IP Library Granted Patent US 11,829,069
Granted Patent B2
US 11,829,069 · App. 16/236,725 · Granted Nov 28, 2023

Photoresist compositions and methods

Inventors: Joshua Kaitz (Watertown, MA); Tomas Marangoni (Marlborough, MA); Emad Aqad (Nothborough, MA); Amy M. Kwok (Shrewsbury, MA); Mingqi Li (Shrewsbury, MA); Thomas Cardolaccia (Natick, MA); Choong-Bong Lee (Westborough, MA); Ke Yang (Natick, MA); Cong Liu (Shrewsbury, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
G03F7/11C08F220/24C08F220/283C09D133/16G03F7/0045G03F7/0046G03F7/038G03F7/039G03F7/0397G03F7/162G03F7/168G03F7/2006G03F7/2041G03F7/322G03F7/38C08F220/1808
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Quick Facts
Patent No.
US 11,829,069
App. No.
16/236,725
Granted
Nov 28, 2023
Kind
B2
Abstract

New photoresist and topcoat compositions are provided that are useful in a variety of applications. In one aspect, new photoresist compositions are provided that comprise: (a) a first matrix polymer; (b) one or more acid generators; and (c) one or more additive compounds of Formulae (I) and/or (II).

Claims (53)

1. A photoresist composition, comprising:

a first matrix polymer, wherein the first matrix polymer comprises an acid labile group, but does not comprise fluorine;

a second polymer distinct from the first polymer, wherein the second polymer comprises an acid labile group, but is free of aromatic groups;

one or more acid generators; and

one or more additive compounds selected from

2. The photoresist composition of claim 1 wherein the second polymer is fluorinated.

3. The photoresist composition of claim 1 wherein the second polymer comprises a repeat unit of the following Formula (3):

wherein in Formula (3),

R 4 and R 5 are each independently a hydrogen, a halogen, a C 1-8 alkyl, or C 1-8 haloalkyl group, and

L is an optionally substituted multivalent linking group.

4. The photoresist composition of claim 1 , wherein the one or more additive compounds is:

5. The photoresist composition of claim 1 , wherein the one or more additive compounds are selected:

6. A method for forming a photolithographic pattern, comprising:

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

(b) patternwise exposing the photoresist composition layer to activating radiation; and

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

7. A coated substrate, comprising:

a topcoat composition, the topcoat composition comprising:

(a) a first matrix polymer;

(b) a second polymer distinct from the first matrix polymer; and

(c) one or more additive compounds selected:

and

a layer of a photoresist composition disposed on a substrate,

wherein the topcoat composition is disposed on the layer of the photoresist composition,

wherein the topcoat composition and the photoresist composition are different, and

wherein the photoresist composition does not comprise the first matrix polymer or the second matrix polymer.

8. The coated substrate of claim 7 , wherein the second polymer is fluorinated.

9. The coated substrate of claim 8 , wherein the second polymer comprises a repeat unit of the following Formula (3):

wherein in Formula (3),

R 4 and R 5 are each independently a hydrogen, a halogen, a C 1-8 alkyl, or C 1-8 haloalkyl group, and

L is an optionally substituted multivalent linking group.

10. The coated substrate of claim 7 , where the topcoat composition comprises an additive comprising an anhydride.

11. The coated substrate of claim 7 , wherein the topcoat composition comprises an additive compound chosen from:

12. A method for forming a photolithographic pattern, comprising:

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

(b) above the photoresist composition layer, applying a layer of a topcoat composition to form a topcoat layer;

(c) patternwise exposing the photoresist composition layer to activating radiation; and

(d) developing the exposed photoresist composition layer to provide a photoresist relief image,

wherein the topcoat composition comprises:

(a) a first matrix polymer;

(b) a second polymer distinct from the first matrix polymer; and

(c) one or more additive compounds selected from the group of:

wherein the topcoat composition and the photoresist composition are different, and

wherein the photoresist composition does not comprise the first matrix polymer or the second matrix polymer.

13. A photoresist composition, comprising:

a first matrix polymer, wherein the first matrix polymer comprises an acid labile group, but does not comprise fluorine;

a second polymer distinct from the first polymer, wherein the second polymer comprises an acid labile group, but is free of aromatic groups;

one or more acid generators; and

one or more additive compounds selected:

wherein the second polymer comprises a repeat unit of the following Formula (3):

wherein in Formula (3),

R 4 and R 5 are each independently a hydrogen, a halogen, a C 1-8 alkyl, or C 1-8 haloalkyl group, and

L is an optionally substituted multivalent linking group.

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 Dec 31, 2018
From: KAITZ, JOSHUA; MARANGONI, TOMAS; AQAD, EMAD; KWOK, AMY M.; LI, MINGQI; CARDOLACCIA, THOMAS; LEE, CHOONG-BONG; YANG, KE; LIU, CONG
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 047874/0880 →
Continuity (2)
Provisional Application 62612582 · Dec 31, 2017
Related Publication 20190204743A1 · Jul 4, 2019