147] Examples of the structural unit (a6-0) include the following structural units. TIFF2025087629000111.tif93150
[0148] Among them, the structural units represented by formula (a6-1), formula (a6-2), formula (a6-6), formula (a6-7), formula (a6-8) and formula (a6-12) are preferred, and the structural units represented by formula (a6-1), formula (a6-2), formula (a6-7) and (a6-8) are more preferred. When the resin (A) contains the structural unit (a6), its content is preferably 1 to 50 mol%, more preferably 2 to 40 mol%, and even more preferably 3 to 30 mol% based on all the structural units of the resin (A).
[0149] <Structural unit (a7)> The resin (A) etc. may further contain a structural unit that decomposes upon exposure to generate an acid (hereinafter sometimes referred to as "structural unit (a7)"). Specific examples of the structural unit (a7) include the structural units described in JP-A-2016-79235, and it is preferably a structural unit having a sulfonate group or a carboxylate group and an organic cation in the side chain or a structural unit having a sulfonio group and an organic anion in the side chain.
[0150] 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). TIFF2025087629000112.tif35107[In the formula (a7-A), R a7 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X a71 represents a single bond, *-O-*, *-CO-O-*, *-O-CO-O-*, *-CO-NR a71 -*, *-NR a71 -CO-O-*, *-O-CO-NR a71 -* or *-Ax-Ph-Ay-*. R a71 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ph represents a phenylene group which may have a substituent. Ax and Ay each independently represent one or more bond types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond. * and ** represent bonding sites, and * represents the bonding site with the carbon atom to which R a7 is bonded. L a71and L a72 each independently represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -. X a72 represents ***-CO-O-, ***-O-CO-, ***-O-CO-O-, ***-O-, where *** represents the bonding site with L a71 na7 represents any integer from 0 to 2. When na7 is 2, the groups within multiple parentheses may be the same as or different from each other. RA - represents a sulfonate anion or a carboxylate anion. ZA + represents an organic cation.]
[0151] R a7 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R are the same as those exemplified by R of formula (a1-0). a01 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. X a71 When X is a group represented by *-Ax-Ph-Ay-**, it is preferably a linking group represented by the following formula (X10). TIFF2025087629000113.tif3351[In formula (X10), Ax represents the bonding species that binds to the carbon atom to which R a7 is bonded, and represents one or more bonding species selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, a carbonate ester bond and an amide bond. Ay represents L a71 Represents a bonding type that combines, and represents one or more bonding types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, a carbonate bond, and an amide bond. Rx represents a halogen atom, a hydroxy group, a C1-C6 fluoroalkyl group, a C1-C18 alkyl group, or a C1-C6 alkoxy group. mx represents any integer from 0 to 4, and when mx is an integer of 2 or more, the plurality of Rx may be the same or different from each other. When either Ax or Ay is a single bond, it is preferable that the other is one or more selected from the group consisting of an ether bond, a thioether bond, an ester bond, a carbonate bond, and an amide bond. When either Ax or Ay is an amide bond, it is preferably a bond represented by -CO-NR a71 - represented by. The bonding position of Ay in the phenylene group is preferably the m-position or the p-position with respect to the bonding position of Ax, and more preferably the p-position. Among them, Rx is preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, or an ethyl group. mx is preferably 0, 1, or 2. X a71 As, for example, a single bond, the following formula (X 10 -1) to formula (X 10 -10) are mentioned. * represents the bonding site with the carbon atom to which -R a7 is bonded. ** represents the bonding site with L a71 is bonded. X 20 represents -O- or -NR a71 -. TIFF2025087629000114.tif43162 Formula (X 10 -1) to formula (X 10 -10) specific examples of the groups represented by are as follows. TIFF2025087629000115.tif87163 Among them, X a71 is a single bond and formula (X 10 -1’), formula (X 10 -3’) to formula (X10 It is preferably a group represented by any of them, a single bond or formula (X 10 -1’), formula (X 10 -4’), formula (X 10 -5’), formula (X 10 -6’) and formula (X 10 -9’), more preferably a single bond, a group represented by formula (X 10 -1’), a group represented by formula (X 10 -5’), a group represented by formula (X 10 -6’) or a group represented by formula (X 10 -9’).
[0152] L a71 Examples of the hydrocarbon group of include a group obtained by removing one hydrogen atom from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups, and bonding to X a71 and X a72 . Further, examples of the hydrocarbon group of L a72 include a group obtained by removing one hydrogen atom from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups, and bonding to X a72 and RA - . L a71 and L a72 Examples of the chain hydrocarbon group of include a group obtained by removing one hydrogen atom from an alkyl group or an alkenyl group. The alkyl group may be linear or branched, and specifically includes a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a heptadecyl group, etc. Examples of the alkenyl group include an ethenyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, an isooctenyl group, a nonenyl group, etc. The number of carbon atoms in the chain hydrocarbon group is preferably from 1 to 20, more preferably from 1 to 18, and even more preferably from 1 to 10. L a71 and L a72 Examples of the alicyclic hydrocarbon group of L and L include a group obtained by removing one hydrogen atom from a monocyclic or polycyclic cycloalkyl group. Examples of the monocyclic cycloalkyl group include a cyclobutyl group, a cycloheptyl group, a cyclohexyl group, a cyclopentyl group, a cyclooctyl group, and the like. L a71 and L a72 Examples of the polycyclic cycloalkyl group of L and L include a cycloalkyl group having a crosslinked structure, a cycloalkyl group in which two or more rings are condensed, or a cycloalkyl group in which two rings are spiro-bonded. Examples of the cycloalkyl group having a crosslinked structure include a norbornyl group, an adamantyl group, and the like. Examples of the cycloalkyl group in which two or more rings are condensed include a bicyclo[4,4,0]decane group, a steroid group (steroid skeleton), and the like. Examples of the cycloalkyl group in which two rings are spiro-bonded include a spirocyclic cycloalkyl group in which one cycloalkyl group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group and a cycloalkyl group having 5 to 8 carbon atoms are spiro-bonded. Further, a double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group. More specifically, the alicyclic hydrocarbon group represented by the following formula can be mentioned. TIFF2025087629000116.tif28158 When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably from 3 to 18, more preferably from 3 to 12, and even more preferably from 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably from 6 to 18, more preferably from 7 to 12. L a71 and L a72Examples of the aromatic hydrocarbon group include a group obtained by removing one hydrogen atom from an aryl group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a fluorenyl group, and the like. The number of carbon atoms in the aromatic hydrocarbon group is preferably 5 to 14, more preferably 6 to 14, and even more preferably 6 to 10. L a71 and L a72 When the -CH 2 - contained in the hydrocarbon group of 2 and L is replaced by -O-, -CO-, -S- or -SO L a71 and L a72 among the hydrocarbon groups of 2 When the -CH 2 - contained in the chain hydrocarbon group is replaced by -O-, -CO-, -S- or -SO L a71 and L a72 among the hydrocarbon groups of 2 When the -CH 2 - contained in the alicyclic hydrocarbon group is replaced by -O-, -CO-, -S- or -SO TIFF2025087629000117.tif46146L a71 and L a72 among the hydrocarbon groups of2 - may be replaced by -O- or -S-, -CH 2 - As the group in which - is replaced by -O- or -S-, groups derived from a furan ring or a thiophene ring, etc. may be mentioned respectively. L a71 and L a72 As the group combining two or more of the chain hydrocarbon group, alicyclic hydrocarbon group and aromatic hydrocarbon group of L and L, the group combining the above chain hydrocarbon group and the above alicyclic hydrocarbon group, the group combining the above chain hydrocarbon group and the above aromatic hydrocarbon group, the group combining the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group, and the group combining the above chain hydrocarbon group, the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group may be mentioned. As the group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, it may be a condensed ring. L a71 and L a72 Examples of the substituent that the hydrocarbon group of L and L 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, an iodine atom, etc. L a71 and L a72 When L and L 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, L a71 and L a72 By replacing -CH 2 - in the chain hydrocarbon group contained in the hydrocarbon group of L and L with -O-, -CO-, -S- or -SO 2 -, the hydrocarbon group of L a71 and L a72 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, etc. na7 is preferably 0 or 1. ZA in formula (a7 - A) + is the same as those of the cations in the salts represented by formula (B1), etc.
[0153] In formula (a7-A), L a71 and L a72 are saturated hydrocarbon groups, in the following formula (a7-B), A b7 may contain a group similar to the group exemplified as the divalent linking group of. Examples of the structural unit represented by formula (a7-A) include the structural unit represented by formula (a7-A1). TIFF2025087629000118.tif30138 [In formula (a7-A1), R a7 、X a71 、L a71 、X a72 、na7, RA - and ZA + have the same meanings as described above. z7 represents any integer from 0 to 6. Q a7 、Q b7 、R z71 and R z72 each independently represent a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. When z7 is 2 or more, a plurality of R z71 and R z72 may be the same as or different from each other.] Q a7 、Q b7 、R z71 and R z72 Examples of the perfluoroalkyl group having 1 to 6 carbon atoms or the alkyl group having 1 to 6 carbon atoms in include groups similar to the groups exemplified by R a7 .
[0154] 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 are replaced with 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 WO 2012 / 050015. ZA + represents an organic cation. TIFF2025087629000119.tif130158
[0155] TIFF2025087629000120.tif244162
[0156] 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). TIFF2025087629000121.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 include the same as those described above. Ab7 Examples of the divalent linking group represented by [formula] include divalent saturated hydrocarbon groups having 1 to 18 carbon atoms, and -CH contained in the divalent saturated hydrocarbon group 2 - may be replaced by -O-, -S- or -CO-. Examples of the divalent saturated hydrocarbon group include divalent chain-like saturated hydrocarbon groups such as linear or branched alkanediyl groups, and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups, and combinations thereof may also be used. Specifically, linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group; branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group; 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, which are divalent monocyclic alicyclic saturated hydrocarbon groups; 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, which are divalent polycyclic alicyclic saturated hydrocarbon groups, etc. may be mentioned. -CH contained in the saturated hydrocarbon group 2 Examples of those in which - is replaced by -O-, -S- or -CO- include the following divalent groups. However, the number of carbon atoms before - is replaced by -O-, -S- or -CO- in the saturated hydrocarbon group is each 17 or less. In the following formula, * and ** represent bonding sites, and * represents the bonding site with R 2 - and ** represents the bonding site with R b71 and the bonding site with R. TIFF2025087629000122.tif123161[wherein, X 3represents a divalent saturated hydrocarbon group having 1 to 16 carbon atoms. X 4 represents a divalent saturated hydrocarbon group having 1 to 15 carbon atoms. X 5 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms. X 6 represents a divalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 7 represents a trivalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 8 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.
[0157] Examples of the structural unit containing the cation in formula (a7-B) include the structural unit represented below and a structural unit in which the group corresponding to the methyl group of R a7 is replaced with a hydrogen atom, a halogen atom (e.g., fluorine atom), or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (e.g., trifluoromethyl group, etc.). JPEG2025087629000123.jpg72163
[0158] A - Examples of the organic anion represented by A include sulfonate anions, sulfonylimide anions, sulfonylmethide anions, and carboxylate anions. A - The organic anion represented by A is preferably a sulfonate anion, and more preferably the same as the anion exemplified by the acid generator (B). Examples of the sulfonylimide anion, sulfonylmethide anion, and carboxylate anion include the same as the anion exemplified by the acid generator (B).
[0159] Examples of the structural unit represented by formula (a7-B) include the structural unit represented below. JPEG2025087629000124.jpg95157
[0160] When the resin (A) contains the structural unit (a7), the structural unit (a7) may be contained alone or in combination of two or more. The content of the total structural unit (a7) is preferably 1 to 30 mol%, more preferably 2 to 25 mol%, and still more preferably 3 to 20 mol% based on all the structural units of the resin (A).
[0161] The resin (A) is preferably a resin composed of the structural unit (I), the structural unit (II), the structural unit (a1), and the structural unit (s). The structural unit (a1) is preferably at least one selected from the group consisting of the structural unit (a1-0), the structural unit (a1-1), and the structural unit (a1-2) (preferably the structural unit having a cyclohexyl group or a cyclopentyl group), and more preferably at least one selected from the group consisting of the structural unit (a1-1) and the structural unit (a1-2). The structural unit (s) is preferably at least one selected from the group consisting of the structural unit (a2) and the structural unit (a3). The structural unit (a2) is preferably the structural unit (a2-C) or the structural unit (a2-A). The structural unit (a3) is preferably at least one selected from the group consisting of the structural unit represented by the formula (a3-1), the structural unit represented by the formula (a3-2), and the structural unit represented by the formula (a3-4).
[0162] Each structural unit constituting the resin (A) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using monomers that lead to these structural units. The content of each structural unit of the resin (A) can be adjusted by the amount of monomers used in the polymerization. The weight average molecular weight of the resin (A) is preferably 2,000 or more (more preferably 2,500 or more, still more preferably 3,000 or more), 50,000 or less (more preferably 30,000 or less, still more preferably 15,000 or less), but may contain oligomers having a weight average molecular weight smaller than this. In this specification, the weight average molecular weight is a value determined by gel permeation chromatography under the conditions described in the examples.
[0163] <Resins other than resin (A)> The resist composition of the present invention may contain a resin other than resin (A). The resin other than resin (A) is a resin that does not contain any of structural unit (I), structural unit (II), and structural unit (a1). For example, a resin composed only of structural unit (s), a resin composed of structural unit (a1), structural unit (a2), structural unit (a3), and / or structural units derived from other known monomers, a resin composed of structural unit (I), structural unit (a1), structural unit (a2), structural unit (a3), and / or structural units derived from other known monomers, and a resin composed of structural unit (II), structural unit (a1), structural unit (a2), structural unit (a3), and / or structural units derived from other known monomers can be mentioned.
[0164] In addition, as other resins, resins containing structural unit (a4) or structural unit (a5) (however, not containing any of structural unit (I), structural unit (II), and structural unit (a1); hereinafter sometimes referred to as "resin (X)") and the like can be mentioned. As resin (X), among others, a resin containing structural unit (a4) is preferable. When the resin (X) contains the structural unit (a4), in the resin (X), the content of the structural unit (a4) is 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and still more preferably 45 mol% or more, based on the total of all the structural units of the resin (X). Also, it is 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, it is 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, still more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. When the resin (X) contains the structural unit (a5), the content of the structural unit (a5) is 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and still more preferably 45 mol% or more, based on the total of all the structural units of the resin (X). Also, it is 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, it is 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, still more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. Further, when the resin (X) contains the structural unit (a4) and the structural unit (a5), the total content of the structural unit (a4) and the structural unit (a5) is 40 mol% or more, preferably 60 mol% or more, more preferably 70 mol% or more, and still more preferably 80 mol% or more, based on the total of all the structural units of the resin (X). 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%, and still more preferably 80 to 100 mol%. Examples of the structural unit that the resin (X) may further have include the structural unit (a2), the structural unit (a3), and the structural unit derived from other known monomers. Among them, the resin (X) is preferably a resin composed of only the structural unit (a4) and / or the structural unit (a5). Each structural unit constituting the resin (X) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using monomers that induce these structural units. The content of each structural unit of the resin (X) can be adjusted by the amount of monomers used in the polymerization. Each structural unit constituting the resin (X) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using monomers that induce these structural units. The content of each structural unit of the resin (X) can be adjusted by the amount of monomers used in the polymerization. The weight average molecular weight of the resin (X) is preferably 6,000 or more (more preferably 7,000 or more) and 80,000 or less (more preferably 60,000 or less), but may contain oligomers having a weight average molecular weight smaller than this. The measuring means for the weight average molecular weight of the resin (X) is the same as that of the resin (A).
[0165] When the resist composition of the present invention contains the resin (X), its content is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, still more preferably 1 to 40 parts by mass, even more preferably 1 to 30 parts by mass, and even more preferably 1 to 8 parts by mass with respect to 100 parts by mass of the resin (A).
[0166] The content of the resin (A) in the resist composition is preferably 20% by mass or more and 100% by mass or less, more preferably 50% by mass or more and 99% by mass or less, based on the solid content of the resist composition. When the resist composition contains a resin other than the resin (A), the total content of the resin (A) and the resin other than the resin (A) is preferably 60% by mass or more and 100% by mass or less, more preferably 70% by mass or more and 99% by mass or less, still more preferably 80% by mass or more and 99% by mass or less, and even more preferably 90% by mass or more and 99% by mass or less, based on the solid content of the resist composition. The solid content of the resist composition and the content of the resin relative to this can be measured by known analytical means such as liquid chromatography or gas chromatography.
[0167] <Acid generator (B)> 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, benzenesulfonyl anion, sulfonylimide anion, sulfonylmethide anion, and carboxylic acid anion, etc. Further, the acid generator (B) may be a structural unit having an acid generation function, for example, a resin having the above-mentioned structural unit (a7).
[0168] 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. Also, compounds produced by known methods may be used. The acid generator (B) may be used alone as only one kind, or in combination of two or more kinds. Further, 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 serving as the acid-labile group, and the acid-labile group preferably contains the above-mentioned group (1) or group (2).
[0169] As a preferred form of the acid generator (B), a salt represented by the formula (B1) (hereinafter sometimes referred to as "salt (B1)" or "acid generator (B1)") or a salt represented by the formula (B2) (hereinafter sometimes referred to as "salt (B2)" or "acid generator (B2)") can be mentioned. TIFF2025087629000125.tif1492[In the formula (B1), all the symbols represent the same meaning as described above.] L b1 As the (nb1 + 1)-valent hydrocarbon group of L, from a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, a monovalent aromatic hydrocarbon group, and a monovalent group combining two or more of these groups, nb1 hydrogen atoms are removed, and a group bonding to one or more L b2 can be mentioned. The number of carbon atoms of the hydrocarbon group is preferably 1 to 48, more preferably 1 to 42, still more preferably 1 to 36, even more preferably 1 to 30, and even still more preferably 1 to 24. As the chain hydrocarbon group, a group obtained by removing nb1 hydrogen atoms 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, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, iso-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, heptadecyl group, 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 24, still more preferably 1 to 20, even more preferably 1 to 18, even still more preferably 1 to 12, and even 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 a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. 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 adamantyl group. Examples of the cycloalkyl group in which two or more rings are condensed include a bicyclo[4,4,0]decane group and a steroid group (steroid skeleton). Examples of the cycloalkyl group in which two rings are spiro-bonded include a spirocycloalkyl group in which one or more cycloalkyl groups selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group and a cycloalkyl group having 5 to 8 carbon atoms are spiro-bonded. A double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group. More specifically, examples of the alicyclic hydrocarbon group include those represented by the following formula. TIFF2025087629000126.tif26168 When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 20, still more preferably 3 to 18, even more preferably 3 to 12, even still more preferably 3 to 10, and even more preferably 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 6 to 24, more preferably 6 to 20, still more preferably 6 to 18, even more preferably 6 to 12, and even still more preferably 7 to 12. Examples of the aromatic hydrocarbon group include a group obtained by removing nb1 hydrogen atoms from an aryl group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a fluorenyl group, etc. More specifically, examples of the aromatic hydrocarbon group include those represented by the following formulae. TIFF2025087629000127.tif1285 The number of carbon atoms of the aromatic hydrocarbon group is preferably 4 to 24, more preferably 4 to 20, still more preferably 4 to 18, even more preferably 5 to 14, even still more preferably 5 to 10, and even more preferably 6 to 10. L b1 In the hydrocarbon group of, -CH 2 - is replaced by -O-, -CO-, -S- or -SO 2 - When it is replaced, the number of carbon atoms before replacement is taken as the number of carbon atoms of the hydrocarbon group. L b1 Among the hydrocarbon groups of, as the group in which -CH 2 - in the chain hydrocarbon group is replaced by -O-, -CO-, -S- or -SO 2 - Examples include a hydroxy group (the group in which -CH 2 - in the methyl group is replaced by -O-), a carboxy group (the group in which -CH 2 -CH 2 - in the ethyl group is replaced by -O-CO-), a carbonyl group (the group in which -CH 2 - in the methylene group is replaced by -CO-), an oxy group (the group in which -CH 2 - in the methylene group is replaced by -O-), an alkoxy group (the group in which -CH 2 - at any position in the alkyl group is replaced by -O-), an alkoxycarbonyl group (the group in which -CH 2 -CH 2 - at any position in the alkyl group is replaced by -O-CO-), an alkylcarbonyl group (the group in which -CH 2 - at any position in the alkyl group is replaced by -CO-), an alkylcarbonyloxy group (the group in which -CH 2 -CH2 - being a group replaced by -CO-O-, an alkanediyl-oxy group (wherein any -CH at a position included in the alkanediyl group 2 - being a group replaced by -O-, an alkanediyl-oxycarbonyl group (wherein any -CH at a position included in the alkanediyl group 2 -CH 2 - being a group replaced by -O-CO-, an alkanediyl-carbonyl group (wherein any -CH at a position included in the alkanediyl group 2 - being a group replaced by -CO-, an alkanediyl-carbonyl-oxy group (wherein any -CH at a position included in the alkanediyl group 2 -CH 2 - being a group replaced by -CO-O-), etc. may be mentioned. These replaced groups include, within the range where the upper limit of the number of carbon atoms permits, the same groups as those exemplified in this specification. L b1 Among the hydrocarbon groups of, the -CH included in the alicyclic hydrocarbon group 2 - being replaced by -O-, -CO-, -S- or -SO 2 - groups include groups containing structures such as cyclic ethers, cyclic ketones, cyclic esters (lactones), cyclic thioethers, cyclic acetals, cyclic sulfonic acid esters ( sultones), etc. Specifically, alicyclic hydrocarbon groups represented by the following formulas may be mentioned. The bonding positions of the alicyclic hydrocarbon groups mentioned in the following formulas can be at any position. TIFF2025087629000128.tif48165L b1 Among the hydrocarbon groups of, the -CH included in the aromatic hydrocarbon group 2 - may be replaced by -O- or -S-, and as the group where -CH 2 - is replaced by -O- or -S-, groups derived from a furan ring or a thiophene ring, etc. may be mentioned respectively. Specifically, aromatic hydrocarbon groups represented by the following formulas may be mentioned. TIFF2025087629000129.tif1326Groups containing a combination of an alicyclic hydrocarbon group and an aromatic hydrocarbon group, the -CH 2 - being -O-, -S-, -CO- or -SO 2Examples of the group replaced by "-" include the same groups as those exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms. Examples of the group formed by combining two or more of an acyclic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group include a group formed by combining the above acyclic hydrocarbon group and the above alicyclic hydrocarbon group, a group formed by combining the above acyclic hydrocarbon group and the above aromatic hydrocarbon group, a group formed by combining the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group, and a group formed by combining the above acyclic hydrocarbon group, the above alicyclic hydrocarbon group, and the above aromatic hydrocarbon group. The group formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group may be a condensed ring. L b2 Examples of the divalent hydrocarbon group of include a divalent acyclic hydrocarbon group, a divalent alicyclic hydrocarbon group, a divalent aromatic hydrocarbon group, and a group formed by combining two or more of these groups, and a group formed by removing one hydrogen atom from a monovalent hydrocarbon group and bonding to Y b1 is mentioned. L b2 Examples of the divalent acyclic hydrocarbon group, divalent alicyclic hydrocarbon group, divalent aromatic hydrocarbon group, and divalent group formed by combining two or more of these groups of L b1 are groups formed by removing one hydrogen atom from the monovalent acyclic hydrocarbon group, monovalent alicyclic hydrocarbon group, monovalent aromatic hydrocarbon group, and monovalent group formed by combining two or more of these groups exemplified by L L b1 and L b2 Examples of the substituent that the hydrocarbon group of and L L b1 and L b2 may have include a halogen atom, a cyano group, a nitro group, etc. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. b1 and L b2 When the hydrocarbon group of and L 2 is a group formed by combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group and an acyclic hydrocarbon group, the acyclic hydrocarbon group may be substantially regarded as a substituent that the alicyclic hydrocarbon group or the aromatic hydrocarbon group has. Also, the -CH2 - is replaced by L b1 and L b2 The hydrocarbon groups of and may substantially have substituents such as hydroxy group, carboxy group, carbonyloxy group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, thiol group, alkylthio group, alkylsulfonyl group, etc. Y b1 Examples of the cyclic hydrocarbon group of include alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining alicyclic hydrocarbon groups and aromatic hydrocarbon groups. Y b1 The alicyclic hydrocarbon group and aromatic hydrocarbon group of are respectively the same as the alicyclic hydrocarbon group and aromatic hydrocarbon group exemplified by L b1 and when having no substituent, they may be monovalent alicyclic hydrocarbon groups and aromatic hydrocarbon groups. Y b1 Examples of the substituent that the methyl group of may have include halogen atom, cyano group, hydroxy group, nitro group, etc. Y b1 Examples of the substituent that the cyclic hydrocarbon group of may have include halogen atom, cyano group, nitro group, or a hydrocarbon group having 1 to 18 carbon atoms which may have a halogen atom, cyano group or nitro group. The -CH 2 - in may be replaced by -O-, -S-, -CO- or -SO 2 -. Y b1 The carbon number of the hydrocarbon group that the cyclic hydrocarbon group of may have is not included in the carbon number of the cyclic hydrocarbon group of Y b1 Y b1 Examples of the hydrocarbon group having 1 to 18 carbon atoms that the cyclic hydrocarbon group of may have as a substituent include chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining these groups. Examples of chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining two or more of these groups include, within the range permitted by the upper limit of the carbon number, L b1Examples of the same groups as the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and groups formed by combining two or more of these groups exemplified above. Also, Y b1 The -CH 2 - in the hydrocarbon group having 1 to 18 carbon atoms in which the cyclic hydrocarbon group of Y 2 may be included as a substituent is replaced by -O-, -S-, -CO- or -SO b1 - Examples of the group are, within the range allowed by the upper limit of the number of carbon atoms, the -CH 2 - in the hydrocarbon group of L 2 is replaced by -O-, -S-, -CO- or -SO b1 - Examples of the same groups as the groups exemplified above. Also, Y b1 The hydrocarbon group having 1 to 18 carbon atoms in which the cyclic hydrocarbon group of Y may be included as a substituent may constitute a protecting group or a leaving group generally used in the art (for example, an acid-labile group or a base-labile group such as the above-mentioned group (1) or group (2)). Here, the "base-labile group" means a group having a leaving group, and when contacted with a base, the leaving group is eliminated to form a hydrophilic group (for example, a hydroxy group or a carboxy group). The anion of the salt represented by the formula (B1) is preferably an anion represented by the following formula (B1-A1) (hereinafter sometimes referred to as "anion (B1-A1)") or an anion represented by the formula (B1-A2) (hereinafter sometimes referred to as "anion (B1-A2)"). TIFF2025087629000130.tif31125 [In the formula (B1-A1), L b2 and Y b1 have the same meanings as in the formula (B1). Q b1 、Q b2 、Q b3 and Q b4 each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. z1 represents any integer from 0 to 6. When z1 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. X 1represents -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 -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -. nb2 represents any integer from 1 to 3. When nb2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. Q b1 、Q b2 、Q b3 and Q b4 Examples of the alkyl group of Q Q b1 、Q b2 、Q b3 and Q b4 Examples of the perfluoroalkyl group of Q Q b1 and Q b2 are preferably included in at least one of Q b1 and Q b2 and more preferably a fluorine atom or a perfluoroalkyl group, still more preferably a fluorine atom or a trifluoromethyl group, and even more preferably both are fluorine atoms. Q b3 and Q b4 are each independently preferably a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, and Q b3 is preferably a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, and Q b4is preferably a hydrogen atom or a fluorine atom. z1 is preferably any integer from 0 to 3, and preferably 0, 1, or 2. X 1 is preferably -O-CO- or -CO-O-.
[0170] L b3 As the hydrocarbon group in, within the range allowed by the upper limit of the number of carbon atoms, the L in the formula (B1) b1 includes the same hydrocarbon groups as those exemplified in. In the formula (B1-A1), L b3 is a single bond, an optionally substituted chain hydrocarbon group having 1 to 12 carbon atoms (the -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), an optionally substituted alicyclic hydrocarbon group having 3 to 18 carbon atoms (the -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms (the -CH 2 - in the aromatic hydrocarbon group may be replaced by -O- or -S-), or a group formed by combining two or more of these groups, and is 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). In addition, when -CH 2 - in the chain hydrocarbon group is replaced by -O- or -CO-, the number of -CH 2 - in the chain hydrocarbon group replaced by -O- or -CO- is preferably 1 to 4, and one -CH 2 -CH 2 - in the chain hydrocarbon group is preferably replaced by -O-CO- or -CO-O-, or one -CH 2 -CH 2 -CH 2 - in the chain hydrocarbon group is preferably replaced by -O-CO-O-. TIFF2025087629000131.tif1682 [In the formula (Lb3-1), nb2 represents the same meaning as the formula (B1 - A1). L b31 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms, and -CH 2 - contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent. W b3 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon a...
Claims
1. A resist composition comprising a resin that includes a structural unit represented by formula (I), a structural unit having a group represented by formula (II-x), and a structural unit having an acid labile group. [In formula (I), X 0 represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -CO- or -SO 2 It may be replaced with -. L 10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -SO 2 It may be replaced by --or --CO--. R 10 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. X 10 represents a single bond, *-O-**, *-CO-O-**, *-O-CO-O-**, *-CO-NR 3 -**, *-NR 3 -CO-O-**, *-O-CO-NR 3 -** or *-Ax-Ph-Ay-**. R 3 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 binding sites, * represents R 10 represents the bonding site with the carbon atom to which it is bonded. Z1 + represents an organic cation. [In formula (II-x), Ring W 1 represents a heterocycle having 2 to 36 carbon atoms, a hydrogen atom contained in the heterocycle may be substituted with a halogen atom or a hydrocarbon group having 1 to 24 carbon atoms, and —CH 2 - is -O-, -S-, -CO- or -NR c It may be replaced by -. R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. * indicates a binding site.
2. X 10 is a single bond or a group represented by the formula (X 10 -1) ~Formula (X 10 2. The resist composition according to claim 1, wherein the aryl group is a group represented by any one of the following formulas: [Formula (X 10 -1) ~ type (X 10 -10) *, ** are binding sites, * is R 10 represents the bonding site with the carbon atom to which it is bonded. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4. X 20 is -O- or -NR 3 Represents -. R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
3. L 10 is a single bond, a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (provided that the —CH 2 - may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (provided that the -CH 2 - is -O-, -S-, -CO- or -SO 2 -) 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 24 carbon atoms which may have a substituent (with the proviso that -CH 2 - may be replaced by -O- or -CO-, and -CH contained in the cyclic hydrocarbon group 2 - is -O-, -S-, -SO 2 2. The resist composition according to claim 1, wherein:
4. X 0 is a single bond, an open chain hydrocarbon group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, a group in which an alicyclic hydrocarbon group having 3 to 36 carbon atoms and an open chain hydrocarbon group having 1 to 18 carbon atoms are combined, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group in which an aromatic hydrocarbon group having 6 to 36 carbon atoms and an open chain hydrocarbon group having 1 to 18 carbon atoms are combined, The —CH group contained in the chain hydrocarbon group and the alicyclic hydrocarbon group 2 - is -O-, -S-, -CO- or -SO 2 2. The resist composition according to claim 1, wherein the chain hydrocarbon group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group each optionally have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group.
5. 2. The resist composition according to claim 1, wherein the structural unit having a group represented by formula (II-x) is a structural unit represented by formula (IIA). [In formula (IIA), Ring W 1 has the same meaning as in formula (II-x). 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 X is a single bond, -A X1 -* or -CO-O-A X1 -* (* represents the bonding site with the carbonyl group). A X1 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the —CH 2 - is -O-, -CO- or -N(R d ) - may be replaced. R d represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
6. The resist composition according to claim 1, wherein the structural unit having an acid labile group includes at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), a structural unit represented by formula (a1-2), a structural unit represented by formula (a1-4), a structural unit represented by formula (a1-5), and a structural unit represented by formula (a1-6). [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or *-O-(CH 2 ) k1 represents --CO--O--, k1 represents an integer of 1 to 7, and * represents the bonding site with --CO--. R a01 , R a4 and R a5 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a combination thereof, and the alkyl group, alicyclic hydrocarbon group and aromatic hydrocarbon group may contain a halogen atom. R a6 and R a7 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these, and the alkyl group, alkenyl group, alicyclic hydrocarbon group and aromatic hydrocarbon group may have a halogen atom. m1 represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1' represents an integer of 0 to 3. [In formula (a1-4), R a1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a17 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a11 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and the —CH 2 - is -O-, -CO- or -NR a18 May be replaced with -. R a18 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a1 represents a single bond or a carbonyl group. R a34 and R a35 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a36 represents a hydrocarbon group having 1 to 20 carbon atoms, or R a35 and R a36 are bonded to each other to form a divalent hydrocarbon group having 2 to 20 carbon atoms together with the -C-O- to which they are bonded, and the hydrocarbon group and the -CH 2 - may be replaced by -O- or -S-. na1 represents an integer of 1 to 5, and when na1 is 2 or more, the groups in the parentheses may be the same or different. na11 represents an integer of 0 to 4, and when na11 is 2 or more, a plurality of R a17 may be the same or different from each other. mc represents an integer of 0 to 2. [In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. Z a1 is a single bond or *-(CH 2 ) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, * represents L 51 represents the binding site with L 51 , L 52 , L 53 and L 54 each independently represents --O-- or --S--. s1 represents an integer of 1 to 3. s1′ represents an integer of 0 to 3. [In formula (a1-6), R a61 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a62 , R a63 and R a64 each independently represents an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, or R a62 and R a63 are bonded to each other to form, together with the carbon atoms to which they are attached, a ring having 3 to 20 carbon atoms. X a61 is a single bond, -CO-O-* or -CO-NR a65 - represents *, * represents a bonding site with Ar, R a65 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 is a single bond, *-O-L a61 - or *-CO-OL a62 -, * represents a bonding site with Ar, L a61 and L a62 each independently represents an alkanediyl group having 1 to 4 carbon atoms. Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.
7. 2. The resist composition according to claim 1, wherein the resin further comprises a structural unit represented by formula (a2-A). [In formula (a2-A), R a2 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a27 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and the —CH 2 - is -O-, -CO- or -NR a28 May be replaced with -. R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a2 represents a single bond or a carbonyl group. nA2 represents an integer of 1 to 5, and when nA2 is 2 or more, the groups in the parentheses may be the same or different. na21 represents an integer of 0 to 4, and when na21 is 2 or more, a plurality of R a27 may be the same or different from each other. mc represents an integer of 0 to 2.
8. Further containing an acid generator, 2. The resist composition according to claim 1, wherein the acid generator comprises a salt represented by formula (B1). [In formula (B1), L b1 represents a single bond or a (nb1+1)-valent hydrocarbon group which may have a substituent, and —CH 2 - is -O-, -S-, -CO- or -SO 2 It may be replaced with -. L b2 represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the —CH 2 - is -O-, -S-, -CO- or -SO 2 It may be replaced by -. Y b1 represents a methyl group which may have a substituent or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -SO 2 It may be replaced by --or --CO--. nb1 represents an integer of 1 to 6. When nb1 is 2 or more, the groups in the parentheses may be the same or different. Z + represents an organic cation.
9. (1) A step of applying a resist composition according to any one of claims 1 to 8 onto a substrate; (2) A step of drying the applied resist composition to form a composition layer; (3) exposing the composition layer to light; (4) heating the composition layer after exposure; and (5) developing the composition layer after heating; A method for producing a resist pattern comprising the steps of:
Citation Information
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