IP Library Granted Patent US 11,859,082
Granted Patent B2
US 11,859,082 · App. 17/139,269 · Granted Jan 2, 2024

Polymers useful as surface leveling agents

Inventors: Mingqi Li (Shrewsbury, MA); Irvinder Kaur (Northborough, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
C08L71/02C08K5/0025C08L33/08C08L33/10C08L71/08C09D5/006G03F7/16
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Quick Facts
Patent No.
US 11,859,082
App. No.
17/139,269
Granted
Jan 2, 2024
Kind
B2
Abstract

Disclosed herein is a copolymer comprising first polymerized units of the formula (1); wherein: R 1 is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and R 2 is a substituted or unsubstituted C 3 -C 20 alkyl group that optionally includes one or more of —O—, —S—, —N—, —C(O)—, or —C(O)O—, —N—C(O)—, —C(O)—NR—; wherein R is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and second polymerized units of the formula (2): wherein: R 3 is a substituted or unsubstituted C 1 -C 6 alkyl group that optionally includes one or more of —O—, —N—, —S—, —C(O)—, or —C(O)O—; wherein the first polymerized units and the second polymerized units are chemically different, and the copolymer is free of fluorine.

Claims (41)

1. A copolymer comprising:

first polymerized units of the formula (1):

wherein: R 1 is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and R 2 is a substituted or unsubstituted C 3 -C 20 alkyl group that optionally includes one or more of —O—, —S—, —N—, —C(O)—, or —C(O)O—, —N—C(O)—, —C(O)—NR—; where R is H or a substituted or unsubstituted C 1 -C 6 alkyl group; wherein R 2 has a branched structure; and

second polymerized units of the formula (2):

wherein: R 3 is a substituted or unsubstituted C 1 -C 6 alkylene group that optionally includes one or more of —O—, —N—, —S—, —C(O)—, or —C(O)O—;

wherein the first polymerized units and the second polymerized units are chemically different, and the copolymer is free of fluorine; and wherein the first polymerized units of the formula (1) are present in the copolymer in an amount of greater than 60 mol %, based on the total number of moles in the copolymer.

2. The copolymer of claim 1 , where the copolymer further comprises a third polymerized unit of formula (3);

wherein R 4 is a C2 to C6 alkylene that may optionally be substituted with one or more of —O—, —S—, —N—, —C(O)—, or —C(O)O—, —N—C(O)—, or —C(O)—NR—; where R is H or a substituted or unsubstituted C 1 -C 6 alkyl group.

3. The copolymer of claim 2 , wherein the first polymerized units are of the formula (1-1), the second polymerized units are of the formula (2-1), and further comprising third polymerized units of the formula (4):

wherein: R 4 is a substituted or unsubstituted C 3 -C 20 alkyl group that optionally includes one or more of —O—, —S—, —N—, —C(O)—, or —C(O)O—, wherein R 4 has a branched structure;

4. A composition comprising the copolymer of claim 1 , and a solvent.

5. A coating method, comprising:

applying a layer of a composition of claim 4 on a substrate.

6. A pattern formation method, comprising:

applying a layer of a composition of claim 4 on a substrate;

exposing the composition layer to activating radiation; and

developing the composition layer to provide a resist relief image.

7. A composition comprising: a copolymer comprising:

first polymerized units of the formula (1):

wherein: R 1 is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and R 2 is a substituted or unsubstituted C 3 -C 20 alkyl group that optionally includes one or more of —O—, —S—, —N—, —C(O)—, or —C(O)O—, —N—C(O)—, —C(O)—NR—; where R is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and

second polymerized units of the formula (2):

wherein: R 3 is a substituted or unsubstituted C 1 -C 6 alkylene group that optionally includes one or more of —O—, —N—, —S—, —C(O)—, or —C(O)O—; wherein the first polymerized units and the second polymerized units are chemically different, and the copolymer is free of fluorine; and

wherein the first polymerized units of the formula (1) are present in the copolymer in an amount of greater than 60 mol %, based on the total number of moles in the copolymer;

a matrix polymer that comprises an acid-decomposable group; and

a photoacid generator.

8. A composition comprising: a copolymer comprising:

first polymerized units of the formula (1):

wherein: R 1 is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and R 2 is a substituted or unsubstituted C 3 -C 20 alkyl group that optionally includes one or more of —O—, —S—, —N—, —C(O)—, or —C(O)O—, —N—C(O)—, —C(O)—NR—; where R is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and

second polymerized units of the formula (2):

wherein: R 3 is a substituted or unsubstituted C 1 -C 6 alkylene group that optionally includes one or more of —O—, —N—, —S—, —C(O)—, or —C(O)O—; wherein the first polymerized units and the second polymerized units are chemically different, and the copolymer is free of fluorine; and

wherein the first polymerized units of the formula (1) are present in the copolymer in an amount of greater than 60 mol %, based on the total number of moles in the copolymer;

a matrix polymer; and

a thermal acid generator.

9. A composition comprising: a copolymer comprising:

first polymerized units of the formula (1):

wherein: R 1 is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and R 2 is a substituted or unsubstituted C 3 -C 20 alkyl group that optionally includes one or more of —O—, —S—, —N—, —C(O)—, or —C(O)O—, —N—C(O)—, —C(O)—NR—; where R is H or a substituted or unsubstituted C 1 -C 6 alkyl group; and

second polymerized units of the formula (2):

wherein: R 3 is a substituted or unsubstituted C 1 -C 6 alkylene group that optionally includes one or more of —O—, —N—, —S—, —C(O)—, or —C(O)O—; wherein the first polymerized units and the second polymerized units are chemically different, and the copolymer is free of fluorine; and

wherein the first polymerized units of the formula (1) are present in the copolymer in an amount of greater than 60 mol %, based on the total number of moles in the copolymer;

a matrix polymer; and

a crosslinking agent.

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 Feb 1, 2021
From: KAUR, IRVINDER; LI, MINGQI
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 055098/0470 →
Continuity (1)
Related Publication 20220204760A1 · Jun 30, 2022