Radiation-sensitive composition, pattern-forming method, and metal-containing resin and production method thereof

Patent metadata

Field	Value
Publication number	US-11079676-B2
Application number	US-201916449701-A
Country	US
Kind code	B2
Filing date	Jun 24, 2019
Priority date	Dec 28, 2016
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

A radiation-sensitive composition is to be used in exposure with an extreme ultraviolet ray or an electron beam, and includes a first polymer and a solvent, wherein the first polymer includes a first structural unit including: at least one metal atom; and at least one carbon atom that each bonds to the metal atom by a chemical bond and does not constitute an unsaturated bond, and at least one chemical bond is a covalent bond. Every chemical bond is preferably a covalent bond. The metal atom is preferably tin, germanium, lead or a combination thereof.

First claim

What is claimed is:

1. A radiation-sensitive composition for exposure with an extreme ultraviolet ray or an electron beam, comprising:
a polymer; and
a solvent dissolving or dispersing the polymer,
wherein the polymer comprises a structural unit comprising at least one formula selected from the group consisting of

where M is a metal atom, R 1 is a monovalent organic group having 1 to 20 carbon atoms, n is an integer of 1 to 4 such that when n is no less than 2, a plurality of R 1 s is identical or different, at least one R 1 bonds to M via a carbon atom that bonds to the metal atom by a covalent bond and does not constitute an unsaturated bond, L 1 and L 2 each independently are a divalent linking group having 1 to 30 atoms, R 2 is a monovalent organic group having 1 to 20 carbon atoms, m is an integer of 1 to 4 such that when m is no less than 2, a plurality of R 2 s is identical or different, at least one of L 1 , L 2 and at least one R 2 bonds to M via a carbon atom that bonds to the metal atom by a covalent bond and does not constitute an unsaturated bond, R A is a hydrogen atom or a monovalent organic group having 1 to 10 carbon atoms, L 3 is a divalent linking group having 1 to 30 atoms, R 3 is a monovalent organic group having 1 to 20 carbon atoms, p is an integer of 1 to 5 such that when p is no less than 2, a plurality of R 3 s is identical or different, and at least one of L 3 and at least one R 3 bonds to M via a carbon atom that bonds to the metal atom by a covalent bond and does not constitute an unsaturated bond.

2. The radiation-sensitive composition according to claim 1 , wherein every chemical bond is a covalent bond.

3. The radiation-sensitive composition according to claim 1 , wherein the metal atom is tin, germanium, lead or a combination thereof.

4. The radiation-sensitive composition according to claim 1 , wherein the metal atom is tin.

5. The radiation-sensitive composition according to claim 4 , wherein the structural unit of the polymer comprises at least one formula selected from the group consisting of

6. The radiation-sensitive composition according to claim 4 , wherein the structural unit of the polymer comprises at least one formula selected from the group consisting of

7. The radiation-sensitive composition according to claim 4 , wherein the structural unit of the polymer comprises

8. The radiation-sensitive composition according to claim 4 , wherein the structural unit of the polymer comprises at least one formula selected from the group consisting of

9. The radiation-sensitive composition according to claim 1 , wherein a content of the polymer in terms of solid content equivalent is no less than 50% by mass.

10. The radiation-sensitive composition according to claim 1 , wherein the solvent comprises an alcohol solvent, an ether solvent, a ketone solvent, an amide solvent, an ester solvent, a hydrocarbon solvent or a combination thereof.

11. The radiation-sensitive composition according to claim 10 , wherein the solvent comprises an ester solvent comprising a polyhydric alcohol partially etherated carboxylate solvent.

12. The radiation-sensitive composition according to claim 1 , wherein the polymer further comprises a second structural unit comprising a polar group.

13. The radiation-sensitive composition according to claim 1 , wherein the polymer further comprises a third structural unit which is a structural unit other than the structural unit and comprises a crosslinkable group.

14. The radiation-sensitive composition according to claim 1 , wherein the polymer comprises the metal atom in a side chain thereof.

15. The radiation-sensitive composition according to claim 1 , further comprising a fluorine atom-containing polymer other than the polymer.

16. The radiation-sensitive composition according to claim 1 , further comprising a surfactant.

17. A pattern-forming method comprising:
applying the radiation-sensitive composition of claim 1 directly or indirectly on one face side of a substrate such that a film comprising the radiation-sensitive composition is formed on the substrate;
exposing the film formed on the substrate; and
developing the film exposed on the substrate.

18. The pattern-forming method according to claim 17 , wherein the developing includes applying a developer solution comprising an aqueous alkali solution.

19. The pattern-forming method according to claim 17 , wherein the developing includes applying a developer solution comprising an organic solvent.

20. The pattern-forming method according to claim 19 , wherein the organic solvent comprises an ester solvent, an ether solvent, an alcohol solvent, a ketone solvent, an amide solvent, a hydrocarbon solvent or a combination thereof.

21. The pattern-forming method according to any one of claim 17 , wherein a radioactive ray is an extreme ultraviolet ray or an electron beam.

22. A metal-containing resin, comprising:
a polymer,
wherein the polymer comprises a structural unit comprising at least one formula selected from the group consisting of

where M is a metal atom, R 1 is a monovalent organic group having 1 to 20 carbon atoms, n is an integer of 1 to 4 such that when n is no less than 2, a plurality of R 1 s is identical or different, at least one R 1 bonds to M via a carbon atom that bonds to the metal atom by a covalent bond and does not constitute an unsaturated bond, L 1 and L 2 each independently are a divalent linking group having 1 to 30 atoms, R 2 is a monovalent organic group having 1 to 20 carbon atoms, in is an integer of 1 to 4 such that when in is no less than 2, a plurality of R 2 s is identical or different, at least one of L 1 , L 2 and at least one R 2 bonds to M via a carbon atom that bonds to the metal atom by a covalent bond and does not constitute an unsaturated bond, R A is a hydrogen atom or a monovalent organic group having 1 to 10 carbon atoms, L 3 is a divalent linking group having 1 to 30 atoms, R 3 is a monovalent organic group having 1 to 20 carbon atoms, p is an integer of 1 to 5 such that when p is no less than 2, a plurality of R 3 s is identical or different, and at least one of L 3 and at least one R 3 bonds to M via a carbon atom that bonds to the metal atom by a covalent bond and does not constitute an unsaturated bond.

23. A method of producing a metal-containing resin, comprising:
forming a main chain of a polymer by chain polymerization with a radical, an anion or a cation such that the polymer comprises a structural unit comprising at least one formula selected from the group consisting of

where M is a metal atom, R 1 is a monovalent organic group having 1 to 20 carbon ato

Assignees

• Jsr Corp

Inventors

• Asano Yusuke
• Nakagawa Hisashi
• Minegishi Shinya

Classifications

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title

• C08G79/12

  a linkage containing tin · CPC title

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• C08F12/14

  substituted by hetero atoms or groups containing heteroatoms · CPC title