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

Patent metadata

Field	Value
Publication number	US-9760003-B2
Application number	US-201113642751-A
Country	US
Kind code	B2
Filing date	May 20, 2011
Priority date	May 25, 2010
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

Provided is a method of forming a pattern and an actinic-ray- or radiation-sensitive resin composition that excels in the limiting resolving power, roughness characteristics, exposure latitude (EL) and bridge defect performance. The method of forming a pattern includes (1) forming an actinic-ray- or radiation-sensitive resin composition into a film, (2) exposing the film to light, and (3) developing the exposed film with a developer containing an organic solvent. The actinic-ray- or radiation-sensitive resin composition contains (A) a resin containing a repeating unit with a structural moiety that is configured to decompose when exposed to actinic rays or radiation to thereby generate an acid, and (B) a solvent.

First claim

The invention claimed is:

1. A method of forming a negative pattern, comprising:
(1) forming an actinic-ray- or radiation-sensitive resin composition into a film,
(2) exposing the film to light, and
(3) developing the exposed film with a developer containing a polar solvent as an organic solvent,
the actinic-ray- or radiation-sensitive resin composition comprising:
(A) a resin containing a repeating unit with a structural moiety that is configured to decompose when exposed to actinic rays or radiation to thereby generate an acid of any general formulae (III) to (VII) below, and
(B) a solvent,
wherein said resin (A) further contains a repeating unit with an acid decomposable group, and
wherein an amount of the organic solvent used in the developer is in the range of 80 to 100 mass %,

in which

each of R 04 , R 05 and R 07 to R 09 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group,
R 06 represents a cyano group, a carboxyl group, —CO—OR 25 or —CO—N(R 26 )(R 27 ), provided that when R 06 is —CO—N(R 26 )(R 27 ), R 26 and R 27 may be bonded to each other to thereby form a ring in cooperation with N atom,
each of X 1 to X 3 independently represents a single bond, or an arylene group, an alkylene group, a cycloalkylene group, —O—, —SO 2 —, —CO—, —N(R 33 )— or a bivalent connecting group composed of a combination of these,
R 25 represents an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group or an aralkyl group,
each of R 26 , R 27 and R 33 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an aryl group or an aralkyl group,
W represents —O—, —S— or a methylene group,
l is 0 or 1, and
A represents a structural moiety that is configured to decompose when exposed to actinic rays or radiation to thereby generate an acid, wherein the structural moiety has a nonionic structure.

2. The method according to claim 1 , wherein the structural moiety has an oxime structure.

3. The method according to claim 1 , wherein the structural moiety has a structure that generates an acid group on a side chain of the resin when exposed to actinic rays or radiation.

4. The method according to claim 1 , wherein said acid decomposable group is a group that is configured to decompose when acted on by an acid to thereby produce an alcoholic hydroxyl group.

5. The method according to claim 1 , wherein said repeating unit with an acid decomposable group is represented by general formula (AI) below,

in which
Xa 1 represents a hydrogen atom, a methyl group, or a group represented by —CH 2 —R 9 in which R 9 represents a hydroxyl group or a monovalent organic group,
T represents a single bond or a bivalent connecting group, and
each of Rx 1 to Rx 3 independently represents a linear or branched alkyl group or a monocyclic or polycyclic cycloalkyl group, provided that at least two of Rx 1 to Rx 3 may be bonded to each other to thereby form a monocyclic or polycyclic cycloalkyl group.

6. The method according to claim 1 , wherein the composition further comprises a hydrophobic resin.

7. The method according to claim 6 , wherein a content of the hydrophobic resin in the composition based on total solids thereof is in the range of 0.01 to 10 mass %.

8. The method according to claim 6 , wherein the hydrophobic resin contains at least one of fluorine atom and silicon atom.

9. The method according to claim 1 , wherein the exposure is performed through an immersion liquid.

10. The method according to claim 1 , wherein the developer containing a polar solvent as an organic solvent is a developer containing an ester solvent.

11. The method according to claim 10 , wherein the ester solvent is a butyl acetate.

12. The method according to claim 1 , further comprising:
(4) rinsing the developed film with a rinse liquid containing an organic solvent.

13. The method according to claim 1 , wherein said resin (A) further contains a repeating unit containing a lactone structure.

14. The method according to claim 13 , wherein said repeating unit containing a lactone structure is represented by the following general formula (AII′):

wherein,
Rb 0 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms, and
V represents any of the groups of general formulae (LC1-1) to (LC1-17),

wherein,
Rb 2 represents a substituent, and
n2 is an integer of 0 to 2.

15. The method according to claim 1 , wherein said resin (A) further contains a repeating unit containing a hydroxyl group or a cyano group, represented by any of general formulae (Alla) to (AIId) below,

wherein,
R 1 C represents a hydrogen atom, a methyl group, a trifluoromethyl group or a hydroxymethyl group, and
each of R 2C to R 4C independently represents a hydrogen atom, a hydroxyl group or a cyano group, with the proviso that at least one of the R 2C to R 4C represents a hydroxy group or a cyano group.

16. The method according to claim 1 , wherein the content ratio of the resin based on the total solid content of the whole composition is in the range of 60 to 95 mass %.

17. A method of forming a negative pattern, comprising:
(1) forming an actinic-ray- or radiation-sensitive resin composition into a film,
(2) exposing the film to light, and
(3) developing the exposed film with a developer containing a polar solvent as an organic solvent, wherein said polar solvent contains at least an ester solvent or a ketone solvent,
the actinic-ray- or radiation-sensitive resin composition comprising:
(A) a resin containing a repeating unit with a structural moiety that is configured to decompose when exposed to actinic rays or radiation to thereby generate an acid of any general formulae (III) to (VII) below, and
(B) a solvent,
wherein said resin (A) further contains a repeating unit with an acid decomposable group, and
wherein an amount of the organic solvent used in the developer is in the range of 80 to 100 mass %,

in which

each of R 04 , R 05 and R 07 to R 09 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group,
R 06 represents a cyano group, a carboxyl group, —CO—OR 25 or —CO—N(R 26 )(R 27 ), provided that when R 06 is —CO—N(R 26 )(R 27 ), R 26 and R 27 may be bonded to each other to thereby form a ring in cooperation with N atom,
each of X 1 to X 3 independently represents a single bond, or an arylene group, an alkylene group, a cycloalkylene group, —O—, —SO 2 —, —CO—, —N(R 33 )—

Assignees

• Iwato Kaoru
• Takahashi Hidenori
• Hirano Shuji
• Kamimura Sou
• Kato Keita
• Fujifilm Corp

Inventors

• Iwato Kaoru
• Takahashi Hidenori
• Hirano Shuji
• Kamimura Sou
• Kato Keita

Classifications

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• Y10T428/24

  Structurally defined web or sheet [e.g., overall dimension, etc.] · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title

• G03F7/0758

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