Resist composition, method for producing resist pattern, compound, and resin
The resist composition with a resin of specific structural units addresses poor CD uniformity in resist patterns by enhancing chemical bonding and acid generation, resulting in improved pattern consistency.
Patent Information
- Application Number
- JP2025128776
- 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 resist patterns with poor CD uniformity.
A resist composition containing a resin with specific structural units, including a compound represented by formula (IP), which enhances CD uniformity through controlled chemical bonding and acid generation.
The resist composition achieves improved CD uniformity in resist patterns, ensuring consistent and precise pattern formation.
Smart Images

Figure 2026026043000001 
Figure 2026026043000002 
Figure 2026026043000003
Abstract
Description
[Technical Field]
[0001] The present invention relates to a compound, a resin containing a structural unit derived from the compound, a resist composition containing the resin, and a method for producing a resist pattern using the resist composition. [Background technology]
[0002] Patent Document 1 describes a resist composition containing a resin that includes a structural unit derived from a compound of the following structural formula: TIFF2026026043000001.tif4085 [Prior art documents] [Patent documents]
[0003] [Patent Document 1] Patent Publication No. 2021-130807 Summary of the Invention [Problem to be solved by the invention]
[0004] An object of the present invention is to provide a resist composition that forms a resist pattern that has better CD uniformity (CDU) than a resist pattern formed from a resist composition that contains a resin that includes a structural unit derived from the above compound. [Means for solving the problem]
[0005] The present invention includes the following inventions. [1] A resist composition containing a resin containing a structural unit represented by formula (IP). TIFF2026026043000002.tif6287[In formula (IP), R 0 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X 10 is a single bond, or -O-, -CO-, -S-, -SO-, -SO2-, -NR 5represents -, a phenylene group which may have a substituent, or a group in which these are combined. R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 2 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or a heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms which may have a substituent. A 1 represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a substituent, and -CH2- contained in the hydrocarbon group is not limited to -O-, -CO-, -S-, -SO-, -NR 11 It may be replaced by - or -SO2-. R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or a heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms. R 1 is a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents Ar 1 is a group derived from a benzene ring, two or more R 1 At least two R 1 does not substitute adjacently with a group derived from a benzene ring. X 1 and X 2 each independently represents *-CO-O-, *-O-CO-, *-O-CO-O- or *-O-. R 10 represents an acid labile group. 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-. mm1 represents an integer of 2 to 5, and multiple R 1 may be the same or different from each other. R 4 represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group optionally having a substituent, and -CH2- contained in the haloalkyl group or the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 11 It may be replaced by - or -SO2-. m4 represents an integer of 0 to 3, and when m4 is 2 or more, a plurality of R 4 may be the same or different from each other. mm2 represents an integer of 1 to 5, and when mm2 is an integer of 2 or greater, the groups in the parentheses may be the same or different. [2] X 10 is a single bond or a group of the formula (X 10 -1)~Formula(X 10 The resist composition according to [1], wherein the group is a group represented by any one of the following: TIFF2026026043000003.tif45170[expression(X 10 -1)~Formula(X 10 -10) Medium, *, ** are binding sites, * is R 0 represents the bonding site with the carbon atom to which it is attached. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4. When mx is 2 or greater, multiple Rx's may be the same or different. X 20 is -O- or -NR 5 - represents. R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.] [3] X 10 is a single bond or a group of the formula (X 10 -1') and formula (X 10 -3')~expression(X 10 -10')。 [1] or [2], wherein the resist composition is a group represented by any one of [1] and [2]. TIFF2026026043000004.tif47123[formula(X 10 -1') and formula (X 10 -3')~expression(X 10 -10') medium, * and ** represent binding sites, * represents R 0 represents the bonding site between the carbon atom and the atom. [4] 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 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 not limited to -O-, -CO-, -S-, -SO-, -NR 11 - or -SO2- may be replaced. *** is Ar 1 The resist composition according to any one of [1] to [3], wherein the bond site is [5] X 01 The resist composition according to [4], wherein is —O—, —CO—, or —S—. [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 resist composition according to any one of [1] to [6], wherein [8] R 10 The resist composition 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). TIFF2026026043000005.tif2255[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.] TIFF2026026043000006.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] Ar 1 is a group derived from a benzene ring.
[10] The resist composition according to any one of [1] to [9], further comprising an acid generator, wherein the acid generator comprises a salt represented by formula (B1) or a salt represented by formula (B2). TIFF2026026043000007.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 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-, -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. TIFF2026026043000008.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 when nb5 is 3, 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 A1 may form a ring containing: Z2 + represents an organic cation.
[11] The resist composition according to any one of [1] to
[10] , wherein the resin 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). TIFF2026026043000009.tif44145 [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. TIFF2026026043000010.tif32119[In formula (a1-4), R a1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a17 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group. A a11 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group is -O-, -CO- or -NR a18 - may be replaced with R a18 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a1 represents a single bond or a carbonyl group. R a34 and R a35 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a36 represents a hydrocarbon group having 1 to 20 carbon atoms, or R 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. TIFF2026026043000011.tif4558[In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom. Z a1 is a single bond or -(CH2) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, * represents L 51 represents the binding site with L 51 , L 52 , L 53 and L 54 each independently represents -O- or -S-. s1 represents an integer of 1 to 3. s1' represents an integer of 0 to 3. TIFF2026026043000012.tif3781[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.]
[12] The resist composition according to any one of [1] to
[11] , wherein the resin contains a structural unit represented by formula (a2-A). TIFF2026026043000013.tif30127[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.
[13] The resist composition according to any one of [1] to
[12] , wherein the resin contains the structural unit represented by the above formula (a1-6) and the structural unit represented by the formula (a2-A).
[14] The resist composition according to any one of
[10] to
[13] , further comprising a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator.
[15] (1) A step of applying the resist composition according to any one of [1] to
[14] 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) A method for producing a resist pattern, comprising the step of developing the composition layer after heating.
[16] A resin containing a structural unit represented by the above formula (IP).
[17] A compound represented by formula (I): TIFF2026026043000014.tif43100 [In formula (I), all symbols have the same meanings as defined above.] [Effects of the Invention]
[0006] By using the resist composition of the present invention, a resist pattern with good CD uniformity (CDU) can be produced. DETAILED DESCRIPTION OF THE INVENTION
[0007] In this specification, "(meth)acrylic monomer" means "at least one of an acrylic monomer and a methacrylic monomer." The terms "(meth)acrylate" and "(meth)acrylic acid" have the same meaning. 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 XWhen 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 "solid content of the resist composition" refers to the sum of all components in the resist composition excluding the solvent (E), which will be described later.
[0008] [Resist Composition] The resist composition of the present invention contains a resin containing a structural unit represented by formula (IP) (hereinafter sometimes referred to as "structural unit (IP)"). The structural unit (IP) is derived from a compound represented by formula (I) (hereinafter sometimes referred to as "compound (I)"). The resist composition of the present invention may further contain an acid generator (hereinafter sometimes referred to as "acid generator (B)"), a resin other than the resin containing the structural unit (IP), a quencher such as a salt that generates an acid with a weaker acidity than the acid generated from the acid generator (hereinafter sometimes referred to as "quencher (C)"), etc. Examples of resins other than the resin containing the structural unit (IP) 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). The resist composition of the present invention preferably contains a solvent (hereinafter, may be referred to as "solvent (E)").
[0009] <Structural Unit (IP)> The structural unit (IP) is CH2=CR contained in compound (I). bb1 This shows the state in which the double bond is cleaved. TIFF2026026043000015.tif53132 [In formula (I), all symbols have the same meanings as defined above.]
[0010] In formula (I), R 0 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkyl group having 1 to 6 carbon atoms and containing a halogen atom include haloalkyl groups having 1 to 6 carbon atoms, such as fluorinated alkyl groups having 1 to 6 carbon atoms, chlorinated alkyl groups having 1 to 6 carbon atoms, brominated alkyl groups having 1 to 6 carbon atoms, and iodinated alkyl groups having 1 to 6 carbon atoms. Examples of the haloalkyl group include perfluoroalkyl groups having 1 to 6 carbon atoms (such as trifluoromethyl, pentafluoroethyl, heptafluoropropyl, and nonafluorobutyl groups), 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and 3,3,4,4,4-pentafluorobutyl groups, chloromethyl, bromomethyl, and iodomethyl groups. R 5 and R 0 The alkyl group having 1 to 6 carbon atoms 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, and a hexyl group. R 5 and R 0 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, even more preferably a hydrogen atom or a methyl group, and still more preferably a methyl group. X10 represents a single bond, -O-, -CO-, -NR 5 -, a phenylene group which may have a substituent, or a group in which these are combined is preferred, and a single bond, *-O-**, *-CO-**, *-CO-O-**, *-O-CO-O-**, *-CO-NR 5 -**, *-NR 5 -CO-O-**, *-O-CO-NR 5 It is more preferable that it is -** or *-Ax-Ph-Ay-**. In the above groups, * and ** represent binding sites, * represents R 0 represents a bonding site with the carbon atom to which Ax and Ay are bonded. Ax and Ay each independently represent one or more bonding types selected from the group consisting of a single bond, an ether bond, a thioether bond, an amide bond, an ester bond, and a carbonate ester bond. Ph represents a phenylene group which may have a substituent. X 10 is a group represented by *-Ax-Ph-Ay-**, it is preferably a linking group represented by the following formula (X10). TIFF2026026043000016.tif3449[In formula (X10), Ax and Ay have the same meanings as above. Ax is R 0 represents a bond species that bonds with the carbon atom to which Ar is attached, and Ay represents a bond species that bonds with the carbon atom to which Ar is attached. 2 represents a bonded species that bonds with Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4, and when mx is an integer of 2 or greater, multiple Rx's may be the same or different. When either Ax or Ay is a single bond, the other is preferably one or more bonds selected from the group consisting of an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond. The bonding position of Ay in the phenylene group is preferably the m-position or p-position relative to the bonding position of Ax, and more preferably the p-position. Rx is preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, or an ethyl group. mx is preferably 0, 1 or 2. X 10 Examples of the group include a single bond or the group represented by the following formula (X 10 -1)~Formula(X 10 -10). * and ** represent a bonding site, * represents R 0 represents the bonding site with the carbon atom to which X is attached. 20 is -O- or -NR 5 - represents. TIFF2026026043000017.tif45170[expression(X 10 -1)~Formula(X 10 -10) In the above, all symbols have the same meaning as above. Expression(X 10 -1)~Formula(X 10 Specific examples of the group represented by -10) include the following groups: TIFF2026026043000018.tif79161Among them, X 10 is a single bond or a group of the formula (X 10 -1') and formula (X 10 -3')~expression(X 10 -10'), and is preferably a single bond or a group represented by the formula (X 10 -1), formula (X 10 -4'), expression (X 10 -5'), expression (X 10 -6') and formula (X 10 -10'), and more preferably a single bond, a group represented by the formula (X 10 -1'), a group represented by the formula (X 10 -5') or a group represented by the formula (X 10 -6') is more preferred.
[0011] 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 Ar2 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 is preferably a group derived from a benzene ring, a naphthalene ring, a furan ring, or a thiophene ring, more preferably a group derived from a benzene ring or a naphthalene ring, and even more preferably a group derived from a benzene ring. Ar 2 is preferably a group derived from a benzene ring, a naphthalene ring, a furan ring, or a thiophene ring, more preferably a group derived from a benzene ring or a naphthalene ring, and even more preferably a group derived from a benzene ring. Each of the above groups may have a substituent. Ar 2 The substituents that may be possessed by R 4 The same groups as those shown below can be mentioned.
[0012] A 1 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. TIFF2026026043000019.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.
[0013] 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-.
[0014] A 1 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 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 -), 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 ...oxycarbonyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyloxycarbonyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyloxycarbonyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyloxycarbonyl group in which -CH2- at any position is replaced with -CO-O-), an alkanediyloxycarbonyl group (an alkanediyloxycarbonyl group in which -CH2- at any position is replaced with -CO-O carbonyloxy group (a group in which -CH2-CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-O-), alkanediylsulfonyl group (a group in which -CH2- at any position in an alkanediyl group is replaced with -SO2-), alkanediylthio group (a group in which -CH2- at any position in an alkanediyl group is replaced with -S-), alkanediylamino group (a group in which -CH2- 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 19 carbon atoms, such as a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 19 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 20 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 19 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 18 carbon atoms, such as a butoxycarbonyloxy group. Examples of alkoxyalkoxy groups include alkoxyalkoxy groups having 2 to 18 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 alkylthio group include alkylthio groups having 1 to 19 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 19 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 19 carbon atoms, such as methylamino, ethylamino, dimethylamino, propylamino, butylamino, pentylamino, and hexylamino groups. 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 19 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 alkoxyalkyl group include alkoxyalkyl groups having 2 to 19 carbon atoms, such as a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an ethoxyethyl group, etc. 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 19 carbon atoms, such as a hydroxymethyl group, a dihydroxymethyl group, a hydroxyethyl group, a dihydroxyethyl group, a hydroxypropyl group, etc. 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 still more preferably 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 19 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 19 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 20 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 19 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. Examples of the alkanediyloxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 18 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 still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. 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 still more preferably 2 or 3. Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 19 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 19 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alkanediylamino group include alkanediylamino groups having 1 to 19 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 19 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 19 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 19 carbon atoms, such as a cyclohexylmethoxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 19 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 19 carbon atoms, such as a phenyloxy group.
[0015] In addition, -CH2- contained in an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these may be replaced with -O-, -CO-, -S-, -NR 11Examples of the group substituted with -, -SO- or -SO2- include the groups shown below. In addition, among the groups shown below, -O- is -S-, and -CO- is -NR 11 Also included are groups substituted with -, -SO-, and -SO2-. The binding site can be at any position. TIFF2026026043000020.tif89165
[0016] A 1 The substituents that the hydrocarbon group may have include R 4 The same groups as those shown below can be mentioned. A 1 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-, -NR 11 -, -SO-, or -SO2-, provided that at least one of -CH2- contained in the hydrocarbon group is replaced by -O-, -CO-, -S-, or -NR2-. 11 -, -SO- or -SO2- are preferred. 1 is***-L 011 -X 01 -L 012 -is (X 01 -O-, -CO-, -S-, -NR 11 -, -SO- or -SO2-. 011 and L 012 each independently 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 -O-, -CO-, -S-, -NR 11 may be replaced by -, -SO- or -SO2-. 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-O-, -CO-, -S-, -NR 11 -, -SO- 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 -O-, -CO-, -S-, -NR 11 It may be replaced by -, -SO- or -SO2-. *** represents Ar 1 It is more preferable that A 1 -O-, -CO-, -S-, -NR 11 Those having no substituents other than the -, -SO- or -SO2- substitutions are also preferred. L 011 , L 012 and L 01 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-, -NR 11 -, -SO- or -SO2-) is a group having 1 to 18 carbon atoms, 1 Examples of the groups include the same groups as those listed in the above. X 01 -O-, -CO-, -S-, -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 an integer of -O-, -CO-, -S-, -NR 11 -, -SO-, or -SO2-), and a single bond or a hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S-, -NR 11-, -SO- 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 (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -CO-, -S-, -NR 11 -, -SO-, 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. Also, A 1 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 (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 -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 Ar 2 The bonding position to Ar may be anywhere. 2 is a group derived from a benzene ring, X 10 The bonding positions of Ar may be either o-position, m-position or p-position, but at least one of them is preferably bonded to the p-position or m-position, more preferably to the m-position. 2 is a group derived from a naphthalene ring, for example, X 10 When the bonding position of is 1, it may be any of 2 to 8 positions. 10 When the bonding position of X is the 2nd position, it may be the 1st position or any of the 3rd to 8th positions. 10 When the bonding position of X is the 1st position, it is preferable that at least one of X is bonded to the 3rd to 6th positions. 10 When the bonding position is the 2nd position, it is preferable that at least one of them is bonded to the 4th to 7th positions.
[0017] R 1 X included in 1 is preferably *-CO-O-, *-O- or *-O-CO-O-, more preferably *-CO-O- or *-O- (where * is Ar 1 or L 11 represents the binding site with ). R 1 X included in 2 is preferably *-CO-O-, *-O-CO- or *-O-, more preferably *-CO-O- or *-O- (* is Ar 1 represents the binding site with ).
[0018] R 1 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)"). TIFF2026026043000021.tif2255 [In formula (1a), all symbols have the same meanings as defined above.] TIFF2026026043000022.tif2262 [In formula (2a), all symbols have the same meanings as defined above.]
[0019] R aa1 , R aa2 and R aa3 Examples of the alkyl group of R include a methyl group, an ethyl group, a propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group. aa1 , R aa2 and R aa3 The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms. R aa1 , 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 aa3The 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. TIFF2026026043000023.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.
[0020] 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.
[0021] 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-. TIFF2026026043000024.tif26136
[0022] The group represented by formula (1a) is a 1,1,1-trialkyl group (R aa1 , R aa2 and R aa3 is an alkyl group, preferably a tert-butyl group), a 2-alkyladamantan-2-yl group (in formula (1a), R aa1 , R aa2 and the carbon atoms to which they are bonded form an adamantyl group, and R aa3 is an alkyl group) and 1-(adamantan-1-yl)-1,1-dialkyl groups (in formula (1a), R aa1 and R aa2 is an alkyl group, and R aa3 is an adamantyl group).
[0023] 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. TIFF2026026043000025.tif22142R aa1' 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.
[0024] Specific examples of the acid labile group (1a) include the following groups: * represents a bonding site. TIFF2026026043000026.tif60156
[0025] Specific examples of the acid labile group (2a) include the following groups: * represents a bonding site. TIFF2026026043000027.tif59148
[0026] R 1 L included in 11 Examples 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 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, 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. TIFF2026026043000028.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 is 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 preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms. Examples of the group combining two or more groups include a group combining an alicyclic hydrocarbon group with an alkanediyl group, a group combining an aromatic hydrocarbon group with an alkanediyl group, 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 types of each of the alicyclic hydrocarbon group, aromatic hydrocarbon group, and chain hydrocarbon group may be combined. In addition, when any group is X1 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 -NR11 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 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), 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. 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 11 The group substituted with - or -SO2- includes the same groups as those exemplified in this specification, within the upper limit of the carbon number.
[0027] 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 The -CH2- contained in the chain hydrocarbon group such as the alkyl group contained in 11 - 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. L 11The 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.
[0028] Ar 1 is a group derived from a benzene ring, R 1 Ar 1 The binding position to A 1 The bonding position of A may be either o-position, m-position or p-position. 1 It is preferable that at least one of the groups is bonded to the o- or m-position relative to the bonding position of R. However, when mm1 is 2 or more, 1 At least two R 1 does not permute adjacently. In particular, when m4 is 0, two R 1 Ar 1 The binding position to A 1When m4 is 1 or more, at least one R 1 is preferably attached to the o-position. 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 is the 2nd position, it is preferable that at least one of them is bonded to the 4th to 7th positions. R 1 is 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:
[0029] R 4 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 4The haloalkyl group having 1 to 12 carbon atoms refers to an alkyl group having 1 to 12 carbon atoms and containing a halogen atom, and examples thereof include 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 the haloalkyl group include a perfluoroalkyl group having 1 to 12 carbon atoms (e.g., 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 number of carbon atoms in the haloalkyl group is preferably 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. R 4 Examples of the hydrocarbon group having 1 to 18 carbon atoms include chain hydrocarbon groups such as alkyl groups and alkanediyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups. The alkyl group is a linear or branched alkyl group, and examples thereof include 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. TIFF2026026043000029.tif42165Specifically, monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl. 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.
[0030] 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 may be bound to
[0031] R 4The haloalkyl group or hydrocarbon group represented by the formula (I) is -O-, -CO-, -S-, -SO-, -NR 11 When the haloalkyl group is substituted with - or -SO2-, the number of carbon atoms before the substitution is the total number of carbon atoms in the haloalkyl group or hydrocarbon group, and the number may be one or more. The -CH2- contained in the haloalkyl group and the hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 11 Examples of groups substituted for - or -CO- 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 alkanediyl ... Examples of the substituted group include an alkanediyl 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, a haloalkoxy group, a haloalkoxycarbonyl group, a haloalkylcarbonyl group, a haloalkylcarbonyloxy group, and a group combining two or more of these groups. Examples of the substituted group include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. Examples of the haloalkoxy group, haloalkoxycarbonyl group, haloalkylcarbonyl group, and haloalkylcarbonyloxy group include haloalkoxy groups having 1 to 11 carbon atoms, haloalkoxycarbonyl groups having 2 to 11 carbon atoms, haloalkylcarbonyl groups having 2 to 12 carbon atoms, and haloalkylcarbonyloxy groups having 2 to 11 carbon atoms, and include groups in which one or more hydrogen atoms of the above-exemplified groups have been replaced with a halogen atom. 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.
[0032] R 4 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 the same groups as those mentioned above. The hydrocarbon group may have one or more substituents. R 4 is within the range allowed by the upper limit of the carbon number, *-X 1 -R 10 , *-X 2 -L 11 -X 1 -R 10 may be. R 4 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 10is preferred, a fluorine atom, an iodine atom, a haloalkyl group of 1 to 6 carbon atoms, or an alkyl group of 1 to 6 carbon atoms (-CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), is more preferred, a fluorine atom, an iodine atom, a haloalkyl group of 1 to 4 carbon atoms, or an alkyl group of 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), is even more preferred, a fluorine atom, iodine atom, a hydroxy group, a carboxy group, an alkyl group of 1 to 4 carbon atoms, a fluorinated alkyl group of 1 to 4 carbon atoms, or an alkoxy group of 1 to 3 carbon atoms, is even more preferred, a fluorine atom, iodine atom, a hydroxy group, a carboxy group, an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or an alkoxy group of 1 to 3 carbon atoms, is even more preferred, and a fluorine atom, iodine atom, a trifluoromethyl group, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a carboxy group, or a hydroxy group. R 4 Ar 1 The bonding position to Ar is not particularly limited. 1 is a group derived from a benzene ring, R 4 Ar 1 The binding position to A 1 It may be at the o-position, m-position, or p-position relative to the bonding position of R 4 is A 1 When m4 is 2, R 4 is A 1 With respect to the bonding positions of R, 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. 4 is 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 1 When the bonding position of is the 1st position, it may be any of the 2nd to 8th positions. 1When 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 is the 2nd position, it is preferable that at least one of them is bonded to the 4th to 7th positions. mm1 is preferably 2, 3 or 4, more preferably 2 or 3, and even more preferably 2. Preferably, m4 is 0, 1 or 2. mm2 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, even more preferably 1 or 2, and even more preferably 1.
[0033] Compound (I) includes compounds represented by the following formula: In the following compounds, R of compound (I) 0 and a structural unit in which a hydrogen atom corresponding to the following formula is replaced with a methyl group or the like, and a structural unit in which a methyl group is replaced with a hydrogen atom or the like, can be given as specific examples of compound (I). TIFF2026026043000030.tif244161
[0034] TIFF2026026043000031.tif252160
[0035] TIFF2026026043000032.tif246158
[0036] TIFF2026026043000033.tif230162
[0037] <Method for producing compound (I)> Compound (I) can be produced by reacting a compound represented by formula (Ia) with a compound represented by formula (Ib) in a solvent in the presence of a catalyst, and optionally treating with an acid. TIFF2026026043000034.tif62153 [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. Examples of the compound represented by formula (Ia) include compounds represented by the following formula, which are readily available on the market and can also be easily produced by known production methods. TIFF2026026043000035.tif31151
[0038] Examples of the compound represented by formula (Ib) include compounds represented by the following formula, which are readily available on the market and can also be easily produced by known production methods. TIFF2026026043000036.tif110161
[0039] [Resin containing structural unit (IP) derived from compound (I)] The resin of the present invention is a resin containing a structural unit (IP). The resin may be a homopolymer containing one type of structural unit (IP), or a copolymer containing two or more types of structural units (IP). The resin may also contain structural units other than the structural unit (IP). As described below, structural units other than the structural unit (IP) include structural units having an acid labile group (hereinafter sometimes referred to as "structural unit (a1)") and structural units other than structural units having an acid labile group. As structural units other than structural units having an acid labile group, structural units not having an acid labile group (hereinafter sometimes referred to as "structural unit (s)") and structural units known in the art may be mentioned. The content of the structural unit (IP) relative to all structural units in the resin may be 0.1 mol% or more, preferably 0.5 mol% or more, more preferably 0.8 mol% or more, even more preferably 1 mol% or more, still more preferably 2 mol% or more, even more preferably 3 mol% or more, and even more preferably 5 mol% or more. It may also be 100 mol% or less, preferably 50 mol% or less, more preferably 30 mol% or less, even more preferably 20 mol% or less, and even more preferably 15 mol% or less. Specifically, it may be 0.1 to 100 mol%, preferably 1 to 100 mol%, more preferably 2 to 100 mol%, and even more preferably 3 to 100 mol%. The resin preferably further contains the structural unit (a1) in addition to the structural unit (IP). Regardless of whether or not the structural unit (IP) is contained, the resin may be referred to as a resin containing the structural unit (a1) (hereinafter, may be referred to as "resin (A)").
[0040] <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)). TIFF2026026043000037.tif2298[In formula (1), R a1 , R a2 and R a3each 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.] TIFF2026026043000038.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.]
[0041] R a1 , R a2 and R a3 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. R a1 , R a2 and R a3 Examples of the alkenyl group in the formula (I) include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. Ra1 , 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. TIFF2026026043000039.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-. TIFF2026026043000040.tif28138
[0042] 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. TIFF2026026043000041.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.
[0043] 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. TIFF2026026043000042.tif149165
[0044] Specific examples of group (2) include the following groups: * represents a binding site. TIFF2026026043000043.tif55153
[0045] 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. 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.
[0046] 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. TIFF2026026043000044.tif44144 [In formula (a1-0), formula (a1-1), and formula (a1-2), all symbols have the same meanings as defined above.]
[0047] 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 a5 Examples 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 any one of 1 to 4, more preferably 1), and more preferably an oxygen atom. R a02 , R a03 , R a04 , R a6 and R a7 The alkyl group, alkenyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group and combinations thereof in the formula (1) include R a1 , R a2 and R a3 Examples of the groups include the same groups as those listed in the above. R a02 , R a03 , and R a04 The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a6 and R a7 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 , Ra04 , 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 a7 is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkenyl group having 2 to 6 carbon atoms which may have a halogen atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, more preferably a methyl group, 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.
[0048] 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. TIFF2026026043000045.tif118160
[0049] 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. TIFF2026026043000046.tif34170
[0050] 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. TIFF2026026043000047.tif92164
[0051] 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%.
[0052] 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)"). TIFF2026026043000048.tif32119 [In formula (a1-4), all symbols have the same meanings as defined above.] 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 Examples of the halogen atom include the same as those exemplified as the halogen atom and the alkyl group optionally having a halogen atom in the above. 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 a17The 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 a17 is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 4 carbon atoms or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group or an ethoxyethoxy group.
[0053] A a11Examples 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. In addition, 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. A a11 -CH2- in the alkanediyl group is -O-, -CO- or -NR a18Examples of the group substituted for - 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, an alkanediylamino group, etc. 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. A 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. mc is preferably 0 or 1.
[0054] 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): TIFF2026026043000049.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 TIFF2026026043000050.tif15104
[0055] 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. na1 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. na11 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. mc is preferably 0 or 1.
[0056] -OC(R a34 )(R a35 )-OR a36is 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 a11 It 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.
[0057] 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). TIFF2026026043000051.tif221164
[0058] 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%.
[0059] 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)"). TIFF2026026043000052.tif4558 [In formula (a1-5), all symbols have the same meanings as defined above.]
[0060] 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 Examples of the halogen atom include the same as those exemplified as the halogen atom and the alkyl group optionally having a halogen atom in the above. In formula (a1-5), R a8 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. L 51 is preferably an oxygen atom. L 52 and L 53 Among these, it is preferred that one is —O— and the other is —S—. s1 is preferably 1. s1' is preferably an integer of 0 to 2. Z a1 is preferably a single bond or —CH2—CO—O—.
[0061] 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 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%.
[0062] 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)"). TIFF2026026043000054.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 a01Examples of the halogen atom include the same as those exemplified as the halogen atom and the alkyl group optionally having a halogen atom in the above. 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 )(Ra63 )(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. TIFF2026026043000055.tif33107
[0063] 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.
[0064] 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 a17Examples 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.
[0065] 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 a methyl group corresponding to the following is replaced with a hydrogen atom: TIFF2026026043000056.tif227165
[0066] 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%.
[0067] Further, examples of the structural unit (a1) include the following structural units. When resin (A) contains structural units represented by formulas (a1-7-1) to (a1-7-7), 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 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 %.
[0068] 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 %.
[0069] <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.
[0070] <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. TIFF2026026043000059.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 is R in formula (a1-0) 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.
[0071] 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, a21 Examples of the alkanediyl groups include the same alkanediyl groups as those shown in the above. A a21is 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.
[0072] 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. TIFF2026026043000060.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, even more preferably 3 to 12 carbon atoms, still 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 a28 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 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-NRa28 -), 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.
[0073] 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 upper limit of the carbon number. 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.
[0074] 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. TIFF2026026043000061.tif66168
[0075] 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.
[0076] In the structural unit (a2), L a21 is a cyclic hydrocarbon group, and examples of the structural unit having a phenolic hydroxy group or a carboxy group include a structural unit represented by formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A)"). TIFF2026026043000062.tif30127 [In formula (a2-A), all symbols have the same meanings as defined above.]
[0077] 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.
[0078] 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. TIFF2026026043000063.tif189170
[0079] When the structural unit (a2-A) is contained in the resin (A), the content of the structural unit (a2-A) relative to all structural units is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 15 mol% or more, and still more preferably 20 mol% or more. It is also preferably 80 mol% or less, more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, even more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%. The structural unit (a2-A) 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).
[0080] 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)"). TIFF2026026043000064.tif45100[In formula (a2-B) and formula (a2-C), R a2 has the same meaning as formula (a2). R a27 has the same meaning as formula (a2-A). L a25is -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 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. 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.
[0081] 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 is 1 mol% or more, preferably 2 mol% or more, based on the total structural units of the resin (A). 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%.
[0082] TIFF2026026043000066.tif51107[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). Ra21 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 a22 As 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.
[0083] 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)"). TIFF2026026043000067.tif51109[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.
[0084] Examples of the structural unit (a2-D) include the structural units shown below. TIFF2026026043000068.tif62168
[0085] 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.
[0086] 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%.
[0087] <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)).
[0088] 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. TIFF2026026043000069.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.
[0089] 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 a24Examples 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.
[0090] 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 a8 It 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. 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 an integer of preferably 0 to 2, and more preferably 0 or 1.
[0091] 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'). TIFF2026026043000070.tif2956(in the formula, R a24 , L a7 has the same meaning as above.)
[0092] 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%.
[0093] <Structural unit (a4)> The structural unit represented by formula (a4) is shown below. TIFF2026026043000072.tif2753[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 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-.]
[0094] 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): TIFF2026026043000073.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. R 42 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.
[0095] 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. TIFF2026026043000074.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 42f represents a hydrogen atom or a fluorine atom.
[0096] 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 42fExamples 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 42f Examples 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 42fThe 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.
[0097] L 42f Examples of the perfluoroalkanediyl group in the formula (I) include a difluoromethylene group, a perfluoroethylene group, a perfluoroethylfluoromethylene group, a perfluoropropane-1,3-diyl group, a perfluoropropane-1,2-diyl group, a perfluoropropane-2,2-diyl group, a perfluorobutane-1,4-diyl group, a perfluorobutane-2,2-diyl group, a perfluorobutane-1,2-diyl group, a perfluoropentane-1,5-diyl group, a perfluoropentane-2,2-diyl group, a perfluoropentane-3 ,3-diyl group, perfluorohexane-1,6-diyl group, perfluorohexane-2,2-diyl group, perfluorohexane-3,3-diyl group, perfluoroheptane-1,7-diyl group, perfluoroheptane-2,2-diyl group, perfluoroheptane-3,4-diyl group, perfluoroheptane-4,4-diyl group, perfluorooctane-1,8-diyl group, perfluorooctane-2,2-diyl group, perfluorooctane-3,3-diyl group, and perfluorooctane-4,4-diyl group. L 42f Examples of the perfluorocycloalkanediyl group in the formula (I) include a perfluorocyclohexanediyl group, a perfluorocyclopentanediyl group, a perfluorocycloheptanediyl group, and a perfluoroadamantanediyl group.
[0098] L 41 is preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms, more preferably a single bond, a methylene group or an ethylene group, and even more preferably a single bond or a methylene group. L 42fis preferably a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluorocycloalkanediyl group having 3 to 12 carbon atoms, more preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and even more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.
[0099] 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. 41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF2026026043000075.tif55167The structural unit represented by formula (a4-2) is the structural unit shown below. TIFF2026026043000076.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.
[0100] 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 43fAs 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.
[0101] 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). TIFF2026026043000077.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 ]
[0102] L in the group represented by formula (L43f-1) 45f , L 46f and L 47fExamples 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.
[0103] 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 TIFF2026026043000078.tif47140
[0104] 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). TIFF2026026043000079.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 43fBrepresents 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 43fBThe 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.
[0105] 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). TIFF2026026043000080.tif15170
[0106] 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. TIFF2026026043000081.tif99167
[0107] 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. TIFF2026026043000082.tif111164
[0108] The structural unit (a4) also includes a structural unit represented by formula (a4-3). TIFF2026026043000083.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.
[0109] 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 44fis 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.
[0110] 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. TIFF2026026043000084.tif86170
[0111] The structural unit (a4) also includes a structural unit represented by formula (a4-A). TIFF2026026043000085.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 R44 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.]
[0112] 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 group or an ethyl group, and even more preferably a hydrogen atom or a methyl group.
[0113] L 44 Examples of the aliphatic hydrocarbon group in include chain hydrocarbon groups and monocyclic or polycyclic (including spiro rings, fused rings, bridged rings, etc.) alicyclic hydrocarbon groups, and may also be groups that combine two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and a chain hydrocarbon group). Examples of the chain hydrocarbon group include divalent to pentavalent chain hydrocarbon groups such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, and an alkanpentyl 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, 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 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. 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.
[0114] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following alicyclic hydrocarbon groups: The binding site can be any position. TIFF2026026043000086.tif45164 Examples include divalent to pentavalent alicyclic hydrocarbon groups such as a cycloalkanediyl group, a cycloalkanetriyl group, a cycloalkanetetrayl group, and a cycloalkanepentyl 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, and the like; Examples include cycloalkanediyl groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, decahydronaphthalenediyl group, bicyclo[3.3.0]octanediyl group, spirocyclohexane-1,2'-cyclopentane-diyl group, and spiroadamantane-2,3'-cyclopentane-diyl group; and polycyclic alicyclic hydrocarbon groups such as spiro rings having cycloalkanediyl groups bonded to norbornanediyl groups or adamantanediyl groups via spiro bonds. 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, and even more preferably 3 to 12 carbon atoms.
[0115] Examples of groups that combine two or more types include groups that combine an alicyclic hydrocarbon group and a chain hydrocarbon group. In the combination, two or more types of alicyclic hydrocarbon groups and chain hydrocarbon groups may be combined. In addition, when any of the groups is X 44 may be bound to Examples of groups combining an alicyclic hydrocarbon group and a chain hydrocarbon group include a group in which an alicyclic hydrocarbon group is bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), a group in which a chain hydrocarbon group is bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.), a group in which an alicyclic hydrocarbon group and a chain hydrocarbon group are bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.), a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are bonded to an alicyclic hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.), Examples of such a group include a group having a hydrocarbon group bonded thereto (for example, *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), a group having an alicyclic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group bonded to a chain hydrocarbon group (for example, *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), and a group having an alicyclic hydrocarbon group, a chain hydrocarbon group, and a chain hydrocarbon group bonded to an alicyclic hydrocarbon group (for example, *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.). * is X 44 represents the binding site with Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites.
[0116] L 44 -CH2- contained in the aliphatic hydrocarbon group having 1 to 28 carbon atoms may be replaced by -O-, -S-, -SO-, -SO2- or -CO-. L 44 When one -CH2- in the aliphatic hydrocarbon group having 1 to 28 carbon atoms is replaced with -O-, -S-, -SO-, -SO2- or -CO-, the number of carbon atoms before replacement is regarded as the number of carbon atoms in the aliphatic hydrocarbon group. Examples of groups in which -CH- in an aliphatic hydrocarbon group is replaced with -O-, -S-, -SO-, -SO-, or -CO- include a hydroxy group, a carboxy group, a thiol group, an alkoxy group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an oxy group, a carbonyl group, a thio group, a sulfonyl group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, a cycloalkoxy group, a cycloalkylalkoxy group, and groups in which two or more of these groups are combined. Examples of these substituted groups include the same groups exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced by -O-, -S-, -SO-, -CO- or -SO2- include the same groups as exemplified in this specification, within the upper limit of the number of carbon atoms permitted.
[0117] L 44 The aliphatic hydrocarbon group in may have one or more substituents, such as a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms (wherein -CH2- in the alkyl group or the alicyclic hydrocarbon group may be replaced by -O- or -CO-). Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of haloalkyl groups having 1 to 4 carbon atoms include fluorinated alkyl groups having 1 to 4 carbon atoms, chlorinated alkyl groups having 1 to 4 carbon atoms, brominated alkyl groups having 1 to 4 carbon atoms, and iodinated alkyl groups having 1 to 4 carbon atoms. Examples of haloalkyl groups include perfluoroalkyl groups having 1 to 4 carbon atoms (such as trifluoromethyl, pentafluoroethyl, heptafluoropropyl, and nonafluorobutyl), 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 3,3,4,4,4-pentafluorobutyl, chloromethyl, bromomethyl, and iodomethyl. The number of carbon atoms in the haloalkyl group is preferably 1 to 3, and more preferably 1 or 2. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. Examples of the alicyclic hydrocarbon group having 3 to 18 carbon atoms include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl, and polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16, more preferably 3 to 12, and even more preferably 3 to 10. Examples of aromatic hydrocarbon groups having 6 to 18 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 14, more preferably 6 to 12, and even more preferably 6 to 10. When -CH2- in an alkyl group is replaced with -O- or -CO-, the number of carbon atoms before the replacement is counted as the total number of carbon atoms in the alkyl group. Examples of the substituted group include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, and an alkoxycarbonyloxy group. These substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the carbon number. The number of carbon atoms in the alkoxy group is preferably 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 9, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 10, 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 alkylcarbonyloxy group is preferably 2 to 9, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Furthermore, examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O- or -CO- include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. L 44 The substituent that the aliphatic hydrocarbon group in the formula (I) may have is preferably a halogen atom, a haloalkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms (-CH2- contained in the alkyl group or the alicyclic hydrocarbon group may be replaced with -O- or -CO-), more preferably a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 3 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, or a methoxy group. L 44 is R 46When the fluorinated alkyl group does not form an alicyclic hydrocarbon group with the fluorinated alkyl group, the alicyclic hydrocarbon group is a chain hydrocarbon group of 1 to 12 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O- or -CO-), or a chain hydrocarbon group of 1 to 6 carbon atoms which may have a substituent and an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent. and a group formed by combining a hydrocarbon group with a hydroxyl group (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), and examples thereof include a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 12 carbon atoms which may have a substituent, or a group formed by combining a hydrocarbon group with a hydroxyl group with a hydroxyl group (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-). It is more preferably a group formed by combining a chain hydrocarbon group of 1 to 6 carbon atoms with an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), and examples thereof include a chain hydrocarbon group of 1 to 8 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group of 5 to 12 carbon atoms which may have a substituent, a chain hydrocarbon group of 1 to 6 carbon atoms and More preferably, it is a group formed by combining an alicyclic hydrocarbon group of 5 to 12 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), or a group formed by combining an alicyclic hydrocarbon group of 5 to 12 carbon atoms which may have a substituent, a chain hydrocarbon group of 1 to 6 carbon atoms, and an alicyclic hydrocarbon group of 5 to 12 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-).
[0118] R 45Examples of the fluorinated alkyl group having 1 to 8 carbon atoms in the formula (I) include a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a perfluoroethyl group, a 1,1,2,2-tetrafluoropropyl group, a 1,1,2,2,3,3-hexafluoropropyl group, a perfluoroethylmethyl group, a 1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 1,1,2,2-tetrafluorobutyl group, a 1,1,2,2,3,3-hexafluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluorobutyl group, a 1,1-bis(trifluoro)methyl group, a Examples of the fluorinated alkyl group include 2,2,2-trifluoroethyl, 2-(perfluoropropyl)ethyl, 1,1,2,2,3,3,4,4-octafluoropentyl, perfluoropentyl, 1,1,2,2,3,3,4,4,5,5-decafluoropentyl, 1,1-bis(trifluoromethyl)-2,2,3,3,3-pentafluoropropyl, perfluoropentyl, 2-(perfluorobutyl)ethyl, 1,1,2,2,3,3,4,4,5,5-decafluorohexyl, 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexyl, perfluoropentylmethyl, perfluorohexyl, perfluoroheptyl, and perfluorooctyl. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 6, more preferably 1 to 5, even more preferably 1 to 4, and even more preferably 1 to 3. R 46 The fluorinated alkyl group having 1 to 6 carbon atoms in R is as large as possible within the upper limit of the carbon number. 45 The same fluorinated alkyl groups having 1 to 6 carbon atoms as those given as examples of the fluorinated alkyl groups in the above can also be used. R 45 is R 46 When is a fluorinated alkyl group having 1 to 6 carbon atoms, it is preferably a fluorinated alkyl group having 1 to 6 carbon atoms, more preferably a fluorinated alkyl group having 1 to 3 carbon atoms, still more preferably a trifluoromethyl group, a perfluoroethyl group or a perfluoropropyl group, and even more preferably a trifluoromethyl group. R45 is R 46 When is a hydrogen atom, it is preferably a fluorinated alkyl group having 1 to 6 carbon atoms, more preferably a fluorinated alkyl group having 1 to 5 carbon atoms, and even more preferably a fluorinated alkyl group having 3 to 5 carbon atoms. R 46 L 44 When R is bonded to form an alicyclic hydrocarbon group having 3 to 12 carbon atoms, 46 L 44 Examples of groups formed by bonding with include groups represented by the following formulae: In the following formulae, * and ** represent bonding sites, and one of the two ** represents a bonding site with a hydroxy group and the other represents a bonding site with R 45 represents the binding site with L 44A L 44 R is a part of the hydrocarbon group and represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. 46 L 44 The alicyclic hydrocarbon group formed by bonding with the above preferably has 3 to 10 carbon atoms, more preferably 3 to 8 carbon atoms, and even more preferably 3 to 6 carbon atoms. TIFF2026026043000087.tif22138R 46 is preferably a hydrogen atom or a fluorinated alkyl group having 1 to 3 carbon atoms. mi is preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1.
[0119] Examples of the structural unit (a4-A) include the following structural units. In the following structural units, R 44 and structural units in which the methyl group corresponding to R is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or an alkyl group other than a methyl group. 44 Specific examples of the structural unit (a4-A) include structural units in which the hydrogen atom corresponding to the following is replaced with a halogen atom, a haloalkyl group, or an alkyl group. TIFF2026026043000088.tif182158
[0120] When the resin (A) contains the structural unit (a4), the content thereof is preferably 1 to 20 mol %, more preferably 2 to 15 mol %, and even more preferably 3 to 10 mol %, based on all structural units in the resin (A).
[0121] <Structural unit (a5)> The non-leaving hydrocarbon group contained in the structural unit (a5) may be a group containing a linear, branched, or cyclic hydrocarbon group, and among these, the structural unit (a5) is preferably a group containing an alicyclic hydrocarbon group. Examples of the structural unit (a5) include a structural unit represented by formula (a5-1). TIFF2026026043000089.tif3971[In formula (a5-1), R 51 represents a hydrogen atom or a methyl group. R 52 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group may be substituted with an aliphatic hydrocarbon group having 1 to 8 carbon atoms. L 55 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.]
[0122] R 52 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of polycyclic alicyclic hydrocarbon groups include adamantyl and norbornyl. Examples of the aliphatic hydrocarbon group having 1 to 8 carbon atoms include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl. Examples of the alicyclic hydrocarbon group having a substituent include a 3-methyladamantyl group. R 52is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, and more preferably an adamantyl group, a norbornyl group, or a cyclohexyl group. L 55 The divalent saturated hydrocarbon group in the formula (I) includes a divalent saturated chain hydrocarbon group and a divalent saturated alicyclic hydrocarbon group, and is preferably a divalent saturated chain hydrocarbon group. Examples of the divalent chain saturated hydrocarbon group include a methylene group, an ethylene group, and an alkanediyl group such as a propanediyl group, a butanediyl group, and a pentanediyl group. The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic saturated hydrocarbon group include cycloalkanediyl groups such as cyclopentanediyl and cyclohexanediyl. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include adamantanediyl and norbornanediyl.
[0123] L 55 Examples of the divalent saturated hydrocarbon group represented by formula (L1-1) in which one -CH2- is replaced with -O- or -CO- include groups represented by formula (L1-1) to formula (L1-4). In the following formulae, * and ** each represent a bonding site, and * represents a bonding site to an oxygen atom. TIFF2026026043000090.tif18165[In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents L x1 represents the binding site with ). L x1 represents a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. L x2 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. However, L x1 and L x2 The total number of carbon atoms is 16 or less. In formula (L1-2), L x3 represents a divalent aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms. L x4represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. However, L x3 and L x4 The total number of carbon atoms is 17 or less. In formula (L1-3), L x5 represents a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. L x6 and L x7 each independently represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 14 carbon atoms. However, L x5 , L x6 and L x7 The total number of carbon atoms is 15 or less. In formula (L1-4), L x8 and L x9 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms. W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, L x8 , L x9 and W x1 The total number of carbon atoms is 15 or less.
[0124] L x1 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x2 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond. L x3 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x6is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x7 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x8 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. L x9 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. W x1 is preferably a divalent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, more preferably a cyclohexanediyl group or an adamantanediyl group.
[0125] Examples of the group represented by formula (L1-1) include the divalent groups shown below. TIFF2026026043000091.tif36146 Examples of the group represented by formula (L1-2) include the divalent groups shown below. TIFF2026026043000092.tif23130 Examples of the group represented by formula (L1-3) include the divalent groups shown below. TIFF2026026043000093.tif16147 Examples of the group represented by formula (L1-4) include the divalent groups shown below. TIFF2026026043000094.tif13167L 55 is preferably a single bond or a group represented by formula (L1-1).
[0126] The structural unit (a5-1) includes the structural units shown below and R in the structural unit (a5-1) in the structural units shown below. 51 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. When the resin (A) contains the structural unit (a5), the content thereof is preferably 1 to 30 mol %, more preferably 2 to 20 mol %, and even more preferably 3 to 15 mol %, based on all structural units in the resin (A).
[0127] <Structural unit (a6)> The structural unit (a6) is a structural unit having an -SO2- group, and preferably has an -SO2- group in a side chain. The structural unit having an -SO2- group may have a linear structure having an -SO2- group, a branched structure having an -SO2- group, or a cyclic structure (monocyclic or polycyclic structure) having an -SO2- group. A structural unit having a cyclic structure having an -SO2- group is preferred, and a structural unit having a cyclic structure containing an -SO2-O- group (sultone ring) is more preferred.
[0128] The sultone ring may be a ring having the following formula (T 1 -1), formula (T 1 -2), formula (T 1 -3) and the formula (T 1 The bonding site can be any position. The sultone ring may be monocyclic, but is preferably polycyclic. A polycyclic sultone ring refers to a bridged ring containing -SO2-O- as an atomic group constituting the ring, and is represented by the formula (T 1 -1) and the formula (T 1 The sultone ring is represented by the formula (T 1 As in the ring represented by formula (2), the atomic group constituting the ring may further contain a heteroatom in addition to —SO—O—. Examples of the heteroatom include an oxygen atom, a sulfur atom, and a nitrogen atom, and an oxygen atom is preferred. TIFF2026026043000096.tif3077
[0129] The sultone ring may have a substituent, and examples of the substituent include an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, and an alkylcarbonyl group having 2 to 4 carbon atoms.
[0130] Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, and a decyl group, and preferably an alkyl group having 1 to 6 carbon atoms, and more preferably a methyl group. Examples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group, and preferably a trifluoromethyl group. Examples of the alkyl group having a hydroxy group include a hydroxymethyl group and a 2-hydroxyethyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a p-methylphenyl group, a p-tert-butylphenyl group, a p-adamantylphenyl group, a tolyl group, a xylyl group, a cumyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group. Aralkyl groups include benzyl, phenethyl, phenylpropyl, naphthylmethyl, and naphthylethyl groups. Examples of the alkoxycarbonyl group include groups in which an alkoxy group, such as a methoxycarbonyl group or an ethoxycarbonyl group, is bonded to a carbonyl group, and preferably includes an alkoxycarbonyl group having 6 or less carbon atoms, more preferably a methoxycarbonyl group. Alkylcarbonyl groups include acetyl, propionyl and butyryl groups. From the viewpoint of ease of production of the monomer from which the structural unit (a6) is derived, a sultone ring having no substituent is preferred.
[0131] The sultone ring is preferably a ring represented by the following formula (T1'). TIFF2026026043000097.tif2666[In formula (T1'), X 11 represents an oxygen atom, a sulfur atom or a methylene group. R 41 represents an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, or an alkylcarbonyl group having 2 to 4 carbon atoms. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41 may be the same or different. The binding site is at any position.] X 11 is preferably an oxygen atom or a methylene group, more preferably a methylene group. R 41 Examples of the substituent include the same as the substituent on the sultone ring, and an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group is preferred. ma is preferably 0 or 1, and more preferably 0.
[0132] Examples of the ring represented by formula (T1') include the following rings: The bonding site may be any position, and the bonding site is preferably the 1st or 3rd position. TIFF2026026043000098.tif45147
[0133] The structural unit having an -SO2- group preferably further has a group derived from a polymerizable group, such as a vinyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, an acryloylthio group, or a methacryloylthio group. Among these, the monomer from which the structural unit (a6) is derived is preferably a monomer having an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer.
[0134] The structural unit (a6) is preferably a structural unit represented by the formula (a6-0). TIFF2026026043000099.tif4177[In formula (a6-0), R x represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom. A xx is an oxygen atom, -N(R c )- or a sulfur atom. A x represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group is not -O-, -CO- or -N(R d )- may be replaced. X 11 represents an oxygen atom, a sulfur atom or a methylene group. R 41 represents the same meaning as above. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41 may be the same or different. R c and R d each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
[0135] R x , R c and R d is R in formula (a1-0) a01 The same examples as those given above are included. R x is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. A x Examples of the divalent saturated hydrocarbon group include a linear alkanediyl group, a branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and may be a combination of two or more of these groups. Specifically, methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group linear alkanediyl groups such as a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, a heptadecane-1,17-diyl group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group; branched alkanediyl groups such as butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl; monocyclic divalent alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; Examples include polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group. A x The bonding position of to the sultone ring can be any position, but the 1-position is preferred.
[0136] Examples of the structural unit (a6-0) include the following structural units. TIFF2026026043000100.tif93150
[0137] Of these, structural units represented by formula (a6-1), formula (a6-2), formula (a6-6), formula (a6-7), formula (a6-8), and formula (a6-12) are preferred, and structural units represented by formula (a6-1), formula (a6-2), formula (a6-7), and formula (a6-8) are more preferred. When the resin (A) contains the structural unit (a6), the content thereof is preferably 1 to 50 mol %, more preferably 2 to 40 mol %, and even more preferably 3 to 30 mol %, based on all structural units in the resin (A).
[0138] <Structural unit (a7)> The resin (A) may further contain a structural unit that decomposes upon exposure to generate an acid (hereinafter, sometimes referred to as "structural unit (a7)"). Specific examples of the structural unit (a7) include the structural units described in JP 2016-79235 A, and the structural unit (a7) is preferably a structural unit having a sulfonate anion or a carboxylate anion and an organic cation in the side chain, or a structural unit having a sulfonium cation and an organic anion in the side chain. The structural unit having a sulfonate anion or a carboxylate anion and an organic cation in the side chain is preferably a structural unit represented by formula (a7-A). TIFF2026026043000101.tif26124[In formula (a7-A), R a7 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X a71 is a single bond, or -O-, -CO-, -S-, -SO-, -SO2-, -NR a71represents -, a phenylene group which may have a substituent, or a group in which these are combined. R a71 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L a71 and L a72 each independently represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, SO- or -SO2-. X a72 represents ***-CO-O-, ***-O-CO-, ***-O-CO-O-, ***-O-, and *** represents L a71 represents the binding site with na7 represents an integer of 0 to 2. When na7 is 2, the groups in the parentheses may be the same or different. RA - represents a sulfonate anion or a carboxylate anion. ZA + represents an organic cation.
[0139] R a7 is R in formula (a1-0) a01 Among them, R a7 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, further preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a71 Examples of the alkyl group having 1 to 6 carbon atoms in the formula include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. X a71 represents a single bond, -O-, -CO-, -NR a71 -, a phenylene group which may have a substituent, or a group in which these are combined is preferred, and a single bond, *-O-**, *-CO-O-**, *-O-CO-O-**, *-CO-NR a71 -**, *-NR a71-CO-O-**, *-O-CO-NR a71 It is more preferable that it is -** or *-Ax-Ph-Ay-**. In the above groups, * and ** represent binding sites, * represents R a7 represents a bonding site with the carbon atom to which Ax and Ay are bonded. Ax and Ay each independently represent one or more bonding types selected from the group consisting of a single bond, an ether bond, a thioether bond, an amide bond, an ester bond, and a carbonate ester bond. Ph represents a phenylene group which may have a substituent. X a71 is a group represented by *-Ax-Ph-Ay-**, it is preferably a linking group represented by the following formula (X10). TIFF2026026043000102.tif3351[In formula (X10), Ax and Ay have the same meanings as above. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4, and when mx is an integer of 2 or greater, multiple Rx's may be the same or different. When either Ax or Ay is a single bond, the other is preferably one or more bonds selected from the group consisting of an ether bond, a thioether bond, an ester bond, a carbonate ester bond, and an amide bond. When either Ax or Ay is an amide bond, -CO-NR a71 A bond represented by - is preferred. The bonding position of Ay in the phenylene group is preferably the m-position or p-position relative to the bonding position of Ax, and more preferably the p-position. Among these, Rx is preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, or an ethyl group. mx is preferably 0, 1 or 2. X a71 Examples of the group include a single bond and a group represented by the following formula (X 10 -1)~Formula(X 10 X-10)20 is -O- or -NR a71 - represents. TIFF2026026043000103.tif44162 expression (X 10 -1)~Formula(X 10 Specific examples of the group represented by -10) include the following groups: TIFF2026026043000104.tif79161Among them, X a71 is a single bond and a group of formula (X 10 -1'), expression (X 10 -3')~expression(X 10 -10'), and is preferably a single bond or a group represented by the formula (X 10 -1'), expression (X 10 -4'), expression (X 10 -5'), expression (X 10 -6') and formula (X 10 -10'), and more preferably a single bond, a group represented by the formula (X 10 -1'), a group represented by the formula (X 10 -5') or a group represented by the formula (X 10 -6') is more preferred.
[0140] L a71 The hydrocarbon group may be a group formed by removing one hydrogen atom from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups to form X. a71 and X a72 In addition, L a72 The hydrocarbon group may be a group formed by removing one hydrogen atom from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups to form X. a72 and R.A. - Examples of such groups include groups that bond to the following: L a71 and L a72Examples of the chain hydrocarbon group include groups in which one hydrogen atom has 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, decanyl, undecanyl, dodecanyl, tridecanyl, tetradecanyl, pentadecanyl, and heptadecanyl groups. Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. The chain hydrocarbon group preferably has 1 to 20 carbon atoms, more preferably 1 to 18 carbon atoms, and even more preferably 1 to 10 carbon atoms. L a71 and L a72 Examples of the alicyclic hydrocarbon group include groups in which one hydrogen atom has 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. L a71 and L a72Examples of the polycyclic cycloalkyl group include a cycloalkyl group having a bridged structure, a cycloalkyl group in which two or more rings are fused, or a cycloalkyl group in which two rings are bonded via a spiro bond. Examples of the cycloalkyl group having a bridged structure include a norbornyl group and an adamantyl group. Examples of the cycloalkyl group in which two or more rings are fused include a bicyclo[4.4.0]decanyl group and a steroid group (steroid skeleton). Examples of the cycloalkyl group in which two rings are bonded via a spiro bond include a spirocyclic cycloalkyl group in which one cycloalkyl group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group 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, examples of the alicyclic hydrocarbon group include alicyclic hydrocarbon groups represented by the following formula: TIFF2026026043000105.tif28158When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and even more preferably 3 to 8 carbon atoms.When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the alicyclic hydrocarbon group preferably has 6 to 18 carbon atoms, and more preferably 7 to 12 carbon atoms. L a71 and L a72 Examples of the aromatic hydrocarbon group include groups in which one hydrogen atom has been removed from an aryl group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a fluorenyl group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 5 to 14, more preferably 6 to 14, and even more preferably 6 to 10. L a71 and L a72 When -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 a71 and L a72Among these hydrocarbon groups, examples of groups in which -CH- in a chain hydrocarbon group is replaced with -O-, -CO-, -S-, -SO- or -SO- include a hydroxy group, a carboxy group, a thiol group, a carbonyl group, an oxy group, a thio group, a sulfonyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, and an alkanediylcarbonyloxy group. Examples of 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. L a71 and L a72 Among these hydrocarbon groups, examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2- include groups containing structures such as cyclic ether, cyclic ketone, cyclic ester (lactone), cyclic thioether, cyclic acetal, and cyclic sulfonate ester (sultone). These substituted groups include the same groups exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. L a71 and L a72 Among these hydrocarbon groups, -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-, and examples of the group in which -CH2- is replaced by -O- or -S- include groups derived from a furan ring or a thiophene ring, respectively. L a71 and L a72 Examples of the group combining two or more groups selected from the chain hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group include a group combining the chain hydrocarbon group with the alicyclic hydrocarbon group, a group combining the chain hydrocarbon group with the aromatic hydrocarbon group, a group combining the alicyclic hydrocarbon group with the aromatic hydrocarbon group, and a group combining the chain hydrocarbon group with the alicyclic hydrocarbon group and the aromatic hydrocarbon group, and examples of the above-mentioned combined groups include the group combining the alicyclic hydrocarbon group with the aromatic hydrocarbon group. The group combining the alicyclic hydrocarbon group with the aromatic hydrocarbon group may be a fused ring. L a71 and L a72Examples 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 a71 and L a72 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 substantially a substituent that the alicyclic hydrocarbon group or the aromatic hydrocarbon group has. a71 and L a72 The -CH2- of the chain hydrocarbon group contained in the hydrocarbon group is replaced with -O-, -CO-, -S- or -SO2-, thereby forming L a71 and L a72 The hydrocarbon group may substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, a thiol group, an alkylthio group, or an alkylsulfonyl group. na7 is preferably 0 or 1. ZA in formula (a7-A) + The cations are the same as those in the salt represented by formula (B1).
[0141] In formula (a7-A), L a71 and L a72 When the hydrocarbon group is a saturated hydrocarbon group, in the formula (a7-B) described later, A b7 The divalent linking group may contain the same groups as those exemplified above. Examples of the structural unit represented by formula (a7-A) include a structural unit represented by formula (a7-A1). TIFF2026026043000106.tif31138[In formula (a7-A1), R a7 , X a71 , L a71 , X a72 , na7, RA - and ZA + has the same meaning as above. z7 represents an integer of 0 to 6. Q a7 , Qb7 , R z71 and R z72 each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms; when z7 is 2 or greater, a plurality of R z71 and R z72 may be the same or different from each other. Q a7 , Q b7 , R z71 and R z72 In the formula, the perfluoroalkyl group having 1 to 6 carbon atoms or the alkyl group having 1 to 6 carbon atoms is R a7 Examples of the groups include the same groups as those exemplified in the above.
[0142] Examples of the structural unit represented by formula (a7-A) include the following structural units, R a7 Examples of such a structural unit include a structural unit in which the group corresponding to the methyl group in the formula (1) is replaced with a hydrogen atom, a halogen atom (e.g., a fluorine atom), or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (e.g., a trifluoromethyl group), and the structural units described in WO 2012 / 050015. + represents an organic cation. TIFF2026026043000107.tif244162
[0143] TIFF2026026043000108.tif140161
[0144] The structural unit having a sulfonio group and an organic anion on the side chain is preferably a structural unit represented by formula (a7-B). TIFF2026026043000109.tif28105[In formula (a7-B), R a7 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. A b7 represents a single bond or a divalent linking group. R b71 represents a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. Rb72 and R b73 each independently represents a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and R b72 and R b73 may be bonded to each other to form a ring together with the sulfur atom to which they are attached. A - represents an organic anion. R a7 Examples of the halogen atom and the alkyl group which may have a halogen atom include the same halogen atom and the alkyl group which may have a halogen atom as those of formula (a7-A). R b71 Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula include a phenylene group and a naphthylene group. R b72 and R b73 Examples of the hydrocarbon group represented by the formula (I) include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. Examples of the alkyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and group formed by combining these groups include the same as those described above. A b7 Examples of the divalent linking group represented by the formula (I) include divalent saturated hydrocarbon groups having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O-, -S-, or -CO-. Examples of the divalent saturated hydrocarbon group include divalent chain saturated hydrocarbon groups such as linear or branched alkanediyl groups, and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups, and combinations thereof are also possible. Specific examples thereof include linear 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; and linear alkanediyl groups such as butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4 divalent monocyclic alicyclic saturated hydrocarbon groups such as branched alkanediyl groups, e.g., cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, and the like; and divalent polycyclic alicyclic saturated hydrocarbon groups such as polycyclic cycloalkanediyl groups, e.g., norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, and the like. Examples of saturated hydrocarbon groups in which -CH2- is replaced with -O-, -S-, or -CO- include the divalent groups shown below. However, the number of carbon atoms before the -CH2- in the saturated hydrocarbon group is replaced with -O-, -S-, or -CO- is 17 or less. In the following formula, * and ** represent bonding sites, and * represents R b71 represents the binding site with TIFF2026026043000110.tif123161[where, X 3 represents a divalent saturated hydrocarbon group having 1 to 16 carbon atoms. X 4 represents a divalent saturated hydrocarbon group having 1 to 15 carbon atoms. X 5 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms. X 6 represents a divalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 7 represents a trivalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 8represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.
[0145] The structural unit containing a cation in formula (a7-B) includes the structural unit represented by the following formula and R a7 Examples of structural units include those in which a group corresponding to the methyl group in the above formula (I) is replaced with a hydrogen atom, a halogen atom (for example, a fluorine atom), or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (for example, a trifluoromethyl group). TIFF2026026043000111.tif72163
[0146] A - Examples of the organic anion represented by the formula (A) include a sulfonate anion, a sulfonylimide anion, a sulfonylmethide anion, and a carboxylate anion. - The organic anion represented by the formula (I) is preferably a sulfonate anion, and the sulfonate anion is more preferably the same as the anions exemplified for the acid generator (B). Examples of the sulfonylimide anion, sulfonylmethide anion, and carboxylate anion include the same anions exemplified for the acid generator (B).
[0147] Examples of the structural unit represented by formula (a7-B) include structural units represented by the following formulas: TIFF2026026043000112.tif95158
[0148] When the structural unit (a7) is contained in the resin (A), the content of the structural unit (a7) is preferably 1 to 20 mol %, more preferably 2 to 15 mol %, and even more preferably 3 to 10 mol %, based on the total structural units of the resin (A).
[0149] The resin (A) is preferably a resin composed of a plurality of structural units (IP), i.e., a copolymer of a plurality of compounds (I); a resin composed of the structural unit (IP) and the structural unit (a1), i.e., a copolymer of the compound (I) and the monomer (a1); a resin composed of the structural unit (IP) and the structural unit (s), i.e., a copolymer of the compound (I) and the monomer (s); a resin composed of the structural unit (IP), the structural unit (a1) and the structural unit (s), i.e., a copolymer of the compound (I), the monomer (a1) and the monomer (s). The structural unit (a1) is preferably at least one selected from the group consisting of the structural unit (a1-0), the structural unit (a1-1), the structural unit (a1-2), the structural unit (a1-4), the structural unit represented by formula (a1-5), and the structural unit represented by formula (a1-6), and more preferably at least one selected from the group consisting of the structural unit (a1-0), the structural unit (a1-2), and the structural unit represented by formula (a1-6). The structural unit (s) is preferably at least one selected from the group consisting of the structural unit (a2), the structural unit (a3), and the structural unit (a7). The structural unit (a2) is preferably a structural unit represented by formula (a2-C). The structural unit (a3) is preferably at least one selected from the group consisting of the structural unit represented by formula (a3-1), the structural unit represented by formula (a3-2), and the structural unit represented by formula (a3-4). The structural unit (a7) is preferably a structural unit represented by formula (a7-A).
[0150] The structural units constituting the resin (A) may be used singly or in combination of two or more, and can be produced by a known polymerization method (e.g., radical polymerization) using monomers that lead to these structural units. The content of each structural unit in the resin (A) can be adjusted by the amount of monomer used in the polymerization. The weight-average molecular weight of resin (A) is preferably 2,000 or more (more preferably 2,500 or more, even more preferably 3,000 or more) and 50,000 or less (more preferably 30,000 or less, even more preferably 15,000 or less), but it may contain oligomers with lower weight-average molecular weights. In this specification, the weight-average molecular weight is a value determined by gel permeation chromatography under the conditions described in the Examples.
[0151] <Resins other than Resin (A)> The resist composition of the present invention may contain a resin other than the resin (A). Examples of resins other than resin (A) include a resin (hereinafter sometimes referred to as "resin (AX)") that contains the same structural units as resin (A) except that it does not contain structural unit (a1), and a resin that contains structural unit (a4) and / or structural unit (a5) (however, it does not contain structural unit (IP) and structural unit (a1); hereinafter sometimes referred to as "resin (X)"). Examples of resin (AX) include resins containing the structural unit (a2), preferably resins containing the structural unit (a2-A), and more preferably resins containing the structural unit (a2-A) and the structural unit (a2-B). In resin (AX), the content of the structural unit (a2-A) is preferably 5 mol% or more, more preferably 10 mol% or more, and even more preferably 15 mol% or more, based on the total of all structural units in resin (AX). It is also preferably 80 mol% or less, and even more preferably 70 mol% or less. In resin (AX), the content of the structural unit (a2-B) is preferably 5 mol% or more, more preferably 10 mol% or more, and even more preferably 15 mol% or more, based on the total of all structural units in resin (AX). ... It is preferred that the content of the structural unit (a2-B) in resin (AX) be greater than the content of the structural unit (a2-A). Examples of structural units that may be further contained in the resin (X) include the structural unit (a2), the structural unit (a3), and structural units derived from other known monomers. Among these, the resin (X) is preferably a resin consisting only of the structural unit (a4) and / or the structural unit (a5), and more preferably a resin consisting only of the structural unit (a4). When resin (X) contains structural unit (a4), the content of structural unit (a4) in resin (X) is, based on the total of all structural units in resin (X), 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more. Also, it may be 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, even more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, it may be 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, even more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. When resin (X) contains structural unit (a5), the content of structural unit (a5) in resin (X) is, based on the total of all structural units in resin (X), 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more. Further, it may be 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, even more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specific examples include 20 to 100 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, even more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. Furthermore, when the resin (X) contains the structural unit (a4) and the structural unit (a5), the total content of the structural unit (a4) and the structural unit (a5) relative to the total of all structural units in the resin (X) may be 40 mol% or more, preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more. Specific examples include 100 mol% or less. Specific examples include 40 to 100 mol%, preferably 60 to 100 mol%, more preferably 70 to 100 mol%, and even more preferably 80 to 100 mol%. In particular, the resin (X) is preferably a resin consisting only of the structural unit (a4) and / or the structural unit (a5). In this case, the ratio of the structural unit (a4):the structural unit (a5) is 0:100 to 100:0, preferably 10:90 to 90:10, and more preferably 30:70 to 70:30 or 40:60 to 60:40. The structural units constituting resins (AX) and (X) may be used singly or in combination of two or more, and can be produced by known polymerization methods (e.g., radical polymerization) using monomers that derive these structural units. The content of each structural unit in resins (AX) and (X) can be adjusted by the amount of monomer used in polymerization. The weight-average molecular weight of resin (AX) and resin (X) is preferably 6,000 or more (more preferably 7,000 or more) and 80,000 or less (more preferably 60,000 or less), but they may contain oligomers with a lower weight-average molecular weight. The weight-average molecular weight of resin (AX) and resin (X) can be measured by the same method as for resin (A).
[0152] When the resist composition of the present invention contains resin (X), the content thereof is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, even more preferably 1 to 40 parts by mass, still more preferably 1 to 30 parts by mass, and particularly preferably 1 to 8 parts by mass, relative to 100 parts by mass of resin (A).
[0153] The total content of resin (A) in the resist composition is preferably 60% to 99% by mass, and more preferably 65% to 99% by mass, based on the solid content of the resist composition. Furthermore, the content of each resin (A) is preferably 60% to 99% by mass, and more preferably 65% to 99% by mass, based on the solid content of the resist composition. When resins other than resin (A) are contained, the content of resins other than resin (A) is preferably 30% to 80% by mass, and the content of resin (AX) is preferably 30% to 70% by mass. The total content of resin (A) and resins other than resin (A) is preferably 70% to 99% by mass, and even more preferably 80% to 99% by mass, and even more preferably 90% to 99% by mass, based on the solid content of the resist composition. The solid content of the resist composition and the resin content relative to the solid content can be measured using known analytical methods such as liquid chromatography or gas chromatography.
[0154] <Acid generator (B)> The acid generator (B) may be either a nonionic or ionic acid generator. Examples of nonionic acid generators include sulfonate esters (e.g., 2-nitrobenzyl esters, aromatic sulfonates, oximesulfonates, N-sulfonyloxyimides, sulfonyloxyketones, and diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfones, ketosulfones, and sulfonyldiazomethanes). Typical examples of ionic acid generators include onium salts containing onium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts, and 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 a structural unit that constitutes the resin contained in the resist composition, such as the structural unit (a7).
[0155] 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. The acid generator (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 becomes an acid labile group, and the acid labile group preferably contains group (1) or group (2) exemplified in this specification. When the resist composition of the present invention contains a compound that has an acid labile group, it does not necessarily need to contain a resin that contains a structural unit that has an acid labile group.
[0156] 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)"). TIFF2026026043000113.tif1392 [In formula (B1), all symbols have the same meanings as above.] 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. TIFF2026026043000114.tif26167When 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. Examples of aryl groups include phenyl, naphthyl, anthryl, biphenyl, and fluorenyl groups. More specifically, examples of aromatic hydrocarbon groups include those represented by the following formulas: TIFF2026026043000115.tif1185 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, even more preferably 5 to 14, even more preferably 5 to 10, and even more preferably 6 to 10. Examples of groups combining two or more of the chain hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group include groups combining the chain hydrocarbon group and the alicyclic hydrocarbon group, groups combining the chain hydrocarbon group and the aromatic hydrocarbon group, groups combining the alicyclic hydrocarbon group and the aromatic hydrocarbon group, and groups combining the chain hydrocarbon group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group. The group combining the alicyclic hydrocarbon group and the 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 the hydrocarbon groups mentioned above, examples of groups in which -CH2- in a 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 formed by 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, a nitro group, etc. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. L b1 and L b2 When 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 substantially 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-). 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 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. The anion of the salt represented by formula (B1) is preferably an anion represented by the following formula (B1-A1) (hereinafter, sometimes referred to as "anion (B1-A1)") or an anion represented by formula (B1-A2) (hereinafter, sometimes referred to as "anion (B1-A2)"). TIFF2026026043000116.tif30126[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 Q b2At 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—.
[0157] 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-. TIFF2026026043000117.tif1581[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 TIFF2026026043000118.tif37163 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 binding 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. TIFF2026026043000119.tif85161
[0158] 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). TIFF2026026043000120.tif216161
[0159] TIFF2026026043000121.tif249151
[0160] TIFF2026026043000122.tif254157
[0161] 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.
[0162] 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. TIFF2026026043000123.tif182157
[0163] TIFF2026026043000124.tif252164
[0164] TIFF2026026043000125.tif90165
[0165] The anion represented by formula (B1-A2) is represented by the following formula: TIFF2026026043000126.tif23100[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.
[0166] In formula (B1-A2), L b2 Examples of hydrocarbon groups and Y b1Examples of the cyclic hydrocarbon group include, within the upper limit of the carbon number, L in formula (B1). b2 Examples of hydrocarbon groups 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.
[0167] 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 TIFF2026026043000127.tif28106 [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.
[0168] 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.
[0169] 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-26) are more preferred. The following anions are also preferred in the case of some R b1 is omitted, and may contain substituents not shown. TIFF2026026043000128.tif173159
[0170] Examples of the acid generator (B2) include salts represented by the following formula: TIFF2026026043000129.tif1192 [In formula (B2), all symbols have the same meanings as 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'). TIFF2026026043000130.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 preferably has 3 to 12 carbon atoms, more 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.
[0171] 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. TIFF2026026043000131.tif174165
[0172] In another embodiment of the acid generator (B), a salt in which the 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: TIFF2026026043000132.tif41155
[0173] 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). TIFF2026026043000133.tif84159 [In formula (b2-1) to formula (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 and may be bonded to each other to form a ring containing a sulfur atom together with the benzene ring to which they are attached, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. 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. 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. o21, p22, q23, r24, t25 and s26 each independently represent an integer of 0 to 4. When u3, u4 and u5 each represent 2 or more, the groups in the parentheses are the same or different. When o21, p22, q23, r24, t25 and s26 are each 2 or more, multiple R b21 ~R b26 are the same or different.]
[0174] 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: TIFF2026026043000134.tif11157 In particular, R b9 ~R b12The 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. TIFF2026026043000135.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 b12The 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 b29 Examples 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).
[0175] 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. TIFF2026026043000136.tif96163
[0176] TIFF2026026043000137.tif126162Examples of the cation (b2-2) include the following cations. TIFF2026026043000138.tif18150Examples of the cation (b2-3) include the following cations. TIFF2026026043000139.tif26140Examples of the cation (b2-4) include the following cations. TIFF2026026043000140.tif129168 Examples of the cation (b2-5) include the following cations. TIFF2026026043000141.tif101165
[0177] 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).
[0178] 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. TIFF2026026043000142.tif176161
[0179] TIFF2026026043000143.tif254161
[0180] TIFF2026026043000144.tif254157
[0181] TIFF2026026043000145.tif253161
[0182] TIFF2026026043000146.tif253162
[0183] TIFF2026026043000147.tif250150
[0184] TIFF2026026043000148.tif187161
[0185] When the resist composition of the present invention contains an acid generator (B), the content of the acid generator (B) is, relative to the solid content of the resist composition, typically 1% by mass to 90% by mass, preferably 3% by mass to 45% by mass, more preferably 5% by mass to 40% by mass, and even more preferably 10% by mass to 35% by mass. When the resist composition of the present invention contains resin (A), the content of acid generator (B) is, relative to 100 parts by mass of resin (A), for example, 1 part by mass to 90 parts by mass, preferably 3 parts by mass to 45 parts by mass, more preferably 5 parts by mass to 40 parts by mass, and even more preferably 10 parts by mass to 35 parts by mass.
[0186] <Solvent (E)> The content of the solvent (E) in the resist composition is usually from 90 to 99.9% by mass, preferably from 92 to 99% by mass, and more preferably from 94 to 99% by mass. The content of the solvent (E) can be measured by known analytical means such as liquid chromatography or gas chromatography. Examples of the solvent (E) include glycol ether esters such as ethyl cellosolve acetate, methyl cellosolve acetate, and propylene glycol monomethyl ether acetate; glycol ethers such as propylene glycol monomethyl ether; esters such as ethyl lactate, butyl acetate, amyl acetate, and ethyl pyruvate; ketones such as acetone, methyl isobutyl ketone, 2-heptanone, and cyclohexanone; cyclic esters such as γ-butyrolactone; etc. One type of solvent (E) may be used alone, or two or more types may be used.
[0187] <Quencher (C)> Examples of the quencher (C) include a basic nitrogen-containing organic compound or a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator (acid generator (B)). When the resist composition contains the quencher (C), the content of the quencher (C) is preferably about 0.01 to 15 mass%, more preferably about 0.01 to 10 mass%, even more preferably about 0.1 to 8 mass%, and even more preferably about 0.1 to 7 mass%, based on the solids content of the resist composition. The basic nitrogen-containing organic compound includes amines and ammonium salts. The amines include aliphatic amines and aromatic amines. The aliphatic amines include primary amines, secondary amines, and tertiary amines. Amines include 1-naphthylamine, 2-naphthylamine, aniline, diisopropylaniline, 2-, 3- or 4-methylaniline, 4-nitroaniline, N-methylaniline, N,N-dimethylaniline, diphenylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, triethylamine, trimethylamine, tripropylamine, tributylamine, Amine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, methyldibutylamine, methyldipentylamine, methyldihexylamine, methyldicyclohexylamine, methyldiheptylamine, methyldioctylamine, methyldinonylamine, methyldidecylamine, ethyldibutylamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine, ethyldioctylamine, ethyldinonylamine, ethyldidecylamine amine, dicyclohexylmethylamine, tris[2-(2-methoxyethoxy)ethyl]amine, triisopropanolamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4'-diamino-1,2-diphenylethane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 4,4'-diamino-3,3'-diethyldiphenylmethane, 2,2'-methylenebisaniline, imidazole, 4-methylimidazole, pyridine, 4-methylpyridine, 1,2-di(2-pyridyl)ethane Examples of the amines include 1,2-di(4-pyridyl)ethane, 1,2-di(2-pyridyl)ethene, 1,2-di(4-pyridyl)ethene, 1,3-di(4-pyridyl)propane, 1,2-di(4-pyridyloxy)ethane, di(2-pyridyl)ketone, 4,4'-dipyridyl sulfide, 4,4'-dipyridyl disulfide, 2,2'-dipyridylamine, 2,2'-dipicolylamine, and bipyridine. Preferred are aromatic amines such as diisopropylaniline, and more preferred is 2,6-diisopropylaniline. Examples of the ammonium salt include tetramethylammonium hydroxide, tetraisopropylammonium hydroxide, tetrabutylammonium hydroxide, tetrahexylammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethylammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium hydroxide, tetra-n-butylammonium salicylate, choline, and the like.
[0188] The acidity of a salt that generates an acid with a lower acidity than the acid generated from the acid generator is represented by the acid dissociation constant (pKa). A salt that generates an acid with a lower acidity than the acid generated from the acid generator is a salt having an acid dissociation constant of the acid generated from the salt usually of -3 < pKa, preferably -1 < pKa < 7, and more preferably 0 < pKa < 5. Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator include a salt represented by the following formula, a salt represented by formula (D) described in JP-A-2015-147926 (hereinafter sometimes referred to as "weak acid inner salt (D)"), and salts described in JP-A-2012-229206, JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-39502, and JP-A-2011-191745. Preferably, it is a salt that generates a carboxylic acid with a lower acidity than the acid generated from the acid generator (a salt having a carboxylic acid anion), more preferably a weak acid inner salt (D), and still more preferably a diphenyliodonium salt containing a phenyl group substituted with a carboxylic acid anion among the weak acid inner salts (D). TIFF2026026043000149.tif96157
[0189] The weak acid inner salt (D) is preferably a diphenyliodonium salt having an iodonium cation to which two phenyl groups are bonded and a carboxylic acid anion substituted for at least one of the two phenyl groups bonded to the iodonium cation, and specifically, examples thereof include salts represented by the following formula.
[0190] TIFF2026026043000150.tif1874[In formula (D), R D1 and R D2 each independently represents a hydrocarbon group having 1 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 7 carbon atoms, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a nitro group, or a halogen atom. m' and n' each independently represent an integer of 0 to 4, and when m' is 2 or more, a plurality of R D1 may be the same or different, and when n' is 2 or more, a plurality of R D2 may be the same or different.] R D1 and R D2 Examples of the hydrocarbon group include a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups. Examples of the chain hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, and nonyl groups. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and may be either saturated or unsaturated. Examples of the alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclononyl, and cyclododecyl, norbornyl, and adamantyl. Examples of aromatic hydrocarbon groups include aryl groups such as a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a 4-propylphenyl group, a 4-isopropylphenyl group, a 4-butylphenyl group, a 4-t-butylphenyl group, a 4-hexylphenyl group, a 4-cyclohexylphenyl group, an anthryl group, a p-adamantylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group. Examples of groups formed by combining these groups include alkyl-cycloalkyl groups, cycloalkyl-alkyl groups, and aralkyl groups (e.g., phenylmethyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl-1-propyl group, 1-phenyl-2-propyl group, 2-phenyl-2-propyl group, 3-phenyl-1-propyl group, 4-phenyl-1-butyl group, 5-phenyl-1-pentyl group, and 6-phenyl-1-hexyl group). Examples of the alkoxy group include a methoxy group and an ethoxy group. Examples of the acyl group include an acetyl group, a propanoyl group, a benzoyl group, and a cyclohexanecarbonyl group. Examples of the acyloxy group include groups in which an oxy group (—O—) is bonded to the above-mentioned acyl group. Examples of the alkoxycarbonyl group include a group in which a carbonyl group (—CO—) is bonded to the above alkoxy group. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. R D1 and R D2 are each independently preferably an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 4 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, an alkoxycarbonyl group having 2 ...
Claims
1. A resist composition containing a resin containing a structural unit represented by formula (IP): [In the formula (IP), R 0 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X 10 represents a single bond, or —O—, —CO—, —S—, —SO—, or —SO 2 -, -NR 5 -, a phenylene group which may have a substituent, or a group in which these are combined. R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 2 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or a heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms which may have a substituent. A 1 represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 It may be replaced with -. R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or a heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms. R 1 is a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents Ar 1 is a group derived from a benzene ring, two or more R 1 At least two R 1 does not substitute adjacently with a group derived from a benzene ring. X 1 and X 2 each independently represents *-CO-O-, *-O-CO-, *-O-CO-O- or *-O-. R 10 represents an acid labile group. 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-. mm1 represents an integer of 2 to 5, and a plurality of R 1 may be the same or different from each other. R 4 represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 It may be replaced with -. m4 represents an integer of 0 to 3, and when m4 is 2 or more, a plurality of R 4 may be the same or different from each other. mm2 represents an integer of 1 to 5, and when mm2 is an integer of 2 or more, the groups in the parentheses may be the same or different.
2. X 10 is a single bond or a group represented by the formula (X 10 -1) ~Formula (X 10 2. The resist composition according to claim 1, wherein the aryl group is a group represented by any one of the following formulas: [Formula (X)] 10 -1) ~ Equation (X) 10 -10) in the middle, *, ** are binding sites, * is R 0 represents the bonding site with the carbon atom to which it is attached. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4. When mx is 2 or more, multiple Rx's may be the same or different. X 20 is —O— or —NR 5 Represents -. R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
3. X 10 is a single bond or a group represented by the formula (X 10 -1′) and formula (X 10 -3') ~Formula (X 10 3. The resist composition according to claim 1, wherein the aryl group is a group represented by any one of the following formulas: [Formula (X 10 -1′) and formula (X 10 -3') ~Formula (X 10 -10') medium, * and ** represent binding sites, * represents R 0 represents the bonding site between the carbon atom bonded to
4. 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 represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 - may be replaced by . *** is Ar 1 The resist composition according to claim 1 or 2, wherein the compound (I) represents a bonding site with
5. X 01 5. The resist composition according to claim 4, wherein is —O—, —CO—, or —S—.
6. L 01 is a single bond or an alkanediyl group having 1 to 6 carbon atoms (the —CH 2 5. The resist composition according to claim 4, 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 3. The resist composition according to claim 1, wherein the aryl group is a aryl group, and the aryl group is a aryl group.
8. R 10 3. The resist composition 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. Ar 1 3. The resist composition according to claim 1, wherein is a group derived from a benzene ring.
10. 3. The resist composition according to claim 1, further comprising an acid generator, 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 when nb5 is 3, 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.
11. 3. The resist composition according to claim 1, wherein the resin 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 - is -O-, -CO- or -NR a18 May be replaced with -. R a18 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a1 represents a single bond or a carbonyl group. R a34 and R a35 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a36 represents a hydrocarbon group having 1 to 20 carbon atoms, or R 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.]
12. 3. The resist composition according to claim 1, wherein the resin comprises a structural unit represented by formula (a2-A). [In formula (a2-A), R a2 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a27 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and —CH 2 - is -O-, -CO- or -NR a28 May be replaced with -. R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a2 represents a single bond or a carbonyl group. nA2 represents an integer of 1 to 5, and when nA2 is 2 or more, the groups in the parentheses may be the same or different. na21 represents an integer of 0 to 4, and when na21 is 2 or more, a plurality of R a27 may be the same or different from each other. mc represents an integer of 0 to 2.
13. 3. The resist composition according to claim 1, wherein the resin comprises a structural unit represented by formula (a1-6) and a structural unit represented by formula (a2-A). [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.] [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 - is -O-, -CO- or -NR a28 May be replaced with -. R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a2 represents a single bond or a carbonyl group. nA2 represents an integer of 1 to 5, and when nA2 is 2 or more, the groups in the parentheses may be the same or different. na21 represents an integer of 0 to 4, and when na21 is 2 or more, a plurality of R a27 may be the same or different from each other. mc represents an integer of 0 to 2.
14. 11. The resist composition according to claim 10, further comprising a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator.
15. (1) a step of applying the resist composition according to claim 1 or 2 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:
16. A resin comprising a structural unit represented by formula (IP): [In the formula (IP), R 0 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X 10 represents a single bond, or —O—, —CO—, —S—, —SO—, or —SO 2 -, -NR 5 -, a phenylene group which may have a substituent, or a group in which these are combined. R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 2 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or a heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms which may have a substituent. A 1 represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 It may be replaced with -. R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or a heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms. R 1 is a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents Ar 1 is a group derived from a benzene ring, two or more R 1 At least two R 1 does not substitute adjacently with a group derived from a benzene ring. X 1 and X 2 each independently represents *-CO-O-, *-O-CO-, *-O-CO-O- or *-O-. R 10 represents an acid labile group. 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-. mm1 represents an integer of 2 to 5, and a plurality of R 1 may be the same or different from each other. R 4 represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 It may be replaced with -. m4 represents an integer of 0 to 3, and when m4 is 2 or more, a plurality of R 4 may be the same or different from each other. mm2 represents an integer of 1 to 5, and when mm2 is an integer of 2 or more, the groups in the parentheses may be the same or different.
17. A compound represented by formula (I): [In formula (I), R 0 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X 10 represents a single bond, or —O—, —CO—, —S—, —SO—, or —SO 2 -, -NR 5 -, a phenylene group which may have a substituent, or a group in which these are combined. R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 2 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, or a heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms which may have a substituent. A 1 represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may have a substituent. 2 - is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 It may be replaced with -. R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ar 1 represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or a heterocyclic aromatic hydrocarbon group having 4 to 9 carbon atoms. R 1 is a hydroxy group, *-X 1 -R 10 or *-X 2 -L 11 -X 1 -R 10 represents Ar 1 is a group derived from a benzene ring, two or more R 1 At least two R 1 does not substitute adjacently with a group derived from a benzene ring. 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. mm1 represents an integer of 2 to 5, and a plurality of R 1 may be the same or different from each other. R 4 represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -CO-, -S-, -SO-, -NR 11 -or-SO 2 It may be replaced with -. m4 represents an integer of 0 to 3, and when m4 is 2 or more, a plurality of R 4 may be the same or different from each other. mm2 represents an integer of 1 to 5, and when mm2 is an integer of 2 or more, the groups in the parentheses may be the same or different.
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Patent Citations
Resin, resist composition, method for producing resist pattern, and compound
JP2021130807A