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US-12619145-B2 - Carboxylate, carboxylic acid generator, resin, resist composition and method for producing resist pattern

US12619145B2US 12619145 B2US12619145 B2US 12619145B2US-12619145-B2

Abstract

A carboxylate represented by formula (I), a resin comprising a structural unit derived from the carboxylate represented by formula (I), a resit composition comprising the carboxylate represented by formula (I) or a resin comprising a structural unit derived from the carboxylate represented by formula (I).

Inventors

  • Masahiko Shimada
  • Koji Ichikawa

Assignees

  • SUMITOMO CHEMICAL COMPANY, LIMITED

Dates

Publication Date
20260505
Application Date
20221031
Priority Date
20211110

Claims (20)

  1. 1 . A carboxylate represented by formula (I) or a structural unit represented by formula (IP): wherein, in formula (I) and formula (IP), R 4 , R 5 , and R 7 each independently represent a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, each of the hydrocarbon group may have a substituent, and a —CH 2 — included in each of the haloalkyl group and the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO 2 —, R 8 represents an iodine atom, a fluorine atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, when m4 is 1 or more, one R 4 of one or more R 4 s is an iodine atom, A 1 and A 2 each independently represent a hydrocarbon group having 1 to 20 carbon atoms, each of the hydrocarbon group may have a substituent, and —CH 2 — included in each of the hydrocarbon group may be replaced by —O—, —CO—, or —S—, m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m2 represents an integer of 0 to 5, and when m2 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R 4 may be the same or different from each other, m5 represents an integer of 0 to 5, and when m5 is 2 or more, a plurality of R 5 may be the same or different from each other, m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R 7 may be the same or different from each other, m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R 8 may be the same or different from each other, in which 1<m1+m7<5,0<m2+m8≤5, X 0 represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH 2 — included in the hydrocarbon group may be replaced by —O—, —S—, —CO—or —SO 2 —, R bb1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, X 10 represents a single bond, *—O—**, *—CO—O—**, *—O—CO—O—** or *-Ax-Ph-Ay-**, Ph represents a phenylene group which may have a substituent, Ax represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, Ay represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, * represents a bonding site to carbon atoms to which R bb1 is bonded, ** represents a bonding site to L 10 , and L 10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and a —CH 2 —included in each of the hydrocarbon group may be replaced by —O—, —S—, —SO 2 —or —CO—.
  2. 2 . The carboxylate according to claim 1 , wherein A 1 is ***—X 01 -L 01 - or ***-L 01 -X 01 —, A 2 is ***—X 02 -L 02 - or ***-L 02 -X 02 —, X 01 and X 02 each independently represent-O—, —CO—, or —S—, L 01 and L 02 each independently represent a single bond or a hydrocarbon group having 1 to 18 carbon atoms, and *** represents a bonding site to the benzene ring to which It is bonded.
  3. 3 . The carboxylate according to claim 1 , wherein X 01 and X 02 are oxygen atoms.
  4. 4 . The carboxylate according to claim 2 , wherein L°1 and L 02 are each independently a single bond or an alkanediyl group having 1 to 6 carbon atoms.
  5. 5 . The carboxylate according to claim 1 , wherein X 0 includes an aliphatic hydrocarbon group having 1 to 72 carbon atoms which may have a substituent and —CH 2 —included in the aliphatic hydrocarbon group may be replaced by —O—, —S—, —CO—or —SO 2 —, or an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent.
  6. 6 . The carboxylate according to claim 5 , wherein X 0 includes an alicyclic hydrocarbon group having 3 to 36 carbon atoms which may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, and a —CH 2 —included in the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO—or —SO 2 —, a group obtained by combining an alicyclic hydrocarbon group having 3 to 36 carbon atoms with a chain hydrocarbon group having 1 to 18 carbon atoms, and a —CH 2 —included in the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO—or —SO 2 —, a —CH 2 —included in the chain hydrocarbon group may be replaced by —O—or —CO—, and the alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, or an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group.
  7. 7 . The carboxylate according to claim 5 , wherein X 0 includes the alicyclic hydrocarbon group, and the alicyclic hydrocarbon group includes; a cycloalkanediyl group having 5 or 6 carbon atoms, an adamandiyl group, a norbornanediyl group, or a polycyclic alicyclic hydrocarbon group in which a cycloalkanediyl group having 5 or 6 carbon atoms and an adamantanediyl group are spiro-bonded, a —CH 2 —included in the adamantanediyl group, the norbornanediyl group and the cycloalkanediyl group may be replaced by —O—or —CO—, a —CH 2 —CH 2 —included in the adamantanediyl group and the norbornanediyl group may be replaced by —O—CO—, and the cycloalkanediyl group may be an acetal ring.
  8. 8 . The carboxylate according to claim 1 , wherein X 10 is a single bond or a group represented by any one of formula (X 1 -1), formula (X 1 -2′) to formula (X 1 -7′) and formula (X 1 -8): wherein, in formula (X 1 -1), formula (X 1 -2′) to formula (X 1 -7′) and formula (X 1 -8), * and ** are bonding sites, and ** represents a bonding site to L 10 , Rx represents a halogen atom, a hydroxy group, an alkyl fluoride group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and mx represents an integer of 0 to 4.
  9. 9 . The carboxylate according to claim 1 , wherein L 10 is a single bond or an alkanediyl group having 1 to 4 carbon atoms, and a —CH 2 —included in the alkanediyl group may be replaced by —O—or —CO—.
  10. 10 . A resin comprising a structural unit represented by formula (IP) according to claim 1 .
  11. 11 . The resin according to claim 10 , further comprising a structural unit having an acid-labile group.
  12. 12 . A resist composition comprising the carboxylate according to claim 1 or a resin including a structural unit represented by formula (IP) according to claim 1 .
  13. 13 . The resist composition according to claim 12 , further comprising; a resin including a structural unit having an acid labile group, wherein the acid-labile group includes at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2): wherein, in formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 each independently represent-O—or *—O—(CH 2 ) k 1-CO—O—, k1 represents an integer of 1 to 7, and * represents a bonding site to—CO—, R a01 , R a4 and R a5 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, R a02 , R a03 and R a04 each independently represent 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 obtained by combining these groups, R a6 and R a7 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these groups, m1 represents an integer of 0 to 14, n1 represents an integer of 0 to 10, and n1′ represents an integer of 0 to 3.
  14. 14 . The resist composition according to claim 12 , further comprising: a resin including a structural unit represented by formula (a2-A): wherein, in formula (a2-A), R a50 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, R a51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group, A a50 represents a single bond or *—X a51 —(A a52 -X a52 ) nb —, and * represents a bond to carbon atoms to which-R a50 is bonded, A a52 represents an alkanediyl group having 1 to 6 carbon atoms, x a51 and X a52 each independently represent-O—, —CO—O—or —O—CO—, nb represents 0 or 1, and mb represents an integer of 0 to 4, and when mb is an integer of 2 or more, a plurality of R a51 may be the same or different from each other.
  15. 15 . The resist composition according to claim 12 , further comprising: an acid generator including a salt represented by formula (B1): wherein, in formula (B1), Q b1 and Q b2 each independently represent a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms, L b1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, a —CH 2 —included in the divalent saturated hydrocarbon group may be replaced by —O—or —CO—, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, Y represents a methyl group which may have a substituent or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and a —CH 2 —included in the alicyclic hydrocarbon group may be replaced by —O—, —S—, —SO 2 —or —CO—, and Z + represents an organic cation.
  16. 16 . A resist composition comprising the carboxylate according to claim 1 and a resin including a structural unit having an acid labile group.
  17. 17 . A resist composition comprising a resin including the structural unit represented by formula (IP) according to claim 1 and a structural unit having an acid labile group.
  18. 18 . A resist composition comprising the carboxylate according to claim 1 and a resin including the structural unit represented by formula (IP) according to claim 1 .
  19. 19 . A method for producing a resist pattern, which comprises: (1) a step of applying the resist composition according to claim 13 on a substrate, (2) a step of drying the applied composition to form a composition layer, (3) a step of exposing the composition layer, (4) a step of heating the exposed composition layer, and (5) a step of developing the heated composition layer.
  20. 20 . A carboxylate represented by formula (I) or a structural unit represented by formula (IP): wherein, in formula (I) and formula (IP), R 4 represents a halogen atom, a hydroxy group or a haloalkyl group having 1 to 12 carbon atoms, R 5 and R 7 each independently represent a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, each of the hydrocarbon group may have a substituent, and a —CH 2 —included in each of the haloalkyl group and the hydrocarbon group may be replaced by —O—, —CO—, —S—or —SO 2 —, R 8 represents a branched alkyl group having 3 or 4 carbon atoms, A 1 represents ***—X 01 -L-01-or ***-L 01 -X 01 —, X 01 represents-O—or —S—, L 01 represents a single bond or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and —CH 2 —included in each of the hydrocarbon group may be replaced by —O—, —CO—, or —S—, *** represents a bonding site to a benzene ring to which I + is bonded, A 2 represents a hydrocarbon group having 1 to 20 carbon atoms, each of the hydrocarbon group may have a substituent of a halogen or a cyano group, and —CH 2 —included in each of the hydrocarbon group may be replaced by —O—, —CO—, or —S—, m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, m2 represents 0, m4 represents an integer of 1 to 5, and when m4 is 2 or more, a plurality of R 4 may be the same or different from each other, m5 represents 0, m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R 7 may be the same or different from each other, m8 represents 1, in which 1<m1+m7<5,0≤m2+m8≤5, X 0 represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH 2 —included in the hydrocarbon group may be replaced by —O—, —S—, —CO—or —SO 2 —, R bb1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, X 10 represents a single bond, *—O—**, *—CO—O—**, *—O—CO—O—** or *-Ax-Ph-Ay-**, Ph represents a phenylene group which may have a substituent, Ax represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, Ay represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond, * represents a bonding site to carbon atoms to which R bb1 is bonded, ** represents a bonding site to L 10 , and L 10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and a —CH 2 —included in each of the hydrocarbon group may be replaced by —O—, —S—, —SO 2 —or —CO—.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority under 35 U.S.C 119 to Japanese Patent Application No. 2021-183586 filed on Nov. 10, 2021 and Japanese Patent Application No. 2022-038540 filed on Mar. 11, 2022. Each of the above applications is hereby expressly incorporated by reference, in its entirety, into the present application. FIELD The present disclosure relates to a carboxylate, a carboxylic acid generator, a resin, a resist composition and a method for producing a resist pattern. BACKGROUND ART JP 2011-037834 A mentions a resist composition comprising a resin including a structural unit derived from a carboxylate represented by the following formula. The present disclosure provides a carboxylate forming a resist pattern with mask error factor (MEF) which is better than that of the above resist composition comprising a resin including a structural unit derived from a carboxylate. SUMMARY The present disclosure includes the following some embodiments. Some embodiments are a salt represented by formula (I) and a resin comprising a structural unit represented by formula (IP): wherein, in formula (I) and formula (IP), R4, R5, R7 and R8 each independently represent a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, each of the hydrocarbon group may have a substituent, and a —CH2— included in each of the haloalkyl group and the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO2—,A1 and A2 each independently represent a hydrocarbon group having 1 to 20 carbon atoms, each of the hydrocarbon group may have a substituent, and —CH2— included in each of the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO2—,m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other,m2 represents an integer of 0 to 5, and when m2 is 2 or more, a plurality of groups in parentheses may be the same or different from each other,m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R4 may be the same or different from each other,m5 represents an integer of 0 to 5, and when m5 is 2 or more, a plurality of R5 may be the same or different from each other,m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R7 may be the same or different from each other,m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R8 may be the same or different from each other,in which 1≤m1+m7≤5, 0≤m2+m8≤5,X0 represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH2— included in the hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO2—,Rbb1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom,X10 represents a single bond, *—O—**, *—CO—O—**, *—O—CO—O—** or *-Ax-Ph-Ay-**,Ph represents a phenylene group which may have a substituent,Ax represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond,Ay represents a single bond, an ether bond, an ester bond or a carbonic acid ester bond,* represents a bonding site to carbon atoms to which Rbb1 is bonded,** represents a bonding site to L10, and L10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and a —CH2— included in each of the hydrocarbon group may be replaced by —O—, —S—, —SO2— or —CO—. Some embodiments are resist compositions comprising a salt represented by above formula (I). Some embodiments are resist compositions comprising a resin including a structural unit represented by above formula (IP). Some embodiments are methods for producing a resist pattern, which comprises: (1) a step of applying the resist compositions comprising the salt represented by formula (I) and/or the resin including a structural unit represented by above formula (IP). It is possible to produce a resist pattern with satisfactory mask error factor (MEF) by using a resist composition which uses a carboxylate of the present disclosure. DETAILED DESCRIPTION In the present specification, “(meth)acrylic monomer” means “at least one of acrylic monomer and methacrylic monomer”. Notations such as “(meth)acrylate” and “(meth)acrylic acid” have the same meaning. In groups mentioned in the present specification, regarding groups capable of having both a linear structure and a branched structure, they may have either the linear or branched structure. When —CH2— included in the hydrocarbon group or the like is replaced by —O—, —S—, —CO— or —SO2—, the same examples shall apply for each group. “Combined group” means a group in which two or more exemplified groups are bonded, and valences of those groups may be appropriately varied by bonding forms. “Derived” means that a polymerizable C═C bond included in the molecule becomes a —C—C— group by polymerization. When stereoisom