Chemical amplification resist composition, resist film using the same, resist-coated mask blank, method of forming photomask and pattern, and method of manufacturing electronic device and electronic device

Patent metadata

Field	Value
Publication number	US-10139727-B2
Application number	US-201414540454-A
Country	US
Kind code	B2
Filing date	Nov 13, 2014
Priority date	May 21, 2012
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

A chemical amplification resist composition according to the present invention includes (A) a compound including a triarylsulfonium cation having one or more fluorine atoms and capable of generating an acid with a volume of 240 Å3 or higher by irradiation of active rays or radiation; and (B) a compound including a phenolic hydroxyl group.

First claim

What is claimed is:

1. A chemical amplification resist composition comprising:
(A) a compound including a triarylsulfonium cation having two or more fluorine atoms and capable of generating an acid with a volume of 240 Å 3 or higher by irradiation of active rays or radiation;
(B) a compound including a phenolic hydroxyl group; and
(C) an acid crosslinking compound,
wherein benzene rings configuring at least two aryl groups from the three aryl groups in the triarylsulfonium cation of the compound (A) each independently is directly bonded to at least one fluorine atom, and
the compound (B) is a resin having a weight average molecular weight of 2,000 or more.

2. The chemical amplification resist composition according to claim 1 , wherein the compound (A) is a compound including a triarylsulfonium cation having three or more fluorine atoms.

3. The chemical amplification resist composition according to claim 2 , wherein each of the three aryl groups in the triarylsulfonium cation of compound (A) includes one or more fluorine atoms.

4. The chemical amplification resist composition according to claim 1 , wherein the compound (B) is a resin in which solubility with respect to an alkali developer increases due to the action of an acid.

5. The chemical amplification resist composition according to claim 1 , wherein the compound (C) is a compound having two or more of a hydroxymethyl group or an alkoxymethyl group in the molecule.

6. The chemical amplification resist composition according to claim 1 , wherein the compound (B) is a resin including a repeating unit represented by the following Formula (1),

wherein, in Formula 1, R 11 represents a hydrogen atom, a methyl group or a halogen atom,
B 1 represents a single bond or a divalent linking group,
Ar represents an aromatic ring, and
m1 represents an integer of 1 or more.

7. The chemical amplification resist composition according to claim 1 , wherein the composition is a chemical amplification resist composition for electron beam or extreme ultraviolet light exposure.

8. A resist film formed of the chemical amplification resist composition according to claim 1 .

9. A resist-coated mask blank coated with the resist film according to claim 8 .

10. A photomask obtained by exposing and developing the resist-coated mask blank according to claim 9 .

11. A method for forming a pattern comprising exposing the resist-coated mask blank according to claim 9 , and developing the exposed mask blank.

12. A method of forming a pattern comprising exposing the resist film according to claim 8 and developing the exposed film.

13. A method of manufacturing an electronic device, including the method of forming a pattern according to claim 12 .

14. The chemical amplification resist composition according to claim 1 ,
wherein the compound (A) is represented by the following Formula (1),

wherein, in Formula (1),
R a1 represents a substituent,
n 1 represents an integer of 0 to 5,
n 2 represents an integer of 1 to 5,
when n 2 represents 1, R a2 represents a fluorine atom,
when n 2 represents an integer of 2 to 5, R a2 represents a substituent, a fluorine atom, or a group including one or more fluorine atoms, and at least one of R a2 's represents a fluorine atom,
n 3 represents an integer of 1 to 5,
when n 3 represents 1, R a3 represents a fluorine atom,
when n 3 represents an integer of 2 to 5, R a3 represents a substituent, a fluorine atom, or a group including one or more fluorine atoms, and at least one of R a3 's represents a fluorine atom,
R a1 and R a2 may be linked with each other to form a ring, and
X − represents an organic anion.

15. The chemical amplification resist composition according to claim 1 ,
wherein the compound (A) includes a sulfonate anion represented by the following Formula (SA1),

wherein, in Formula (SA1),
Ar represents an aryl group, and may further have a substituent other than the sulfonate anion and -(D-B) group,
n represents an integer of 0 or more,
D represents a single bond or a divalent linking group, and
B represents a hydrocarbon group.

16. The chemical amplification resist composition according to claim 1 further comprising a photodegradable basic compound.

17. The chemical amplification resist composition according to claim 1 ,
wherein the compound (A) includes at least one of the following compounds:

18. The chemical amplification resist composition according to claim 1 ,
wherein the compound (A) includes the following compound:

Assignees

• Fujifilm Corp

Inventors

• Tsuchimura Tomotaka
• Takahashi Koutarou

Classifications

• G03F7/0397 Primary

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

• G03F7/0382 Primary

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title

• G03F7/0046

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

• G03F7/0045

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

• G03F1/56

  Organic absorbers, e.g. of photo-resists · CPC title