IP Library Granted Patent US 11,402,757
Granted Patent B2
US 11,402,757 · App. 16/871,131 · Granted Aug 2, 2022

Composition for resist underlayer film formation, resist underlayer film and forming method thereof, patterned substrate-producing method, and compound

Inventors: Naoya Nosaka (Tokyo, JP); Yuushi Matsumura (Tokyo, JP); Hiroki Nakatsu (Tokyo, JP); Kazunori Takanashi (Tokyo, JP); Hiroki Nakagawa (Tokyo, JP)
Assignee: JSR CORPORATION
G03F7/11C07D251/24C09D7/63H01L21/0274G03F7/162G03F7/20G03F7/30
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Quick Facts
Patent No.
US 11,402,757
App. No.
16/871,131
Granted
Aug 2, 2022
Kind
B2
Abstract

A composition for resist underlayer film formation, includes a compound represented by formula (1) and a solvent. Ar 1 represents an aromatic heterocyclic group having a valency of m and having 5 to 20 ring atoms; m is an integer of 1 to 11; Ar 2 is a group bonding to a carbon atom of the aromatic heteroring in Ar 1 and represents an aromatic carbocyclic group having 6 to 20 ring atoms and having a valency of (n+1) or an aromatic heterocyclic group having 5 to 20 ring atoms and having a valency of (n+1); n is an integer of 0 to 12; and R 1 represents a monovalent organic group having 1 to 20 carbon atoms, a hydroxy group, a halogen atom, or a nitro group. Ar 1 Ar 2 R 1 ) n ) m   (1)

Claims (79)

1. A composition for resist underlayer film formation, comprising:

a compound represented by formula (1); and

a solvent,

Ar 1 Ar 2 R 1 ) n ) m   (1)

wherein, in the formula (1),

Ar 1 represents a 1,3,5-triazinetriyl group;

m is an integer of 3;

Ar 2 is a group bonding to a carbon atom of the 1,3,5-triazinetriyl group represented by Ar 1 and represents an aromatic carbocyclic group having 6 to 20 ring atoms and having a valency of (n+1);

n is an integer of 0 to 12,

wherein a plurality of Ar 2 s are identical or different from each other, and a plurality of n's are identical or different from each other; and

R 1 represents a monovalent organic group having 1 to 20 carbon atoms, a hydroxy group, a halogen atom, or a nitro group,

wherein the number of R 1 s in the compound is three or more,

wherein at least three R 1 s each represent an organic group comprising at least one multiple bond or an organic group comprising an epoxy group, the at least one multiple bond being selected from the group consisting of: an ethylenic carbon-carbon double bond; a carbon-carbon triple bond; a carbon-nitrogen double bond; a carbon-nitrogen triple bond; and a carbon-oxygen double bond, and

wherein in a case in which R 1 is present in a plurality of number, a plurality of R 1 s are identical or different from each other.

2. The composition according to claim 1 , wherein Ar 2 in the formula (1) represents a group obtained from benzene by removing (n+1) hydrogen atoms bonding to a carbon atom of an aromatic carbon ring.

3. The composition according to claim 1 , wherein the monovalent organic group having 1 to 20 carbon atoms represented by R 1 in the formula (1) is:

a monovalent hydrocarbon group having 1 to 20 carbon atoms;

a group in which a divalent hetero atom-containing group is inserted between two adjacent carbon atoms of a monovalent hydrocarbon group having 1 to 20 carbon atoms;

a group comprising a divalent hetero atom-containing group and a monovalent hydrocarbon group having 1 to 20 carbon atoms, wherein the divalent hetero atom-containing group is positioned between the monovalent hydrocarbon group and an atom constituting Ar 2 ;

a group obtained by substituting with a monovalent hetero atom-containing group, a part or all of hydrogen atoms included in a monovalent hydrocarbon group having 1 to 20 carbon atoms;

a group obtained by substituting with a monovalent hetero atom-containing group, a part or all of hydrogen atoms included in a group in which a divalent hetero atom-containing group is inserted between two adjacent carbon atoms of a monovalent hydrocarbon group having 1 to 20 carbon atoms;

a group obtained by substituting with a monovalent hetero atom-containing group, a part or all of hydrogen atoms included in a group comprising a divalent hetero atom-containing group and a monovalent hydrocarbon group having 1 to 20 carbon atoms, wherein the divalent hetero atom-containing group is positioned between the monovalent hydrocarbon group and an atom constituting Ar 2 ; or

a group comprising a divalent hetero atom-containing group and a monovalent hetero atom-containing group, wherein the divalent hetero atom-containing group is positioned between the monovalent hetero atom-containing group and an atom constituting Ar 2 .

4. The composition according to claim 1 , wherein the monovalent organic group having 1 to 20 carbon atoms represented by R 1 in the formula (1) is a group represented by formula (2):

*—X—R 1′   (2)

wherein, in the formula (2), X represents a single bond or a divalent hetero atom-containing group; R 1′ represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent hetero atom-containing group, or a group obtained by substituting with a monovalent hetero atom-containing group, a part or all of hydrogen atoms included in a monovalent hydrocarbon group having 1 to 20 carbon atoms; and * denotes a bonding site to Ar 2 .

5. The composition according to claim 1 , further comprising at least one selected from the group consisting of an acid generating agent and a crosslinking agent.

6. The composition according to claim 1 , wherein in the formula (1), n is an integer of 2 to 8.

7. The composition according to claim 1 , wherein in the formula (1), n is an integer of 3 to 6.

8. The composition according to claim 1 , wherein the at least one multiple bond is selected from the group consisting of: an ethylenic carbon-carbon double bond; a carbon-carbon triple bond; a carbon-nitrogen double bond; and a carbon-nitrogen triple bond.

9. The composition according to claim 1 , wherein the at least one multiple bond is selected from the group consisting of: a carbon-carbon triple bond; and a carbon-nitrogen triple bond.

10. A resist underlayer film formed from the composition according to claim 1 .

11. A resist underlayer film-forming method comprising:

applying the composition according to claim 1 directly or indirectly on one face side of a substrate to form a coating film; and

heating the coating film.

12. A patterned substrate-producing method comprising:

applying a composition for resist underlayer film formation comprising a compound represented by formula (1) and a solvent, directly or indirectly on an upper face side of a substrate to form a coating film;

heating the coating film to form a resist underlayer film;

forming a resist pattern on an upper face side of the resist underlayer film; and

etching the substrate using the resist pattern as a mask,

Ar 1 Ar 2 R 1 ) n ) m   (1)

wherein, in the formula (1),

Ar 1 represents a 1,3,5-triazinetriyl group;

m is an integer of 3;

Ar 2 is a group bonding to a carbon atom of the 1,3,5-triazinetriyl group represented by Ar 1 and represents an aromatic carbocyclic group having 6 to 20 ring atoms and having a valency of (n+1);

n is an integer of 0 to 12,

wherein a plurality of Ar 2 s are identical or different from each other, and a plurality of n's are identical or different from each other; and

R 1 represents a monovalent organic group having 1 to 20 carbon atoms, a hydroxy group, a halogen atom, or a nitro group,

wherein the number of R 1 s in the compound is three or more,

wherein at least three R 1 s each represent an organic group comprising at least one multiple bond or an organic group comprising an epoxy group, the at least one multiple bond being selected from the group consisting of: an ethylenic carbon-carbon double bond; a carbon-carbon triple bond; a carbon-nitrogen double bond; a carbon-nitrogen triple bond; and a carbon-oxygen double bond, and

wherein in a case in which R 1 is present in a plurality of number, a plurality of R 1 s are identical or different from each other.

13. The patterned substrate-producing method according to claim 12 , further comprising forming a silicon-containing film on the upper face side of the resist underlayer film before forming the resist pattern.

14. The patterned substrate-producing method according to claim 12 , wherein Ar 2 in the formula (1) represents a group obtained from benzene by removing (n+1) hydrogen atoms bonding to a carbon atom of an aromatic carbon ring.

15. The patterned substrate-producing method according to claim 12 , wherein the monovalent organic group having 1 to 20 carbon atoms represented by R 1 in the formula (1) is:

a monovalent hydrocarbon group having 1 to 20 carbon atoms;

a group in which a divalent hetero atom-containing group is inserted between two adjacent carbon atoms of a monovalent hydrocarbon group having 1 to 20 carbon atoms;

a group comprising a divalent hetero atom-containing group and a monovalent hydrocarbon group having 1 to 20 carbon atoms, wherein the divalent hetero atom-containing group is positioned between the monovalent hydrocarbon group and an atom constituting Ar 2 ;

a group obtained by substituting with a monovalent hetero atom-containing group, a part or all of hydrogen atoms included in a monovalent hydrocarbon group having 1 to 20 carbon atoms;

a group obtained by substituting with a monovalent hetero atom-containing group, a part or all of hydrogen atoms included in a group in which a divalent hetero atom-containing group is inserted between two adjacent carbon atoms of a monovalent hydrocarbon group having 1 to 20 carbon atoms;

a group obtained by substituting with a monovalent hetero atom-containing group, a part or all of hydrogen atoms included in a group comprising a divalent hetero atom-containing group and a monovalent hydrocarbon group having 1 to 20 carbon atoms, wherein the divalent hetero atom-containing group is positioned between the monovalent hydrocarbon group and an atom constituting Ar 2 ; or

a group comprising a divalent hetero atom-containing group and a monovalent hetero atom-containing group, wherein the divalent hetero atom-containing group is positioned between the monovalent hetero atom-containing group and an atom constituting Ar 2 .

16. The patterned substrate-producing method according to claim 12 , wherein the monovalent organic group having 1 to 20 carbon atoms represented by R 1 in the formula (1) is a group represented by formula (2):

*—X—R 1′   (2)

wherein, in the formula (2), X represents a single bond or a divalent hetero atom-containing group; R 1′ represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent hetero atom-containing group, or a group obtained by substituting with a monovalent hetero atom-containing group, a part or all of hydrogen atoms included in a monovalent hydrocarbon group having 1 to 20 carbon atoms; and * denotes a bonding site to Ar 2 .

17. The patterned substrate-producing method according to claim 12 , wherein in the formula (1), n is an integer of 2 to 8.

18. The patterned substrate-producing method according to claim 12 , wherein in the formula (1), n is an integer of 3 to 6.

19. The patterned substrate-producing method according to claim 12 , wherein the at least one multiple bond is selected from the group consisting of: an ethylenic carbon-carbon double bond; a carbon-carbon triple bond; a carbon-nitrogen double bond; and a carbon-nitrogen triple bond.

20. A compound represented by formula (1′):

Ar 1 Ar 2 R 1 ) n ) m   (1′)

wherein, in the formula (1′),

Ar 1 represents a 1,3,5-triazinetriyl group;

m is an integer of 3;

Ar 2 is a group bonding to a carbon atom of the 1,3,5-triazinetriyl group represented by Ar 1 and represents an aromatic carbocyclic group having 6 to 20 ring atoms and having a valency of (n+1);

n is an integer of 0 to 12,

wherein a plurality of Ar 2 s are identical or different from each other, and a plurality of n's are identical or different from each other; and

R 1 represents a monovalent organic group having 1 to 20 carbon atoms, a hydroxy group, a halogen atom, or a nitro group,

wherein the number of R 1 s in the compound is three or more,

wherein at least three les each represent an organic group comprising at least one multiple bond or an organic group comprising an epoxy group, the at least one multiple bond being selected from the group consisting of: an ethylenic carbon-carbon double bond; a carbon-carbon triple bond; a carbon-nitrogen double bond; a carbon-nitrogen triple bond; and a carbon-oxygen double bond, and

wherein in a case in which R 1 is present in a plurality of number, a plurality of R 1 s are identical or different from each other.

Assignments (3)
MERGER Recorded Mar 23, 2026
From: JSR CORPORATION
To: JICC-02, CO., LTD
Reel/Frame 075191/0149 →
CHANGE OF NAME Recorded Mar 23, 2026
From: JICC-02 CO., LTD
To: JSR CORPORATION
Reel/Frame 075192/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2021
From: NOSAKA, NAOYA; MATSUMURA, YUUSHI; NAKATSU, HIROKI; TAKANASHI, KAZUNORI; NAKAGAWA, HIROKI
To: JSR CORPORATION
Reel/Frame 056066/0035 →
Priority Claims (1)
JP JP2017-221341 · Nov 16, 2017 · national
Continuity (2)
Continuation PCTJP2018041410 · Nov 7, 2018
Related Publication 20200272053A1 · Aug 27, 2020