# US 2024/0201591 A1 · Photoresist underlayer composition

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- Number: US 2024/0201591 A1
- Document ID: US20240201591A1
- Status: Published application
- Kind: A1
- Application number: 17/994,652
- Filed: 2022-11-28
- Published: 2024-06-20
- Earliest claimed: 2022-11-28
- Assignees: Rohm and Haas Electronic Materials Korea Ltd.
- Applicants: Rohm and Haas Electronic Materials Korea Ltd.
- Inventors: Yoo-Jin GHANG; Jae-Yun AHN; You Rim SHIN; Jung-June LEE; Jae-Hwan SIM
- Web page: https://patentgrep.com/patent/US20240201591A1

## CPC

- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- C08F 220/68: Esters
- C08F 222/20: Esters containing oxygen in addition to the carboxy oxygen
- C09D 133/16: Homopolymers or copolymers of esters containing halogen atoms
- C09D 135/02: Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence)
- G03F 7/094: {Multilayer resist systems, e.g. planarising layers}
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## 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

### Claim 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
repeating units derived from a monomer of Formula C1 or Formula C2,
wherein
Ar1, Ar2, and Ar3 are each independently an aromatic group;
R1 is a C1-20 alkyl alcohol, a C1-20 cycloalkyl alcohol, an epoxy with 3 to 12 carbons, or a C5-20 aromatic group with one to six ring carbons substituted with a hydroxy, a glycidyl group, a C1-10 alkyl alcohol, or an epoxy with 3 to 12 carbons;
R2 is R1 or —OH;
each of R2a, R2b, and R2c is independently an unsubstituted or substituted C1-20 alkyl, an unsubstituted or substituted C3-20 cycloalkyl, an unsubstituted or substituted C3-20 heterocycloalkyl, or optionally, R2a can join with R2b to form a ring, or R2a can join with R2c of Formulae B2 or B4 to form a ring, or one of R2a, R2b, and R2c is hydrogen;
L is an unsubstituted or substituted C1-8 alkylene group or an unsubstituted or substituted C2-8 heteroalkylene group;
L1 is an unsubstituted or substituted C1-8 alkylene group, an unsubstituted or substituted C2-8 heteroalkylene group, an unsubstituted or substituted C6-10 arylene group, or an unsubstituted or substituted C3-10 heteroarylene group;
L2 is a single bond, —O—, —O(C═O)—, —(C═O)O—, —O(SO2)—, —(SO2)O—, —NH(SO2)—, —(SO2)NH—, —NH(C═O)—, —(C═O)NH—, —SO2—, or —SO—;
D is a single bond, —O—, —OC(O)—, —NH(C═O)—, or —(C═O)NH—;
A is an unsubstituted or substituted C1-16 alkylene group, an unsubstituted or substituted C2-16 heteroalkylene group, an unsubstituted or substituted C6-20 arylene group, an unsubstituted or substituted C3-20 heteroarylene group;
each hal is independently a halogen atom or a C1-4 haloalkyl;
Ra is a hydrogen atom, a halogen atom, a C1-4 alkyl, or a C1-4 haloalkyl;
m is 0 or 1, and n is 1 to 12;
a crosslinker;
an acid catalyst; and a solvent.

### Claim 2 (depends on 1)

The composition of claim 1, wherein Ar1 and Ar3 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 Ar2 is a phenylene, naphthylene, anthracenylene, pyrenylene, pyridinylene, quinolinylene, biphenylene, fluorenylene, or carbazoylene, each of which is optionally further substituted at a ring carbon.

### Claim 3 (depends on 1)

The composition of claim 1, wherein Ar1 and Ar3 are each independently a phenyl, naphthyl, biphenyl, or fluorenyl, each of which is optionally further substituted at a ring carbon;
Ar2 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.

### Claim 4 (depends on 1)

The composition of claim 1, wherein R1 is a C1-10 alkyl alcohol, an epoxy with 3 to 8 carbons, or a C5-10 aromatic group with one to four ring carbons substituted with a hydroxy or a glycidyl group;
each of R2a, R2b, and R2c is independently an unsubstituted or substituted C1-8 alkyl, and optionally, R2a joins with R2b to form a ring, or R2a joins with R2c of Formulae B1 or B4 to form a ring;
L1 is an unsubstituted or substituted C1-8 alkylene group or an unsubstituted or substituted C2-8 heteroalkylene group;
L2 is a single bond, —O—, —O(C═O)—, or —NH(C═O)—;
A is an unsubstituted or substituted C2-8 alkylene group, an unsubstituted or substituted C3-8 heteroalkylene group.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 7)

The coated substrate of claim 7, wherein the photoresist layer is a metal-containing photoresist layer.

### Claim 9 (depends on 1)

A method of forming a pattern, the method comprising:
providing a photoresist underlayer over a substrate, wherein the photoresist underlayer is formed from the composition of claim 1;
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.