Carboxylic acid generator, carboxylate, resist composition, and method for producing resist pattern
The carboxylic acid generator with a carboxylic acid salt of formula (I) enhances pattern stability in resist compositions, addressing poor pattern collapse resistance in existing technologies.
Patent Information
- Application Number
- JP2025128745
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-08-01
- Filing Date
- 2025-07-31
- Publication Date
- 2026-02-16
AI Technical Summary
Existing resist compositions form patterns with poor pattern collapse resistance (PCM), leading to structural instability during processing.
A carboxylic acid generator containing a carboxylic acid salt represented by formula (I), which includes specific hydrocarbon groups and acid labile groups, is used in a resist composition to enhance pattern stability.
The resist pattern formed using this composition exhibits improved pattern collapse resistance, ensuring structural integrity during processing.
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Figure 2026026041000001 
Figure 2026026041000002 
Figure 2026026041000003
Abstract
Description
[Technical Field]
[0001] The present invention relates to a carboxylic acid salt, a carboxylic acid generator, a resist composition, and a method for producing a resist pattern. [Background technology]
[0002] Patent Document 1 describes a carboxylate represented by the following formula and a resist composition containing the carboxylate as a carboxylic acid generator. TIFF2026026041000001.tif2867 [Prior art documents] [Patent documents]
[0003] [Patent Document 1] Japanese Patent Publication No. 2022-164584 Summary of the Invention [Problem to be solved by the invention]
[0004] The present invention provides a carboxylate salt that forms a resist pattern that has better pattern collapse resistance (PCM) than a resist pattern formed using a resist composition containing the above carboxylate salt. [Means for solving the problem]
[0005] The present invention includes the following inventions. [1] A carboxylic acid generator containing a carboxylic acid salt represented by formula (I). TIFF2026026041000002.tif28156 [In formula (I), m10 represents an integer of 1 to 3, and when m10 is 2 or greater, the groups in the parentheses may be the same or different. m11 represents an integer of 0 to 2, and satisfies 2≦m10+m11≦3; when m10+m11=2, X represents an iodine atom; when m10+m11=3, X represents a sulfur atom; and when m11 is 2 or greater, the groups in parentheses may be the same or different. A 1 and A 2 each independently represents a single bond or a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 11 It may be replaced by - or -CO-. R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or a heterocyclic hydrocarbon group having 4 to 9 carbon atoms, and the aromatic hydrocarbon group and the heterocyclic hydrocarbon group may have a substituent. R 1 and R 4 are each independently a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 Represents. *Ar 1 or Ar 2 represents the binding site with X 1 and X 2 each independently represents -CO-O-, -O-CO-, -O-CO-O- or -O-. L 11 represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is not selected from -O-, -S-, -SO2-, -SO-, and -NR 11 It may be replaced by - or -CO-. R 10 represents an acid labile group. R 2 and R 3each independently represents a halogen atom or a hydrocarbon group having 1 to 28 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 11 - or -CO-, and two R 2 , two R 3 or R 2 and R 3 is bonded, and X + and -CH2- contained in the ring may be -O-, -S-, -SO2-, -SO-, -NR 11 - or -CO-, and two R 2 , two R 3 or R 2 and R 3 is X + It may also be a single bond formed between two benzene rings connecting the m1 represents an integer of 1 to 5, and when m1 is 2 or greater, the groups in the parentheses may be the same or different. mm1 represents an integer from 2 to 5, and multiple R 1 may be the same or different from each other. m2 represents an integer of 0 to 4, and satisfies 1≦m1+m2≦5. When m2 is 2 or more, a plurality of R 2 may be the same or different from each other. m3 represents an integer of 0 to 5, and when m3 is 2 or more, a plurality of R 3 may be the same or different from each other. m4 represents an integer of 0 to 5, and satisfies 0≦m3+m4≦5. When m4 is 2 or more, the groups in the parentheses may be the same or different. mm4 represents 0 or 1. X 0 represents a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is not selected from -O-, -S-, -CO-, -SO-, and -NR 11 - or -SO2- may be replaced.] [2] The carboxylic acid generator according to [1], wherein the cation of the carboxylic acid salt represented by formula (I) is a cation represented by formula (IC-1). TIFF2026026041000003.tif26151[In formula (IC-1), m10, m11, X, A 1 , Ar 1 , m1, R 2 , R 3 , m2 and m3 have the same meanings as in formula (I). R 1A and R 1B are each independently a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents X 1 , X 2 , L 11 and R 10 have the same meanings as in formula (I). [3] The carboxylic acid generator according to [1] or [2], wherein m10 is 1 or 2. [4] The carboxylic acid generator according to any one of [1] to [3], wherein the cation of the carboxylate represented by formula (I) is one selected from the cations represented by formulas (IC-2) to (IC-10). TIFF2026026041000004.tif145161 [Formula (IC-2) ~ Formula (IC-10), A 1 , Ar 1 , m3, R 2 and R 3 , have the same meaning as in formula (I). R 1A , R 1B and R 1C are each independently a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents X 1 , X 2 , L 11 and R 10have the same meaning as in formula (I). X 7 represents a single bond, -CH2-, -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-.] [5]A 1 But **-X 01 -L 01 -or**-L 01 -X 01 - and X 01 -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2-, L 01 is a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is not limited to -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2- may be replaced. ** indicates Ar 1 The carboxylic acid generator according to any one of [1] to [4], wherein the bonding site is [6]L 01 is a single bond or an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-). [7]R 1 is a hydroxy group, *-OR 10 or *-OL 11 -CO-OR 10 (* indicates Ar 1 The carboxylic acid generator according to any one of [1] to [6], wherein [8]R 1 But *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 and R 10 The carboxylic acid generator according to any one of [1] to [7], wherein the acid labile group is a group represented by formula (1a) or a group represented by formula (2a). TIFF2026026041000005.tif2156 [In formula (1a), R aa1 , R aa2 and R aa3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded, and R aa3 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, and the alkyl group, alkenyl group, alicyclic hydrocarbon group, and aromatic hydrocarbon group may contain a halogen atom. * denotes a binding site.] TIFF2026026041000006.tif2161[In formula (2a), R aa1’ and R aa2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R aa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa1’ represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R aa2’ and R aa3’ are bonded to each other and they combine -CX a Together with -, they form a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom. X a represents an oxygen atom or a sulfur atom. * denotes a binding site.] [9] The carboxylic acid generator according to any one of [1] to [8], wherein X is a sulfur atom.
[10] Ar 1 is a group derived from a benzene ring, a naphthalene ring, a furan ring or a thiophene ring.
[11] X0 but, an alicyclic hydrocarbon group having 3 to 36 carbon atoms; an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group comprising a combination of a chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms, The alicyclic hydrocarbon group, the chain hydrocarbon group, and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group, and —CH— contained in the alicyclic hydrocarbon group and the chain hydrocarbon group may be —O—, —S—, —CO—, —SO—, —NR 11 The carboxylic acid generator according to any one of [1] to
[10] , wherein - or -SO2- may be substituted.
[12] X 0 is a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a hydroxy group.
[13] A resist composition comprising the carboxylic acid generator according to any one of [1] to
[12] and an acid generator other than the carboxylic acid generator.
[14] The resist composition according to
[13] , wherein the acid generator comprises a salt represented by formula (B1) or a salt represented by formula (B2). TIFF2026026041000007.tif1395[In formula (B1), L b1 represents a single bond or an (nb1+1)-valent hydrocarbon group which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO- or -SO2-. L b2 represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-. Y b1represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO- 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. Z1 + represents an organic cation. TIFF2026026041000008.tif1192[In formula (B2), A 1 represents a nitrogen atom or a carbon atom. L b2’ represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-. Y b1’ represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-. nb5 represents an integer of 2 or 3. When nb5 is 2, A 1 is a nitrogen atom and nb5 is 3, then A 1 is a carbon atom. The groups in parentheses may be the same or different, and two groups in parentheses are bonded to form A 1 may form a ring containing: Z2 + represents an organic cation.
[15] Further, the composition contains a resin including a structural unit having an acid labile group, The resist composition according to
[13] or
[14] , 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). TIFF2026026041000009.tif44144 [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or -O-(CH2) k1 represents —CO—O—, k1 represents an integer of 1 to 7, and * represents the bonding site with —CO—. R a01 , R a4 and R a5 each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these, 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 contain 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. TIFF2026026041000010.tif31118[In formula (a1-4), R a1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a17represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group. A a11 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group 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 -CO-. 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 a34 represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R a35 and R a36 are bonded to each other to form a divalent heterocyclic group having 3 to 20 carbon atoms together with the -CO- to which they are bonded, and -CH2- contained in the hydrocarbon group and the divalent heterocyclic group may be replaced with -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 between 0 and 2. TIFF2026026041000011.tif4558[In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom. Z a1is a single bond or -(CH2) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, * represents L 51 represents the binding site with L 51 , L 52 , L 53 and L 54 each independently represents -O- or -S-. s1 represents an integer of 1 to 3. s1' represents an integer of 0 to 3. TIFF2026026041000012.tif3581[In formula (a1-6), R a61 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a62 , R a63 and R a64 each independently represents an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, or R a62 and R a63 are bonded to each other to form a ring having 3 to 20 carbon atoms together with the carbon atoms to which they are attached, and R a64 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. X a61 is a single bond, -CO-O-* or -CO-NR a65 -*, * represents the binding 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, *-OL a61 -or*-CO-OL a62 -, * represents the 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.]
[16] The resist composition according to any one of
[13] to
[15] , further comprising a resin containing a structural unit represented by formula (a2-A). TIFF2026026041000013.tif30128[In formula (a2-A), R a2 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a27 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group. A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group 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 greater, 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 between 0 and 2.
[17] (1) A step of applying the resist composition according to any one of
[13] to
[16] onto a substrate; (2) 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:
[18] A carboxylate represented by the above formula (I). [Effects of the Invention]
[0006] By using a resist composition containing a carboxylate of the present invention, a resist pattern with good pattern collapse resistance (PCM) can be produced. DETAILED DESCRIPTION OF THE INVENTION
[0007] In this specification, "(meth)acrylic monomer" means "at least one of an acrylic monomer and a methacrylic monomer." The terms "(meth)acrylate" and "(meth)acrylic acid" have the same meaning. In the groups described in this specification, those that can have both a linear structure and a branched structure may have either. When -CH2- contained in a hydrocarbon group or the like is -O-, -S-, -CO-, -SO-, -NR X When replaced with - (X is any symbol) or -SO2-, the same examples apply to each group, and the number of carbon atoms before replacement is the number of carbon atoms in the hydrocarbon group, etc. "Combined group" refers to a group formed by combining two or more of the exemplified groups, and the valence of these groups may vary appropriately depending on the bonding form. "Derived from" or "derived from" refers to the polymerizable C=C bond contained in the molecule becoming a -CC- group (single bond) through polymerization. If stereoisomers exist, all stereoisomers are included. Depending on the number of substituents, etc., any position and number of hydrogen atoms contained in each group may be substituted for the bonding site. The number of carbon atoms in the substituent is not included in the number of carbon atoms in the substituted group. "Acid labile group" refers to a group that, upon contact with acid (e.g., trifluoromethanesulfonic acid, etc.), eliminates the leaving group to form a hydrophilic group (e.g., a hydroxy group or a carboxy group, etc.). The term "base labile group" refers to a group that, when contacted with a base (e.g., trimethylamine, tetramethylammonium hydroxide, etc.), eliminates the leaving group to form a hydrophilic group (e.g., a carboxy group or a hydroxy group, etc.). In this specification, the term "solids content of a resist composition" refers to the sum of all components in the resist composition excluding the solvent (E), which will be described later.
[0008] [Carboxylate represented by formula (I)] The present invention relates to a carboxylate salt represented by formula (I) (hereinafter sometimes referred to as "salt (I)" or "carboxylate (I)"). In carboxylate (I), the negatively charged side is sometimes called the "anion (I)" and the positively charged side is sometimes called the "cation (I)."
[0009] [Cation (I)] The cation (I) of the salt represented by formula (I) is a cation represented by formula (IC). TIFF2026026041000014.tif26152 [In formula (IC), all symbols have the same meaning as in formula (I)]
[0010] In formula (I), R 1 and R 4 X included in 1 is preferably *-CO-O-, *-O- or *-O-CO-O-, more preferably *-CO-O- or *-O- (where * is 1 Or L 11 or Ar 2 Or L 11 represents the binding site with ). R 1 and R 4 X included in 2 is preferably *-CO-O-, *-O-CO- or *-O-, more preferably *-CO-O- or *-O- (* is Ar 1 or Ar 2 represents the binding site with ). R 1 and R 4 L included in 11Examples of the hydrocarbon group in include linear or branched chain hydrocarbon groups such as alkanediyl groups, monocyclic or polycyclic (including spiro rings, fused rings, or bridged rings) alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may also be groups combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group or an aromatic hydrocarbon group and an alkanediyl group). Chain hydrocarbon groups and alicyclic hydrocarbon groups are also referred to as aliphatic hydrocarbon groups, and alicyclic hydrocarbon groups and aromatic hydrocarbon groups are also referred to as cyclic hydrocarbon groups. The hydrocarbon group preferably has 1 to 24 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 18 carbon atoms. Examples of the alkanediyl group include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl groups; Examples of branched alkanediyl groups include ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. The terminal of the branched alkanediyl group may be an alkyl group such as a methyl group. The chain hydrocarbon group may have 1 to 24 carbon atoms, preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, still more preferably 1 to 9, even more preferably 1 to 8, still more preferably 1 to 6, and even more preferably 1 to 4. Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following groups: The binding site can be any position. TIFF2026026041000015.tif42165Specifically, the alicyclic hydrocarbon group may be a monocyclic divalent alicyclic hydrocarbon group such as a cyclobutane-1,3-diyl group, a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, or a cyclooctane-1,5-diyl group, Examples of such divalent alicyclic hydrocarbon groups include cycloalkyl groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, adamantane-2,6-diyl, spirocyclohexane-1,2'-cyclopentane, and spiroadamantane-2,3'-cyclopentane, and polycyclic cycloalkanediyl groups such as spiro rings each having a cycloalkyl group bonded to a norbornyl or adamantyl group via a spiro bond. The number of carbon atoms in the alicyclic hydrocarbon group may be 3 to 24, preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. Examples of the aromatic hydrocarbon group include arylene groups such as a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, etc. The aromatic hydrocarbon group may have 6 to 24 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms. Examples of groups combining two or more of the chain hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group include a group combining an alicyclic hydrocarbon group with an alkanediyl group, a group combining an aromatic hydrocarbon group with an alkanediyl group, a group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group, and a group combining an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and an alkanediyl group. In the combination, two or more of each of the alicyclic hydrocarbon group, aromatic hydrocarbon group, and chain hydrocarbon group may be combined. In addition, when any group is X 1 or X 2 may be bound to Examples of groups combining an alicyclic hydrocarbon group and an alkanediyl group include -divalent alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent alicyclic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent alicyclic hydrocarbon group-. Examples of groups combining an aromatic hydrocarbon group and an alkanediyl group include -divalent aromatic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent aromatic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent aromatic hydrocarbon group-. Examples of groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group include -aromatic hydrocarbon group-alicyclic hydrocarbon group-, -alicyclic hydrocarbon group-aromatic hydrocarbon group-, and -alicyclic hydrocarbon group-aromatic hydrocarbon group-alicyclic hydrocarbon group-. L 11 -CH2- contained in the hydrocarbon group having 1 to 28 carbon atoms is -O-, -S-, -SO2-, -SO-, -NR 11 It may be replaced by - or -CO-. L 11 The -CH2- contained in the hydrocarbon group having 1 to 28 carbon atoms is -O-, -S-, -SO2-, -SO-, -NR 11 When it is replaced with - or -CO-, the number of carbon atoms before the replacement is regarded as the number of carbon atoms of the hydrocarbon group. R 11 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 4, and more preferably 1 to 3. R 11 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, even more preferably a hydrogen atom, a methyl group, or an ethyl group, and even more preferably a hydrogen atom or a methyl group. The -CH2- contained in the hydrocarbon group can be -O-, -S-, -SO2-, -SO-, or -NR 11Examples of the group substituted with - or -CO- include a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced with -S-), an amino group (a group in which -CH2- in a methyl group is replaced with -NR 11 -), oxy group (a group in which -CH2- in a methylene group is replaced with -O-), carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), thio group (a group in which -CH2- in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), peptide group (a group in which -CH2-CH2- in an ethylene group is replaced with -CO-NR 11 -), alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), alkylamino group (a group in which -CH2- at any position in an alkyl group is replaced with -NR 11 -), alkyl peptide group (wherein -CH2-CH2- at any position in the alkyl group is replaced by -CO-NR 11-), alkoxycarbonyl group (a group in which -CH2-CH2- at any position in the alkyl group is replaced with -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in the alkyl group is replaced with -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in the alkyl group is replaced with -CO-O-), alkoxycarbonyloxy group (a group in which -CH2-CH 2-CH2- is replaced by -O-CO-O-), alkoxyalkoxy group (a group in which two -CH2- at any position in an alkyl group are replaced by -O-), alkoxyalkyl group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), hydroxyalkyl group (a group in which -CH2- in a methyl group at any position in an alkyl group is replaced by -O-), alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced by -O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -O-), an alkanediylcarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -O-CO-), an alkanediylcarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (an alkanediyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyloxycarbon ... alkanediylsulfonyl group (a group in which -CH- at any position in an alkanediyl group is replaced with -SO-), alkanediylthio group (a group in which -CH- at any position in an alkanediyl group is replaced with -S-), alkanediylamino group (a group in which -CH- at any position in an alkanediyl group is replaced with -NR 11 -), alkanediyl peptide group (wherein any -CH2-CH2- at any position in the alkanediyl group is replaced by -CO-NR 11-substituted), cycloalkoxy groups, cycloalkylalkoxy groups, aromatic hydrocarbon group-carbonyloxy groups, aromatic hydrocarbon group-carbonyl groups, aromatic hydrocarbon group-oxy groups, and groups combining two or more of these groups. Examples of the alkoxy group include alkoxy groups having 1 to 27 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkylthio group include alkylthio groups having 1 to 27 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a 2-ethylhexylthio group, a nonylthio group, a decylthio group, an undecylthio group, etc. The number of carbon atoms in the alkylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 27 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a 2-ethylhexylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, etc. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkylamino group include alkylamino groups having 1 to 27 carbon atoms, such as methylamino group, ethylamino group, dimethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, etc. The number of carbon atoms in the alkylamino group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkyl peptide group include alkyl peptide groups having 1 to 27 carbon atoms, such as a methyl peptide group, an ethyl peptide group, a propyl peptide group, etc. The number of carbon atoms in the alkyl peptide group is preferably 1 to 11, more preferably 1 to 6, even 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 a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 28 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 27 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 26 carbon atoms, such as a butoxycarbonyloxy group. Examples of the alkoxyalkoxy group include alkoxyalkoxy groups having 2 to 26 carbon atoms, such as a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, and an ethoxyethoxy group. The alkoxycarbonyl group has preferably 2 to 11 carbon atoms, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkylcarbonyl group has preferably 2 to 12 carbon atoms, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkylcarbonyloxy group has preferably 2 to 11 carbon atoms, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkoxycarbonyloxy group has preferably 2 to 10 carbon atoms, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkoxyalkoxy group has preferably 2 to 10 carbon atoms, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. Examples of the alkoxyalkyl group include alkoxyalkyl groups having 2 to 27 carbon atoms, such as a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, and an ethoxyethyl group. The number of carbon atoms in the alkoxyalkyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of the hydroxyalkyl group include hydroxyalkyl groups having 1 to 27 carbon atoms, such as a hydroxymethyl group, a dihydroxymethyl group, a hydroxyethyl group, a dihydroxyethyl group, and a hydroxypropyl group. The number of carbon atoms in the hydroxyalkyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 27 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 27 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 28 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 27 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. Examples of the alkanediyloxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 26 carbon atoms, such as a butoxycarbonyloxy group. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyloxycarbonyloxy group is preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 27 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 27 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediylamino group include alkanediylamino groups having 1 to 27 carbon atoms, such as a methyleneamino group, an ethyleneamino group, a dimethyleneamino group, a propyleneamino group, a butyleneamino group, a pentyleneamino group, a hexyleneamino group, etc. The number of carbon atoms in the alkanediylamino group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyl peptide group include alkanediyl peptide groups having 1 to 27 carbon atoms, such as a methylene peptide group, an ethylene peptide group, a propylene peptide group, etc. The number of carbon atoms in the alkanediyl peptide group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 27 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 27 carbon atoms, such as a cyclohexylmethoxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 27 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 28 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 27 carbon atoms, such as a phenyloxy group.
[0011] In addition, -CH2- contained in an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these may be replaced with -O-, -S-, -CO-, -NR 11Examples of groups substituted with -, -SO- or -SO2- include the following groups: -O- or -CO- in the groups shown below are -S- and -NR2-, respectively. 11 The binding site may be at any position. TIFF2026026041000016.tif89165
[0012] L 11 Examples of the substituent that may be possessed by L include a halogen atom, a cyano group, and a nitro group. 11 However, in the case of a group in which an alicyclic hydrocarbon group or an aromatic hydrocarbon group is combined with a chain hydrocarbon group such as an alkyl group, the chain hydrocarbon group such as an alkyl group can be substantially used as a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. 11 -CH2- contained in the chain hydrocarbon group such as the alkyl group contained in 11 By replacing -, -SO- or -SO2-, L 11 can substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an alkoxyalkoxy group, an alkylamino group, an amino group, a thiol group, an alkylthio group, an alkylsulfonyl group, or an alkylpeptide group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L 11 The substituent in is preferably an alkyl group having 1 to 4 carbon atoms, a hydroxy group or a halogen atom, more preferably an alkyl group having 1 to 4 carbon atoms or a halogen atom, and further preferably a methyl group or a fluorine atom.
[0013] L 11 The alkyl group may be a chain hydrocarbon group having 1 to 12 carbon atoms (the chain hydrocarbon group may have a substituent). The —CH— contained in the chain hydrocarbon group may be —O—, —S—, —SO—, —SO—, —NR 11- or -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms (the cyclic hydrocarbon group may have a substituent. -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR 11 - or -CO-) or a group in which a chain hydrocarbon group having 1 to 6 carbon atoms is combined with a cyclic hydrocarbon group having 3 to 18 carbon atoms (the chain hydrocarbon group and the cyclic hydrocarbon group may have a substituent. -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR 11 - or -CO-), preferably an alkanediyl group having 1 to 10 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-) or a group combining an alkanediyl group having 1 to 4 carbon atoms with an alicyclic hydrocarbon group having 3 to 12 carbon atoms (-CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-), more preferably an alkanediyl group having 1 to 6 carbon atoms, even more preferably an alkanediyl group having 1 to 3 carbon atoms, and even more preferably a methylene group.
[0014] R 1 and R 4 R included in 10 The acid labile group in R is a group that, when contacted with an acid (e.g., trifluoromethanesulfonic acid, etc.), 10 When a leaving group including a group represented by the following formula is eliminated, it forms a carboxy group or a hydroxy group. The acid labile group is preferably a group represented by formula (1a) (hereinafter sometimes referred to as "acid labile group (1a)") or a group represented by formula (2a) (hereinafter sometimes referred to as "acid labile group (2a)"). TIFF2026026041000017.tif2156 [In formula (1a), R aa1 , R aa2 and R aa3each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded, and R aa3 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, and the alkyl group, alkenyl group, alicyclic hydrocarbon group, and aromatic hydrocarbon group may contain a halogen atom. * denotes a binding site.] TIFF2026026041000018.tif2161 [In formula (2a), R aa1’ and R aa2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R aa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa1’ represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R aa2’ and R aa3’ are bonded to each other and they combine -CX a Together with -, they form a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom. X a represents an oxygen atom or a sulfur atom. * denotes a binding site.]
[0015] R aa1 , R aa2 and R aa3 Examples of the alkyl group of R include a methyl group, an ethyl group, a propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group. aa1 , R aa2 and R aa3The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms. R aa1 , R aa2 and R aa3 Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. R aa1 , R aa2 and R aa3 The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (where * indicates a bonding site): aa1 , R aa2 and R aa3 The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms, and even more preferably 3 to 12 carbon atoms. TIFF2026026041000019.tif9159R aa1 , R aa2 and R aa3 Examples of the aromatic hydrocarbon group of R include aryl groups such as phenyl, naphthyl, anthryl, biphenyl, and phenanthryl. aa1 , R aa2 and R aa3 The aromatic hydrocarbon group preferably has 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms.
[0016] Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group.
[0017] R aa1 and R aa2 -C(R aa1 )(R aa2 )(R aa3 ) includes the following groups. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. * represents the bonding site with -O-. TIFF2026026041000020.tif30140
[0018] The group represented by formula (1a) is a 1,1,1-trialkyl group (R aa1 , R aa2 and R aa3 is an alkyl group, preferably a tert-butyl group), a 2-alkyladamantan-2-yl group (in formula (1a), R aa1 , R aa2 and the carbon atoms to which they are bonded form an adamantyl group, and R aa3 is an alkyl group) and 1-(adamantan-1-yl)-1,1-dialkyl groups (in formula (1a), R aa1 and R aa2 is an alkyl group, and R aa3is an adamantyl group).
[0019] R aa1' , R aa2' and R aa3' Examples of the hydrocarbon group include chain hydrocarbon groups such as alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups. The alkyl group and the alicyclic hydrocarbon group are represented by R aa1 , R aa2 and R aa3 Examples of the groups include the same groups as those listed in 1. Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group is combined with an alicyclic hydrocarbon group (for example, a cycloalkylalkyl group or an alkylcycloalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. R aa2' and R aa3' are bonded to each other and the carbon atoms to which they are bonded and X a When forming a heterocyclic group together with -C(R aa1' )(R aa2' )-X a -(R aa3' ) includes the following groups. * represents a bonding site. The heterocyclic group preferably has 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms, and even more preferably 3 to 12 carbon atoms. TIFF2026026041000021.tif21143Raa1' and R aa2' At least one of these is preferably a hydrogen atom. R aa1 , R aa2 , R aa3 , R aa1 , R aa2’ and R aa3’ The halogen atom that may be contained in the ring may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
[0020] Specific examples of the acid labile group (1a) include the following groups: * represents a bonding site. TIFF2026026041000022.tif72157
[0021] Specific examples of the acid labile group (2a) include the following groups: * represents a bonding site. TIFF2026026041000023.tif59148Ar 1 is a group derived from a benzene ring, R 1 Ar 1 The bonding positions to A are independently 1 The bonding position of A may be either o-position, m-position or p-position. 1 Preferably, at least one of the two is bonded at the p-position or m-position relative to the bonding position of Ar 1 is a group derived from a naphthalene ring, for example, A 1 When the bonding position of is the 1st position, it may be any of the 2nd to 8th positions. 1 When the bonding position of A is the 2nd position, it may be the 1st position or any of the 3rd to 8th positions. 1 When the bonding position of A is the 1st position, it is preferable that at least one of A is bonded to the 3rd to 6th positions. 1 When the bonding position of Ar is the 2nd position, it is preferable that at least one of Ar is bonded to the 4th to 7th positions. 2 is a group derived from a benzene ring or a naphthalene ring, R 4 Ar 2 The bonding position to R 1 Ar 1 The binding position is the same as that of R1 and R 4 each independently represents a hydroxy group, -OR 10 , -O-CO-OR 10 or -OL 11 -CO-OR 10 is preferably a hydroxy group, -OR 10 or -OL 11 -CO-OR 10 More preferably, -OR 10 or -OL 11 -CO-OR 10 It is more preferable that:
[0022] Ar 1 and Ar 2 Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include groups derived from a benzene ring or a naphthalene ring, such as a phenylene group or a naphthylene group. 1 and Ar 2 Examples of the heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms include groups derived from a furan ring, a thiophene ring, a benzofuran ring, or a benzothiophene ring. Ar 1 and Ar 2 are each independently preferably a group derived from a benzene ring, a naphthalene ring, a furan ring, or a thiophene ring, and more preferably a group derived from a benzene ring. Ar 1 and Ar 2 Examples of the substituent that the aromatic hydrocarbon group or heterocyclic hydrocarbon group may have include a halogen atom, a cyano group, a nitro group, or a hydrocarbon group having 1 to 28 carbon atoms. The hydrocarbon group may further have a substituent, and -CH2- contained in the hydrocarbon group is not limited to -O-, -S-, -SO2-, -SO-, -NR 11 It may be replaced by - or -CO-. Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the hydrocarbon group having 1 to 28 carbon atoms include chain hydrocarbon groups such as alkyl groups and alkanediyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups. The alkyl group is a linear or branched alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The alkanediyl group is a linear or branched alkanediyl group, such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, or a hexane-1,6-diyl group; and Examples of branched alkanediyl groups include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 9, still more preferably 1 to 8, even more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups shown below: The bonding site may be at any position. TIFF2026026041000024.tif42165Specific examples of monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl. Examples of polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl; cycloalkyl groups such as spirocyclohexane-1,2'-cyclopentane and spiroadamantane-2,3'-cyclopentane; and spiro rings having a cycloalkyl group bonded to a norbornyl or adamantyl group via a spiro bond.The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.
[0023] Examples of groups formed by combining two or more of chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups include groups formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*, alkyl group-aromatic hydrocarbon group-alkanediyl group-*, where -CH2- contained in the alkanediyl group and the alkyl group can be -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2-), a group in which an alicyclic hydrocarbon group and a chain hydrocarbon group are combined (for example, an alicyclic hydrocarbon group-alkanediyl group-*, an alkyl group-alicyclic hydrocarbon group-*, an alkyl group-alicyclic hydrocarbon group-alkanediyl group-*, -CH2- contained in the alicyclic hydrocarbon group, the alkanediyl group and the alkyl group may be replaced with -O-, -CO-, -S-, -SO-, -NR 11- or -SO2-), a group in which an aromatic hydrocarbon group and an alicyclic hydrocarbon group are combined (for example, an aromatic hydrocarbon group-alicyclic hydrocarbon group-*, an alicyclic hydrocarbon group-aromatic hydrocarbon group-*, where -CH2- contained in the alicyclic hydrocarbon group can be replaced by -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2-.) * indicates a binding site. The aromatic hydrocarbon group -alkanediyl group-* includes aralkyl groups such as benzyl group and phenethyl group. Examples of the alkyl group-aromatic hydrocarbon group-* include a tolyl group, a xylyl group, and a cumenyl group. Examples of the alicyclic hydrocarbon group -alkanediyl group-* include cycloalkylalkyl groups such as a cyclohexylmethyl group, a cyclohexylethyl group, a 1-(adamantan-1-yl)methyl group, and a 1-(adamantan-1-yl)-1-methylethyl group. Examples of the alkyl group-alicyclic hydrocarbon group-* include cycloalkyl groups having an alkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, and a 2-alkyladamantan-2-yl group. Examples of the aromatic hydrocarbon group-alicyclic hydrocarbon group-* include a phenylcyclohexyl group. Examples of the alicyclic hydrocarbon group-aromatic hydrocarbon group-* include a cyclohexylphenyl group. In addition, in the combination, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. 1 or Ar 2 may be bound to The substituents which the hydrocarbon group may have include the above-mentioned halogen atoms, cyano groups, nitro groups, etc. Examples of hydrocarbon groups having halogen atoms include chain hydrocarbon groups having halogen atoms such as haloalkyl groups, alicyclic hydrocarbon groups having halogen atoms such as halocycloalkyl groups, and aromatic hydrocarbon groups having halogen atoms. The haloalkyl group is preferably a haloalkyl group having 1 to 12 carbon atoms, and represents an alkyl group having 1 to 12 carbon atoms and a halogen atom, such as a fluorinated alkyl group having 1 to 12 carbon atoms, a chlorinated alkyl group having 1 to 12 carbon atoms, a brominated alkyl group having 1 to 12 carbon atoms, and an iodinated alkyl group having 1 to 12 carbon atoms. Examples of haloalkyl groups include perfluoroalkyl groups having 1 to 12 carbon atoms (such as a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a nonafluorobutyl group), a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, a 3,3,4,4,4-pentafluorobutyl group, a chloromethyl group, a bromomethyl group, and an iodomethyl group. The haloalkyl group preferably has 1 to 9 carbon atoms, more preferably 1 to 6 carbon atoms, even more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms. The -CH2- contained in the hydrocarbon group can be -O-, -S-, -SO2-, -SO-, or -NR 11 Examples of the group substituted with - or -CO- include a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a thiol group (a group in which -CH2- in a methyl group is replaced with -S-), an amino group (a group in which -CH2- in a methyl group is replaced with -NR 11-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), an alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), an alkoxycarbonyloxy group (a group in which -CH2-CH2-CH2- at any position in an alkyl group is replaced with , -O-CO-O-), alkoxyalkoxy group (a group in which two -CH2- at any position in an alkyl group are replaced with -O-), alkoxyalkyl group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), hydroxyalkyl group (a group in which -CH2- in a methyl group at any position in an alkyl group is replaced with -O-), alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), alkylamino group (a group in which -CH2- at any position in an alkyl group is replaced with -NR 11 -), alkyl peptide group (wherein -CH2-CH2- at any position in the alkyl group is replaced by -CO-NR 11 -), oxy group (a group in which -CH2- in a methylene group is replaced with -O-), carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), thio group (a group in which -CH2- in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), peptide group (a group in which -CH2-CH2- in an ethylene group is replaced with -CO-NR 11-), an alkanediyloxy group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -O-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced with -CO- O- is replaced by), alkanediyloxycarbonyloxy group (a group in which -CH2-CH2-CH2- at any position contained in an alkanediyl group is replaced by -O-CO-O-), alkanediylthio group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -S-), alkanediylsulfonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -SO2-), alkanediylamino group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -NR 11 -), alkanediyl peptide group (wherein any -CH2-CH2- at any position in the alkanediyl group is replaced by -CO-NR 11 -substituted), a cycloalkoxy group, a cycloalkylalkoxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group combining two or more of these groups. These substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.
[0024] In addition, -CH2- contained in an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these may be -O-, -S-, -SO2-, -SO-, -NR 11 Examples of the group substituted with - or -CO- include the same groups as those exemplified in this specification, within the upper limit of the carbon number. Ar 1 and Ar 2The substituents are each independently preferably a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), more preferably a fluorine atom, an iodine atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a haloalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-). O-) is more preferred, a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a hydroxy group, a carboxy group, or an alkoxy group having 1 to 3 carbon atoms is even more preferred, a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 3 carbon atoms, a hydroxy group, a carboxy group, or an alkoxy group having 1 to 3 carbon atoms is even more preferred, and a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, an ethyl group, a hydroxy group, a carboxy group, a methoxy group, or an ethoxy group is even more preferred. Ar 1 The bonding position of the substituent in Ar 1 are groups derived from a benzene ring, each independently 1 In particular, when there is one substituent, each of the substituents independently may be one of the following: 1 When there are two substituents, the substituents are preferably bonded to the p-position or m-position relative to the bonding position of A. 1 It is preferred that one is bonded to the o-position or m-position and the other is bonded to the p-position or m-position with respect to the bonding positions of A. 1 Preferably, two of them are bonded to the o-position or m-position, and one is bonded to the p-position or m-position with respect to the bonding positions of Ar 1 is a group derived from a naphthalene ring, for example, A 1When the bonding position of is the 1st position, it may be any of the 2nd to 8th positions. 1 When the bonding position of A is the 2nd position, it may be the 1st position or any of the 3rd to 8th positions. 1 When the bonding position of A is the 1st position, it is preferable that at least one of A is bonded to the 3rd to 6th positions. 1 , A 2 and A 3 When the bonding position of Ar is the 2nd position, it is preferable that at least one of Ar is bonded to the 4th to 7th positions. 2 The bonding position of the substituent in Ar 1 The bonding positions of the substituents are the same as those in
[0025] A 1 and A 2 Examples of the hydrocarbon group include linear or branched chain hydrocarbon groups (e.g., alkanediyl groups, etc.), monocyclic or polycyclic alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be a combination of two or more of these groups. The number of carbon atoms in the hydrocarbon group is preferably 1 to 19, more preferably 1 to 18, even more preferably 1 to 16, still more preferably 1 to 14, and even more preferably 1 to 12. Examples of the chain hydrocarbon group include straight-chain alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl; Examples of branched alkanediyl groups include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, still more preferably 1 to 9, even more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups shown below: The bonding site may be at any position. TIFF2026026041000025.tif42165Specifically, monocyclic alicyclic hydrocarbon groups such as monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, and cyclooctane-1,5-diyl group; Examples include polycyclic alicyclic hydrocarbon groups such as polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, and adamantane-2,6-diyl; cycloalkyl groups such as spirocyclohexane-1,2'-cyclopentane and spiroadamantane-2,3'-cyclopentane; and spiro rings having a cycloalkyl group bonded to a norbornyl group or an adamantyl group via a spiro bond. The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms, even more preferably 3 to 12 carbon atoms, and even more preferably 3 to 10 carbon atoms. Examples of the aromatic hydrocarbon group include arylene groups such as a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, etc. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.
[0026] Examples of groups formed by combining groups include a group formed by combining an alicyclic hydrocarbon group with an alkanediyl group, a group formed by combining an aromatic hydrocarbon group with an alkanediyl group, and a group formed by combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group. In the combination, two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups may be combined. Furthermore, any of the groups may be bonded to a benzene ring. Examples of groups combining an alicyclic hydrocarbon group and an alkanediyl group include -divalent alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent alicyclic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent alicyclic hydrocarbon group-. Examples of groups combining an aromatic hydrocarbon group and an alkanediyl group include -divalent aromatic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent aromatic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent aromatic hydrocarbon group-. Examples of groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group include -aromatic hydrocarbon group-alicyclic hydrocarbon group-, -alicyclic hydrocarbon group-aromatic hydrocarbon group-, and -alicyclic hydrocarbon group-aromatic hydrocarbon group-alicyclic hydrocarbon group-.
[0027] A 1 and A 2 In this case, -CH2- contained in the hydrocarbon group can be -O-, -CO-, -S-, -SO-, -NR 11 When the hydrocarbon group is substituted with - or -SO2-, the number of carbon atoms before the substitution is taken as the total number of carbon atoms in the hydrocarbon group. The number may be 1 or 2 or more, but is preferably 1 or 2. The -CH2- contained in the hydrocarbon group can be -O-, -CO-, -S-, -SO-, or -NR 11Examples of the group substituted for - or -SO2- include a hydroxy group, a carboxy group, a thiol group, an amino group, an oxy group, a carbonyl group, a thio group, a sulfonyl group, a peptide group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkylamino group, an alkylpeptide group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an alkoxyalkoxy group, an alkoxyalkyl group, a hydroxyalkyl group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediyloxycarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, an alkanediylamino group, an alkanediylpeptide group, a cycloalkoxy group, a cycloalkylalkoxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group formed by combining two or more of these groups. These substituted groups include the same groups as those exemplified in this specification, within the limits permitted by the upper limit of the number of carbon atoms.
[0028] In addition, -CH2- contained in an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these may be -O-, -CO-, -S-, -SO-, -NR 11 The group substituted with - or -SO2- includes the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. A 1 and A 2 The hydrocarbon group may have a substituent such as Ar 1 and Ar 2 Examples of the substituent include the same groups as those exemplified as the substituents that the aromatic hydrocarbon group or heterocyclic aromatic hydrocarbon group may have.
[0029] A 1 and A 2 each independently represents a hydrocarbon group having 1 to 20 carbon atoms (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is not limited to -O-, -CO-, -S-, -SO-, -NR 11- or -SO2-, provided that at least one of -CH2- contained in the hydrocarbon group is not -O-, -CO-, -S-, -SO-, or -NR2-. 11 - or -SO2- is preferably used. 1 is **-L 011 -X 01 -L 012 -is (X 01 -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2-. 011 and L 012 each independently represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2- may be replaced. 011 and L 012 The total number of carbon atoms is 0 to 18. ** indicates Ar 1 It is more preferable that A 1 is **-X 01 -L 01 -or**-L 01 -X 01 -is (X 01 each independently represents -O-, -CO-, -S-, -SO-, or -NR 11 - or -SO2-. 01 represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is not -O-, -CO-, -S-, -SO-, or -NR 11 - or -SO2- may be replaced. ** indicates Ar 1 It is more preferable that A 1 -O-, -CO-, -S-, -SO-, -NR 11 Those having no substituents other than the - or -SO2- substitution are also preferred. L 011 , L 012 and L 01a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is not limited to -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2-) has a carbon number of 1 to 18, and A 1 Examples of the groups include the same groups as those listed in the above. X 01 each independently represents -O-, -CO-, -S-, or -NR 11 - or -SO2- is preferred, and -O-, -CO-, -S- or -NR 11 It is more preferably -, further preferably -O-, -CO- or -S-, and even more preferably -O- or -CO-. L 011 , L 012 and L 01 are each independently a single bond or a hydrocarbon group having 1 to 18 carbon atoms (-CH2- contained in the hydrocarbon group is not limited to -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2-), and a single bond or a hydrocarbon group having 1 to 12 carbon atoms (the -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2-) is more preferred, and a single bond, a chain hydrocarbon group having 1 to 9 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or a group in which a chain hydrocarbon group having 1 to 4 carbon atoms and an alicyclic hydrocarbon group having 3 to 10 carbon atoms are combined (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S-, -SO-, -NR 11- or -SO2-), even more preferably a single bond or an alkanediyl group having 1 to 6 carbon atoms (wherein -CH2- in the alkanediyl group may be replaced by -O- or -CO-), even more preferably a single bond or an alkanediyl group having 1 to 4 carbon atoms (wherein -CH2- in the alkanediyl group may be replaced by -O- or -CO-), and even more preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms (wherein -CH2- in the alkanediyl group may be replaced by -O- or -CO-). Among these, a single bond, a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-2,2-diyl group, an oxy group, a carbonyl group, a carbonyloxy group, a carbonyloxymethylene group, an ethyleneoxy group, an ethyleneoxymethylene group, a methylenecarbonyloxy group, a methylenecarbonyloxymethylene group, or an ethyleneoxycarbonyl group is preferred, and a single bond, a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-2,2-diyl group, an oxy group, or a carbonyl group is more preferred. 011 and L 012 The total number of carbon atoms is 0 to 18. A 2 Regarding A 1 Groups similar to the following are preferred. Also, A 1 and A 2 each independently represents a single bond, a chain hydrocarbon group having 1 to 20 carbon atoms, a cyclic hydrocarbon group having 3 to 20 carbon atoms, or a hydrocarbon group having 4 to 20 carbon atoms, which is a combination thereof (provided that the chain hydrocarbon group and the cyclic hydrocarbon group may have a substituent, and -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group is not -O-, -S-, -SO2-, -SO-, -NR 11In this case, a single bond, a chain hydrocarbon group having 1 to 18 carbon atoms, a cyclic hydrocarbon group having 3 to 18 carbon atoms, or a hydrocarbon group having 4 to 18 carbon atoms by combining these (however, the chain hydrocarbon group and the cyclic hydrocarbon group may have a substituent, and -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR 11 - or -CO- may be substituted.) is more preferred. A 1 and A 2 X + The bonding positions of X to the benzene ring are each independently + The bonding position of X may be either o-position, m-position or p-position. + More specifically, when m1 is 1, A 1 are each independently, X + It is preferably bonded to the p-position or m-position, more preferably to the p-position, relative to the bonding position of A. 1 are each independently, X + With respect to the bonding positions of A, it is preferable that one is bonded to the o-position or the m-position, and one is bonded to the o-position or the m-position, and it is more preferable that two are bonded to the m-position. 1 are each independently, X + With respect to the bonding positions of A, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position. 1 are each independently, X + With respect to the bonding positions of A, it is preferred that two are bonded to the o-position or m-position, and two are bonded to the p-position or m-position, and it is more preferred that two are bonded to the o-position and two are bonded to the m-position. 2 X + The bond position to the benzene ring to which A is attached is also 1 X + The bond position to the benzene ring is the same as that to which the mm1 is preferably 2, 3 or 4, more preferably 2 or 3, and even more preferably 2. m1 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. m2 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. m3 is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1. m4 is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2, even more preferably 0 or 1, and even more preferably 0.
[0030] R 2 and R 3 The halogen atoms are Ar 1 Examples of the halogen atoms include the same halogen atoms as those exemplified as the substituents that may be possessed by the group. R 2 and R 3 a hydrocarbon group having 1 to 28 carbon atoms (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is not limited to -O-, -S-, -SO2-, -SO-, -NR 11 - or -CO- may be replaced by L 11 or Ar 1 The hydrocarbon groups listed as the substituents that may be possessed by the hydrocarbon group (the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is not limited to -O-, -S-, -SO2-, -SO-, -NR 11 - or -CO- may be substituted.) R 2 and R 3 The hydrocarbon group may be a group having an acid labile group at the end, and for example, within the range permitted by the upper limit of the number of carbon atoms, R 1 *-X shown in the example 1 -R10 and *-X 2 -L 11 -X 1 -R 10 or *-A 1 -Ar 1 -X 1 -R 10 and *-A 1 -Ar 1 -X 2 -L 11 -X 1 -R 10 (* indicates R 2 or R 3 This should be read as the bonding site between the benzene ring and the bonded group. R 2 and R 3 each independently represents a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the haloalkyl group and the alkyl group may be replaced by -O- or -CO-), -OR 10 , -O-CO-OR 10 or -OL 11 -CO-OR 10 and a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced by —O— or —CO—), —OR 10 , -O-CO-OR 10 or -OL 11 -CO-OR 10 and more preferably a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced by —O— or —CO—), —OR 10 , -O-CO-OR 10 or -OL 11 -CO-OR 10 It is more preferable that the group is a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a hydroxy group, a carboxy group, an alkoxy group having 1 to 3 carbon atoms, -OR 10 , -O-CO-OR 10 or -OL11 -CO-OR 10 It is more preferable that the alkyl group is a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, an ethyl group, a t-butyl group, a hydroxy group, a carboxy group, a methoxy group, an ethoxy group, or -OR 10 , -O-CO-OR 10 or -OL 11 -CO-OR 10 It is even more preferred that: R 2 and R 3 The bonding positions of X to the benzene ring are each independently + The bonding position of R may be either o-position, m-position, or p-position. 2 are each independently, X + It is preferably bonded to the p-position or m-position, more preferably to the p-position, relative to the bonding position of R 2 are each independently, X + With respect to the bonding positions of R, it is preferred that one is bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that one is bonded to the m-position and one is bonded to the p- or m-position. 2 are each independently, X + With respect to the bonding positions of R, it is preferred that two are bonded to the o- or m-position and one is bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position and one is bonded to the p-position. 2 are each independently, X + With respect to the bonding positions of R, it is preferred that two are bonded to the o- or m-position and two are bonded to the p- or m-position, and it is more preferred that two are bonded to the m-position, one is bonded to the o-position, and one is bonded to the p-position. 3 The bonding position of R to the benzene ring is also 2 The bonding position to the benzene ring is the same as that of
[0031] The Two R's 2 , two R 3 or R 2 and R 3 is bonded, and X+ When forming a ring containing: X is preferably a sulfur atom, and for example, is preferably a cation represented by the following formula (IC'). TIFF2026026041000026.tif51153[In formula (I-C'), R 1A , R 1B and R 1C are each independently represented by the formula (I), R 1 It has the same meaning as: R 2A , R 2B and R 2C are each independently represented by the formula (I), R 2 It has the same meaning as: A 1A , A 1B and A 1C are each independently a group represented by the formula (I), A 1 It has the same meaning as: Ar 1A , Ar 1B and Ar 1C are each independently represented by the formula (I), Ar 1 It has the same meaning as: mm1A, mm1B and mm1C each independently represent an integer of 1 to 5, and any one of mm1A, mm1B and mm1C represents an integer of 2 or more. m1A represents an integer of 0 to 5, and when m1A is 2 or more, the groups in the parentheses may be the same or different. m2A represents an integer of 0 to 5, and satisfies 0≦m1A+m2A≦5, and when m2A is 2 or more, the groups in the parentheses may be the same or different. m1B and m1C each independently represent an integer of 0 to 4, and when m1B and m1C each represent 2 or more, the groups in the respective parentheses may be the same or different. m2B and m2C each independently represent an integer of 0 to 4, satisfying 0≦m1B+m2B≦4 and 0≦m1C+m2C≦4, respectively, and when m2B and m2C are each 2 or more, the groups in each of the multiple parentheses may be the same or different. Any one of m1A, m1B, and m1C represents an integer of 1 or more. X 7 represents a single bond, -CH2-, -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-.] X 7 is preferably a single bond, —CH 2 — or —O—.
[0032] The cation represented by formula (IC) is preferably a cation represented by formula (IC-1). TIFF2026026041000027.tif26151[In formula (IC-1), m10, m11, X, A 1 , Ar 1 , m1, R 2 , R 3 , m2 and m3 have the same meanings as in formula (I). R 1A and R 1B are each independently a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents X 1 , X 2 , L 11 and R 10 have the same meanings as in formula (I). Furthermore, the cation represented by formula (IC) is preferably a cation represented by the following formulas (IC-2) to (IC-10). TIFF2026026041000028.tif145161 [Formula (IC-2) ~ Formula (IC-10), A 1 , Ar 1 , m3, R 2 and R 3 has the same meaning as in formula (I). R 1A , R 1B and R 1C are each independently a hydroxy group, *-X 1 -R 10 or *-X2 -L 11 -X 1 -R 10 represents X 1 and X 2 and L 11 and R 10 each represent the same meaning as formula (I). X 7 represents the same meaning as formula (I-C’). In formulas (I-C-2) to (I-C-10), the subscript numbers near the outside of each parenthesis represent valence, and "P1 - P2 (where P1 and P2 are both integers and P1 < P2)" means "represents any integer from P1 to P2". For example, in formula (I-C-2), the "0 - 2" in (R 2 ) 0-2 represents "any integer from 0 to 2", and in formulas (I-C-2) to (I-C-10), the subscript numbers near the outside of other parentheses also represent the same meaning.
[0033] Examples of the cation of salt (I) include cations represented by the following formulas (I-c-1) to (I-c-105).[[ID=3 TIFF2026026041000036.tif252160
[0041] TIFF2026026041000037.tif119111
[0042] [Anion (I)] In formula (I), X 0 Examples of the hydrocarbon group represented by the formula (I) include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkyl groups, alkenyl groups, and alkynyl groups, and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, and groups combining these groups. The -CH2- contained in the hydrocarbon group can be -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2- may be substituted. In the hydrocarbon group, CO2 - The atom adjacent to is preferably a carbon atom, and in the aliphatic hydrocarbon group, CO - The atom adjacent to is more preferably a carbon atom. The number of carbon atoms in the hydrocarbon group is, for example, 1 to 64, may be 2 to 48, is preferably 2 to 36, more preferably 2 to 30, still more preferably 2 to 24, still more preferably 2 to 18, and still more preferably 2 to 12. X 0 The alkyl group in the formula (I) may be a linear or branched alkyl group, such as 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. The number of carbon atoms in the alkyl group is preferably 2 to 18, more preferably 2 to 12, still more preferably 2 to 9, still more preferably 2 to 6, and still more preferably 2 to 4. X 0 Examples of the alkenyl group in the formula (I) include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. X 0Examples of the alkynyl group in the formula (I) include an ethynyl group, a propynyl group, an isopropynyl group, a butynyl group, an isobutynyl group, a tert-butynyl group, a pentynyl group, a hexynyl group, an octynyl group, and a nonynyl group. The chain hydrocarbon group may have 1 to 36 carbon atoms, preferably 2 to 18 carbon atoms, more preferably 2 to 12 carbon atoms, even more preferably 2 to 9 carbon atoms, even more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms. X 0 The -CH2- contained in the chain hydrocarbon group in 11 Examples of the group substituted with - or -SO2- include a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced with -S-), an amino group (a group in which -CH2- in a methyl group is replaced with -NR 11 -), carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), thio group (a group in which -CH2- in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), peptide group (a group in which -CH2-CH2- in an ethylene group is replaced with -CO-NR 11 -), oxy group (a group in which -CH2- in a methylene group is replaced with -O-), alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), alkylamino group (a group in which -CH2- at any position in an alkyl group is replaced with -NR 11 -), alkyl peptide group (wherein -CH2-CH2- at any position in the alkyl group is replaced by -CO-NR 11-), alkoxycarbonyl group (a group in which -CH2-CH2- at any position in the alkyl group is replaced with -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in the alkyl group is replaced with -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in the alkyl group is replaced with -CO-O-), alkoxycarbonyloxy group (a group in which -CH2-CH 2-CH2- is replaced by -O-CO-O-), alkoxyalkoxy group (a group in which two -CH2- at any position in an alkyl group are replaced by -O-), alkoxyalkyl group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), hydroxyalkyl group (a group in which -CH2- in a methyl group at any position in an alkyl group is replaced by -O-), alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced by -O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -O-), an alkanediylcarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -O-CO-), an alkanediylcarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (an alkanediyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyloxycarbon ... alkanediylsulfonyl group (a group in which -CH- at any position in an alkanediyl group is replaced with -SO-), alkanediylthio group (a group in which -CH- at any position in an alkanediyl group is replaced with -S-), alkanediylamino group (a group in which -CH- at any position in an alkanediyl group is replaced with -NR 11 -), alkanediyl peptide group (wherein any -CH2-CH2- at any position in the alkanediyl group is replaced by -CO-NR 11-substituted), a cycloalkoxy group, a cycloalkylalkoxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group combining two or more of these groups. These substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. The alkoxy group, hydroxyalkyl group, etc. may have 1 to 36 carbon atoms, may have 1 to 17 carbon atoms, is preferably 1 to 11 carbon atoms, is more preferably 1 to 6 carbon atoms, is further preferably 1 to 4 carbon atoms, and is still further preferably 1 to 3 carbon atoms. The alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkoxycarbonyloxy group, alkoxyalkyl group, etc. may have 2 to 36 carbon atoms, may have 2 to 17 carbon atoms, is preferably 2 to 11 carbon atoms, is more preferably 2 to 6 carbon atoms, is further preferably 2 to 4 carbon atoms, and is further preferably 2 to 3 carbon atoms. The alkylthio group, alkylsulfonyl group, alkylamino group, alkylpeptide group, and the like have 1 to 36 carbon atoms, and may have 1 to 17 carbon atoms, preferably 1 to 11 carbon atoms, more preferably 1 to 6 carbon atoms, even more preferably 1 to 4 carbon atoms, and still more preferably 1 to 3 carbon atoms. Examples of the alkanediyloxy group, alkanediyloxycarbonyl group, alkanediylcarbonyl group, alkanediylcarbonyloxy group, alkanediyloxycarbonyloxy group, alkanediylsulfonyl group, alkanediylthio group, alkanediylamino group, alkanediylpeptide group, and the like include groups in which one hydrogen atom at any position in an alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkylthio group, alkylsulfonyl group, alkylamino group, alkylpeptide group, etc. is replaced with a binding site. The substitution in the alkenyl group or alkynyl group may be any of the substitutions in the alkyl group exemplified above, as long as it contains a carbon-carbon double bond or a carbon-carbon triple bond at any position. The alicyclic hydrocarbon group may be any of monocyclic, polycyclic, and spiro rings, and may be any of saturated and unsaturated. Examples of the alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl groups, polycyclic cycloalkyl groups such as norbornyl and adamantyl groups, and spiro rings having a cycloalkyl group bonded to a cycloalkyl group, norbornyl group, or adamantyl group via a spiro bond. X 0 Examples of the alicyclic hydrocarbon group in the formula (I) include the following groups: The bonding site can be at any position. TIFF2026026041000038.tif42165 The number of carbon atoms in the alicyclic hydrocarbon group may be 3 to 48, preferably 3 to 36, more preferably 3 to 24, even more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12. X 0 Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, and a binaphthyl group. The aromatic hydrocarbon group may have 6 to 48 carbon atoms, preferably 6 to 36, more preferably 6 to 24, still more preferably 6 to 18, even more preferably 6 to 14, and still more preferably 6 to 10.
[0043] X 0 In the above, -CH2- contained in the alicyclic hydrocarbon group, aromatic hydrocarbon group or a group combining these is -O-, -S-, -CO-, -SO-, -NR 11 The group substituted with - or -SO2- may form an ether ring, a ketone ring, a lactone ring, a sultone ring, an acetal ring, or the like, and specific examples thereof include the following groups. In addition, among the groups shown below, -O- is -S-, and -CO- is -NR 11 Also included are groups substituted with -, -SO-, or -SO2-. The binding site can be at any position. TIFF2026026041000039.tif89165X 0 When is the above-mentioned combined group, the combined group may contain the above-mentioned groups with different valences (such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, a cycloalkanediyl group, a cycloalkanetriyl group, or a cycloalkanetetrayl group).
[0044] The combined group is a group in which an alicyclic hydrocarbon group and a chain hydrocarbon group are combined (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group is not an -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), a group in which a chain hydrocarbon group and an aromatic hydrocarbon group are combined (-CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), and a group in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are combined (the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR2-, - 11 - or -SO2-). As for the combination of groups, two or more types of alicyclic hydrocarbon groups, chain hydrocarbon groups and aromatic hydrocarbon groups may be combined. Specifically, the combined groups include alicyclic hydrocarbon groups such as an adamantyl methylene group and a cyclohexyl methylene group, chain hydrocarbon groups, (alicyclic hydrocarbon groups) 2-chain hydrocarbon groups, (wherein -CH2- contained in the chain hydrocarbon groups and the alicyclic hydrocarbon groups is not -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), a chain hydrocarbon group such as a methyladamantyl group or a dimethyladamantyl group - alicyclic hydrocarbon group-*, (chain hydrocarbon group)2-alicyclic hydrocarbon group-* (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11- or -SO2-), a chain hydrocarbon group such as a tolyl group or a xylyl group - an aromatic hydrocarbon group -* (-CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), a chain hydrocarbon group such as a methylcyclohexylmethylene group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), aromatic hydrocarbon group such as benzyl group - chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), a chain hydrocarbon group such as a tolylmethyl group - an aromatic hydrocarbon group - a chain hydrocarbon group-* (the -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), a chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-* such as a methyladamantanemethyleneadamantyl group or a di(methyladamantanemethylene)adamantyl group, (chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group)2-alicyclic hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-alicyclic hydrocarbon group-*, (chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group is not limited to -O-, -S-, -CO-, -SO-, -NR 11- or -SO2-), alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (alicyclic hydrocarbon group) 2-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (alicyclic hydrocarbon group-chain hydrocarbon group) 2-alicyclic hydrocarbon group-chain hydrocarbon group-*, (alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group) 2-chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group is not -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group is not -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), etc. Here, * represents the bonding site with the carbon atom of the carbonyl group. X 0 -CH2- contained in the hydrocarbon group represented by the formula: 11 When X is replaced with - or -SO2-, the number of carbon atoms before the replacement is the total number of carbon atoms in the hydrocarbon group. 0 When a substituent is bonded to a hydrocarbon group represented by the following formula, the number of carbon atoms before substitution is taken as the total number of carbon atoms in the hydrocarbon group. X 0 The hydrocarbon group represented by the formula (I) may have one or more substituents. X 0 Examples of the substituent that the hydrocarbon group represented by the formula (I) may have include a hydroxy group, a halogen atom, a cyano group, and a nitro group. Also, X 0is a group in which an alicyclic hydrocarbon group or an aromatic hydrocarbon group is combined with a chain hydrocarbon group such as an alkyl group, the chain hydrocarbon group such as an alkyl group may be regarded as a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. 0 The -CH2- of the chain hydrocarbon group such as an alkyl group contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2- to replace X 0 The hydrocarbon group may substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an alkoxyalkoxy group, an alkylamino group, an amino group, a thiol group, an alkylthio group, an alkylsulfonyl group, or an alkylpeptide group. X 0 Examples of the halogen atom that may be contained in the hydrocarbon group represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. X 0 The hydrocarbon group represented by the formula (I) is preferably an aliphatic hydrocarbon group having 2 to 72 carbon atoms which may have a substituent (-CH2- contained in the aliphatic hydrocarbon group is not limited to -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), a hydrocarbon group having 6 to 72 carbon atoms including an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent (-CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR2-, 11 - or -SO2-), a group represented by formula (aa) or a group represented by formula (bb).
[0045] X 0 More preferably, the hydrocarbon group represented by the formula (I) is an alicyclic hydrocarbon group which may have a halogen atom, an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group (the -CH2- contained in the alicyclic hydrocarbon group is not -O-, -S-, -CO-, -SO-, -NR 11- or -SO2-), a group in which an alicyclic hydrocarbon group and a chain hydrocarbon group are combined (the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR2-, 11 - or -SO2-, -CH2- 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, an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or a hydroxy group), an aromatic hydrocarbon group which may have a halogen atom, an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or a hydroxy group, a group combining an aromatic hydrocarbon group with a chain hydrocarbon group (-CH2- in 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, an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or a hydroxy group), a group represented by formula (aa) or a group represented by formula (bb). X 0 More preferably, the hydrocarbon group represented by the formula (I) is an alicyclic hydrocarbon group (wherein -CH2- in the alicyclic hydrocarbon group is not -O-, -S-, -CO-, -SO-, -NR 11 The alicyclic hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-alicyclic hydrocarbon group-chain hydrocarbon group (-CH2- contained in the alicyclic hydrocarbon group is not -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-, and -CH2- contained 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 fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO -represents a bonding site with a carbon atom of the formula (I), *-chain hydrocarbon group-alicyclic hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 The chain hydrocarbon group and the alicyclic hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-aromatic hydrocarbon group (the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I).), *-aromatic hydrocarbon group-chain hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, and the chain hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-chain hydrocarbon group-aromatic hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, and the chain hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * represents -COO - represents a bonding site with the carbon atom of formula (aa), a group represented by formula (bb). X 0 More preferably, the hydrocarbon group represented by the formula (I) is a polycyclic alicyclic hydrocarbon group (wherein -CH2- contained in the polycyclic alicyclic hydrocarbon group is -O-, -S-, -CO-, -SO-, -NR 11 The polycyclic alicyclic hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO- represents a bonding site with a carbon atom of the formula (1), *-polycyclic alicyclic hydrocarbon group-chain hydrocarbon group (-CH2- contained in the polycyclic alicyclic hydrocarbon group is not -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the polycyclic alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-chain hydrocarbon group-polycyclic alicyclic hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH2- contained in the polycyclic alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 The chain hydrocarbon group and the polycyclic alicyclic hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-aromatic hydrocarbon group (the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO - represents a bonding site with the carbon atom of formula (aa), a group represented by formula (bb).
[0046] X 0 Particularly preferred hydrocarbon groups represented by the formula (aa) are an adamantyl group, an adamantanone group, a hydroxyadamantyl group, a group combining an adamantyl group with an alkyl group (wherein —CH— contained in the alkyl group may be replaced by —O— or —CO—), a group represented by the formula (Y30F), a phenyl group having a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, a group represented by the formula (aa), or a group represented by the formula (bb). Also, X 0represents an aliphatic hydrocarbon group having 2 to 72 carbon atoms which may have a substituent (-CH2- contained in the aliphatic hydrocarbon group is not limited to -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-) or a hydrocarbon group having 6 to 72 carbon atoms including an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent (-CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR2-, ... 11 - or -SO2- may be replaced.) X 0 represents an alicyclic hydrocarbon group having 3 to 36 carbon atoms which may have a halogen atom, an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group (-CH2- contained in the alicyclic hydrocarbon group is not limited to -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-), a group in which an alicyclic hydrocarbon group having 3 to 36 carbon atoms is combined with a chain hydrocarbon group having 1 to 18 carbon atoms (the -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-, and -CH2- 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, an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or a hydroxy group.), an aromatic hydrocarbon group of 6 to 36 carbon atoms which may have a halogen atom, an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or a hydroxy group, or a group combining an aromatic hydrocarbon group of 6 to 36 carbon atoms with a chain hydrocarbon group of 1 to 18 carbon atoms (-CH2- in 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, an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or a hydroxy group). Among them, X 0represents an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group in which a chain hydrocarbon group having 1 to 18 carbon atoms is combined with an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms (the alicyclic hydrocarbon group, the chain hydrocarbon group, and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group, and -CH2- contained in the alicyclic hydrocarbon group and the chain hydrocarbon group is not -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2- may be substituted.) is preferred. In the above groups, the alicyclic hydrocarbon group may have 3 to 48 carbon atoms, preferably 3 to 36, more preferably 3 to 24, even more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12. The chain hydrocarbon group has preferably 1 to 18 carbon atoms, more preferably 1 to 12, even more preferably 1 to 9, still more preferably 1 to 6, and even more preferably 1 to 4. The aromatic hydrocarbon group may have 6 to 48 carbon atoms, preferably 6 to 36, more preferably 6 to 24, even more preferably 6 to 18, still more preferably 6 to 14, and even more preferably 6 to 10.
[0047] The group represented by formula (aa), the group represented by formula (bb) and the group represented by formula (Y30F) are groups represented by the following formulas. TIFF2026026041000040.tif27136[In formula (aa), X a and X b each independently represents -O- or -S-. X 1a represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is not selected from -O-, -S-, -CO-, -SO-, and -NR 11 It may be replaced by - or -SO2-. X 2arepresents a hydrocarbon group having 1 to 48 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is not selected from -O-, -S-, -CO-, -SO-, and -NR 11 It may be replaced by - or -SO2-. * -COO - represents the bonding site with the carbon atom of [In formula (bb), L A represents an alkanediyl group having 1 to 6 carbon atoms which may have a fluorine atom, or an aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a halogen atom or a perfluoroalkyl group having 1 to 4 carbon atoms. L B represents a single bond or an alkanediyl group having 1 to 6 carbon atoms, and -CH2- contained in the alkanediyl group is not selected from -O-, -S-, -CO-, -SO-, and -NR 11 It may be replaced by - or -SO2-. R A represents a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is not selected from -O-, -S-, -CO-, -SO-, and -NR 11 It may be replaced by - or -SO2-. * -COO - represents the bonding site with the carbon atom of X a and X b are preferably the same atom, and more preferably both are oxygen atoms. X 1a and X 2a Examples of the hydrocarbon group represented by the formula (I) include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group in which two or more of these are combined. These hydrocarbon groups may have a substituent. Furthermore, -CH2- contained in these hydrocarbon groups may be -O-, -S-, -CO-, -SO-, -NR 11 The number of carbon atoms in the hydrocarbon group refers to the number of carbon atoms in the hydrocarbon group that does not have a substituent and is not substituted. X 1aExamples of the aliphatic hydrocarbon group include chain hydrocarbon groups such as alkanetriyl groups, alicyclic hydrocarbon groups, and combinations thereof. Specific examples of the alkanetriyl group include a methine group, an ethanetriyl group, a propanetriyl group, a butanetriyl group, a pentanetriyl group, a hexanetriyl group, a heptanetriyl group, an octanetriyl group, a nonanetriyl group, a decanetriyl group, an undecanetriyl group, and a dodecanetriyl group. X 1a The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclobutanetriyl group, a cyclopentanetriyl group, a cyclohexanetriyl group, and a cyclooctanetriyl group. Examples of the polycyclic alicyclic hydrocarbon group include a norbornanetriyl group and an adamantanetriyl group. X 1a Examples of the aromatic hydrocarbon group include a benzenetriyl group, a naphthalenetriyl group, and an anthracentriyl group. X 1a When the above-mentioned groups are combined, the above-mentioned groups may contain groups with different valences (such as alkyl groups, alkanediyl groups, alkanetetrayl groups, cycloalkyl groups, cycloalkanediyl groups, and cycloalkanetetrayl groups). X 1a The hydrocarbon group represented by X has 1 to 24 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 16 carbon atoms, even more preferably 1 to 12 carbon atoms, even more preferably 1 to 8 carbon atoms, and even more preferably 1 to 6 carbon atoms. 1aThe hydrocarbon group represented by the formula (I) may further have one or more substituents, such as a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a combination thereof. Examples of the halogen atom, alkyl group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and combinations thereof include the same groups as those described above.
[0048] X 1a The hydrocarbon group represented by the formula (w1-3) is preferably an alkanetriyl group having 1 to 6 carbon atoms which may have a substituent or an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, more preferably an alkanetriyl group having 1 to 6 carbon atoms or a group represented by any of formulas (w1-1) to (w1-11), and even more preferably an alkanetriyl group having 1 to 6 carbon atoms, a polycyclic hydrocarbon group such as a group represented by formula (w1-1) or a group represented by formula (w1-3), or a monocyclic hydrocarbon group such as a group represented by formula (w1-2) or a group represented by formula (w1-6). TIFF2026026041000041.tif22154[Formula (w1-1) to formula (w1-11), The ring may have a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a combination thereof. * indicates a binding site, one of which is -COO - represents the bonding site with the carbon atom of X, and one of the remaining two is X. a represents the binding site with X b represents the binding site with X2a The number of carbon atoms in the hydrocarbon group represented by the formula (I) is preferably 2 to 48, more preferably 4 to 48, even more preferably 6 to 44, still more preferably 8 to 40, and even more preferably 10 to 38. The number of carbon atoms may be 1 to 24, preferably 1 to 18, more preferably 1 to 16, even more preferably 1 to 12, still more preferably 1 to 8, and even more preferably 1 to 6.
[0049] X 2a Examples of the substituent that the hydrocarbon group in the formula (I) may have include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, 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. Examples of the halogen atom, alkyl group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and combinations thereof include the same groups as those described above. X 2a The hydrocarbon group having 1 to 48 carbon atoms represented by the following formula may have one or more substituents. X 2a The substituent that the hydrocarbon group in the formula (I) may have is preferably a fluorine atom, an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. X 2a Examples of the hydrocarbon group in include linear or branched chain hydrocarbon groups (for example, alkanediyl groups, etc.), monocyclic or polycyclic alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be a combination of two or more of these groups. Specific examples thereof include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, and octane-1,8-diyl; and branched alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. monocyclic alicyclic hydrocarbon groups such as monocyclic cycloalkanediyl groups, such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; polycyclic alicyclic hydrocarbon groups such as polycyclic cycloalkanediyl groups, such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, and adamantane-2,6-diyl; and aromatic hydrocarbon groups such as phenylene, naphthylene, biphenylene, anthrylene, phenanthrylene, and binaphthylene.
[0050] X 2a When the hydrocarbon group in is a combined group as described above, the above groups may contain groups with different valences (such as alkyl groups, alkanetriyl groups, alkanetetrayl groups, cycloalkyl groups, cycloalkanetriyl groups, and cycloalkanetetrayl groups). Examples of the combined group include a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined, a group in which a chain hydrocarbon group and an aromatic hydrocarbon group are combined, and a group in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are combined. Specific examples include a group in which one or more alicyclic hydrocarbon groups are bonded to a chain hydrocarbon group (e.g., -chain hydrocarbon group-alicyclic hydrocarbon group, -chain hydrocarbon group-(alicyclic hydrocarbon group)2, etc.), a group in which one or more chain hydrocarbon groups are bonded to an alicyclic hydrocarbon group (e.g., -alicyclic hydrocarbon group-chain hydrocarbon group, -alicyclic hydrocarbon group-(chain hydrocarbon group)2, etc.), and a group in which one or more alicyclic hydrocarbon groups and chain hydrocarbon groups are bonded to a chain hydrocarbon group (e.g., -chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group, -chain hydrocarbon group-(alicyclic hydrocarbon group-chain hydrocarbon group)2, etc.). X 2a Examples of the hydrocarbon group in the formula (I) include a chain hydrocarbon group having 2 to 18 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-, and the alicyclic hydrocarbon group may have a substituent), or a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-) and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-) (which may have a substituent). X 2aThe hydrocarbon group in the formula (I) is a chain hydrocarbon group having 4 to 18 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent), or a combination of a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-) and an alicyclic hydrocarbon group having 3 to 16 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-) (which may have a substituent). X 2a The hydrocarbon group in the formula (I) is a chain hydrocarbon group having 6 to 14 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent), or a combination of a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-) and an alicyclic hydrocarbon group having 5 to 14 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-) (which may have a substituent). Specifically, X 2a Examples of the hydrocarbon group in the formula (I) include an alkanediyl group having 2 to 18 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-, and the alkanediyl group may have a substituent), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-, and the alicyclic hydrocarbon group may have a substituent), an alkanediyl group having 1 to 12 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-), and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR11 - or -SO2-) (which may have a substituent), or a group (which may have a substituent) consisting of an alkanediyl group having 1 to 12 carbon atoms (-CH2- in the alkanediyl group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and an alkyl group having 1 to 12 carbon atoms (-CH2- in the alkyl group may be replaced with -O- or -CO-). X 2a Examples of the hydrocarbon group in the formula (I) include an alkanediyl group having 4 to 18 carbon atoms (wherein -CH2- may be replaced by -O- or -CO-, and the alkanediyl group may have a substituent), an alkanediyl group having 1 to 12 carbon atoms (wherein -CH2- may be replaced by -O- or -CO-), and an alicyclic hydrocarbon group having 3 to 16 carbon atoms (wherein -CH2- may be replaced by -O-, -S-, -CO-, -SO-, -NR 11- or -SO2-) (the group may have a substituent), or a group (the group may have a substituent) consisting of an alkanediyl group having 1 to 12 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 16 carbon atoms, and an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), more preferably an alkanediyl group having 6 to 14 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-, and the alkanediyl group may have a substituent), and adamantanediyl group (-CH2- in the adamantanediyl group may be replaced with -O- or -CO-), which may have a substituent; or an alkanediyl group having 1 to 12 carbon atoms (-CH2- in the alkanediyl group may be replaced with -O- or -CO-), an adamantanediyl group, and an alkyl group having 1 to 12 carbon atoms (-CH2- in the alkyl group may be replaced with -O- or -CO-), which may have a substituent.
[0051] More specifically, X 2a is the formula (X 2 -1), a group represented by the formula (X 2 -2), a group represented by the formula (X 2 -3) or a group represented by the formula (X 2 -4) is preferred. TIFF2026026041000042.tif33158[expression(X 2 -1)~Formula(X 2 -4) Medium, R 1x , R 2x , R 3x , R 4x , R 5x and R 6xeach independently represents an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a group combining two or more of these groups, and -CH2- contained in the alkyl group and the alicyclic hydrocarbon group is not selected from -O-, -S-, -CO-, -SO-, -NR 11 The alkyl group and the alicyclic hydrocarbon group may have a substituent. * means either one is X a represents the binding site with X b represents the binding site with The combined group may be a combination of one alkyl group and one alicyclic hydrocarbon group described above, or two or more of either one or two or more of both. In this case, the number of carbon atoms in the combined group is 39 or less, and preferably 37 or less. Among them, R 1x , R 2x , R 3x , R 4x , R 5x and R 6x Examples of the alkyl group include an alkyl group having 1 to 6 carbon atoms (wherein -CH2- is optionally replaced by -O- or -CO-, and the alkyl group may have a substituent), an alicyclic hydrocarbon group having 5 to 12 carbon atoms (wherein -CH2- is optionally replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-, and the alicyclic hydrocarbon group may have a substituent.) or an alkyl group having 1 to 6 carbon atoms (-CH2- in the alkyl group may be replaced by -O- or -CO-) and an alicyclic hydrocarbon group having 5 to 12 carbon atoms (-CH2- in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR 11- or -SO2-) (which may have a substituent), and more preferably a methoxy group, an adamantyl group (wherein -CH2- in the adamantyl group may be replaced by -O- or -CO-, and the adamantyl group may have a substituent), or a group (wherein -CH2- in the alkyl group may be replaced by -O- or -CO-) combined with an adamantyl group (which may have a substituent).
[0052] The group represented by formula (aa) is more preferably a group represented by any one of the following formulas (aa1), (aa2), (aa3) and (aa4). TIFF2026026041000043.tif30136 [Formula (aa1) to formula (aa4), W 1a represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms. X a and X b Each of X independently represents -O- or -S-. a and X b is W 1a It bonds to the same carbon atom contained in R 1x , R 2x , R 3x , R 4x , R 5x and R 6x are each independently a group of the formula (X 2 -1), formula (X 2 -2), formula (X 2 -3) and the formula (X 2 -4) has the same meaning. * -COO - represents the bonding site with the carbon atom of In formulas (aa1) to (aa4), W 1aThe alicyclic hydrocarbon group is more preferably a group represented by formula (w1-1) to formula (w1-11), and even more preferably a polycyclic hydrocarbon group such as a group represented by formula (w1-1) or a group represented by formula (w1-3), or a monocyclic hydrocarbon group such as a group represented by formula (w1-2) or a group represented by formula (w1-6). In formula (bb), L A and L B Examples of the alkanediyl group having 1 to 6 carbon atoms include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and branched alkanediyl groups such as propane-1,2-diyl, 1-methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-methylbutane-1,4-diyl, and 2-methylbutane-1,4-diyl. The number of carbon atoms in the alkanediyl group is preferably 1 to 4, and more preferably 1 to 3. L A Examples of the alkanediyl group which may have a fluorine atom in the formula (I) include perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropanediyl group, a perfluorobutanediyl group, and a perfluoropentanediyl group. The -CH2- contained in the alkanediyl group can be substituted with -O-, -S-, -CO-, -SO-, or -NR 11 When -CH2- is replaced by - or -SO2-, the number of carbon atoms before the replacement is the total number of carbon atoms in the alkanediyl group. 11 - or -SO2- is replaced with a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced with -S-), an amino group (a group in which -CH2- in a methyl group is replaced with -NR 11-), oxy group (a group in which -CH2- in a methylene group is replaced with -O-), carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), thio group (a group in which -CH2- in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), peptide group (a group in which -CH2-CH2- in an ethylene group is replaced with -CO-NR 11 -), alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), alkylamino group (a group in which -CH2- at any position in an alkyl group is replaced with -NR 11 -), alkyl peptide group (wherein -CH2-CH2- at any position in the alkyl group is replaced by -CO-NR 11-), alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), alkoxycarbonyloxy group (a group in which -CH2-CH2-CH2- at any position in an alkyl group is replaced with -O-CO-O-), alkoxyalkyl group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), hydroxyalkyl group (a group in which -CH2- in a methyl group at any position in an alkyl group is replaced with -O-), alkanediyloxy group (alkanediyl an alkanediyloxycarbonyl group (an alkanediyl group in which -CH- at any position is replaced with -O-), an alkanediyloxycarbonyl group (an alkanediyl group in which -CH- at any position is replaced with -O-CO-), an alkanediylcarbonyl group (an alkanediyl group in which -CH- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (an alkanediyl group in which -CH- at any position is replaced with -CO-O-), an alkanediylthio group (an alkanediyl group in which -CH- at any position is replaced with -S-), an alkanediylsulfonyl group (an alkanediyl group in which -CH- at any position is replaced with -SO-), an alkanediylamino group (an alkanediyl group in which -CH- at any position is replaced with -NR 11 -), alkanediyl peptide group (wherein any -CH2-CH2- at any position in the alkanediyl group is replaced by -CO-NR 11 These substituted groups may be the same as the groups exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. L AExamples of the aromatic hydrocarbon group having 6 to 14 carbon atoms include aromatic hydrocarbon groups such as arylene groups such as 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 6 to 10, and more preferably 6. L A Examples of the halogen atom that may be contained in include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L A Examples of the perfluoroalkyl group having 1 to 4 carbon atoms that may be contained in the aryloxy group include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a nonafluorobutyl group. L A is preferably an alkanediyl group having 1 to 4 carbon atoms which may have a fluorine atom, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a halogen atom or a perfluoroalkyl group having 1 to 4 carbon atoms, and more preferably an alkanediyl group having 1 to 3 carbon atoms which may have a fluorine atom, or a phenylene group which may have a fluorine atom, an iodine atom, or a perfluoroalkyl group having 1 to 3 carbon atoms. L B is preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), and more preferably a single bond, a methylene group or an ethylene group. R A Examples of the hydrocarbon group in include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkyl groups, alkenyl groups, and alkynyl groups, and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, and groups formed by combining these. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, a 2-ethylhexyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 9, still more preferably 1 to 6, and even more preferably 1 to 4. Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. Examples of the alkynyl group include an ethynyl group, a propynyl group, an isopropynyl group, a butynyl group, an isobutynyl group, a tert-butynyl group, a pentynyl group, a hexynyl group, an octynyl group, and a nonynyl group. R A The -CH2- contained in the chain hydrocarbon group in 11 Examples of groups substituted for - or -SO2- include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkylsulfonyl group, and an alkylthio group. Examples of the alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkylsulfonyl group and alkylthio group include an alkoxy group having 1 to 17 carbon atoms, an alkoxycarbonyl group having 2 to 17 carbon atoms, an alkylcarbonyl group having 2 to 18 carbon atoms, an alkylcarbonyloxy group having 2 to 17 carbon atoms, an alkylsulfonyl group having 1 to 17 carbon atoms and an alkylthio group having 1 to 17 carbon atoms, and examples thereof include the same groups as those described above.
[0053] R AThe alicyclic hydrocarbon group in may be monocyclic, polycyclic, or spirocyclic, and may be saturated or unsaturated. Examples of monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl. Examples of polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl. R A The alicyclic hydrocarbon group and the -CH2- contained in the alicyclic hydrocarbon group are -O-, -S-, -CO-, -SO-, -NR 11 Specific examples of the group substituted with - or -SO2- include groups represented by the above formulae (y1) to (y71). The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 36, more preferably 3 to 24, even more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12. R A Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The aromatic hydrocarbon group preferably has 6 to 36 carbon atoms, more preferably 6 to 24 carbon atoms, even more preferably 6 to 18 carbon atoms, still more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms. R A When the above-mentioned groups are combined, the above-mentioned groups may contain groups with different valences (alkanediyl group, alkanetriyl group, cycloalkanediyl group, cycloalkanetriyl group, etc.). Groups formed by combination include groups combining an aromatic hydrocarbon group with a chain hydrocarbon group (e.g., aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*), groups combining an alicyclic hydrocarbon group with a chain hydrocarbon group (e.g., alicyclic hydrocarbon group-alkanediyl group-*, alkyl group-alicyclic hydrocarbon group-*), and groups combining an aromatic hydrocarbon group with a alicyclic hydrocarbon group (e.g., aromatic hydrocarbon group-alicyclic hydrocarbon group-*, alicyclic hydrocarbon group-aromatic hydrocarbon group-*). * represents a bonding site. The aromatic hydrocarbon group -alkanediyl group-* includes aralkyl groups such as benzyl group and phenethyl group. Examples of the alkyl group-aromatic hydrocarbon group-* include a tolyl group, a xylyl group, and a cumenyl group. Examples of the alicyclic hydrocarbon group -alkanediyl group-* include cycloalkylalkyl groups such as a cyclohexylmethyl group, a cyclohexylethyl group, a 1-(adamantan-1-yl)methyl group, and a 1-(adamantan-1-yl)-1-methylethyl group. Examples of the alkyl group-alicyclic hydrocarbon group-* include cycloalkyl groups having an alkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, and a 2-alkyladamantan-2-yl group. Examples of the aromatic hydrocarbon group-alicyclic hydrocarbon group-* include a phenyladamantyl group. Examples of the alicyclic hydrocarbon group-aromatic hydrocarbon group-* include an adamantylphenyl group. In the group formed by combining these, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. B may be bound to R A The -CH2- contained in the hydrocarbon group in 11In addition to the groups mentioned above, the groups substituted with - or -SO2- also include a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, an aromatic hydrocarbon group-carbonyloxy group, and a group formed by combining two or more of these groups. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 17 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 17 carbon atoms, such as a benzoyloxy group. The -CH2- contained in the hydrocarbon group can be -O-, -S-, -SO2-, -SO-, or -NR 11 When the hydrocarbon group is substituted with - or -CO-, the total number of carbon atoms in the hydrocarbon group is the number of carbon atoms before the substitution. R A The substituents that the hydrocarbon group may have include a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group is not limited to -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-). Examples of the halogen atom include the same groups as those mentioned above. Examples of the alkyl group having 1 to 12 carbon atoms include the same groups as those mentioned above. Examples of groups in which -CH2- in an alkyl group is replaced with -O- or -CO- include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, and an alkylcarbonyloxy group. Examples of the alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, and alkylcarbonyloxy group include alkoxy groups having 1 to 11 carbon atoms, alkoxycarbonyl groups having 2 to 11 carbon atoms, alkylcarbonyl groups having 2 to 12 carbon atoms, and alkylcarbonyloxy groups having 2 to 11 carbon atoms, and include, for example, the same groups as those described above. R A The hydrocarbon group in may have one or more substituents. R A The hydrocarbon group in the formula (I) is an alkyl group having 1 to 12 carbon atoms which may have a substituent (provided that -CH2- contained in the alkyl group is not -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2-) or a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (provided that -CH2- contained in the cyclic hydrocarbon group is not replaced by -O-, -S-, -CO-, -SO-, -NR2-, 11 - or -SO2-), and a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms or a perfluoroalkyl group having 1 to 6 carbon atoms (provided that -CH2- contained in the cyclic hydrocarbon group is not an integer of 0-1, and may be replaced by -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2- may be substituted.) is more preferred. Examples of the cyclic hydrocarbon group include cyclic hydrocarbon groups such as monocyclic or polycyclic alicyclic hydrocarbon groups having 3 to 18 carbon atoms and aromatic hydrocarbon groups having 6 to 18 carbon atoms, or combinations of these groups. Examples of the alicyclic hydrocarbon group, aromatic hydrocarbon group, and combined group include the same groups as those described above. In the group formed by the combination, two or more types of alicyclic hydrocarbon groups and two or more types of aromatic hydrocarbon groups may be combined. B may be bound to R Aa cyclic hydrocarbon group having 3 to 18 carbon atoms (the cyclic hydrocarbon group may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms, and -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2- may be replaced. an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or a perfluoroalkyl group having 1 to 4 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group is not limited to -O-, -S-, -CO-, -SO-, -NR 11 - or -SO2- may be replaced), or It is preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or a perfluoroalkyl group having 1 to 4 carbon atoms.
[0054] The group represented by formula (bb) is more preferably a group represented by formula (bb1). TIFF2026026041000044.tif1577[In formula (bb1), L A and L B has the same meaning as formula (bb). W 2a represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, which may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group, and -CH2- contained in the alicyclic hydrocarbon group is selected from -O-, -S-, -CO-, -SO-, -NR 11 It may be replaced by - or -SO2-. * -COO - represents the bonding site with the carbon atom of In equation (bb1), W 2a is an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or a perfluoroalkyl group having 1 to 4 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group is not limited to -O-, -CO-, -S-, -SO-, -NR11 - or -SO2- may be substituted.) is more preferred. In equation (bb1), W 2a The alicyclic hydrocarbon group is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, or the following groups (the bonding site may be at any position): TIFF2026026041000045.tif1687 Examples of the carboxylate anion in the carboxylate salt represented by formula (I) include the carboxylate anions shown below. TIFF2026026041000046.tif241163
[0055] TIFF2026026041000047.tif243163
[0056] TIFF2026026041000048.tif228164
[0057] Specific examples of the carboxylate (I) include salts of any combination of the above-mentioned cations and anions. Specific examples of the carboxylate (I) are shown in the table below. In the table below, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation, and "~" indicates that the carboxylate (I) corresponds to the anion (I). For example, carboxylate (I-1) means a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-1), and represents the carboxylate shown below. Furthermore, carboxylate (I-2) represents a salt consisting of an anion represented by formula (Ia-2) and a cation represented by formula (Ic-1), and carboxylate (I-101) represents a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-2). TIFF2026026041000049.tif39115 [Table 1] TIFF2026026041000051.tif249161 TIFF2026026041000052.tif177155
[0058] Among these, as the carboxylate (I), a salt obtained by combining an anion represented by any one of formulas (Ia-1) to (Ia-5), (Ia-10) to (Ia-21), (Ia-57) to (Ia-66), and (Ia-94) with a cation represented by any one of formulas (Ic-1) to (Ic-105) is preferred.
[0059] <Method for producing carboxylate (I)> The carboxylate (I) can be produced by reacting a salt represented by formula (Ia) with a salt represented by formula (Ib) in a solvent. TIFF2026026041000053.tif67165 [wherein all symbols have the same meanings as defined above.] X x represents a chlorine atom, a bromine atom, or an iodine atom. R A , R B and R C each independently represents a hydrocarbon group having 1 to 12 carbon atoms, or R A , R B and R C may combine to form an aromatic ring. D represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms.] Examples of solvents used in this reaction include chloroform, acetonitrile, and ion-exchanged water. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.
[0060] The salt represented by formula (Ib) can be synthesized with reference to the methods described in JP-A Nos. 2011-39502 and 2014-88367, and examples thereof include salts represented by the following formulas. TIFF2026026041000054.tif124164
[0061] The salt represented by formula (Ia) can be produced by reacting the salt represented by formula (Ic) with the compound represented by formula (I-d1) in a solvent in the presence of a catalyst, and optionally treating with an acid. TIFF2026026041000055.tif67170 [wherein all symbols have the same meanings as above. R aa is a fluorine atom or -(CO) aa represents —OH, and aa represents 0 or 1. 1’ is A 1 From -(CO) aa represents a group excluding -O-.] Examples of the catalyst include potassium carbonate, sodium hydride, carbonyldiimidazole, and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. Examples of the solvent include chloroform, monochlorobenzene, acetonitrile, and water. The acid includes hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, and the like. The reaction temperature is usually 15° C. to 100° C., and the reaction time is usually 0.5 to 24 hours.
[0062] Examples of the salt represented by formula (Ic) include salts represented by the following formula, which are readily available on the market. TIFF2026026041000056.tif125162
[0063] Examples of the compound represented by formula (I-d1) include the compounds represented by the following formulas, which are readily available on the market. TIFF2026026041000057.tif155141
[0064] [Carboxylic Acid Generator] The carboxylic acid generator of the present invention is an acid generator containing a carboxylic acid salt (I). The carboxylic acid salt (I) of the present invention can function as an acid generator or a quencher in a resist composition. When the carboxylic acid salt (I) is used as an acid generator or a quencher in a resist composition, the acid generator or quencher may contain only one type of carboxylic acid salt (I), or two or more types of carboxylic acid salts (I). Furthermore, as will be described later, the acid generator of the present invention may further contain an acid generator other than the carboxylate (I) that is known in the resist field (hereinafter, this may be referred to as "acid generator (B)" or "compound (B)") and / or a carboxylic acid generator other than the carboxylate (I) that is known in the resist field. The acid generator (B) may be used alone or in combination of two or more. When the carboxylic acid generator of the present invention contains an acid generator (B) or the like, the ratio of the content of the carboxylic acid salt (I) to the content of the acid generator (B) or the like (mass ratio; carboxylic acid salt (I):acid generator (B)) or the like is usually 1:99 to 100:0, preferably 1:99 to 99:1, more preferably 2:98 to 98:2, and even more preferably 5:95 to 95:5.
[0065] [Resist Composition] The resist composition of the present invention may contain, in addition to the carboxylic acid generator containing the carboxylate (I) of the present invention, an acid generator other than the carboxylic acid generator (hereinafter sometimes referred to as "acid generator (B)" or "compound (B)"). The resist composition of the present invention may further contain a resin. Examples of the resin include a resin containing a structural unit having an acid labile group (hereinafter sometimes referred to as "resin (A)") and / or a resin other than resin (A). Here, the "acid labile group" refers to a group that has a leaving group and that is eliminated by contact with acid to form a hydrophilic group (e.g., a hydroxy group or a carboxy group). The resist composition of the present invention preferably further contains a quencher (hereinafter sometimes referred to as "quencher (C)") and / or a solvent (hereinafter sometimes referred to as "solvent (E)"). In the resist composition of the present invention, the content of the carboxylate (I) relative to the solid content of the resist composition is, for example, 0.1 mass % or more and 99.9 mass % or less, preferably 0.1 mass % or more and 35 mass % or less, more preferably 0.5 mass % or more and 30 mass % or less, and even more preferably 1 mass % or more and 25 mass % or less.
[0066] <Acid generator (B)> The acid generator (B) may be either a nonionic compound or an ionic compound. Examples of nonionic compounds include sulfonate esters (e.g., 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxyketone, diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfone, ketosulfone, sulfonyldiazomethane), etc. Examples of ionic compounds include onium salts containing onium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts, iodonium salts). Examples of anions of onium salts include sulfonate anions, sulfonylimide anions, sulfonylmethide anions, and carboxylate anions. The acid generator (B) may be a part of the structural unit of the resin contained in the resist composition of the present invention, like the structural unit (a7) described below.
[0067] The acid generator (B) may be a compound that generates an acid when exposed to radiation, as described in JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, JP-A-63-146029, U.S. Pat. No. 3,779,778, U.S. Pat. No. 3,849,137, German Patent No. 3,914,407, or European Patent No. 126,712. Compounds produced by known methods may also be used. The acid generator (B) may be used alone or in combination of two or more. Compound (B) may be an acid generator having an acid labile group. For example, the compound or resin that serves as the acid generator may contain a partial structure that forms an acid labile group, and the acid labile group preferably contains group (1) or group (2) described below. When the resist composition of the present invention contains a compound having an acid labile group, it does not necessarily need to contain a resin that contains a structural unit having an acid labile group.
[0068] Preferred embodiments of the acid generator (B) include a salt represented by formula (B1) (hereinafter sometimes referred to as "salt (B1)" or "acid generator (B1)") and a salt represented by formula (B2) (hereinafter sometimes referred to as "salt (B2)" or "acid generator (B2)"). JPEG2026026041000058.jpg1395 [In formula (B1), all symbols have the same meanings as defined above.]
[0069] L b1 The (nb1+1)-valent hydrocarbon group is a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, a monovalent aromatic hydrocarbon group, or a monovalent group that combines two or more of these groups, from which nb1 hydrogen atoms have been removed to form one or more L b2 The hydrocarbon group may have 1 to 48 carbon atoms, preferably 1 to 42, more preferably 1 to 36, even more preferably 1 to 30, still more preferably 1 to 24, even more preferably 1 to 18, and even more preferably 1 to 10. Examples of the chain hydrocarbon group include groups in which nb hydrogen atoms have been removed from an alkyl group or an alkenyl group. The alkyl group may be linear or branched, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, and heptadecyl groups. Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 36, more preferably 1 to 24, even more preferably 1 to 20, still more preferably 1 to 18, even more preferably 1 to 12, and even more preferably 1 to 10. Examples of the alicyclic hydrocarbon group include groups in which nb hydrogen atoms have been removed 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 polycyclic cycloalkyl groups include cycloalkyl groups having a bridged structure, cycloalkyl groups in which two or more rings are fused, and cycloalkyl groups in which two rings are bonded via a spiro bond. Examples of cycloalkyl groups having a bridged structure include a norbornyl group and an adamantyl group. Examples of cycloalkyl groups in which two or more rings are fused include a bicyclo[4.4.0]decanyl group and a steroid group (steroid skeleton). Examples of cycloalkyl groups in which two rings are bonded via a spiro bond include spirocyclic cycloalkyl groups in which one cycloalkyl group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group is bonded via a spiro bond to a cycloalkyl group having 5 to 8 carbon atoms. A double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group. More specifically, alicyclic hydrocarbon groups represented by the following formulas are included. TIFF2026026041000059.tif26170 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, even more preferably 3 to 18, still more preferably 3 to 12, even more preferably 3 to 10, and still 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, even more preferably 6 to 18, still more preferably 6 to 12, and even more preferably 7 to 12. Examples of aromatic hydrocarbon groups include groups in which nb1 hydrogen atoms have been removed from an aryl group, such as a phenyl group, naphthyl group, anthryl group, biphenyl group, and fluorenyl group. More specifically, aromatic hydrocarbon groups represented by the following formulas are included. TIFF2026026041000060.tif1186 The number of carbon atoms in the aromatic hydrocarbon group is preferably 4 to 24, more preferably 4 to 20, even more preferably 4 to 18, still more preferably 5 to 14, even more preferably 5 to 10, and even more preferably 6 to 10. Examples of the group combining two or more groups selected from the group consisting of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group include a group combining the above-mentioned chain hydrocarbon group with the above-mentioned alicyclic hydrocarbon group, a group combining the above-mentioned chain hydrocarbon group with the above-mentioned aromatic hydrocarbon group, a group combining the above-mentioned alicyclic hydrocarbon group with the above-mentioned aromatic hydrocarbon group, and a group combining the above-mentioned chain hydrocarbon group with the above-mentioned alicyclic hydrocarbon group and the above-mentioned aromatic hydrocarbon group. The group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group may be a fused ring. L b1When -CH2- in the hydrocarbon group is replaced with -O-, -CO-, -S-, -SO- or -SO2-, the number of carbon atoms before replacement is regarded as the number of carbon atoms of the hydrocarbon group. L b1 Among these hydrocarbon groups, examples of groups in which -CH2- in the chain hydrocarbon group is replaced with -O-, -CO-, -S-, -SO- or -SO2- include a hydroxy group, a carboxy group, a thiol group, an oxy group, a carbonyl group, a thio group, a sulfonyl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an alkoxyalkoxy group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediyloxycarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, a cycloalkoxy group, a cycloalkylalkoxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and groups in which two or more of these groups are combined. These substituted groups include the same groups as those exemplified in this specification, within the limits permitted by the upper limit of the number of carbon atoms. L b1 Among these hydrocarbon groups, examples of groups in which -CH2- contained in an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these is replaced with -O-, -CO-, -S-, -SO-, or -SO2- include groups containing structures such as cyclic ether, cyclic ketone, cyclic ester (lactone), cyclic thioether, cyclic acetal, cyclic sulfonate ester (sultone), etc., and groups derived from a furan ring, thiophene ring, etc. Specific examples include the same groups as exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. L b2 Examples of the divalent hydrocarbon group include a divalent chain hydrocarbon group, a divalent alicyclic hydrocarbon group, a divalent aromatic hydrocarbon group, and a group combining two or more of these groups. A monovalent hydrocarbon group can be obtained by removing one hydrogen atom to form Y b1 Examples of such groups include groups that bond to the following: L b2The divalent chain hydrocarbon group, divalent alicyclic hydrocarbon group, divalent aromatic hydrocarbon group, and divalent group formed by combining two or more of these groups are each, within the range permitted by the upper limit of the number of carbon atoms, L b1 Examples of the monovalent hydrocarbon group include a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, a monovalent aromatic hydrocarbon group, and a monovalent group obtained by combining two or more of these groups and removing one hydrogen atom from them. L b1 and L b2 Examples of the substituent that the hydrocarbon group may have include a halogen atom, a cyano group, and a nitro group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L b1 and L b2 When L is a group in which an alicyclic hydrocarbon group or an aromatic hydrocarbon group is combined with a chain hydrocarbon group, the chain hydrocarbon group may be regarded as a substituent that the alicyclic hydrocarbon group or the aromatic hydrocarbon group has. b1 and L b2 The -CH2- of the chain hydrocarbon group contained in the hydrocarbon group is replaced by -O-, -CO-, -S-, -SO- or -SO2-, thereby forming L b1 and L b2 The hydrocarbon group may substantially have a substituent such as a hydroxy group, a carboxy group, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a thiol group, an alkylthio group, or an alkylsulfonyl group. Y b1 Examples of the cyclic hydrocarbon group include an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are combined. Y b1 The alicyclic hydrocarbon group and the aromatic hydrocarbon group are, respectively, L b1 Examples of the alicyclic hydrocarbon groups and aromatic hydrocarbon groups include those similar to those exemplified in 1., and when they have no substituent, they may be monovalent alicyclic hydrocarbon groups and aromatic hydrocarbon groups. Y b1Examples of the substituent that the methyl group and cyclic hydrocarbon group may have include a halogen atom, a cyano group, a nitro group, or a hydrocarbon group having 1 to 18 carbon atoms that may have a halogen atom, a cyano group, or a nitro group (-CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-). Y b1 The number of carbon atoms in the hydrocarbon group that the methyl group and the cyclic hydrocarbon group may have is b1 The carbon number of the methyl group and the cyclic hydrocarbon group is not included in the carbon number of the methyl group and the cyclic hydrocarbon group. Y b1 Examples of the hydrocarbon group having 1 to 18 carbon atoms that may be substituted on the methyl group and cyclic hydrocarbon group include chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining these groups. Examples of the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and groups combining two or more of these groups include, within the range permitted by the upper limit of the number of carbon atoms, L b1 Examples of the hydrocarbon groups include the chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups in which two or more of these groups are combined, as exemplified above. Y b1 Examples of the methyl group and the hydrocarbon group having 1 to 18 carbon atoms that may have a substituent, in which -CH2- is replaced by -O-, -S-, -CO-, -SO- or -SO2-, are, within the range permitted by the upper limit of the number of carbon atoms, L b1 Examples of the hydrocarbon group include the same groups as those exemplified above in which -CH2- in the hydrocarbon group is replaced with -O-, -S-, -CO-, -SO- or -SO2-. b1 The hydrocarbon group having 1 to 18 carbon atoms that the methyl group and cyclic hydrocarbon group may have as a substituent may constitute a protecting group or leaving group (acid labile group or base labile group) commonly used in the art.
[0070] The anion in the salt represented by formula (B1) is preferably an anion represented by the following formula (B1-A1) (hereinafter, may be referred to as "anion (B1-A1)") or an anion represented by formula (B1-A2) (hereinafter, may be referred to as "anion (B1-A2)"). TIFF2026026041000061.tif29126[In formula (B1-A1), L b2 and Y b1 has the same meaning as in 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 an integer of 0 to 6. When z1 is 2 or more, the groups in the parentheses may be the same or different. X 1 represents -O-CO-, -CO-O-, -O-CO-O- or -O-. L b3 represents a single bond or an (nb2+1)-valent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-. nb2 represents an integer of 1 to 3. When nb2 is 2 or greater, the groups in the parentheses may be the same or different.] Q b1 , Q b2 , Q b3 and Q b4 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Q b1 , Q b2 , Q b3 and Q b4 Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, and a perfluorohexyl group. Q b1 and Q b2 Q b1 and Qb2 At least one of the groups preferably contains a fluorine atom or a perfluoroalkyl group, more preferably a fluorine atom or a perfluoroalkyl group, even more preferably a fluorine atom or a trifluoromethyl group, and even more preferably both are fluorine atoms. Q b3 and Q b4 are each preferably independently a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, and Q b3 is preferably a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, and Q b4 is preferably a hydrogen atom or a fluorine atom. z1 is preferably an integer of 0 to 3, and more preferably 0, 1 or 2. X 1 is preferably —O—CO— or —CO—O—.
[0071] L b3 As the hydrocarbon group in the formula (B1), within the range permitted by the upper limit of the number of carbon atoms, b1 The same hydrocarbon groups as those exemplified above can be mentioned. In formula (B1-A1), L b3is preferably a single bond, an optionally substituted chain hydrocarbon group of 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an optionally substituted alicyclic hydrocarbon group of 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO- or -SO2-), an optionally substituted aromatic hydrocarbon group of 6 to 10 carbon atoms (-CH2- contained in the aromatic hydrocarbon group may be replaced with -O- or -S-), or a group comprising a combination of two or more of these groups, and more preferably a single bond, an optionally substituted chain hydrocarbon group of 1 to 6 carbon atoms, or a group represented by the following formula (Lb3-1): When -CH2- in the chain hydrocarbon group is replaced with -O- or -CO-, the number of -CH2- in the chain hydrocarbon group replaced with -O- or -CO- is preferably 1 to 4, and it is preferred that one -CH2-CH2- in the chain hydrocarbon group is replaced with -O-CO- or -CO-O-, or one -CH2-CH2-CH2- in the chain hydrocarbon group is replaced with -O-CO-O-. TIFF2026026041000062.tif1580[In formula (Lb3-1), nb2 has the same meaning as in formula (B1-A1). L b31 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms, and -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and the chain hydrocarbon group may have a substituent. W b3 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-, and -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a substituent. * and ** represent binding sites, * represents X 1 represents the binding site with In formula (Lb3-1), L b31The chain hydrocarbon group of L is as long as the upper limit of the carbon number allows. b1 Examples of the chain hydrocarbon groups include the same groups as those exemplified above. In formula (Lb3-1), W b3 The alicyclic hydrocarbon group and aromatic hydrocarbon group of L are as long as the upper limit of the carbon number allows. b1 Examples of the alicyclic hydrocarbon groups and aromatic hydrocarbon groups are the same as those exemplified above. In formula (Lb3-1), L b31 The substituents which the chain hydrocarbon group of W may have and b3 The substituents that the alicyclic hydrocarbon group and aromatic hydrocarbon group may have are b1 Examples of the substituent that the hydrocarbon group may have include the same groups as the substituents exemplified above. L b31 is preferably a single bond or an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-). In formula (Lb3-1), W b3 Examples of the alicyclic hydrocarbon group and aromatic hydrocarbon group include the alicyclic hydrocarbon group and aromatic hydrocarbon group shown below. In the alicyclic hydrocarbon group and aromatic hydrocarbon group shown below, * and ** represent a bonding site, * represents X 1 or L b31 represents a bonding site with L, and ** represents a hydrogen atom, a substituent, or L b2 represents a binding site with at least one ** b2 represents a bonding site with. In the alicyclic hydrocarbon groups represented below, -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-. When -CH2- contained in the alicyclic hydrocarbon group is replaced with -O-, -S-, -CO-, -SO-, or -SO2-, it is preferable that an ether ring, ester ring (lactone ring), carbonate ester ring, sulfonate ester ring (sultone ring), or acetal ring is formed. In TIFF2026026041000063.tif37164 formula (B1-A1), L b2is preferably a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), and is preferably a single bond, -O-, -O-CO-, -CO-O-, -O-CO-O- or -L b21 -X 2 -L b22 -**(L b21 and L b22 One of X represents a chain hydrocarbon group having at least 1 to 6 carbon atoms, and the other represents a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms. 2 represents -O-, -CO-O-, -O-CO- or -O-CO-O-. * and ** represent bonding sites, and ** represents Y b1 represents the binding site with L b21 , X 2 and L b22 The total number of carbon atoms is 12 or less. In formula (B1-A1), Y b1 is preferably a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (-CH2- in the cyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, -SO-, or -SO2-), more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (-CH2- in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, -SO-, or -SO2-) or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and even more preferably an alicyclic hydrocarbon group having 3 to 16 carbon atoms which may have a substituent (-CH2- in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, -SO-, or -SO2-) or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. Specifically, groups represented by the following formulae (Y1) to (Y36) are more preferred. In formulas (Y1) to (Y36), R Yb is a hydrogen atom or Y b1 Among the substituents that the cyclic hydrocarbon group may have, R represents an alkyl group having 1 to 4 carbon atoms. Yc is a hydrogen atom or Y b1 represents a substituent that the cyclic hydrocarbon group of the formula (I) may have, and * represents a substituent that the cyclic hydrocarbon group of the formula (I) may have,b2 The alicyclic hydrocarbon groups and aromatic hydrocarbon groups represented by the following formulae (Y1) to (Y36) may have other substituents, although these are not specifically shown in the following formulae. TIFF2026026041000064.tif84160
[0072] The anion represented by formula (B1-A1) is preferably an anion represented by formula (B1-A1-1) to formula (B1-A1-85) (hereinafter, sometimes referred to as "anion (B1-A1-1)" depending on the formula number), and more preferably an anion represented by any of formulas (B1-A1-1) to (B1-A1-4), (B1-A1-9), (B1-A1-10), (B1-A1-24) to (B1-A1-33), (B1-A1-36) to (B1-A1-40), and (B1-A1-47) to (B1-A1-85). TIFF2026026041000065.tif216161
[0073] TIFF2026026041000066.tif249150
[0074] TIFF2026026041000067.tif254157
[0075] where R i2 ~R i7 are each independently, for example, an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group. i8 is, for example, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a group formed by combining these, more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. A41 is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Q b1 and Q b2 has the same meaning as above. Specific examples of the anion represented by formula (B1-A1) include the anions described in JP-A-2010-204646.
[0076] Preferred anions represented by formula (B1-A1) include those represented by formulas (B1a-1) to (B1a-72). Of these, anions represented by any of formulas (B1a-1) to (B1a-4), (B1a-7) to (B1a-11), (B1a-14) to (B1a-30), and (B1a-35) to (B1a-72) are preferred. TIFF2026026041000068.tif182158
[0077] TIFF2026026041000069.tif252162
[0078] TIFF2026026041000070.tif90165
[0079] The anion represented by formula (B1-A2) is represented by the following formula: TIFF2026026041000071.tif24100[In formula (B1-A2), L b2 and Y b1 has the same meaning as in formula (B1). R b1 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and one --CH.sub.2-- contained in the alkyl group may be replaced with --O-- or --CO--. nb4 represents an integer of 1 to 5. When nb4 is 2 or greater, the groups in the parentheses may be the same or different. nb3 represents an integer of 0 to 4. When nb3 is 2 or more, a plurality of R b1 may be the same or different from each other. However, 1≦nb4+nb3≦5 is satisfied.
[0080] In formula (B1-A2), L b2 and Y b1Examples of the cyclic hydrocarbon group include, within the upper limit of the carbon number, L in formula (B1). b2 and Y b1 Examples of the cyclic hydrocarbon group are the same as those of L. b2 hydrocarbon group, Y b1 The substituents that the methyl group and the cyclic hydrocarbon group may have are also defined as follows: b2 hydrocarbon group, Y b1 Examples of the substituents that the methyl group and cyclic hydrocarbon group may have are the same as those listed above. These hydrocarbon groups, methyl groups and cyclic hydrocarbon groups may have one or more substituents. L b2 is preferably a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), and more preferably -CO-OL b41 -(L b41 is a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms, and -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-. * is SO3 - represents the bonding site with the benzene ring to which L is attached. b41 is preferably a single bond or a chain hydrocarbon group having 1 to 3 carbon atoms. ) and even more preferably *-CO-O-. Y b1 is preferably a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (-CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, -SO- or -SO2-), more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, -SO- or -SO2-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and even more preferably Y in formula (B1-A1) b1 or L b1Specifically, the groups represented by the above formulae (Y1) to (Y36) are preferred, and the groups represented by the above formulae (Y1) to (Y19) are more preferred. Y b1 The substituents that the cyclic hydrocarbon group may have are preferably a halogen atom or an alkyl group having 1 to 6 carbon atoms (wherein -CH2- in the alkyl group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-), more preferably a fluorine atom, an iodine atom or an alkyl group having 1 to 4 carbon atoms (wherein -CH2- in the alkyl group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-), even more preferably a fluorine atom, an iodine atom, a hydroxy group, an alkoxy group having 1 to 3 carbon atoms or an alkyl group having 1 to 4 carbon atoms, and even more preferably a fluorine atom, an iodine atom, a hydroxy group or an alkyl group having 1 to 4 carbon atoms. b1 The substituent of may constitute a protecting group or leaving group (acid labile group or base labile group) commonly used in the art.
[0081] In formula (B1-A2), nb4 is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, even more preferably 1 or 2, and even more preferably 2. When nb4 is 1 or 2, -L b2 -Y b1 The bond position of SO3 - The following structure, which is substituted at the m-position of the benzene ring relative to the bonding position of TIFF2026026041000072.tif26106 [In the above formula, L b2 , Y b1 , R b1 , nb3 has the same meaning as in formula (B1-A2). In formula (B1-A2), when nb4 is 2 or more, a plurality of L b2 and Y b1 are preferably the same group.
[0082] R b1Examples of the alkyl group having 1 to 6 carbon atoms include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 4, and more preferably 1 to 3. R b1 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of groups in which -CH- in an alkyl group is replaced with -O- or -CO- include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an oxy group, a carbonyl group, etc. These substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. R b1 are each independently preferably a halogen atom or an alkyl group having 1 to 4 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), more preferably a fluorine atom, an iodine atom or an alkyl group having 1 to 3 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), and further preferably a fluorine atom, an iodine atom, a hydroxy group, a methoxy group or a methyl group. nb3 is an integer of 0 to 4 (i.e., nb3-1 is an integer of 0 to 3), preferably an integer of 0 to 3, and more preferably an integer of 0 to 2. In one embodiment, nb3 is preferably 0. In another embodiment, nb3 is preferably 1 or 2. When nb3 is 1, R b1 is preferably a halogen atom, and R b1 is more preferably a fluorine atom or an iodine atom. When nb3 is 2, R b1 Preferably, one of R is a halogen atom and the other is a halogen atom or an alkyl group having 1 to 4 carbon atoms, b1 It is more preferable that one of the groups is a fluorine atom or an iodine atom, and the other is a fluorine atom, an iodine atom, or an alkyl group having 1 to 3 carbon atoms.
[0083] Examples of the anion represented by formula (B1-A2) include the following anions. Among them, the anions represented by formulas (B2a-1) to (B2a-32) are preferred, and the anions represented by formulas (B2a-1) to (B2a-11) and (B2a-16) to (B2a-32) are more preferred. The following anions are preferred in the case where some R b1 is omitted, and may contain substituents not shown. TIFF2026026041000073.tif173159
[0084] Examples of the acid generator (B2) include salts represented by the following formula: TIFF2026026041000074.tif1191 [In formula (B2), all symbols have the same meanings as defined above.] In formula (B2), L b2’ and Y b1’ Examples of the hydrocarbon group, cyclic hydrocarbon group and their substituents are L in formula (B1-A1). b2 and Y b1 The same groups as those shown below can be mentioned. L b2 ' is a single bond, *-L b23 -, *-L b23 -X 2 -or*-L b23 -X 2 -W 2 -X 3 -(L b23 represents a chain hydrocarbon group having 1 to 6 carbon atoms which may contain a fluorine atom. 2 and X 3 each independently represents -O-, -CO-O-, -O-CO-, -O-CO-O- or -O-. W 2 represents an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O- or -CO-. * represents a bonding site with SO2. ) is preferred. Y b1is preferably a fluorine atom-containing methyl group or a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (-CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, -SO- or -SO2-), and more preferably a trifluoromethyl group, an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO- or -SO2-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. Specifically, it is more preferably a trifluoromethyl group or a group represented by formulae (Y1) to (Y36) in formula (B1-A1). In the anion of the salt represented by formula (B2), two SO2-L b2 '-Y b1 When "A" and "B" are taken together to form a ring, examples of the anion include an anion represented by formula (B2'). TIFF2026026041000075.tif22113[In formula (B2'), A 1 , Y b1’ , L b2’ and nb5 have the same meaning as in formula (B2). W b4 represents a disulfonylimide ring or disulfonylmide ring having 2 to 12 carbon atoms which may have a fluorine atom.] W b4 The disulfonylimide ring or disulfonylmide ring may have 3 to 12 carbon atoms, preferably 3 to 6 carbon atoms, and the hydrogen atom of the methylene group contained in the ring is preferably substituted with a fluorine atom.
[0085] Examples of the anion of the salt represented by formula (B2) include the following: Among these, the anions represented by formulae (B3a-1), (B3a-2), and (B3a-12) to (B3a-14) are preferred. TIFF2026026041000076.tif175165
[0086] In another embodiment of the acid generator (B), a salt in which the sulfonate anion in the salt represented by formula (B1) is replaced with a carboxylate anion is also preferably used as the acid generator (B). Examples of carboxylate anions include the following: However, the acid generator (B) having a carboxylate anion does not include the carboxylate salt of formula (I). TIFF2026026041000077.tif40156
[0087] Z1 + and Z2 + Examples of the organic cation include organic onium cations, organic sulfonium cations, organic iodonium cations, organic ammonium cations, benzothiazolium cations, and organic phosphonium cations. Among these, organic sulfonium cations and organic iodonium cations are preferred, and arylsulfonium cations or aryl iodonium cations are more preferred. Specific examples include cations represented by any of formulas (b2-1) to (b2-5) (hereinafter, sometimes referred to as "cation (b2-1)" depending on the formula number). TIFF2026026041000078.tif84159[Formula (b2-1) to (b2-5), R b4 ~R b6 each independently represent a chain hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms, a hydrogen atom contained in the chain hydrocarbon group may be substituted with a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, a hydrogen atom contained in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a glycidyloxy group, and a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b4 and R b5and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b7 and R b8 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. m7 and n8 each independently represent an integer of 0 to 5; When m7 is 2 or more, multiple R b7 may be the same or different, and when n8 is 2 or more, multiple R b8 may be the same or different. R b9 and R b10 each independently represents a chain hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b11 represents a hydrogen atom, a chain hydrocarbon group having 1 to 36 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. R b12 represents a chain hydrocarbon group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 12 carbon atoms or an alkylcarbonyloxy group having 1 to 12 carbon atoms. R b11 and R b12 and may be bonded to each other to form a ring including the -CH-CO- to which they are bonded, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. R b13 ~R b18 and Rb21 ~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 may be bonded to each other to form a ring containing a sulfur atom together with the benzene ring to which they are attached, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. R b27 ~R b29 each independently represents a group having a hydrogen atom or 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, multiple R b13 are the same or different, and when p2 is 2 or more, multiple R b14 are the same or different, and when q2 is 2 or more, multiple R b15 are the same or different, and when r2 is 2 or more, multiple R b16 are the same or different, and when s2 is 2 or more, multiple R b17 are the same or different, and when t2 is 2 or more, multiple R b18 are the same or different. o21, p22, q23, r24, t25 and s26 each independently represent an integer of 0 to 4. When o21, p22, q23, r24, t25 and s26 are each 2 or more, multiple R b21 ~R b26 are the same or different. u3 represents an integer of 1 to 3, and satisfies 1≦u3+q23≦5. u4 and u5 each independently represent an integer of 0 to 3, and satisfy 0≦u4+o21≦5 and 0≦u5+p22≦5. When u3, u4, and u5 each represent 2 or more, the groups in the parentheses are the same or different. When u2 is 0, any one of o2, p2, q2, and r2 is 1 or more, and R b13 ~R b16 At least one of o2, p2, s2, t2, q2 and r2 is preferably a halogen atom, and when u2 is 1, any one of o2, p2, s2, t2, q2 and r2 is 1 or more, and R b13 ~R b18 At least one of these is preferably a halogen atom. Furthermore, when u2 is 0, r2 is preferably 1 or more, and more preferably 1. When u2 is 0 and r2 is 1 or more, R b16 is preferably a halogen atom. The aliphatic hydrocarbon group refers to a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of the chain hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl. In particular, R b9 ~R b12 The chain hydrocarbon group preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups: TIFF2026026041000079.tif11157 In particular, R b9 ~R b12 The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, and more preferably has 4 to 12 carbon atoms. Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include a methylcyclohexyl group, a dimethylcyclohexyl group, a 2-methyladamantan-2-yl group, a 2-ethyladamantan-2-yl group, a 2-isopropyladamantan-2-yl group, a methylnorbornyl group, an isobornyl group, etc. In the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group, the total number of carbon atoms in the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 20 or less. The fluorinated alkyl group refers to an alkyl group having 1 to 12 carbon atoms and a fluorine atom, and examples thereof include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluorobutyl group, etc. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 9, more preferably 1 to 6, and even more preferably 1 to 4. Examples of aromatic hydrocarbon groups include aryl groups such as a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, etc. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples thereof include aromatic hydrocarbon groups having a chain hydrocarbon group (such as a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a p-ethylphenyl group, a p-tert-butylphenyl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, etc.) and aromatic hydrocarbon groups having an alicyclic hydrocarbon group (such as a p-cyclohexylphenyl group, a 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 aromatic hydrocarbon groups in which hydrogen atoms are substituted with alkoxy groups include p-methoxyphenyl groups. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as benzyl, phenethyl, phenylpropyl, trityl, naphthylmethyl, and naphthylethyl. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkylcarbonyloxy group include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, an isopropylcarbonyloxy group, a butylcarbonyloxy group, a sec-butylcarbonyloxy group, a tert-butylcarbonyloxy group, a pentylcarbonyloxy group, a hexylcarbonyloxy group, an octylcarbonyloxy group, and a 2-ethylhexylcarbonyloxy group. R b4 and R b5 and bond to each other together with the sulfur atom to which they are bonded to form a ring which may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. This ring may be a ring having 3 to 18 carbon atoms, preferably a ring having 4 to 18 carbon atoms. The ring containing a sulfur atom may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring, for example, the following rings. * represents a bonding site. TIFF2026026041000080.tif24142R b9 and R b10 The ring formed by these together may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. This ring may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring. Examples thereof include a thiolan-1-ium ring (tetrahydrothiophenium ring), a thian-1-ium ring, and a 1,4-oxathian-4-ium ring. R b11 and R b12 The ring formed by combining these may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of this ring include a 3- to 12-membered ring, and preferably a 3- to 7-membered ring. Examples include an oxocycloheptane ring, an oxocyclohexane ring, an oxonorbornane ring, and an oxoadamantane ring. R b27 ~R b29Examples of groups containing an acid labile group include -R c30 , -CO-OR c30 or -L c10 -CO-OR c30 A group represented by (L c10 represents an alkanediyl group having 1 to 6 carbon atoms, and R c30 represents an acid labile group. R b27 ~R b29 The acid labile group includes groups represented by formula (1) or (2).
[0088] Among the cations (b2-1) to (b2-5), the cation (b2-1), the cation (b2-4) or the cation (b2-5) is preferred. Examples of the cation (b2-1) include the following cations. TIFF2026026041000081.tif96163
[0089] TIFF2026026041000082.tif126162Examples of the cation (b2-2) include the following cations. TIFF2026026041000083.tif18150Examples of the cation (b2-3) include the following cations. TIFF2026026041000084.tif26140Examples of the cation (b2-4) include the following cations. TIFF2026026041000085.tif122163 Examples of the cation (b2-5) include the following cations. TIFF2026026041000086.tif101165
[0090] The acid generator (B) is a combination of the above-mentioned anions and the above-mentioned organic cations, and these can be combined arbitrarily. Preferred examples of the acid generator (B) include combinations of anions represented by any of formulas (B1a-1) to (B1a-4), (B1a-7) to (B1a-11), (B1a-14) to (B1a-30), (B1a-35) to (B1a-70), (B2a-1) to (B2a-11), (B2a-16) to (B2a-20), (B3a-1) to (B3a-3), and (B3a-11) to (B3a-14) with cations (b2-1), (b2-2), (b2-3), (b2-4), and (b2-5).
[0091] Preferred examples of the acid generator (B) include those represented by formulae (B1-1) to (B1-106), (B2-1) to (B2-20), and (B3-1) to (B3-28). Among these, those containing an arylsulfonium cation are preferred, and those represented by formulae (B1-1) to (B1-3), (B1-5) to (B1-7), (B1-11) to (B1-14), (B1-20) to (B1-26), (B1-29), (B1-31) to (B1-105), (B2-1) to (B2-20), and (B3-1) to (B3-28) are particularly preferred. JPEG2026026041000087.jpg176161
[0092] TIFF2026026041000088.tif254158
[0093] TIFF2026026041000089.tif254156
[0094] TIFF2026026041000090.tif253161
[0095] TIFF2026026041000091.tif253162
[0096] TIFF2026026041000092.tif251150
[0097] TIFF2026026041000093.tif185160
[0098] In the resist composition of the present invention, the total content of the acid generators is preferably 0.1 to 99.9% by mass, more preferably 1 to 45% by mass, even more preferably 1 to 40% by mass, and even more preferably 3 to 40% by mass, relative to the solid content of the resist composition. When the resist composition contains a resin (A) described below, the total content of the acid generators is preferably 1 to 45 parts by mass, more preferably 1 to 40 parts by mass, and even more preferably 3 to 40 parts by mass, relative to 100 parts by mass of the resin (A) described below. In the resist composition of the present invention, the total content of the carboxylate (I), acid generator (B), etc., relative to the solid content of the resist composition is preferably 0.1 to 99.9% by mass, more preferably 1 to 60% by mass, even more preferably 1 to 55% by mass, and even more preferably 3 to 50% by mass. When the resist composition contains the resin (A) described below, the total content of the carboxylate (I), acid generator (B), etc., relative to 100 parts by mass of the resin (A), is preferably 1 part by mass or more (more preferably 3 parts by mass or more), and preferably 65 parts by mass or less (more preferably 60 parts by mass or less, and even more preferably 58 parts by mass or less).
[0099] <Resin (A)> Resin (A) contains a structural unit having an acid labile group (hereinafter sometimes referred to as "structural unit (a1)"). Resin (A) preferably further contains a structural unit other than structural unit (a1). Examples of structural units other than structural unit (a1) include a structural unit not having an acid labile group (hereinafter sometimes referred to as "structural unit (s)") and structural units derived from other monomers known in the art.
[0100] <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 formula (1) (hereinafter also referred to as group (1)) and / or a group represented by formula (2) (hereinafter also referred to as group (2)). JPEG2026026041000094.jpg2298[In formula (1), R a1 , R a2 and R a3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining any of these; or R a1 and R a2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, 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. * denotes a binding site.] TIFF2026026041000095.tif2278[In formula (2), R a1’ and R a2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R a2’ and R a3’ are bonded to each other to form, together with the carbon atom to which they are bonded and X, a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced with -O- or -S-, 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. * denotes a binding site.]
[0101] R a1 , R a2 and R a3Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. R a1 , R a2 and R a3 Examples of the alkenyl group in the formula (I) include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. R a1 , R a2 and R a3 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (* indicates a bonding site): a1 , R a2 and R a3 The alicyclic hydrocarbon group preferably has 3 to 16 carbon atoms. TIFF2026026041000096.tif10159R a1 , R a2 and R a3 Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. Preferably, ma is 0 and na is 1. R a1 and R a2 -C(R a1 )(R a2 )(R a3 ) includes the following groups. The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms. * represents the bonding site with -O-. TIFF2026026041000097.tif28138
[0102] R a1’ , R a2’ and R a3’ Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. Alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups are R a1 , R a2 and R a3 Examples of the groups include the same as those listed in the above. R a2’ and R a3’ When they are bonded to each other to form a heterocyclic group together with the carbon atoms to which they are bonded and X, -C(R a1’ )(R a2’)-XR a3’ Examples of the groups include the following: * represents a binding site. TIFF2026026041000098.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 that may be contained in the ring may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
[0103] Examples of the group (1) include the following groups. In formula (1), R a1 , R a2 and R a3 is an alkyl group, ma=0, and na=1. The group is preferably a tert-butoxycarbonyl group. In formula (1), R a1 , R a2 together with the carbon atom to which they are attached form an adamantyl group, and R a3 is an alkyl group, ma=0, and na=1. In formula (1), R a1 and R a2 are each independently an alkyl group, and R a3 is an adamantyl group, ma=0, and na=1. Specific examples of the group (1) include the following: * represents a binding site. TIFF2026026041000099.tif149165
[0104] Specific examples of group (2) include the following groups: * represents a binding site. TIFF2026026041000100.tif55153
[0105] 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.
[0106] Of the (meth)acrylic monomers having an acid labile group, preferred are those having an alicyclic hydrocarbon group having 5 to 20 carbon atoms. When 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 a resist composition, the resolution of the resist pattern can be improved.
[0107] Examples of structural units derived from a (meth)acrylic monomer having group (1) include a structural unit represented by formula (a1-0) (hereinafter sometimes referred to as structural unit (a1-0)), a structural unit represented by formula (a1-1) (hereinafter sometimes referred to as structural unit (a1-1)), or a structural unit represented by formula (a1-2) (hereinafter sometimes referred to as structural unit (a1-2)). Preferably, at least one structural unit selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2) is used, and more preferably at least one or two structural units selected from the group consisting of structural unit (a1-1) and structural unit (a1-2). These may be used alone or in combination of two or more. TIFF2026026041000101.tif44144 [In formula (a1-0), formula (a1-1), and formula (a1-2), all symbols have the same meanings as defined above.]
[0108] R a01 , R a4 , R a5 The halogen atom in the formula (I) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. R a01 , R a4 , R a5Examples of the alkyl group optionally having a halogen atom in the formula (I) include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, 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, more preferably a methyl group. L a01 , L a1 and L a2 is preferably an oxygen atom or —O—(CH2) k01 It is —CO—O— (wherein k01 is preferably an integer of 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. R a6 and Ra7 The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and even more preferably an ethyl group, an isopropyl group, or a t-butyl group. R a6 and R a7 The alkenyl group in the formula (I) is preferably an alkenyl group having 2 to 6 carbon atoms, and more preferably an ethenyl group, a propenyl group, an isopropenyl group, or a butenyl group. R a02 , R a03 , R a04 , R a6 and R a7 The alicyclic hydrocarbon group preferably has 5 to 12 carbon atoms, and more preferably 5 to 10 carbon atoms. R a02 , R a03 , R a04 , R a6 and R a7 The aromatic hydrocarbon group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms. In the group in which an alkyl group and an alicyclic hydrocarbon group are combined, the total number of carbon atoms in the combination of the alkyl group and the alicyclic hydrocarbon group is preferably 18 or less. In the group in which an alkyl group and an aromatic hydrocarbon group are combined, the total number of carbon atoms in the combination of the alkyl group and the aromatic hydrocarbon group is preferably 18 or less. R a02 and R a03 is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, and more preferably a methyl group, ethyl group, phenyl group or 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, and more preferably a methyl group, ethyl group, cyclohexyl group or adamantyl group which may have a halogen atom. R a6 and R a7is 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, ethyl group, isopropyl group, t-butyl group, ethenyl group, phenyl group, or naphthyl group which may have a halogen atom, and even more preferably an ethyl group, isopropyl group, t-butyl group, ethenyl group, or phenyl group which may have a halogen atom. m1' is preferably an integer of 0 to 3, and more preferably 0 or 1. n1 is preferably an integer of 0 to 3, and more preferably 0 or 1. n1' is preferably 0 or 1.
[0109] Examples of the structural unit (a1-0) include structural units represented by any one of formulas (a1-0-1) to (a1-0-24) and R a01 and structural units in which the methyl group corresponding to the formula (a1-0-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group (an alkyl group having a halogen atom) or another alkyl group, and structural units represented by any of formulas (a1-0-1) to (a1-0-10), (a1-0-13), (a1-0-14), and (a1-0-19) to (a1-0-24) are preferred. TIFF2026026041000102.tif119160
[0110] Examples of the structural unit (a1-1) include structural units derived from monomers described in JP-A-2010-204646. Among these, structural units represented by any one of formulas (a1-1-1) to (a1-1-7) and R in the structural unit (a1-1) are preferred. a4 A structural unit in which the methyl group corresponding to the formula (a1-1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group is preferred, and a structural unit represented by any one of formulas (a1-1-1) to (a1-1-4) is more preferred. TIFF2026026041000103.tif35170
[0111] The structural unit (a1-2) includes a structural unit represented by any one of formulas (a1-2-1) to (a1-2-20) and R a5 and structural units in which the methyl group corresponding to the formula (a1-2-2), (a1-2-5), (a1-2-6), and (a1-2-10) to (a1-2-20) are substituted with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. TIFF2026026041000104.tif91164
[0112] 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 of these structural units, based on the total structural units of the resin (A), can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. Also, the total content can be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, the total content can be 10 to 95 mol%, preferably 15 to 90 mol%, more preferably 20 to 85 mol%, even more preferably 25 to 70 mol%, and even more preferably 30 to 70 mol%. When the resin (A) contains the structural unit (a1-0), the content thereof, based on the total structural units of the resin (A), can be 5 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more, even more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, and still more preferably 35 mol% or more. It can also be 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, even more preferably 65 mol% or less, and still more preferably 60 mol% or less. Specifically, it can be 5 to 80 mol%, preferably 5 to 75 mol%, more preferably 10 to 70 mol%, even more preferably 10 to 65 mol%, and still more preferably 10 to 60 mol%. When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), the total content of these structural units, based on the total structural units of the resin (A), can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. Also, the total content can be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, the total content can be 10 to 90 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, even more preferably 20 to 80 mol%, even more preferably 20 to 75 mol%, and even more preferably 20 to 70 mol%.
[0113] An example of the structural unit (a1) having the group (2) is a structural unit represented by formula (a1-4) (hereinafter, sometimes referred to as "structural unit (a1-4)"). TIFF2026026041000105.tif31118 [In formula (a1-4), all symbols have the same meanings as defined above.]
[0114] R a1 and R a17 Examples of the halogen atom and the alkyl group optionally having a halogen atom in formula (a1-0) include R a01 The same examples as those given above are included. R a1 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a17 The alkoxy group, alkoxyalkyl group, alkoxyalkoxy group, alkylcarbonyl group, and alkylcarbonyloxy group in the above may be the same as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, even more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably an alkoxyalkyl group having 2 to 4 carbon atoms, even more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably an alkoxyalkoxy group having 2 to 4 carbon atoms, and even more preferably a methoxyethoxy group or an ethoxyethoxy group. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group. R a17is 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.
[0115] A a11 Examples of the alkanediyl group include straight-chain alkyl groups such as methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl. Examples of branched alkanediyl groups include branched alkanediyl groups such as butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, 2-methylbutane-1,4-diyl, heptane-1,6-diyl, octane-1,7-diyl, nonane-1,8-diyl, decane-1,9-diyl, and undecane-1,10-diyl. The number of carbon atoms in 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 more preferably 1 to 3, and still more preferably 1 or 2. Among these, A a11 is also preferably a methylene group or an ethylene group. R a18 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a tert-butyl group. A a11 -CH2- in the alkanediyl group is -O-, -CO- or -NR a18 When substituted with -, the number of carbon atoms before substitution is regarded as the number of carbon atoms of the alkanediyl group. Aa11 -CH2- in the alkanediyl group is -O-, -CO- or -NR a18 Examples of the group substituted for A include a hydroxy group, a carboxy group, a carbonyl group, an oxy group, an amino group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylamino group, a peptide group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, and an alkanediylamino group. These substituted groups include the same as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. a11 -CH2- in the alkanediyl group is -O-, -CO- or -NR a18 Groups substituted with - include *-O-, *-CO-O-, *-O-CO-, and *-CO-OA. a12 -CO-O-, *-O-CO-A a12 -O-, *-OA a12 -CO-O-, *-CO-OA a12 -O-CO-, *-O-CO-A a12 -O-CO-, *-CO-NR a18 Among them, *-CO-O- and *-CO-OA a12 -CO-O-, *-OA a12 -CO-O-, *-CO-NR a18 - is preferred, where A a12 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents R a1 A represents the bonding site with the carbon atom to which it is attached. a12 The alkanediyl group of A is, within the limits of the upper limit of the carbon number, a11 Examples of the alkanediyl groups include the same alkanediyl groups as those shown in the above. A a11 is a single bond, *-CO-O- or *-CO-OA a12 -CO-O- is preferred, a single bond, *-CO-O- or *-CO-O-CH2-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred. 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.
[0116] R a34 , R a35 and R a36 Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group in which these groups are combined. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (* indicates a bonding site): TIFF2026026041000106.tif10151 Examples of aromatic hydrocarbon groups include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group. Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. In particular, R a36Examples of the group include an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these. R a35 and R a36 Examples of the divalent heterocyclic group having 3 to 20 carbon atoms that are formed by bonding together with the -CO- to which they are bonded include the following groups: * represents a bonding site, and one of the groups is R a34 This is the binding site for TIFF2026026041000107.tif15106
[0117] R a34 is preferably a hydrogen atom. R a35 is preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a methyl group or an ethyl group. R a36 The hydrocarbon group in R is preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these, and more preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms. a36 The alkyl group and alicyclic hydrocarbon group in R are preferably unsubstituted. a36 The aromatic hydrocarbon group in is preferably an aromatic ring having an aryloxy group having 6 to 10 carbon atoms.
[0118] -OC(R a34 )(R a35 )-OR a36 is eliminated upon contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxy group or a carboxy group. -X a1 -OC(R a34 )(R a35 )-OR a36 In the case of a benzene ring, A a11It is preferable that at least one of them is bonded to the o-position or the m-position, and more preferable that it is bonded to the p-position. In the case of a naphthalene ring, A a11 When the bonding position of A is the 1st position, it may be bonded to any of the 2nd to 8th positions. a11 When the bonding position of A is the 2nd position, it may be bonded to any of the 1st position and the 3rd to 8th positions. a11 When the bonding position of A is position 1, at least one of A is preferably bonded to position 3 to 6, and more preferably bonded to position 3 or 4. a11 When 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.
[0119] Examples of the structural unit (a1-4) include structural units derived from monomers described in JP-A-2010-204646. Preferred are structural units represented by formulas (a1-4-1) to (a1-4-42) and R in the structural unit (a1-4). a1 and more preferably, the structural units represented by formulae (a1-4-1) to (a1-4-5), (a1-4-10), (a1-4-13), (a1-4-14), (a1-4-19), and (a1-4-20). TIFF2026026041000108.tif229165
[0120] When the resin (A) contains the structural unit (a1-4), the content thereof, based on the total of all structural units in the resin (A), can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. The content can also be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, the content is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, even more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.
[0121] Examples of the structural unit derived from a (meth)acrylic monomer having the group (2) include a structural unit represented by formula (a1-5) (hereinafter, sometimes referred to as "structural unit (a1-5)"). TIFF2026026041000109.tif4558 [In formula (a1-5), all symbols have the same meanings as defined above.] R in formula (a1-5) a8 Examples of the halogen atom and the alkyl group optionally having a halogen atom in formula (a1-0) include R a01 The same examples as those given above are included. In formula (a1-5), R a8 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. L 51 is preferably an oxygen atom. L 52 and L 53 Among these, it is preferred that one is —O— and the other is —S—. s1 is preferably 1. s1' is preferably an integer of 0 to 2. Z a1is preferably a single bond or —CH2—CO—O—.
[0122] Examples of the structural unit (a1-5) include structural units derived from monomers described in JP-A-2010-61117. Among these, the structural units represented by formulas (a1-5-1) to (a1-5-4) are preferred, and the structural unit represented by formula (a1-5-1) or (a1-5-2) is more preferred. When the resin (A) contains the structural unit (a1-5), the content thereof, based on the total structural units of the resin (A), is preferably 1 mol% or more, preferably 2 mol% or more, more preferably 3 mol% or more, even more preferably 5 mol% or more, even more preferably 10 mol% or more, even more preferably 20 mol% or more, and even more preferably 25 mol% or more. It may also be 80 mol% or less, preferably 70 mol% or less, more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 45 mol% or less, even more preferably 40 mol% or less, and even more preferably 30 mol% or less. Specifically, it is preferably 1 to 50 mol%, more preferably 3 to 45 mol%, even more preferably 5 to 40 mol%, and even more preferably 5 to 30 mol%.
[0123] An example of the structural unit (a1) having the group (1) is a structural unit represented by formula (a1-6) (hereinafter, sometimes referred to as "structural unit (a1-6)"). TIFF2026026041000111.tif3479 [In formula (a1-6), all symbols have the same meanings as defined above.] R in formula (a1-6) a61 Examples of the halogen atom and the alkyl group optionally having a halogen atom in formula (a1-0) include R a01 The same examples as those given above are included. R a61 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. R a62, R a63 , R a64 and R a65 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, etc. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group or an ethyl group. R a62 , R a63 and R a64 The cyclic hydrocarbon group in the formula (I) includes an alicyclic hydrocarbon group and an aromatic hydrocarbon group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Examples of polycyclic alicyclic hydrocarbon groups include a decahydronaphthyl group, an adamantyl group, and a norbornyl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16, and more preferably 3 to 12. Examples of the aromatic hydrocarbon group include a phenylene group and a naphthylene group. Examples of the substituent that the cyclic hydrocarbon group may have include a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. R a62 and R a63 Examples of the ring formed by bonding together include an adamantane ring, a cyclopentane ring, and a cyclohexane ring. a62 and R a63 -C(R a62 )(R a63 )(R a64 ) includes the following groups. * represents the bonding site with the oxygen atom. The number of carbon atoms in the ring is preferably 3 to 16, and more preferably 3 to 12. TIFF2026026041000112.tif33109
[0124] L a61 and L a62 Examples of the alkanediyl group having 1 to 4 carbon atoms in the formula include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group. L a61 and L a62 are each preferably 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 *-OL a61 -, and more preferably a single bond.
[0125] Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms for Ar include a phenylene group, an o-methylphenylene group, an m-methylphenylene group, a p-methylphenylene group, a p-ethylphenylene group, a p-tert-butylphenylene group, a 1-naphthylene group, a 2-naphthylene group, a 1-anthrylene group, a 9-anthrylene group, a biphenylene group, a 1-phenanthrylene group, and a 2-phenanthrylene group. Examples of the substituent that the aromatic hydrocarbon group may have include a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. These groups are preferably used in the R a17 Examples include the same as those exemplified above. The substituent is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group. Ar is preferably a phenylene group which may have a substituent, and more preferably a phenylene group which may have a hydroxy group.
[0126] Examples of the structural unit (a1-6) include structural units represented by formulas (a1-6-1) to (a1-6-44), preferably structural units represented by formulas (a1-6-1) to (a1-6-9), and (a1-6-37) to (a1-6-44), more preferably structural units represented by formulas (a1-6-1), (a1-6-2), (a1-6-4), (a1-6-5), (a1-6-7), (a1-6-8), and (a1-6-37) to (a1-6-44), and even more preferably structural units represented by formulas (a1-6-7), (a1-6-8), and (a1-6-37) to (a1-6-44). a61 In the structural units shown below, the hydrogen atom corresponding to R is replaced by a methyl group or the like. a61 The structural unit (a1-6) also includes a structural unit in which the methyl group corresponding to the following is replaced with a hydrogen atom or the like. TIFF2026026041000113.tif226165
[0127] When the resin (A) contains the structural unit (a1-6), the content thereof, based on the total structural units of the resin (A), can be 3 mol% or more, preferably 5 mol% or more, more preferably 7 mol% or more, even more preferably 10 mol% or more, still more preferably 20 mol% or more, even more preferably 30 mol% or more, and even more preferably 40 mol% or more. Also, the content can be 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, the content is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, even more preferably 7 to 70 mol%, even more preferably 7 to 65 mol%, and particularly preferably 10 to 60 mol%.
[0128] Further, examples of the structural unit (a1) include the following structural units. TIFF2026026041000114.tif33167
[0129] When resin (A) contains structural units represented by formulae (a1-7-1) to (a1-7-7), the content of these structural units relative to the total structural units of resin (A) is typically 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. Also, the content may be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, the content is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, even more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.
[0130] Further, examples of the structural unit (a1) include the following structural units. When resin (A) contains structural units represented by formulas (a1-8-1) to (a1-8-3), the content thereof, based on the total structural units of resin (A), can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. Also, the content can be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, it is preferably 10 to 60 mol %, more preferably 15 to 55 mol %, even more preferably 20 to 50 mol %, even more preferably 20 to 45 mol %, and particularly preferably 20 to 40 mol %.
[0131] <Structural unit(s)> The structural unit (s) is derived from a monomer (hereinafter sometimes referred to as "monomer (s)") that does not have an acid labile group. As the monomer from which the structural unit (s) is derived, a monomer that does not have an acid labile group known in the resist field can be used. The structural unit (s) preferably has a hydroxy group, a carboxy group, or a lactone ring. The use of a resin containing a structural unit having a hydroxy group or a carboxy group but no acid labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring but no acid labile group (hereinafter sometimes referred to as "structural unit (a3)") in the resist composition of the present invention can improve the resolution of the resist pattern and adhesion to the substrate. In addition to the structural units described above, structural units (s) may also include structural units having a halogen atom (hereinafter sometimes referred to as "structural unit (a4)"), structural units having a non-leaving hydrocarbon group (hereinafter sometimes referred to as "structural unit (a5)"), structural units having a sultone structure (hereinafter sometimes referred to as "structural unit (a6)"), structural units that decompose upon exposure to generate acid (hereinafter sometimes referred to as "structural unit (a7)"), and other structural units known in the art.
[0132] <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. TIFF2026026041000116.tif4095[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 -CH2- contained in the alkanediyl group 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. L a21 represents a single bond or a hydrocarbon group having 1 to 28 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group is not -O-, -CO-, -S-, -SO-, or -NR a28 It may be replaced by - or -SO2-. La22 represents a single bond or a chain hydrocarbon group of 1 to 12 carbon atoms which may have a fluorine atom, and -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-. na2 represents an integer of 1 to 5. When na2 is 2 or more, a plurality of L a22 may be the same or different from each other. R a2 Examples of the halogen atom and the alkyl group optionally having a halogen atom in formula (a1-0) include R a01 The same examples as those given above are included. 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 even more preferably a hydrogen atom or a methyl group.
[0133] A a21 , R a28 is A in formula (a1-4). a11 , R a18 The same can be mentioned. A a21 -CH2- in the alkanediyl group is -O-, -CO- or -NR a28 Groups substituted with - include *-O-, *-CO-O-, *-O-CO-, and *-CO-OA. a22 -CO-O-, *-O-CO-A a22 -O-, *-OA a22 -CO-O-, *-CO-OA a22 -O-CO-, *-O-CO-A a22 -O-CO-, *-CO-NR a28 Among them, *-CO-O- and *-CO-OA a22 -CO-O-, *-OA a22 -CO-O-, *-CO-NR a28 - is preferred, where A a22 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents R a2 A represents the bonding site with the carbon atom to which it is attached. a22 The alkanediyl group of A is, within the limits of the upper limit of the carbon number, a21Examples of the alkanediyl groups include the same alkanediyl groups as those shown in the above. A a21 is a single bond, *-CO-O- or *-CO-OA a22 -CO-O- is preferred, a single bond, *-CO-O- or *-CO-O-CH2-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.
[0134] L a21 The hydrocarbon group in is a (na2+1)-valent hydrocarbon group, and examples thereof include linear or branched chain hydrocarbon groups, monocyclic or polycyclic (including spiro rings, fused rings, or bridged rings) alicyclic hydrocarbon groups, and cyclic hydrocarbon groups such as aromatic hydrocarbon groups, and may also be a group combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group). L a21 Examples of the chain hydrocarbon group include divalent to hexavalent chain hydrocarbon groups such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, an alkanpentyl group, and an alkanehexyl group. Examples of the alkanediyl group include A a21 Examples of the alkanediyl groups include the same alkanediyl groups as those shown in the above. Examples of the alkanetriyl group include a methanetriyl group, an ethanetriyl group, a propanetriyl group, a butanetriyl group, a pentanetriyl group, a hexanetriyl group, a heptanetriyl group, an octanetriyl group, a nonanetriyl group, a decantriyl group, an undecanetriyl group, a dodecanetriyl group, a tridecanetriyl group, a tetradecanetriyl group, a pentadecanetriyl group, a hexadecanetriyl group, and a heptadecanetriyl group. Examples of the alkanetetrayl group include a methanetetrayl group, an ethanetetrayl group, a propanetetrayl group, a butanetetrayl group, a pentanetetrayl group, a hexanetetrayl group, a heptanetetrayl group, an octanetetrayl group, a nonanetetrayl group, a decanetetrayl group, an undecanetetrayl group, a dodecanetetrayl group, a tridecanetetrayl group, a tetradecanetetrayl group, a pentadecanetetrayl group, a hexadecanetetrayl group, and a heptadecanetetrayl group. Examples of the alkanpentyl group include a methanepentyl group, an ethanepentyl group, a propanepentyl group, a butanepentyl group, a pentanepentyl group, and a hexanepentyl group. Examples of the alkanehexyl group include a methanehexyl group, an ethanehexyl group, a propanehexyl group, a butanehexyl group, a pentanehexyl group, and a hexanehexyl group. Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, still more preferably 1 to 9, even more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 5, and particularly preferably 1 to 4. L a21 Examples of the monocyclic and polycyclic alicyclic hydrocarbon groups in the above formula include the following alicyclic hydrocarbon groups: The binding site can be at any position. TIFF2026026041000117.tif42164 Examples include divalent to hexavalent alicyclic hydrocarbon groups such as a cycloalkanediyl group, a cycloalkanetriyl group, a cycloalkanetetrayl group, a cycloalkanepentyl group, and a cycloalkanehexyl group. 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, and cyclodecanetetrayl group; Examples of polycyclic alicyclic hydrocarbon groups include norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, decahydronaphthalenediyl group, bicyclo[3.3.0]octanediyl group, norbornanetriyl group, adamantanetriyl group, decahydronaphthalenetriyl group, bicyclo[3.3.0]octanetriyl group, norbornanetetrayl group, adamantanetetrayl group, decahydronaphthalenetetrayl group, and bicyclo[3.3.0]octanetetrayl group. Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. The alicyclic hydrocarbon group preferably has 3 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 16 carbon atoms, still more preferably 3 to 12 carbon atoms, even more preferably 6 to 12 carbon atoms, and particularly preferably 6 to 10 carbon atoms. L a21 Examples of the aromatic hydrocarbon group in include divalent to hexavalent aromatic hydrocarbon groups such as an arylene group, an arenetriyl group, an arenetetrayl group, an arenetyl group, and an arenehexyl group. Specific 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, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, still more preferably 6 to 14, still more preferably 6 to 12, and still more preferably 6 to 10. Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. Examples of the group combining two or more types include a group combining an alicyclic hydrocarbon group with a chain hydrocarbon group, a group combining an aromatic hydrocarbon group with a chain hydrocarbon group, a group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group, and a group combining an alicyclic hydrocarbon group with a chain hydrocarbon group and an aromatic hydrocarbon group. In the combination, two or more types of each of the alicyclic hydrocarbon group, aromatic hydrocarbon group, and chain hydrocarbon group may be combined. In addition, when any group is A a21 and L a22 may be bound to L a21 The alkanediyl group may be substituted with -O- or -CO-, etc., and L a21 When the alkanediyl group 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-, * represents X a2 It is preferable that the bond is The -CH2- contained in the hydrocarbon group can be -O-, -S-, -SO2-, -SO-, or -NR a28Examples of the group substituted with - or -CO- include a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced with -S-), an amino group (a group in which -CH2- in a methyl group is replaced with -NR a28 -), carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), oxy group (a group in which -CH2- in a methylene group is replaced with -O-), carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), thio group (a group in which -CH2- in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), peptide group (a group in which -CH2-CH2- in an ethylene group is replaced with -CO-NR a28 -), alkoxy group (a group in which -CH2- at any position in the alkyl group is replaced with -O-), alkylthio group (a group in which -CH2- at any position in the alkyl group is replaced with -S-), alkoxycarbonyl group (a group in which -CH2-CH2- at any position in the alkyl group is replaced with -O-CO-), alkylsulfonyl group (a group in which -CH2- at any position in the alkyl group is replaced with -SO2-), alkylamino group (a group in which -CH2- at any position in the alkyl group is replaced with -NR a28 -), alkyl peptide group (wherein -CH2-CH2- at any position in the alkyl group is replaced by -CO-NR a28-), alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), alkoxycarbonyloxy group (a group in which -CH2-CH2-CH2- at any position in an alkyl group is replaced with -O-CO-O-), alkoxyalkoxy group (a group in which two -CH2- at any position in an alkyl group are replaced with -O-), alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -O-), alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO- an alkanediylcarbonyl group (an alkanediyl group in which -CH2- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (an alkanediyl group in which -CH2-CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyloxy group (an alkanediyl group in which -CH2-CH2-CH2- at any position is replaced with -O-CO-O-), an alkanediylsulfonyl group (an alkanediyl group in which -CH2- at any position is replaced with -SO2-), an alkanediylthio group (an alkanediyl group in which -CH2- at any position is replaced with -S-), an alkanediylamino group (an alkanediyl group in which -CH2- at any position is replaced with -NR a28 -), alkanediyl peptide group (wherein any -CH2-CH2- at any position in the alkanediyl group is replaced by -CO-NR a28 Examples of such groups include a group substituted with -, a cycloalkoxy group, a cycloalkylalkoxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group combining two or more of these groups. Also included are groups in which one or more hydrogen atoms of these groups have been replaced with a bonding site. Examples of such substituted 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.
[0135] In addition, -CH2- contained in an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these may be -O-, -S-, -CO-, -SO-, -NR a28 The group substituted with - or -SO2- includes the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. L a21 The hydrocarbon group in may have one or more substituents. Examples of the substituent include a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, an alkyl group having 1 to 16 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced by —O— or —CO—), an acryloyloxy group, or a methacryloyloxy group. Examples of these groups include the same groups as those exemplified in this specification. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L a21 The hydrocarbon group in the formula (I) may have a halogen atom as a substituent, thereby substantially having a substituent such as a haloalkyl group. Examples of the haloalkyl group include alkyl fluoride, alkyl chloride, alkyl bromide, and alkyl iodide, such as a chloromethyl group, bromomethyl group, iodomethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, and perfluorobutyl group. The number of carbon atoms in the haloalkyl group is preferably 1 to 8, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. L a21 The hydrocarbon group of L a21can substantially have a substituent such as an alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. L a21 The -CH2- contained in the hydrocarbon group is -O-, -S-, -CO-, -SO-, -NR a28 - or -SO2-, L a21 can substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, a thiol group, an alkylthio group, an alkylsulfonyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxyalkyl group, an alkoxyalkoxy group, an alkoxycarbonyloxy group, an amino group, an alkylamino group, an alkylpeptide group, an acryloyloxy group, or a methacryloyloxy group. Examples of the above groups include the same groups as those exemplified in this specification. L a21The substituents that the hydrocarbon group in the formula (I) may have are preferably a halogen atom, a haloalkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 12 carbon atoms (wherein —CH— contained in the alkyl group may be replaced with —O— or —CO—), more preferably a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 10 carbon atoms (wherein —CH— contained in the alkyl group may be replaced with —O— or —CO—), still more preferably 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, still more preferably 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, still more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, a methoxy group, or an ethoxyethoxy group. Also, L a21 When the alkanediyl group 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-, * represents A a21 It is also preferred that the bond is L a21 represents a single bond, a chain hydrocarbon group having 1 to 12 carbon atoms which may have a substituent (provided that -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (provided that -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR a28- or -SO2-) or a group formed by combining a chain hydrocarbon group of 1 to 8 carbon atoms which may have a substituent with a cyclic hydrocarbon group of 3 to 20 carbon atoms which may have a substituent (wherein -CH2- in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH2- in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR a28 - or -CO-), and examples thereof include an optionally substituted chain hydrocarbon group having 1 to 10 carbon atoms (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), and an optionally substituted cyclic hydrocarbon group having 3 to 18 carbon atoms (wherein -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR a28 - or -SO2-) or a group formed by combining a chain hydrocarbon group of 1 to 6 carbon atoms which may have a substituent with a cyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent (provided that -CH2- in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH2- in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR a28 - or -CO- may be substituted.) is more preferred.
[0136] L a22Examples of the chain hydrocarbon group having 1 to 12 carbon atoms include straight-chain alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl. Examples of branched alkanediyl groups include ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, 1-methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-dimethylpropane-1,3-diyl, pentane-2,4-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, even more preferably 1 to 6, and even more preferably 1 to 4. L a22 may have one or more fluorine atoms. L a22 The -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and these substituted groups may be in the range of L, as long as the upper limit of the number of carbon atoms allows. a21 Examples include the same as those exemplified above. na2 is preferably an integer of 1 to 4, and more preferably an integer of 1 to 3. L a21 When R is a single bond or a chain hydrocarbon group, examples of the structural unit (a2) include the following structural units: a2 A structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom or the like is also a suitable structural unit of the structural unit (a2), similar to the structural units shown below. TIFF2026026041000118.tif67169
[0137] When producing a resist pattern from the resist composition of the present invention, if a high-energy ray such as a KrF excimer laser (248 nm), an electron beam, or EUV (extreme ultraviolet) is used as an exposure light source, the structural unit (a2) preferably has a phenolic hydroxy group, and more preferably the structural unit (a2-A) described below. Furthermore, if an ArF excimer laser (193 nm) or the like is used, the structural unit (a2) preferably has an alcoholic hydroxy group, and more preferably the structural unit (a2-C) described below. The structural unit (a2) may contain one type alone or two or more types.
[0138] In the structural unit (a2), L a21 is a cyclic hydrocarbon group, and examples of the structural unit having a phenolic hydroxy group or carboxy group include a structural unit represented by formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A)"). TIFF2026026041000119.tif31127 [In formula (a2-A), all symbols have the same meanings as defined above.]
[0139] R a2 and A a21 The groups include the same groups as those exemplified in formula (a2). R a27 is R in formula (a1-4). a17 The same groups as those shown below can be mentioned. 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. nA2 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. na21 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. mc is preferably 0 or 1. -X a2 -OH is a benzene ring, A a21 It is preferable that at least one of them is bonded to the m-position or p-position, and more preferable that it is bonded to the m-position. In the case of a naphthalene ring, A a21 When the bonding position of A is the 1st position, it may be bonded to any of the 2nd to 8th positions. a21 When the bonding position of A is the 2nd position, it may be bonded to any of the 1st position and the 3rd to 8th positions. a21 When the bonding position of A is position 1, at least one of A is preferably bonded to position 3 to 6, and more preferably bonded to position 3 or 4. a21 When 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.
[0140] Examples of the structural unit (a2-A) include structural units derived from monomers described in JP-A Nos. 2010-204634 and 2012-12577. The structural unit (a2-A) includes structural units represented by formulae (a2-2-1) to (a2-2-32), (a2-3-1) to (a2-3-24), and structural units represented by formulae (a2-2-1) to (a2-2-32), (a2-3-1) to (a2-3-24), where R in the structural unit (a2-A) a2 and a structural unit in which the methyl group corresponding to the following formula is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group. TIFF2026026041000120.tif109169
[0141] When the structural unit (a2-A) is contained in the resin (A), the content of the structural unit (a2-A) is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 15 mol% or more, and even more preferably 20 mol% or more, based on all structural units. It is also preferably 80 mol% or less, more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, even more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%. The structural unit (a2-A) may be a compound from which the structural unit (a2-A) is derived (e.g., -CH2-C(-R a2 )- is the double bond CH2=C(-R a2 The structural unit (a2-A) can be incorporated into the resin (A) by polymerizing the compound (a2-A')) in the state of (a1-4). Alternatively, for example, the structural unit (a1-4) can be polymerized, followed by treatment with an acid such as p-toluenesulfonic acid, to incorporate the structural unit into the resin (A). Alternatively, the structural unit (a2-A) can be polymerized using acetoxystyrene or the like, followed by treatment with an alkali such as tetramethylammonium hydroxide, to incorporate the structural unit into the resin (A).
[0142] In the structural unit (a2), L a21 is a cyclic hydrocarbon group, examples of the structural unit having an alcoholic hydroxy group or a carboxy group include a structural unit represented by formula (a2-B) (hereinafter may be referred to as "structural unit (a2-B)"), a structural unit represented by formula (a2-C) (hereinafter may be referred to as "structural unit (a2-C)"), and a structural unit represented by formula (a2-D) (hereinafter may be referred to as "structural unit (a2-D)"). TIFF2026026041000122.tif46100[In formula (a2-B) and formula (a2-C), R a2 has the same meaning as formula (a2). R a27has the same meaning as formula (a2-A). L a25 is -O- or *-O-(CH2) k2 represents —CO—O—, 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 represents 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 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 or different from each other. nC22 represents an integer of 0 to 10. When nC22 is 2 or more, a plurality of R a27 may be the same or different from each other. L a25 is preferably —O— or —O—(CH2) f1 It is —CO—O— (wherein f1 represents an integer of 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 a27is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 4 carbon atoms or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an 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 an integer of 0 to 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. nC22 is preferably an integer of 0 to 6, more preferably an integer of 0 to 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1.
[0143] Examples of the structural unit (a2-B) and the structural unit (a2-C) include structural units derived from monomers described in JP-A-2010-204646, the following structural units, and R in the following structural units: a2 In particular, structural units represented by any one of formulas (a2-B-1) to (a2-B-5) and formulas (a2-C-1) to (a2-C-9) are preferred. When the resin (A) contains the structural unit (a2-B) or the structural unit (a2-C), the content thereof, based on the total structural units of the resin (A), is 1 mol% or more, preferably 2 mol% or more. Alternatively, the content may be 45 mol% or less, preferably 40 mol% or less, more preferably 35 mol% or less, even more preferably 20 mol% or less, and even more preferably 10 mol% or less. Specifically, the content may be 1 to 45 mol%, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, even more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol%.
[0144] TIFF2026026041000124.tif51105[In formula (a2-D), R a2 and A a21 have the same meaning as in formula (a2). R a27 has the same meaning as formula (a2-A). R a21 and R a22 each independently represents 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 an integer of 1 to 5. When nD2 is 2 or greater, the groups in the parentheses may be the same or different. nD22 represents an integer of 0 to 4. When nD22 is 2 or more, a plurality of R a27 may be the same or different from each other. However, 1≦nD2+nD22≦5. R a21 and R a22 Examples of the fluorinated alkyl groups are each independently 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 a22As the aryl group, a trifluoromethyl group is preferred. L a24 Examples of the alkanediyl group include a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group. 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 an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0.
[0145] The structural unit (a2-D) is more preferably a structural unit represented by the following formula (a2-D1) (hereinafter, sometimes referred to as "structural unit (a2-D1)"). TIFF2026026041000125.tif51107[In 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.
[0146] Examples of the structural unit (a2-D) include the structural units shown below. TIFF2026026041000126.tif62167
[0147] In the structural units represented by formulae (a2-D-1) to (a2-D-8), R a2 In the structural units represented by formulas (a2-D-9) to (a2-D-16), the hydrogen atom corresponding to R a2 Specific examples of the structural unit (a2-D) include structural units in which the methyl group corresponding to the following formula is replaced with a hydrogen atom, etc. Among these, structural units represented by formulas (a2-D-1) to (a2-D-8) are preferred, structural units represented by formulas (a2-D-1) to (a2-D-4) are more preferred, and structural units represented by formula (a2-D-1) are even more preferred.
[0148] When the resin (A) contains the structural unit (a2-D), its content is preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, based on the total structural units of the resin (A). It is also preferably 80 mol% or less, more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, even more preferably 10 to 70 mol%, and even more preferably 10 to 65 mol%.
[0149] <Structural unit (a3)> The lactone ring contained in the structural unit (a3) may be a monocyclic ring such as a β-propiolactone ring, a γ-butyrolactone ring, or a δ-valerolactone ring, or a condensed ring of a monocyclic lactone ring with another ring. Preferred examples include a γ-butyrolactone ring, an adamantane lactone ring, or a bridged ring containing a γ-butyrolactone ring structure (for example, a structural unit represented by the following formula (a3-2)). The structural unit (a3) is preferably a structural unit represented by formula (a3-1), formula (a3-2), formula (a3-3), or formula (a3-4). One of these may be contained alone, or two or more may be contained. TIFF2026026041000127.tif51164 [In formula (a3-1), formula (a3-2), formula (a3-3) and formula (a3-4), L a4 , L a5 and L a6 are each independently -O- or -O-(CH2) k3 It represents a group represented by —CO—O— (k3 represents an integer of 1 to 7). L a7 -O-, *-OL a8 -O-, *-OL a8 -CO-O-, *-OL a8 -CO-OL a9 -CO-O- or *-OL a8 -O-CO-L a9 Represents -O-. L a8 and L a9 each independently represents an alkanediyl group having 1 to 6 carbon atoms. * indicates the bonding site with the carbonyl group. R a18 , R a19 , R a20 and R a24 each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X a3 represents -CH2- or an oxygen atom. R a21 represents an aliphatic hydrocarbon group having 1 to 4 carbon atoms. R a22 , R a23 and R a25 each independently represents a carboxy group, a cyano group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms. p1 represents an integer of 0 to 5. q1 represents an integer of 0 to 3. r1 represents an integer of 0 to 3. w1 represents an integer of 0 to 8. When p1, q1, r1 and / or w1 are 2 or more, multiple R a21 , R a22 , R a23 and / or R a25 may be the same as or different from each other.
[0150] R a21 , R a22 , R a23 and R a25 Examples of the aliphatic hydrocarbon group in include alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, and a tert-butyl group. R a18 , R a19 , R a20 and R a24 Examples of the halogen atom and the alkyl group optionally having a halogen atom in the formula (a1-0) to the formula (a1-2) include R a01 , R a4 , R a5 Examples include the same as those exemplified above. L a8 and L a9 Examples of the alkanediyl group in the formula (I) include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. L a4 ~L a6 are each independently preferably -O- or -O-(CH2) k3 In -CO-O-, k3 is a group in which k3 is any integer of 1 to 4, more preferably -O- and *-O-CH2-CO-O-, and further preferably an oxygen atom. L a7 is preferably -O- or *-OL a8It is —CO—O—, and 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 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R 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 each independently represent preferably an integer of 0 to 2, and more preferably 0 or 1.
[0151] w1 is preferably an integer of 0 to 2, and more preferably 0 or 1. In particular, the formula (a3-4) is preferably the formula (a3-4'). TIFF2026026041000128.tif2956(in the formula, R a24 , L a7 has the same meaning as above.)
[0152] Examples of the structural unit (a3) include structural units derived from monomers described in JP 2010-204646 A, JP 2000-122294 A, and JP 2012-41274 A. Examples of the structural unit (a3) include structural units represented by any of formulas (a3-1-1), (a3-1-2), (a3-2-1), (a3-2-2), (a3-3-1), (a3-3-2), and (a3-4-1) to (a3-4-12), and in the structural units, R in formulas (a3-1) to (a3-4) a18 , R a19 , R a20 and R a24 A structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom is preferred. When the resin (A) contains the structural unit (a3), the total content thereof, based on all structural units in the resin (A), is typically 1 mol% or more, preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more. It may also be 70 mol% or less, preferably 65 mol% or less, more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 40 mol% or less, even more preferably 30 mol% or less, even more preferably 25 mol% or less, and even more preferably 20 mol% or less. Specifically, it may be 1 to 70 mol%, preferably 3 to 70 mol%, more preferably 3 to 65 mol%, even more preferably 5 to 65 mol%, even more preferably 5 to 60 mol%, and even more preferably 10 to 60 mol%. Furthermore, the content of the structural unit (a3-1), the structural unit (a3-2), the structural unit (a3-3), or the structural unit (a3-4) is preferably 1 mol% or more, more preferably 3 mol% or more, even more preferably 5 mol% or more, and even more preferably 10 mol% or more, based on the total structural units of the resin (A). It is also preferably 60 mol% or less, more preferably 55 mol% or less, even more preferably 50 mol% or less, still more preferably 40 mol% or less, even more preferably 30 mol% or less, still more preferably 25 mol% or less, and even more preferably 20 mol% or less. Specifically, it is preferably 1 to 60 mol%, more preferably 3 to 60 mol%, even more preferably 3 to 55 mol%, even more preferably 5 to 55 mol%, even more preferably 5 to 50 mol%, and even more preferably 10 to 50 mol%.
[0153] <Structural unit (a4)> The structural unit represented by formula (a4) is shown below. TIFF2026026041000130.tif2753[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R42 represents an aliphatic hydrocarbon group having 1 to 48 carbon atoms and containing a halogen atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-.]
[0154] R 42 Examples of the aliphatic hydrocarbon group represented by the formula (I) include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these groups. Examples of the chain hydrocarbon group include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl groups, and branched alkyl groups such as isopropyl and isobutyl groups. Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include monocyclic alicyclic hydrocarbon groups which are monocyclic cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group; and polycyclic alicyclic hydrocarbon groups which are polycyclic cycloalkyl groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following groups (* indicates a bonding site): TIFF2026026041000131.tif10146 Examples of groups formed by combination include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic hydrocarbon group-alkyl group. Examples of the alkanediyl group include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and branched alkanediyl groups such as propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-methylbutane-1,4-diyl, and 2-methylbutane-1,4-diyl. The terminal of the branched alkanediyl group may be a methyl group. R42 Examples of the halogen atom contained in the aliphatic hydrocarbon group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 42 Examples of the aliphatic hydrocarbon group in which -CH- is replaced with -O- or -CO- include a hydroxy group, a carboxy group, a carbonyl group, an oxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, a cycloalkoxy group, a cycloalkylalkoxy group, and a group combining two or more of these groups. These substituted groups include the same groups as exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.
[0155] The structural unit (a4) is R 42 is preferably an aliphatic hydrocarbon group having a fluorine atom, and R 42 However, examples of the structural unit (a4) that is an aliphatic hydrocarbon group having a fluorine atom include a structural unit represented by formula (a4-1) (hereinafter, may be referred to as "structural unit (a4-1)"), a structural unit represented by formula (a4-2) (hereinafter, may be referred to as "structural unit (a4-2)"), a structural unit represented by formula (a4-3) (hereinafter, may be referred to as "structural unit (a4-3)"), and a structural unit represented by formula (a4-A) (hereinafter, may be referred to as "structural unit (a4-A)"). The structural unit represented by formula (a4-1) is a structural unit shown below. TIFF2026026041000132.tif3092[In 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 a fluorine atom-containing alkanediyl group having 1 to 8 carbon atoms or a fluorine atom-containing cycloalkanediyl group having 3 to 12 carbon atoms. R 42frepresents a hydrogen atom or a fluorine atom.
[0156] L 41 Examples of the alkanediyl group in the formula (I) include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, and butane-1,4-diyl, and branched alkanediyl groups such as ethane-1,1-diyl, propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1,3-diyl, and 2-methylpropane-1,2-diyl. The terminal of the branched alkanediyl group may be a methyl group. L 42f Examples of the alkanediyl group having a fluorine atom in the formula (I) include a linear alkanediyl group 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 branched alkanediyl groups having fluorine atoms include ethane-1,1-diyl groups having fluorine atoms, propane-1,1-diyl groups having fluorine atoms, propane-1,2-diyl groups having fluorine atoms, propane-2,2-diyl groups having fluorine atoms, pentane-2,4-diyl groups having fluorine atoms, 2-methylpropane-1,3-diyl groups having fluorine atoms, 2-methylpropane-1,2-diyl groups having fluorine atoms, pentane-1,4-diyl groups having fluorine atoms, and 2-methylbutane-1,4-diyl groups having fluorine atoms. The terminal of the branched alkanediyl group may be a methyl group which may have a fluorine atom. L 42fExamples of the cycloalkanediyl group having a fluorine atom in the formula (I) 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 polycyclic cycloalkanediyl groups having a fluorine atom include a norbornane-1,4-diyl group having a fluorine atom, a norbornane-2,5-diyl group having a fluorine atom, a 5-norbornene-2,3-diyl group having a fluorine atom, an adamantane-1,5-diyl group having a fluorine atom, and an adamantane-2,6-diyl group having a fluorine atom. L 42f The number of fluorine atoms contained in the alkanediyl group and cycloalkanediyl group having a fluorine atom in the formula (I) may be 1 or more, and is preferably 2 or more. L 42f The alkanediyl group and cycloalkanediyl group having a fluorine atom in the formula (I) are preferably a perfluoroalkanediyl group and a perfluorocycloalkanediyl group, respectively.
[0157] L 42fExamples of the perfluoroalkanediyl group in the formula (I) include a difluoromethylene group, a perfluoroethylene group, a perfluoroethylfluoromethylene group, a perfluoropropane-1,3-diyl group, a perfluoropropane-1,2-diyl group, a perfluoropropane-2,2-diyl group, a perfluorobutane-1,4-diyl group, a perfluorobutane-2,2-diyl group, a perfluorobutane-1,2-diyl group, a perfluoropentane-1,5-diyl group, a perfluoropentane-2,2-diyl group, a perfluoropentane-3 ,3-diyl group, perfluorohexane-1,6-diyl group, perfluorohexane-2,2-diyl group, perfluorohexane-3,3-diyl group, perfluoroheptane-1,7-diyl group, perfluoroheptane-2,2-diyl group, perfluoroheptane-3,4-diyl group, perfluoroheptane-4,4-diyl group, perfluorooctane-1,8-diyl group, perfluorooctane-2,2-diyl group, perfluorooctane-3,3-diyl group, and perfluorooctane-4,4-diyl group. L 42f Examples of the perfluorocycloalkanediyl group in the formula (I) include a perfluorocyclohexanediyl group, a perfluorocyclopentanediyl group, a perfluorocycloheptanediyl group, and a perfluoroadamantanediyl group.
[0158] L 41 is preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms, more preferably a single bond, a methylene group or an ethylene group, and even more preferably a single bond or a methylene group. L 42f is preferably a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluorocycloalkanediyl group having 3 to 12 carbon atoms, more preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and even more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.
[0159] The structural unit (a4-1) includes the structural units shown below and R in the structural unit (a4-1) in the structural units shown below. 41The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2026026041000133.tif55167The structural unit represented by formula (a4-2) is the structural unit shown below. TIFF2026026041000134.tif33101[In formula (a4-2), R 41 represents a hydrogen atom or a methyl group. L 43f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. R 43f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. However, L 43f and R 43f At least one of L has a fluorine atom, 43f and R 43f The maximum total number of carbon atoms is 21.
[0160] L 43f and R 43f Examples of the aliphatic hydrocarbon group in L include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these groups. 43f and R 43f Examples of the aliphatic hydrocarbon group in 43f and R 43f As long as the upper limit of the total number of carbon atoms in 42 Examples of the aliphatic hydrocarbon group include the same groups as the exemplified aliphatic hydrocarbon groups.
[0161] L 43f The aliphatic hydrocarbon group is preferably an alkanediyl group having 1 to 6 carbon atoms or a group represented by formula (L43f-1). TIFF2026026041000135.tif13120[In formula (L43f-1), s represents 0 or 1. L 45f and L 46f each independently represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may contain a fluorine atom. L 47f represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may contain a fluorine atom. X 46f and X 47f each independently represents -O-, -CO-, -CO-O- or -O-CO-. However, L 45f , L 46f , L 47f , X 46f and X 47f The total number of carbon atoms is 7 or less. * and ** are binding sites, and ** is -O-CO-R 43f ]
[0162] L in the group represented by formula (L43f-1) 45f , L 46f and L 47f Examples of the divalent aliphatic hydrocarbon group represented by include a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic hydrocarbon group, and a divalent aliphatic hydrocarbon group formed by combining an alkanediyl group with a divalent alicyclic hydrocarbon group. Specific examples include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group. Preferably, s is 0.
[0163] Examples of the group represented by formula (L43f-1) include the following groups: In the following examples, * and ** each represent a bonding site, and ** represents -O-CO-R 43f This is the binding site for TIFF2026026041000136.tif47140
[0164] R 43f is preferably an aliphatic hydrocarbon group having a fluorine atom. In this case, examples of the structural unit represented by formula (a4-2) include structural units represented by formula (a4-2A) or (a4-2B). TIFF2026026041000137.tif42157 [In formula (a4-2A) and formula (a4-2B), R 41 and L 43f represents the same as in formula (a4-2). R 43fA represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and containing a fluorine atom. A 43f represents a divalent aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. X 43 represents **-O-CO- or **-CO-O-, and ** represents A 43f represents the binding site with R 43fB represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms which may contain a fluorine atom. However, in formula (a4-2A), L 43f and R 43fA The total number of carbon atoms in formula (a4-2B) is 21 or less, and in formula (a4-2B), L 43f , A 43f , X 43 and R 43fB The total number of carbon atoms in A is 21 or less. 43f and R 43fB At least one of them has at least one fluorine atom.] R 43fA The aliphatic hydrocarbon group of R 42 Examples of the aliphatic hydrocarbon groups include the same aliphatic hydrocarbon groups as those exemplified above. R 43fA is preferably an alkyl group having 1 to 13 carbon atoms and containing a fluorine atom, a cycloalkyl group having 3 to 12 carbon atoms and containing a fluorine atom, or a group combining these, and *-(CF2) n43f-R 42’ (* represents the bonding site with the carbonyl group. n43f represents an integer of 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 preferred. A 43f and R 43fB The aliphatic hydrocarbon group of R in formula (a4) is as long as the upper limit of the number of carbon atoms permits. 42 Examples of the aliphatic hydrocarbon groups include the same aliphatic hydrocarbon groups as those exemplified above. A 43f is preferably a divalent chain hydrocarbon group which may have a fluorine atom, a divalent alicyclic hydrocarbon group, or a combination thereof, more preferably a divalent chain hydrocarbon group which has a fluorine atom, and even more preferably a fluorinated alkanediyl group having 1 to 6 carbon atoms. R 43fB The aliphatic hydrocarbon group which may have a fluorine atom is preferably a chain hydrocarbon group which may have a fluorine atom, an alicyclic hydrocarbon group or a group combining these, more preferably an alkyl group having 1 to 12 carbon atoms which may have a fluorine atom, a cycloalkyl group having 3 to 12 carbon atoms or a group combining these, and more preferably a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluoropropyl group, a ... More preferred are fluorinated alkyl groups such as nonafluorobutyl, butyl, perfluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, pentyl, hexyl, perfluorohexyl, heptyl, perfluoroheptyl, octyl, and perfluorooctyl groups, cyclopropylmethyl, cyclopropyl, cyclobutylmethyl, cyclopentyl, cyclohexyl, perfluorocyclohexyl, adamantyl, adamantylmethyl, adamantyldimethyl, norbornyl, norbornylmethyl, perfluoroadamantyl, and perfluoroadamantylmethyl groups.
[0165] In formula (a4-2B), *-A 43f -X 43 -R 43fB An example of a structure that the group represented by the formula (I) can take is the following structure (* indicates the bonding site with the carbonyl group). TIFF2026026041000138.tif15170
[0166] The structural unit represented by formula (a4-2A) includes the structural units shown below and R in the structural unit represented by formula (a4-2A) in the structural units shown below. 41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2026026041000139.tif99167
[0167] The structural unit represented by formula (a4-2B) includes the structural units shown below and R in the structural unit represented by formula (a4-2B) in the structural units shown below. 41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2026026041000140.tif111164
[0168] The structural unit (a4) also includes a structural unit represented by formula (a4-3). TIFF2026026041000141.tif3589[In formula (a4-3), R 41 represents a hydrogen atom or a methyl group. L 44f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may contain a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. R 44f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may contain a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. However, L 44f and R 44f At least one of L has a fluorine atom,44f and R 44f The maximum total number of carbon atoms is 21.
[0169] L 44f and R 44f Examples of the aliphatic hydrocarbon group in L include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these groups. 44f and R 44f Examples of the aliphatic hydrocarbon group in 44f and R 44f As long as the upper limit of the total number of carbon atoms in 42 Examples of the aliphatic hydrocarbon group include the same groups as the exemplified aliphatic hydrocarbon groups. L 44f is preferably an alkanediyl group having 1 to 14 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-), and -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -or-(CH2) j4 -CO-O-(CH2) j5 - (j1 to j5 each independently represent an integer of 1 to 6). Also preferred is an alkanediyl group having 1 to 4 carbon atoms (one -CH2- contained in the alkanediyl group may be replaced with -O-, and one -CH2-CH2- contained in the alkanediyl group may be replaced with -CO-O- or -O-CO-). R 44f is preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms and having a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms and having a fluorine atom, an alicyclic hydrocarbon group having 3 to 10 carbon atoms and having a fluorine atom, or a group combining these, further preferably an alkyl group having 1 to 10 carbon atoms and having a fluorine atom, and even more preferably an alkyl group having 1 to 6 carbon atoms and having a fluorine atom.
[0170] Examples of the structural unit represented by formula (a4-3) include the following structural units and structural units represented by the following formulas: 41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2026026041000142.tif86170
[0171] The structural unit (a4) also includes a structural unit represented by formula (a4-A). TIFF2026026041000143.tif3573[In formula (a4-A), R 44 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X 44 represents a single bond or *-CO-O-. * represents R 44 represents the bonding site with the carbon atom to which it is bonded. L 44 represents an aliphatic hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO- or -CO-. R 45 represents a fluorinated alkyl group having 1 to 8 carbon atoms. R 46 represents a hydrogen atom or a fluorinated alkyl group having 1 to 6 carbon atoms, and the fluorinated alkyl group is L 44 may bond to form an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-. mi represents an integer of 1 to 4. When mi is 2 or more, the groups in the parentheses may be the same or different.]
[0172] R 44 Examples of the halogen atom and the alkyl group optionally having a halogen atom in the formula (a1-0) to the formula (a1-2) include R a01 , R a4 and R a5 Examples include the same as those exemplified above. R 44 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, further preferably a hydrogen atom, a methyl gro...
Claims
1. A carboxylic acid generator containing a carboxylic acid salt represented by formula (I): [In formula (I), m10 represents an integer of 1 to 3, and when m10 is 2 or greater, the groups in the parentheses may be the same or different. m11 represents an integer of 0 to 2, and satisfies 2≦m10+m11≦3; when m10+m11=2, X represents an iodine atom; when m10+m11=3, X represents a sulfur atom; and when m11 is 2 or greater, the groups in parentheses may be the same as or different from each other. A 1 and A 2 each independently represents a single bond or a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 11 It may be replaced by - or -CO-. R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or a heterocyclic hydrocarbon group having 4 to 9 carbon atoms, and the aromatic hydrocarbon group and the heterocyclic hydrocarbon group may have a substituent. R 1 and R 4 are each independently a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 Represents. * indicates Ar 1 or Ar 2 represents the binding site with X 1 and X 2 each independently represents —CO—O—, —O—CO—, —O—CO—O— or —O—. L 11 represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 11 It may be replaced by - or -CO-. R 10 represents an acid labile group. R 2 and R 3 each independently represents a halogen atom or a hydrocarbon group having 1 to 28 carbon atoms, and the hydrocarbon group may have a substituent. 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 11 - or -CO-, and two R 2 , two R 3 or R 2 and R 3 is bonded, and X + may form a ring containing -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 11 - or -CO-, and two R 2 , two R 3 or R 2 and R 3 is X + and a single bond formed between two benzene rings connecting the two. m1 represents an integer of 1 to 5, and when m1 is 2 or more, the groups in the parentheses may be the same or different. mm1 represents an integer of 2 to 5, and a plurality of R 1 may be the same or different from each other. m2 represents an integer of 0 to 4, and satisfies 1≦m1+m2≦5. When m2 is 2 or more, a plurality of R 2 may be the same or different from each other. m3 represents an integer of 0 to 5, and when m3 is 2 or more, a plurality of R 3 may be the same or different from each other. m4 represents an integer of 0 to 5, satisfying 0≦m3+m4≦5, and when m4 is 2 or more, the groups in the parentheses may be the same or different. mm4 represents 0 or 1. X 0 represents a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -CO-, -SO-, -NR 11 -or-SO 2 - may be replaced by .
2. 2. The carboxylic acid generator according to claim 1, wherein the cation of the carboxylic acid salt represented by formula (I) is a cation represented by formula (IC-1). [In formula (IC-1), m10, m11, X, A 1 , Ar 1 , m1, R 2 , R 3 , m2 and m3 have the same meanings as in formula (I). R 1A and R 1B are each independently a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents X 1 , X 2 , L 11 and R 10 have the same meaning as in formula (I).
3. 2. The carboxylic acid generator according to claim 1, wherein m10 is 1 or 2.
4. 2. The carboxylic acid generator according to claim 1, wherein the cation of the carboxylate represented by formula (I) is one selected from the cations represented by formulas (IC-2) to (IC-10): [Formula (IC-2) to formula (IC-10), A 1 , Ar 1 , m3, R 2 and R 3 , have the same meaning as in formula (I). R 1A , R 1B and R 1C are each independently a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents X 1 , X 2 , L 11 and R 10 have the same meanings as in formula (I). X 7 is a single bond, -CH 2 -, -O-, -S-, -CO-, -SO-, -NR 11 -or-SO 2 - represents.
5. A 1 But, **-X 01 -L 01 - or **-L 01 -X 01 - and X 01 is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 represents -, L 01 is a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and —CH 2 - is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 - may be replaced by . ** is Ar 1 The carboxylic acid generator according to claim 1 , wherein the bonding site is
6. L 01 is a single bond or an alkanediyl group having 1 to 6 carbon atoms (the —CH 2 6. The carboxylic acid generator according to claim 5, wherein - may be replaced by -O- or -CO-.
7. R 1 is a hydroxy group, *—O—R 10 or *-O-L 11 -CO-O-R 10 (* indicates Ar 1 The carboxylic acid generator according to claim 1, wherein
8. R 1 But *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 and R 10 2. The carboxylic acid generator according to claim 1, wherein the acid labile group is a group represented by formula (1a) or a group represented by formula (2a). [In formula (1a), R aa1 , R aa2 and R aa3 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded, and R aa3 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, and the alkyl group, alkenyl group, alicyclic hydrocarbon group, and aromatic hydrocarbon group may contain a halogen atom. * indicates a binding site.] [In formula (2a), R aa1’ and R aa2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R aa3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa1’ represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R aa2’ and R aa3’ are bonded to each other and bonded to -C-X a Together with —, it forms a heterocyclic group having 3 to 20 carbon atoms, and —CH contained in the hydrocarbon group and the heterocyclic group 2 - may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom. X a represents an oxygen atom or a sulfur atom. * indicates a binding site.]
9. 2. The carboxylic acid generator according to claim 1, wherein X is a sulfur atom.
10. Ar 1 2. The carboxylic acid generator according to claim 1, wherein is a group derived from a benzene ring, a naphthalene ring, a furan ring, or a thiophene ring.
11. X 0 but, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group comprising a combination of a chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms, The alicyclic hydrocarbon group, the chain hydrocarbon group, and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group, and the —CH 2 - is -O-, -S-, -CO-, -SO-, -NR 11 -or-SO 2 The carboxylic acid generator according to claim 1, wherein - may be replaced by .
12. X 0 The carboxylic acid generator according to claim 11, wherein is a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a hydroxy group.
13. A resist composition comprising the carboxylic acid generator according to any one of claims 1 to 12 and an acid generator other than said carboxylic acid generator.
14. 14. The resist composition according to claim 13, wherein the acid generator comprises a salt represented by formula (B1) or a salt represented by formula (B2). [In formula (B1), L b1 represents a single bond or an (nb1+1)-valent hydrocarbon group which may have a substituent, and —CH 2 - is -O-, -S-, -CO-, -SO- 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 —CH 2 - is -O-, -S-, -CO-, -SO- or -SO 2 It may be replaced with -. Y b1 represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and —CH 2 - is -O-, -S-, -SO 2 It may be replaced by --, --SO-- 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. Z1 + represents an organic cation. [In formula (B2), A 1 represents a nitrogen atom or a carbon atom. L b2’ represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -CO-, -SO- or -SO 2 It may be replaced with -. Y b1’ represents a methyl group which may have a substituent or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -CO-, -SO- or -SO 2 It may be replaced with -. nb5 represents an integer of 2 or 3. When nb5 is 2, A 1 is a nitrogen atom, and nb5 is 3, then A 1 is a carbon atom. The groups in the parentheses may be the same or different, and two groups in the parentheses are bonded to form A 1 may form a ring containing: Z2 + represents an organic cation.
15. Further, the composition contains a resin containing a structural unit having an acid labile group, The resist composition according to claim 13, wherein the structural unit having an acid labile group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), 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 group formed by combining these, 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 contain 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 —CH 2 - represents -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 —CO—. 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 a34 represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R a35 and R a36 are bonded to each other to form a divalent heterocyclic group having 3 to 20 carbon atoms together with the —C—O— to which they are bonded, 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 one or more halogen atoms, 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 a ring having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded, and R a64 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. X a61 represents a single bond, —CO—O—*, or —CO—NR a65 - represents *, * represents the 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-O-L 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.]
16. The resist composition according to claim 13, further comprising a resin containing 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 —CH 2 - represents -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.
17. (1) a step of applying the resist composition according to claim 13 onto a substrate; (2) drying the applied resist composition to form a composition layer; (3) exposing the composition layer to light; (4) a step of heating the composition layer after exposure; and (5) developing the composition layer after heating; A method for producing a resist pattern comprising:
18. A carboxylic acid salt represented by formula (I): [In formula (I), m10 represents an integer of 1 to 3, and when m10 is 2 or greater, the groups in the parentheses may be the same or different. m11 represents an integer of 0 to 2, and satisfies 2≦m10+m11≦3; when m10+m11=2, X represents an iodine atom; when m10+m11=3, X represents a sulfur atom; and when m11 is 2 or greater, the groups in parentheses may be the same as or different from each other. A 1 and A 2 each independently represents a single bond or a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 11 It may be replaced by - or -CO-. R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or a heterocyclic hydrocarbon group having 4 to 9 carbon atoms, and the aromatic hydrocarbon group and the heterocyclic hydrocarbon group may have a substituent. R 1 and R 4 are each independently a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 Represents. * indicates Ar 1 or Ar 2 represents the binding site with X 1 and X 2 each independently represents —CO—O—, —O—CO—, —O—CO—O— or —O—. L 11 represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 11 It may be replaced by - or -CO-. R 10 represents an acid labile group. R 2 and R 3 each independently represents a halogen atom or a hydrocarbon group having 1 to 28 carbon atoms, and the hydrocarbon group may have a substituent. 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 11 - or -CO-, and two R 2 , two R 3 or R 2 and R 3 is bonded, and X + may form a ring containing -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 11 - or -CO-, and two R 2 , two R 3 or R 2 and R 3 is X + and a single bond formed between two benzene rings connecting the two. m1 represents an integer of 1 to 5, and when m1 is 2 or more, the groups in the parentheses may be the same or different. mm1 represents an integer of 2 to 5, and a plurality of R 1 may be the same or different from each other. m2 represents an integer of 0 to 4, and satisfies 1≦m1+m2≦5. When m2 is 2 or more, a plurality of R 2 may be the same or different from each other. m3 represents an integer of 0 to 5, and when m3 is 2 or more, a plurality of R 3 may be the same or different from each other. m4 represents an integer of 0 to 5, satisfying 0≦m3+m4≦5, and when m4 is 2 or more, the groups in the parentheses may be the same or different. mm4 represents 0 or 1. X 0 represents a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH 2 - is -O-, -S-, -CO-, -SO-, -NR 11 -or-SO 2 - may be replaced by .
Citation Information
Patent Citations
Carboxylate, carboxylic acid generator, resist composition, and method for producing resist pattern
JP2022164584A