IP Library › Granted Patent US 12699321
Granted Patent B2
US 12699321 · App. 17/924,521 · Granted Aug 4, 2026

Compound, (co)polymer, composition, method for forming resist pattern, method for producing compound, and method for producing (co)polymer

Inventors: Tadashi Omatsu (Hiratsuka, JP); Masahiro Matsumoto (Niigata, JP); Michihiro Yuri (Niigata, JP); Kentaro Kataoka (Niigata, JP); Takashi Sato (Hiratsuka, JP); Masatoshi Echigo (Tokyo, JP)
Assignee: Mitsubishi Gas Chemical Company, Inc.
G03F7/0397C07C67/24C07C69/653C08F8/12C08F20/18C08F20/26C08F220/22G03F7/039
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12699321
App. No.
17/924,521
Granted
Aug 4, 2026
Kind
B2
Abstract

An iodine-containing (meth)acrylate compound represented by formula (1): wherein R 1 represents a hydrogen atom, methyl, or halogen; each R 2 independently represents a hydrogen atom, a linear organic group having 1 to 20 carbon atoms, a branched organic group having 3 to 20 carbon atoms, or a cyclic organic group having 3 to 20 carbon atoms; A represents an organic group having 1 to 30 carbon atoms; A contains at least one acyl group; n 1 represents 0 or 1; and n 2 represents an integer of 1 to 20.

Claims (37)

1 . An iodine-containing (meth) acrylate compound represented by formula (1):

wherein

R 1 represents a hydrogen atom, a methyl group, or halogen;

each R 2 independently represents a hydrogen atom, a linear organic group having 1 to 20 carbon atoms, a branched organic group having 3 to 20 carbon atoms, or a cyclic organic group having 3 to 20 carbon atoms;

A is adamantane or benzene having at least one acetoxy group;

n 1 represents 0 or 1; and

n 2 represents an integer of 1 to 20.

2 . The iodine-containing (meth) acrylate compound according to claim 1 , wherein the formula (1) is formula (2):

wherein R 1 , A, and n 2 are the same as described above.

3 . The iodine-containing (meth) acrylate compound according to claim 2 , wherein the formula (2) is formula (3):

wherein B represents an organic group containing an aromatic group and having 5 to 30 carbon atoms, B is benzene having at least one acetoxy group, and R 1 and n 2 are as described above.

4 . The iodine-containing (meth) acrylate compound according to claim 2 , wherein the formula (2) is formula (3′):

wherein B′ represents an organic group containing an alicyclic ring and having 5 to 30 carbon atoms, B′ is adamantane having at least one acetoxy group, and R 1 and n 2 are as described above.

5 . The iodine-containing (meth) acrylate compound according to claim 1 , wherein n 2 represents an integer of 2 to 20.

6 . An iodine-containing (meth) acrylate (co) polymer comprising a constituent unit represented by formula (4):

wherein

R 1 represents a hydrogen atom, a methyl group, or halogen;

each R 2 independently represents a hydrogen atom, a linear organic group having 1 to 20 carbon atoms, a branched organic group having 3 to 20 carbon atoms, or a cyclic organic group having 3 to 20 carbon atoms;

A is adamantane or benzene having at least one acetoxy group;

n 1 represents 0 or 1;

n 2 represents an integer of 1 to 20; and

the symbol * represents a bonding site to an adjacent constituent unit.

7 . The iodine-containing (meth) acrylate (co) polymer according to claim 6 , wherein the formula (4) is formula (5):

wherein R 1 , n 2 , A, and the symbol * are the same as described above.

8 . The iodine-containing (meth) acrylate (co) polymer according to claim 7 , wherein the formula (5) is formula (6):

wherein B represents an organic group containing an aromatic group and having 5 to 30 carbon atoms, B is benzene having at least one acetoxy group, and R 1 , n 2 , and the symbol * are as described above.

9 . The iodine-containing (meth) acrylate (co) polymer according to claim 7 , wherein the formula (5) is formula (6′):

wherein B′ represents an organic group containing an alicyclic ring and having 5 to 30 carbon atoms, B′ is adamantane having at least one acetoxy group, and R 1 , n 2 , and the symbol * are as described above.

10 . The iodine-containing (meth) acrylate (co) polymer according to claim 6 , wherein n 2 represents an integer of 2 to 20.

11 . A composition comprising the iodine-containing (meth) acrylate compound according to claim 1 .

12 . The composition according to claim 11 , further comprising a solvent.

13 . The composition according to claim 11 , further comprising an acid generating agent.

14 . The composition according to claim 11 , further comprising an acid diffusion controlling agent.

15 . A method for forming a resist pattern, comprising the steps of:

forming a film using the composition according to claim 11 ;

exposing the formed film; and

removing an exposed portion of the exposed film using a developer to form a pattern.