Pattern-forming method, electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition, resist film, manufacturing method of electronic device using them and electronic device

Patent metadata

Field	Value
Publication number	US-9470980-B2
Application number	US-201414228894-A
Country	US
Kind code	B2
Filing date	Mar 28, 2014
Priority date	Sep 30, 2011
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

A pattern-forming method includes in this order: step ( 1 ) of forming a film with an electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition that contains (A) a resin having an acid-decomposable repeating unit and capable of decreasing a solubility of the resin (A) in a developer containing an organic solvent by an action of an acid, (B) a compound capable of generating an acid upon irradiation with an electron beam or extreme ultraviolet radiation, (C) a resin having one or more groups selected from the specific group as defined in the specification and (D) a solvent; step ( 2 ) of exposing the film with an electron beam or extreme ultraviolet radiation; and step ( 4 ) of developing the film with a developer containing an organic solvent after the exposing to form a negative pattern.

First claim

The invention claimed is:

1. A pattern-forming method, comprising in this order:
step (1) of forming a film with an electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition that contains (A) a resin having an acid-decomposable repeating unit and capable of decreasing a solubility of the resin (A) in a developer containing an organic solvent by an action of an acid, (B) a compound capable of generating an acid upon irradiation with an electron beam or extreme ultraviolet radiation, (C) a resin having one or more groups selected from the group consisting of an alkyl group having 6 or more carbon atoms, a cycloalkyl group having 6 or more carbon atoms, an aryl group having 9 or more carbon atoms, an aralkyl group having 10 or more carbon atoms, an aromatic ring group substituted with at least one alkyl group having 3 or more carbon atoms and an aromatic ring group substituted with at least one cycloalkyl group having 5 or more carbon atoms, and wherein the resin (C) contains no fluorine or silicon atoms, and (D) a solvent;
step (2) of exposing the film with an electron beam or extreme ultraviolet radiation; and
step (4) of developing the film with a developer containing an organic solvent after the exposing to form a negative pattern.

2. The pattern-forming method according to claim 1 ,
wherein the resin (C) contains a repeating unit represented by any one of the following formulae (C-Ia) to (C-Id):

wherein each of R 10 and R 11 independently represents a hydrogen atom or an alkyl group;
each of W 3 , W 5 and W 6 independently represents an organic group having one or more groups selected from the group consisting of a group having an alkyl group having 6 or more carbon atoms, a cycloalkyl group having 6 or more carbon atoms, an aryl group having 9 or more carbon atoms and an aralkyl group having 10 or more carbon atoms;
W 4 represents an organic group having one or more groups selected from the group consisting of a group having an alkyl group having 3 or more carbon atoms and a cycloalkyl group having 5 or more carbon atoms;
Ar 11 represents an (r+1)-valent aromatic ring group; and
r represents an integer of 1 to 10.

3. The pattern-forming method according to claim 2 ,
wherein the resin (C) further contains a repeating unit having an aromatic ring group other than the repeating unit represented by any one of the formulae (C-Ia) to (C-Id).

4. The pattern-forming method according to claim 1 ,
wherein the resin (C) contains a repeating unit represented by the following formula (C-II):

wherein R 12 represents a hydrogen atom or a methyl group;
W 7 represents an organic group having one or more groups selected from the group consisting of an alkyl group having 3 or more carbon atoms and a cycloalkyl group having 5 or more carbon atoms;
L 1 represents a single bond or a —COOL 2 - group;
L 2 represents a single bond or an alkylene group; and
n represents an integer of 1 to 5.

5. The pattern-forming method according to claim 4 ,
wherein in formula (C-II), W 7 represents an alkyl group having 3 or more carbon atoms or a cycloalkyl group having 5 or more carbon atoms.

6. The pattern-forming method according to claim 1 ,
wherein a content of the acid-decomposable repeating unit in the resin (C) is 5 mol% or less to all repeating units in the resin (C).

7. The pattern-forming method according to claim 1 ,
wherein the resin (A) has one or more groups selected from the group consisting of a hydroxyl group, a cyano group, a lactone group, a carboxylic acid group, a sulfonic acid group, an amido group, a sulfonamido group, an ammonium group, a sulfonium group and a group obtained by combining two or more of these groups.

8. The pattern-forming method according to claim 1 ,
wherein a content of the compound (B) is 21% by mass to 70% by mass on the basis of all solids content of the composition.

9. The pattern-forming method according to claim 1 , which is a method for forming a semiconductor ultrafine circuit.

10. The pattern-forming method according to claim 1 ,
wherein a content of the resin (C) in the composition is 0.01% by mass to 10% by mass on a basis of all solid contents in the composition.

11. The pattern-forming method according to claim 1 ,
wherein a content of the resin (C) in the composition is 0.05% by mass to 8% by mass on a basis of all solid contents in the composition.

12. The pattern-forming method according to claim 1 ,
wherein a content of the resin (C) in the composition is 0.1% by mass to 5% by mass on a basis of all solid contents in the composition.

13. A manufacturing method of an electronic device, comprising:
the pattern-forming method according to claim 1 .

14. An electronic device, which is manufactured by the manufacturing method of an electronic device according to claim 13 .

15. A pattern-forming method, comprising in this order:
step (1) of forming a film with an electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition that contains (A) a resin having an acid-decomposable repeating unit and capable of decreasing a solubility of the resin (A) in a developer containing an organic solvent by an action of an acid, (B) a compound capable of generating an acid upon irradiation with an electron beam or extreme ultraviolet radiation, (C) a resin containing a repeating unit represented by the following formula (C-II):

wherein R 12 represents a hydrogen atom, a methyl group, a trifluoromethyl group or a fluorine atom;
W 7 represents an organic group having one or more groups selected from the group consisting of a group having a fluorine atom, a group having a silicon atom, an alkyl group having 3 or more carbon atoms and a cycloalkyl group having 5 or more carbon atoms;
L 1 represents a single bond or a —COOL 2 - group;
L 2 represents a single bond or an alkylene group; and
n represents an integer of 1 to 5,

and wherein the resin (C) contains a repeating unit, other than the repeating unit represented by formula (C-II), which contains a plurality of aromatic rings, represented by formula (II) or formula (c1):

wherein each of R 51 , R 52 and R 53 independently represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group, provided that R 52 may be bonded to Ar 5 to form a ring, and R 52 in that case represents a single bond or an alkylene group; X 5 represents a single bond, —COO—or —CONR 64 —, and R 64 represents a hydrogen atom or an alkyl group; L 5 represents a single bond or an alkylene group; Ar 5 represents a monovalent aromatic ring group, and represents a divalent aromatic ring group when bonded to R 52 to form a ring,

wherein R 3 represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group or a nitro group; Y represents a single bond or a divalent linking group; Z represents a single bond or a divalent linking group; Ar represents an aromatic ring group; and p represents an integer

Assignees

• Fujifilm Corp

Inventors

• Inoue Naoki
• Takizawa Hiroo
• Hirano Shuji
• Tsubaki Hideaki

Classifications

• C08F212/24 Primary

  Phenols or alcohols · CPC title

• G03F7/2041

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

• C08F12/24

  Phenols or alcohols · CPC title

• G03F7/0046

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

• G03F7/0758

  with silicon- containing groups in the side chains · CPC title