Pattern forming method and resist composition

Patent metadata

Field	Value
Publication number	US-10126653-B2
Application number	US-201113580921-A
Country	US
Kind code	B2
Filing date	Feb 24, 2011
Priority date	Feb 26, 2010
Publication date	Nov 13, 2018
Grant date	Nov 13, 2018

Abstract

Provided is a method of forming a pattern, ensuring excellent sensitivity, limiting resolving power, roughness characteristic, exposure latitude (EL), dependence on post-exposure bake (PEB) temperature and focus latitude (depth of focus DOF), and a resist composition for use in the method. The method comprises (A) forming a film from a resist composition comprising a resin containing a repeating unit containing a group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group, which resin thus when acted on by an acid decreases its solubility in a developer containing an organic solvent, (B) exposing the film to light, and (C) developing the exposed film using a developer containing an organic solvent.

First claim

The invention claimed is:

1. A method of forming a pattern, comprising:
(A) forming a film from a resist composition comprising a resin containing a repeating unit containing a group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group in the side chain of the resin, a compound (b) that generates an acid when exposed to actinic rays or radiation, and solvent, which resin when acted on by an acid decreases its solubility in a developer containing an organic solvent,
(B) exposing the film to light, and
(C) developing the exposed film using a developer containing an organic solvent,
wherein the pattern formed is a negative pattern,
wherein the repeating unit is represented by at least one selected from the group consisting of general formulae (I-1) to (I-10) below,
wherein the group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group is represented by at least one selected from the group consisting of general formulae (II-3) to (II-9) below,
wherein the organic solvent contained in the developer is an ester solvent, and
wherein the amount of the ester solvent as the organic solvent used in the developer is in the range of 80 to 100 mass % based on a whole amount of the developer,

in the general formulae (I-1) to (I-10),
Ra, or each of Ra's independently, represents a hydrogen atom, an alkyl group or any of groups of the formula —CH 2 —O—Ra2 in which Ra2 represents a hydrogen atom, an alkyl group or an acyl group,
R 1 represents a (n+1)-valent organic group,
R 2 , when m≥2 each of R 2 s independently, represents a single bond or a (n+1)-valent organic group,
OP, or each of OPs independently, represents the group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group, provided that when n≥2 and/or m≥2, two or more OPs may be bonded to each other to thereby form a ring,
W represents a methylene group, an oxygen atom or a sulfur atom,
each of n and m is an integer of 1 or greater,
1 is an integer of 0 or greater,
L 1 represents a connecting group of the formula —COO—, —OCO—, —CONH—, —O—, —Ar—, —SO 3 — or —SO 2 NH—, the Ar representing a bivalent aromatic ring group,
each of R's independently represents a hydrogen atom or an alkyl group,
R 0 represents a hydrogen atom or an organic group,
L 3 represents a (m+2)-valent connecting group,
R L , when m≥2 each of R L s independently, represents a (n+1)-valent connecting group,
R S , when p≥2 each of R S s independently, represents a substituent, provided that when p≥2, two or more R Ss may be bonded to each other to thereby form a ring, and
p is an integer of 0 to 3,

in the general formulae (II-3) to (II-9),
R 3 , represents a hydrogen atom or a monovalent organic group,
R 4 , or each of R 4 s independently, represents a monovalent organic group, provided that at least two R 4 s may be bonded to each other to thereby form a ring and that R 3 and R 4 may be bonded to each other to thereby form a ring,
each of R 5 s independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or an alkynyl group, provided that at least two R 5 s may be bonded to each other to thereby form a ring and that when one or two of three R 5 s are a hydrogen atom, at least one of the rest of R 5 s represents an aryl group, an alkenyl group or an alkynyl group, and
each of R 6 s independently represents a hydrogen atom or a monovalent organic group, provided that R 6 s may be bonded to each other to thereby form a ring; and
wherein the solvent contained in the resist composition is different from the organic solvent contained in the developer.

2. The method of forming a pattern according to claim 1 , wherein the repeating unit is any of those represented by general formula (III) below:

in which
R 1 represents a (n+1)-valent organic group,
Ra represents a hydrogen atom, an alkyl group or any of groups of the formula —CH 2 —O—Ra2 in which Ra2 represents a hydrogen atom, an alkyl group or an acyl group,
each of R 3 s independently represents a hydrogen atom or a monovalent organic group, provided that R 3 s may be bonded to each other to thereby form a ring,
R 4 , when n≥2 each of R 4 s independently, represents a monovalent organic group, provided that R 4 s may be bonded to each other to thereby form a ring and that R 3 and R 4 may be bonded to each other to thereby form a ring, and
n is an integer of 1 or greater.

3. The method of forming a pattern according to claim 2 , wherein R 1 represents a nonaromatic hydrocarbon group.

4. The method of forming a pattern according to claim 3 , wherein R 1 represents an alicyclic hydrocarbon group.

5. The method of forming a pattern according to claim 1 , wherein the resin further contains a repeating unit containing an alcoholic hydroxyl group.

6. The method of forming a pattern according to claim 1 , wherein the resin further contains a repeating unit containing a cyano group.

7. The method of forming a pattern according to claim 1 , wherein the resin further contains a repeating unit containing a group that is decomposed when acted on by an acid to thereby produce a carboxyl group.

8. The method of forming a pattern according to claim 1 , the resin comprising a repeating unit containing a partial structure represented by the formula (D-1) below:

in the formula,
L D1 represents a single bond or a bivalent connecting group,
each of R D s independently represents a hydrogen atom, an alkyl group or a cycloalkyl group provided that at least two of three R D s may be bonded to each other to thereby form a ring,
X D1 represents a single bond or a connecting group having 1 or more carbon atoms, provided that L D1 , R D and X D1 may be bonded to each other to thereby form a ring, and provided that at least one of L D1 , R D and X D1 may be bonded to a carbon atom as a constituent of the principal chain of a polymer to thereby form a ring, and
each of R D1 s independently represents a hydrogen atom, an alkyl group or a cycloalkyl group, two R D1 s may be bonded to each other to thereby form a ring.

9. The method of forming a pattern according to claim 1 , wherein the group that is decomposed when acted on by an acid to thereby produce an alcoholic hydroxyl group is represented by at least one selected from the group consisting of general formulae (II-3) to (II-4) above.

10. The method of forming a pattern according to claim 1 , wherein the resin further contains a repeating unit containing a lactone structure.

11. The method of forming a pattern according to claim 1 , wherein the resist composition further comprises a hydrophobic resin (e).

12. The method of forming a pattern according to claim 11 , wherein the hydrophobic resin (e) contains at least one of a fluorine atom and a silicon atom.

13. The method of forming a pattern according to claim

Assignees

• Iwato Kaoru
• Kataoka Shohei
• Tarutani Shinji
• Kamimura Sou
• Kato Keita
• Enomoto Yuichiro
• Mizutani Kazuyoshi
• Tsuchihashi Toru
• Fujii Kana
• Fujifilm Corp

Inventors

• Iwato Kaoru
• Kataoka Shohei
• Tarutani Shinji
• Kamimura Sou
• Kato Keita
• Enomoto Yuichiro
• Mizutani Kazuyoshi
• Tsuchihashi Toru
• Fujii Kana

Classifications

• Y10T428/24479

  including variation in thickness · CPC title

• G03F7/0757

  Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence) · CPC title

• G03F7/0046

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

• G03F7/38

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

• G03F7/0045 Primary

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