Resist composition and method for forming resist pattern

Patent metadata

Field	Value
Publication number	US-10437147-B2
Application number	US-201715471428-A
Country	US
Kind code	B2
Filing date	Mar 28, 2017
Priority date	Mar 31, 2016
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

A resist composition which includes a polymer compound including a structural unit which is derived from an acrylic ester in which the hydrogen atom bonded to an α-position carbon atom may be substituted with a substituent and which has a lactone-containing cyclic group containing other electron withdrawing groups such as a cyano group at a side chain terminal, and a compound whose a conjugate acid has an acid dissociation constant (pKa) of less than 3.

First claim

What is claimed is:

1. A resist composition which generates an acid upon exposure and whose solubility in a developing solution changes under the action of the acid, the resist composition comprising:
a base material component (A) whose solubility in the developing solution changes under the action of the acid and which contains a polymer compound (A1) consisting of a structural unit (a0) represented by the following general formula (a0-1) and a structural unit (a1) containing an acid-decomposable group which increases the polarity under action of the acid;
an acid generator component (B) which generates acid upon exposure;
an organic solvent component (S); and
an acid diffusion control agent component (D) which contains a compound (D1) whose a conjugate acid has an acid dissociation constant (pKa) of less than 3, provided that the compound (D1) is excluded from the acid generator component (B):

wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms;
Va 0 is a divalent hydrocarbon group which may have a substituent;
n a0 is an integer of 0 to 2;
Ra 1 and Ra 2 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, or an alkylthio group, or Ra 1 and Ra 2 may be bonded to each other so as to form an alkylene group having 1 to 6 carbon atoms, which may contain an oxygen atom or a sulfur atom, an ether bond, or a thioether bond;
Ra′ 01 is a halogen atom, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydroxyalkyl group having 1 to 6 carbon atoms, of which the hydroxy group may be protected by a protective group and which may have a halogen atom, a carboxy group which may form a salt, or a substituted oxycarbonyl group;
p 0 is an integer of 0 to 8, and in a case where two or more Ra′ 01 's are present, the plural Ra′ 01 's may be the same as or different from each other;
X is a cyano group; and
q 0 is an integer of 1 to 9, and in a case where two or more X's are present, the plural X's may be the same as or different from each other.

2. The resist composition according to claim 1 , wherein the compound (D1) is a compound represented by the following general formula (d1):

wherein Rd 1 is a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent, m is an integer of 1 or more, and M m+ represents an m-valent organic cation.

3. The resist composition according to claim 1 , wherein the content of the compound (D1) is 0.5 to 10 parts by mass with respect to 100 parts by mass of the base material component (A).

4. The resist composition according to claim 2 , wherein Rd 1 is an aromatic ring including a hydroxybenzoic acid skeleton and at least one hydrogen atom of the aromatic ring is substituted with a group having a halogen atom, or a linear alkyl group and at least one hydrogen atom of the alkyl group is substituted with a group having a halogen atom.

5. The resist composition according to claim 2 , wherein Rd 1 is an aromatic ring including a hydroxybenzoic acid skeleton and at least one hydrogen atom of the aromatic ring is substituted with a group having a halogen atom.

6. A method for forming a resist pattern, comprising:
applying the resist composition according to claim 1 on a support to form a resist film;
exposing the resist film; and
developing the exposed resist film to form a resist pattern.

7. A resist composition which generates an acid upon exposure and whose solubility in a developing solution changes under the action of the acid,
the resist composition comprising:
a base material component (A) whose solubility in the developing solution changes under the action of the acid and which contains a polymer compound (A1) consisting of a structural unit (a0) represented by the following general formula (a0-1), a structural unit (a1) containing an acid-decomposable group, which increases the polarity under the action of the acid, and a structural unit (a2) containing a lactone-containing cyclic group, a —SO 2 — containing cyclic group or a carbonate-containing cyclic group;
an acid generator component (B) which generates an acid upon exposure;
an organic solvent component (S); and
an acid diffusion control agent component (D) which contains a compound (D1) whose a conjugate acid has an acid dissociation constant (pKa) of less than 3, provided that the compound (D1) is excluded from the acid generator component (B):

wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms;
Va 0 is a divalent hydrocarbon group which may have a substituent;
n a0 is an integer of 0 to 2;
Ra 1 and Ra 2 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, or an alkylthio group, or Ra 1 and Ra 2 may be bonded to each other so as to form an alkylene group having 1 to 6 carbon atoms, which may contain an oxygen atom or a sulfur atom, an ether bond, or a thioether bond;
Ra′ 01 is a halogen atom, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydroxyalkyl group having 1 to 6 carbon atoms, of which the hydroxy group may be protected by a protective group and which may have a halogen atom, a carboxy group which may form a salt, or a substituted oxycarbonyl group;
p 0 is an integer of 0 to 8, and in a case where two or more Ra′ 01 's are present, the plural Ra′ 01 's may be the same as or different from each other;
X is a cyano group; and
q 0 is an integer of 1 to 9, and in a case where two or more X's are present, the plural X's may be the same as or different from each other.

8. The resist composition according to claim 7 , wherein the compound (D1) is a compound represented by the following general formula (d1):

wherein Rd 1 is a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent, or a chain-like alkenyl group which may have a substituent, m is an integer of 1 or more, and M m+ represents an m-valent organic cation.

9. The resist composition according to claim 7 , wherein the content of the compound (D1) is 0.5 to 10 parts by mass with respect to 100 parts by mass of the base material component (A).

10. The resist composition according to claim 8 , wherein Rd 1 is an aromatic ring including a hydroxybenzoic acid skeleton and at least one hydrogen atom of the aromatic ring is substituted with a group having a halogen atom, or a linear alkyl group and at least one hydrogen atom of the alkyl group is substituted with a group having a halogen atom.

11. The resist composition according to claim 8 , wherein Rd 1 is an aromatic ring including a hydroxybenzoic acid skeleton and at least one hydrogen atom of the aromatic ring is substituted with a group having a halogen atom.

12. A method for forming a resist pattern, comprising:
applying the resist composition according to claim 7 on a support to form a resist film;
exposing the resist film; and
developing t

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Nagamine Takashi
• Iwasawa Yuta

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• G03F7/091

  characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement · CPC title

• G03F7/0397

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

• G03F7/38

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

• G03F7/2041

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