IP Library Granted Patent US 11,809,077
Granted Patent B2
US 11,809,077 · App. 17/198,749 · Granted Nov 7, 2023

Photoresist compositions and pattern formation methods

Inventors: Thomas Cardolaccia (Natick, MA); Jason A. DeSisto (Hopkinton, MA); Choong-Bong Lee (Westborough, MA); Mingqi Li (Shrewsbury, MA); Tomas Marangoni (Marlborough, MA); Chunyi Wu (Shrewsbury, MA); Cong Liu (Shrewsbury, MA); Gregory P. Prokopowicz (Worcester, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
G03F7/0045C08F220/18C08F220/281G03F7/027
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Quick Facts
Patent No.
US 11,809,077
App. No.
17/198,749
Granted
Nov 7, 2023
Kind
B2
Abstract

A photoresist composition comprises a first polymer formed by free radical polymerization. The first polymer comprises polymerized units formed from a monomer that comprises an ethylenically unsaturated double bond and an acid-labile group; a photoacid generator; a quencher of formula (1): and a solvent.

Claims (23)

1. A photoresist composition, comprising:

a first polymer formed by free radical polymerization, the first polymer comprising polymerized units formed from a monomer comprising an ethylenically unsaturated double bond and an acid-labile group;

a photoacid generator;

a quencher of formula (1):

wherein: R 1 is independently a hydrogen atom, C 1 -C 20 linear, C 3 -C 20 branched, or C 3 -20 cyclic alkyl, the alkyl optionally comprising an —O— group other than at an alpha-position with respect to the amide C(O), or C 6 -C 20 aryl; R 2 is independently a hydrogen atom, C 1 -C 20 linear, C 3 -C 20 branched, or C 3 -C 20 cyclic alkyl, or C 6 -C 20 aryl; L is C 1 -C 20 linear or C 3 -C 20 branched alkylene comprising one or more heteroatom-containing groups independently selected from —O—, or —S—; wherein each of R 1 , R 2 , and L may independently be substituted or unsubstituted; wherein the quencher is free of crosslinkable groups; and

a solvent.

2. The photoresist composition of claim 1 , wherein L comprises a plurality of heteroatom-containing groups.

3. The photoresist composition of claim 1 , wherein the one or more heteroatom-containing groups is —O—.

4. The photoresist composition of claim 1 , wherein each R 1 is a C 1 -C 20 linear, C 3 -C 20 branched, or C 3 -C 20 cyclic alkyl, comprising an —O— group other than at an alpha-position with respect to the amide C(O).

5. The photoresist composition of claim 1 , wherein the quencher is chosen from:

6. The photoresist composition of claim 1 , wherein the first polymer comprises a (meth)acrylate polymer.

7. The photoresist composition of claim 1 , further comprising a material that comprises one or more base-labile groups.

8. The photoresist composition of claim 1 , wherein the first polymer further comprises polymerized units of the following formula:

9. A pattern formation method, comprising:

(a) applying a layer of a photoresist composition of claim 1 on a substrate;

(b) pattern-wise exposing the photoresist composition layer to activating radiation; and

(c) developing the exposed photoresist composition layer to provide a resist relief image.

10. The pattern formation method of claim 9 , further comprising transferring a pattern of the resist relief image to the substrate.

11. A photoresist composition, comprising:

a first polymer formed by free radical polymerization, the first polymer comprising polymerized units formed from a monomer comprising an ethylenically unsaturated double bond and an acid-labile group;

a photoacid generator;

a quencher of formula (1):

wherein: R 1 is independently a hydrogen atom, C 1 -C 20 linear, C 3 -C 20 branched, or C 3 -20 cyclic alkyl, the alkyl optionally comprising an —O— group other than at an alpha-position with respect to the amide C(O), or C 6 -C 20 aryl; R 2 is independently a hydrogen atom, C 1 -C 20 linear, C 3 -C 20 branched, or C 3 -C 20 cyclic alkyl, or C 6 -C 20 aryl; wherein L comprises a plurality of heteroatom-containing groups; L is C 1 -C 20 linear or C 3 -C 20 branched alkylene comprising one or more heteroatom-containing groups independently selected from —O—, or —S—, or —N(R 3 )—, wherein R 3 is selected from a hydrogen atom or C 1 -C 20 linear or C 3 -C 20 branched or cyclic alkyl; each of R 1 , R 2 , and L may independently be substituted or unsubstituted; wherein the quencher is free of crosslinkable groups; and a solvent.

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2021
From: CARDOLACCIA, THOMAS; LEE, CHOONG-BONG; MARANGONI, TOMAS; LIU, CONG; DESISTO, JASON A.; LI, MINGQI; WU, CHUNYI; PROKOPOWICZ, GREGORY P.
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 055602/0816 →