Methods for manufacturing resist compositions and resist patterns, and compounds
The resist composition, comprising compounds of formula (I) and other additives, addresses the issue of poor LER in existing resist patterns by enhancing the manufacturing process to achieve improved LER in the resulting patterns.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- SUMITOMO CHEM CO LTD
- Filing Date
- 2025-11-14
- Publication Date
- 2026-05-28
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Figure 2026088086000001 
Figure 2026088086000002 
Figure 2026088086000003
Abstract
Description
[Technical Field]
[0001] The present invention relates to a resist composition, a method for producing a resist pattern using the resist composition, and compounds. [Background technology]
[0002] Patent Document 1 describes a compound with the following structural formula. Patent document 2 (TIFF2026088086000001.tif2377) describes a compound with the following structural formula. TIFF2026088086000002.tif2690 [Prior art documents] [Patent Documents]
[0003] [Patent Document 1] US2005 / 224753 publication [Patent Document 2] Japanese Patent Publication No. 2012-211322 [Overview of the Initiative] [Problems that the invention aims to solve]
[0004] The objective is to provide a resist composition that forms a resist pattern with better line edge roughness (LER) than a resist pattern formed from a resist composition containing the above-mentioned compound. [Means for solving the problem]
[0005] This invention includes the following inventions. [1] A resist composition containing a compound represented by formula (I). TIFF2026088086000003.tif37162 [In formula (I), R 5A is, -X 1A -R 10A or -X 1A -L 10A -X2A -R 10A represents. R 5B is -X 1B -R 10B or -X 1B -L 10B -X 2B -R 10B represents. X 1A X 2A X 1B and X 2B each independently represents -O-, -CO-, -S-, -SO-, -SO2-, -NR 7 - or a group formed by combining these. R 7 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L 10A and L 10B each independently represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR 7 -. or -CO-. R 10A and R 10B each independently represents a group represented by formula (IA) or a group represented by formula (IB). L 1A L 1B L 2 L 3 L 4 and L 5 each independently represents a single bond or a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR 7 -. or -CO-. X 2 and X 3 each independently represents -O-, -CO-, -S-, -SO-, -SO2-, -NR 7 -. or a group formed by combining these. Ar 1 and Ar 2 each independently represents a polycyclic aromatic hydrocarbon group having 8 to 24 carbon atoms. A 1 - represents a cyclic hydrocarbon group having 3 to 36 carbon atoms, which may have substituents, and -CH2- contained in the cyclic hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO- may be used instead. R 3 and R 6 Each of these independently represents a halogen atom or a hydrocarbon group having 1 to 48 carbon atoms, and the hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO- may be used instead. m3 represents an integer between 0 and 4, and when m3 is 2 or greater, multiple R 3 They may be identical or different from one another. m6 represents an integer between 0 and 4, and when m6 is 2 or greater, multiple R 6 They may be identical or different from one another. m4 represents an integer between 0 and 4, and when m4 is 2 or greater, the bases within the parentheses may be the same or different from each other. m5 represents an integer from 1 to 4, and when m5 is 2 or greater, the bases within the parentheses may be the same or different from each other. m7 represents an integer between 1 and 3, and when m7 is 2 or greater, the bases within the parentheses may be the same or different from each other. TIFF2026088086000004.tif33109[In formulas (IA) and (IB), R A This represents a saturated hydrocarbon group with 1 to 12 carbon atoms. u1 represents an integer between 0 and 2, and if u1 is 2, multiple R A They are either identical or different. s1 represents either 1 or 2. t1 represents either 0 or 1, where the sum of s1 and t1 is either 1 or 2. s12 represents an integer between 0 and 2. t12 represents an integer between 0 and 2. However, the sum of s12 and t12 is an integer between 0 and 2. L 12 - represents a hydrocarbon group having 1 to 36 carbon atoms, which may have single bonds or substituents, and the -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO- may be used instead. L 13 - represents a hydrocarbon group having 1 to 36 carbon atoms, which may have substituents, and the -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO- may be used instead. * indicates a connection site. [2] L 1A , L 1B , L 2 and L 3 The resist composition according to [1], wherein each is independently a single bond or a chain hydrocarbon group having 1 to 4 carbon atoms. [3] L 4 and L 5 The resist composition according to [1] or [2], wherein each is independently a single bond, a chain hydrocarbon group having 1 to 6 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have substituents, or a group which is a combination thereof. [4] A 1 The resist composition according to any one of [1] to [3], wherein is an alicyclic hydrocarbon group having 3 to 12 carbon atoms which may have substituents (the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), an aromatic hydrocarbon group having 6 to 14 carbon atoms which may have substituents, or a group which is a combination thereof. [5] Ar 1 and Ar 2 The resist composition according to any one of [1] to [4], wherein the group is derived from a naphthalene ring. [6] A resist composition according to any one of [1] to [5], further comprising an acid generator, wherein the acid generator comprises a salt represented by formula (B1) or a salt represented by formula (B2). TIFF2026088086000005.tif1395[In formula (B1), L b1 represents a hydrocarbon group having a single bond or a substituent (nb1+1), and the -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, or -SO2-. L b2 represents a divalent hydrocarbon group having 1 to 24 carbon atoms, which may have single bonds or substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-. Y b1 represents a methyl group which may have substituents or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO-, -SO2- or -CO-. nb1 represents an integer between 1 and 6. When nb1 is 2 or greater, the bases within the parentheses may be the same or different. Z1 + This represents an organic cation. TIFF2026088086000006.tif1193[In formula (B2), A 1 represents a nitrogen atom or a carbon atom. L b2’ represents a divalent hydrocarbon group having 1 to 24 carbon atoms, which may have single bonds or substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-. Y b1’ represents a methyl group which may have substituents or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO- or -SO2-. nb5 represents an integer of 2 or 3. If nb5 is 2, then A 1 is a nitrogen atom, and if nb5 is 3, A 1is a carbon atom. The groups in parentheses may be the same or different from each other, and two groups in parentheses combine to form A 1 A ring containing the element may be formed. Z2 + This represents an organic cation. [7] A resist composition according to any one of [1] to [6], further comprising a compound containing a structure represented by formula (L0). TIFF2026088086000007.tif2471[In formula (L0), Ar lk This represents an aromatic hydrocarbon ring having 6 to 18 carbon atoms, which may have substituents. X lk This represents a single bond or a carbonyl group. R lk This represents a hydrogen atom or an acid-unstable group. lk represents an integer greater than or equal to 1, and when lk is 2 or greater, the bases within the parentheses may be the same or different. * indicates a connection site. lo represents an integer greater than or equal to 1. [8] The resist composition according to [7], wherein the compound containing the structure represented by formula (L0) is the compound represented by formula (LX). TIFF2026088086000008.tif24131[In formula (LX), Ar k1 and Ar k2 Each of these independently represents an aromatic hydrocarbon ring with 6 to 18 carbon atoms. X lk1 and X lk2 Each of these independently represents either a single bond or a carbonyl group. R lk1 and R lk2 Each of these independently represents either a hydrogen atom or an acid-unstable group. Lx represents a hydrocarbon group having 1 to 80 carbon atoms, which may have substituents, and the -CH2- contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 7 -It may also be replaced with -SO2-. R 7represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R lk11 and R lk22 each independently represents a halogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -S-, -SO-, -NR 7 -, or -SO2-, and R lk11 and R lk22 , R lk11 and Lx or R lk22 and Lx may each form a ring by bonding, the ring may have a substituent, and -CH2- contained in the ring may be replaced by -O-, -S-, -CO-, -SO-, -NR 7 -, or -SO2-. lx2 represents any integer from 1 to 6, and when lx2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk1’ represents any integer from 1 to 13, and when lk1’ is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk11’ represents any integer from 0 to 12, and when lk11’ is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk2’ represents any integer from 1 to 13, and when lk2’ is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. lk22’ represents any integer from 0 to 12, and when lk22’ is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other.] The resist composition according to [7] or [8], wherein the compound containing the structure represented by formula (L0) is a resin containing a structural unit represented by formula (a2 - A) or a structural unit represented by formula (a1 - 4). TIFF2026088086000009.tif30128[In formula (a2 - A), R a2 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a27represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group. A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a28 -. R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a2 represents a single bond or a carbonyl group. nA2 represents any integer from 1 to 5, and when nA2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. na21 represents any integer from 0 to 4, and when na21 is 2 or more, the plurality of R a27 may be the same as or different from each other. mc represents any integer from 0 to 2. TIFF2026088086000010.tif31118[In formula (a1-4), R a1 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a17 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group. A a11 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a18- may be replaced with this. R a18 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a1 This represents a single bond or a carbonyl group. na1 represents an integer between 1 and 5, and when na1 is 2 or greater, the bases within the parentheses may be the same or different from each other. na11 represents an integer from 0 to 4, and when na11 is 2 or greater, multiple R a17 They may be the same or different from one another. mc represents an integer between 0 and 2. R a34 and R a35 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R a36 This represents a hydrocarbon group with 1 to 20 carbon atoms, or R a34 R represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms. a35 and R a36 These groups bond to each other, forming a divalent heterocyclic group with 3 to 20 carbon atoms together with the -CO- groups to which they are bonded. The -CH2- groups contained in the hydrocarbon group and the divalent heterocyclic group may be replaced with -O- or -S- groups.
[10] The resist composition according to [9], wherein the resin further comprises at least one selected from the group consisting of structural units represented by formula (a1-0), structural units represented by formula (a1-1), structural units represented by formula (a1-2), structural units represented by formula (a1-5), and structural units represented by formula (a1-6). TIFF2026088086000011.tif44143[In formulas (a1-0), (a1-1), and (a1-2), L a01 , L a1 and L a2 These are, independently, -O- or *-O-(CH2) k1 -CO-O- represents a bond, where k1 is an integer from 1 to 7, and * represents the bond site with -CO-. R a01 , R a4 and R a5Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. R a02 , R a03 and R a04 Each of these independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, and the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have halogen atoms. R a6 and R a7 Each of these 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 a combination thereof, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have halogen atoms. m1' represents an integer between 0 and 14. n1 represents an integer between 0 and 14. n1' represents an integer between 0 and 3. TIFF2026088086000012.tif4558[In formula (a1-5), R a8 This represents an alkyl group having 1 to 6 carbon atoms, which may contain a halogen atom, a hydrogen atom, or a halogen atom. Z a1 This is a single bond or *-(CH2) h3 -CO-L 54 - represents, h3 represents an integer from 1 to 4, and * represents L 51 This represents the connection point. L 51 , L 52 , L 53 and L 54 These represent either -O- or -S- independently. s1 represents an integer between 1 and 3. s1' represents an integer between 0 and 3. TIFF2026088086000013.tif3581[In formula (a1-6), R a61This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain 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 substituents, or R a62 and R a63 They bond to each other, forming a ring with 3 to 20 carbon atoms, R a64 This represents an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms, which may have substituents. X a61 These are single bonds, -CO-O-*, or -CO-NR a65 -* represents the bonding site with Ar, and R a65 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 This is a single bond, *-OL a61 -or*-CO-OL a62 - represents the bonding site with Ar, and * represents the bonding site with L. a61 and L a62 Each of these independently represents an alkanediyl group with 1 to 4 carbon atoms. Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms, which may have substituents.
[11] (1) A step of applying a resist composition described in any of [1] to
[10] onto a substrate, (2) A step of drying the coated resist composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the composition layer after exposure, (5) A step of developing the composition layer after heating, A method for manufacturing a resist pattern that includes a resist pattern.
[12] A compound represented by the above formula (I). [Effects of the Invention]
[0006] By using the resist composition of the present invention, resist patterns can be manufactured with good line edge roughness (LER). [Modes for carrying out the invention]
[0007] In this specification, "(meth)acrylic monomer" means "at least one of acrylic monomers and methacrylic monomers." The same applies to "(meth)acrylate" and "(meth)acrylic acid," etc. For groups described herein that can take both linear and branched structures, either is acceptable. Hydrocarbon groups, etc., containing -CH2- are -O-, -S-, -CO-, -SO-, -NR 7 When a group is replaced by - or -SO2-, the same example shall apply to each group, and the number of carbon atoms before replacement shall be the same as the number of carbon atoms in the hydrocarbon group, etc. "Combined group" means a group formed by bonding two or more of the exemplified groups, and the valencies of these groups may be appropriately changed depending on the bonding configuration. "Derived from" or "induced" means that the polymerizable C=C bond contained in the molecule becomes 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 the group may be replaced at the bonding site. The number of carbon atoms in a substituent is not included in the number of carbon atoms of the substituent. "Acid-unstable group" means a group in which, upon contact with an acid (e.g., trifluoromethanesulfonic acid, etc.), the leaving group is removed to form a hydrophilic group (e.g., a hydroxyl group or a carboxyl group, etc.). A "base-unstable group" refers to a group that, upon contact with a base (e.g., trimethylamine, tetramethylammonium hydroxide, etc.), detaches a leaving group to form a hydrophilic group (e.g., a carboxyl group or a hydroxyl group, etc.). In this specification, "solid content of the resist composition" means the total amount of the resist composition excluding the solvent (E) described later.
[0008] <Resist Composition> The resist composition of the present invention contains 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 compound containing a structure represented by formula (L0) (hereinafter sometimes referred to as "compound (L0)") or resin, another resin (hereinafter sometimes referred to as "resin (A)" or "resin (X)"), a quencher such as a salt that generates an acid with a lower acidity than the acid generated from the acid generator (hereinafter sometimes referred to as "quencher (C)"). The resist composition of the present invention preferably contains a solvent (hereinafter sometimes referred to as "solvent (E)").
[0009] <Compound (I)> The resist composition of the present invention contains compound (I). TIFF2026088086000014.tif37163[In formula (I), all signs have the same meaning as defined above.]
[0010] R 5A and R 5B X included 1A and X 1B These are -O-, -CO-, and -NR, respectively, independently. 7 -Or combinations thereof include groups such as *-CO-O-, *-O-CO-, *-O-CO-O-, and *-CO-NR 7 -, *-NR 7 -CO-, *-NR 7 -CO-O-, *-O-CO-NR 7 - or *-O- is preferred, *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- is more preferred, and *-O-CO-O- or *-O- is even more preferred. * is L 1A or L 1B This represents the connection point. R 5A and R 5B X included 2A and X 2B These are -O-, -CO-, and -NR, respectively, independently. 7-Or combinations thereof include groups such as *-CO-O-, *-O-CO-, *-O-CO-O-, and *-CO-NR 7 -, *-NR 7 -CO-, *-NR 7 -CO-O-, *-O-CO-NR 7 - or *-O- is preferred, *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- is more preferred, and *-CO-O- or *-O-CO- is even more preferred. * is L 10A or L 10B This represents the connection point. R 7 Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. R 7 The hydrogen atom or an alkyl group having 1 to 4 carbon atoms is preferred, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms is more preferred, a hydrogen atom, an ethyl group or a methyl group is even more preferred, and a hydrogen atom or a methyl group is even more preferred.
[0011] R 5A L contained in 10A and R 5B L contained in 10B The hydrocarbon group in this formula may be saturated or unsaturated, and may include linear or branched chain hydrocarbon groups such as alkanediyl groups, monocyclic or polycyclic (including spiro rings, fused rings, or cross-linking rings) alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. A group formed by combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and a chain hydrocarbon group) is also acceptable. Chain hydrocarbon groups and alicyclic hydrocarbon groups are also called aliphatic hydrocarbon groups, and alicyclic hydrocarbon groups and aromatic hydrocarbon groups are also called cyclic hydrocarbon groups. The number of carbon atoms in the hydrocarbon group is preferably 1 to 24, more preferably 1 to 20, even more preferably 1 to 18, even more preferably 1 to 12, even more preferably 1 to 10, even more preferably 1 to 8, and even more preferably 1 to 6. Examples of alkanediyl groups include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group and heptadecane-1,17-diyl group, and Examples of branched alkanediyl groups include ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. The ends of the branched alkanediyl groups may be alkyl groups such as methyl groups. The number of carbon atoms in the chain-like hydrocarbon group may be 1 to 24, preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, even more preferably 1 to 8, even more preferably 1 to 6, and even more preferably 1 to 4. Examples of monocyclic or polycyclic alicyclic hydrocarbon groups include the following groups. The bonding site can be at any position. TIFF2026088086000015.tif45164 Specifically, as alicyclic hydrocarbon groups, monocyclic divalent alicyclic hydrocarbon groups such as monocyclic cycloalkanediyl groups like cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, and cyclooctane-1,5-diyl group, and Examples of polycyclic divalent alicyclic hydrocarbon groups include cycloalkyl groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, spirocyclohexane-1,2'-cyclopentane group, and spiroadamantane-2,3'-cyclopentane group, as well as polycyclic cycloalkanediyl groups such as spiro rings having cycloalkyl groups spiro-bonded to norbornyl or adamantyl groups. The number of carbon atoms in the alicyclic hydrocarbon group may be 3 to 24, preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. Examples of aromatic hydrocarbon groups include phenylene groups, naphthylene groups, anthrylene groups, biphenylene groups, phenanthrylene groups, and other arylene groups. The number of carbon atoms in the aromatic hydrocarbon group may be 6 to 24, preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10. Examples of groups formed by combining two or more types include groups formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group, groups formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group, groups formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, and groups formed by combining an alicyclic hydrocarbon group, an aromatic hydrocarbon group and a chain hydrocarbon group. In these combinations, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. Examples of groups that combine an alicyclic hydrocarbon group and a chain hydrocarbon 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 that combine an aromatic hydrocarbon group and a chain-type hydrocarbon 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 10A and L 10B The -CH2- groups contained in hydrocarbon groups with 1 to 28 carbon atoms are -O-, -S-, -SO2-, -SO-, and -NR. 7 - or -CO- may be used instead. L 10A and L 10B The -CH2- group in the hydrocarbon group with 1 to 28 carbon atoms is -O-, -S-, -SO2-, -SO-, -NR 7 If it is replaced by - or -CO-, the number of carbon atoms before replacement shall be the number of carbon atoms of the hydrocarbon group. The -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 Groups replaced by - or -CO- include hydroxyl groups (groups in which the -CH2- contained in the methyl group is replaced by -O-), carboxyl groups (groups in which the -CH2-CH2- contained in the ethyl group is replaced by -O-CO-), thiol groups (groups in which the -CH2- contained in the methyl group is replaced by -S-), and amino groups (groups in which the -CH2- contained in the methyl group is replaced by -NR 7 - group replaced by -, oxy group (a group in which -CH2- in the methylene group is replaced by -O-), carbonyl group (a group in which -CH2- in the methylene group is replaced by -CO-), thio group (a group in which -CH2- in the methylene group is replaced by -S-), sulfonyl group (a group in which -CH2- in the methylene group is replaced by -SO2-), peptide group (a group in which -CH2-CH2- in the ethylene group is replaced by -CO-NR 7-A group replaced by -), alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced by -S-), alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced by -SO2-), alkylamino group (a group in which -CH2- at any position in an alkyl group is replaced by -NR 7 -A group replaced by -), alkyl peptide group (where -CH2-CH2- at any position within the alkyl group is -CO-NR 7عال (A group in which 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 one -CH2- at any position in an alkyl group is replaced by -O-), hydroxyalkyl group (A group in which one -CH2- in a methyl group at any position in an alkyl group is replaced by -O-), alkanediyloxy group (A group in which one -CH2- in an alkanediyl group is replaced by -O-) (A group in which the -CH2- at any position is replaced by -O-), Alkanediyloxycarbonyl group (A group in which the -CH2-CH2- at any position in the Alkanediyl group is replaced by -O-CO-), Alkanediylcarbonyl group (A group in which the -CH2- at any position in the Alkanediyl group is replaced by -CO-), Alkanediylcarbonyloxy group (A group in which the -CH2-CH2- at any position in the Alkanediyl group is replaced by -CO-O-), Alkanediyl Xycarbonyloxy 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 7 -A group replaced by -), an alkanediyl peptide group (where -CH2-CH2- at any position in the alkanediyl group is replaced by -CO-NR 7Examples include groups that have been replaced by (-), cycloalkoxy groups, cycloalkylalkoxy groups, aromatic hydrocarbon group-carbonyloxy groups, aromatic hydrocarbon group-carbonyl groups, aromatic hydrocarbon group-oxy groups, and groups that combine two or more of these groups. Examples of alkoxy groups include alkoxy groups having 1 to 27 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, and undecyloxy groups. 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. Examples of alkylthio groups include alkylthio groups having 1 to 27 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, and undecylthio group. 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 even more preferably 1 to 3. Examples of alkylamino groups include alkylamino groups having 1 to 27 carbon atoms, such as methylamino group, ethylamino group, dimethylamino group, propylamino group, butylamino group, pentylamino group, pentylamino group, and hexylamino group. 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 even more preferably 1 to 3. Examples of alkyl peptide groups include alkyl peptide groups having 1 to 27 carbon atoms, such as methyl peptide groups, ethyl peptide groups, and propyl peptide groups. 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 alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 27 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl groups. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 28 carbon atoms, such as acetyl, propionyl, and butyryl groups. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 27 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy groups. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 26 carbon atoms, such as butoxycarbonyloxy groups. Examples of alkoxyalkoxy groups include alkoxyalkoxy groups having 2 to 26 carbon atoms, such as methoxymethoxy, methoxyethoxy, ethoxymethoxy, and ethoxyethoxy groups. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkoxycarbonyloxy 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 alkoxyalkoxy group is preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of alkylsulfonyl groups include alkylsulfonyl groups having 1 to 27 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, octylsulfonyl group, 2-ethylhexylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, and undecylsulfonyl group. 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 even more preferably 1 to 3. Examples of alkoxyalkyl groups include alkoxyalkyl groups having 2 to 27 carbon atoms, such as methoxymethyl group, methoxyethyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, ethoxybutyl group, propoxymethyl group, propoxyethyl group, isopropoxymethyl group, propoxypropyl group, butoxymethyl group, sec-butoxymethyl group, and tert-butoxymethyl group. The number of carbon atoms in the alkoxyalkyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of hydroxyalkyl groups include hydroxyalkyl groups having 1 to 27 carbon atoms, such as hydroxymethyl group, dihydroxymethyl group, hydroxyethyl group, dihydroxyethyl group, hydroxypropyl group, hydroxyisopropyl group, hydroxybutyl group, and hydroxysec-butyl group. The number of carbon atoms in the hydroxyalkyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Examples of alkanediyloxy groups include alkanediyloxy groups having 1 to 27 carbon atoms, such as methyleneoxy, ethyleneoxy, propanediyloxy, butanediyloxy, and pentanediyloxy groups. 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 even more preferably 1 to 3. Examples of alkanediyloxycarbonyl groups include alkanediyloxycarbonyl groups having 2 to 27 carbon atoms, such as methyleneoxycarbonyl groups, ethyleneoxycarbonyl groups, propanediyloxycarbonyl groups, and butanediyloxycarbonyl groups. Examples of alkanediylcarbonyl groups include alkanediylcarbonyl groups having 2 to 28 carbon atoms, such as methylenecarbonyl groups, ethylenecarbonyl groups, propanediylcarbonyl groups, butanediylcarbonyl groups, and pentanediylcarbonyl groups. Examples of alkanediylcarbonyloxy groups include alkanediylcarbonyloxy groups having 2 to 27 carbon atoms, such as methylenecarbonyloxy groups, ethylenecarbonyloxy groups, propanediylcarbonyloxy groups, and butanediylcarbonyloxy groups. Examples of alkanediyloxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 26 carbon atoms, such as the butoxycarbonyloxy group. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. Examples of alkanediylsulfonyl groups include alkanediylsulfonyl groups having 1 to 27 carbon atoms, such as methylenesulfonyl groups, ethylenesulfonyl groups, and propylenesulfonyl groups. 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 even more preferably 1 to 3. Examples of alkanediylthio groups include alkanediylthio groups having 1 to 27 carbon atoms, such as methylenethio groups, ethylenethio groups, and propylenethio groups. 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 even more preferably 1 to 3. Examples of alkanediylamino groups include alkanediylamino groups having 1 to 27 carbon atoms, such as methyleneamino groups, ethyleneamino groups, dimethylamino groups, propyleneamino groups, butyleneamino groups, pentyleneamino groups, and hexyleneamino groups. 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 even more preferably 1 to 3. Examples of alkanediyl peptide groups include alkanediyl peptide groups having 1 to 27 carbon atoms, such as methylene peptide groups, ethylene peptide groups, and propylene peptide groups. 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 even more preferably 1 to 3. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 27 carbon atoms, such as the cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 27 carbon atoms, such as the cyclohexylmethoxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 27 carbon atoms, such as the benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 28 carbon atoms, such as the benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 27 carbon atoms, such as the phenyloxy group.
[0012] Furthermore, the -CH2- contained in alicyclic hydrocarbon groups, aromatic hydrocarbon groups, or combinations thereof may be -O-, -S-, -CO-, -SO-, -NR 7The following are examples of groups that have been replaced by - or -SO2-. The -O- or -CO- in the groups shown below are replaced by -S- and -NR, respectively. 7 -, -SO-, or -SO2- may be substituted. The binding site can be at any position. TIFF2026088086000016.tif89165
[0013] L 10A and L 10B Examples of substituents that may be present include halogen atoms, cyano groups, nitro groups, etc. 10A and L 10B However, in the case of a group that combines an alicyclic hydrocarbon group or an aromatic hydrocarbon group with a chain hydrocarbon group such as an alkyl group, the chain hydrocarbon group such as an alkyl group can be substantially substituted for the alicyclic hydrocarbon group or aromatic hydrocarbon group. 10A and L 10B The -CH2- group contained in the alkyl group and other chain hydrocarbon groups is -O-, -CO-, -S-, -SO-, -NR 7 -By being replaced by -SO2-, L 10A and L 10B It can substantially have substituents such as hydroxyl groups, carboxyl groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, alkoxyalkoxy groups, thiol groups, alkylthio groups, alkylsulfonyl groups, amino groups, alkylamino groups, and alkylpeptide groups. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. L 10A and L 10B The substituents that may be present include C1-C6 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-) or halogen atoms, preferably C1-C4 alkyl groups, hydroxyl groups, or halogen atoms, more preferably C1-C4 alkyl groups or halogen atoms, and even more preferably methyl groups or fluorine atoms.
[0014] L 10A and L 10B Each of these can be independently a chain-like hydrocarbon group having 1 to 18 carbon atoms (the chain-like hydrocarbon group may have substituents. The -CH2- contained in the chain-like hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -or may be replaced by -CO-), a cyclic hydrocarbon group having 3 to 20 carbon atoms (the cyclic hydrocarbon group may have substituents. -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO- may be replaced.) or a group formed by combining a chain hydrocarbon group having 1 to 12 carbon atoms and a cyclic hydrocarbon group having 3 to 20 carbon atoms (the chain hydrocarbon group and the cyclic hydrocarbon group may have substituents. The -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -Or -CO- may be replaced by -CH2-, -S-, -SO2-, -SO-, -NR 7 - or -CO- may be replaced.) or a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the chain hydrocarbon group and the alicyclic hydrocarbon group may have substituents. The -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7It is preferable that the group is a C1-C10 alkanediyl group (the alkanediyl group may have substituents; the -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-) or a group formed by combining a C1-C4 alkanediyl group and a C3-C12 alicyclic hydrocarbon group (the alkanediyl group and the alicyclic hydrocarbon group may have substituents; the -CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-), it is more preferable that the group is a C1-C6 alkanediyl group or a group formed by combining a C1-C3 alkanediyl group and a C3-C12 alicyclic hydrocarbon group, it is even more preferable that the group is a C1-C3 alkanediyl group, and it is even more preferable that the group is a methylene group.
[0015] R 5A R included 10A and R 5B R included 10B R is a group represented by formula (IA) or formula (IB). 10A and R 10B They may be the same or different from one another. TIFF2026088086000017.tif33109[In formulas (IA) and (IB), R A This represents a saturated hydrocarbon group with 1 to 12 carbon atoms. u1 represents an integer between 0 and 2, and if u1 is 2, multiple R A They are either identical or different. s1 represents either 1 or 2. t1 represents either 0 or 1, where the sum of s1 and t1 is either 1 or 2. s12 represents an integer between 0 and 2. t12 represents an integer between 0 and 2. However, the sum of s12 and t12 is an integer between 0 and 2. L 12- represents a hydrocarbon group having 1 to 36 carbon atoms, which may have single bonds or substituents, and the -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO- may be used instead. L 13 - represents a hydrocarbon group having 1 to 36 carbon atoms, which may have substituents, and the -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO- may be used instead. * indicates a connection site.
[0016] R A Examples of saturated hydrocarbon groups include chain-type saturated hydrocarbon groups such as alkyl groups, alicyclic saturated hydrocarbon groups, and groups that combine two or more of these. R A Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, and nonyl groups. The number of carbon atoms in the chain-like saturated hydrocarbon group may be 1 to 24, preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, even more preferably 1 to 9, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic saturated hydrocarbon group may be monocyclic, polycyclic, or spirocyclic. Examples of alicyclic saturated hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl groups, and polycyclic cycloalkyl groups such as norbornyl and adamantyl groups. The number of carbon atoms in the alicyclic saturated hydrocarbon group may be 3 to 24, preferably 3 to 18, more preferably 3 to 16, even more preferably 3 to 12, even more preferably 3 to 10, even more preferably 3 to 8, and even more preferably 3 to 6. The combined group may be a group formed by combining one chain-type saturated hydrocarbon group and one alicyclic saturated hydrocarbon group as described above, or a group formed by combining two or more of either or two or more of both.
[0017] L 12 and L 13 Examples of hydrocarbon groups having 1 to 36 carbon atoms include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkanediyl groups, alkenediyl groups, alkynediyl groups, alkantriyl groups, alkentriyl groups, alkynetriyl groups, and monocyclic or polycyclic alicyclic hydrocarbon groups), aromatic hydrocarbon groups, etc., and hydrocarbon groups formed by combining two or more of these groups may also be used. 12 L is a divalent hydrocarbon group. 13 L is a trivalent hydrocarbon group. 12 and L 13 The -CH2- groups in the hydrocarbon group are -O-, -S-, -CO-, -SO-, and -NR. 7 -It may be replaced with -SO2-. Examples of alkanediyl groups 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, and dodecane-1,12-diyl; Branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. These are some examples. Examples of alkanetriyl groups include those obtained by removing one hydrogen atom from the aforementioned alkanediyl group. Examples of alkenediyl groups include ethendiyl, propendiyl, isopropendiyl, butendiyl, isobutendiyl, tert-butendiyl, pentendiyl, hexendiyl, heptendiyl, octendiyl, isooctenediyl, and nonendiyl. Examples of alkenetriyl groups include those obtained by removing one hydrogen atom from the aforementioned alkenediyl group. Examples of alkynediyl groups include ethindiyl group, propindiyl group, isopropindiyl group, butindiyl group, isobutindiyl group, tert-butindiyl group, pentindiyl group, hexindiyl group, octindiyl group, and nonindiyl group. Examples of alkyntriyl groups include those obtained by removing one hydrogen atom from the aforementioned alkynediyl group. The number of carbon atoms in the chain-like hydrocarbon group can be 1 to 30, may be 1 to 24, preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 9, even more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 to 3.
[0018] L 12 and L 13 The -CH2- contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 7 -If replaced by -SO2-, the number of carbon atoms before replacement is L 12 and L 13 This is the total number of carbon atoms in the hydrocarbon group. This number may be one or two or more. The -CH2- contained in the alkanediyl group is -O-, -S-, -CO-, -SO-, -NR 7Groups replaced by - or -SO2- include hydroxyl groups, carboxyl groups, oxy groups, carbonyl groups, thio groups, sulfonyl groups, thiol groups, amino groups, peptide groups, alkanediyloxy groups, alkanediyloxycarbonyl groups, alkanediylcarbonyl groups, alkanediylcarbonyloxy groups, alkanediyloxycarbonyloxy groups, alkanediylthio groups, alkanediylsulfonyl groups, alkanediylamino groups, alkanediylpeptide groups, and groups combining two or more of these groups. These replaced groups are similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. Groups obtained by removing one hydrogen atom from these groups are also included. Furthermore, the substitutions in the alkanediyl group and alkynediyl group may include carbon-carbon double bonds or carbon-carbon triple bonds at any position in the examples of substitutions in the alkanediyl group described above.
[0019] The alicyclic hydrocarbon group may be monocyclic or polycyclic, and examples include the groups shown below. The bonding site can be at any position. Specifically, monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclohexene-3,6-diyl group, and cyclooctane-1,5-diyl group, while polycyclic alicyclic hydrocarbon groups include norbornane-1,4-diyl group and norbornane Examples include polycyclic cycloalkanediyl groups such as -2,5-diyl group, 5-norbornene-2,3-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group; cycloalkyl groups such as spirocyclohexane-1,2'-cyclopentane group and spiroadamantane-2,3'-cyclopentane group; and spiro rings having a norbornyl group or an adamantyl group each linked to a cycloalkyl group by a spiro link. Another example is the group obtained by removing one hydrogen atom from the group described above. The number of carbon atoms in the alicyclic hydrocarbon group can be 3 to 30, but may also be 3 to 24, preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. The -CH2- contained in the alicyclic hydrocarbon group is -O-, -S-, -CO-, -SO-, -NR 7 Groups replaced with - or -SO2- include those similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. Examples of aromatic hydrocarbon groups include phenylene groups, naphthylene groups, anthrylene groups, biphenylene groups, and phenanthrylene groups. Another example is the group obtained by removing one hydrogen atom from the group described above. The number of carbon atoms in the aromatic hydrocarbon group can range from 6 to 30, may be 6 to 24, preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10. The -CH2- group contained in the aromatic hydrocarbon group is -O-, -S-, -CO-, -SO-, -NR 7 Groups replaced with - or -SO2- include those similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms.
[0020] Examples of hydrocarbon groups formed by combining two or more groups include groups formed by combining a chain hydrocarbon group with an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group. In these combinations, two or more alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. For example, -alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-aromatic hydrocarbon group-, -aromatic hydrocarbon group-alkanediyl group-, etc. Any of these groups may be bonded to an oxygen atom or a carbonyl group, etc. The -CH2- contained in the combined group is -O-, -S-, -CO-, -SO-, -NR 7 Groups replaced with - or -SO2- include those similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms.
[0021] L 12 and L 13 Substituents on the hydrocarbon group include halogen atoms, cyano groups, hydroxyl groups, carboxyl groups, alkoxy groups having 1 to 12 carbon atoms, alkoxycarbonyl groups having 2 to 13 carbon atoms, alkylcarbonyl groups having 2 to 13 carbon atoms, alkylcarbonyloxy groups having 2 to 13 carbon atoms, alkoxycarbonyl groups having 2 to 13 carbon atoms, alkylcarbonyl groups having 2 to 13 carbon atoms, and alkylcarbonyloxy groups having 2 to 13 carbon atoms. These groups are similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms, etc. L 12 and L 13 The hydrocarbon group in may have one substituent or multiple substituents.
[0022] L 12 This refers to a chain-like hydrocarbon group having 1 to 12 carbon atoms, which may have single bonds or substituents (the -CH2- contained in the chain-like hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -or may be replaced by -CO-), a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -May be replaced by -CO-.) Or a group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have substituents and a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -Or may be replaced by -CO-.) Examples include single bonds, chain hydrocarbon groups having 1 to 6 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -or may be replaced by -CO-. ), alicyclic hydrocarbon groups having 3 to 18 carbon atoms (the -CH2- contained in the alicyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7-May be replaced by -CO-.) or a group combining a chain hydrocarbon group having 1 to 6 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 It is preferably a C1-C6 alkanediyl group, more preferably a C1-C3 alkanediyl group, and even more preferably a methylene group. L 13 This refers to a chain-like hydrocarbon group having 1 to 12 carbon atoms, which may have substituents (the -CH2- contained in the chain-like hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -or may be replaced by -CO-), a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -May be replaced by -CO-.) Or a group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have substituents and a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 Examples include chain hydrocarbon groups having 1 to 6 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -or may be replaced by -CO-. ), alicyclic hydrocarbon groups having 3 to 18 carbon atoms (the -CH2- contained in the alicyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -May be replaced by -CO-.) or a group combining a chain hydrocarbon group having 1 to 6 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7It is preferable that it is a C1-C6 alkanetriyl group, more preferably a C1-C3 alkanetriyl group, and even more preferably a methanetriyl group or an ethanetriyl group.
[0023] It is preferable that s1 is 1, t1 is 1, and the sum of s1 and t1 is 2. s12 is preferably 0 or 1, t12 is preferably 0 or 1, and the sum of s12 and t12 is preferably 0 or 1. The group represented by formula (IA) is preferably the group represented by the following: The group represented by formula (IB) in TIFF2026088086000019.tif19147 is preferably the group represented by the following: TIFF2026088086000020.tif23142
[0024] In the base represented by formula (IA), u1 is 1, R A is L 12 A group bonded to an adjacent carbon atom is represented by the following formula. TIFF2026088086000021.tif3144[In this formula, all signs have the same meaning as defined above.]
[0025] R 10A and R 10B The following are examples of such elements. TIFF2026088086000022.tif107151
[0026] L 1A , L 1B , L 2 , L 3 , L 4 and L 5 The hydrocarbon group in the hydrocarbon group, the substituents that the hydrocarbon group may have, and the -CH2- contained in the hydrocarbon group are -O-, -S-, -SO2-, -SO-, -NR 7- or -CO- is a group that has been replaced by L 10A and L 10B Examples of groups similar to those exemplified above include the following. Note L 5 The hydrocarbon group in this expression is a (m7+1) valent hydrocarbon group, and depending on m7, it can be a 2- to 4 valent hydrocarbon group. In addition to the groups mentioned above, these groups also include groups in which one or more hydrogen atoms of the aforementioned groups are replaced at the bonding site. L 1A , L 1B , L 2 and L 3 Each of these independently comprises a single bond and a chain hydrocarbon group having 1 to 12 carbon atoms, which may have substituents (the -CH2- contained in the chain hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -or may be replaced by -CO-), a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -May be replaced by -CO-.) Or a group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have substituents and a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 Examples include - or -CO- which may be replaced by -CH2-, -S-, -SO2-, -SO-, -NR 7 It is preferable that it is a chain hydrocarbon group having 1 to 6 carbon atoms, which may have single bonds or substituents, even more preferably a chain hydrocarbon group having 1 to 4 carbon atoms, which may have single bonds or halogen atoms, and still more preferably a chain hydrocarbon group having single bonds or 1 to 4 carbon atoms. L 4 and L 5Each of these independently comprises a single bond and a chain hydrocarbon group having 1 to 12 carbon atoms, which may have substituents (the -CH2- contained in the chain hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -or may be replaced by -CO-), a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -May be replaced by -CO-.) Or a group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have substituents and a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 -Or -CO- may be replaced by -CH2-, -S-, -SO2-, -SO-, -NR 7 -or may be replaced by -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have substituents (the -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7It is preferable that the group is a combination of the following: a chain hydrocarbon group having 1 to 8 carbon atoms, which may have single bonds or substituents (the -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 substituents (the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), an aromatic hydrocarbon group having 6 to 14 carbon atoms, which may have substituents, or a combination of the following: a chain hydrocarbon group having 1 to 8 carbon atoms, which may have single bonds or substituents It is more preferable that the group is a chain hydrocarbon group having 1 to 8 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an aromatic hydrocarbon group having 6 to 14 carbon atoms which may have substituents, or a group combining these, and it is even more preferable that the group is a single bond, a chain hydrocarbon group having 1 to 6 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have substituents, or a group combining these.
[0027] X 2 and X 3 These are -O-, -CO-, and -NR, respectively, independently. 7 -Or combinations thereof include groups such as *-CO-O-, *-O-CO-, *-O-CO-O-, and *-CO-NR 7 -, *-NR 7 -CO-, *-NR 7 -CO-O-, *-O-CO-NR 7 - or *-O- is preferred, and *-CO-O-, *-O-CO-, *-CO-NR 7 -or *-NR 7 -CO- is more preferable. * is L 2 or L 3 This represents the connection point. m4 is preferably an integer from 1 to 4, more preferably an integer from 1 to 3, and even more preferably 1 or 2. m5 is preferably an integer from 1 to 3, and more preferably 1 or 2. m7 is preferably 1 or 2, and more preferably 1.
[0028] Ar 1 and Ar 2 Examples of polycyclic aromatic hydrocarbon groups having 8 to 24 carbon atoms include groups derived from a naphthalene ring, anthracene ring, indene ring, phenanthrene ring, fluorene ring, or diphenylmethane ring, with the group being preferably derived from a naphthalene ring or anthracene ring, and more preferably from a naphthalene ring. The number of carbon atoms in the polycyclic aromatic hydrocarbon group is preferably 8 to 20, more preferably 8 to 18, even more preferably 9 to 18, even more preferably 10 to 18, and even more preferably 10 to 14.
[0029] A 1 The cyclic hydrocarbon group having 3 to 36 carbon atoms may be saturated or unsaturated, monocyclic or polycyclic, and polycyclic cyclic hydrocarbon groups may be bridged rings or form spiros. Examples of cyclic hydrocarbon groups include alicyclic hydrocarbon groups, aromatic hydrocarbon groups, or combinations thereof. Carbon atoms in alicyclic hydrocarbon groups may form double bonds between two adjacent carbon atoms. The number of carbon atoms in the cyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 24, and even more preferably 3 to 20. Examples of alicyclic hydrocarbon groups include the following. The bonding site can be at any position. Specifically, monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkanediyl groups such as cyclopropanediyl, cyclobutanediyl, cyclopentanediyl, cyclohexanediyl, cycloheptanediyl, cyclooctanediyl, and cyclodecanediyl. Polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkanediyl groups such as decahydronaphthanediyl, adamantanediyl, norbornanediyl, norbornenediyl, and bicyclo[3.3.0]octanediyl. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 3 to 12. Examples of aromatic hydrocarbon groups include phenylene groups, naphthylene groups, anthrylene groups, biphenylene groups, phenanthrylene groups, and other arylene groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Examples of combined groups include groups that combine alicyclic hydrocarbon groups and aromatic hydrocarbon groups, such as the following groups. TIFF2026088086000024.tif36160 In addition, groups obtained by replacing one or more hydrogen atoms of the above-mentioned groups with bonding sites can also be cited.
[0030] -CH2- contained in alicyclic hydrocarbon groups, aromatic hydrocarbon groups, or combinations thereof, are -O-, -S-, -CO-, -SO-, -NR 7 - or -SO2- may be replaced, and such replaced groups include those similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms, specifically the following groups. The -O- or -CO- in the groups shown below are replaced with -S- and -NR, respectively. 7 -, -SO-, or -SO2- may be substituted. The binding site can be at any position. TIFF2026088086000025.tif93166
[0031] A cyclic hydrocarbon group is a cyclic hydrocarbon group having 3 to 20 carbon atoms (the hydrogen atoms in the cyclic hydrocarbon group may be replaced by substituents, and the -CH2- groups in the cyclic hydrocarbon group may be -O-, -S-, -CO-, -SO-, -NR). 7 It is preferable that the group be an alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a combination thereof (the hydrogen atoms contained in the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be replaced by substituents, and the -CH2- contained in the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be -O-, -S-, -CO-, -SO-, -NR 7 It is more preferable that the group is represented by any of the formulas (w1-1) to (w1-35), and may be replaced by - or -SO2-. TIFF2026088086000026.tif87170[Formula (w1-1) to formula (w1-35), The hydrogen atoms in the group may be replaced by substituents, and the -CH2- groups in the group may be -O-, -S-, -CO-, -SO-, -NR 7 It may be replaced with - or -SO2-. The binding site is at any position.
[0032] A 1 The substituents of the cyclic hydrocarbon group contained therein include halogen atoms, C1-C6 haloalkyl groups, or C1-C12 alkyl groups (the -CH2- contained in the alkyl group is -O-, -S-, -CO-, -SO-, -NR 7 -It may be replaced with -SO2-.) etc. Also, -L 1A -R 5A They are equivalent. Examples of the halogen atoms mentioned above include fluorine, chlorine, bromine, and iodine atoms. The C1-C6 haloalkyl groups mentioned above include C1-C6 alkyl fluorides, C1-C6 alkyl chlorides, C1-C6 alkyl bromides, and C1-C6 alkyl iodides. Examples of haloalkyl groups include C1-C6 perfluoroalkyl groups (trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, iodomethyl group, fluoromethyl group, and difluoromethyl group. The number of carbon atoms in the haloalkyl group is preferably 1-4, and more preferably 1-3. Examples of alkyl groups having 1 to 12 carbon atoms as described above include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, and nonyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, even more preferably 1 to 6, and even more preferably 1 to 4. The -CH2- groups included in the alkyl groups mentioned above are -O-, -S-, -CO-, -SO-, and -NR. 7 If it is replaced by - or -SO2-, the number of carbon atoms before the replacement shall be the total number of carbon atoms of the alkyl group. Examples of the replaced groups include hydroxyl groups, carboxyl groups, oxy groups, carbonyl groups, thio groups, sulfonyl groups, peptide groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, alkoxyalkoxy groups, alkoxyalkyl groups, hydroxyalkyl groups, thiol groups, alkylthio groups, alkylsulfonyl groups, amino groups, alkylamino groups, alkylpeptide groups, and groups that combine two or more of these groups. These replaced groups are similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. The number of carbon atoms in these replaced groups is, for example, 11 or less, preferably 10 or less, more preferably 8 or less, even more preferably 6 or less, even more preferably 4 or less, and even more preferably 3 or less. A 1 The substituents that may be present include halogen atoms, C1-C4 haloalkyl groups, or C1-C8 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), preferably halogen atoms, C1-C3 haloalkyl groups, or C1-C6 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), more preferably fluorine atoms, iodine atoms, C1-C3 fluorinated alkyl groups, C1-C3 alkyl groups, hydroxyl groups, C1-C3 alkoxy groups, or carboxyl groups, and even more preferably fluorine atoms, iodine atoms, trifluoromethyl groups, methyl groups, ethyl groups, hydroxyl groups, methoxy groups, ethoxy groups, or carboxyl groups. 1 The number of substituents that it may have is not particularly limited. A 1 Preferably, the substituent is a cyclic hydrocarbon group having 3 to 20 carbon atoms that may have substituents (which may be replaced by -O- or -CO- contained in the cyclic hydrocarbon group), more preferably an alicyclic hydrocarbon group having 3 to 12 carbon atoms that may have substituents (which may be replaced by -O- or -CO- contained in the alicyclic hydrocarbon group), an aromatic hydrocarbon group having 6 to 14 carbon atoms that may have substituents, or a group that is a combination of these.
[0033] R 3 and R 6 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. R 3 and R 6 Examples of hydrocarbon groups having 1 to 48 carbon atoms include chain hydrocarbon groups such as alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. Chain hydrocarbon groups and alicyclic hydrocarbon groups are also called aliphatic hydrocarbon groups, and alicyclic hydrocarbon groups and aromatic hydrocarbon groups are also called cyclic hydrocarbon groups. The number of carbon atoms in the hydrocarbon group is preferably 1 to 36, more preferably 1 to 28, even more preferably 1 to 24, even more preferably 1 to 20, and even more preferably 1 to 18. Examples of alkyl groups include linear or branched alkyl groups, similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. The number of carbon atoms in the chain hydrocarbon group may be 1 to 36, preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 9, even more preferably 1 to 8, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be monocyclic or polycyclic, and examples similar to those exemplified herein are given, within the limits permitted by the upper limit of the number of carbon atoms. Specifically, monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl groups. Polycyclic alicyclic hydrocarbon groups include cycloalkyl groups such as decahydronaphthyl, adamantyl, norbornyl, spirocyclohexane-1,2'-cyclopentane, and spiroadamantane-2,3'-cyclopentane, as well as polycyclic cycloalkyl groups such as spiro rings having a cycloalkyl group spiro-bonded to a norbornyl or adamantyl group. The number of carbon atoms in the alicyclic hydrocarbon group may be 3 to 36, preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. Examples of aromatic hydrocarbon groups include phenyl groups, naphthyl groups, biphenyl groups, anthryl groups, phenanthryl groups, and binaphthyl groups. The number of carbon atoms in the aromatic hydrocarbon group may be 6 to 36, preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10.
[0034] Groups formed by combining these groups include groups formed by combining an aromatic hydrocarbon group with a chain hydrocarbon group (e.g., aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*, alkyl group-aromatic hydrocarbon group-alkanediyl group-*), groups formed by combining an alicyclic hydrocarbon group with a chain hydrocarbon group (e.g., alicyclic hydrocarbon group-alkanediyl group-*, alkyl group-alicyclic hydrocarbon group-*, alkyl group-alicyclic hydrocarbon group-alkanediyl group-*), and groups formed by combining an aromatic hydrocarbon group with an alicyclic hydrocarbon group (e.g., aromatic hydrocarbon group-alicyclic hydrocarbon group-*, alicyclic hydrocarbon group-aromatic hydrocarbon group-*). * indicates a bonding site. Examples of aromatic hydrocarbon groups - alkanediyl groups -* include aralkyl groups such as benzyl and phenethyl groups. Examples of alkyl-aromatic hydrocarbon groups-* include tolyl groups, xylyl groups, and cumenyl groups. Examples of alicyclic hydrocarbon groups - alkanediyl groups -* include cyclohexylmethyl group, cyclohexylethyl group, 1-(adamantan-1-yl)methyl group, 1-(adamantan-1-yl)-1-methylethyl group, and other cycloalkylalkyl groups. Examples of alkyl-alicyclic hydrocarbon groups include methylcyclohexyl group, dimethylcyclohexyl group, and cycloalkyl groups having alkyl groups such as 2-alkyladamantan-2-yl group. Examples of aromatic hydrocarbon groups - alicyclic hydrocarbon groups -* include the phenylcyclohexyl group. Examples of alicyclic hydrocarbon groups - aromatic hydrocarbon groups -* include the cyclohexylphenyl group. Furthermore, in the combinations, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. Also, any of the groups may be Ar 1 Or Ar 2 They may be bound together.
[0035] R 3 and R 6 The -CH2- groups contained in the hydrocarbon group represented are -O-, -CO-, -S-, -SO-, -NR 7 If it is replaced by - or -SO2-, the number of carbon atoms before replacement shall be the total number of carbon atoms in the hydrocarbon group. This number may be one or two or more. The -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7As mentioned above, the groups replaced by - or -CO- include hydroxyl group, carboxyl group, thiol group, amino group, oxy group, carbonyl group, thio group, sulfonyl group, peptide group, alkoxy group, alkylthio group, alkylsulfonyl group, alkylamino group, alkylpeptide group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkoxycarbonyloxy group, alkoxyalkoxy group, alkoxyalkyl group, hydroxyalkyl group, alkanediyloxy group, and alkanediyloxycarbonyl The -CH2- contained in groups such as alkanediylcarbonyl groups, alkanediylcarbonyloxy groups, alkanediyloxycarbonyloxy groups, alkanediylsulfonyl groups, alkanediylthio groups, alkanediylamino groups, alkanediylpeptide groups, cycloalkoxy groups, cycloalkylalkoxy groups, aromatic hydrocarbon groups-carbonyloxy groups, aromatic hydrocarbon groups-carbonyl groups, aromatic hydrocarbon groups-oxy groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, or combinations thereof, is -O-, -S-, -SO-, -SO2-, -NR 5 Examples include groups replaced by - or -CO- and groups formed by combining two or more of these groups. These replaced groups are similar to the groups exemplified herein, within the range of acceptable carbon numbers. Furthermore, the -CH2- contained in alicyclic hydrocarbon groups, aromatic hydrocarbon groups, or combinations thereof may be -O-, -S-, -SO2-, -SO-, -NR 7 Groups replaced by - or -CO- include those similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms.
[0036] R 3 and R 6 The substituents that the hydrocarbon group may have include halogen atoms, cyano groups, nitro groups, etc. 3 and R 6 However, in the case of a group that combines an alicyclic hydrocarbon group or an aromatic hydrocarbon group with a chain hydrocarbon group such as an alkyl group, the chain hydrocarbon group such as an alkyl group can be substantially substituted for the alicyclic hydrocarbon group or aromatic hydrocarbon group. 3and R 6 The -CH2- group contained in the alkyl group and other chain hydrocarbon groups is -O-, -CO-, -S-, -SO-, -NR 7 -By being replaced with -SO2-, R 3 and R 6 It can substantially have substituents such as hydroxyl groups, carboxyl groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, alkoxyalkoxy groups, thiol groups, alkylthio groups, alkylsulfonyl groups, amino groups, alkylamino groups, and alkylpeptide groups. Examples of halogen atoms include the same groups as those described above. R 3 and R 6 If R is a hydrocarbon group having a halogen atom, 3 and R 6 Examples of hydrocarbon groups having halogen atoms include chain hydrocarbon groups having halogen atoms such as haloalkyl groups, alicyclic hydrocarbon groups having halogen atoms, and aromatic hydrocarbon groups having halogen atoms. Alkyl groups having halogen atoms include C1-C12 haloalkyl groups, such as C1-C12 alkyl fluorides, C1-C12 alkyl chlorides, C1-C12 alkyl bromides, and C1-C12 alkyl iodides. Examples of haloalkyl groups include C1-C12 perfluoroalkyl groups (trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, and iodomethyl group. The number of carbon atoms in the haloalkyl group is preferably 1-9, more preferably 1-6, even more preferably 1-4, and even more preferably 1-3. The -CH2- group in the haloalkyl group may be replaced with -O- or -CO-, etc. Examples of such groups include haloalkoxy groups, haloalkoxycarbonyl groups, haloalkylcarbonyl groups, and haloalkylcarbonyloxy groups. Specifically, examples 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. For example, a group in which one or more hydrogen atoms of the above-executed groups are replaced with halogen atoms can be used. R 3 Examples include halogen atoms, C1-C12 alkyl groups, or C1-C10 haloalkyl groups (where the -CH2- contained in the alkyl group or haloalkyl group may be replaced with -O- or -CO-). Preferably, it is a halogen atom, a C1-C8 alkyl group, or a C1-C8 haloalkyl group (where the -CH2- contained in the alkyl group or haloalkyl group may be replaced with -O- or -CO-). More preferably, it is a halogen atom, a C1-C6 alkyl group (where the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), or a C1-C4 haloalkyl group. Even more preferably, it is an iodine atom, a fluorine atom, a hydroxyl group, a carboxyl group, a C1-C4 hydroxyalkyl group, a C1-C4 alkoxy group, or a C1-C4 fluorinated alkyl group. Even more preferably, it is a fluorine atom, an iodine atom, a hydroxyl group, a carboxyl group, a hydroxymethyl group, a methoxy group, or a C1-C3 perfluoroalkyl group. R 6Examples include halogen atoms, C1-C12 alkyl groups, or C1-C10 haloalkyl groups (where the -CH2- contained in the alkyl group or haloalkyl group may be replaced with -O- or -CO-). Preferably, it is a halogen atom, a C1-C8 alkyl group, or a C1-C8 haloalkyl group (where the -CH2- contained in the alkyl group or haloalkyl group may be replaced with -O- or -CO-). More preferably, it is a halogen atom, a C1-C6 alkyl group (where the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), or a C1-C4 haloalkyl group. Even more preferably, it is an iodine atom, a fluorine atom, a hydroxyl group, a carboxyl group, a C1-C4 hydroxyalkyl group, a C1-C4 alkoxy group, or a C1-C4 fluorinated alkyl group. Even more preferably, it is a fluorine atom, an iodine atom, a hydroxyl group, a carboxyl group, a hydroxymethyl group, a methoxy group, or a C1-C3 perfluoroalkyl group. m3 is preferably an integer between 0 and 3, more preferably an integer between 0 and 2, and even more preferably 0 or 1. m6 is preferably an integer between 0 and 3, more preferably an integer between 0 and 2, and even more preferably 0 or 1. -L 1B -R 5B Ar 1 The binding site to Ar is not particularly limited, but 1 If the group is derived from the naphthalene ring, L 2 However, Ar 1 If it is coupled to the 1st or 2nd position, then at least one -L 1B -R 5B However, Ar 1 It is preferable that the bond is located at position 3 through 8, and more preferably at position 3 through 6. -L 1A -R 5A Ar 2 The binding site to Ar is not particularly limited, but 2 If the group is derived from the naphthalene ring, L 3However, Ar 2 If it is coupled to the 1st or 2nd position, then at least one -L 1A -R 5A However, Ar 2 It is preferable that the bond is located at position 3 through 8, and more preferably at position 3 through 6. R 3 Ar 1 The binding site to Ar is not particularly limited, but 1 If the group is derived from the naphthalene ring, L 2 However, Ar 1 If it is coupled at position 1 or 2, then at least one R 3 However, Ar 1 It is preferable that it is bonded at the 3rd, 4th, 5th, or 7th position. R 6 Ar 2 The binding site to Ar is not particularly limited, but 2 If the group is derived from the naphthalene ring, L 3 However, Ar 2 If it is coupled at position 1 or 2, then at least one R 6 However, Ar 2 It is preferable that it is bonded at the 3rd, 4th, 5th, or 7th position.
[0037] Compound (I) includes compounds represented by the following formula. TIFF2026088086000027.tif236159
[0038] TIFF2026088086000028.tif250155
[0039] TIFF2026088086000029.tif250160
[0040] TIFF2026088086000030.tif243161
[0041] TIFF2026088086000031.tif252156
[0042] In the resist composition of the present invention, the content of compound (I) is 0.1% by mass or more, preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, even more preferably 10% by mass or more, and even more preferably 20% by mass or more, relative to the solid content of the resist composition. Also, it is 90% by mass or less, preferably 85% by mass or less, more preferably 80% by mass or less, and even more preferably 75% by mass or less. For example, it is 0.1 to 90% by mass, preferably 1 to 85% by mass, more preferably 5 to 80% by mass, and even more preferably 10 to 80% by mass.
[0043] <Method for producing compound (I)> Compound (I) can be produced, for example, by reacting a compound represented by formula (Ia) with a compound represented by formula (I-b1) or a compound represented by formula (I-b2) in a solvent in the presence of a catalyst. TIFF2026088086000032.tif65166(In the formula, symbols other than those listed below have the same meaning as above. X represents -O-*, -CO-O-*, -NR 7 -* or -CO-NR 7 - represents *. * represents the bonding site with a hydrogen atom. L 1A’ and L 1B’ L 1A and L 1B (This represents the base obtained by removing -X- from the original.) Examples of catalysts include potassium carbonate, potassium iodide, pyridine, diethylaminopyridine, triethylamine, and carbonyldiimidazole. Examples of solvents include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is typically between 15°C and 80°C, and the reaction time is typically between 0.5 and 24 hours.
[0044] Compounds represented by formula (Ia) include, for example, the compounds shown below, which are readily available on the market and can also be easily manufactured by known methods. TIFF2026088086000033.tif248152
[0045] TIFF2026088086000034.tif82135
[0046] Compounds represented by formula (I-b1) include, for example, the compounds shown below, which are readily available on the market and can also be easily manufactured by known methods. Compounds represented by formula (I-b2) include, for example, the compounds shown below, which are readily available on the market and can also be readily manufactured by known methods. TIFF2026088086000036.tif16158
[0047] Compound (I) can be produced, for example, by reacting a compound represented by formula (Ic) with a compound represented by formula (Id) in a solvent in the presence of a catalyst. TIFF2026088086000037.tif92157(In the formula, symbols other than those listed below have the same meaning as above. mn1 represents 0 or 1. X' represents -O- or -NR) 7 - (This represents...) Examples of catalysts include potassium carbonate, potassium iodide, pyridine, diethylaminopyridine, triethylamine, and carbonyldiimidazole. Examples of solvents include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is typically between 15°C and 80°C, and the reaction time is typically between 0.5 and 24 hours.
[0048] Compounds represented by formula (Ic) include, for example, the compounds shown below, which are readily available on the market and can also be easily manufactured by known methods. Compounds represented by formula (Id) TIFF2026088086000038.tif67151 include, for example, the compounds shown below, which are readily available on the market and can also be readily manufactured by known methods. TIFF2026088086000039.tif30141
[0049] <Acid Generator (B)> In the resist composition of the present invention, if an acid generator (B) is included, the total content of the acid generator (B) is preferably 0.1% by mass or more and 99.9% by mass or less, more preferably 1% by mass or more and 45% by mass or less, even more preferably 1% by mass or more and 40% by mass or less, and even more preferably 3% by mass or more and 40% by mass or less, based on the solid content of the resist composition. If the resist composition of the present invention includes the resin described later, the total content of the acid generator (B) is preferably 1 part by mass or more, more preferably 3 parts by mass or more, preferably 55 parts by mass or less, more preferably 50 parts by mass or less, and even more preferably 45 parts by mass or less, based on 100 parts by mass of the resin.
[0050] 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 ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxiimide, sulfonyloxyketone, diazonaphthoquinone 4-sulfonate) and sulfones (e.g., disulfone, ketosulfone, sulfonyldiazomethane). Typical ionic acid generators include onium salts containing onium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts, iodonium salts). Examples of onium salt anions include sulfonic acid anions, sulfonylimide anions, sulfonylmethide anions, and carboxylic acid anions. Furthermore, the acid generator (B) may be part of the structural units that constitute the resin contained in the resist composition of the present invention, as shown in the structural unit (a7) described later.
[0051] As the acid generator (B), compounds that generate acid by radiation as described in Japanese Patent Publication Nos. 63-26653, 55-164824, 62-69263, 63-146038, 63-163452, 62-153853, 63-146029, U.S. Patent Nos. 3,779,778 and 3,849,137, German Patent No. 3914407, European Patent No. 126,712, etc., can be used. Compounds manufactured by known methods may also be used. The acid generator (B) may be used alone or in combination of two or more types. The acid generator (B) may be an acid generator having an acid-unstable group. For example, the compound or resin that acts as the acid generator may contain a substructure that constitutes an acid-unstable group, and it is preferable that the acid-unstable group contains group (1) or group (2) described later. If the resist composition of the present invention contains a compound having an acid-unstable group, it does not need to contain a resin containing a structural unit having an acid-unstable group.
[0052] Preferred forms 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)"). TIFF2026088086000040.tif1392[In formula (B1), all signs have the same meaning as described above.]
[0053] L b1 As for (nb1+1) valent hydrocarbon groups, one nb hydrogen atom is removed from a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, a monovalent aromatic hydrocarbon group, and a monovalent group formed by combining two or more of these groups, resulting in 1 or more L b2 A group that bonds with the hydrocarbon group is an example. The number of carbon atoms in the hydrocarbon group is 1 to 48, preferably 1 to 42, more preferably 1 to 36, even more preferably 1 to 30, even more preferably 1 to 24, and even more preferably 1 to 18. Examples of chain-like hydrocarbon groups include alkyl groups or alkenyl groups from which one nb hydrogen atom has been removed. Alkyl groups may be linear or branched, and specifically include methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, and heptadecyl groups. Examples of alkenyl groups include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 36, more preferably 1 to 24, even more preferably 1 to 20, even more preferably 1 to 18, even more preferably 1 to 12, and even more preferably 1 to 10. Examples of alicyclic hydrocarbon groups include groups obtained by removing one nb hydrogen atom from a monocyclic or polycyclic cycloalkyl group. Examples of monocyclic cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Examples of polycyclic cycloalkyl groups include cycloalkyl groups having a cross-linking structure, cycloalkyl groups formed by the condensation of two or more rings, or cycloalkyl groups formed by the spirolinking of two rings. Examples of cycloalkyl groups having a cross-linking structure include norbornyl groups and adamantyl groups. Examples of cycloalkyl groups formed by the condensation of two or more rings include bicyclo[4.4.0]decanyl groups and steroid groups (steroid skeletons). Examples of cycloalkyl groups formed by the spirolinking of two rings include spirocyclic cycloalkyl groups in which one or more cycloalkyl groups selected from the group consisting of cyclopentyl groups, cyclohexyl groups, norbornyl groups, and adamantyl groups are spirolinked to a cycloalkyl group having 5 to 8 carbon atoms. Furthermore, a double bond may be formed between two carbon atoms in the alicyclic hydrocarbon group. More specifically, examples include alicyclic hydrocarbon groups represented by the following formula. TIFF2026088086000041.tif41165 When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 20, even more preferably 3 to 18, even more preferably 3 to 12, even more preferably 3 to 10, and even more preferably 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 6 to 24, more preferably 6 to 20, even more preferably 6 to 18, even more preferably 6 to 12, and even more preferably 7 to 12. Aromatic hydrocarbon groups include those obtained by removing one hydrogen atom from the nb side of an aryl group. Examples of aryl groups include phenyl, naphthyl, anthryl, biphenyl, and fluorenyl groups. More specifically, aromatic hydrocarbon groups represented by the following formulas are examples. TIFF2026088086000042.tif1286 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. L b1 If the -CH2- contained in the hydrocarbon group is replaced by -O-, -CO-, -S-, -SO-, or -SO2-, the number of carbon atoms before the replacement shall be considered the number of carbon atoms in the hydrocarbon group. L b1Among the hydrocarbon groups, groups in which the -CH2- contained in the chain hydrocarbon group is replaced with -O-, -CO-, -S-, -SO-, or -SO2- include hydroxyl groups, carboxyl groups, carbonyl groups, oxy groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, alkanediyloxy groups, alkanediyloxycarbonyl groups, alkanediylcarbonyloxy groups, and the like. These replaced groups are similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. L b1 Among the hydrocarbon groups, groups in which the -CH2- contained in alicyclic hydrocarbon groups, aromatic hydrocarbon groups, or combinations thereof is replaced with -O-, -CO-, -S-, -SO-, or -SO2- include groups containing structures such as cyclic ethers, cyclic ketones, cyclic esters (lactones), cyclic thioethers, cyclic acetals, and cyclic sulfonic acid esters (sultones), as well as groups derived from furan rings, thiophene rings, etc. These replaced groups are similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. Groups combining two or more types of groups, such as a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, include groups combining the above-mentioned chain hydrocarbon group and the above-mentioned alicyclic hydrocarbon group, groups combining the above-mentioned chain hydrocarbon group and the above-mentioned aromatic hydrocarbon group, groups combining the above-mentioned alicyclic hydrocarbon group and the above-mentioned aromatic hydrocarbon group, and groups combining the above-mentioned chain hydrocarbon group, the above-mentioned alicyclic hydrocarbon group, and the above-mentioned aromatic hydrocarbon group. Groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group may also be fused rings. L b2 Examples of divalent hydrocarbon groups include divalent chain hydrocarbon groups, divalent alicyclic hydrocarbon groups, divalent aromatic hydrocarbon groups, and groups formed by combining two or more of these groups. By removing one hydrogen atom from a monovalent hydrocarbon group, Y b1 Examples of groups that bond with it include: L b2The divalent chain hydrocarbon group, divalent alicyclic hydrocarbon group, divalent aromatic hydrocarbon group, and divalent groups formed by combining two or more of these groups are each L, within the limits permitted by the upper limit of the number of carbon atoms. b1 Examples include monovalent chain hydrocarbon groups, monovalent alicyclic hydrocarbon groups, monovalent aromatic hydrocarbon groups, and monovalent groups obtained by removing one hydrogen atom from a combination of two or more of these monovalent groups. L b1 and L b2 The hydrocarbon group may have substituents such as halogen atoms, cyano groups, and nitro groups. Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. L b1 and L b2 However, if the group is a combination of an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group, the chain hydrocarbon group may be substantially considered as a substituent of the alicyclic hydrocarbon group or aromatic hydrocarbon group. b1 and L b2 The -CH2- in the chain hydrocarbon group contained in the hydrocarbon group is replaced by -O-, -CO-, -S-, -SO-, or -SO2-, L b1 and L b2 The hydrocarbon group may substantially have substituents such as a hydroxyl group, carboxyl group, carbonyl group, oxycarbonyl group, carbonyloxy group, alkoxy group, alkylcarbonyl group, alkoxycarbonyl group, alkylcarbonyloxy group, thiol group, alkylthio group, and alkylsulfonyl group. Y b1 Examples of cyclic hydrocarbon groups include alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups that combine alicyclic hydrocarbon groups and aromatic hydrocarbon groups. Y b1 The alicyclic hydrocarbon group and aromatic hydrocarbon group are, respectively, L b1 Examples include the same alicyclic hydrocarbon groups and aromatic hydrocarbon groups as exemplified above, and if they do not have substituents, they may be monovalent alicyclic hydrocarbon groups and aromatic hydrocarbon groups. Y b1Examples of substituents that the methyl group and cyclic hydrocarbon group may have include halogen atoms, cyano groups, nitro groups, or C1-C18 hydrocarbon groups that may have halogen atoms, cyano groups, or nitro groups (the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-). b1 The number of carbon atoms in the methyl group and the cyclic hydrocarbon group that may have is Y b1 The number of carbon atoms in the methyl group and cyclic hydrocarbon group is not included. Y b1 The methyl group and cyclic hydrocarbon group may have as substituents, and hydrocarbon groups having 1 to 18 carbon atoms include chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining these groups. Examples of chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining two or more of these groups include, within the limits permitted by the upper limit of carbon atoms, L b1 Examples include the chain-like hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining two or more of these groups, as exemplified above. Also, Y b1 Examples of groups in which the methyl group and cyclic hydrocarbon group may have as substituents, and in which the -CH2- in a hydrocarbon group having 1 to 18 carbon atoms is replaced with -O-, -S-, -CO-, -SO-, or -SO2-, are given within the limits permitted by the upper limit of carbon atoms. b1 Groups in which the -CH2- contained in the hydrocarbon group is replaced with -O-, -S-, -CO-, -SO-, or -SO2- are similar to the groups exemplified above. Also, Y b1 The methyl group and cyclic hydrocarbon group may have as substituents a hydrocarbon group having 1 to 18 carbon atoms, which may constitute a protecting group or a leaving group (acid-unstable group or base-unstable group) commonly used in the field. The anion of the salt represented by formula (B1) is preferably the anion represented by the following formula (B1-A1) (hereinafter sometimes referred to as "anion (B1-A1)") or the anion represented by formula (B1-A2) (hereinafter sometimes referred to as "anion (B1-A2)"). TIFF2026088086000043.tif30126[In formula (B1-A1), L b2 and Y b1 This has the same meaning as formula (B1). Q b1 Q b2 Q b3 and Q b4 Each of these 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 between 0 and 6. When z1 is 2 or greater, the bases within the parentheses may be the same or different. X 1 -O-CO-, -CO-O-, -O-CO-O-, or -O-. L b3 represents a (nb2+1) valent hydrocarbon group having 1 to 24 carbon atoms, which may have single bonds or substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-. nb2 represents an integer between 1 and 3. When nb2 is 2 or greater, the bases within the parentheses may be the same or different. Q b1 Q b2 Q b3 and Q b4 Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. Q b1 Q b2 Q b3 and Q b4 Examples of perfluoroalkyl groups include trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorosec-butyl, perfluorotert-butyl, perfluoropentyl, and perfluorohexyl groups. Q b1 and Q b2 Q b1 and Q b2Preferably, at least one of them 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 Each of these is preferably independently a hydrogen atom, a fluorine atom, or a perfluoroalkyl group having 1 to 3 carbon atoms, Q b3 Q is preferably a hydrogen atom, a fluorine atom, or a perfluoroalkyl group having 1 to 3 carbon atoms. b4 It is preferable that this is a hydrogen atom or a fluorine atom. z1 is preferably an integer between 0 and 3, and more preferably 0, 1, or 2. X 1 It is preferable that it be -O-CO- or -CO-O-.
[0054] L b3 As for the hydrocarbon group in this, within the limits permitted by the upper limit of the number of carbon atoms, L of formula (B1) b1 The same hydrocarbon groups as in the example above can be cited. L b3It is preferably a single bond, a chain hydrocarbon group having 1 to 12 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), a alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have substituents (the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO- or -SO2-), an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have substituents (the -CH2- contained in the aromatic hydrocarbon group may be replaced with -O- or -S-), or a group formed by combining two or more of these groups, and more preferably a single bond, a chain hydrocarbon group having 1 to 6 carbon atoms, or a group represented by the following formula (Lb3-1). Furthermore, when -CH2- contained in a chain hydrocarbon group is replaced with -O- or -CO-, it is preferable that the number of -CH2- contained in the chain hydrocarbon group that is replaced with -O- or -CO- is 1 to 4, and it is preferable that one -CH2-CH2- contained in the chain hydrocarbon group is replaced with -O-CO- or -CO-O-, or that one -CH2-CH2-CH2- contained in the chain hydrocarbon group is replaced with -O-CO-O-. TIFF2026088086000044.tif1580[In formula (Lb3-1), nb2 has the same meaning as the expression (B1-A1). L b31 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms, and the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and the chain hydrocarbon group may have substituents. 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 the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO- or -SO2-, and the -CH2- contained in the aromatic hydrocarbon group may be replaced with -O- or -S-, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have substituents. * and ** represent bonding sites, where * is X 1 This represents the connection point with [the other element]. In formula (Lb3-1), L b31The chain-like hydrocarbon group is L as long as the upper limit of the number of carbon atoms allows. b1 Examples of similar groups to the chain-like hydrocarbon groups exemplified above include those mentioned earlier. In formula (Lb3-1), W b3 The alicyclic hydrocarbon group and aromatic hydrocarbon group are L as long as the upper limit of the number of carbon atoms allows. b1 Examples of similar groups to the alicyclic hydrocarbon groups and aromatic hydrocarbon groups exemplified above include the alicyclic hydrocarbon groups and aromatic hydrocarbon groups. In formula (Lb3-1), L b31 The chain-like hydrocarbon group may have substituents and W b3 The substituents that the alicyclic hydrocarbon group and aromatic hydrocarbon group may have are L b1 Examples of substituents that the hydrocarbon group may have include groups similar to those exemplified above. L b31 Preferably, the component is a single bond or an alkanediyl group having 1 to 6 carbon atoms (the -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-). W b3 Examples of alicyclic hydrocarbon groups and aromatic hydrocarbon groups include the following: In the alicyclic hydrocarbon groups and aromatic hydrocarbon groups shown below, * and ** represent bonding sites, and * is X 1 or L b31 This represents the bonding site with , where ** represents a hydrogen atom, substituent, or L b2 This represents the bonding site with L, and at least one ** is L b2 This represents the bonding site with . Furthermore, in the alicyclic hydrocarbon group shown below, the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-. When the -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), carbonate ester ring, sulfonic acid ester ring (sultone), or acetal ring is formed. In TIFF2026088086000045.tif37164 (B1-A1), L b2The carbon atoms are preferably single bonds or chain hydrocarbon groups having 1 to 12 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), and are single bonds, -O-, -O-CO-, -CO-O-, -O-CO-O- or *-L b21 -X 2 -L b22 -**(L b21 and L b22 Either one represents a chain hydrocarbon group having 1 to 6 carbon atoms, and the other represents a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms. 2 represents -O-, -CO-O-, -O-CO-, or -O-CO-O-. * and ** represent bonding sites, and ** is Y b1 This represents the bonding site with L. b21 , X 2 and L b22 It is more preferable that the total number of carbon atoms is 12 or less. In equation (B1-A1), Y b1 It is preferably a cyclic hydrocarbon group having 3 to 20 carbon atoms that may have substituents (the -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 that may have substituents (the -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 that may have substituents, and even more preferably an alicyclic hydrocarbon group having 3 to 16 carbon atoms that may have substituents (the -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 10 carbon atoms that may have substituents. Specifically, it is more preferably a group represented by the following formulas (Y1) to (Y36). In formulas (Y1) to (Y36), R Yb is a hydrogen atom or Y b1 Among the substituents that the cyclic hydrocarbon group may have, represent an alkyl group having 1 to 4 carbon atoms, R Yc is a hydrogen atom or Y b1 This represents substituents that the cyclic hydrocarbon group may have, and * represents L b2This represents the bonding site. The alicyclic hydrocarbon group and aromatic hydrocarbon group represented by the following formula may have other substituents, although they are not specifically shown in the following formula. TIFF2026088086000046.tif83160
[0055] The anion represented by formula (B1-A1) is preferably the anion represented by formulas (B1-A1-1) to (B1-A1-85) [hereinafter, depending on the formula number, it may be referred to as "anion (B1-A1-1)", etc.], and more preferably the anion represented by any of formulas (B1-A1-1) to (B1-A1-4), formula (B1-A1-9), formula (B1-A1-10), formula (B1-A1-24) to (B1-A1-33), formula (B1-A1-36) to (B1-A1-40), or formula (B1-A1-47) to (B1-A1-85). TIFF2026088086000047.tif202160
[0056] TIFF2026088086000048.tif249149
[0057] TIFF2026088086000049.tif253158
[0058] Here R i2 ~R i7 These are, independently of each other, for example, an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group. i8 For example, this is 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 a combination thereof, more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. A41 This is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Q b1 and Q b2 This expresses the same meaning as above. An example of anion represented by formula (B1-A1) is the anion described in Japanese Patent Publication No. 2010-204646.
[0059] Preferred anions represented by formula (B1-A1) include those represented by formulas (B1a-1) to (B1a-82), respectively. Among these, anions represented by any of the following are preferred: formulas (B1a-1) to (B1a-4), formulas (B1a-7) to (B1a-11), formulas (B1a-14) to (B1a-30), and formulas (B1a-35) to (B1a-70). TIFF2026088086000050.tif185163
[0060] TIFF2026088086000051.tif252162
[0061] TIFF2026088086000052.tif133165
[0062] The anion represented by equation (B1-A2) is expressed by the following equation: TIFF2026088086000053.tif23100[In formula (B1-A2), L b2 and Y b1 This has the same meaning as formula (B1). R b1 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and the -CH2- contained in the alkyl group may be replaced with -O- or -CO-. nb4 represents an integer between 1 and 5. When nb4 is 2 or greater, the bases within the parentheses may be the same or different. nb3 represents an integer between 0 and 4. When nb3 is 2 or greater, multiple R b1 They may be identical or different from one another. However, the condition 1 ≤ nb4 + nb3 ≤ 5 must be satisfied.
[0063] In equation (B1-A2), L b2 Examples of hydrocarbon groups and Y b1 Examples of cyclic hydrocarbon groups include L in formula (B1), to the extent permitted by the upper limit of the number of carbon atoms. b2 Examples of hydrocarbon groups and Y b1Examples of cyclic hydrocarbon groups are the same as those shown. b2 The hydrocarbon group, Y b1 The substituents that the methyl group and cyclic hydrocarbon group may have are also the L of formula (B1) b2 The hydrocarbon group, Y b1 Examples of substituents that the methyl group and cyclic hydrocarbon group may have are the same as those mentioned above. These hydrocarbon groups, methyl groups, and cyclic hydrocarbon groups may have one or more substituents. L b2 Preferably, is a chain-like hydrocarbon group having 1 to 12 carbon atoms (the -CH2- contained in the chain-like hydrocarbon group may be replaced with -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 the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-. - This represents the bonding site with the benzene ring to which it is bonded. b41 The carbon group is preferably a single bond or a chain-like hydrocarbon group having 1 to 3 carbon atoms, and more preferably *-CO-O-. Y b1 It is preferably a cyclic hydrocarbon group having 3 to 20 carbon atoms that may have substituents (the -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 that may have substituents (the -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 that may have substituents, and Y of formula (B1-A1) b1 or L b1 It is even more preferable that the group is an alicyclic hydrocarbon group or an aromatic hydrocarbon group as exemplified above. Specifically, it is preferably a group represented by formulas (Y1) to (Y36) described above, and more preferably a group represented by formulas (Y1) to (Y19) described above. Y b1The substituents that the cyclic hydrocarbon group may have are preferably halogen atoms or C1-C6 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-), more preferably fluorine atoms, iodine atoms, or C1-C4 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-), even more preferably fluorine atoms, iodine atoms, hydroxyl groups, C1-C3 alkoxy groups, or C1-C4 alkyl groups, and even more preferably fluorine atoms, iodine atoms, hydroxyl groups, or C1-C4 alkyl groups. b1 The substituents may be protecting groups or leaving groups (acid-unstable or base-unstable groups) commonly used in the field.
[0064] In formula (B1-A2), nb4 is preferably an integer from 1 to 4, more preferably an integer from 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 binding position is SO3 - The following structure is preferable, where the benzene ring is meta-substituted relative to the bonded position. TIFF2026088086000054.tif25104[In the above formula, L b2 , Y b1 , R b1 nb3 has the same meaning as formula (B1-A2). In formula (B1-A2), if nb4 is 2 or more, multiple L b2 and Y b1 It is preferable that these are the same group.
[0065] R b1 Examples of alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, and hexyl groups. The number of carbon atoms in the alkyl group is preferably 1 to 4, and more preferably 1 to 3. Rb1 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. Groups in which the -CH2- group in an alkyl group is replaced with -O- or -CO- include hydroxyl groups, carboxyl groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, oxy groups, and carbonyl groups. These replaced groups are similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. R b1 Each of these is preferably independently a halogen atom or a C1-C4 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), more preferably a fluorine atom, an iodine atom, or a C1-C3 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a hydroxyl group, a methoxy group, or a methyl group. nb3 is preferably an integer between 0 and 3, and more preferably an integer between 0 and 2. In one embodiment, nb3 is preferably 0. In another embodiment, nb3 is preferably 1 or 2. When nb3 is 1, R b1 It is preferable that R is a halogen atom, b1 It is more preferable that nb3 is a fluorine atom or an iodine atom. When nb3 is 2, R b1 Preferably, one of them is a halogen atom, and the other is a halogen atom or an alkyl group having 1 to 4 carbon atoms, R b1 It is more preferable that one of the atoms is a fluorine atom or an iodine atom, and the other atom is a fluorine atom, an iodine atom, or an alkyl group having 1 to 3 carbon atoms.
[0066] Examples of anions represented by formula (B1-A2) include the following anions. Among these, anions represented by formulas (B2a-1) to (B2a-32) are preferred, and anions represented by formulas (B2a-1) to (B2a-11) and (B2a-16) to (B2a-20) are more preferred. The following anions are some Rb1 The figure is omitted and may include substituents that are not shown. TIFF2026088086000055.tif102153
[0067] TIFF2026088086000056.tif77163
[0068] Examples of acid generators (B2) include salts represented by the following formula. TIFF2026088086000057.tif1292[In formula (B2), A 1 represents a nitrogen atom or a carbon atom. L b2’ represents a divalent hydrocarbon group having 1 to 24 carbon atoms, which may have single bonds or substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-. Y b1’ represents a methyl group which may have substituents or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO- or -SO2-. nb5 represents an integer of 2 or 3. 1 If it is a nitrogen atom, then nb5 is 2, and A 1 If is a carbon atom, then nb5 is 3. The groups in parentheses may be the same or different from each other, and two groups in parentheses combine to form A 1 A ring containing the element may be formed. Z2 + This represents an organic cation.
[0069] In equation (B2), L b2’ and Y b1’ An example of this is L in formula (B1-A1). b2 and Y b1 Similar bases can be cited. L b2’ This is a single bond, *-L b23 -, *-L b23 -X 2 - or *-Lb23 -X 2 -W 2 -X 3 -(L b23 X represents a chain-like hydrocarbon group having 1 to 6 carbon atoms, which may contain a fluorine atom. 2 and X 3 These independently represent -O-, -CO-O-, -O-CO-, -O-CO-O-, or -O-. 2 represents an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-. * represents the bonding site with SO2. ) is preferable. Y b1’ It is preferably a methyl group having a fluorine atom or a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have substituents (the -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 substituents (the -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 substituents. Specifically, it is more preferably a trifluoromethyl group or a group represented by formulas (Y1) to (Y36) as exemplified in formula (B1-A1). In the salt anion represented by formula (B2), two -SO2-L b2’ -Y b1’ together become A 1 When forming a ring containing this, for example, an anion represented by formula (B2') can be cited. TIFF2026088086000058.tif21112[In formula (B2'), A 1 , Y b1’ , L b2’ And nb5 has the same meaning as formula (B2). W b4 This represents a disulfonylimide ring or disulfonylmethide ring having 2 to 12 carbon atoms, which may contain a fluorine atom. W b4The disulfonylimide ring or disulfonylmethide ring preferably has 3 to 12 carbon atoms, more preferably 3 to 6 carbon atoms, and it is preferable that the hydrogen atoms of the methylene group contained in the ring are replaced with fluorine atoms.
[0070] The following are examples of anions in the salt represented by formula (B2). Among these, the anions represented by formulas (B3a-1), (B3a-2), (B3a-12) to (B3a-14) are preferred. TIFF2026088086000059.tif132168
[0071] Another form of compound (B) is the salt represented by formula (B4) (hereinafter sometimes referred to as "salt (B4)" or "acid generator (B4)"). TIFF2026088086000060.tif29119[In formula (B4), L b14 and L b15 Each of these independently represents a divalent hydrocarbon group having 1 to 72 carbon atoms, which may have single bonds or substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, or -SO2-. Ar B4 and Ar B5 Each of these independently represents an aromatic hydrocarbon group having 6 to 24 carbon atoms, which may have substituents, and Ar B4 and Ar B5 The substituents may bond to form a ring. R B4 and R B5 Each of these independently represents a hydrocarbon group having 1 to 18 carbon atoms, which may have a halogen atom or substituents, and the -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S-, -SO-, or -SO2-. mB4 represents an integer between 0 and 4, and when mB4 is 2 or greater, multiple R B4 They may be identical or different from one another. mB5 represents an integer between 0 and 4, and when mB5 is 2 or greater, multiple R B5They may be identical or different from one another. Z4 + and Z5 + Each of these independently represents an organic cation.
[0072] In equation (B4), L b14 and L b15 An example of this is L in formula (B1). b1 Or L in formula (B1-A1) b3 The same type of group can be cited as an example. Ar B4 and Ar B5 Examples of aromatic hydrocarbon groups include phenylene groups, naphthylene groups, anthrylene groups, biphenylene groups, and phenanthrylene groups. The bonding site can be at any position. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10. Ar B4 and Ar B5 The substituents that the aromatic hydrocarbon group may have include halogen atoms, hydroxyl groups, cyano groups, carboxyl groups, C1-C12 alkyl groups, C1-C6 fluorinated alkyl groups, C1-C12 alkoxy groups, and groups formed by combining two or more of these groups. These substituents are described in R B4 and R B5 Examples similar to those exemplified earlier can be given. Among them, Ar B4 and Ar B5 The group is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, which may have substituents; more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, which may have a halogen atom, a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, or an alkyl fluoride group having 1 to 6 carbon atoms; even more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, which may have a fluorine atom, an iodine atom, an alkyl group having 1 to 6 carbon atoms, or an alkyl fluoride group having 1 to 3 carbon atoms; and even more preferably a phenylene group or a naphthylene group. Ar B4 and Ar B5 If is a phenylene group which may have substituents, the bond position of the fluorene ring is L b14 and Lb15 The bonding position may be ortho, meta, or para, but it is preferably meta or para, and more preferably para.
[0073] R B4 and R B5 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. R B4 and R B5 Examples of hydrocarbon groups having 1 to 18 carbon atoms include chain-type hydrocarbon groups such as alkyl groups and alkanediyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. Examples of alkyl groups include linear or branched alkyl groups, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, and dodecyl group. Alkanediyl groups include linear or branched alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and Examples of branched alkanediyl groups include ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 12, more preferably 1 to 9, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. The alicyclic hydrocarbon group may be monocyclic or polycyclic, and examples similar to those exemplified herein are available, within the limits permitted by the upper limit of the number of carbon atoms. Specifically, 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 cycloalkyl groups spiro-bonded to norbornyl or adamantyl 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. Examples of aromatic hydrocarbon groups include phenyl groups, naphthyl groups, biphenyl groups, anthryl groups, phenanthryl groups, and binaphthyl groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10.
[0074] Groups formed by combining two or more groups from among 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-*, the -CH2- contained in the alkanediyl group and the alkyl group may be replaced with -O-, -CO-, -S-, -SO- or -SO2-), and groups formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group-alkanediyl group). Examples include diyl group-*, alkyl group-alicyclic hydrocarbon group-*, alkyl group-alicyclic hydrocarbon group-alkanediyl group-*, the -CH2- contained in the alicyclic hydrocarbon group, the alkanediyl group and the alkyl group may be replaced with -O-, -CO-, -S-, -SO- or -SO2-), and groups combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, aromatic hydrocarbon group-alicyclic hydrocarbon group-*, alicyclic hydrocarbon group-aromatic hydrocarbon group-*, the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S-, -SO- or -SO2-). * indicates a bonding site. Examples of aromatic hydrocarbon groups - alkanediyl groups -* include aralkyl groups such as benzyl and phenethyl groups. Examples of alkyl-aromatic hydrocarbon groups-* include tolyl groups, xylyl groups, and cumenyl groups. Examples of alicyclic hydrocarbon groups - alkanediyl groups -* include cyclohexylmethyl group, cyclohexylethyl group, 1-(adamantan-1-yl)methyl group, 1-(adamantan-1-yl)-1-methylethyl group, and other cycloalkylalkyl groups. Examples of alkyl-alicyclic hydrocarbon groups include methylcyclohexyl group, dimethylcyclohexyl group, and cycloalkyl groups having alkyl groups such as 2-alkyladamantan-2-yl group. Examples of aromatic hydrocarbon groups - alicyclic hydrocarbon groups -* include the phenylcyclohexyl group. Examples of alicyclic hydrocarbon groups - aromatic hydrocarbon groups -* include the cyclohexylphenyl group. Furthermore, in the combinations, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain-like hydrocarbon groups may be combined. Also, any of these groups may be bonded to a benzene ring or the like.
[0075] R B4 and R B5 If the -CH2- contained in the hydrocarbon group represented by is replaced by -O-, -CO-, -S-, -SO-, or -SO2-, the number of carbon atoms before replacement shall be the total number of carbon atoms in the hydrocarbon group. This number may be one or two or more. As mentioned above, examples of groups in which the -CH2- contained in a hydrocarbon group is replaced with -O-, -S-, -SO-, -SO2-, or -CO- include hydroxyl groups, thiol groups, carboxyl groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkylthio groups, alkylsulfonyl groups, oxy groups, carbonyl groups, thio groups, sulfonyl groups, alkanediyloxy groups, alkanediyloxycarbonyl groups, alkanediylcarbonyl groups, alkanediylcarbonyloxy groups, alkanediylthio groups, alkanediylsulfonyl groups, cycloalkoxy groups, cycloalkylalkoxy groups, alkoxycarbonyloxy 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. These replaced groups are similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. Furthermore, groups in which the -CH2- contained in alicyclic hydrocarbon groups and groups formed by combining alicyclic hydrocarbon groups and aromatic hydrocarbon groups is replaced with -O-, -S-, -SO-, -SO2-, or -CO- include the same groups as those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms.
[0076] R B4 and R B5 The substituents that the hydrocarbon group may have include halogen atoms, cyano groups, nitro groups, and the like. Examples of halogen atoms include the same groups as those described above. The hydrocarbon group may have one substituent or more substituents. R B4 and R B5 However, if it is a hydrocarbon group having a halogen atom, R B4 and R B5 Examples of hydrocarbon groups having halogen atoms include chain hydrocarbon groups having halogen atoms such as haloalkyl groups, alicyclic hydrocarbon groups having halogen atoms, and aromatic hydrocarbon groups having halogen atoms. A haloalkyl group refers to an alkyl group having a halogen atom, and examples include C1-C12 alkyl fluorides, C1-C12 alkyl chlorides, C1-C12 alkyl bromides, and C1-C12 alkyl iodides. Examples of haloalkyl groups include C1-C12 perfluoroalkyl groups (trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, and iodomethyl group. The number of carbon atoms in the haloalkyl group is preferably 1-9, more preferably 1-6, even more preferably 1-4, and even more preferably 1-3. The -CH2- group in the haloalkyl group may be replaced with -O- or -CO-, etc. Examples of such groups include haloalkoxy groups, haloalkoxycarbonyl groups, haloalkylcarbonyl groups, and haloalkylcarbonyloxy groups. Specifically, examples 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. For example, a group in which one or more hydrogen atoms of the above-executed groups are replaced with halogen atoms can be used. mB4 is preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, and even more preferably 0 or 1. mB5 is preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, and even more preferably 0 or 1. R B4 and R B5 Each of these is preferably independently a halogen atom, a C1-C6 haloalkyl group, or a C1-C6 alkyl group (the -CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), more preferably a fluorine atom, an iodine atom, a C1-C6 haloalkyl group, or a C1-C6 alkyl group (the -CH2- contained in the haloalkyl group and the alkyl group may be replaced with -O- or -CO-), and more preferably a fluorine atom, an iodine atom, a C1-C4 haloalkyl group, or a C1-C4 alkyl group (the alkyl group may contain The -CH2- may be replaced with -O- or -CO-. It is more preferably a fluorine atom, an iodine atom, a hydroxyl group, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C3 alkoxy group, it is even more preferably a fluorine atom, an iodine atom, a hydroxyl group, a C1-C4 alkyl group, a C1-C4 perfluoroalkyl group or a C1-C3 alkoxy group, and it is even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a methoxy group, an ethoxy group or a hydroxyl group.
[0077] The following are examples of anions in the salt represented by formula (B4). Among these, the anions represented by formulas (B4a-1) to (B4a-4) and (B4a-11) to (B4a-14) are preferred. TIFF2026088086000061.tif120163
[0078] Furthermore, in another form of the acid generator (B), a salt obtained by replacing the anion in the salt represented by formula (B1) with a carboxylate anion is also suitably used as the acid generator (B). Examples of carboxylic acid anions include the following: TIFF2026088086000062.tif40154
[0079] Z1 + Z2 + Z4 + and Z5 + Examples of organic cations 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 aryl sulfonium cations or aryl iodonium cations are more preferred. Specifically, examples include cations represented by any of formulas (b2-1) to (b2-5) (hereinafter, depending on the formula number, they may be referred to as "cation (b2-1)," etc.). TIFF2026088086000063.tif84164[Formula (b2-1) to (b2-5), R b4 ~R b6 Each of these independently represents 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. The hydrogen atoms in the chain hydrocarbon group may be substituted with a hydroxyl group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. The hydrogen atoms in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a glycidyloxy group. The hydrogen atoms in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxyl group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkyl fluoride group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b4 and R b5 These atoms may bond with each other and form a ring together with the sulfur atom to which they are bonded, and the -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R b7 and R b8Each of these independently represents a halogen atom, a hydroxyl group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. m2 and n2 each independently represent an integer between 0 and 5. When m2 is 2 or more, multiple R b7 They may be the same or different, and when n2 is 2 or greater, multiple R b8 They may be the same or different. R b9 and R b10 Each of these independently represents either a chain-like hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 These atoms may bond with each other and form a ring together with the sulfur atom to which they are bonded, and the -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R b11 This 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 This 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. The hydrogen atoms contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, and the hydrogen atoms 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 These may be bonded to each other and form a ring including the -CH-CO- groups to which they are bonded, and the -CH2- groups included in the ring may be replaced by -O-, -S-, or -CO-. R b13 ~R b18 and R b21 ~R b26 Each of these independently represents a halogen atom, a hydroxyl group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. Rb13 and R b14 and R b21 and R b22 These atoms may bond with each other and together with the benzene ring to which they are bonded, form a ring containing a sulfur atom, and the -CH2- contained in the ring may be replaced with -O-, -S-, or -CO-. R b27 ~R b29 Each of these independently represents a group containing a hydrogen atom or an acid-unstable group. L b31 and L b41 ~L b43 Each of these independently represents either a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent an integer between 0 and 5. q2 and r2 each independently represent an integer between 0 and 4. u2 represents either 0 or 1. When o2 is 2 or more, multiple R b13 They are the same or different, and when p2 is 2 or more, multiple R b14 They are the same or different, and when q2 is 2 or more, multiple R b15 They are the same or different, and when r2 is 2 or more, multiple R b16 They are the same or different, and when s2 is 2 or more, multiple R b17 They are the same or different, and when t2 is 2 or more, multiple R b18 They are either the same or different. u3 represents an integer between 1 and 3, satisfying the condition 1 ≤ u3 + q23 ≤ 5. u4 and u5 each independently represent an integer between 0 and 3, satisfying 0 ≤ u4 + o21 ≤ 5 and 0 ≤ u5 + p22 ≤ 5. o21, p22, q23, r24, t25, and s26 each independently represent an integer between 0 and 4. When u3, u4, and u5 are each 2 or more, the bases in the parentheses are either the same or different. When o21, p22, q23, r24, t25, and s26 are each 2 or more, multiple R b21 ~R b26 These are either identical or distinct from one another.
[0080] When u2 is 0, then at least one of o2, p2, q2, and r2 is 1 or greater, and R b13 ~R b16 Preferably, at least one of them is a halogen atom, and when u2 is 1, then one of o2, p2, s2, t2, q2 and r2 is 1 or more, and R b13 ~R b18 Preferably, at least one of them is a halogen atom. Furthermore, when u2 is 0, it is preferable that r2 is 1 or greater, and more preferably 1. Also, when u2 is 0 and r2 is 1 or greater, R b16 It is preferable that the atom is a halogen atom. Aliphatic hydrocarbon groups refer to both chain-type hydrocarbon groups and alicyclic hydrocarbon groups. Examples of chain-type hydrocarbon groups 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-like hydrocarbon group preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, norbornyl, and the groups listed below. TIFF2026088086000064.tif11157 In particular, R b9 ~R b12 The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 4 to 12 carbon atoms. Examples of alicyclic hydrocarbon groups in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include methylcyclohexyl group, dimethylcyclohexyl group, 2-methyladamantan-2-yl group, 2-ethyladamantan-2-yl group, 2-isopropyladamantan-2-yl group, methylnorbornyl group, and isobornyl group. In alicyclic hydrocarbon groups 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. A fluorinated alkyl group refers to an alkyl group having 1 to 12 carbon atoms and containing a fluorine atom, such as a fluoromethyl group, difluoromethyl group, trifluoromethyl group, or perfluorobutyl group. 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 phenyl, biphenyl, naphthyl, and phenanthryl groups. Aromatic hydrocarbon groups may have a chain-like hydrocarbon group or an alicyclic hydrocarbon group, and examples include aromatic hydrocarbon groups having a chain-like hydrocarbon group (tolyl, xylyl, cumenyl, mesityl, p-ethylphenyl, p-tert-butylphenyl, 2,6-diethylphenyl, 2-methyl-6-ethylphenyl, etc.) and aromatic hydrocarbon groups having an alicyclic hydrocarbon group (p-cyclohexylphenyl, p-adamantylphenyl, etc.). Furthermore, if 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 a hydrogen atom is substituted with an alkoxy group include the p-methoxyphenyl group. Examples of chain-like hydrocarbon groups in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as benzyl, phenethyl, phenylpropyl, trityl, naphthylmethyl, and naphthylethyl groups. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, and dodecyloxy groups. Examples of alkylcarbonyl groups include acetyl, propionyl, and butyryl groups. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. Examples of alkylcarbonyloxy groups include methylcarbonyloxy group, ethylcarbonyloxy group, propylcarbonyloxy group, isopropylcarbonyloxy group, butylcarbonyloxy group, sec-butylcarbonyloxy group, tert-butylcarbonyloxy group, pentylcarbonyloxy group, hexylcarbonyloxy group, octylcarbonyloxy group, and 2-ethylhexylcarbonyloxy group. R b4 and R b5 The ring formed by the bonding of these atoms to each other and the sulfur atoms to which they are bonded may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. Examples of such rings include those with 3 to 18 carbon atoms, preferably those with 4 to 18 carbon atoms. Furthermore, examples of sulfur atom-containing rings include those with 3 to 12 membered rings, preferably those with 3 to 7 membered rings, and the following rings are examples. * indicates a bonding site. TIFF2026088086000065.tif24142R b9 and R b10 The ring formed by the combination of these elements may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. This ring may be a 3-membered to 12-membered ring, preferably a 3-membered to 7-membered ring. Examples include a thiolan-1-ium ring (tetrahydrothiophenium ring), a thian-1-ium ring, and a 1,4-oxatian-4-ium ring. R b11 and R b12 The ring formed by the combination of these elements may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. This ring may be a 3-membered to 12-membered ring, preferably a 3-membered to 7-membered ring. Examples include oxocycloheptane rings, oxocyclohexane rings, oxonorbornane rings, and oxoadamantane rings. R b27 ~R b29Groups containing acid-unstable groups include -R c30 , -CO-OR c30 or -L c10 -CO-OR c30 The group indicated by (L c10 R represents an alkanediyl group with 1 to 6 carbon atoms. c30 This represents an acid-unstable group. Examples include: R c30 Examples of acid-unstable groups include those represented by formula (1) or formula (2), which will be described later.
[0081] Among cations (b2-1) to (b2-5), cation (b2-1), cation (b2-4), or cation (b2-5) are preferred. The following cations can be considered as cations (b2-1): TIFF2026088086000066.tif171165
[0082] TIFF2026088086000067.tif56163 The following cations can be listed as cations (b2-2). TIFF2026088086000068.tif18150 The following cations are examples of cations (b2-3): TIFF2026088086000069.tif26140 The following cations are examples of cations (b2-4): TIFF2026088086000070.tif130164 The following cations are examples of cations (b2-5). TIFF2026088086000071.tif102165
[0083] The acid generator (B) is a combination of the anion and the organic cation described above, and these can be combined arbitrarily. Preferably, the acid generator (B) is formula (B1a-1) to formula (B1a-4), formula (B1a-7) to formula (B1a-11), formula (B1a-14) to formula (B1a-30), formula (B1a-35) to formula (B1a-70), formula (B2a-1) to formula (B2a-11), formula (B2a-16) to formula (B2a-20), formula (B3a-1) to formula (B3 a-3) Examples include combinations of an anion represented by any of the following formulas: (B3a-11) to (B3a-14), (B4a-1) to (B4a-4), or (B4a-11) to (B4a-14), and a cation (b2-1), (b2-2), (b2-3), (b2-4), or (b2-5).
[0084] Preferably, the acid generator (B) is represented by formulas (B1-1) to (B1-106), (B2-1) to (B2-20), (B3-1) to (B3-28), and (B4-1) to (B4-16). Among these, those containing arylsulfonium cations are preferred, and those represented by formulas (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), (B3-1) to (B3-28), and (B4-1) to (B4-16) are particularly preferred. TIFF2026088086000072.tif171160
[0085] TIFF2026088086000073.tif252158
[0086] TIFF2026088086000074.tif254158
[0087] TIFF2026088086000075.tif254160
[0088] TIFF2026088086000076.tif253161
[0089] TIFF2026088086000077.tif251151
[0090] TIFF2026088086000078.tif249154
[0091] TIFF2026088086000079.tif245143
[0092] TIFF2026088086000080.tif109127
[0093] <Compounds containing the structure represented by formula (L0)> A compound containing the structure represented by formula (L0) (hereinafter sometimes referred to as "compound (L0)") is a compound that contains one or more of the structure represented by formula (L0) as a substructure, and is a compound containing an aromatic hydrocarbon ring having a hydroxyl group or a carboxyl group (phenolic hydroxyl group or benzoic acidic carboxyl group), or a compound in which the hydroxyl group or carboxyl group of these compounds is protected by an acid-unstable group. TIFF2026088086000081.tif2471[In formula (L0), all signs have the same meaning as described above.] Ar lk Examples of aromatic hydrocarbon rings include benzene rings, naphthalene rings, anthracene rings, and phenanthrene rings. Ar lk The substituents that the aromatic hydrocarbon ring may have are R, which will be described later. lk11 and R lk22 Examples of groups similar to those exemplified by the above include the following. Ar lk It is preferably a benzene ring or naphthalene ring which may have substituents, and more preferably a benzene ring which may have substituents. R lkExamples of acid-unstable groups include the group represented by formula (1a) (hereinafter sometimes referred to as "acid-unstable group (1a)") and the group represented by formula (2a) (hereinafter sometimes referred to as "acid-unstable group (2a)"). Among these, the group represented by formula (2a) is preferred. TIFF2026088086000082.tif2156 [In formula (1a), R aa1 , R aa2 and R aa3 Each of these 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 These atoms bond to each other to form a cyclic hydrocarbon group having 3 to 20 carbon atoms, and the alkyl group, the alkenyl group, the cyclic hydrocarbon group, and the aromatic hydrocarbon group may have halogen atoms. * indicates a connection site. TIFF2026088086000083.tif2161 [In formula (2a), R aa1’ and R aa2’ Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R aa3’ represents a hydrocarbon group with 1 to 20 carbon atoms, or R aa2’ and R aa3’ They combine with each other and they join together -CX a - forms a heterocyclic group having 3 to 20 carbon atoms, and the -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 halogen atoms. X a This represents an oxygen atom or a sulfur atom. * indicates a connection site.
[0094] R aa1 , R aa2 and R aa3 Examples of alkyl groups include methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups. aa1 , Raa2 and R aa3 The number of carbon atoms in the alkyl group can be 1 to 8, preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. R aa1 , R aa2 and R aa3 Examples of alkenyl groups include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. R aa1 , R aa2 and R aa3 The alicyclic hydrocarbon group may be 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, norbornyl, and the following groups (* indicates a bonding site). aa1 , R aa2 and R aa3 The number of carbon atoms in the alicyclic hydrocarbon group can be 3 to 20, preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. TIFF2026088086000084.tif9159R aa1 , R aa2 and R aa3 Examples of aromatic hydrocarbon groups include aryl groups such as phenyl, naphthyl, anthryl, biphenyl, and phenanthryl groups. aa1 , R aa2 and R aa3 The number of carbon atoms in the aromatic hydrocarbon group can be 6 to 18, preferably 6 to 14, and more preferably 6 to 10. Examples of combined groups include groups that combine alkyl groups and alicyclic hydrocarbon groups as described above (for example, alkylcycloalkyl groups or cycloalkylalkyl groups such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having alkyl groups (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), aromatic hydrocarbon groups having alicyclic hydrocarbon groups (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), and aryl-cycloalkyl groups such as phenylcyclohexyl group.
[0095] R aa1 and R aa2 -C(R aa1 )(R aa2 )(R aa3 Examples of such groups include the following: 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 bond site with -O-. TIFF2026088086000085.tif30140
[0096] The group represented by formula (1a) is a 1,1,1-trialkyl group (where R is in formula (1a)). aa1 , R aa2 and R aa3 A group in which R is an alkyl group, preferably a tert-butyl group, or a 2-alkyladamantan-2-yl group (in formula (1a), R aa1 , R aa2 And the carbon atoms to which these are bonded form an adamantyl group, R aa3 (a group in which R is an alkyl group) and 1-(adamantan-1-yl)-1,1-dialkyl group (in formula (1a), R aa1 and R aa2 is an alkyl group, R aa3Examples include groups that are adamantyl groups.
[0097] R aa1' , R aa2' and R aa3' Examples of hydrocarbon groups include chain hydrocarbon groups such as alkyl groups, alicyclic hydrocarbon groups, cyclic hydrocarbon groups such as aromatic hydrocarbon groups, and groups formed by combining these. Alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these are R aa1 , R aa2 and R aa3 The same elements mentioned above can be cited. R aa2' and R aa3' They bond with each other, and the carbon atoms and X that they bond to are bonded together. a When forming a heterocyclic group with -C(R aa1' )(R aa2' )-X a -(R aa3' Examples of such groups include the following: * indicates a bonding site. The number of carbon atoms in the heterocyclic group is typically 3 to 20, preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12. TIFF2026088086000086.tif21143R aa1 , R aa2 , R aa3 , R aa1' , R aa2' and R aa3' The halogen atoms that may be present include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms. R aa1' and R aa2' Preferably, at least one of them is a hydrogen atom.
[0098] Specific examples of acid-unstable groups (1a) include the following groups. * indicates a bonding site. TIFF2026088086000087.tif46164Specific examples of acid-unstable groups (2a) include the following groups. * indicates a bonding site. TIFF2026088086000088.tif59148
[0099] lk may be any integer greater than or equal to 2. For example, lk may be any integer less than or equal to 13. In particular, lk is preferably an integer between 1 and 11, more preferably an integer between 1 and 9, even more preferably an integer between 1 and 7, even more preferably an integer between 1 and 6, even more preferably an integer between 1 and 5, and even more preferably an integer between 1 and 4. lo may be any integer greater than or equal to 2. For example, lo may be any integer less than or equal to 13. In particular, lo is preferably an integer between 1 and 11, more preferably an integer between 1 and 9, even more preferably an integer between 1 and 7, even more preferably an integer between 1 and 6, even more preferably an integer between 1 and 5, and even more preferably an integer between 1 and 4.
[0100] Examples of compound (L0) include the compound represented by formula (LX) (hereinafter sometimes referred to as "compound (LX)"). TIFF2026088086000089.tif23131[In formula (LX), all signs have the same meaning as described above.] Ar k1 and Ar k2 As for the aromatic hydrocarbon ring, Ar lk Examples of groups similar to those exemplified in the aromatic hydrocarbon ring include those shown. R lk1 and R lk2 As for the acid-unstable group, R lk Examples of acid-unstable groups include those similar to those exemplified above. Examples of the hydrocarbon group Lx include chain hydrocarbon groups, monocyclic or polycyclic (including spiro rings, fused rings, or cross-linking rings) alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. Groups consisting of two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and a chain hydrocarbon group) are also possible. The hydrocarbon group Lx is a (lx2+1) valent hydrocarbon group and can be a 2- to 7 valent hydrocarbon group depending on lx2. The number of carbon atoms in the hydrocarbon group is preferably 1 to 72, more preferably 1 to 60, even more preferably 1 to 48, even more preferably 1 to 36, and even more preferably 1 to 24. Examples of chain-like hydrocarbon groups include alkanediyl groups, and examples of alkanediyl groups include 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, and tetradecane-1,14-diyl. Examples include linear alkanediyl groups such as pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl; and branched alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. Note that branched alkanediyl groups may have a methyl group at one end. Furthermore, chain-like hydrocarbon groups can also be defined as groups obtained by replacing one or more hydrogen atoms of the aforementioned groups with bonding sites. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, preferably 1 to 10, even more preferably 1 to 9, still more preferably 1 to 8, still more preferably 1 to 6, and still more preferably 1 to 4. Examples of alicyclic hydrocarbon groups include monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; 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 spirocyclic alicyclic hydrocarbon groups such as spiro rings having a norbornyl or adamantyl group with a cycloalkyl group spiro-bonded to each. Furthermore, alicyclic hydrocarbon groups can also be defined as groups obtained by replacing one or more hydrogen atoms of the aforementioned groups with bonding sites. Examples of alicyclic hydrocarbon groups include the following groups. The bonding site can be at any position. TIFF2026088086000090.tif45164 The number of carbon atoms in the alicyclic hydrocarbon group can be 3 to 72, may be 3 to 60, preferably 3 to 24, more preferably 3 to 20, even more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 3 to 12. Examples of aromatic hydrocarbon groups include phenylene groups, naphthylene groups, anthrylene groups, biphenylene groups, phenanthrylene groups, and other arylene groups. Furthermore, aromatic hydrocarbon groups can also include groups obtained by replacing one or more hydrogen atoms of the aforementioned groups with bonding sites. The number of carbon atoms in the aromatic hydrocarbon group can range from 6 to 72, may be 6 to 60, preferably 6 to 24, more preferably 6 to 20, even more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Groups combining two or more types include groups combining an alicyclic hydrocarbon group and a chain hydrocarbon group, groups combining an aromatic hydrocarbon group and a chain hydrocarbon group, and groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group. In the combinations, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. Also, any of the groups may be Ar k1 Or Ar k2 They may be bound together. Examples of groups combining alicyclic hydrocarbon groups and chain hydrocarbon groups include -alicyclic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, and -chain hydrocarbon group-alicyclic hydrocarbon group-. Examples of groups combining an aromatic hydrocarbon group and a chain hydrocarbon group include -aromatic hydrocarbon group-chain hydrocarbon group-, -chain hydrocarbon group-aromatic hydrocarbon group-chain hydrocarbon group-, and -chain hydrocarbon group-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-. Furthermore, other examples of combined groups include those in which one or more hydrogen atoms of the aforementioned groups are replaced at the bonding site. The -CH2- groups in the hydrocarbon group of Lx are -O-, -S-, -SO-, -SO2-, and -NR. 7 - or -CO- may be used instead. The -CH2- contained in the hydrocarbon group is -O-, -S-, -SO-, -SO2-, -NR 7As mentioned above, examples of groups replaced by - or -CO- include hydroxyl groups, carboxyl groups, thiol groups, amino groups, oxy groups, carbonyl groups, thio groups, sulfonyl groups, peptide groups, alkoxy groups, alkylthio groups, alkylsulfonyl groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, alkoxyalkoxy groups, alkoxyalkyl groups, hydroxyalkyl groups, alkylamino groups, alkylpeptide groups, alkanediyloxy groups, alkanediyloxycarbonyl groups, alkanediylcarbonyl groups, alkanediylcarbonyloxy groups, alkanediyloxycarbonyloxy groups, alkanediylsulfonyl groups, alkanediylthio groups, alkanediylamino groups, alkanediylpeptide groups, cycloalkoxy groups, cycloalkylalkoxy groups, alkoxycarbonyloxy 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. These substituted groups may be similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. Furthermore, the -CH2- contained in alicyclic hydrocarbon groups, aromatic hydrocarbon groups, or groups formed by combining alicyclic hydrocarbon groups and aromatic hydrocarbon groups may be -O-, -S-, -CO-, -SO-, -NR 7 The groups replaced by - or -SO2- are similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. The -CH2- contained in the hydrocarbon group is -O-, -S-, -SO-, -SO2-, -NR 7 Groups that have been replaced by - or -CO- include groups in which one or more hydrogen atoms of the above-mentioned group are replaced at the bonding site. Examples of substituents that Lx may have include halogen atoms and cyano groups. When Lx is a group that combines an alicyclic hydrocarbon group or an aromatic hydrocarbon group with a chain hydrocarbon group such as an alkyl group, the chain hydrocarbon group such as an alkyl group can be a substituent of the alicyclic hydrocarbon group or aromatic hydrocarbon group. The -CH2- group contained in the alkyl group and other chain hydrocarbon groups in Lx is -O-, -CO-, -S-, -SO-, -NR 7 By being replaced with - or -SO2-, Lx can substantially have substituents such as hydroxyl groups, carboxyl groups, alkoxy groups, alkylcarbonyl groups, alkoxycarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, alkoxyalkoxy groups, alkylamino groups, amino groups, thiol groups, alkylthio groups, alkylsulfonyl groups, and alkylpeptide groups. The substituents that Lx may have are R, which will be discussed later. lk11 and R lk22 Other groups similar to those exemplified by the above can also be cited.
[0101] R lk11 and R lk22 Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. R lk11 and R lk22 Examples of hydrocarbon groups include chain-type hydrocarbon groups such as alkyl and alkanediyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. Examples of alkyl groups include linear or branched alkyl groups, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, and dodecyl group. Alkanediyl groups include straight-chain or branched 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, and penta Examples include linear alkanediyl groups such as decane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl, and branched alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. The ends of the branched alkanediyl groups may be methyl groups. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 12, more preferably 1 to 9, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. Alicyclic hydrocarbon groups may be monocyclic or polycyclic, and examples of such alicyclic hydrocarbon groups include those similar to those exemplified in Lx. Specifically, examples of monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl groups. Examples of polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl groups. Examples of spirocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as spirocyclohexane-1,2′-cyclopentane and spiroadamantane-2,3'-cyclopentane, and spiro rings having cycloalkyl groups spiro-bonded to norbornyl or adamantyl 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. Examples of aromatic hydrocarbon groups include those similar to those exemplified in Lx. Specifically, examples include phenyl group, naphthyl group, biphenyl group, anthryl group, phenanthryl group, and binaphthyl group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10. Groups formed by combining two or more groups include groups formed by combining an aromatic hydrocarbon group and a chain-like hydrocarbon group (for example, aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*, alkyl group-aromatic hydrocarbon group-alkanediyl group-*, where the -CH2- contained in the alkanediyl group and the alkyl group are -O-, -CO-, -S-, -SO-, -NR 7 -or -SO2- may be replaced.) Groups combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group-alkanediyl group-*, alkyl group-alicyclic hydrocarbon group-*, alkyl group-alicyclic hydrocarbon group-alkanediyl group-*, and the -CH2- contained in the alicyclic hydrocarbon group, the alkanediyl group and the alkyl group are -O-, -CO-, -S-, -SO-, -NR 7-or may be replaced with -SO2-), a group combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, aromatic hydrocarbon group-alicyclic hydrocarbon group-*, alicyclic hydrocarbon group-aromatic hydrocarbon group-*, where the -CH2- contained in the alicyclic hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 7 -It may be replaced with -SO2-.) is an example. * represents a binding site. Examples of aromatic hydrocarbon groups - alkanediyl groups -* include aralkyl groups such as benzyl and phenethyl groups. Examples of alkyl-aromatic hydrocarbon groups-* include tolyl groups, xylyl groups, and cumenyl groups. Examples of alicyclic hydrocarbon groups - alkanediyl groups -* include cyclohexylmethyl group, cyclohexylethyl group, 1-(adamantan-1-yl)methyl group, 1-(adamantan-1-yl)-1-methylethyl group, and other cycloalkylalkyl groups. Examples of alkyl-alicyclic hydrocarbon groups include methylcyclohexyl group, dimethylcyclohexyl group, and cycloalkyl groups having alkyl groups such as 2-alkyladamantan-2-yl group. Examples of aromatic hydrocarbon groups - alicyclic hydrocarbon groups -* include the phenylcyclohexyl group. Examples of alicyclic hydrocarbon groups - aromatic hydrocarbon groups -* include the cyclohexylphenyl group. Furthermore, in the combinations, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. Also, any of these groups may be bonded to a benzene ring. R lk11 and R lk22 The -CH2- groups contained in the hydrocarbon group represented are -O-, -CO-, -S-, -SO-, -NR 7 If it is replaced by - or -SO2-, the number of carbon atoms before replacement shall be the total number of carbon atoms in the hydrocarbon group. This number may be one or two or more. The -CH2- contained in the hydrocarbon group is -O-, -S-, -SO-, -SO2-, -NR 7Groups that can be replaced by - or -CO- include groups similar to those exemplified in Lx, within the limits permitted by the upper limit of the number of carbon atoms. R lk11 and R lk22 Examples of substituents that the hydrocarbon group may have include halogen atoms and cyano groups. R lk11 and R lk22 However, if it is a hydrocarbon group having a halogen atom, R lk11 and R lk22 Examples of hydrocarbon groups having halogen atoms include chain hydrocarbon groups having halogen atoms such as haloalkyl groups, alicyclic hydrocarbon groups having halogen atoms, and aromatic hydrocarbon groups having halogen atoms. A haloalkyl group refers to an alkyl group having a halogen atom. Examples of haloalkyl groups include C1-C12 alkyl fluorides, C1-C12 alkyl chlorides, C1-C12 alkyl bromides, C1-C12 alkyl iodides, and other C1-C12 haloalkyl groups. Specific examples of haloalkyl groups include C1-C12 perfluoroalkyl groups (trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, iodomethyl group, and the like. The number of carbon atoms in the haloalkyl group is preferably 1-9, more preferably 1-6, even more preferably 1-4, and even more preferably 1-3. The -CH2- group in the haloalkyl group may be replaced with -O- or -CO-, etc. Examples of such groups include haloalkoxy groups, haloalkoxycarbonyl groups, haloalkylcarbonyl groups, and haloalkylcarbonyloxy groups. Specifically, examples 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. For example, a group in which one or more hydrogen atoms of the above-executed groups are replaced with halogen atoms can be used. The hydrocarbon group may have one substituent or more substituents. R lk11 and Lx or R lk22 Lx and Lx may each join with each other to form a ring. In this case, the ring is R lk11 and R lk22 However, since each is bonded to an aromatic hydrocarbon ring, examples include fused rings that condense with an aromatic hydrocarbon ring or spiro rings that spirobond with an aromatic hydrocarbon ring. The total number of carbon atoms in these fused rings or spiro rings is 3 to 28, may be 3 to 24, and preferably 3 to 20. The fused rings or spiro rings consist of one or more -O-, -CO-, -S-, -SO-, -NR atoms. 7 It may also be a ring containing - or -SO2-. Aromatic hydrocarbon ring (-R lk11 )-Lx- or aromatic hydrocarbon ring (-R lk22 )-Lx-, R lk11 and Lx or R lk22 Examples of rings formed by the bonding of and Lx include the following groups. The following groups are not listed, but each has at least one R lk1 -OX lk1 - or R lk2 -OX lk2 - has other R lk11 or R lk22 It may have a bond site with an aromatic hydrocarbon ring. * represents a bond site with an aromatic hydrocarbon ring. TIFF2026088086000091.tif18111R lk11 and R lk22 These elements may combine with each other to form a ring. Examples of such rings include those with the structure shown in formula (LX-13), which will be described later.
[0102] Examples of compound (LX) include the compound represented by formula (LX-0) (hereinafter sometimes referred to as "compound (LX-0)"). Preferably, compound (LX-0) is the compound represented by formula (LX-1) (hereinafter sometimes referred to as "compound (LX-1)"). TIFF2026088086000092.tif23125[In formula (LX-0), symbols other than those listed below have the same meaning as above. lk1 represents an integer between 1 and 5, and when lk1 is 2 or greater, the bases within the parentheses may be the same or different from each other. lk11 represents an integer from 0 to 4, satisfying 1 ≤ lk1 + lk11 ≤ 5, and when lk11 is 2 or greater, the bases in multiple parentheses may be the same or different. lk2 represents an integer between 1 and 5, and when lk2 is 2 or greater, the bases within the parentheses may be the same or different from one another. lk22 represents an integer between 0 and 4, satisfying 1 ≤ lk2 + lk22 ≤ 5, and when lk22 is 2 or greater, the bases within the parentheses may be the same or different. TIFF2026088086000093.tif42147[In formula (LX-1), symbols other than those listed below have the same meaning as above. X lk3 This represents a single bond or a carbonyl group. R lk3 This represents a hydrogen atom or an acid-unstable group. Lx1 and Lx2 each independently represent a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents, and the -CH2- contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 7 -It may also be replaced with -SO2-. R lk33 - represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a halogen atom or substituents, and the -CH2- contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 7 -It may also be replaced with -SO2-. lx3 represents an integer from 0 to 6, and when lx3 is 2 or greater, the bases within the parentheses may be the same or different. lk3 represents an integer from 1 to 4, and when lk3 is 2 or greater, the bases within the parentheses may be the same or different from each other. lk33 represents an integer between 0 and 3, satisfying 1 ≤ lk3 + lk33 ≤ 4, and when lk33 is 2 or greater, the bases within the parentheses may be the same or different. A hydrocarbon group which may have substituents Lx1 and Lx2 (the -CH2- contained in the hydrocarbon group may be -O-, -CO-, -S-, -SO-, -NR 7 -Or it may be replaced with -SO2-.) As such, a hydrocarbon group may have the substituents exemplified in Lx, to the extent permitted by the upper limit of the number of carbon atoms, etc. (the -CH2- contained in the hydrocarbon group may be -O-, -CO-, -S-, -SO-, -NR 7 Examples of groups similar to those mentioned above include those that may be replaced by -SO2-. R lk33 A hydrocarbon group which may have a halogen atom or substituent (the -CH2- contained in the hydrocarbon group may be -O-, -CO-, -S-, -SO-, -NR 7 -Or it may be replaced with -SO2-.) As for R, within the limits allowed by the upper limit of the number of carbon atoms, etc. lk11 and R lk22 A hydrocarbon group which may have a halogen atom or substituent as exemplified above (the -CH2- contained in the hydrocarbon group may be -O-, -CO-, -S-, -SO-, -NR 7 Examples of groups similar to those mentioned above include those that may be replaced by -SO2-. R lk11 and Lx1, or R lk22 Lx2 and Lx2 may each join with each other to form a ring. In this case, the ring may be the same as those described above.
[0103] As compound (LX-1), compounds represented by formulas (LX-11), (LX-12), and (LX-13) are preferred (hereinafter, they may be referred to as "compound (LX-11)", "compound (LX-12)", and "compound (LX-13)", respectively). TIFF2026088086000094.tif138156[In formulas (LX-11), (LX-12), and (LX-13), All symbols other than those listed below have the same meaning as described above. Ly represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents, and the -CH2- contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 7-It may also be replaced with -SO2-. A hydrocarbon group which may have a substituent of Ly (the -CH2- contained in the hydrocarbon group may be -O-, -CO-, -S-, -SO-, -NR) 7 -Or it may be replaced with -SO2-.) As such, a hydrocarbon group may have the substituents exemplified in Lx, to the extent permitted by the upper limit of the number of carbon atoms, etc. (the -CH2- contained in the hydrocarbon group may be -O-, -CO-, -S-, -SO-, -NR 7 Examples of groups similar to those mentioned above include those that may be replaced by -SO2-. lk1 and lk2 are each preferably an integer from 1 to 4, more preferably an integer from 1 to 3, and even more preferably 1 or 2. lk11 and lk22 are preferably integers from 0 to 3, and more preferably integers from 0 to 2, respectively. lk3 is preferably an integer between 1 and 3, and more preferably 1 or 2. lk33 is preferably an integer between 0 and 2. lx2 is preferably an integer from 1 to 5, more preferably an integer from 1 to 4, even more preferably an integer from 1 to 3, and even more preferably 1 or 2. lx3 is preferably an integer between 0 and 5, more preferably an integer between 0 and 4, even more preferably an integer between 0 and 3, and even more preferably an integer between 0 and 2. R lk11 , R lk22 and R lk33Each of these is preferably independently a halogen atom, a C1-C6 haloalkyl group, or a C1-C6 alkyl group (the -CH2- contained in the haloalkyl group or alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a C1-C4 haloalkyl group, or a C1-C4 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), even more preferably an iodine atom, a fluorine atom, a C1-C3 fluorinated alkyl group, a hydroxyl group, a carboxyl group, a C1-C3 alkoxy group, a C1-C3 hydroxyalkyl group, or a C1-C3 alkyl group, and even more preferably an iodine atom, a fluorine atom, a trifluoromethyl group, a hydroxyl group, a carboxyl group, a methoxy group, or a methyl group. Lx1, Lx2, and Ly are each preferably independently a chain hydrocarbon group having 1 to 10 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-) or a group combining a chain hydrocarbon group having 1 to 6 carbon atoms and a cyclic hydrocarbon group having 3 to 18 carbon atoms (the -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced with -O- or -CO-), and preferably a chain hydrocarbon group having 1 to 8 carbon atoms (the chain hydrocarbon group may be replaced with -O- or -CO-). It is more preferable that the group is a combination of a chain hydrocarbon group having 1 to 4 carbon atoms and a cyclic hydrocarbon group having 3 to 16 carbon atoms (the -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced with -O- or -CO-), and even more preferable that the group is a combination of a chain hydrocarbon group having 1 to 6 carbon atoms or a chain hydrocarbon group having 1 to 4 carbon atoms and a cyclic hydrocarbon group having 3 to 12 carbon atoms. Also, R lk11 and Lx1 or R lk22 It is also preferable that Lx2 and R combine to form a ring. lk11 and R lk22 It is also preferable that they bond to form a ring.
[0104] In one embodiment, compound (L0) may be a low molecular weight compound. A low molecular weight compound is a compound with a weight-average molecular weight of less than 10,000. When compound (L0) is a low molecular weight compound, the weight-average molecular weight is preferably 7,500 or less, more preferably 5,000 or less, even more preferably 4,000 or less, even more preferably 3,500 or less, even more preferably 3,000 or less, even more preferably 2,500 or less, even more preferably 2,000 or less, and even more preferably 1,500 or less. Also, values of 100 or more are given, preferably 120 or more, more preferably 150 or more, even more preferably 200 or more, and even more preferably 300 or more.
[0105] Among the compounds (L0), low molecular weight compounds having a phenolic hydroxyl group or a benzoic acidic carboxyl group include the compounds represented by the following formula. TIFF2026088086000095.tif209158
[0106] Among the compounds (L0), low molecular weight compounds having a phenolic hydroxyl group or a benzoic acidic carboxyl group include compounds obtained by replacing the hydroxyl group of the above compound with a carboxyl group or a carboxyl group with a hydroxyl group. Note that compound (L0) may have both a hydroxyl group and a carboxyl group. Among the compounds (L0), examples of low molecular weight compounds in which the phenolic hydroxyl group or benzoic acid carboxyl group is protected by an acid-unstable group include the compounds represented by the following formula.
[0107] Among the compounds (L0) listed in TIFF2026088086000096.tif214164, low molecular weight compounds having a phenolic hydroxyl group or a benzoic acid carboxyl group, in which the phenolic hydroxyl group or benzoic acid carboxyl group is protected by an acid-unstable group, include compounds obtained by replacing the ethoxyethoxy group of the above compound with an ethoxyethoxycarbonyl group or an ethoxyethoxycarbonyl group with an ethoxyethoxy group. Note that compound (L0) may have both an ethoxyethoxy group and an ethoxyethoxycarbonyl group.
[0108] In the resist composition of the present invention, when compound (L0) includes a low molecular weight compound, the content of compound (L0) is 0.1% by mass or more, preferably 0.3% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more, relative to the solid content of the resist composition. Alternatively, it may be 90% by mass or less, and may be 80% by mass or less, preferably 70% by mass or less, more preferably 60% by mass or less, and even more preferably 50% by mass or less. Specifically, it is 0.1% by mass or more and 90% by mass or less, preferably 0.3% by mass or more and 70% by mass or less, more preferably 0.5% by mass or more and 60% by mass or less, and even more preferably 1% by mass or more and 50% by mass or less.
[0109] Compounds having a phenolic hydroxyl group or a benzoic acid carboxyl group, and / or compounds in which the phenolic hydroxyl group or benzoic acid carboxyl group of these compounds is protected by an acid-unstable group (L0), may in another embodiment be a resin. If compound (L0) is a resin containing structural units derived from these compounds, the resin is preferably a resin containing structural units represented by formula (a2-A) and / or formula (a1-4). TIFF2026088086000097.tif31127[In formula (a2-A), all signs have the same meaning as above.]
[0110] R a2 and R a27Examples of halogen atoms in this context include fluorine, chlorine, iodine, and bromine atoms. R a2 and R a27 Examples of C1-C6 alkyl groups that may have halogen atoms include trifluoromethyl, difluoromethyl, methyl, perfluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, ethyl, perfluoropropyl, 2,2,3,3,3-pentafluoropropyl, propyl, perfluorobutyl, 1,1,2,2,3,3,4,4-octafluorobutyl, butyl, perfluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, pentyl, hexyl, perfluorohexyl, chloromethyl, bromomethyl, and iodomethyl groups. The number of carbon atoms in the alkyl group is preferably 1-4, more preferably 1-3, and even more preferably 1 or 2. R a2 The hydrogen atom or an alkyl group having 1 to 4 carbon atoms is preferred, a hydrogen atom, a methyl group, or an ethyl group is more preferred, and a hydrogen atom or a methyl group is even more preferred. R a27The alkoxy group, alkoxyalkyl group, alkoxyalkoxy group, alkylcarbonyl group, and alkylcarbonyloxy group are similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. The number of carbon atoms in the alkoxy group is preferably 1 to 4, more preferably 1 to 3. 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 number of carbon atoms in the alkoxyalkyl group is preferably 2 to 8, more preferably 2 to 4. 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 number of carbon atoms in the alkoxyalkoxy group is preferably 2 to 8, more preferably 2 to 4. 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 number of carbon atoms in the alkylcarbonyl group is preferably 2 to 4, and more preferably 2 to 3. The alkylcarbonyl group is preferably an alkylcarbonyl group with 2 to 3 carbon atoms, and more preferably an acetyl group. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 4, and more preferably 2 to 3. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group with 2 to 3 carbon atoms, and more preferably an acetyloxy group. R a27 The group is preferably a halogen atom, a hydroxyl group, a carboxyl group, a C1-C4 alkyl group which may have a halogen atom, a C1-C4 alkoxy group, or a C2-C8 alkoxyalkoxy group; more preferably a fluorine atom, an iodine atom, a hydroxyl 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 hydroxyl group, a methyl group, a methoxy group, or an ethoxyethoxy group.
[0111] A a21Examples of alkanediyl groups include linear 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 include branched alkanediyl groups such as crystalline alkanediyl groups, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, heptane-1,6-diyl group, octane-1,7-diyl group, nonane-1,8-diyl group, decane-1,9-diyl group, and undecane-1,10-diyl group. 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, even more preferably 1 to 4, even more preferably 1 to 3, and even more preferably 1 or 2. a28 Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl groups. A a21 The -CH2- contained in the alkanediyl group is -O-, -CO-, or -NR a28 Examples of groups that can be replaced by - include hydroxyl groups, carboxyl groups, carbonyl groups, oxy groups, amino groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylamino groups, peptide groups, alkanediyloxy groups, alkanediyloxycarbonyl groups, alkanediylcarbonyl groups, alkanediylcarbonyloxy groups, alkanediylsulfonyl groups, alkanediylthio groups, and alkanediylamino groups. These replaced groups are similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. Among them, A a21 The -CH2- contained in the alkanediyl group is -O-, -CO-, or -NR a28 The bases that have been replaced by - 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 - are some examples. In particular, *-CO-O- and *-CO-OA a22 -CO-O-, *-OA a22 -CO-O-, *-CO-NR a28 - is preferable. Here, A a22 * represents an alkanediyl group with 1 to 8 carbon atoms, and * represents R a2 This represents the bonding site with the carbon atom to which it is bonded. a22 The alkanediyl group is, within the limits allowed by the upper limit of the number of carbon atoms, A a21 Similar alkanediyl groups can be cited. A a21 These are single bonds, *-CO-O- or *-CO-OA a22 It is preferably -CO-O-, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-.
[0112] 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 in the case of a benzene ring. a21 The bond may be at the ortho, meta, or para position relative to the bond site. In particular, it is preferable that at least one bond is at the meta or para position, and more preferably at the meta position. In the case of a naphthalene ring, A a21 If the bond position is at position 1, it can bond to any of positions 2 through 8, A a21 If the bond position is at position 2, it may bond to position 1 or any of positions 3 through 8. In particular, A a21If the bonding position is at position 1, it is preferable that at least one bond is at positions 3 to 6, and more preferably at position 3 or 4. a21 If the bonding position is at position 2, it is preferable that the bond is at positions 4 through 7, and more preferably at position 5 or 6.
[0113] Examples of structural units (a2-A) include monomer-derived structural units described in Japanese Patent Publication No. 2010-204634 and Japanese Patent Publication No. 2012-12577. As for the structural unit (a2-A), the structural unit is represented by formulas (a2-2-1) to (a2-2-32), formula (a2-3-1) to (a2-3-24), and in the structural unit represented by formulas (a2-2-1) to (a2-2-32), formula (a2-3-1) to (a2-3-24), the R in the structural unit (a2-A) a2 Examples of structural units in which the corresponding methyl group is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group include these units. TIFF2026088086000098.tif107170
[0114] TIFF2026088086000099.tif83166 When structural units (a2-A) are included in the resin, the content of structural units (a2-A) is preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 15 mol% or more, and even more preferably 20 mol% or more, relative to the total structural units. Furthermore, it is preferably 80 mol% or less, more preferably 70 mol% or less, even more preferably 65 mol% or less, even more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 45 mol% or less, and even more preferably 40 mol% or less. Specifically, it is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, even more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%. The structural unit (a2-A) is derived from a compound (for example, the -CH2-C(-R) of the structural unit (a2-A) a2)- is the CH2=C(-R) double bond before cleavage. a2 Compounds (a2-A', etc.) in the state of () can be incorporated into the resin by polymerization. Alternatively, for example, structural units (a1-4) can be polymerized and then treated with an acid such as p-toluenesulfonic acid to incorporate them into the resin. Furthermore, structural units (a2-A) can be incorporated into the resin by polymerizing acetoxystyrene, etc., and then treated with an alkali such as tetramethylammonium hydroxide.
[0115] TIFF2026088086000100.tif31117[In formulas (a1-4), all signs have the same meaning as above.]
[0116] R in equation (a1-4) a1 , R a17 , A a11 and R a18 These are R in equation (a2-A), respectively. a2 , R a27 , A a21 and R a28 Similar examples include the above. R a17 The group is preferably a halogen atom, a hydroxyl group, a carboxyl group, a C1-C4 alkyl group which may have a halogen atom, a C1-C4 alkoxy group, or a C2-C8 alkoxyalkoxy group; more preferably a fluorine atom, an iodine atom, a hydroxyl 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 hydroxyl group, a methyl group, a methoxy group, or an ethoxyethoxy group.
[0117] 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. R a34 , R a35 and R a36Examples of hydrocarbon groups in this context include alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups that combine these. Examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl groups. Alicyclic hydrocarbon groups may be monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, norbornyl, and the following groups (* indicates a bonding site). Examples of aromatic hydrocarbon groups include phenyl groups, naphthyl groups, anthryl groups, biphenyl groups, phenanthryl groups, and other aryl groups. Examples of combined groups include groups that combine alkyl groups and alicyclic hydrocarbon groups as described above (for example, alkylcycloalkyl groups or cycloalkylalkyl groups such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having alkyl groups (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), aromatic hydrocarbon groups having alicyclic hydrocarbon groups (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), and aryl-cycloalkyl groups such as phenylcyclohexyl group. In particular, R a36 Examples include alkyl groups having 1 to 18 carbon atoms, alicyclic hydrocarbon groups having 3 to 18 carbon atoms, aromatic hydrocarbon groups having 6 to 18 carbon atoms, or groups formed by combining these. R a35 and R a36Examples of divalent heterocyclic groups with 3 to 20 carbon atoms that are formed when these atoms bond with each other and together with the -CO- groups they bond to include the following groups: * represents the bonding site, and one of them is R a34 This is the junction site. TIFF2026088086000102.tif15105
[0118] R a34 Preferably, it is a hydrogen atom. R a35 Preferably, this is 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 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 a combination thereof, 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 groups and alicyclic hydrocarbon groups in R are preferably unsubstituted. a36 In this context, the aromatic hydrocarbon group is preferably an aromatic ring having an aryloxy group with 6 to 10 carbon atoms.
[0119] -OC(R) in structural units (a1-4) a34 )(R a35 )-OR a36 These groups are eliminated upon contact with an acid (e.g., p-toluenesulfonic acid), forming either a hydroxyl group or a carboxyl group, respectively. -X a1 -OC(R a34 )(R a35 )-OR a36 In the case of a benzene ring, A a11 The bond may be at the orthogonal, metagonal, or paragonal position relative to the bond site. In particular, it is preferable that at least one bond is at the orthogonal or paragonal position, and more preferably at the paragonal position. In the case of a naphthalene ring, A a11 If the bond position is at position 1, it can bond to any of positions 2 through 8, Aa11 If the bond position is at position 2, it may bond to position 1 or any of positions 3 through 8. In particular, A a11 If the bonding position is at position 1, it is preferable that at least one bond is at positions 3 to 6, and more preferably at position 3 or 4. a11 If the bonding position is at position 2, it is preferable that the bond is at positions 4 through 7, and more preferably at position 5 or 6. Examples of structural units (a1-4) include monomer-derived structural units described in Japanese Patent Publication No. 2010-204646. Preferably, structural units represented by formulas (a1-4-1) to (a1-4-42) and R in structural unit (a1-4). a1 Examples of structural units in which the hydrogen atom corresponding to is replaced by a halogen atom, a haloalkyl group, or an alkyl group are given, and more preferably, structural units represented by formulas (a1-4-1) to (a1-4-5), (a1-4-10), (a1-4-13), (a1-4-14), (a1-4-19), and (a1-4-20), respectively. TIFF2026088086000103.tif117160
[0120] TIFF2026088086000104.tif77168 When the resin contains structural units (a1-4), the content of these units is 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, with respect to the total amount of all structural units in the resin. Also, a content of 95 mol% or less is mentioned, 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 range is 5 to 95 mol%, preferably 10 to 95 mol%, more preferably 15 to 90 mol%, even more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.
[0121] If the resist composition of the present invention contains a resin, the resin may contain structural units other than the structural units represented by formula (a2-A) and the structural units represented by formula (a1-4). Structural units other than those represented by formula (a2-A) and formula (a1-4) include structural units having acid-unstable groups other than those represented by formula (a1-4) (hereinafter sometimes referred to as "structural unit (a1)"), structural units not having acid-unstable groups other than those represented by formula (a2-A) (hereinafter sometimes referred to as "structural unit (s)") (for example, structural units having halogen atoms as described later (hereinafter sometimes referred to as "structural unit (a4)"), structural units having non-leaved hydrocarbon groups as described later (hereinafter sometimes referred to as "structural unit (a5)"), structural units that decompose upon exposure to generate acid as described later (hereinafter sometimes referred to as "structural unit (a7)"), etc.), and other structural units derived from monomers known in the art.
[0122] <Structural unit (a1)> The structural unit (a1) is derived from a monomer having an acid-unstable group (hereinafter sometimes referred to as "monomer (a1)"). The acid-unstable groups contained in the resin are preferably the group represented by formula (1) (hereinafter also referred to as group (1)) and / or the group represented by formula (2) (hereinafter also referred to as group (2)). TIFF2026088086000105.tif2298[In formula (1), R a1 , R a2 and R a3 Each of these 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. a1 and R a2 These atoms bond to each other to form a cyclic hydrocarbon group having 3 to 20 carbon atoms, and the alkyl group, the alkenyl group, the cyclic hydrocarbon group, and the aromatic hydrocarbon group may have halogen atoms. ma and na each independently represent either 0 or 1, and at least one of ma and na represents 1. * indicates a connection site. TIFF2026088086000106.tif2278[In formula (2), R a1’ and R a2’ Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and R a3’ R represents a hydrocarbon group with 1 to 20 carbon atoms. a2’ and R a3’ These atoms bond to each other to form a heterocyclic group having 3 to 20 carbon atoms, and the -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 halogen atoms. X represents either an oxygen atom or a sulfur atom. 'na' represents either 0 or 1. * indicates a connection site.
[0123] R a1 , R a2 and R a3Examples of alkyl groups in this context include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl groups. R a1 , R a2 and R a3 Examples of alkenyl groups in this context include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. R a1 , R a2 and R a3 The alicyclic hydrocarbon group in may be 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, norbornyl, and the following groups (* indicates a bonding site). a1 , R a2 and R a3 The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16. TIFF2026088086000107.tif10159R a1 , R a2 and R a3 Examples of aromatic hydrocarbon groups in this context include aryl groups such as phenyl, naphthyl, anthryl, biphenyl, and phenanthryl groups. As the combined group, there are groups formed by combining the above-mentioned alkyl group and alicyclic hydrocarbon group (for example, alkylcycloalkyl groups or cycloalkylalkyl groups such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), aralkyl groups such as benzyl group, aromatic hydrocarbon groups having an alkyl group (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), aromatic hydrocarbon groups having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), aryl-cycloalkyl groups such as phenylcyclohexyl group, etc. Preferably, ma is 0 and na is 1. R a1 and R a2 When they are bonded to each other to form an alicyclic hydrocarbon group, examples of -C(R a1 )(R a2 )(R a3 ) include the following groups. The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms. * represents the bonding site with -O-. TIFF2026088086000108.tif27136
[0124] R a1’ 、R a2’ and R a3’ Examples of the hydrocarbon group in R include alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. a1 、R a2 and R a3 are the same as those mentioned for R R a2’ and R a3’ When they are bonded to each other to form a heterocyclic group together with the carbon atom to which they are bonded and X, -C(R a1’ )(R a2’)-XR a3’ The following groups are examples. * indicates a binding site. TIFF2026088086000109.tif19124R a1 , R a2 , R a3 , R a1 , R a2’ and R a3’ The halogen atoms that may be present include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms. R a1’ and R a2’ Preferably, at least one of them is a hydrogen atom. na' is preferably 0.
[0125] The following are examples of base (1): In equation (1), R a1 , R a2 and R a3 A group in which the parentheses is an alkyl group, ma=0, and na=1. A tert-butoxycarbonyl group is preferred as the group. In equation (1), R a1 , R a2 However, these combine with the carbon atoms to which they bond to form an adamantyl group, R a3 A group that is an alkyl group, with ma=0 and na=1. In equation (1), R a1 and R a2 Each of them is an alkyl group independently, and R a3 This is an adamantyl group with ma=0 and na=1. The following are specific examples of group (1). * indicates a bonding site. TIFF2026088086000110.tif149165
[0126] The following are specific examples of group (2). * indicates a bonding site. TIFF2026088086000111.tif55153
[0127] The monomer (a1) is preferably a monomer having an acid-unstable group and an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer having an acid-unstable group. Among (meth)acrylic monomers having acid-unstable groups, those having alicyclic hydrocarbon groups with 5 to 20 carbon atoms are preferred. Using a resin having structural units derived from a monomer (a1) with a bulky structure such as an alicyclic hydrocarbon group in the resist composition can improve the resolution of the resist pattern.
[0128] Structural units derived from (meth)acrylic monomers having group (1) include structural units represented by formula (a1-0) (hereinafter sometimes referred to as structural unit (a1-0)), structural units represented by formula (a1-1) (hereinafter sometimes referred to as structural unit (a1-1)), or structural units represented by formula (a1-2) (hereinafter sometimes referred to as structural unit (a1-2)). Preferably, it is at least one structural unit selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2), and more preferably, it is 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 individually or in combination of two or more. TIFF2026088086000112.tif44143[In formulas (a1-0), (a1-1), and (a1-2), all symbols have the same meaning as described above.]
[0129] R a01 , R a4 and R a5 Examples of halogen atoms in this context include fluorine, chlorine, bromine, or iodine atoms. R a01 , R a4 and R a5Examples of alkyl groups that may have halogen atoms include trifluoromethyl, difluoromethyl, methyl, perfluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, ethyl, perfluoropropyl, 2,2,3,3,3-pentafluoropropyl, propyl, perfluorobutyl, 1,1,2,2,3,3,4,4-octafluorobutyl, butyl, perfluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, pentyl, hexyl, perfluorohexyl, chloromethyl, bromomethyl, and iodomethyl groups. 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 or ethyl group, and more preferably a methyl group. R a01 , R a4 and R a5 This is preferably a hydrogen atom or a methyl group, and more preferably a methyl group. L a01 , L a1 and L a2 Preferably, an oxygen atom or *-O-(CH2) k01 It is -CO-O- (where k01 is preferably an integer from 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 groups, alkenyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof in formula (1) are R a1 , R a2 and R a3 Similar groups to those listed above can be cited. R a02 , R a03 , and R a04 The alkyl group in is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a6 and Ra7 The alkyl group in 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 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 number of carbon atoms in the alicyclic hydrocarbon group is preferably 5 to 12, and more preferably 5 to 10. R a02 , R a03 , R a04 , R a6 and R a7 The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 12, and more preferably 6 to 10. In groups formed by combining an alkyl group and an alicyclic hydrocarbon group, it is preferable that the total number of carbon atoms in the combined alkyl group and alicyclic hydrocarbon group is 18 or less. In groups formed by combining an alkyl group and an aromatic hydrocarbon group, it is preferable that the total number of carbon atoms in the combined alkyl group and aromatic hydrocarbon group is 18 or less. R a02 and R a03 Preferably, this is a C1-C6 alkyl group that may have a halogen atom or a C6-C12 aromatic hydrocarbon group that may have a halogen atom, and more preferably a methyl group, ethyl group, phenyl group or naphthyl group that may have a halogen atom. R a04 Preferably, this is a C1-C6 alkyl group which may have a halogen atom, or a C5-C12 alicyclic hydrocarbon group which may have a halogen atom, and more preferably a methyl group, ethyl group, cyclohexyl group, or adamantyl group which may have a halogen atom. R a6 and R a7is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkenyl group having 2 to 6 carbon atoms which may have a halogen atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, more preferably a methyl group, an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, a phenyl group or a naphthyl group which may have a halogen atom, and even more preferably an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group or a phenyl group which may have a halogen atom. m1’ is preferably any integer from 0 to 3, more preferably 0 or 1. n1 is preferably any integer from 0 to 10, more preferably any integer from 0 to 8, even more preferably any integer from 0 to 3, and still more preferably 0 or 1. n1’ is preferably 0 or 1.
[0130] Examples of the structural unit (a1-0) include structural units represented by any of formula (a1-0-1) to formula (a1-0-24) and structural units in which the methyl group corresponding to R in the structural unit (a1-0) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group (alkyl group having a halogen atom) or another alkyl group. Structural units represented by any of formula (a1-0-1) to formula (a1-0-10), formula (a1-0-13), formula (a1-0-14), formula (a1-0-19) to formula (a1-0-24) are preferred. a01 Examples of the structural unit (a1-1) include structural units derived from the monomers described in JP-A-2010-204646. Among them, structural units represented by any of formula (a1-1-1) to formula (a1-1-7) and structural units in which the methyl group corresponding to R in the structural unit (a1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group are preferred, and structural units represented by any of formula (a1-1-1) to formula (a1-1-4) are more preferred. TIFF2026088086000113.tif119160
[0131] Examples of the structural unit (a1-1) include structural units derived from the monomers described in JP-A-2010-204646. Among them, structural units represented by any of formula (a1-1-1) to formula (a1-1-7) and structural units in which the methyl group corresponding to R in the structural unit (a1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group are preferred, and structural units represented by any of formula (a1-1-1) to formula (a1-1-4) are more preferred. a4 Examples of the structural unit (a1-1) include structural units derived from the monomers described in JP-A-2010-204646. Among them, structural units represented by any of formula (a1-1-1) to formula (a1-1-7) and structural units in which the methyl group corresponding to R in the structural unit (a1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group are preferred, and structural units represented by any of formula (a1-1-1) to formula (a1-1-4) are more preferred. TIFF2026088086000114.tif35170
[0132] The structural unit (a1-2) is a structural unit represented by any of the formulas (a1-2-1) to (a1-2-20), and R in the structural unit (a1-2). a5 Examples of structural units in which the corresponding methyl group is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group include structural units represented by any of the formulas (a1-2-2), (a1-2-5), (a1-2-6), and (a1-2-10) to (a1-2-20). TIFF2026088086000115.tif92164
[0133] When the resin contains structural unit (a1-0) and / or structural unit (a1-1) and / or structural unit (a1-2), the total content of these is 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, relative to the total structural units of the resin. Also, it is 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, it is 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 contains structural units (a1-0), the content is preferably 5 mol% or more, more preferably 10 mol% or more, more preferably 15 mol% or more, even more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, and even more preferably 35 mol% or more, relative to the total structural units of the resin. Also, it is preferably 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, even more preferably 65 mol% or less, and even more preferably 60 mol% or less. Specifically, it is preferably 5 to 80 mol%, preferably 5 to 75 mol%, more preferably 10 to 70 mol%, even more preferably 10 to 65 mol%, and even more preferably 10 to 60 mol%. When the resin contains structural unit (a1-1) and / or structural unit (a1-2), the total content of these is 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, relative to the total structural units of the resin. Also, 95 mol% or less is cited, 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, 10 to 90 mol% is cited, 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%.
[0134] Structural units derived from (meth)acrylic monomers having group (2) include the structural unit represented by formula (a1-5) (hereinafter sometimes referred to as "structural unit (a1-5)"). TIFF2026088086000116.tif4760[In formulas (a1-5), all symbols have the same meaning as described above.]
[0135] R in equation (a1-5) a8 The halogen atom and the alkyl group which may have a halogen atom are R of formula (a1-0). a01 Examples of halogen atoms and alkyl groups that may have halogen atoms are similar to those exemplified. In equation (a1-5), R a8 The preferred element is a hydrogen atom, a methyl group, or a trifluoromethyl group. L 51 An oxygen atom is preferred. L 52 and L 53 Preferably, one of them is -O- and the other is -S-. s1 is preferably 1. s1' is preferably an integer between 0 and 2. Z a1 A single bond or *-CH2-CO-O- is preferred.
[0136] Examples of structural units (a1-5) include monomer-derived structural units described in Japanese Patent Publication No. 2010-61117. Among these, structural units represented by formulas (a1-5-1) to (a1-5-4) are preferred, and structural units represented by formula (a1-5-1) or (a1-5-2) are more preferred. TIFF2026088086000117.tif31130 When the resin contains structural units (a1-5), the content is preferably 1 mol% or more, 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, relative to the total structural units of the resin. Also, it is preferably 80 mol% or less, more 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, 1 to 50 mol% is preferred, 3 to 45 mol% is more preferred, 5 to 40 mol% is even more preferred, and 5 to 30 mol% is even more preferred.
[0137] Examples of structural units (a1) having a base (1) include the structural unit represented by formula (a1-6) (hereinafter sometimes referred to as "structural unit (a1-6)"). TIFF2026088086000118.tif3579[In formulas (a1-6), all symbols have the same meaning as described above.] R in equation (a1-6) a61 The halogen atom and the alkyl group which may have a halogen atom are R of formula (a1-0). a01 Examples of halogen atoms and alkyl groups that may have halogen atoms are similar to those exemplified. R a61 The preferred element is a hydrogen atom, a methyl group, or a trifluoromethyl group. R a62 , R a63 , R a64 and R a65 Examples of alkyl groups in this context include methyl, ethyl, propyl, butyl, pentyl, and hexyl groups. C1-C4 alkyl groups are preferred, C1-C3 alkyl groups are more preferred, and methyl or ethyl groups are even more preferred. Ra62 , R a63 and R a64 Examples of cyclic hydrocarbon groups in this context include alicyclic hydrocarbon groups and aromatic hydrocarbon groups. The alicyclic hydrocarbon group may be monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16, and more preferably 3 to 12. Examples of aromatic hydrocarbon groups include phenylene groups and naphthylene groups. Substituents that the cyclic hydrocarbon group may have include halogen atoms, hydroxyl groups, C1-C6 alkyl groups, C1-C6 alkoxy groups, C2-C12 alkoxyalkyl groups, C2-C12 alkoxyalkoxy groups, C2-C4 alkylcarbonyl groups, C2-C4 alkylcarbonyloxy groups, acryloyloxy groups, or methacryloyloxy groups. These groups are R in formula (a2-A). a27 Examples similar to those exemplified earlier can be given. R a62 and R a63 Examples of rings formed by the bonding of these elements include adamantane rings, cyclopentane rings, or cyclohexane rings. Specifically, R a62 and R a63 -C(R) when they bond to each other to form a ring a62 )(R a63 )(R a64 Examples of such groups include the following: * indicates a bonding site with an oxygen atom. The number of carbon atoms in the ring is preferably 3 to 16, and more preferably 3 to 12. TIFF2026088086000119.tif33110
[0138] L a61 and L a62Examples of C1-C4 alkanediyl groups in this compound include methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, and 2-methylpropane-1,2-diyl group. L a61 and L a62 Preferably, each of these is independently a methylene group or an ethylene group. R a6 The alkyl group is R a61 Examples of alkyl groups similar to the above include: X a61 Preferably, it is a single bond or -CO-O-*, and more preferably a single bond. X a62 Preferably, a single bond or *-OL a61 - and more preferably, a single bond.
[0139] Examples of aromatic hydrocarbon groups with 6 to 20 carbon atoms in Ar include phenylene group, o-methylphenylene group, m-methylphenylene group, p-methylphenylene group, p-ethylphenylene group, p-tert-butylphenylene group, 1-naphthylene group, 2-naphthylene group, 1-antrylene group, 9-antrylene group, biphenylene group, 1-phenanthrylene group, and 2-phenanthrylene group. Substituents that the aromatic hydrocarbon group may have include halogen atoms, hydroxyl groups, C1-C6 alkyl groups, C1-C6 alkoxy groups, C2-C12 alkoxyalkyl groups, C2-C12 alkoxyalkoxy groups, C2-C4 alkylcarbonyl groups, C2-C4 alkylcarbonyloxy groups, acryloyloxy groups, or methacryloyloxy groups. These groups are R in formula (a2-A). a27 Examples similar to those exemplified earlier can be given.
[0140] Alkyl groups are preferably C1-C4 alkyl groups, more preferably methyl or ethyl groups, and even more preferably methyl groups. Alkoxy groups are preferably C1-C4 alkoxy groups, more preferably methoxy or ethoxy groups, and even more preferably methoxy groups. Alkoxyalkyl groups are preferably C2-C8 alkoxyalkyl groups, more preferably methoxymethyl or ethoxyethyl groups, and even more preferably methoxymethyl groups. Alkoxyalkoxy groups are preferably C2-C8 alkoxyalkoxy groups, more preferably methoxyethoxy or ethoxyethoxy groups. Alkylcarbonyl groups are preferably C2-C3 alkylcarbonyl groups, and even more preferably acetyl groups. Alkylcarbonyloxy groups are preferably C2-C3 alkylcarbonyloxy groups, and even more preferably acetyloxy groups. Preferred substituents are halogen atoms, hydroxyl groups, C1-C4 alkyl groups, C1-C4 alkoxy groups, or C2-C8 alkoxyalkoxy groups; more preferably fluorine atoms, iodine atoms, hydroxyl groups, methyl groups, methoxy groups, ethoxy groups, ethoxyethoxy groups, or ethoxymethoxy groups; and even more preferably fluorine atoms, iodine atoms, hydroxyl groups, methyl groups, methoxy groups, or ethoxyethoxy groups. Ar is preferably a phenylene group which may have a substituent, and more preferably a phenylene group which may have a hydroxyl group.
[0141] Examples of structural units (a1-6) include those represented by formulas (a1-6-1) to (a1-6-44), with those represented by formulas (a1-6-1) to (a1-6-9) and (a1-6-37) to (a1-6-44) being preferred, those 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) being more preferred, and those represented by formulas (a1-6-7), (a1-6-8), and (a1-6-37) to (a1-6-44) being even more preferred. In the following structural units, R a61A structural unit in which the hydrogen atom corresponding to is replaced by a methyl group, etc., and R a61 Structural units in which the corresponding methyl group is replaced by a hydrogen atom or the like can also be listed as structural units (a1-6). TIFF2026088086000120.tif226161
[0142] If the resin contains structural units (a1-6), the content is preferably 3 mol% or more, more preferably 5 mol% or more, more preferably 7 mol% or more, even more preferably 10 mol% or more, even more preferably 20 mol% or more, even more preferably 30 mol% or more, and even more preferably 40 mol% or more, relative to the total structural units of the resin. Also, it is preferably 80 mol% or less, more preferably 75 mol% or less, 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 7 to 70 mol%, even more preferably 7 to 65 mol%, and particularly preferably 10 to 60 mol%.
[0143] In addition, the following structural units (a1) can also be listed. TIFF2026088086000121.tif33167 When the resin contains structural units represented by formulas (a1-7-1) to (a1-7-7), the content of these units is 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, relative to the total structural units of the resin. Also, 95 mol% or less is mentioned, 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, 10 to 95 mol% is preferred, 15 to 90 mol% is more preferred, 20 to 85 mol% is even more preferred, 20 to 70 mol% is even more preferred, and 20 to 60 mol% is particularly preferred.
[0144] In addition, the following structural units (a1) can also be listed. TIFF2026088086000122.tif51121 When the resin contains structural units represented by formulas (a1-8-1) to (a1-8-3), the content of these units is 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, relative to the total structural units of the resin. Also, 95 mol% or less is mentioned, 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, 10 to 60 mol% is preferred, 15 to 55 mol% is more preferred, 20 to 50 mol% is even more preferred, 20 to 45 mol% is even more preferred, and 20 to 40 mol% is particularly preferred.
[0145] <Structural unit (s)> Structural units (s) are derived from monomers that do not have acid-unstable groups (hereinafter sometimes referred to as "monomers (s)"). Monomers that do not have acid-unstable groups and are known in the field of photoresists can be used to derive structural units (s). The structural units (s) preferably have a hydroxyl group, a carboxyl group, or a lactone ring. If a resin containing a structural unit having a hydroxyl group or a carboxyl group and not having an acid-unstable group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and not having an acid-unstable group (hereinafter sometimes referred to as "structural unit (a3)") is used in the resist composition of the present invention, the resolution of the resist pattern and the adhesion to the substrate can be improved. In addition to the 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-leaved hydrocarbon group (hereinafter sometimes referred to as "structural unit (a5)"), structural units having a slutone 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)"), or other structural units well known in the art.
[0146] <Structural Unit (a2)> Structural unit (a2) is a structural unit represented by formula (a2), and has a hydroxyl group or a carboxyl group at its terminal end. TIFF2026088086000123.tif40102[In formula (a2), R a2 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and the -CH2- contained in the alkanediyl group is -O-, -CO-, or -NR a28 - may be replaced with this. R a28 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L a21-CH2- represents a single bond or a hydrocarbon group having 1 to 28 carbon atoms, and the hydrocarbon group may have substituents, and the -CH2- contained in the hydrocarbon group may be -O-, -CO-, -S-, -SO-, -NR a28 -It may be replaced with -SO2-. L a22 - represents a chain hydrocarbon group having 1 to 12 carbon atoms, which may have single bonds or fluorine atoms, and the -CH2- contained in the chain hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR a28 -It may be replaced with -SO2-. na2 represents an integer between 1 and 5. When na2 is 2 or greater, multiple L a22 They may be the same or different from each other.
[0147] R in equation (a2) a2 , A a21 and R a28 R in equation (a2-A) is a2 , A a21 and R a28 Similar examples include the above. L a21 The hydrocarbon group in this context is a (Na2+1) valent hydrocarbon group, and includes linear or branched chain hydrocarbon groups, monocyclic or polycyclic (including spiro rings, fused rings, or bridged rings) alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and other cyclic hydrocarbon groups. It may also be a group formed by combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group). L a21 Examples of chain-like hydrocarbon groups include 2- to 6-valent chain-like hydrocarbon groups such as alkanediyl groups, alkanetriyl groups, alkanetetrayl groups, alkampentile groups, and alkanehexyl groups. Examples of alkanediyl groups include A a21 Similar alkanediyl groups can be cited. Examples of alkanetriyl groups include methanetriyl, ethanetriyl, propanetriyl, butanetriyl, pentanetriyl, hexanetriyl, heptanetriyl, octantriyl, nonanetriyl, decantriyl, undecanetriyl, dodecanetriyl, tridecanetriyl, tetradecanetriyl, pentadecanetriyl, hexadecantriyl, and heptadecantriyl. Examples of alkanetetrayl groups include methanetetrayl, ethanetetrayl, propanetetrayl, butanetetrayl, pentanetetrayl, hexanetetrayl, heptanetetrayl, octanetetrayl, nonanetetrayl, decanetetrayl, undecanetetrayl, dodecanetetrayl, tridecanetetrayl, tetradecanetetrayl, pentadecanetetrayl, hexadecanetetrayl, and heptadecanetetrayl. Examples of alkanpentile groups include methanepentile, ethanepentile, propanepentile, butanepentile, pentanepentile, and hexanepentile groups. Examples of alkane hexyl groups include methane hexyl group, ethane hexyl group, propane hexyl group, butane hexyl group, pentane hexyl group, and hexane hexyl group. Other examples include groups in which one or more hydrogen atoms of the aforementioned group are replaced by bonding sites. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, even more preferably 1 to 9, even more preferably 1 to 8, even more preferably 1 to 6, even more preferably 1 to 5, and particularly preferably 1 to 4. L a21 Examples of monocyclic and polycyclic alicyclic hydrocarbon groups in this context include the following alicyclic hydrocarbon groups. The bonding site can be at any position. Examples include cycloalkanediyl groups, cycloalkanetriyl groups, cycloalkanetetrayl groups, cycloalkampentile groups, cycloalkanehexyl groups, and other alicyclic hydrocarbon groups with valencies ranging from 2 to 6. Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, cyclopropanetriyl group, cyclobutanetriyl group, cyclopentanetriyl group, cyclohexanetriyl group, cycloheptanetriyl group, cyclooctanetriyl group, cyclodecanetriyl group, cyclopropanetetrayl group, cyclobutanetetrayl group, cyclopentanetetrayl group, cyclohexanetetrayl group, cycloheptanetetrayl group, cyclooctanetetrayl group, cyclodecanetetrayl group, and monocyclic alicyclic hydrocarbon groups. 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]octanedriyl group, norbornanetetrayl group, adamantanetetrayl group, decahydronaphthalenetetrayl group, and bicyclo[3.3.0]octanetetrayl group. Other examples include groups in which one or more hydrogen atoms of the aforementioned group are replaced by bonding sites. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 18, even more preferably 3 to 16, even more preferably 3 to 12, even more preferably 6 to 12, and even more preferably 6 to 10. L a21 Examples of aromatic hydrocarbon groups in this context include divalent to hexavalent aromatic hydrocarbon groups such as arylene groups, arenetriyl groups, arenetetrayl groups, arenepentile groups, and arenehexile groups. Specifically, examples include phenylene group, naphthylene group, anthreylene group, biphenylene group, phenanthrylene group, benzenetriyl group, naphthalentriyl group, anthracenatelyyl group, biphenylentriyl group, phenanthrentriyl group, benzenetetrayl group, naphthalenetetrayl group, anthracenetetrayl group, biphenylenetetrayl group, phenanthrenetetrayl group, and the like. Other examples include groups in which one or more hydrogen atoms of the aforementioned group are replaced by bonding sites. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, even more preferably 6 to 14, even more preferably 6 to 12, and even more preferably 6 to 10. Examples of groups formed by combining two or more types include groups formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group, groups formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group, groups formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, and groups formed by combining an alicyclic hydrocarbon group, a chain hydrocarbon group and an aromatic hydrocarbon group. In the combinations, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. Also, any of the groups may be A a21 and L a22 They may be bound together. The -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR a28Groups replaced by - or -CO- include hydroxyl groups, carboxyl groups, thiol groups, amino groups, alkoxy groups, alkylthio groups, alkoxycarbonyl groups, alkylsulfonyl groups, peptide groups, alkylamino groups, alkylpeptide groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, alkoxyalkoxy groups, oxy groups, carbonyl groups, thio groups, sulfonyl groups, peptide groups, alkanediyloxy groups, alkanediyloxycarbonyl groups, alkanediylcarbonyloxy groups, alkanediyloxycarbonyloxy groups, alkanediylsulfonyl groups, alkanediylthio groups, alkanediylamino groups, alkanediylpeptide groups, 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. Groups in which one or more hydrogen atoms of these groups are replaced at the bonding site are also included. These substituted groups may be similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. Furthermore, the -CH2- groups contained in alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining them are -O-, -S-, -CO-, -SO-, -NR a28 Groups replaced with - or -SO2- include those similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. L a21 The hydrocarbon group in may have one or more substituents. Examples of substituents include halogen atoms, C1-C12 haloalkyl groups, C1-C16 alkyl groups (where the -CH2- group is replaced by -O- or -CO-), acryloyloxy groups, or methacryloyloxy groups. Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. L a21The hydrocarbon group in the compound can substantially have substituents such as haloalkyl groups by having a halogen atom as a substituent. Examples of haloalkyl groups include alkyl fluorides, alkyl chlorides, alkyl bromides, alkyl iodides, etc., and include chloromethyl, bromomethyl, iodomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, perfluoroethyl, perfluoropropyl, and perfluorobutyl groups. 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 contains a branched structure, L a21 The alkyl group may substantially have substituents such as alkyl groups. Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, and 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, even more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3. L a21 The hydrocarbon group containing -CH2- is -O-, -CO-, -S-, -SO-, -NR a28 - or -SO2- replaced by a group, L a21The substituents can substantially include hydroxyl groups, carboxyl groups, thiol groups, amino groups, alkylthio groups, alkylsulfonyl groups, alkoxy groups, alkoxyalkyl groups, alkoxyalkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylamino groups, alkylpeptide groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, acryloyloxy groups, methacryloyloxy groups, and the like. The number of carbon atoms in the alkoxy group is preferably 1 to 12, 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, alkylcarbonyl group, and alkylcarbonyloxy group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 to 3. The number of carbon atoms in the alkoxyalkyl group and alkoxyalkoxy group is preferably 2 to 12, more preferably 2 to 8, even more preferably 2 to 6, and even more preferably 2 to 4. Examples of the above-mentioned foundations include those similar to those exemplified herein. L a21 The substituents that the hydrocarbon group in the hydrocarbon group may have are preferably a halogen atom, a C1-C8 haloalkyl group, or a C1-C12 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a C1-C6 haloalkyl group, or a C1-C10 alkyl group (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), even more preferably a halogen atom, a C1-C4 haloalkyl group, a C1-C4 alkyl group, a hydroxyl group, a C1-C4 alkoxy group, or a C2-C8 alkoxyalkoxy group, even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxyl 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 trifluoromethyl group, a methyl group, a hydroxyl group, a methoxy group, or an ethoxyethoxy group. Also, L a21When the alkanediyl group is replaced with -O- or -CO-, for example, *-L a23 -X a21 -(L a23 This represents an alkanediyl group with 1 to 8 carbon atoms, X a21 represents -O-, -O-CO-, -CO-O-, or -O-CO-O-, and * represents A a21 It is also preferable that it represents the bonding site with ( ). L a21 This includes single bonds, C1-C12 chain hydrocarbon groups which may have substituents (however, the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), and C3-C20 cyclic hydrocarbon groups which may have substituents (however, the -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, -SO-, -NR a28 A group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms that may have substituents and a cyclic hydrocarbon group having 3 to 20 carbon atoms that may have substituents (however, the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and the -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR a28 Preferably, the -CH2- may be replaced by -O- or -CO-. A chain hydrocarbon group having 1 to 10 carbon atoms that may have substituents (however, the -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), or a cyclic hydrocarbon group having 3 to 18 carbon atoms that may have substituents (however, the -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO-, -NR a28 A group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms that may have substituents and a cyclic hydrocarbon group having 3 to 18 carbon atoms that may have substituents (however, the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and the -CH2- contained in the cyclic hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR a28 It is more preferable that it be replaced with - or -CO-.
[0148] L a22 Examples of linear alkane diyl groups with 1 to 12 carbon atoms include 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 group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, 1-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-dimethylpropane-1,3-diyl group, pentane-2,4-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. 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. The -CH2- groups in the chain hydrocarbon group are -O-, -S-, -CO-, -SO-, and -NR. a28 These may be replaced with - or -SO2-, and examples of these replaced groups are similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. L a22 The fluorine atoms present may be one or two or more. na2 is preferably an integer between 1 and 4, and more preferably an integer between 1 and 3. L a21 However, as structural units (a2) in the case of single bonds or chain hydrocarbon groups, for example, the following structural units can be cited. Of the following structural units, R a2 Structural units in which the corresponding methyl group is replaced by a hydrogen atom or the like are also suitable structural units for structural unit (a2), similar to the structural units described below. TIFF2026088086000125.tif66168
[0149] When manufacturing a resist pattern from the resist composition of the present invention, if a high-energy beam such as a KrF excimer laser (248 nm), electron beam, or EUV (ultra-ultraviolet light) is used as the exposure light source, a structural unit (a2) having a phenolic hydroxyl group is preferred, and the structural unit (a2-A) described above is more preferred. Furthermore, if an ArF excimer laser (193 nm) or the like is used, a structural unit (a2) having an alcoholic hydroxyl group is preferred, and the structural unit (a2-C) described later is more preferred. The structural unit (a2) may consist of one type alone, or two or more types.
[0150] In the structural unit (a2), L a21 When is a cyclic hydrocarbon group, structural units having an alcoholic hydroxyl group or a carboxyl group include the structural unit represented by formula (a2-B) (hereinafter sometimes referred to as "structural unit (a2-B)"), the structural unit represented by formula (a2-C) (hereinafter sometimes referred to as "structural unit (a2-C)"), and the structural unit represented by formula (a2-D) (hereinafter sometimes referred to as "structural unit (a2-D)"). TIFF2026088086000126.tif46101 [In formula (a2-B) and formula (a2-C), R a2 This has the same meaning as equation (a2). R a27 This has the same meaning as equation (a²-A). L a25 is -O- or *-O-(CH2) k2 -CO-O- represents a bond, and k2 represents an integer from 1 to 7. * represents the bonding site with -CO-. X a2 This represents a single bond or -CO-. R a25 and R a26 Each of these independently represents a hydrogen atom, a methyl group, or a hydroxyl group. nB2 represents an integer between 1 and 5. When nB2 is 2 or greater, multiple X a2They may be the same or different from one another. nB22 represents an integer between 0 and 8. When nB22 is 2 or greater, multiple R a27 They may be the same or different from one another. nC22 represents an integer between 0 and 10. When nC22 is 2 or greater, multiple R a27 They may be the same or different from each other. L a25 Preferably, -O- or -O-(CH2) f1 The result is -CO-O- (where f1 represents any integer from 1 to 4), and more preferably -O-. R a2 The group is preferably a methyl group. X a2 The bond is preferably a single bond. R a25 Preferably, it is a hydrogen atom. R a26 This is preferably a hydrogen atom or a hydroxyl group. R a27 The group is preferably a halogen atom, a hydroxyl group, a carboxyl group, a C1-C4 alkyl group which may have a halogen atom, a C1-C4 alkoxy group, or a C2-C8 alkoxyalkoxy group; more preferably a fluorine atom, an iodine atom, a hydroxyl 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 hydroxyl 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 from 0 to 3, more preferably 0, 1, or 2, and even more preferably 0 or 1. nC22 is preferably an integer from 0 to 6, more preferably an integer from 0 to 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1.
[0151] Examples of structural units (a2-B) and structural units (a2-C) include structural units derived from monomers described in Japanese Patent Publication No. 2010-204646, the following structural units, and R in the following structural units. a2 Examples of structural units include those in which the corresponding methyl group or hydrogen atom is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. Among these, structural units represented by any of the formulas (a2-B-1) to (a2-B-5) and (a2-C-1) to (a2-C-9) are preferred. TIFF2026088086000127.tif81164 When the resin contains structural unit (a2-B) or structural unit (a2-C), the content is preferably 1 mol% or more, and more preferably 2 mol% or more, relative to the total structural units of the resin. Also, it is preferably 45 mol% or less, more 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, it is preferably 1 to 45 mol%, more 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%.
[0152] TIFF2026088086000128.tif51105[In formula (a2-D), R a2 and A a21 These expressions have the same meaning as equation (a2). R a27 This has the same meaning as equation (a²-A). R a21 and R a22 Each of these independently represents a fluorinated alkyl group having 1 to 4 carbon atoms. L a24 This 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 between 1 and 5. When nD2 is 2 or greater, the bases within the parentheses may be the same or different. nD22 represents an integer between 0 and 4. When nD22 is 2 or greater, multiple R a27They may be the same or different from one another. However, 1 ≤ nD² + nD²² ≤ 5. R a21 and R a22 Examples of alkyl fluoride groups include, independently, trifluoromethyl group, 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, and 4,4,4-trifluorobutyl group. R a21 and R a22 A trifluoromethyl group is preferred as the component. L a24 Examples of alkanediyl groups include methylene group, ethane-1,1-diyl group, propane-1,1-diyl group, and propane-2,2-diyl group. L a24 A single bond or a methylene group is preferred. R a27 The group is preferably a halogen atom, a hydroxyl group, a carboxyl group, a C1-C4 alkyl group which may have a halogen atom, a C1-C4 alkoxy group, or a C2-C8 alkoxyalkoxy group; more preferably a fluorine atom, an iodine atom, a hydroxyl 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 hydroxyl 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. Furthermore, it is preferable that nD2 is 1 and the group in parentheses is bonded to the para position. nD22 is preferably an integer between 0 and 3, more preferably an integer between 0 and 2, even more preferably 0 or 1, and even more preferably 0.
[0153] It is more preferable that the structural unit (a2-D) is a structural unit represented by the following formula (a2-D1) (hereinafter sometimes referred to as "structural unit (a2-D1)"). TIFF2026088086000129.tif51107[In formula (a2-D1), R a2 , A a21 , R a27 nD2 and nD22 have the same meaning as equation (a2-D). In equation (a2-D1), R a2 This is preferably a hydrogen atom or a methyl group. A a21 The bond is preferably a single bond. R a27 The group is preferably a halogen atom, a hydroxyl group, a carboxyl group, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, or a C2-C8 alkoxyalkoxy group; more preferably a fluorine atom, an iodine atom, a hydroxyl 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 hydroxyl group, a methyl group, a methoxy group, or an ethoxyethoxy group. nD22 is preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, and even more preferably 0 or 1. nD2 is preferably 1, 2, 3, or 4, more preferably 1, 2, or 3, and even more preferably 1 or 2.
[0154] The following are examples of structural units (a2-D). TIFF2026088086000130.tif62168
[0155] In the structural units represented by equations (a2-D-1) to (a2-D-8), R a2 In structural units in which the hydrogen atom corresponding to is replaced by a methyl group, etc., and in structural units represented by formulas (a2-D-9) to (a2-D-16), R a2Structural units in which the corresponding methyl group is replaced by a hydrogen atom or the like can also be given as specific examples of structural unit (a2-D). 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 unit represented by formula (a2-D-1) is even more preferred.
[0156] When the resin contains structural units (a2-D), the content is preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, relative to the total structural units of the resin. Furthermore, it is preferably 80 mol% or less, more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, even more preferably 10 to 70 mol%, and even more preferably 10 to 65 mol%.
[0157] <Structural unit (a3)> The lactone ring of the structural unit (a3) may be a monocyclic ring such as a β-propiolactone ring, a γ-butyrolactone ring, or a δ-valerolactone ring, or it may be a fused ring of a monocyclic lactone ring and another ring. Preferably, it may be a γ-butyrolactone ring, an adamantane lactone ring, or a bridging ring containing a γ-butyrolactone ring structure (for example, a structural unit represented by the following formula (a3-2)).
[0158] 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 included alone, or two or more may be included. TIFF2026088086000131.tif51164[In formulas (a3-1), (a3-2), (a3-3), and (a3-4), L a4 , L a5 and L a6 These are, independently, -O- or *-O-(CH2) k3This represents a base represented by -CO-O-(where k3 is an integer from 1 to 7). L a7 is -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 of these independently represents an alkanediyl group with 1 to 6 carbon atoms. * indicates a bonding site with a carbonyl group. R a18 , R a19 , R a20 and R a24 Each of these independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. X a3 represents -CH2- or an oxygen atom. R a21 This represents an aliphatic hydrocarbon group with 1 to 4 carbon atoms. R a22 , R a23 and R a25 Each of these independently represents a carboxyl group, a cyano group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms. p1 represents an integer between 0 and 5. q1 represents an integer between 0 and 3. r1 represents an integer between 0 and 3. w1 represents an integer between 0 and 8. When p1, q1, r1 and / or w1 are 2 or more, multiple R a21 , R a22 , R a23 and / or R a25 They may be the same as each other, or they may be different.
[0159] R a21 , R a22 , R a23 and R a25Examples of aliphatic hydrocarbon groups in this context include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, and tert-butyl groups. R a18 , R a19 , R a20 and R a24 The halogen atoms and alkyl groups that may have halogen atoms in the formula are R of formulas (a1-0) to (a1-2). a01 , R a4 and R a5 Examples similar to those exemplified earlier can be given. L a8 and L a9 Examples of alkanediyl groups in this compound include methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. L a4 ~L a6 These are each independently, preferably -O- or *-O-(CH2) k3 In -CO-O-, k3 is an integer from 1 to 4, more preferably -O- and *-O-CH2-CO-O-, and even more preferably an oxygen atom. L a7 Preferably -O- or *-OL a8 It is -CO-O-, and more preferably -O-, -O-CH2-CO-O-, or -O-C2H4-CO-O-. R a18 , R a19 , R a20 and R a24 Preferably, it is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group, or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a21 The group is preferably a methyl group. R a22 , Ra23 and R a25 Each of these is independently preferably a carboxyl group, a cyano group, or a methyl group. p1, q1, and r1 are each independently, preferably integers from 0 to 2, and more preferably 0 or 1. w1 is preferably an integer between 0 and 2, and more preferably 0 or 1. In particular, formula (a3-4') is preferred over formula (a3-4). TIFF2026088086000132.tif2857(in the formula, R a24 , L a7 (This expresses the same meaning as above.)
[0160] Examples of structural units (a3) include those derived from monomers described in Japanese Patent Publication No. 2010-204646, Japanese Patent Publication No. 2000-122294, and Japanese Patent Publication No. 2012-41274. Examples of structural units (a3) include those represented by any of the 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 said structural units, R in formulas (a3-1) to (a3-4). a18 , R a19 , R a20 and R a24 A structural unit in which the corresponding methyl group is replaced by a hydrogen atom is preferred. TIFF2026088086000133.tif107163 When the resin contains structural units (a3), the total content is 1 mol% or more, preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, relative to the total structural units of the resin. Also, it is 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 is 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 structural unit (a3-1), structural unit (a3-2), structural unit (a3-3), or structural unit (a3-4) is preferably 1 mol% or more, more preferably 3 mol% or more, even more preferably 5 mol% or more, and even more preferably 10 mol% or more, relative to the total structural units of the resin. Also, it is preferably 60 mol% or less, more preferably 55 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, 1 to 60 mol% is preferred, 3 to 60 mol% is more preferred, 3 to 55 mol% is even more preferred, 5 to 55 mol% is even more preferred, 5 to 50 mol% is even more preferred, and 10 to 50 mol% is even more preferred.
[0161] <Structural Unit (a4)> The structural unit represented by formula (a4) is shown below. TIFF2026088086000134.tif3553[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R42 This represents an aliphatic hydrocarbon group having a halogen atom with 1 to 48 carbon atoms, and the -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-.
[0162] R 42 Aliphatic hydrocarbon groups represented by include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these. Examples of chain-type hydrocarbon groups 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 monocyclic or polycyclic alicyclic hydrocarbon groups include monocyclic alicyclic hydrocarbon groups that are monocyclic cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; and polycyclic alicyclic hydrocarbon groups that are polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, norbornyl, and the following groups (* indicates the bonding site). TIFF2026088086000135.tif10146 Examples of groups formed by combinations 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 alkanediyl groups include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and hexane-1,6-diyl group; and branched alkanediyl groups such as propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-methylbutane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. The end of the branched alkanediyl group may be a methyl group. R42 Examples of halogen atoms contained in the aliphatic hydrocarbon group include fluorine, chlorine, bromine, or iodine atoms. R 42 Groups in which the -CH2- of the aliphatic hydrocarbon group contained in is replaced with -O- or -CO- include hydroxyl groups, carboxyl groups, carbonyl groups, oxy groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkanediyloxy groups, alkanediyloxycarbonyl groups, alkanediylcarbonyl groups, alkanediylcarbonyloxy groups, cycloalkoxy groups, cycloalkylalkoxy groups, and groups formed by combining two or more of these groups. These replaced groups are similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms.
[0163] As a structural unit (a4), R 42 However, it is preferable that it be an aliphatic hydrocarbon group having a fluorine atom, R 42 However, examples of structural units (a4) that are aliphatic hydrocarbon groups containing a fluorine atom include the structural unit represented by formula (a4-1) (hereinafter sometimes referred to as "structural unit (a4-1)"), the structural unit represented by formula (a4-2) (hereinafter sometimes referred to as "structural unit (a4-2)"), the structural unit represented by formula (a4-3) (hereinafter sometimes referred to as "structural unit (a4-3)"), and the structural unit represented by formula (a4-A) (hereinafter sometimes referred to as "structural unit (a4-A)"). The structural unit represented by formula (a4-1) is the structural unit shown below. TIFF2026088086000136.tif3092[In formula (a4-1), R 41 represents a hydrogen atom or a methyl group. L 41 This represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. L 42f This represents an alkanediyl group with 1 to 8 carbon atoms containing a fluorine atom, or a cycloalkanediyl group with 3 to 12 carbon atoms containing a fluorine atom. R 42fThis represents a hydrogen atom or a fluorine atom.
[0164] L 41 Examples of alkanediyl groups in this context include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, and butane-1,4-diyl group, and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, and 2-methylpropane-1,2-diyl group. The end of the branched alkanediyl group may be a methyl group. L 42f Examples of fluorine-containing alkanediyl groups include fluorine-containing methylene groups, fluorine-containing ethylene groups, fluorine-containing propane-1,3-diyl groups, fluorine-containing butane-1,4-diyl groups, fluorine-containing pentane-1,5-diyl groups, fluorine-containing hexane-1,6-diyl groups, fluorine-containing heptane-1,7-diyl groups, fluorine-containing octane-1,8-diyl groups, and other linear alkanediyl groups containing fluorine atoms; Examples of branched alkanediyl groups having a fluorine atom include ethane-1,1-diyl group having a fluorine atom, propane-1,1-diyl group having a fluorine atom, propane-1,2-diyl group having a fluorine atom, propane-2,2-diyl group having a fluorine atom, pentane-2,4-diyl group having a fluorine atom, 2-methylpropane-1,3-diyl group having a fluorine atom, 2-methylpropane-1,2-diyl group having a fluorine atom, pentane-1,4-diyl group having a fluorine atom, and 2-methylbutane-1,4-diyl group having a fluorine atom. The ends of the branched alkanediyl groups may be methyl groups that may also have a fluorine atom. L 42fExamples of cycloalkanediyl groups containing a fluorine atom include monocyclic cycloalkanediyl groups containing a fluorine atom, such as cyclobutane-1,3-diyl group containing a fluorine atom, cyclopentane-1,3-diyl group containing a fluorine atom, cyclohexane-1,4-diyl group containing a fluorine atom, cyclohexene-3,6-diyl group containing a fluorine atom, cycloheptane-1,4-diyl group containing a fluorine atom, and cyclooctane-1,5-diyl group containing a fluorine atom. Examples of polycyclic cycloalkanediyl groups containing a fluorine atom include norbornane-1,4-diyl group containing a fluorine atom, norbornane-2,5-diyl group containing a fluorine atom, 5-norbornene-2,3-diyl group containing a fluorine atom, adamantane-1,5-diyl group containing a fluorine atom, and adamantane-2,6-diyl group containing a fluorine atom. L 42f The number of fluorine atoms in the alkanediyl group and cycloalkanediyl group having fluorine atoms in the above is 1 or more, and preferably 2 or more. L 42f In the above, the alkanediyl group and cycloalkanediyl group having a fluorine atom are preferably a perfluoroalkanediyl group and a perfluorocycloalkanediyl group, respectively.
[0165] L 42fThe perfluoroalkanediyl groups in this product include difluoromethylene, perfluoroethylene, perfluoroethylfluoromethylene, perfluoropropane-1,3-diyl, perfluoropropane-1,2-diyl, perfluoropropane-2,2-diyl, perfluorobutane-1,4-diyl, perfluorobutane-2,2-diyl, perfluorobutane-1,2-diyl, perfluoropentane-1,5-diyl, perfluoropentane-2,2-diyl, and perfluoropentane-3 Examples include 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 perfluorocycloalkanediyl groups in this context include perfluorocyclohexanediyl group, perfluorocyclopentanediyl group, perfluorocycloheptanediyl group, and perfluoroadamantanediyl group.
[0166] L 41 Preferably, it is a single bond or an alkanediyl group having 1 to 3 carbon atoms, more preferably a single bond, a methylene group or an ethylene group, and even more preferably a single bond or a methylene group. L 42f The group is preferably a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluorocycloalkanediyl group having 3 to 12 carbon atoms, more preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and even more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.
[0167] The structural units (a4-1) are the structural units shown below and the R in the structural units (a4-1) within the structural units below. 41One example is a structural unit in which the corresponding methyl group is replaced by a hydrogen atom. The structural unit represented by formula (a4-2) in TIFF2026088086000137.tif55165 is the structural unit shown below. TIFF2026088086000138.tif33102[In formula (a4-2), R 41 represents a hydrogen atom or a methyl group. L 43f This represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms, which may contain a fluorine atom, and the -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. R 43f This represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms, which may contain a fluorine atom, and the -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. However, L 43f and R 43f At least one of them has a fluorine atom, L 43f and R 43f The upper limit for the total number of carbon atoms is 21.
[0168] L 43f and R 43f Examples of aliphatic hydrocarbon groups in this context include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these. 43f and R 43f Examples of aliphatic hydrocarbon groups in L 43f and R 43f As long as the upper limit of the total number of carbon atoms allows, R in equation (a4) 42 Examples of aliphatic hydrocarbon groups include those similar to the aliphatic hydrocarbon groups exemplified.
[0169] 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). TIFF2026088086000139.tif13120[In formula (L43f-1), s represents either 0 or 1. L 45f and L 46f Each of these independently represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, which may contain a fluorine atom. L 47f This represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms, which may have a single bond or a fluorine atom. X 46f and X 47f These represent -O-, -CO-, -CO-O-, or -O-CO-, respectively, independently. 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, where ** is -O-CO-R 43f This is the junction site.
[0170] L in the group represented by formula (L43f-1) 45f , L 46f and L 47f Examples of divalent aliphatic hydrocarbon groups represented by include linear or branched alkanediyl groups and monocyclic or polycyclic divalent alicyclic hydrocarbon groups, as well as divalent aliphatic hydrocarbon groups formed by combining alkanediyl groups and divalent alicyclic hydrocarbon groups. Specifically, examples include methylene groups, ethylene groups, propane-1,3-diyl groups, propane-1,2-diyl groups, butane-1,4-diyl groups, 1-methylpropane-1,3-diyl groups, 2-methylpropane-1,3-diyl groups, and 2-methylpropane-1,2-diyl groups. s is preferably 0.
[0171] The following are examples of groups represented by formula (L43f-1). In the following examples, * and ** represent the bonding site, and ** is -O-CO-R 43f This is the junction site. TIFF2026088086000140.tif47140
[0172] R 43f Preferably, it is an aliphatic hydrocarbon group having a fluorine atom. In this case, the structural unit represented by formula (a4-2) is, for example, the structural unit represented by formula (a4-2A) or (formula a4-2B). TIFF2026088086000141.tif41157 [In formula (a4-2A) and formula (a4-2B), R 41 and L 43f This represents the same thing as in equation (a4-2). R 43fA This 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 contain a fluorine atom, and the -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. X 43 **-O-CO- or **-CO-O-, where ** is A 43f This represents the connection point. R 43fB This represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms, which may contain a fluorine atom. However, in equation (a4-2A), L 43f and R 43fA The total number of carbon atoms is 21 or less, and in formula (a4-2B), L 43f , A 43f , X 43 and R 43fB The total number of carbon atoms is 21 or less, A 43f and R 43fB At least one of them has at least one fluorine atom. R 43fA The aliphatic hydrocarbon group is R, as long as the upper limit of the number of carbon atoms allows. 42 Examples include aliphatic hydrocarbon groups similar to those exemplified above. R 43fA It is preferably an alkyl group having 1 to 13 fluorine atoms, a cycloalkyl group having 3 to 12 fluorine atoms, or a combination thereof, *-(CF2) n43f-R 42’ (* represents the bonding site with the carbonyl group. n43f represents an integer from 1 to 6. R 42’ represents a hydrogen atom or a fluorine atom. ) or a perfluorocycloalkyl group having 3 to 12 carbon atoms is more preferable. A 43f and R 43fB The aliphatic hydrocarbon group is R in formula (a4), as long as the upper limit of the number of carbon atoms allows. 42 Examples include aliphatic hydrocarbon groups similar to those exemplified above. A 43f It is preferably a divalent chain hydrocarbon group which may have a fluorine atom, a divalent alicyclic hydrocarbon group, or a group which is a combination thereof, more preferably a divalent chain hydrocarbon group which has a fluorine atom, and even more preferably an alkanediyl fluoride group which has 1 to 6 carbon atoms. R 43fB The aliphatic hydrocarbon group which may have a fluorine atom is preferably a chain hydrocarbon group which may have a fluorine atom, an alicyclic hydrocarbon group which may have a fluorine atom, or a group which is a combination thereof, 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 which may have a fluorine atom, or a group which is a combination thereof, such as 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, or a 1,1,2,2,3,3,4,4-o Alkyl fluorides such as fluorobutyl group, butyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, pentyl group, hexyl group, perfluorohexyl group, heptyl group, perfluoroheptyl group, octyl group and perfluorooctyl group, cyclopropylmethyl group, cyclopropyl group, cyclobutylmethyl group, cyclopentyl group, cyclohexyl group, perfluorocyclohexyl group, adamantyl group, adamantylmethyl group, adamantyldimethyl group, norbornyl group, norbornylmethyl group, perfluoroadamantyl group, and perfluoroadamantylmethyl group are even more preferred.
[0173] In formula (a4-2B), *-A 43f -X 43 -R 43fB An example of a structure that the group represented by can take is shown below (* indicates the bonding site with the carbonyl group). TIFF2026088086000142.tif15165
[0174] The structural units represented by formula (a4-2A) are the structural units shown below and the R in the structural units represented by formula (a4-2A) in the structural units below. 41 One example is a structural unit in which the corresponding methyl group is replaced by a hydrogen atom. TIFF2026088086000143.tif98165
[0175] The structural units represented by formula (a4-2B) are the structural units shown below and the R in the structural units represented by formula (a4-2B) in the structural units below. 41 One example is a structural unit in which the corresponding methyl group is replaced by a hydrogen atom. TIFF2026088086000144.tif111163
[0176] Another example of a structural unit (a4) is the structural unit represented by formula (a4-3). TIFF2026088086000145.tif3689[In formula (a4-3), R 41 represents a hydrogen atom or a methyl group. L 44f This represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms, which may contain a fluorine atom, and the -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. R 44f This represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms, which may contain a fluorine atom, and the -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. However, L 44f and R 44f At least one of them has a fluorine atom, L44f and R 44f The upper limit for the total number of carbon atoms is 21.
[0177] L 44f and R 44f Examples of aliphatic hydrocarbon groups in this context include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these. 44f and R 44f Examples of aliphatic hydrocarbon groups in L 44f and R 44f As long as the upper limit of the total number of carbon atoms allows, R in equation (a4) 42 Examples of aliphatic hydrocarbon groups include those similar to the aliphatic hydrocarbon groups exemplified. L 44f It is preferably an alkanediyl group having 1 to 14 carbon atoms (the -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), and -(CH2) j1 -,-(CH2) j2 -O-(CH2) j3 - or - (CH2) j4 -CO-O-(CH2) j5 It is more preferable that the group is represented by - (j1 to j5 each independently represent an integer from 1 to 6). It is also even more preferable that it is an alkanediyl group having 1 to 4 carbon atoms (one -CH2- in the alkanediyl group may be replaced by -O-, and one -CH2-CH2- in the alkanediyl group may be replaced by -CO-O- or -O-CO-). R 44f Preferably, the group is an aliphatic hydrocarbon group having 1 to 10 carbon atoms and containing a fluorine atom; more preferably, an alkyl group having 1 to 10 carbon atoms and containing a fluorine atom; more preferably, an alkyl group having 3 to 10 carbon atoms and containing a fluorine atom; even more preferably, an alkyl group having 1 to 10 carbon atoms and containing a fluorine atom; and even more preferably, an alkyl group having 1 to 6 carbon atoms and containing a fluorine atom.
[0178] As a structural unit represented by formula (a4-3), for example, the following structural unit and the structural unit represented by the following formula, R in structural unit (a4-3) 41 One example is a structural unit in which the corresponding methyl group is replaced by a hydrogen atom. TIFF2026088086000146.tif83165
[0179] Another example of a structural unit (a4) is the structural unit represented by formula (a4-A). TIFF2026088086000147.tif3673[In formula (a4-A), R 44 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. X 44 * represents a single bond or *-CO-O-. * represents R 44 This 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 substituents, and the -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O-, -S-, -SO2-, -SO-, or -CO-. R 45 This represents an alkyl fluoride with 1 to 8 carbon atoms. R 46 L represents a hydrogen atom or a fluorinated alkyl group having 1 to 6 carbon atoms, and the fluorinated alkyl group is L 44 It may combine with to form an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-. mi represents an integer between 1 and 4. When mi is 2 or greater, the bases within the parentheses may be the same or different.
[0180] R 44 The halogen atoms and alkyl groups that may have halogen atoms in the formula are R of formulas (a1-0) to (a1-2). a01 , R a4 and R a5 Examples similar to those exemplified earlier can be given. R 44 The hydrogen atom or an alkyl group having 1 to 4 carbon atoms is preferred, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms is more preferred, a hydrogen atom, a methyl group or an ethyl group is even more preferred, and a hydrogen atom or a methyl group is even more preferred.
[0181] L 44 Examples of aliphatic hydrocarbon groups in this context include chain hydrocarbon groups, monocyclic or polycyclic (including spiro rings, fused rings, or bridged rings) alicyclic hydrocarbon groups, and groups formed by combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and a chain hydrocarbon group). Examples of chain-like hydrocarbon groups include divalent to pentavalent chain-like hydrocarbon groups such as alkanediyl groups, alkanetriyl groups, alkanetetrayl groups, and alkampentile groups. Examples of alkanediyl groups include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group and heptadecane-1,17-diyl group, and Examples of branched alkanediyl groups include ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group. Other examples include groups in which one or more hydrogen atoms of the aforementioned group are replaced by bonding sites. The number of carbon atoms in the chain-like hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, even more preferably 1 to 9, even more preferably 1 to 8, even more preferably 1 to 6, even more preferably 1 to 5, and particularly preferably 1 to 4.
[0182] Examples of monocyclic or polycyclic alicyclic hydrocarbon groups include the following alicyclic hydrocarbon groups. The bonding site can be at any position. TIFF2026088086000148.tif45164 For example, divalent to pentavalent alicyclic hydrocarbon groups such as cycloalkanediyl groups, cycloalkanetriyl groups, cycloalkanetetrayl groups, and cycloalkampentile groups are examples. Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, and cyclooctane-1,5-diyl group, and 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, as well as polycyclic alicyclic hydrocarbon groups such as spiro rings having a norbornanediyl group or adamantanediyl group and a cycloalkanediyl group each linked by a spiro. Other examples include groups in which one or more hydrogen atoms of the aforementioned group are replaced by bonding sites. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 3 to 12.
[0183] Examples of groups combining two or more types include groups combining alicyclic hydrocarbon groups and chain hydrocarbon groups. In the combination, two or more types of alicyclic hydrocarbon groups and chain hydrocarbon groups may be combined. Also, any of the groups may be X 44 They may be bound together. Examples of groups combining alicyclic hydrocarbon groups and chain hydrocarbon groups include groups in which an alicyclic hydrocarbon group is bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), groups in which a chain hydrocarbon group is bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.), groups 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.), and groups in which an alicyclic hydrocarbon group and a chain hydrocarbon group are bonded to an alicyclic hydrocarbon group. Examples include groups to which a hydrogenated group is bonded (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), groups to which a chain hydrocarbon group is bonded with a chain hydrocarbon group and a chain hydrocarbon group and a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), and groups to which a chain hydrocarbon group is bonded with a chain hydrocarbon group and a chain hydrocarbon group and a chain hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.). * is X 44 This represents the connection point. Other examples include groups in which one or more hydrogen atoms of the aforementioned group are replaced by bonding sites.
[0184] L 44 The -CH2- contained in the aliphatic hydrocarbon group having 1 to 28 carbon atoms may be replaced with -O-, -S-, -SO-, -SO2-, or -CO-. L 44 If the -CH2- group in an aliphatic hydrocarbon group having 1 to 28 carbon atoms is replaced by -O-, -S-, -SO-, -SO2-, or -CO-, the number of carbon atoms before the replacement shall be considered the number of carbon atoms in the aliphatic hydrocarbon group. Groups in which the -CH2- contained in an aliphatic hydrocarbon group is replaced with -O-, -S-, -SO2-, -SO-, or -CO- include hydroxyl groups, carboxyl groups, thiol groups, alkoxy groups, alkylthio groups, alkoxycarbonyl groups, alkylsulfonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups, oxy groups, carbonyl groups, thio groups, sulfonyl groups, alkanediyloxy groups, alkanediyloxycarbonyl groups, alkanediylcarbonyl groups, alkanediylcarbonyloxy groups, alkanediylsulfonyl groups, alkanediylthio groups, cycloalkoxy groups, cycloalkylalkoxy groups, and groups combining two or more of these groups. These replaced groups are similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. Other examples include groups in which one or more hydrogen atoms of the aforementioned group are replaced by bonding sites. Groups in which the -CH2- contained in an alicyclic hydrocarbon group is replaced with -O-, -S-, -SO-, -CO-, or -SO2- include those similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms.
[0185] L 44 The aliphatic hydrocarbon group in may have one or more substituents. Examples of substituents include halogen atoms, C1-C4 haloalkyl groups, C1-C12 alkyl groups, C3-C18 alicyclic hydrocarbon groups, or C6-C18 aromatic hydrocarbon groups (the -CH2- contained in the alkyl group or alicyclic hydrocarbon group may be replaced with -O- or -CO-). Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. C1-C4 haloalkyl groups include C1-C4 alkyl fluorides, C1-C4 alkyl chlorides, C1-C4 alkyl bromides, and C1-C4 alkyl iodides. Examples of haloalkyl groups include C1-C4 perfluoroalkyl groups (trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, chloromethyl group, bromomethyl group, and iodomethyl group. The number of carbon atoms in the haloalkyl group is preferably 1-3, more preferably 1 or 2. Examples of alkyl groups having 1 to 12 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl groups. 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 even more preferably 1 to 3. Examples of alicyclic hydrocarbon groups having 3 to 18 carbon atoms include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl groups, and polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl groups. 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 phenyl, naphthyl, biphenyl, anthryl, phenanthryl, and binaphthyl groups. 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. If the -CH2- group in an alkyl group is replaced with -O- or -CO-, the number of carbon atoms before replacement shall be the total number of carbon atoms in the alkyl group. Examples of replaced groups include hydroxyl groups, carboxyl groups, alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups, alkylcarbonyloxy groups, and alkoxycarbonyloxy groups. These replaced groups are similar to those exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. 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 the -CH2- contained in an alicyclic hydrocarbon group is replaced with -O- or -CO- include those similar to the groups exemplified herein, within the limits permitted by the upper limit of the number of carbon atoms. L 44 The substituents that the aliphatic hydrocarbon group in the above may have are preferably halogen atoms, C1-C3 haloalkyl groups, C1-C6 alkyl groups, C3-C10 alicyclic hydrocarbon groups, or C6-C10 aromatic hydrocarbon groups (the -CH2- contained in the alkyl group or alicyclic hydrocarbon group may be replaced with -O- or -CO-), more preferably fluorine atoms, iodine atoms, C1-C3 perfluoroalkyl groups, or C1-C4 alkyl groups (the -CH2- contained in the alkyl group may be replaced with -O- or -CO-), and even more preferably fluorine atoms, iodine atoms, trifluoromethyl groups, methyl groups, hydroxyl groups, or methoxy groups. L 44 R 46If the alkyl fluoride does not form an alicyclic hydrocarbon group, it may be a C1-C12 chain hydrocarbon group which may have substituents (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), a C3-C18 alicyclic hydrocarbon group which may have substituents (the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), or a C1-C6 chain hydrocarbon group which may have substituents and an alicyclic hydrocarbon group which may have substituents It is preferably a group formed in combination with a hydrogenated group (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and the -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), and may have substituents. It may be a chain hydrocarbon group having 1 to 8 carbon atoms (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 12 carbon atoms may have substituents, or may have substituents. More preferably, the group is a combination of a chain hydrocarbon group having 1 to 6 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), a chain hydrocarbon group having 1 to 8 carbon atoms which may have substituents (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have substituents, a chain hydrocarbon group having 1 to 6 carbon atoms and It is more preferable that the group is formed by combining a C5- to C12 alicyclic hydrocarbon group which may have substituents (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), or by combining a C5- to C12 alicyclic hydrocarbon group which may have substituents, a C1- to C6 chain hydrocarbon group, and a C5- to C12 alicyclic hydrocarbon group which may have substituents (the -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-).
[0186] R 45Examples of C1-C8 fluoride alkyl groups in this include difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 1,1,2,2-tetrafluoropropyl, 1,1,2,2,3,3-hexafluoropropyl, perfluoroethylmethyl, 1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl, perfluoropropyl, 1,1,2,2-tetrafluorobutyl, 1,1,2,2,3,3-hexafluorobutyl, 1,1,2,2,3,3,4,4-octafluorobutyl, perfluorobutyl, and 1,1-bis(trifluoro)methyl Examples include -2,2,2-trifluoroethyl group, 2-(perfluoropropyl)ethyl group, 1,1,2,2,3,3,4,4-octafluoropentyl group, perfluoropentyl group, 1,1,2,2,3,3,4,4,5,5-decafluoropentyl group, 1,1-bis(trifluoromethyl)-2,2,3,3,3-pentafluoropropyl group, perfluoropentyl group, 2-(perfluorobutyl)ethyl group, 1,1,2,2,3,3,4,4,5,5-decafluorohexyl group, 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexyl group, perfluoropentylmethyl group, perfluorohexyl group, perfluoroheptyl group, and perfluorooctyl group. The number of carbon atoms in the alkyl fluoride 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 In this context, alkyl fluorides with 1 to 6 carbon atoms are R, as long as the upper limit of the carbon number allows. 45 Examples of alkyl fluorides include alkyl fluorides with 1 to 6 carbon atoms. R 45 R 46 In the case of 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, even more preferably a trifluoromethyl group, a perfluoroethyl group, or a perfluoropropyl group, and even more preferably a trifluoromethyl group. R45 R 46 When is a hydrogen atom, it is preferably a C1-C6 alkyl fluoride, more preferably a C1-C5 alkyl fluoride, and even more preferably a C3-C5 alkyl fluoride. R 46 is L 44 When it combines with and forms an alicyclic hydrocarbon group having 3 to 12 carbon atoms, R 46 is L 44 Examples of groups formed by bonding with include the group represented by the following formula. In the following formula, * and ** represent bonding sites, and of the two ** symbols, one represents the bonding site with the hydroxyl group and the other represents R 45 This represents the bonding site with L 44A L 44 It is part of the hydrocarbon group and represents a single bond or an alkanediyl group with 1 to 4 carbon atoms. 46 is L 44 The number of carbon atoms in the alicyclic hydrocarbon group formed by bonding with is preferably 3 to 10, more preferably 3 to 8, and even more preferably 3 to 6. TIFF2026088086000149.tif22138R 46 It is preferable that this is a hydrogen atom or a fluorinated alkyl group having 1 to 3 carbon atoms. mi is preferably an integer between 1 and 3, more preferably 1 or 2, and even more preferably 1.
[0187] Examples of structural units (a4-A) include the following structural units. In the following structural units, R 44 Structural units in which the corresponding methyl group is replaced by a hydrogen atom, halogen atom, haloalkyl group, or alkyl group other than a methyl group, and R 44 Structural units in which the corresponding hydrogen atom is replaced by a halogen atom, a haloalkyl group, or an alkyl group can also be given as specific examples of structural unit (a4-A). TIFF2026088086000150.tif118165
[0188] TIFF2026088086000151.tif73165
[0189] If the resin contains structural units (a4), the content of these units is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and even more preferably 3 to 10 mol%, relative to the total structural units of the resin.
[0190] <Structural Unit (a5)> Examples of non-eliminating hydrocarbon groups in structural unit (a5) include groups having linear, branched, or cyclic hydrocarbon groups. Among these, structural unit (a5) is preferably a group having an alicyclic hydrocarbon group. An example of a structural unit (a5) is the structural unit represented by formula (a5-1). TIFF2026088086000152.tif3971[In formula (a5-1), R 51 represents a hydrogen atom or a methyl group. R 52 This represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and the hydrogen atoms contained in this alicyclic hydrocarbon group may be substituted with an aliphatic hydrocarbon group having 1 to 8 carbon atoms. L 55 This represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.
[0191] R 52 The alicyclic hydrocarbon group in this compound may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. Examples of polycyclic alicyclic hydrocarbon groups include adamantyl and norbornyl groups. Examples of aliphatic hydrocarbon groups 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 substituted alicyclic hydrocarbon groups include the 3-methyladamantyl group. R52 Preferably, it is an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, and more preferably, an adamantyl group, a norbornyl group, or a cyclohexyl group. L 55 Examples of divalent saturated hydrocarbon groups in this context include divalent chain-type saturated hydrocarbon groups and divalent alicyclic saturated hydrocarbon groups, with divalent chain-type saturated hydrocarbon groups being preferred. Examples of divalent chain-type saturated hydrocarbon groups include methylene groups, ethylene groups, propanediyl groups, butanediyl groups, and pentanediyl groups, which are all types of alkanediyl groups. The divalent alicyclic saturated hydrocarbon group may be monocyclic or polycyclic. Examples of monocyclic alicyclic saturated hydrocarbon groups include cycloalkanediyl groups such as cyclopentanediyl and cyclohexanediyl. Examples of polycyclic divalent alicyclic saturated hydrocarbon groups include adamantanediyl and norbornanediyl. L 55 Groups in which the -CH2- contained in the divalent saturated hydrocarbon group represented by is replaced with -O- or -CO- include, for example, the groups represented by formulas (L1-1) to (L1-4). In the following formulas, * and ** represent bonding sites, respectively, and * represents the bonding site with the oxygen atom. TIFF2026088086000153.tif18165[In formula (L1-1), X x1 This represents *-O-CO- or *-CO-O- (* is L x1 This represents the connection site. L x1 This represents a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. L x2 This 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 This represents a divalent aliphatic saturated hydrocarbon group with 1 to 17 carbon ...
Claims
1. A resist composition containing a compound represented by formula (I). [In formula (I), R 5A is, -X 1A -R 10A or -X 1A -L 10A -X 2A -R 10A It represents. R 5B is -X 1B -R 10B or -X 1B -L 10B -X 2B -R 10B represents. X 1A , X 2A , X 1B and X 2B These are, independently, -O-, -CO-, -S-, -SO-, and -SO 2 -, -NR 7 - Or represents a base that combines these elements. R 7 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L 10A and L 10B Each of these independently represents a hydrocarbon group having 1 to 28 carbon atoms, which may have substituents, and the hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. R 10A and R 10B Each of these independently represents either the group represented by formula (IA) or the group represented by formula (IB). L 1A , L 1B , L 2 , L 3 , L 4 and L 5 Each of these independently represents a hydrocarbon group having 1 to 28 carbon atoms, which may have single bonds or substituents, and the hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. X 2 and X 3 These are, independently, -O-, -CO-, -S-, -SO-, and -SO 2 -, -NR 7 - Or represents a base that combines these elements. Ar 1 and Ar 2 Each of these independently represents a polycyclic aromatic hydrocarbon group having 8 to 24 carbon atoms. A 1 This represents a cyclic hydrocarbon group having 3 to 36 carbon atoms, which may have substituents, and the cyclic hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. R 3 and R 6 Each of these independently represents a halogen atom or a hydrocarbon group having 1 to 48 carbon atoms, and the hydrocarbon group may have substituents, and the hydrocarbon group may contain -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. m3 represents an integer from 0 to 4, and when m3 is 2 or greater, multiple R 3 They may be identical or different from one another. m6 represents an integer from 0 to 4, and when m6 is 2 or greater, multiple R 6 They may be identical or different from one another. m4 represents an integer between 0 and 4, and when m4 is 2 or greater, the bases within the multiple parentheses may be the same or different from each other. m5 represents an integer from 1 to 4, and when m5 is 2 or greater, the bases within the parentheses may be the same or different from each other. m7 represents an integer between 1 and 3, and when m7 is 2 or greater, the bases within the parentheses may be the same or different from each other. [In formulas (IA) and (IB), R A This represents a saturated hydrocarbon group having 1 to 12 carbon atoms. u1 represents an integer from 0 to 2, and if u1 is 2, multiple R A They are either identical or different. s1 represents either 1 or 2. t1 represents either 0 or 1, provided that the sum of s1 and t1 is either 1 or 2. s12 represents an integer between 0 and 2. t12 represents an integer between 0 and 2. However, the sum of s12 and t12 is an integer between 0 and 2. L 12 This represents a hydrocarbon group having 1 to 36 carbon atoms, which may have single bonds or substituents, and the hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. L 13 represents a hydrocarbon group having 1 to 36 carbon atoms, which may have substituents, and the hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. * indicates a connection site.
2. L 1A , L 1B , L 2 and L 3 The resist composition according to claim 1, wherein each is independently a single bond or a chain hydrocarbon group having 1 to 4 carbon atoms.
3. L 4 and L 5 However, each can independently be a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms that may have substituents (the chain hydrocarbon group contains -CH 2 The resist composition according to claim 1 or 2, wherein the - may be replaced by -O- or -CO-, and is a C6 to C10 aromatic hydrocarbon group or a group formed by a combination thereof, which may have substituents.
4. A 1 This is a cyclic hydrocarbon group having 3 to 12 carbon atoms, which may have substituents (the cyclic hydrocarbon group contains -CH 2 The resist composition according to claim 1 or 2, wherein the - may be replaced with -O- or -CO-, and the group is an aromatic hydrocarbon group having 6 to 14 carbon atoms that may have substituents or a group formed by combining these.
5. Ar 1 and Ar 2 The resist composition according to claim 1 or 2, wherein the group is derived from a naphthalene ring.
6. Furthermore, the resist composition according to claim 1 or 2, wherein the acid generator comprises a salt represented by formula (B1) or a salt represented by formula (B2). [In formula (B1), L b1 This represents a hydrocarbon group having a single bond or a substituent (nb1+1), and the hydrocarbon group contains -CH 2 - stands for -O-, -S-, -CO-, -SO-, or -SO 2 It may be replaced with -. L b2 This represents a divalent hydrocarbon group having 1 to 24 carbon atoms, which may have single bonds or substituents, and the hydrocarbon group contains -CH 2 - stands for -O-, -S-, -CO-, -SO-, or -SO 2 It may be replaced with -. Y b1 This represents a methyl group which may have substituents or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have substituents, and the cyclic hydrocarbon group contains -CH 2 - is -O-, -S-, -SO-, -SO 2 It may be replaced with - or -CO-. nb1 represents an integer between 1 and 6. When nb1 is 2 or greater, the bases within the parentheses may be the same or different. Z1 + This represents an organic cation. [In formula (B2), A 1 represents a nitrogen atom or a carbon atom. L b2’ This represents a divalent hydrocarbon group having 1 to 24 carbon atoms, which may have single bonds or substituents, and the hydrocarbon group contains -CH 2 - stands for -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 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO- or -SO 2 -2-. nb5 represents an integer of 2 or 3. If 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 from each other, and two groups in parentheses combine to form A 1 A ring containing the element may be formed. Z2 + This represents an organic cation.
7. Furthermore, the resist composition according to claim 1 or 2, further comprising a compound containing a structure represented by formula (L0). [In formula (L0), Ar lk represents an aromatic hydrocarbon ring having 6 to 18 carbon atoms which may have a substituent. X lk This represents a single bond or a carbonyl group. R lk This represents a hydrogen atom or an acid-unstable group. lk represents an integer greater than or equal to 1, and when lk is 2 or greater, the bases within the parentheses may be the same or different. * indicates a connection site. `lo` represents an integer greater than or equal to 1.
8. The resist composition according to claim 7, wherein the compound containing the structure represented by formula (L0) is the compound represented by formula (LX). [In formula (LX), Ar k1 and Ar k2 Each of these independently represents an aromatic hydrocarbon ring having 6 to 18 carbon atoms. X lk1 and X lk2 Each of these independently represents either a single bond or a carbonyl group. R lk1 and R lk2 Each of these independently represents either a hydrogen atom or an acid-unstable group. Lx represents a hydrocarbon group having 1 to 80 carbon atoms, which may have substituents, and the hydrocarbon group contains -CH 2 - is -O-, -CO-, -S-, -SO-, -NR 7 - or - SO 2 It may be replaced with -. R 7 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R lk11 and R lk22 Each of these independently represents a hydrocarbon group having 1 to 20 carbon atoms, which may have a halogen atom or substituents, and the hydrocarbon group contains -CH 2 - is -O-, -CO-, -S-, -SO-, -NR 7 - or - SO 2 It may be replaced by -, R lk11 and R lk22 , R lk11 and Lx or R lk22 Lx may be bonded together to form a ring, and the ring may have substituents, and the ring may contain -CH 2 - is -O-, -S-, -CO-, -SO-, -NR 7 - or - SO 2 It may be replaced with -. lx² represents an integer between 1 and 6, and when lx² is 2 or greater, the bases within the parentheses may be the same or different. lk1' represents an integer between 1 and 13, and when lk1' is 2 or greater, the bases within the parentheses may be the same or different. lk11' represents an integer between 0 and 12, and when lk11' is 2 or greater, the bases within the parentheses may be the same or different. lk2' represents an integer between 1 and 13, and when lk2' is 2 or greater, the bases within the parentheses may be the same or different. lk22' represents an integer between 0 and 12, and when lk22' is 2 or greater, the bases within the parentheses may be the same or different.
9. The resist composition according to claim 7, wherein the compound containing the structure represented by formula (L0) is a resin containing the structural unit represented by formula (a2-A) or the structural unit represented by formula (a1-4). [In formula (a2-A), R a2 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. R a27 This represents a halogen atom, a hydroxyl group, a carboxyl group, a C1-C6 alkyl group which may have a halogen atom, a C1-C6 alkoxy group, a C2-C12 alkoxyalkyl group, a C2-C12 alkoxyalkoxy group, a C2-C4 alkylcarbonyl group, a C2-C4 alkylcarbonyloxy group, an acryloyloxy group, or a methacryloyloxy group. A a21 This represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and the alkanediyl group contains -CH 2 - stands for -O-, -CO-, or -NR a28 It may be replaced with -. R a28 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a2 This represents a single bond or a carbonyl group. nA2 represents an integer from 1 to 5, and when nA2 is 2 or greater, the bases within the parentheses may be the same or different from each other. na21 represents an integer from 0 to 4, and when na21 is 2 or greater, multiple R a27 They may be the same or different from one another. mc represents an integer between 0 and 2. [In formula (a1-4), R a1 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain a halogen atom. R a17 This represents a halogen atom, a hydroxyl group, a carboxyl group, a C1-C6 alkyl group which may have a halogen atom, a C1-C6 alkoxy group, a C2-C12 alkoxyalkyl group, a C2-C12 alkoxyalkoxy group, a C2-C4 alkylcarbonyl group, a C2-C4 alkylcarbonyloxy group, an acryloyloxy group, or a methacryloyloxy group. A a11 This represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and the alkanediyl group contains -CH 2 - stands for -O-, -CO-, or -NR a18 It may be replaced with -. R a18 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a1 This represents a single bond or a carbonyl group. na1 represents an integer from 1 to 5, and when na1 is 2 or greater, the bases within the parentheses may be the same or different from each other. na11 represents an integer from 0 to 4, and when na11 is 2 or greater, multiple R a17 They may be the same or different from one another. mc represents an integer between 0 and 2. R a34 and R a35 Each of these independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R a36 R represents a hydrocarbon group with 1 to 20 carbon atoms, or a34 R represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms. a35 and R a36 These atoms bond to each other, forming a divalent heterocyclic group with 3 to 20 carbon atoms, and the hydrocarbon group and the divalent heterocyclic group contain -CH 2 The dash (-) may be replaced with -O- or -S-.
10. The resist composition according to claim 9, wherein the resin further comprises at least one selected from the group consisting of structural units represented by formula (a1-0), structural units represented by formula (a1-1), structural units represented by formula (a1-2), structural units represented by formula (a1-5), and structural units represented by formula (a1-6). [In formulas (a1-0), (a1-1), and (a1-2), L a01 , L a1 and L a2 These are, independently, -O- or *-O- (CH 2 ) k1 This represents -CO-O-, where k1 is an integer from 1 to 7, and * represents the bonding site with -CO-. R a01 , R a4 and R a5 Each of these independently represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group which may have a halogen atom. R a02 , R a03 and R a04 Each of these 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 consisting of a combination thereof, and the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. R a6 and R a7 Each of these 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 a combination thereof, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom. m1' represents an integer between 0 and 14. n1 represents an integer between 0 and 14. n1' represents an integer between 0 and 3. [In formula (a1-5), R a8 This represents an alkyl group having 1 to 6 carbon atoms, which may contain a halogen atom, a hydrogen atom, or a halogen atom. Z a1 is a single bond or *-(CH 2 ) h3 -CO-L 54 - represents, h3 represents an integer from 1 to 4, and * represents L 51 This represents the connection point. L 51 , L 52 , L 53 and L 54 These represent either -O- or -S- independently. s1 represents an integer between 1 and 3. s1' represents an integer between 0 and 3. [In formula (a1-6), R a61 This represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms that may contain 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 substituents, or R a62 and R a63 They bond to each other, forming a ring with 3 to 20 carbon atoms, R a64 This represents an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms, which may have substituents. X a61 These are single bonds, -CO-O-* or -CO-NR a65 - represents *, where * represents the bonding site with Ar, R a65 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 This is a single bond, *-O-L a61 - or * - CO-O-L a62 - represents the bonding site with Ar, and L a61 and L a62 Each of these 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 substituents.
11. (1) A step of applying the resist composition according to claim 1 or 2 onto a substrate, (2) A step of drying the coated resist composition to form a composition layer, (3) Exposure step of the composition layer, (4) A step of heating the composition layer after exposure, (5) A step of developing the composition layer after heating, A method for manufacturing a resist pattern that includes [the specified element].
12. A compound represented by formula (I). [In formula (I), R 5A is, -X 1A -R 10A or -X 1A -L 10A -X 2A -R 10A It represents. R 5B is, -X 1B -R 10B or -X 1B -L 10B -X 2B -R 10B It represents. X 1A , X 2A , X 1B and X 2B These are, independently, -O-, -CO-, -S-, -SO-, and -SO 2 -, -NR 7 - Or represents a base that combines these elements. R 7 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L 10A and L 10B Each of these independently represents a hydrocarbon group having 1 to 28 carbon atoms, which may have substituents, and the hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. R 10A and R 10B Each of these independently represents either the group represented by formula (IA) or the group represented by formula (IB). L 1A , L 1B , L 2 , L 3 , L 4 and L 5 Each of these independently represents a hydrocarbon group having 1 to 28 carbon atoms, which may have single bonds or substituents, and the hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. X 2 and X 3 These are, independently, -O-, -CO-, -S-, -SO-, and -SO 2 -, -NR 7 - Or represents a base that combines these elements. Ar 1 and Ar 2 Each of these independently represents a polycyclic aromatic hydrocarbon group having 8 to 24 carbon atoms. A 1 This represents a cyclic hydrocarbon group having 3 to 36 carbon atoms, which may have substituents, and the cyclic hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. R 3 and R 6 Each of these independently represents a halogen atom or a hydrocarbon group having 1 to 48 carbon atoms, and the hydrocarbon group may have substituents, and the hydrocarbon group may contain -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. m3 represents an integer from 0 to 4, and when m3 is 2 or greater, multiple R 3 They may be identical or different from one another. m6 represents an integer from 0 to 4, and when m6 is 2 or greater, multiple R 6 They may be identical or different from one another. m4 represents an integer between 0 and 4, and when m4 is 2 or greater, the bases within the multiple parentheses may be the same or different from each other. m5 represents an integer from 1 to 4, and when m5 is 2 or greater, the bases within the parentheses may be the same or different from each other. m7 represents an integer between 1 and 3, and when m7 is 2 or greater, the bases within the parentheses may be the same or different from each other. [In formulas (IA) and (IB), R A This represents a saturated hydrocarbon group having 1 to 12 carbon atoms. u1 represents an integer from 0 to 2, and if u1 is 2, multiple R A They are either identical or different. s1 represents either 1 or 2. t1 represents either 0 or 1, provided that the sum of s1 and t1 is either 1 or 2. s12 represents an integer between 0 and 2. t12 represents an integer between 0 and 2. However, the sum of s12 and t12 is an integer between 0 and 2. L 12 This represents a hydrocarbon group having 1 to 36 carbon atoms, which may have single bonds or substituents, and the hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. L 13 represents a hydrocarbon group having 1 to 36 carbon atoms, which may have substituents, and the hydrocarbon group contains -CH 2 - is -O-, -S-, -SO 2 -, -SO-, -NR 7 It may be replaced with - or -CO-. * indicates a connection site.