IP Library Granted Patent US 8,932,793
Granted Patent B2
US 8,932,793 · App. 12/075,726 · Granted Jan 13, 2015

Phenolic polymers and photoresists comprising same

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Quick Facts
Patent No.
US 8,932,793
App. No.
12/075,726
Granted
Jan 13, 2015
Kind
B2
Abstract

The present invention relates to new polymers that contain phenolic groups spaced from a polymer backbone and photoacid-labile group. Preferred polymers of the invention are useful as a component of chemically-amplified positive-acting resists.

Claims (23)

1. A method of forming a positive photoresist relief image, comprising:

(a) applying on a substrate a layer of a photoresist comprising a photoactive component and a resin, the resin comprises a structure of the following formula

wherein each Z is the same or different bridge unit;

X comprises one or more alkyl, oxygen or sulfur atoms;

each R 1 is the same or different non-hydrogen substituent; and m is an integer of from zero to 4;

AL is a moiety that comprises a photoacid-labile group;

Y is a moiety that is distinct from the spaced phenolic group or moiety that comprises AL, and Y is selected from the group consisting of phenyl; phenyl substituted with halogen, cyano, alkyl or alkoxy; and an ester that does not undergo a photoacid-indueed cleavage reaction during exposing and developing of the photoresist layer;

a, b and c are mole percents of the respective polymer units based on total repeat units in the polymer and a, b and c are each greater than zero; and

(b) exposing and developing the photoresist layer to yield a relief image.

2. The method of claim 1 wherein X consists essentially of one or more alkyl or oxygen atoms.

3. The method of claim 1 wherein the resin comprises a structure of the following formula

each R is the same or different and is hydrogen or optionally substituted alkyl;

each Z is the same or different bridge unit;

X comprises one or more alkyl, oxygen or sulfur atoms;

each R 1 is the same or different non-hydrogen substituent;

m is an integer of from zero to 4;

P is a moiety that provides a photoacid-labile ester;

Y is a moiety that is distinct from the spaced phenolic group or moiety that comprises P, and Y is selected from the group consisting of phenyl; phenyl substituted with halogen, cyano, alkyl or aikoxy; and an ester that does not undergo a photoacid-induced cleavage reaction during exposing and developing of the photoresist layer; and

a, b and c are mole percents of the respective polymer units based on total repeat units in the polymer and are each greater than zero.

4. The method of claim 3 wherein X consists essentially of one or more alkyl or oxygen atoms.

5. The method of claim 1 wherein the resin comprises polymerized units of hydroxyphenylmethacrylate; methyl methacrylate; and tert-butyl acrylate.

6. The method of claim 1 wherein the resin comprises polymerized units of hydroxyphenylmethacrylate; styrene; and tert-butyl acrylate.

7. The method of claim 1 wherein ions are applied to the substrate after the photoresist relief image is formed.

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 May 30, 2008
From: CAMERON, JAMES W.
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 021055/0818 →