Resist composition and method of forming resist pattern

Patent metadata

Field	Value
Publication number	US-11150554-B2
Application number	US-201615766734-A
Country	US
Kind code	B2
Filing date	Oct 13, 2016
Priority date	Oct 16, 2015
Publication date	Oct 19, 2021
Grant date	Oct 19, 2021

Abstract

A resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) including at least one acid generator (B1) represented by general formula (b1) shown below, at least one acid generator (B2) represented by general formula (b2) shown below, and at least one acid generator (B3) represented by general formula (b3) shown below (wherein IV to R 3 each independently represents a cyclic group which may have a substituent, a chain alkyl group, or a chain alkenyl group; Y 1 represents a single bond or a divalent linking group containing an oxygen atom; M 1 + to M 3 + represents a monovalent organic cation; n represents an integer of 1 to 4; m represents an integer of 0 to 4; provided that, when m is 0, the carbon atom adjacent to the sulfur atom within R 2 has no fluorine atom bonded thereto).

R 1 —Y 1 —(CF 2 ) n —SO 3 − M 1 +   (b1)

R 2 —(CH 2 ) m —SO 3 − M 2 +   (b2)

R 3 —COO − M 3 +   (b3)

First claim

What is claimed is:

1. A resist composition comprising:
a base component (A) which exhibits changed solubility in a developing solution under action of acid, and
an acid-generator component (B) which generates acid upon exposure,
the acid-generator component (B) comprising at least one acid generator (B1) represented by general formula (b1-1), (b1-2) or (b1-3) shown below, at least one acid generator (B2) represented by formula (B2)-1 or (B2)-2 shown below, and at least one acid generator (B3) represented by general formula (b3) shown below:

wherein R″ 101 represents an aliphatic cyclic group which may have a substituent, a group represented by any one of formulae (r-hr-1) to (r-hr-6) shown below or a chain-like alkyl group which may have a substituent; R″ 102 represents an aliphatic cyclic group which may have a substituent, a lactone-containing cyclic group represented by any one of general formulae (a2-r-1) to (a2-r-7) shown below or an —SO 2 — containing cyclic group represented by any one of general formulae (a5-r-1) to (a5-r-4) shown below; R″ 103 represents an aromatic cyclic group which may have a substituent, an aliphatic cyclic group which may have a substituent or a chain-like alkenyl group which may have a substituent; V″ 101 represents a fluorinated alkylene group; L″101 represents —C(═O)— or —SO 2 —; v″ represents an integer of 0 to 3; q″ represents an integer of 1 to 20; n″ represents 0 or 1; and each M 1 + independently represents a monovalent organic cation:

wherein each Ra′ 21 independently represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxy group, —COOR″, —OC(═O)R″, a hydroxyalkyl group or a cyano group; R″ represents a hydrogen atom or an alkyl group; A″ represents an oxygen atom, a sulfur atom or an alkylene group of 1 to 5 carbon atoms which may contain an oxygen atom or a sulfur atom; n′ represents an integer of 0 to 2; and m′ represents 0 or 1;

wherein each Ra′ 51 independently represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxy group, —COOR″, —OC(═O)R″, a hydroxyalkyl group or a cyano group; R″ represents a hydrogen atom or an alkyl group; A″ represents an oxygen atom, a sulfur atom or an alkylene group of 1 to 5 carbon atoms which may contain an oxygen atom or a sulfur atom; and n′ represents an integer of 0 to 2
R 2 —COO − M 2 +   (b3)

wherein R 3 represents a cyclic group which may have a substituent, a chain alkyl group which may have a substituent, or a chain alkenyl group which may have a substituent; and M 3 + independently represents a monovalent organic cation.

2. The resist composition according to claim 1 , further comprising a photoreactive quencher component (D).

3. The resist composition according to claim 1 , wherein the base component (A) is a base component which exhibits increased solubility in a developing solution by the action of acid.

4. The resist composition according to claim 1 , further comprising a fluorine additive component (F) having a molecular weight of 1,000 or more.

5. A method of forming a resist pattern, comprising:
using a resist composition according to claim 1 to form a resist film on a substrate,
exposing the resist film, and
alkali developing the resist film to form a resist pattern.

6. A method of forming a resist pattern, comprising:
using a resist composition according to claim 1 to form a resist film on a substrate,
exposing the resist film, and
developing the resist film using a developing solution containing 80% or more of an organic solvent to form a resist pattern.

7. The resist composition according to claim 1 , wherein, in general formula (b3), R 3 represents an aromatic hydrocarbon group which may have a substituent, an aliphatic cyclic group which may have a substituent and a chain hydrocarbon group which may have a substituent,
the aromatic hydrocarbon group is a phenyl group or a naphthyl group,
the aliphatic cyclic group is a group in which one or more hydrogen atoms have been removed from adamantane, norbornane, isobornane, tricyclodecane or tetracyclododecane, and
the chain hydrocarbon group is a chain alkyl group having 1 to 10 carbon atoms.

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Nakamura Tsuyoshi
• Tanno Kazuishi
• Lee Junyeob

Classifications

• G03F7/0325

  the binders being polysaccharides, e.g. cellulose · CPC title

• G03F7/0045 Primary

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

• G03F7/30

  Imagewise removal using liquid means · CPC title

• G03F7/2041

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

• G03F7/0382 Primary

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