Pattern forming method and actinic ray-sensitive or radiation-sensitive resin composition for use in the method

Patent metadata

Field	Value
Publication number	US-9250519-B2
Application number	US-201414580686-A
Country	US
Kind code	B2
Filing date	Dec 23, 2014
Priority date	Jul 26, 2012
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

The pattern forming method of the present invention includes: (i) forming a film including an actinic ray-sensitive or radiation-sensitive resin composition containing a compound (A) represented by General Formula (I) shown below; a resin (P) capable of decreasing solubility with respect to a developer including organic solvent by the action of an acid; and a compound (B) capable of generating an acid by irradiation of actinic rays or radiation; (ii) irradiating the film with actinic rays or radiation; (iii) developing the film irradiated with the actinic rays or radiation using a developer including an organic solvent.
[Chem. 1]

R N -A − X +   (I)

First claim

What is claimed is:

1. A pattern forming method comprising:
(i) forming a film including an actinic ray-sensitive or radiation-sensitive resin composition containing a compound (A) represented by General Formula (I) shown below;
a resin (P) capable of decreasing solubility with respect to a developer including an organic solvent by action of an acid; and
a compound (B) capable of generating an acid by irradiation of actinic rays or radiation;
(ii) irradiating the film with actinic rays or radiation;
(iii) developing the film irradiated with the actinic rays or radiation using a developer including an organic solvent;
R N -A − X +   (I)

wherein in general formula (I),
R N represents a monovalent basic compound residue containing at least one nitrogen atom and an alkyl group substituted with at least one fluorine atom;
A − represents any of general formula (a-1) to (a-3) shown below:

Ar represents an aryl group or a heteroaryl group;
Rf 1 and Rf 2 each independently represent a fluorine atom or an alkyl group substituted with at least one fluorine atom;
Rf 3 represents an alkyl group substituted with at least one fluorine atom;
X 1 and X 2 each independently represent —CO— or —SO 2 —;
X + represents a counter cation;
* represents a bonding site with R N ; and
a Log P value of R N —CH 3 is 1.2 or more to 4.0 or less, and
wherein the monovalent basic compound residue contains a structure having a primary amino group, a secondary amino group, or a tertiary amino group.

2. The pattern forming method according to claim 1 , wherein R N -A − in the general formula (I) is represented by general formula (II) shown below;

wherein in general formula (II),
A − is as defined in the general formula (I);
Q represents a linking group;
Rx 1 and Rx 2 each independently represent a hydrogen atom or an organic group, and at least one of Rx 1 and Rx 2 contains the alkyl group substituted with at least one fluorine atom;
two or more of Rx 1 , Rx 2 and Q may be bonded to each other to form a ring together with a nitrogen atom bonded therewith.

3. The pattern forming method according to claim 1 , wherein A − in the general formula (I) is represented by the general formula (a-3).

4. The pattern forming method according to claim 1 , wherein X + in the general formula (I) is an onium cation.

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

6. A manufacturing method of an electronic device including the pattern forming method according to claim 1 .

7. The pattern forming method according to claim 1 , wherein R N in the general formula (I) represents a monovalent basic compound residue containing at least one nitrogen atom and at least one trifluoromethyl group.

8. The pattern forming method according to claim 1 , wherein the Log P value of R N —CH 3 is 1.25 or more to 3.0 or less.

9. The pattern forming method according to claim 1 , wherein at least one of the at least one nitrogen atoms contained in the monovalent basic compound residue does not directly bond to an electron withdrawing functional group.

10. An actinic ray-sensitive or radiation-sensitive resin composition containing a compound (A) represented by general formula (I) shown below; a resin (P) capable of decreasing solubility with respect to a developer including an organic solvent by action of an acid; and a compound (B) capable of generating an acid by irradiation of actinic rays or radiation;
R N -A − X +   (I)

wherein in general formula (I),
R N represents a monovalent basic compound residue containing at least one nitrogen atom and an alkyl group substituted with at least one fluorine atom;
A − represents any of general formula (a-1) to (a-3) shown below;

Ar represents an aryl group or a heteroaryl group;
Rf 1 and Rf 2 each independently represent a fluorine atom or an alkyl group substituted with at least one fluorine atom;
Rf 3 represents an alkyl group substituted with at least one fluorine atom;
X 1 and X 2 each independently represent —CO— or —SO 2 —;
X + represents a counter cation;
* represents a bonding site with R N ;
a Log P value of RN—CH 3 is 1.2 or more to 4.0 or less,
wherein the monovalent basic compound residue contains a structure having a primary amino group, a secondary amino group, or a tertiary amino group.

11. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein R N -A − in the general formula (I) is represented by general formula (II) shown below:

wherein in general formula (II),
A − is as defined in the general formula (I);
Q represents a linking group;
Rx 1 and Rx 2 each independently represent a hydrogen atom or an organic group, and at least one of Rx 1 and Rx 2 contains the alkyl group substituted with at least one fluorine atom;
two or more of Rx 1 , Rx 2 and Q may be bonded to each other to form a ring together with a nitrogen atom bonded therewith.

12. An actinic ray-sensitive or radiation-sensitive film including the actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 .

13. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein R N in the general formula (I) represents a monovalent basic compound residue containing at least one nitrogen atom and at least one trifluoromethyl group.

14. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein the Log P value of R N —CH 3 is 1.25 or more to 3.0 or less.

15. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 10 , wherein at least one of the at least one nitrogen atoms contained in the monovalent basic compound residue does not directly bond to an electron withdrawing functional group.

16. A pattern forming method comprising:
(i) forming a film including an actinic ray-sensitive or radiation-sensitive resin composition containing a compound (A) represented by General Formula (I) shown below;
a resin (P) capable of decreasing solubility with respect to a developer including an organic solvent by action of an acid; and
a compound (B) capable of generating an acid by irradiation of actinic rays or radiation;
(ii) irradiating the film with actinic rays or radiation; and
(iii) developing the film irradiated with the actinic rays or radiation using a developer including an organic solvent;
R N -A − X +   (I)

wherein in general formula (I),
R N represents a monovalent basic compound residue containing at least one nitrogen atom and an alkyl group substituted with at least one fluorine atom;
A − represents general formula (a-3) shown below:

Assignees

• Fujifilm Corp

Inventors

• Kataoka Shohei
• Shibuya Akinori
• Goto Akiyoshi
• Matsuda Tomoki
• Fukuhara Toshiaki

Classifications

• G03F7/038 Primary

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/0397

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

• G03F7/30

  Imagewise removal using liquid means · CPC title

• G03F7/11

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

• G03F7/0045 Primary

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