IP Library Granted Patent US 12,572,076
Granted Patent B2
US 12,572,076 · App. 17/994,652 · Granted Mar 10, 2026

Photoresist underlayer composition

Inventors: Yoo-Jin Ghang (Cheonan-si, KR); Jae-Yun Ahn (Cheonan-si, KR); You Rim Shin (Cheonan-si, KR); Jung-June Lee (Cheonan-si, KR); Jae-Hwan Sim (Cheonan-si, KR)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD
G03F7/11C08F220/68C08F222/20C09D133/16C09D135/02
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Quick Facts
Patent No.
US 12,572,076
App. No.
17/994,652
Granted
Mar 10, 2026
Kind
B2
Abstract

A composition comprising a polymer, the polymer comprising: repeating units derived from a monomer of Formula A1, Formula A2, or Formula A3, repeating units derived from a monomer of Formula B1, Formula B2, Formula B3, or Formula B4, and repeating units derived from a monomer of Formula C1 or Formula C2, the structures of each as described herein. A coated substrate including a substrate, a photoresist underlayer formed from composition above, and a photoresist layer on the photoresist underlayer.

Claims (49)

1 . A composition comprising a polymer, the polymer comprising:

repeating units derived from a monomer of Formula A1, Formula A2, or Formula A3,

repeating units derived from a monomer of Formula B1, Formula B2, Formula B3, or Formula B4,

and

Formula B3 Formula B4;

repeating units derived from a monomer of Formula C1 or Formula C2,

wherein

Ar 1 , Ar 2 , and Ar 3 are each independently an aromatic group;

R 1 is a C 1-20 alkyl alcohol, a C 1-20 cycloalkyl alcohol, an epoxy with 3 to 12 carbons, or a C 5-20 aromatic group with one to six ring carbons substituted with a hydroxy, a glycidyl group, a C 1-10 alkyl alcohol, or an epoxy with 3 to 12 carbons;

R 2 is R 1 or —OH;

each of R 2a , R 2b , and R 2c is independently an unsubstituted or substituted C 1-20 alkyl, an unsubstituted or substituted C 3-20 cycloalkyl, an unsubstituted or substituted C 3-20 heterocycloalkyl, or optionally, R 2a can join with R 2b to form a ring, or R 2a can join with R 2c of Formulae B2 or B4 to form a ring, or one of R 2a , R 2b , and R 2c is hydrogen;

L is an unsubstituted or substituted C 1-8 alkylene group or an unsubstituted or substituted C 2-8 heteroalkylene group;

L 1 is an unsubstituted or substituted C 1-8 alkylene group, an unsubstituted or substituted C 2-8 heteroalkylene group, an unsubstituted or substituted C 6-10 arylene group, or an unsubstituted or substituted C 3-10 heteroarylene group;

L 2 is a single bond, —O—, —O(C═O)—, —(C═O)O—, —O(SO 2 )—, —(SO 2 )O—, —NH(SO 2 )—, —(SO 2 )NH—, —NH(C═O)—, —(C═O)NH—, —SO 2 —, or —SO—;

D is a single bond, —O—, —OC(O)—, —NH(C═O)—, or —(C═O)NH—;

A is an unsubstituted or substituted C 1-16 alkylene group, an unsubstituted or substituted C 2-16 heteroalkylene group, an unsubstituted or substituted C 6-20 arylene group, an unsubstituted or substituted C 3-20 heteroarylene group;

each hal is independently a halogen atom or a C 1-4 haloalkyl;

R a is a hydrogen atom, a halogen atom, a C 1-4 alkyl, or a C 1-4 haloalkyl;

m is 0 or 1, and n is 1 to 12;

a crosslinker;

an acid catalyst; and a solvent wherein the composition is a photoresist underlayer composition.

2 . The composition of claim 1 , wherein Ar 1 and Ar 3 are each independently a phenyl, naphthyl, anthracenyl, pyrenyl, pyridinyl, quinolinyl, biphenyl, fluorenyl, or carbazoyl, each of which is optionally further substituted at a ring carbon; and Ar 2 is a phenylene, naphthylene, anthracenylene, pyrenylene, pyridinylene, quinolinylene, biphenylene, fluorenylene, or carbazoylene, each of which is optionally further substituted at a ring carbon.

3 . The composition of claim 1 , wherein Ar 1 and Ar 3 are each independently a phenyl, naphthyl, biphenyl, or fluorenyl, each of which is optionally further substituted at a ring carbon;

Ar 2 is a phenylene, naphthylene, biphenylene, or fluorenylene, each of which is optionally further substituted at a ring carbon; and

hal is F, Br, I, or if n is 2 or more a combination thereof.

4 . The composition of claim 1 , wherein

R 1 is a C 1-10 alkyl alcohol, an epoxy with 3 to 8 carbons, or a C 5-10 aromatic group with one to four ring carbons substituted with a hydroxy or a glycidyl group;

each of R 2a , R 2b , and R 2c is independently an unsubstituted or substituted C 1-8 alkyl, and optionally, R 2a joins with R 2b to form a ring, or R 2a joins with R 2c of Formulae B1 or B4 to form a ring;

L 1 is an unsubstituted or substituted C 1-8 alkylene group or an unsubstituted or substituted C 2-8 heteroalkylene group;

L 2 is a single bond, —O—, —O(C═O)—, or —NH(C═O)—;

A is an unsubstituted or substituted C 2-8 alkylene group, an unsubstituted or substituted C 3-8 heteroalkylene group.

5 . The composition of claim 1 , wherein

the monomer of Formulae A1, A2, and A3 are represented by one or more of the following

and

the monomer of Formulae B1 and B3 are represented by one or more of the following

6 . The composition of claim 1 , wherein the monomer of Formulae C1 and C2 are represented by one or more of the following

7 . The composition of claim 1 wherein the composition does not include a photoacid generator.

8 . A coated substrate, comprising:

a substrate;

a photoresist underlayer formed from the composition of claim 1 disposed on the substrate; and

a photoresist layer disposed on the photoresist underlayer.

9 . The coated substrate of claim 8 , wherein the photoresist layer is a metal-containing photoresist layer.

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

providing a photoresist underlayer over a substrate, wherein the photoresist underlayer is formed by applying the composition of claim 1 to the substrate, removing the solvent, and curing;

forming a photoresist layer over the photoresist underlayer;

patterning the photoresist layer; and

transferring a pattern from the patterned photoresist layer to the photoresist underlayer.

11 . The method of claim 10 wherein the cure is a thermal cure.

12 . The method of claim 10 wherein the cure occurs before applying the photoresist layer.

Assignments (2)
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2023
From: GHANG, YOO-JIN; AHN, JAE-YUN; SHIN, YOU RIM; LEE, JUNG-JUNE; SIM, JAE-HWAN
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD
Reel/Frame 062371/0120 →