Resin, resist composition and method for producing resist pattern

Patent metadata

Field	Value
Publication number	US-9996002-B2
Application number	US-201514854963-A
Country	US
Kind code	B2
Filing date	Sep 15, 2015
Priority date	Sep 16, 2014
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

A resist composition includes (A1) a resin which includes a structural unit represented by formula (a4), a structural unit having a cyclic carbonate and a structural unit represented by formula (I), the resin has no acid-labile group; (A2) a resin which has an acid-labile group; and an acid generator:

wherein R 3 represents a hydrogen atom or a methyl group, R 4 represents a C 1 to C 24 saturated hydrocarbon group having a fluorine atom, and a methylene group contained in the saturated hydrocarbon group may be replaced by an oxygen atom or a carbonyl group, R 1 represents a hydrogen atom or a methyl group, and L 1 represents a single bond or a C 1 to C 18 divalent saturated hydrocarbon group where a methylene group may be replaced by an oxygen atom or a carbonyl group, and R 2 represents a C 3 to C 18 alicyclic hydrocarbon group where a hydrogen atom may be replaced by a C 1 to C 8 aliphatic hydrocarbon group or a hydroxy group, provided that the carbon atom directly bonded to L 1 has no aliphatic hydrocarbon group by which a hydrogen atom has been replaced.

First claim

What is claimed is:

1. A resist composition comprising
(A1) a resin which consists of a structural unit represented by formula (a4):

wherein R 3 represents a hydrogen atom or a methyl group,
R 4 represents a C 1 to C 24 saturated hydrocarbon group having a fluorine atom, and a methylene group contained in the saturated hydrocarbon group may be replaced by an oxygen atom or a carbonyl group,
a structural unit having a cyclic carbonate and
a structural unit represented by formula (I):

wherein R 1 represents a hydrogen atom or a methyl group,
L 1 represents a single bond, a C 1 to C 5 alkanediyl group, or a group represented by the formula (L1-1), the formula (L1-2), the formula (L1-3) or the formula (L1-4),

wherein X X1 represents an oxycarbonyl group or a carbonyloxy group,
L X1 represents a C 1 to C 16 divalent saturated aliphatic hydrocarbon group,
L X2 represents a single bond or a C 1 to C 15 divalent saturated aliphatic hydrocarbon group,
provided that the total carbon number contained in the groups of L X1 and L X2 is 16 or less;
L X3 represents a single bond or a C 1 to C 17 divalent saturated aliphatic hydrocarbon group,
L X4 represents a single bond or a C 1 to C 16 divalent saturated aliphatic hydrocarbon group,
provided that the total carbon number contained in the groups of L X3 and L X4 is 17 or less;
L X5 represents a C 1 to C 15 divalent saturated aliphatic hydrocarbon group,
L X6 and L X7 each independently represent a single bond or a C 1 to C 14 divalent saturated aliphatic hydrocarbon group,
provided that the total carbon number contained in the groups of L X5 , L X6 and L X7 is 15 or less;
L X8 and L X9 each independently represent a single bond or a C 1 to C 12 divalent saturated aliphatic hydrocarbon group,
W X1 represents a C 3 to C 15 divalent saturated alicyclic hydrocarbon group,
provided that the total carbon number contained in the groups of L X8 , L X9 and W X1 is 15 or less;
R 2 represents a C 3 to C 18 alicyclic hydrocarbon group where a hydrogen atom may be replaced by a C 1 to C 8 aliphatic hydrocarbon group or a hydroxy group, provided that the carbon atom directly bonded to L 1 has no aliphatic hydrocarbon group by which a hydrogen atom has been replaced, and
the resin having no acid-labile group;
(A2) a resin which has an acid-labile group; and
an acid generator.

2. The resist composition according to claim 1 , wherein
the cyclic carbonate is a ring represented by formula (x1):

3. The resist composition according to claim 1 , wherein
the structural unit having a cyclic carbonate is a structural unit represented by formula (XX):

wherein R x represents a C 1 to C 6 alkyl group that may have a halogen atom, a hydrogen atom or a halogen atom,
A x represents a C 1 to C 18 divalent saturated hydrocarbon group where a methylene group may be replaced by an oxygen atom or a carbonyl group, and
ring W x represents a cyclic carbonate that may have a substituent.

4. The resist composition according to claim 1 , wherein
R 2 is an unsubstituted C 3 to C 18 alicyclic hydrocarbon group.

5. The resist composition according to claim 1 , wherein
the structural unit represented by the formula (a4) is at least one structural unit selected from the group consisting of a structural unit represented by formula (a4-0), a structural unit represented by formula (a4-1), a structural unit represented by formula (a4-2) and a structural unit represented by formula (a4-3):

wherein R f1 represents a hydrogen atom or a methyl group, and
R f2 represents a C 1 to C 20 saturated hydrocarbon group having a fluorine atom;

wherein R f3 represents a hydrogen atom or a methyl group,
L 3 represents a C 1 to C 18 divalent saturated hydrocarbon group where a methylene group may be replaced by an oxygen atom or a carbonyl group, and
R f4 represents a C 1 to C 20 saturated hydrocarbon group having a fluorine atom;

wherein R f5 represents a hydrogen atom or a methyl group,
L 4 represents a C 1 to C 18 divalent saturated hydrocarbon group where a methylene group may be replaced by an oxygen atom or a carbonyl group, and
R f6 represents a C 1 to C 20 saturated hydrocarbon group having a fluorine atom;

wherein R f7 represents a hydrogen atom or a methyl group,
L 5 represent a C 1 to C 6 alkanediyl group,
A f13 represents a C 1 to C 18 divalent saturated hydrocarbon group that may have a fluorine atom,
X f12 represents an oxycarbonyl group or a carbonyloxy group, and
A f14 represents a C 1 to C 17 saturated hydrocarbon group that may have a fluorine atom,
provided that at least one of A f13 and A f14 represents a saturated hydrocarbon group having a fluorine atom.

6. The resist composition according to claim 1 , wherein
the resin (A2) comprises a structural unit selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2):

wherein L a1 and L a2 independently represent —O— or *—O—(CH 2 ) k1 —CO—O—,
k1 represents an integer of 1 to 7,
represents a binding site to —CO—,
R a4 and R a5 each independently represent a hydrogen atom or a methyl group,
R a6 and R a7 each independently represent a C 1 to C 8 alkyl group, a C 3 to C 18 alicyclic hydrocarbon group or a combination thereof,
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.

7. The resist composition according to claim 6 , wherein
the resin (A2) comprises a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2).

8. A method for producing a resist pattern comprising steps (1) to (5);
(1) applying the resist composition according to claim 1 onto a substrate;
(2) drying the applied composition to form a composition layer;
(3) exposing the composition layer;
(4) heating the exposed composition layer, and
(5) developing the heated composition layer.

9. A resin consisting of:
a structural unit represented by formula (a4):

wherein R 3 represents a hydrogen atom or a methyl group,
R 4 represents a C 1 to C 24 saturated h

Assignees

• Sumitomo Chemical Co

Inventors

• Nishimura Takashi
• Nakano Shota
• Ichikawa Koji

Classifications

• G03F7/0397 Primary

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/322

  Aqueous alkaline compositions · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title