IP Library Granted Patent US 11,880,135
Granted Patent B2
US 11,880,135 · App. 17/071,219 · Granted Jan 23, 2024

Photoresist compositions and pattern formation methods

Inventors: Mitsuru Haga (Niigata, JP); Kunio Kainuma (Niigata, JP); Shugaku Kushida (Niigata, JP)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
G03F7/0045C07D221/00C07D221/14G03F7/027G03F7/085G03F7/322C07D211/94C08F212/24C08F220/18
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Quick Facts
Patent No.
US 11,880,135
App. No.
17/071,219
Granted
Jan 23, 2024
Kind
B2
Abstract

Disclosed herein is a method comprising forming a radiation-sensitive film on a substrate; wherein the radiation-sensitive film comprises a radiation-sensitive composition comprising a photoacid generator; a quencher; an acid labile polymer formed from monomers comprising a vinyl aromatic monomer and a monomer comprising an acid decomposable group; and a solvent; patternwise exposing the radiation-sensitive film to activating radiation; and contacting the radiation-sensitive film with an alkaline developing solution to form a resist pattern.

Claims (21)

1. A radiation-sensitive composition comprising:

a photoacid generator;

a quencher that has the structure of formula (1)

wherein R 3 to R 6 can be the same or different and are substituted or unsubstituted alkyls having 1 to 10 carbon atoms and wherein R is a radical or a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, wherein R 7 is a group having the structure of formula (2):

where X is a hydrogen atom or comprises carbonyl group, an ester group, a carbonate group, an amine group, an amide group, a urea group, a sulfate group, a sulfone group, a sulfoxide group, an N-oxide group, a sulfonate group, a sulfonamide group, or a combination thereof, a substituted or unsubstituted C 6 to C 14 aryl group, or C 3 to C 12 heteroaryl group, wherein the substitution is halogen, hydroxyl, cyano, nitro, C 1 to C 12 alkyl group, C 1 to C 12 haloalkyl group, C 1 to C 12 alkoxy group, C 3 to C 12 cycloalkyl group, amino, C 2 -C 6 alkanoyl, carboxamido, a substituted or unsubstituted C 6 to C 14 aryl group, or C 3 to C 12 heteroaryl group; wherein n is 1 or 2;

an acid labile polymer formed from monomers comprising a vinyl aromatic monomer and a monomer comprising an acid decomposable group; wherein the acid decomposable group is a tertiary alkyl ester group; and

a solvent.

2. The radiation-sensitive composition of claim 1 , where the photoacid generator has a structure of formula (7)

wherein R 7 is a hydrogen atom, a substituted or unsubstituted linear or branched C 1 to C 14 alkyl group, a substituted heterocyclic group, or a halogen atom; and wherein R 8 is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a halogen atom, or an aryl group having 6 to 20 unsubstituted carbon atoms.

3. The radiation-sensitive composition of claim 1 , further comprising a polymeric adhesion promotor, where the polymeric adhesion promotor is the polymerization compound of the structure of formula (13)

wherein R 21 is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms.

4. The radiation-sensitive composition of claim 1 , wherein the vinyl aromatic monomoer is hydroxystyrene and wherein the monomer comprising the acid decomposable group is a (meth)acrylic monomer that comprises a tertiary carbon as an acid labile species and wherein the acid labile polymer has a weight average molecular weight of 10,000 to 30,000 grams per mole.

5. The radiation-sensitive composition of claim 1 , further comprising an aromatic azole compound; wherein the aromatic azole compound is a benzotriazole derivative having the structure of formula (14):

wherein R 22 is an alkyl group having 1 to 14 carbon atoms or an amine group.

6. The radiation-sensitive composition of claim 1 , wherein the photoacid generator is present in an amount of less than 2 wt % of a total amount of the monomer that comprises the acid decomposable group.

7. The radiation-sensitive composition of claim 1 , wherein the acid labile polymer further comprises a second vinyl aromatic monomer.

8. The radiation-sensitive composition of claim 1 , wherein the quencher is a base quencher, wherein an amount of the base quencher is present in an amount of 0.1 to 50 mole percent based on a total number of moles of the photoacid generator.

9. A method of forming a resist pattern comprising:

forming a radiation-sensitive film on a substrate; wherein the radiation-sensitive film comprises the radiation-sensitive composition of claim 1 ;

patternwise exposing the radiation-sensitive film to activating radiation; and

contacting the radiation-sensitive film with an alkaline developing solution to form a resist pattern.

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 Jun 1, 2021
From: HAGA, MITSURU; KUSHIDA, SHUGAKU; KAINUMA, KUNIO
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 056398/0592 →
Continuity (2)
Provisional Application 62915222 · Oct 15, 2019
Related Publication 20210181629A1 · Jun 17, 2021