Pattern forming method, actinic ray-sensitive or radiation-sensitive resin composition and resist film

Patent metadata

Field	Value
Publication number	US-10248019-B2
Application number	US-201213725483-A
Country	US
Kind code	B2
Filing date	Dec 21, 2012
Priority date	Jun 25, 2010
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

A pattern forming, method, includes: (i) forming a film from an actinic ray-sensitive or radiation-sensitive resin composition that contains (A) a compound capable of generating an acid upon irradiation with an actinic ray or radiation and decomposing by an action of an acid to decrease a solubility of the compound (A) for an organic solvent; (ii) exposing the film; and (iii) performing development by using a developer containing an organic solvent.

First claim

The invention claimed is:

1. A pattern forming method, comprising:
(i) forming a film from an actinic ray-sensitive or radiation-sensitive resin composition that contains (A) a compound capable of generating an acid upon irradiation with an actinic ray or radiation and decomposing by an action of an acid to decrease a solubility of the compound (A) for an organic solvent, said compound being capable of decomposing an acid-decomposable structure;
(ii) exposing the film; and
(iii) performing development by using a developer containing an organic solvent,
wherein the compound (A) is a compound represented by the following formula (II-4) or (II-5):

wherein each X + independently represents a counter cation;
Rf represents an alkyl group having at least one fluorine atom, a cycloalkyl group having at least one fluorine atom, or an aryl group having at least one fluorine atom;
each of Xf 1 and Xf 2 independently represents a fluorine atom or an alkyl group substituted with at least one fluorine atom;
each of R 11 , R 12 , R 21 and R 22 independently represents a hydrogen atom, a fluorine atom or an alkyl group, and when a plurality of R 11 's, R 12 's, R 21 's or R 22 's are present, each may be the same as or different from every others;
each L 1 in formula (II-4) represents a divalent linking group selected from the group consisting of —COO—, —OCO—, —CO—, —O—, —S—, —SO—, —SO 2 —, an alkylene group, a cycloalkylene group, an alkenylene group, and a linking group formed by combining a plurality of these members, provided that at least one of L 1 is —COO—, and when a plurality of L 1 's is present, each may be the same as or different from every other;
each L 2 in formula (II-5) represents a divalent linking group selected from the group consisting of —COO—, —OCO—, —CO—, —O—, —S—, —SO—, —SO 2 —, an alkylene group, a cycloalkylene group, an alkenylene group, and a linking group formed by combining a plurality of these members, and when a plurality of L 2 's are present, each may be the same as or different from every other;
each of Cy 1 and Cy 2 independently represents an alicyclic group, an aryl group or a heterocyclic group;
provided that at least one of Xf 1 , R 11 , R 12 , L 1 and Cy 1 is substituted with a group having a structure in which a moiety capable of decomposing by an action of an acid to produce an alcoholic hydroxyl group or a carboxyl group is protected with a leaving group capable of decomposing and leaving by an action of an acid; and that at least one of Xf 2 , R 21 , R 22 , L 2 , Cy 2 and Rf is substituted with a group having a structure in which a moiety capable of decomposing by an action of an acid to produce an alcoholic hydroxyl group or a carboxyl group is protected with a leaving group capable of decomposing and leaving by an action of an acid;
each of x1 and x2 independently represents an integer of 1 to 20;
each of y1 and y2 independently represents an integer of 0 to 10;
z1 represents an integer of 1 to 10; and
z2 represents an integer of 0 to 10;
wherein the moiety capable of decomposing by an action of an acid to produce a hydroxyl group or a carboxyl group is represented by at least one formula selected from the group consisting of the following formulas (I-1) and (I-5):

wherein
in formula (I-1), each R 1 independently represents a hydrogen atom or a monovalent organic group, and two R 1 's may combine with each other to form a ring; and
R 2 represents a monovalent organic group, and one R 1 and R 2 may combine with each other to form a ring;
in formula (I-5), each R 7 independently represents a hydrogen atom or a monovalent organic group, and R 7 's may combine with each other to form a ring; and
in formulae (I-1) and (I-5), * represents a bond.

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

3. The pattern forming method according to claim 1 ,
wherein exposure in the step (ii) is immersion exposure.

4. The pattern forming method according to claim 1 ,
wherein the developer containing an organic solvent is a developer containing at least one kind of an organic solvent selected from the group consisting of a ketone-based solvent, an ester-based solvent, an alcohol-based solvent, an amide-based solvent and an ether-based solvent.

5. The pattern forming method according to claim 1 ,
wherein the moiety capable of decomposing by an action of an acid to produce a hydroxyl group or a carboxyl group is represented by formula (I-1).

6. The pattern forming method according to claim 1 ,
wherein the resist composition further contains a resin including a repeating unit having a lactone structure and represented by the following formula (III):

wherein A represents an ester bond of the structure —COO—or an amido bond of the structure —CONH—;
each R 0 independently represents an alkylene group, a cycloalkylene group or a combination thereof;
each Z independently represents a single bond, an ether bond, an ester bond, an amide bond, a urethane bond of the structure

or a urea bond of the structure

wherein each R independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group;
R 8 represents a monovalent organic group having a lactone structure;
n represents an integer of from 1 to 5; and
R 7 represents a hydrogen atom, a halogen atom or an alkyl group.

7. The pattern forming method according to claim 1 ,
wherein the developer containing an organic solvent is butyl acetate.

8. A pattern forming method, comprising:
(i) forming a film from an actinic ray-sensitive or radiation-sensitive resin composition that contains (A) a compound capable of generating an acid upon irradiation with an actinic ray or radiation and decomposing by an action of an acid to decrease a solubility of the compound (A) for an organic solvent, said compound being capable of decomposing an acid-decomposable structure;
(ii) exposing the film; and
(iii) performing development by using a developer containing an organic solvent,
wherein the compound (A) is a compound represented by the following formula (II-4) or (II-5):

wherein each X + independently represents a counter cation;
Rf represents an alkyl group having at least one fluorine atom, a cycloalkyl group having at least one fluorine atom, or an aryl group having at least one fluorine atom;
each of Xf 1 and Xf 2 independently represents a fluorine atom or an alkyl group substituted with at least one fluorine atom;
each of R 11 , R 12 , R 21 and R 22 independently represents a hydrogen atom, a fluorine atom or an alkyl group, and when a plurality of R 11 's, R 12 's, R 21 's or R 22 's are present, each may be the same as or different from every others;
each L 1 in formula (II-4) represents

Assignees

• Fujifilm Corp

Inventors

• Kataoka Shohei
• Iwato Kaoru
• Fujii Kana
• Kamimura Sou
• Enomoto Yuichiro
• Kato Keita
• Yamaguchi Shuhei

Classifications

• C07C309/13

  containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton · CPC title

• G03F7/0046

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

• C07C309/04

  containing only one sulfo group · CPC title

• C07C309/06

  containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title