Compound, resin and photoresist composition

Patent metadata

Field	Value
Publication number	US-2016237190-A1
Application number	US-201615042880-A
Country	US
Kind code	A1
Filing date	Feb 12, 2016
Priority date	Feb 18, 2015
Publication date	Aug 18, 2016
Grant date	—

Abstract

A compound represented by formula (I):

wherein R 1 represents a hydrogen atom or a methyl group;
R 2 represents a C1-C12 hydrocarbon group; X a and X b each independently represent an oxygen atom or a sulfur atom; X 11 represents a C1-C12 divalent saturated hydrocarbon group where a hydrogen atom can be replaced by a fluorine atom; and A 1 represents a C1-C12 divalent saturated hydrocarbon group or *-A 2 -X 1 -(A 3 -X 2 ) a -A 4 -, where * represents a binding site to an oxygen atom, A 2 , A 3 and A 4 each independently represent a C1-C12 divalent hydrocarbon group, X 1 and X 2 each independently represent —O—, —CO—O—, —O—CO— or —O—CO—O—, and “a” represents 0 or 1.

First claim

What is claimed is:

1 . A compound represented by formula (I):

wherein R 1 represents a hydrogen atom or a methyl group;
R 2 represents a C1-C12 hydrocarbon group;
X a and X b each independently represent an oxygen atom or a sulfur atom;
X 11 represents a C1-C12 divalent saturated hydrocarbon group where a hydrogen atom can be replaced by a fluorine atom; and
A 1 represents a C1-C12 divalent saturated hydrocarbon group or *-A 2 -X 1 -(A 3 -X 2 ) a -A 4 -, where * represents a binding site to an oxygen atom, A 2 , A 3 and A 4 each independently represent a C1-C12 divalent hydrocarbon group, X 1 and X 2 each independently represent —O—, —CO—O—, —O—CO— or —O—CO—O—, and “a” represents 0 or 1.

2 . The compound according to claim 1 ,
wherein A 1 represents a C1-C4 alkanediyl group or *-A 2 -X 1 -A 4 -, where A 2 , X 1 and A 4 are each independently as defined in claim 1 and * represents a binding site to an oxygen atom.

3 . The compound according to claim 1 ,
wherein X 11 represents a C1-C12 divalent saturated hydrocarbon group where a hydrogen atom has been replaced by a fluorine atom.

4 . The compound according to claim 1 , which compound is represented by formula (IA):

wherein R 1 , R 2 and A 1 are each independently as defined in claim 1 ;
R f1 and R f2 each independently represent a fluorine atom or a C1-C6 fluorinated alkyl group; and
“n” represents an integer of 1 to 10.

5 . A resin which comprises a structural unit derived from the compound according to claim 1 .

6 . The resin according to claim 5 , which further comprises a structural unit having an acid-labile group, said structural unit being different from the structural unit derived from the compound represented by formula (I).

7 . The resin according to claim 6 , wherein
the structural unit having an acid-labile group is represented by formula (a1-1) or formula (a1-2):

in which L a1 and L a2 each independently represents an oxygen atom or *—O—(CH 2 ) k1 —CO—O— in which * represents a binding site to —CO—, and k1 represents an integer of 1 to 7;
R a4 and R a5 each independently represent a hydrogen atom or a methyl group;
R a6 and R a7 each independently represent a C1-C8 alkyl group, a C3-C18 alicyclic hydrocarbon group, or a combination of them;
“m1” represents an integer of 0 to 14; “n1” represents an integer of 0 to 10; and “n1′” represents 0 to 3.

8 . The resin according to claim 7 ,
which comprises the structural unit represented by formula (a1-1) and the structural unit represented by formula (a1-2).

9 . The resin according to claim 5 ,
which further comprises a structural unit having a lactone ring.

10 . The resin according to claim 9 , wherein
the structural unit having a lactone ring is represented by formula (a3-1), formula (a3-2), formula (a3-3) or formula (a3-4):

wherein L a4 , L a5 and L a6 each independently represent *—O— or *—O—(CH 2 ) k3 —CO—O— in which * represents a binding site to —CO— and k3 represents an integer of 1 to 7;
L a7 represents a single bond, *-L a8 -O—, *-L a8 -CO—O—, *-L a8 -CO—O-L a9 -CO—O—, or *-L a9 -O—CO-L a9 -O— in which * represents a binding site to a carbonyl group, L a8 and L a9 each represent a C1-C6 alkanediyl group;
R a18 , R a19 and R a20 each independently represent a hydrogen atom or a methyl group;
R a21 represents a C1-C4 aliphatic hydrocarbon group;
R a22 , R a23 and R a25 are independently in each occurrence a carboxyl group, a cyano group or a C1-C4 aliphatic hydrocarbon group;
R a24 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group in which a hydrogen atom can be replaced by a fluorine atom;
p1 represents an integer of 0 to 5;
q1 and r1 each independently represent an integer of 0 to 3; and
w1 represents an integer of 0 to 8.

11 . The resin according to claim 5 ,
which further comprises a structural unit having a hydroxy group.

12 . The resin according to claim 11 , wherein
the structural unit having a hydroxy group is represented by formula (a2-1):

in which L a3 represents an oxygen atom or *—O—(CH 2 ) k2 —CO—O— in which * represents a binding site to —CO—, and k2 represents an integer of 1 to 7;
R a14 represents a hydrogen atom or a methyl group;
R a15 and R a16 each independently represent a hydrogen atom, a methyl group or a hydroxy group; and
o1 represents an integer of 0 to 10.

13 . The resin according to claim 5 ,
which further comprises a structural unit having a fluorine atom, said structural unit being different from the structural unit derived from the compound represented by formula (I).

14 . A photoresist composition which comprises the resin according to claim 5 and an acid generator.

15 . The photoresist composition according to claim 14 , further comprising a resin which comprises a structural unit having an acid-labile group and no structural unit derived from the compound represented by formula (I), or a resin which comprises a structural unit having a fluorine atom and no structural unit derived from the compound represented by formula (I).

16 . The photoresist composition according to claim 15 , further comprising a resin which comprises a structural unit having a fluorine atom and no structural unit derived from the compound represented by formula (I).

17 . The photoresist composition according to claim 14 , wherein the acid generator is a salt represented by formula (B1):

wherein Q 1 and Q 2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group,
L b1 represents a C1-C24 divalent saturated hydrocarbon group where a methylene group can be replaced by an oxygen atom or a carbonyl group and where a hydrogen atom can be replaced by an fluorine atom or a hydroxy group,
Y represents a methyl group where a hydrogen atom can be replaced by a substituent or a C3-C18 alicyclic hydrocarbon group where a methylene group can be replaced by an oxygen atom, a sulfonyl group or a carbonyl group and where a hydrogen atom can be replaced by a substituent, and
Z + represents an organic cation.

18 . The photoresist composition according to claim 14 , further comprising a salt which generates an acid weaker in acidity than an acid generated from the acid generator.

19 . A process for producing a photoresist pattern comprising the following steps (1) to (5):
(1) a step of applying the photoresist composition according to claim 14 on a substrate, (2) a step of forming a composition film by drying the composition, (3) a step of exposing the composition film to radiation, (4) a step of baking the exposed composition film, and (5) a step of developing the baked composition film.

Assignees

• Sumitomo Chemical Co

Inventors

• Masuyama Tatsuro
• Suzuki Yuki
• Ichikawa Koji

Classifications

• C08F220/282

  and containing two or more oxygen atoms · CPC title

• C08F220/1811

  C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate · CPC title

• G03F7/0045

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

• C08F220/22

  Esters containing halogen · CPC title

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title