Pattern forming method, chemical amplification resist composition and resist film

Patent metadata

Field	Value
Publication number	US-9116437-B2
Application number	US-201013320150-A
Country	US
Kind code	B2
Filing date	Jun 14, 2010
Priority date	Jun 17, 2009
Publication date	Aug 25, 2015
Grant date	Aug 25, 2015

Abstract

A pattern forming method, including: (i) forming a film from a chemical amplification resist composition; (ii) exposing the film, so as to form an exposed film; and (iii) developing the exposed film by using a developer containing an organic solvent, wherein the chemical amplification resist composition contains: (A) a resin capable of decreasing a solubility of the resin (A) in the developer containing an organic solvent by an action of an acid; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; and (C) a basic, compound or ammonium salt compound whose basicity decreases upon irradiation with an actinic ray or radiation, and a resist composition used for the pattern forming method and a resist film formed from the resist composition are provided.

First claim

The invention claimed is:

1. A pattern forming method, comprising:
(i) forming a film from a chemical amplification resist composition;
(ii) pattern-wise exposing the film with far ultraviolet rays or EUV light using a mask or a reticle having a pattern, so as to form an exposed film having low exposure regions and high exposure regions; and
(iii) developing the exposed film by using a developer containing an organic solvent, wherein the chemical amplification resist composition contains:
(A) a resin (A) which contains an acid-decomposable group-containing repeating unit and which decreases its solubility in the developer containing an organic solvent by an action of an acid;
(B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; and
(C) a basic compound or ammonium salt compound whose basicity decreases upon irradiation with an actinic ray or radiation,

wherein the organic solvent contained in the developer is at least one kind of an organic solvent selected from the group consisting of a ketone-based solvent, an ester-based solvent, an amide-based solvent or an ether-based solvent,
and wherein the development is performed by dissolving the low exposure regions of the exposed film and forming the pattern of said high exposure regions.

2. The pattern forming method according to claim 1 ,
wherein the content of the organic solvent in the developer is from 90 to 100 mass % based on the entire amount of the developer.

3. The pattern forming method according to claim 1 ,
wherein the compound (C) is a basic compound having a basic functional group and a group capable of generating an acidic functional group upon irradiation with an actinic ray or radiation, or an ammonium salt compound having an ammonium group and a group capable of generating an acidic functional group upon irradiation with an actinic ray or radiation.

4. The pattern forming method according to claim 1 ,
wherein the compound (C) generates a compound represented by the following formula (PA-I), (PA-II) or (PA-III) upon irradiation with an actinic ray or radiation:
Q-A 1 -(X) n —B—R  (PA-I)

Q 1 -X 1 —NH—X 2 -Q 2   (PA-II)

Q 1 -X 1 —NH—X 2 -A 2 -(X 3 ) m —B-Q 3   (PA-III)

wherein in formula (PA-I),
A 1 represents a single bond or a divalent linking group;
Q represents —SO 3 H or —CO 2 H;
X represents —SO 2 — or —CO—;
n represents 0 or 1;
B represents a single bond, an oxygen atom or —N(Rx)-;
Rx represents a hydrogen atom or a monovalent organic group; and
R represents a monovalent organic group having a basic functional group, or a monovalent organic group having an ammonium group;
in formula (PA-II),
each of Q 1 and Q 2 independently represents a monovalent organic group, provided that either one of Q 1 and Q 2 has a basic functional group, Q 1 and Q 2 may combine to form a ring, and the ring formed may have a basic functional group; and
each of X 1 and X 2 independently represents —CO— or —SO 2 —; and
in formula (PA-III),
each of Q 1 and Q 3 independently represents a monovalent organic group, provided that either one of Q 1 and Q 3 has a basic functional group, Q 1 and Q 3 may combine to form a ring, and the ring formed may have a basic functional group;
each of X 1 , X 2 and X 3 independently represents —CO— or —SO 2 —;
A 2 represents a divalent linking group;
B represents a single bond, an oxygen atom or —N(Qx)-;
Qx represents a hydrogen atom or a monovalent organic group;
when B is —N(Qx)-, Q 3 and Qx may combine to form a ring; and
m represents 0 or 1.

5. The pattern forming method according to claim 4 ,
wherein the compound (C) generates a compound represented by formula (PA-II) or (PA-III).

6. The pattern forming method according to claim 1 , further comprising:
(iv) performing rinsing by using a rinsing solution.

7. The pattern forming method according to claim 6 ,
wherein the rinsing solution is a rinsing solution containing at least one kind of an organic solvent selected from the group consisting of a hydrocarbon-based solvent, a ketone-based solvent, an ester-based solvent, an alcohol-based solvent, an amide-based solvent and an ether-based solvent.

8. The pattern forming method according to claim 1 , further comprising:
(vi) developing the film by using an aqueous alkali developer.

9. The pattern forming method according to claim 1 ,
wherein the exposure is immersion exposure.

10. A chemical amplification resist composition that is used in the pattern forming method claimed in claim 1 .

11. A resist film formed from the chemical amplification resist composition claimed in claim 10 .

12. The pattern forming method according to claim 1 , wherein the resist composition further contains a hydrophobic resin.

13. The pattern forming method according to claim 1 , wherein the actinic ray or radiation is ArF excimer laser.

14. The pattern forming method according to claim 1 , wherein the acid-decomposable group-containing repeating unit in the resin (A) is represented by formula (AI):

wherein, in the formula (AI), Xa 1 represents a hydrogen atom, a methyl group which may have a substituent, or a group represented by —CH 2 —R 9 where R 9 represents a hydroxyl group or a monovalent organic group; T represents a single bond or a divalent linking group; and each of Rx 1 to Rx 3 independently represents an alkyl group or a cycloalkyl group with the proviso that two members out of Rx 1 to Rx 3 may combine to form a cycloalkyl group.

15. The pattern forming method according to claim 14 , wherein the acid-decomposable group-containing repeating unit includes a repeating unit represented by formulae (1) or (2):

wherein, in formulae (1) and (2), each of R 1 and R 3 independently represents a hydrogen atom, a methyl group which may have a substituent, or a group represented by —CH 2 —R 9 where R 9 represents a hydroxyl group or a monovalent organic group; each of R 2 , R 4 , R 5 and R 6 independently represents an alkyl group or a cycloalkyl group; and R represents an atomic group necessary for forming an alicyclic structure together with the carbon atom.

16. The pattern forming method according to claim 15 , wherein the acid-decomposable group-containing repeating unit includes repeating units represented by formulae (1) and (2).

17. The pattern forming method according to claim 15 , wherein the acid-decomposable group-containing repeating unit includes two kinds of the repeating unit represented by formula (1).

Assignees

• Enomoto Yuichiro
• Kamimura Sou
• Tarutani Shinji
• Fujifilm Corp

Inventors

• Enomoto Yuichiro
• Kamimura Sou
• Tarutani Shinji

Classifications

• G03F7/0397

  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

• G03F7/2041

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

• G03F7/0046

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

• G03F7/325 Primary

  Non-aqueous compositions · CPC title