Carboxylate, resist composition and method for producing resist pattern

Patent metadata

Field	Value
Publication number	US-12124167-B2
Application number	US-202117521363-A
Country	US
Kind code	B2
Filing date	Nov 8, 2021
Priority date	Nov 11, 2020
Publication date	Oct 22, 2024
Grant date	Oct 22, 2024

Abstract

Provided are a carboxylate capable of producing a resist pattern with satisfactory CD uniformity (CDU), and a resist composition. Disclosed are a carboxylate represented by formula (I) and a resist composition:

wherein Ar represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, X 1 represents an oxygen atom or a sulfur atom, R 1 represents a halogen atom or a haloalkyl group having 1 to 12 carbon atoms, R 2 represents a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms or an alkyl group having 1 to 12 carbon atoms, —CH 2 — included in the haloalkyl group and the alkyl group may be replaced by —O— or —CO—, m1 represents an integer of 1 to 6, m2 represents an integer of 0 to 4, and Z + represents an organic cation.

First claim

What is claimed is:

1. A resist composition comprising
an acid generator, and
a carboxylate represented by formula (I):

wherein, in formula (I),
Ar represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent,
X 1 represents an oxygen atom or a sulfur atom,
R 1 represents a halogen atom or a haloalkyl group having 1 to 12 carbon atoms,
R 2 represents a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and —CH 2 — included in the haloalkyl group and the alkyl group may be replaced by —O— or —CO—,
m1 represents an integer of 1 to 6, 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 4, and when m2 is 2 or more, a plurality of R 2 may be the same or different from each other, and
Z + represents an organic cation.

2. The resist composition according to claim 1 , wherein Ar is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent.

3. The resist composition according to claim 1 , wherein X 1 is an oxygen atom.

4. The resist composition according to claim 1 , wherein R 1 is an iodine atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms.

5. The resist composition according to claim 1 , wherein R 2 is an iodine atom, a fluorine atom, a hydroxy group, a perfluoroalkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms.

6. The resist composition according to claim 1 , further comprising a resin having an acid-labile group.

7. The resist composition according to claim 6 , wherein the resin having an acid-labile group includes at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1) 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 ) k1 —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,
o1 represents an integer of 0 to 14,
n1 represents an integer of 0 to 10, and
n1′ represents an integer of 0 to 3.

8. The resist composition according to claim 6 , wherein the resin having an acid-labile group includes 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 ) ab —, and * represents a bonding site 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.

9. The resist composition according to claim 8 , wherein
mb is 1 or more,
at least one of 1 or more R a51 is a hydroxy group.

10. The resist composition according to claim 6 , wherein
the resin having an acid-labile group includes a structural unit represented by formula (a3-4):

wherein, in formula (a3-4),
L a7 represents —O—, *—O-L a8 -O—, *—O-L a8 -CO—O—, *—O-L a8 -CO—O-L a9 -CO—O— or *—O-L a8 -O—CO-L a9 -O—,
L a8 and L a9 each independently represent an alkanediyl group having 1 to 6 carbon atoms,
* represents a bonding site to a carbonyl group,
R a24 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom,
R a25 represents a carboxy group, a cyano group or an aliphatic hydrocarbon group having 1 to 4 carbon atoms,
w1 represents an integer of 0 to 8, and
when w1 is 2 or more, a plurality of R a25 may be the same or different from each other.

11. The resist composition according to claim 1 , wherein the acid generator includes a salt represented by formula (B1):

wherein, in formula (B1),
Q b1 and Q b2 each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms,
L b1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, —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 —CH 2 — included in the alicyclic hydrocarbon group may be replaced by —O—, —SO 2 — or —CO—, and
Z1 + represents an organic cation.

12. A method for producing a resist pattern, which comprises:
(1) a step of applying the resist composition according to claim 1 on a substrate,
(2) a step of drying the applied resist composition to form a composition layer,
(3) a step of exposing the composition layer,
(4) a step of heating the exposed composition layer, and
(5) a step of developing the heated composition layer.

13. The resist composition according to claim 1 , wherein
Ar is a phenylene group which has a hydroxy group at the o-position of Ar with respect to the bonding site of COO″.

14. The resist composition according to claim 1 , wherein
Ar is a phenylene group, and
the bonding site of X to Ar is the p-position of Ar with respect to the bonding site of COO.

15. The resist composition according to claim 1 , wherein
m2 is 2 or more, and
at least one of 2 or more R 2 s is a hydroxy group bounded to the p-position of the phenylene group with respect to X 1 .

16. The resist composition according to claim 1 , wherein
R 1 is an iodine at

Assignees

• Sumitomo Chemical Co

Inventors

• Shimada Masahiko
• Ichikawa Koji

Classifications

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/2006

  using coherent light; using polarised light · CPC title

• G03F7/162

  Coating on a rotating support, e.g. using a whirler or a spinner · CPC title