IP Library Granted Patent US 12,516,074
Granted Patent B2
US 12,516,074 · App. 17/696,982 · Granted Jan 6, 2026

Composition, film, method of forming film, method of forming pattern, method of forming organic-underlayer-film reverse pattern, and method of producing composition

Inventors: Yuusuke Ootsubo (Tokyo, JP); Ryuichi Serizawa (Tokyo, JP); Kazunori Sakai (Tokyo, JP)
Assignee: JSR CORPORATION
C07F7/28C07F15/04C07F15/06G03F7/094G03F7/2004G03F7/039G03F7/11G03F7/20G03F7/40
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Quick Facts
Patent No.
US 12,516,074
App. No.
17/696,982
Granted
Jan 6, 2026
Kind
B2
Abstract

A composition includes: a metal compound including a ligand; and a solvent. The ligand is derived from a compound represented by formula (1). L represents an oxygen atom or a single bond; R 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R 2 and R 3 each independently represent a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, or R 2 and R 3 bind with each other and represent an alicyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond, or R 1 and either R 2 or R 3 bind with each other and represent a lactone ring structure having 4 to 20 ring atoms or a cyclic ketone structure having 4 to 20 ring atoms together with the atom chain to which R 1 and either R 2 or R 3 bond.

Claims (53)

1 . A composition comprising:

a metal compound comprising a ligand; and

a solvent,

wherein the ligand is derived from a compound represented by formula (1):

wherein, in the formula (1), L represents a single bond; R 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R 2 and R 3 each independently represent a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, or R 2 and R 3 bind with each other and represent an alicyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond, or R 1 and either R 2 or R 3 bind with each other and represent a lactone ring structure having 4 to 20 ring atoms or a cyclic ketone structure having 4 to 20 ring atoms together with the atom chain to which R 1 and either R 2 or R 3 bond.

2 . The composition according to claim 1 , wherein a metal atom in the metal compound belongs to period 3 to period 7 of group 2 to group 14 in periodic table.

3 . The composition according to claim 2 , wherein the metal atom belongs to group 4, group 9, or group 10 in the periodic table.

4 . The composition according to claim 1 , wherein R 1 represents a substituted or unsubstituted monovalent chain hydrocarbon group having 1 to 10 carbon atoms.

5 . The composition according to claim 1 , wherein R 2 and R 3 each represent a hydrogen atom.

6 . A film formed from the composition according to claim 1 .

7 . A method of forming a film, the method comprising applying the composition according to claim 1 directly or indirectly on a substrate.

8 . A method of forming a pattern, the method comprising:

applying the composition according to claim 1 directly or indirectly on a substrate to form a resist underlayer film;

applying an organic-resist-film-forming composition directly or indirectly on the resist underlayer film to form an organic resist film;

exposing the organic resist film to a radioactive ray; and

developing the organic resist film exposed.

9 . A method of forming an organic-underlayer-film reverse pattern, the method comprising:

forming an organic underlayer film directly or indirectly on a substrate;

forming a resist pattern directly or indirectly on the organic underlayer film;

forming an organic-underlayer-film pattern by etching the organic underlayer using the resist pattern as a mask;

forming an organic-underlayer-film-reverse-pattern-forming film on the organic-underlayer-film pattern by applying the composition according to claim 1 ; and

removing the organic-underlayer-film pattern to form an organic-underlayer-film reverse pattern.

10 . A method of producing the composition according to claim 1 , the method comprising:

mixing a metal alkoxide and a compound represented by formula (1) to obtain a mixture;

adding water to the mixture to cause a hydrolytic condensation reaction of the metal alkoxide; and

adding a solvent to the mixture to which the water is added:

wherein, in the formula (1), L represents a single bond; R 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R 2 and R 3 each independently represent a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, or R 2 and R 3 bind with each other and represent an alicyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond, or R 1 and either R 2 or R 3 bind with each other and represent a lactone ring structure having 4 to 20 ring atoms or a cyclic ketone structure having 4 to 20 ring atoms together with the atom chain to which R 1 and either R 2 or R 3 bond.

11 . A composition comprising:

a metal compound comprising a ligand; and

a solvent,

wherein the ligand is derived from a compound represented by formula (1):

wherein, in the formula (1), L represents an oxygen atom or a single bond; R 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R 2 and R 3 each represent a hydrogen atom.

12 . The composition according to claim 11 , wherein a metal atom in the metal compound belongs to period 3 to period 7 of group 2 to group 14 in periodic table.

13 . The composition according to claim 12 , wherein the metal atom belongs to group 4, group 9, or group 10 in the periodic table.

14 . The composition according to claim 11 , wherein R 1 represents a substituted or unsubstituted monovalent chain hydrocarbon group having 1 to 10 carbon atoms.

15 . A film formed from the composition according to claim 11 .

16 . A method of forming a film, the method comprising applying the composition according to claim 11 directly or indirectly on a substrate.

17 . A method of forming a pattern, the method comprising:

applying the composition according to claim 11 directly or indirectly on a substrate to form a resist underlayer film;

applying an organic-resist-film-forming composition directly or indirectly on the resist underlayer film to form an organic resist film;

exposing the organic resist film to a radioactive ray; and

developing the organic resist film exposed.

18 . A method of forming an organic-underlayer-film reverse pattern, the method comprising:

forming an organic underlayer film directly or indirectly on a substrate;

forming a resist pattern directly or indirectly on the organic underlayer film;

forming an organic-underlayer-film pattern by etching the organic underlayer using the resist pattern as a mask;

forming an organic-underlayer-film-reverse-pattern-forming film on the organic-underlayer-film pattern by applying the composition according to claim 11 ; and

removing the organic-underlayer-film pattern to form an organic-underlayer-film reverse pattern.

19 . A method of producing the composition according to claim 11 , the method comprising:

mixing a metal alkoxide and a compound represented by formula (1) to obtain a mixture;

adding water to the mixture to cause a hydrolytic condensation reaction of the metal alkoxide; and

adding a solvent to the mixture to which the water is added:

wherein, in the formula (1), L represents an oxygen atom or a single bond; R 1 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms; R 2 and R 3 each independently represent a hydrogen atom.

Assignments (3)
MERGER Recorded Apr 21, 2025
From: JSR CORPORATION
To: JICC-02 CO., LTD.
Reel/Frame 070894/0405 →
CHANGE OF NAME Recorded Apr 21, 2025
From: JICC-02 CO., LTD.
To: JSR CORPORATION
Reel/Frame 070894/0498 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2022
From: OOTSUBO, YUUSUKE; SERIZAWA, RYUICHI; SAKAI, KAZUNORI
To: JSR CORPORATION
Reel/Frame 059968/0085 →
Priority Claims (1)
JP 2019-177719 · Sep 27, 2019 · national
Continuity (2)
Continuation PCTJP2020036358 · Sep 25, 2020
Related Publication 20220204535A1 · Jun 30, 2022
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